Jamie’s Full Feminization Story
I have read a number of erotic stories of erotic feminization, and my story starts in the same way that many begin—with discovery and confession. I spend a lot of time on the details of preparation, anticipation, humiliation, and the tension that accompanies “moments of truth”.
I was on a business trip and decided that I would go through with something that I had wanted to do for a long time—get a full body wax to remove all my body hair. I went to the waxing studio and Catherine, the technician, ripped out all of my hair except for a small “landing strip” above my penis. I found the whole experience intensely erotic as I lay naked in front of Catherine for the whole procedure, put myself into several submissive positions so she could rip the hair off of my balls or around my asshole, and imagined how my new smooth legs would look in high heels. The biggest thrill was knowing that I couldn’t take this back. Unlike dressing in lingerie or makeup in my hotel room, I couldn’t leave this behind when I went home. I was going to go home and show myself to my wife, and I didn’t know how she was going to react.
I loved how my newly hairless body looked and felt, and I hoped that Emma—my wife—would, too. My mind was full of exquisitely sexy thoughts as I rode the plane, and then the taxi, home. I got home after dinner time and shared a drink with Emma before bed, and then crawled under the covers while she readied herself for the night. When the lights went out, I took her hand and brought it to my now hairless chest and said, hoping for a great reaction, “I have a surprise for you.”
Emma’s reaction was the opposite of my hopes. She recoiled at my smooth skin, saying that she couldn’t believe I’d do such a thing. She wondered if I was having some kind of mid-life crisis, so I told her that I had long disliked my hairy body and finally had the opportunity to do something about it. I told her that I did it because I wanted to feel what a hairless body would be like, not because I thought it would be attractive to her.
I was very disappointed. I had wanted her hands to greedily feel me all over my super-sensitive body, to include my hairless balls and ass. I wanted her to be curious to find out what my soft scrotum would feel like in her mouth, and enjoy the view of my dick without the thatch of dark pubes. Instead, I had another sexless night.
Things took another frustrating turn a couple of days later. Before I had gone on my trip, I had mentioned to Emma that I thought she needed some sexy lingerie. She agreed that her underwear wardrobe had gotten too utilitarian, and agreed that I could get her some lingerie for her birthday. (I didn’t say that I also welcomed the idea to pore over the frilly panties and bras in a store, imagining how they would feel on me.) So now, a few days away from her birthday, I asked her to confirm her sizes because I was going to shop for her present. She told me the sizes, and then smiled a wicked smile and said, “Sometimes I think that you really want to get this lingerie for yourself, not for me.”
My jaw dropped. She had found my secret! She knew that I liked to dress in pretty lingerie, that it made me hard. In a split second, I decided to play along, because this was my chance to get her into my fantasy and play along. I said, “I don’t know how you found out, but I would love to get some panties for myself, too.”
That was the wrong thing to say. The sexual tension left the room and Emma looked at me in disbelief. “I meant that you were getting me these sexy things because it turned you on to see me in them. What are you talking about? Are you saying you want to wear women’s panties? What is the matter with you?”
I was too shattered to try and play it cool and act like I had been misunderstood. I tried to say that there had been a mistake, and made a move to hug her and get past the moment. Emma would have none of it, “I heard what you said,” she said, “This is what the waxing was about, isn’t it? This is all about dressing like a girl. Oh my god, you’ve become a crossdresser.”
I just stammered. I wasn’t making any sense. When I started to tear up, Emma’s mood changed a little and instead of pure anger, she said she wanted to understand what was going on. “I don’t know how to feel about this right now, but I know for sure that you have some kind of secrets going on and I need to know what is going on. Have you been dressing up while you have been away? Have you been seeing someone else? What else have you been doing—sucking cock? You need to tell me everything right now, because if you keep any more secrets from me, I don’t think I can bear it.”
I could see that this was a real moment of truth. I knew Emma, and she would not stand for betrayal or infidelity. I needed to be absolutely truthful.
After a long pause, I took a deep breath and started to talk. Looking down, I started to tell her in a soft voice about my private masturbation life. I travel on business several times per month, and I told her about what I have been doing when I go away.
“Honey, please understand that I love you and only want to be with you,” I began.
“Never mind about that—tell me what you have been doing! Tell me all of it!” she said.
“OK. When I am away, I sometimes dress up in women’s lingerie in my hotel room. It turns me on, and I like the frilly feel. It turns me on, and I like to beat off while wearing them.”
“What do you wear? Exactly?”
I said, “Well, usually I wear panties, stockings, and a bra. Sometimes I have a pair of high heels that I wear, too, and I sometimes wear a garter belt. Often, I’ll wear the panties under my clothes for my business meetings during the day.”
“So my husband is a panty boy, is that it? What else do you do? Do you meet men and suck dick?”
“No, honey. I’ve never been with anyone else but you since we’ve been married.”
“I think I believe you about that. But I can’t believe that you get all dressed up just to jerk off. What else do you do?”
“Well, sometimes I get some sex toys and play with them. I will put a vibrator in my ass and stuff.”
“You dress up in panties and fuck yourself in the ass with rubber dicks. How pathetic,” she said. “Where do you get these things? And what do you mean by ‘and stuff’? I bet you suck your fake dicks, too, don’t you? You better tell the truth!”
“Yes, I do that, too. But please—don’t think I’m pathetic. I love you and only want to be with you. I buy these things at adult sex shops in the cities where my clients are. I’ve been going to the same set of 3 or 4 cities for the past five years, so I know where they all are.”
“That may be true that you haven’t been with anyone else, but I need to decide if I want to be with you. Because it is turning out that you aren’t who I thought you were. Keep talking so I can decide. What else haven’t you told me?”
“Well, I also look at porn while I am away.”
“What kind of porn? Be specific,” she said.
“Mostly sissy porn—porn about men who have been feminized. And I also like to look at sites about white wives who have sex with hung black men, with or without their husband’s knowledge. Some of these sites are the same, where a woman turns her husband into a sissy and fucks big black cocks in front of him.”
“What? Is that what you want? You want me to sleep around while you dress up like a girl.”
“No, no,” I said. “This is just a fantasy, not something to do for real. I wouldn’t want to really do anything like that. It just turns me on to think about. I don’t know why. Believe me, I’ve tried to fight it. I just can’t help it. Crossdressing and cuckolding fantasies get me hard every time. I know it makes me some kind of freak, but I just can’t help it.”
“You are right about that, freak.” Those words stung worse than anything I could imagine.
“Is there anything else?” she demanded. “You better be sure you’ve told me everything.”
I told her how long I have been doing these things, how often, and even that I had talked to her on the phone while dressed in lingerie, sometimes with a dildo up my bum. And finally, I told her the last thing: “For the last few years, Emma, I have been calling a woman named Alexa on a phone sex line called Sissyphone. She has helped me play out these fantasies.” I told her how long I had been talking with Alexa, how often, and what kind of things we talked about.
“I don’t know whether to be hurt or relieved that I didn’t have to listen to this stuff,” Emma said. Give me this Alexa’s number. Now.”
With shaking hands, I copied down the phone number from my cell phone and gave it to her.
“Now get out of this house,” Emma said. “I’ll call you when I decide what to do next.”
Jamie’s Story Part 2:
…I started to protest and say that we could talk this out together,
that this was just sex fantasy stuff and didn’t need to intrude on our
life together. Emma would hear none of it, and I saw that the best
thing to do was to leave and leave her with time to think.
The next few hours were excruciating. I sat in a coffee shop and
thought about all the things that could happen. I worried that this
was the end of my marriage—that I’d thrown away 15 years together
because I couldn’t control my urges. I wished that I was more
“normal” and didn’t want to dress like a woman or have dildos in my
ass. I hated the fact that I did.
Everything seemed to depend on whether my theory about
Emma’s inner life was true or not. Early in our relationship, she had
shown a wildness when it came to sex and a willingness to try most
anything. Early in our relationship, she had been pretty adventurous.
She’d go down on me regularly, sometimes in places where we might
get caught. She’d fuck me in all kinds of positions and now and then
let me fuck her ass.
After about a year of dating, we had broken up and Emma had
lived in a northeastern city for a period that she rarely talks about.
We and some of her friends have a name for this period—“the dark
years.” I knew that she had done some wild things, had some one
night stands, and dated some different kinds of men. My guess is
that she indulged in her fascination with muscles and tattoos on
working class types, different from me or the guys who she went to
college with at an elite liberal arts school. I knew that she had been
with at least one black man during this period, and I suspected she
might have experimented with women, too.
- Call Alexa- 888-411-1230
We reunited and eventually got married, but the sex had never
returned to the wildness of our first year together. Blow jobs became
infrequent and then disappeared. There was no question me
fucking her ass as we had done a half dozen times in our first dating
period, and she didn’t even want me to go down on her or eat her ass
as I had done in the old days. We also never really talked about her
experiences in “the dark years.” She just said that she had done
some dumb things, and left it at that.
I related this to what she was like when she drank. When she
drank too much, Emma could become a “mean drunk” and lash out
at people. Drinking removed the lid that she normally kept on
strong angry feelings that she had in side. Emma didn’t like feeling
out of control, so she rarely let herself get tipsy. (I, however, longed
to see her passions unleashed, and the possibility that she would act
out her anger and aggression on me turned me on.)
Although the sex life had cooled, my theory about her was that
she still had a wild, hot, hungry sexual being deep inside who wanted
to do more than the occasional vanilla missionary hump. Our
marriage now depended on that theory—if the flame was out, then
I’d probably broken the relationship. If there was still a fire inside
her, then we could get together. And if
Finally, Emma sent me a text around 10PM that said, “come
home.” I came to the house worried, and saw that the lights were off
and Emma was already in bed. She just looked at me and patted my
side of the bed and smiled. I undressed and slipped into bed. To my
surprise, Emma kissed me softly and we ended the night making love
—missionary—and went to sleep without saying a word.
- Call 888-411-1230 to talk to Alexa
The next couple of weeks were unreal. There was no further talk
of my confession or her sense of hurt. On Emma’s birthday, I gave
her a set of panties and a nightgown to follow through on my lingerie
promise, but it was pretty tame. We went out to dinner and enjoyed
ourselves. Basically, things seemed as though my confession had
never happened. I thought that maybe Emma had decided to
suppress what came out that day and move on as we had always
been. When we came home, we had a nightcap and went into the
bedroom; all the signs pointed to some comfortable sex before going
That’s when things changed. After I had climbed into bed,
naked, Emma came out of the bathroom in the new blue nightgown I
had given her. She gave it a little spin and asked me, with a twinkle,
if I liked it. I told her I did, and she gave a giggle like a little girl.
“I have a present for you, too, honey,” she said. She reached
under the bed and handed me a medium sized box.
“Go ahead—open it,” she said with a smile. “I think you’ll like
I opened the box and was amazed to see a big, realistic black
dildo! It was about 9 inches long and thick, with balls at the base.
“What do you think? Don’t you like it?” Emma asked. “Alexa
said that this is what you really like.”
- Call Alexa 888-411-1230 !
I didn’t know what to say. I was literally speechless. Did she
really say that she had spoken to Alexa? That couldn’t be—Alexa had
frequently told me that she would keep my confidence and wouldn’t
divulge any of my secrets to anyone without my permission.
“Show me, honey,” Emma said. “Show me how you fuck
I started to protest and say that this isn’t what I wanted. Emma
put a finger over my mouth and said, “Oh, that’s right—I almost
forgot, honey. Here is the lube. You’ll need this to stuff this big cock
in your ass.” Emma reached into her nightstand and handed me a
small bottle labeled, “Uranus Anal Lube.”
“Go ahead, honey. I can’t wait for this show. Alexa said that you
love taking big dildos like this.
I couldn’t believe this was happening. Emma had spoken to
Alexa, the phone mistress that I had shared my most intimate
fantasies with. How could this happen? Did Alexa betray me?
- Call 888-411-1230 to talk to Alexa
That’s when I remembered that in one of our most recent phone
sessions, I had talked to Alexa about what it would be like if Emma
joined in on one of my fantasies. We had played through a scenario
where she and Emma joined together to dominate and feminize me.
Alexa had asked, “do you really want that? Would you want me to tell
your wife all about you?” In the throws of my fantasies, I had said
“yes” and I had meant it. I still meant it—I didn’t want to keep
secrets from Emma and I wanted to share my whole self, including
my sissy self, with her. But I never imagined that this could really
I was hard as a rock. Alexa had told Emma about my anal play,
and I was doubly excited wondering what else she had told her. I
was also completely on fire with the fact that Emma was taking
charge and acting out one of my biggest fantasies. I decided to
comply with Emma’s orders. I took the lube and spread it on the
dildo, which started to glisten in the soft light from my nightstand. I
also took some and spread it on my ass.
- Call 888-411-1230 to talk to Alexa
“Wait a second, honey. Put that dildo next to your dick. I want
to see them next to each other.” The dildo looked huge next to my
penis. The rubber cock must have been twice as think and almost
twice as long. Emma giggled. “Your cock looks really little next to
that big dick, honey. I thought about getting you a dildo about your
size instead of this one, but I wanted to get you something you could
really feel instead. Besides, Alexa said that you like these really big
ones—and I can see why!”
This talk made me even harder than I was already. I reached
down with the dildo and pushed the head into my ass. “Wow—that
went in easy, honey. I can see you have had some practice. Now let
me see you slide it all the way in. That’s it.”
I fucked myself for a while until the dildo was balls deep. At that
moment, Emma reached over and pinched both of my nipples hard.
I arched my back and let out a moan.
- Call 888-411-1230 to talk to Alexa
“Don’t cum quite yet, honey,” she said. Stop right there and
don’t move a muscle. I like the look of your girly smooth body with
that cock up your ass.
At that second, she picked up her phone from the nightstand
and took a picture of me as a lay there on my back, legs spread wide,
big cock in my ass, big black dildo balls pressed against my balls, my
little dick waving in the air. I couldn’t do a thing to stop it. With a
few keystrokes Emma said, “I just had to send this to Alexa. She is
going to put it on her site.”
With an overwhelming wave of embarrassment, shame, and
pleasure, I arched my back and came hard all over my chest and
stomach. It seemed to pulse on and on for 10 minutes or more. All
the while I could see Emma rubbing her pussy, as her orgasm came
just after mine. “Wow, baby,” she said, “you didn’t even touch your
dick when you came—it was all about a big cock in your ass and my
hands on your nipples. You came like a girl! We need to practice
- Call 888-411-1230 to talk to Alexa
As my breath came back to normal, I started to move to withdraw
the dildo and get up. Emma pushed me back down and said, “Don’t
you move. You aren’t done.” She then scooped a big blob of cum
from my chest and brought her fingers to my mouth, saying, “open
up.” She shoved her fingers in my mouth as I licked off the cum and
pussy juice. “From now on, you will be swallowing all the cum that
comes out of your little dick, honey.” She scooped it up the rest and
fed it to me, except for the last few drops, which she rubbed into my
“And one more thing,” she said. She pulled the big black cock
from my ass in one swift move and shoved it right in my mouth.
“Alexa told me and I also saw in your internet history that you liked
ass-to-mouth videos. Those sluts love to swallow cock right from
their asses. So you better get used to it, too.” Emma laughed and
then said, “you probably will want to make sure you keep that hole
douched and squeaky clean—you never know when I will want to
use it next.”
- 9 – MARCH TREAT FOR HOUSEBOYS 888-411-1230
I was in a swirl. I could smell my ass on the dildo, but I licked
and sucked it like my life depended on it.
“That’s a good little bitch, honey. When I bought this thing, the
clerk asked if I needed some toy cleaner with it. I told her I didn’t
need it—I had my husband to clean off anything that comes out of
either of us! You should have seen how the two of us laughed about
that!” She pulled the cock from my mouth and fed me the balls.
“That’s right, lick those balls. Imagine that they are full of cum for
I had never heard Emma talk like this before, much less do
anything like she was doing. I had longed for a wilder side of her, and
now she was giving it to me with both barrels. I sucked that rubber
cock and balls like a madman.
“That’s good, honey. You have never been much good at eating
my pussy, but now I can see that your talents lie elsewhere,” I was
both humilitated by her comment on my pussy eating skills, and
turned on by her encouragement. My cock was hard again, only
minutes after cumming all over myself.
- 10 – MARCH TREAT FOR HOUSEBOYS 888-411-1230
“Now let’s see if you can take this down your throat like the girls
you like to watch. Move your head over here to the side of the bed.”
Emma positioned me on my back with my head hanging back, upside
down over the side of the bed. She held the cock to my lips and
pushed it into my mouth. I could see the balls hanging down in
front of my eyes.
“OK, baby. Open up that throat. Stick out your tongue and try
not to gag. I know you want this.” She pressed the cock deeper into
my mouth. I wondered where she was getting the technique tips
from, because she hadn’t sucked my cock in years and I don’t ever
remember her deep throating me.
After about a third of the way, I felt the head of that big dildo
pressing against the back of my throat. I gagged, but tried hard to
open the way for it. Emma kept up the pressure, and I felt my throat
give way and the cock continue its progress. “That’s good, you
cocksucker. Take that dick all the way down. Suck it like a big dick
should be sucked.”
I saw the balls getting closer to my eyes and nose, but I could
only take the cock about 2/3 of the way down. I just couldn’t get it
any farther. The gagging and effort made my eyes water, so when
Emma pulled the dick from my mouth, she said, “Aww, don’t cry,
honey. We have lots of time to practice. Pretty soon you’ll be able to
take the biggest cocks all the way down with one smooth motion.
You’ll be able to swallow a whole cock and get the balls in your
mouth, too.” It felt strange, but I had a feeling of shame—not
because I was sucking a dildo or being called a bitch, but because I
couldn’t suck the cock the whole way down. But I was happy that
Emma thought I’d be able to do it, and felt like I now had a goal to
Emma then flipped onto all fours. “Put your tongue to use in my
ass, baby, while I tell you what I have planned.” I love eating Emma’s
ass, but she hasn’t let me do it in a long time. I started by licking up
and down with my broad tongue and then circled her asshole,
burying my head between her cheeks.
- 11 – MARCH TREAT FOR HOUSEBOYS 888-411-1230 !
“I’ve had some long talks with Alexa, and she has helped me
understand what you need. After being pissed off that you shared
your fantasies with her and not with me, I realized that some of them
kind of turned me on and that we could have some fun with them. I
realize that our sex life hasn’t been that great in a while, and I was
just going to accept the fact that your little dick just can’t get the job
done. Now I see that we can both get what we need. Mmmm—I
almost forgot how much you love eating my ass. That’s good. No
stick that tongue deep in me if you like what I’ve been saying.”
I stuck my tongue as deep in her ass as I could and swirled it
around while she grinded her ass against my face.
“I thought you’d like that.” She was now rubbing her pussy with
her hand while she continued talking. “It isn’t like I didn’t know that
you weren’t enough for me in bed. I never told you why we broke up
the first time, but it was because I had started fucking this big
fireman behind your back. He had a huge dick and made me cum
every time. I knew you loved me and would do anything you could
for me, but I needed big cock so I broke up with you.”
I was shocked, but her story just drove me to lick her ass harder
“I did a lot of fucking after that with some great lovers. But after
a while, I needed stability, a good provider, and a future. Those studs
weren’t going to give that to me—they were good for banging me but
I couldn’t depend on them for anything else. So I got back with you
and found that part of me never stopped loving you.
“Now I see that you have needs, too, just like my need for the
satisfaction only a big cock—especially a big black man with a big
black cock—can give me. I had some time to fulfill my needs, and
now I’m going to let you fulfill yours. I can tell by the way you keep
licking my ass that you like this idea. Look—you are hard again!
Your dick is so cute. You must really like what is happening because
I can’t remember the last time you got hard twice in one night!
- 12 – MARCH TREAT FOR HOUSEBOYS 888-411-1230
“Now listen—I’ve gone online and found a fun way where you
can act out your fantasy dress up like the slut you want to be. I think
we can have a lot of fun together. In a few months, there is a public
Pimps & Hos party in Vegas during Mardi Gras. We can go there
with you dressed as a whore and me dressed as your pimp. I think
I’d enjoy bossing you around while you shake your ass for all to see.”
I licked harder and faster with every word. I couldn’t believe that
she was into this. I was going to get to fully dress up—in front of
other people—and Emma was going to like it. This was a nasty
dream come true.
“Suck my fingers, baby. Taste how hot you are getting me.” I
licked her fingers clean, loving the taste of her pussy juice. Then I
returned to her ass, licking that asshole like my life depended on it.
Emma started to cum as her fingers went back to her clit.
“MMMMMmmmm. Yeaahhhhhhh. Lick that ass, you bitch. Don’t
stop. You’re mine now. Deeper,” she moaned as wave after wave
came over her.
As she came down, she reached back and grabbed my hair and
pulled me head up to the pillow to face her tell me how things were
going to be going forward.
Jamie’s Story Part 3: March Treat for Houseboys
Changes: James to Jamie
“OK, honey. We are going to do this thing. But let me make
something clear—some things have changed. I’ve now seen you
grind your ass on a big black dildo and lick your own cum like you
loved it. I’ve seen you try as hard as you can to deep throat a dildo.
I’ve seen you cum like a girl, and squeal while you are doing it. I
don’t know if I’m surprised by these things or not. I am surprised
that these things make me so hot.
“I was pretty shocked when you told me that you wanted to dress
like a woman. But after I thought about it for a while, I think it kind
of made sense. You were always a bit soft, and you never took charge
the way I wanted you to. I guess I should have seen it sooner.
MARCH TREAT FOR HOUSEBOYS 888-411-1230 !1
“The fact is that you aren’t the kind of man I hoped you were. I
always wanted you to come to bed and take me, to fuck me like a real
man does, to make me cum. But you never did—and now I
understand why. You just aren’t man enough. I see that now.”
It is hard to describe how I felt. On the one hand, I felt ashamed
that I couldn’t meet her expectations for what a man should be. I
knew that I “should” be hurt by what she was saying and fight back.
In fact what I “should” have done is not tolerate that kind of
disrespect and put that bitch in her place.
But on the other hand I felt relieved—happy that I didn’t have to
try to be something that I was not. If felt like I put down a weight
that I had carried for a long time. I didn’t have to try to be a real
man, which was an exhausting, losing struggle. I could accept that I
was more feminine, more soft. This was stronger than the shame,
and even made the shame feel exciting.
- 2 – MARCH TREAT FOR HOUSEBOYS 888-411-1230
She continued, “I’ve also thought about the things I need. You
know that the only way that I have cum when we’ve had sex is when I
masturbate and you hold me. Most of the time I fantasize about
other men. I don’t say this to hurt you, but I’ve had to deal with the
truth about you, and you have to understand the truth about me.
“Before we were married, I dated some guys who really knew
how to fuck me. They had nice big cocks. Some were black, and I
loved the way that my white skin looked against his and how his big
strong muscles felt. I guess I have a thing for black men, and that is
usually what I fantasize about. If I am going to share in your fantasy,
I want you to share in mine. Now, Alexa has told me that you
sometimes talk to her about black guys—that’s why I got that black
dildo for you—and I’ve seen the interracial porn you look at, so I
know that some of this turns you on. I don’t know where this will
lead, but I need you to know that this is part of my sexuality and we
are going to talk about it more.
“Look, I love you and I always will. But something has shifted.
So this is what I want to do. We are going to do some preparation for
our trip to Vegas. I’m going to give you some things to do, and you
are going to do them—otherwise this whole thing is off. Do you
agree to that?”
- 3 – MARCH TREAT FOR HOUSEBOYS 888-411-1230
“Like what things?” I asked.
“For one, you need to drop a few pounds. 25 or 30, I’d say.
You’ve lost some weight and look pretty good for a man, but if you
are going to look hot at all in a dress, you need to lose some more.
I’ll let you know what else you have to do as time goes on.
“Now, you’ve done a good job as a provider and we have a good
amount of money in the bank. You’ve been working hard for the past
few years and we haven’t had a lot of down time together. I think
that you need to take a couple of months leave from work. Let’s
make the next few months our time. We can play with our fantasies
and get closer.”
“Umm, OK.” I said.
“And another thing. I’m going to start calling you something
different, as sort of a marker of the change that has taken place
between us. I feel like my old version of you has fallen away, and
now there is something new. Your middle name is James, so I want
you to tell everyone you want to go by that now. The man I hoped
you were going to be is over, and we are starting a new chapter, and I
am starting that chapter with James.”
“James? Why that?”
“Well, honey, I like the idea of everyone calling you something
new. Every time I hear someone call you James, I will think of the
new you that I know now—the one that likes dick up his ass,” Emma
smiled. “Also, a nickname for James is Jamie, and I think I’ll call you
that when you are in your more feminine mode. Jamie is an
androgynous name, and plenty of women use it. That’s how I think
of you now—as androgynous. Not fully a man or fully a woman, and
calling you Jamie will be fun. Or maybe your full name—Jamie
Littlecock.” Emma actually laughed at that.
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I actually blushed at this. “Jamie Littlecock.” Neither man nor
woman. It was embarrassing, but my dick—my little dick—was hard
as a rock when she said it.
“And who knows, Jamie,” Emma said with a twinkle in her eye.
“The full female form of James is Jacqueline. Let’s see how things
go, and maybe we will be in for another name change in the future.”
I didn’t know what to say. I couldn’t think past Jamie Littlecock.
I was Jamie Littlecock
The next days and weeks were a busy. I went into work and
received a three month leave of absence, telling them that Emma and
I needed some time alone and were going to take a trip. I also told
friends and neighbors that I wanted to be called “James” instead of
my given first name. They asked a lot of questions, and I told some
bullshit story about wanting to recognize a relative with that name,
but it wasn’t convincing. Everyone seemed to sense that the new
name marked some kind of change in me.
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Emma also gave me a lot to do. I’ve always been a little heavy
(sometimes more than a little), but had recently lost about 20 pounds
and was proud of looking better. Emma said that if I hoped to look
good at all as a woman, I needed to lose more and do what I could to
firm and tighten my body.
Emma signed me up for a number of exercise classes—
exclusively those mainly populated by women. For hours each day, I
did yoga to help limber up, Zumba to learn to move in a sexier way,
and Pilates to firm and lengthen my muscles. The most difficult and
embarrassing class was the “barre method” class, which was based on
ballet and was becoming popular among women who wanted firm,
trim, graceful bodies.
When I first went to the barre classes, I felt like awkward and
completely out of place. I was the only male who had taken the class
in a long time, and the instructor was used to teaching women-only
classes. She would say things like, “OK, ladies—line up with one leg
up on the barre,” then add, “and you, too, James.” I was also by far
the least graceful and flexible of the group. The other women clearly
were uncomfortable with a man in the group and thought it more
than a little odd that I was there.
After the first month, though, I became much more limber. I
also began to move in a way that was more graceful and pleasing. I
was able to chat comfortably with the women in the class and even
sometimes joined them afterward for a salad or glass of wine and a
gossipy chat after class. The instructor also stopped appending my
name to her instructions—she just referred to the class as “ladies” or
“girls” and I was just part of the group. I also switched from the tshirts
and gym shorts that I wore in the first weeks, and took to the
tank tops and yoga pants that all the other ladies in the class wore. I
liked how they looked on my slimming body.
All the exercise worked, and I lost an additional 25 pounds and
my body became flexible, leaner, and less bulky. Many of the classes
included exercises intended to lift and round the butt, and my ass
took on a rounder look than it had ever had. My legs became more
shapely and my arms looked sleek rather than thick. The only
“downside” was that I lost all remnants of “man boobs”, so there was
no hope of natural cleavage in my chest.
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I enjoyed the light, limber, feel of my body and it seemed like my
movement and posture throughout the day became more graceful
and pleasing. I spent a lot of free time with the women in my classes
talking about which instructors were better, what results we were
getting, whose asses were better looking, etc. I grew to really enjoy
hanging out with “the girls” from the gym, gym bags and yoga mats
over our shoulders, chatting away about how we were getting cuter
Emma also started to work out more and take more pride in her
body; however, she took a different approach. Emma is small and
compact, built like a natural female power lifter, and she took
advantage of her natural strengths. Emma began to seriously lift
weights and develop her muscles, and she never looked better. Her
ample ass became beautifully round and very firm. Her shoulders
and arms became defined and strong-looking. She’d wear t-shirts
that said things like “strong is the new thin”. I loved how she looked
as I always thought of her—strong, powerful, and capable of
Emma also became very friendly with the other weight lifters in
the gym, most of whom were men. She’d laugh and flirt with these
big, muscular guys, never failing to hug them hello or goodbye now
matter how sweaty either of them were. She’d admire their muscles
and complement them on their physiques, sharing tips on diet and
exercise to get “ripped.” We live in a very cosmopolitan town, so the
weight lifters included business guys, college kids, cops, firefighters,
and ex-cons of all races and backgrounds. Emma became friends
with all of them and would often hang out with them when I was
spending time with the girls. She started joining a group of them an
evening or two per week for poker nights or just some beers after
working out. On those nights, I’d usually stay home, clean up, or be
busy with bubble baths, lotions, and other things. I was becoming
high maintenance in the grooming department.
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Sex during this time was the hottest and most frequent it had
been in our marriage, although it was also different. We had some
kinds of sex at least once per day, but as Emma had promised, I
lapped up my own cum every time. Emma blew me and would even
let me cum on her face or tits—something she never did before—but
I’d have to lick it off her face afterward. When we’d fuck,
immediately afterward she would mount my face as I lay down and
I’d suck my spunk from her pussy. If I masturbated—something I
loved to do while she played with my nipples—I’d have to lick up my
cum. And of course I’d lick it up after I practiced riding a dildo and
cumming like a girl without touching my dick, which is something I
could do with increasing reliability.
She told me not to jack off when I was by myself, but I did that a
few times anyway. However, I wanted to be faithful to our
agreements, so I even licked up my cum when I did that. My cum
eating had became routine. After orgasm, I’d automatically move to
suck it up or out of her, as though that were a normal part of the sex
act. I came to enjoy the taste of cum in my mouth and the smell of it
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We went together to an adult store and bought some more sex
toys. She chose a few more dildos—a pink one that was about my
size and a white one that was about 9 inches long but not very girthy.
We also got some vibrators of various sizes. The dildos were for me,
so that I could practice deep throating, which I did several times a
week. I could easily take on the smaller one from the start, but it
took several attempts before I could smoothly take the 9 incher down
my throat easily. Emma encouraged me as I practiced, telling me that
I was becoming a good cocksucker. She applauded when I took
down the whole 9 inches and stuck out my tongue to lick the plastic
balls with the cock down my throat. I was actually proud of this—
sharing my secret desires to act like a female slut on fake dicks in
front of my wife.
The vibrators were for both of us, and she used one on me to
relax my ass—which she started calling my boy pussy—before
fucking me with the big black dildo. I grew to really love that feeling
of being taken and filled. I didn’t eat much solid food and gave
myself regular enemas so that my ass was clean and always ready for
fucking. Without hesitation, I would suck on the dildo as it came out
of my ass, going back and forth for several times a session.
Emma would also use the vibrator—or I’d use it on her—to have
earthquake level orgasms. Sometimes she would use the vibrator on
her clit while fucking the big black dildo, babbling about how good
the big dick felt and how good it felt cumming on it. There was
always the comparison—implicit or explicit—about how it contrasted
to fucking my dick, which didn’t make her cum.
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Approaching the Event
About a month before the departure, Emma took me to a local
beauty salon. I started getting facials, massages, and other treatments
as I prepared for the trip. The downstairs level of the salon was an
affiliated business, called the “Transformations Medical Spa.” All the
advertising for the place indicated that it catered to “women of a
certain age” who wanted botox, collagen, and other treatments to
look better and younger. However, after a couple of visits, the beauty
salon technicians let me know that the spa catered to the small
crossdressing community in our area.
The salon also had tanning beds as one of its services. Emma
told me that I should start tanning a couple of times a week so that I
could look my best. I agreed, and looked forward to having a golden
glow when I made my appearance in Las Vegas. I was starting to get
really excited about the trip, when I would finally fully dress as a
woman, and I was starting to think I’d really look good in my slim,
limber, body. I knew things were about to get a little different when I
was leaving home for my first tanning appointment and Emma
handed me a small bag. “There is a pretty white bikini in there, and I
want you to wear it when you tan. I want you to get nice tan lines
around your little dick and your tits, just like a girl. I think this will
help keep you in the right mindset.” I looked in the bag, and there
was a pretty string bikini, with thong bottoms and high hips, and two
triangles in the top to shield my breast area from the sun. I started
to object, but then realized that nobody would see my tanlines except
Emma, and I wanted to do what she liked.
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“There is also a little adhesive thing in there, to give you a little
heart shaped tan tattoo. Put it right below your navel, above your
dick during your tan sessions, so there is a nice little marker like a
bimbo would wear.” OK, I thought, that won’t be a problem.
My tan came along pretty quickly, and I had a nice golden tan
going in a little over a week. I also had pronounced tanlines that
clearly showed that I wore a women’s thong bikini. I liked seeing it
when I looked in the mirror—it looked sexy to me. And the little
white heard that seemed to float above my dick seemed like just the
While I was tanning, Emma made me an appointment at the
medical spa for a “day of beauty”. When I arrived, they took my
clothes and put me in a plush white terrycloth robe. Everything in
the place was peaceful, quiet, and feminine—to include the other
clients having hushed, gossipy conversations. I had a couple of
relaxation sessions and a massage, and I felt I was just floating away.
After a small spa lunch, I the went into a medical looking treatment
room, where the technician explained that Emma had arranged for a
light chemical peel and a little botox “to smooth out your skin.” I
was assured that I’d recover in less than a week.
The procedure wasn’t uncomfortable and I thought I was done
after the botox. But then the technician told me, “Don’t get up just
yet. There is one more thing.” She told me that Emma wanted my
lips plumped up a little. I was shown a chart with different sets of
lips on them, and the tech pointed to one side of the chart with a
giggle and said, “Emma ordered a set of ‘BJ Lips’ for you.” The
picture showed a pair of pillowy lips that rested in a bow and looked
ready to wrap around a fat cock. The tech smirked and said, “I don’t
know where you are going, but the boys are going to love your
I started to object, and the technician said, “Emma said that you
might complain. She said—and I quote—‘If you don’t do this, I will
call off this whole think and you’ll never get to dress like the sissy
bitch you really are.’ Now, I suggest that you lay back and let me get
to work. I’m sure that you will be happy with the result—especially
if you are as much of a sissy as Emma says you are.”
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I was dumbfounded. Up to now, the fantasy arrangement that
Emma and I had seemed like a private playing field, with nobody else
knowing about it. Sure, I was now becoming “one of the girls” and
doing Zumba and ballet exercises, but that was just a temporary
thing and I was enjoying the make believe. And I was enjoying the
pampering of the spa, the waxing, etc., but I thought of it as Now
Emma was raising the stakes and letting others know about my
fantasies and our play. How could I know how much she was telling
others? I do I know who she has told?
Not knowing what else to do, I decided to lay back and see what
my new lips would look like. Maybe they wouldn’t be that bad. I
took a deep breath, and spent the next couple of hours with the
technician injecting my lips with needles.
It only took about four day for my face and lips to heal up,
because the treatments were not that drastic. After initial redness
and swelling, my face looked noticeably younger, smoother, and more
attractive. While at the spa, my eyebrows were also plucked into a
more feminine shape. My lips looked fuller and more inviting.
MARCH TREAT FOR HOUSEBOYS 888-411-1230 !17
Overall, I looked more feminine, but not radically so. I was delighted
with the look. When I looked in the mirror, my cock got hard
wanting that mouth in the mirror wrapped around it. I couldn’t
thank Emma enough for making me go through with it—I just knew
I would look great when we got to Vegas and I was fully dressed and
Emma had my try out my new lips on the big black dildo, and
she purred with satisfaction at how good I looked with those puffy
lips sucking the cock, which I could now easily (and greedily) take
fully down my throat.
I had taken a few days off from working out while my face
recovered, but when I returned to the barre studio, the girls all
complemented me on my new look. One said, “Oh, Jamie,” they had
all started calling me Jamie without anyone asking them to, “what
have you done? You look delicious. Let me know who worked on
you, because I want the same done to me! Neither my husband nor
my boyfriend will be able to keep their hands off of me!”
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As the days ticked down to departure for Vegas, Emma continued
to push the envelope and have me make public baby steps toward
what she called my public “debut”. Emma said that it was good for
me to get used to people seeing my femme side so that I’d be
comfortable fully dressed as a woman in Vegas. I continued to
deepen my tan (and bikini lines). About a week before our departure,
I went back to the waxing studio. For the past months, I had kept
my legs and most of my body fairly hairless by shaving, but Emma
and I wanted me absolutely smooth for our trip. This was a good
time to get my body all waxed again and leave some recovery time so
that any red bumps or rashes would subside before our trip. Unlike
my first wax, Emma went with me this time.
Of course, I was embarrassed to strip down and show the
technician my naked body with its tanlines. I had forgotten that this
would happen when I had agreed to them. When the technician
raised her eyebrows upon seeing me, but Emma just said, “You
should see how cute Jamie looks in his bikini. Don’t you just love
the heart on his tummy?” The tech just giggled.
After waxing each section of my body, Emma helped the
technician inspect the work, making sure that I didn’t have any
overlooked hairs below my neck. It somehow made me feel small—
like an object—to have two women inspecting me and pointing out
where things were missed.
It made me feel completely vulnerable when Kate—the
technician—had me get on the waxing table on all fours. I had to
reach back and pull my butt cheeks apart so that Kate could paste
the hot wax on my balls, down my crack, and around my asshole and
then rip the hairs out. Emma would then get up close and point out
where a hair or two had been missed so Kate could go back and get
them. Emma said, “I want it smooth, like a college girl’s shaved
The only place where hair was left was in my pubic area. Emma
had the technician leave some hair in a well-trimmed heart shape
above my dick. She told the tech that she thought it made my “little
dick” look “cute.” It was the same size and shape as the tanline heart
just above it. She said she remembered girls from college who
shaped their pubes into heart shapes, and she liked how my hair
reminded her of that.
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During my waxing, Emma and Kate had a long talk about penises
right in front of me, making reference to me only to criticize my dick
or compare others to mine. The technician specialized in waxing
men, and she had seen hundreds of cocks, most of which got hard
during the waxing process. Emma and Kate shared stories about the
best cocks they’d seen, the worst, what they liked (thick, long) and
what they didn’t. They also compared mine to what they liked. Kate
tech said that mine “wasn’t too bad” and that she thought it was
maybe a little below average. Emma giggled and said that it was
“more than a little” below average—and told me to get it hard so she
could prove it to Kate.
I had to jack my dick while they talked about other cocks, and I
got hard right away because they were turning me on. Once I had
what Emma called my “little stiffy” going, Emma held it with a couple
of fingers and showed it to Kate saying, “see what I’m dealing with
MARCH TREAT FOR HOUSEBOYS 888-411-1230 !21
here? This is definitely not an average dick, at least compared to the
ones I’ve fucked.”
I got incredibly turned on by this talk. I had never heard Emma
talk about her sexual experiences with other men. She told Kate
about how she had fucked a “few” black men with cocks at least twice
as long as mine and much thicker. She said that those were some
real “pussy pleasers” and that they always made her cum. As she said
that, she he closed her eyes for a second as if she was savoring the
memory. They agreed that there was just no replacement for a big
cock on a real man who really knew how to fuck.
She was still holding my dick when she was saying these things
to Kate and, even though she wasn’t really stroking it, my penis
twitched and pre-cum appeared on the tip. I was so turned on I was
almost shaking. I had never made Emma cum with my dick, and she
was talking with obvious relish—longing even—about how other
men regularly satisfied her in ways that I did not.
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Emma took her hand away. “I better stop touching it or this little
thing is going to spurt all over this place,” she laughed. Kate laughed
with her and said that she agreed—now that she had seen my dick as
big as it would get, she rated my penis a “2 or 3” on a scale of 1-10.
The waxing was finally finished, but my dick would simply not go
down. Emma asked if Kate would leave the waxing room for a
“couple of minutes” so that I could “take care of the little problem.”
I was delighted, because I thought that Emma would give me a hand
job or blow me so I could cum and my dick would get soft. I was
sadly mistaken, because as soon as Kate left the room Emma told me
sternly to “jack that thing off” so we can go. And she told me to cum
in my free hand and then lap up the cum so that I’d stick to the rule
of eating all my cum. I didn’t want to orgasm in this pathetic way,
but I needed to cum and was willing to do whatever Emma wanted.
It only took me about 30 seconds to blow my seed, and another 30
seconds to lap it up off of my hand. Emma wouldn’t let me was my
hand off, so that it would smell like cum for the rest of the day.
As we left, Emma had me purchase some perfumed lotion from
the boutique to keep my skin soft and prevent ingrown hairs. She
seemed to like that I had to buy the pink-bottled lotion—clearly
marketed for women—when everyone there knew I was buying it for
As we left the studio, Kate waved to us—“Bye ladies! Have fun in
Vegas! Be sure to leave some hot guys for the other girls!” I didn’t
know what she meant and couldn’t remember that I mentioned our
trip to her, but I didn’t want to get into a discussion about it and just
turned and waved goodbye. Emma chuckled a little and gave Kate a
smile as she blew her a big kiss.
A couple of nights later, Emma said that she wanted to check out
my physical progress and see how limber I had become. She tested
me to see how wide I could spread my legs (I could almost do a split)
and whether I could lie on my back and put my ankles next to my
ears (I could). For my “final exam” she had my lie on the ground and
flip my feet and hips over my head, so that my hard dick was pointed
right at my mouth. She saw that I had become limber enough that I
could now kiss the head of my dick and swirl my tongue around it. If
I had a bigger penis, I would surely be able to suck it in this position,
but that was just our of reach. Emma had me stroke it and explode
directly into my mouth and onto my face. As I did this, Emma took
some pictures with her phone. She immediately sent them off,
saying, “Alexa really needs to see this! She’d be so proud of you!”
Final Feminine Preparations (Part 2)
We were now only a few days from departure for Vegas, and Emma turned up the intensity. She continued to push me to appear more and more feminine, even in our hometown before our trip. She told me that she was doing this so that I could practice my comportment, in my newly slimmed and limber body. I had indeed slimmed down—I had lost almost an additional 30 pounds—and my posture and balance had improved remarkably. When I thought about how I had been only a few months earlier, it seemed like I had been a lumpy, hairy, clumsy brute. Now I was smooth, tanned, and graceful. I could glide rather than clomp around when walking, and I had learned to take the opportunity to use every movement as though I was dancing rather than just lurching in some direction.
However, I think that Emma’s real purpose was to see me squirm as she pushed me to reveal more and more of my femininity to the world. Each step was a combination of embarrassment and thrill for me; I didn’t know what the consequences would be, but I was too deeply committed to pull back, even if I wanted to.
First, she took me to the local mall and had my ears pierced. She said this was important so that any swelling would subside by the time of our trip. I had to wear little gold studs in each ear to prevent it from closing up. We could have done this somewhere more private, but Emma liked having me sit at the piercing booth in the middle of the mall with all the teenage boys and girls looking and snickering. Emma made a point of steering the clerk to the more feminine earrings when the clerk made an initial mistake of thinking I was looking for more “macho” jewelry, like a young man might wear to a dance club. After looking confused and first, the clerk reviewed my eybrows and puffy lips and then—a though a light switch had turned on—suddenly smiled and said, “OK, sweetie. Now remember to rotate these studs every few hours while your ears heal. Now don’t move—you are going to feel a little prick in each ear.”
“Jamie already has a little prick,” said Emma. They both giggled while I blushed. Emma told her to put an extra hole in my left ear above the earring hole for an additional stud.
After finishing the ears, Emma took me to a jewelry store in the mall where she wanted to pick up a couple of things she had ordered. The store was not high end—instead, it was the kind of place that catered to more “street” or hop-hop looks, selling big hoop earrings, blingy chains, shiny bangles, and lots of rings for fingers and toes. When we got there, Emma asked for Shawna and a buxom, well dressed black woman came out to meet her. Emma and Shawna obviously knew each and kissed hello on each cheek. Shawna then stepped back and looked me up and down, lingering on my crotch area, and than chuckled and said, “This must be Jamie.”
I blushed again and held out my hand, saying, “Hi.”
“That’s so cute how you blush! Emma, Jamie is looking good. You girls are going to have a hot time in Vegas!” Had she really said, “You girls”? How much did she know? “Anyway, Emma, I guess you are here to pick up your order. Everything is ready. Do you want to look it over before you settle up?”
“Yes, thanks,” said Emma. “Jamie, go over there to that counter while I check out some things with Shawna.” Emma and Shawna chatted and giggled over a table as they looked through a half dozen small jewelry boxes. “These are just right, Shawna! I knew I came to the right place for custom jewelry.”
“Spread the word, Emma—we love your business. I’ve thrown in a few extra toe rings in there for you.”
“Thanks. Before we go, I want to see how a couple of these things look on Jamie. Oh Jamie, come over here.” I walked over to Emma wondering what she was going to do.
Emma took out a necklace with a thin gold chain and a script pendant that spelled out “Jamie” in cursive on gold plated metal. It looked very blingy and had a little heart over the ‘i” and finished the word with a little flourish at the end, with a small pink rhinestone at the endpoint. The effect was cute—like something a single girl in a bar might wear. “Let’s try this on and see if it is the right length.”
I turned around and Emma put the necklace on me and fastened the clasp. She then looked at me and said, “this looks just right, Jamie. Now listen—do not take this off at any time between now and the end of our trip. I mean it. Wherever you go, be sure that this is on display and is visible.
“Now turn around—I want to try one other thing on you.” I felt her put another necklace around me. After the clasp was fastened, I turned to the mirror and said that she had put another script necklace on me, this time on a slightly longer chain. About an inch below the “Jamie” script was another word spelled out. “Littlecock.” The effect was that someone looking at me would see “Jamie Littlecock” in gold in the middle of my upper chest. Now I blushed again.
“D-d-do I need to wear this, too?”
Emma grinned. “Of course, sweetie. That is your name now. I’ve taken it easy on you so when you button your shirt the Jamie is exposed but the Littlecock is covered. “
Shawna chimed in, “Just like in real life, honey. If your Littlecock was exposed when you are walking around, everyone around you would be laughing so hard they wouldn’t get anything done.” Emma liked that and gave Shawna a high five.
Shawna handed another box to Emma. “You better put this on this little hottie, too. You wouldn’t want to be accused of false advertising.” Emma took out an ankle bracelet with “Sissy” spelled out in script. She had me put my right foot on a chair and she fastened it around my ankle.
“Shawna’s right, honey. If someone sees you today, they might think you are a man. If someone sees you when you are dressed up, you might be taken for a woman. When they see this, they know that you are neither.” She paused and looked me in the eyes, and with a serious tone said, “Keep this on, too. No matter what.”
“Yes, Emma,” I said.
Emma paid for all the new things—using a debit card that drew from my checking account, as she had started to do routinely—and waved goodbye to Shawna, who kissed us both goodbye and said, “Have a great trip.” She winked when she said, “I know you will!”
From the mall, Emma and I returned to the beauty salon where my lips had been done. She checked me in for an appointment she had already made, and the attendant had me go to the changing room and put on a plush robe after stripping naked. Emma said she wasn’t going to stay, but instead go and pick up some things for our trip and her costume. She said hi to Jamie, who told her that “everything was all ready.”
The whole place smelled of flowers and perfume. I was aware that my new anklet was on display for all to see. “Emma said that we should check you over and make sure you are ready for your trip. We also have a couple of treats ready for you,” said the aesthetician. Come back here with me and I will make sure that your waxing is still fresh and give you a body scrub to make your skin extra smooth.” By this time, I was in the habit of taking direction and I followed Janet to the treatment room. Knowing the routine, I took off my robe and lay down on the table.
“Jamie, I love your tan! Your tanlines almost make it look like you have titties. I always lay out topless, but I think I will start wearing a bikini because it makes your boobs really pop.”
She then looked down after admiring my new necklaces. “Can’t say that the tanlines do anything to enhance things down there,” she said. “Now that I’ve seen hour equipment, it looks to me like you have the right name, Jamie Littlecock,” she smirked. “Ok, now lay back and let me take a close look.” She leaned closer to clinically scan my body with her eyes. ‘It looks like you are nice and smooth on your front—and I love the heart shape hovering above your little—uh—thingy. Very cutsey. You don’t need any work here, so flip over.”
She looked my backside over from top to bottom and declared it free of hair. “OK—you know what’s next. Put your fanny in the air and spread those cheeks.” I did as instructed.
“Tsk, tsk. You have a few hairs hanging on those little balls and some in your crack. Stay right there.” The next thing I knew, Janet had put hot wax on my balls and down my crack. I let out a little squeal when she ripped the wax off. “Poor baby,” she giggled, “Let me put some lotion there to soothe the sting.” Janet rubbed some cool liquid on my sack, but instead of soothing it immediately
some cool lotion on my scrotum, and my dick immediately got hard. She then rubbed the same lotion in a clockwise manner around my asshole.
“You can’t help wriggling, can you? Emma told us that you were hungry for penetration back here. Well, remember when I told you I had some treatments for you? Well, I’m going to give you the first of them right now. Relax and enjoy our special Transformations prostate massage.”
Janet placed a couple of pillows under my hips so I didn’t have to hold my ass in the air. I couldn’t help but wriggle my ass and hump the pillows at the same time. I felt my sphincter start to relax as she massaged it round and round, first one way and then another.
Soon she had a couple of fingers in me and was rubbing up and down on my prostate. I was in bliss. My ass was greedy and wanted more. I kept wrigging and pushing back on her hand, moaning as I went. The feeling was intensely pleasurable—not unlike cumming but different from it.
“Honey, you aren’t going to believe this, but my while fist is now inside you.” I felt full, but not quite satisfied. “You are going to need something really big to fill you up in Vegas. You are one cock hungry bitch.”
Did she think I was going to try to have sex with men in Vegas? That wasn’t what Emma and I had in mind. Sure, I liked to suck and fuck dildoes and liked dressing and looking like a woman, but that didn’t mean that I wanted real cock. I always got hard when Emma talked about the hung men she had been with, and Emma and I enjoyed watching interracial porn featuring big dicked black studs. We even talked about fantasies that included me getting fucked or blowing some men. But that was just fantasy life, right? To my mind, Emma and I were spending these months taking a vacation from real life and indulging in some fantasies. When it was over, then things would go mostly back to normal. I mean, sure, the cat is out of the bag that she craves big cocks and I love being feminine, but we could satisfy those issues through play, sex toys, and the occasional fantasy role play. At least that is how I was thinking about it.
“OK, sweetie—its time for the body scrub. You might want to, um, clean up,” I heard Janet say. She had withdrawn her hand from my butt, and it felt open and empty. But I knew that I had given myself an enema that morning, so I wouldn’t need to “clean up” back there. So I wasn’t sure what she meant—until I felt the set spot under me.
I had cum—a lot—while she had been fisting me. It was strange—I had been so overwhelmed with the waves of feeling coming from my ass that I didn’t even know that I had cum. “It is called prostate milking, Jamie,” Janet said. “When I massaged you with my fingers and my fist, I squeezed all the semen from your prostate. It is good for you to have it done every now and then—out with the old, in with the new, I say!”
Wow, I didn’t know that this could happen. I had really enjoyed it. I mentally filed away the experience so that I could do it again. But now I had a problem—for over two months, I had swallowed every drop of cum that had come out of me. What was I to do with that huge puddle of cum on the sheet? I didn’t like the idea of Janet seeing me lick it, so I reached for a towel to start cleaning it off of me and the table.
“Is that how you are supposed to do it, Jamie? Emma told me what to expect, but I couldn’t really believe it. I could leave you alone, but I really want to see a sissy do what a sissy is supposed to do. That’s what your ankle bracelet says you are, after all, Jamie Littlecock.”
My face was on fire from blushing again. “Go to it, Jamie. I want to see this.”
I only knew one thing to do, so I bent down and lapped up the cum puddle. I had really learned to love the taste of my cum, and I slurped every drop. I saw a flash, and saw that Janet had taken a photo of me—naked, smooth, tanlined—licking up a batch of sperm. “Emma said to send this to her, to make sure you were doing the right thing.”
As I used my fingers to wipe the last drops of cum from my stomach and legs and bring it to my lips, Janet said, “Good girl, Jamie. A cum lapping, ass fucking sissy—I am impressed. Now follow me and let’s get you that body treatment.”
I ruminated about all this while Janet gave me an all over body scrub treatment, after which my skin felt tingly and soft. She had me put my robe back on and then took me to the nail salon and sat me in a big chair. She called over some of her friends and said, “OK, Jamie. We are going to give you some beautiful nails for your trip, and tint your lashes and brows to bring out your eyes. You are going to look really pretty after this. Just lay back, and we will take care of it all.”
One technician worked on my toenails and massaged my feet, another worked on my hands, and Janet attended to my lashes and brows. I just relaxed and enjoyed the pampering.
After about a half hour, everything was done. Janet had me sit up and look over the results of the manipedi. I hadn’t expected what I saw—my toes were now a beautiful hot pink with glitter that flashed as I moved them in the light. There was nothing subtle about them. My fingers, however, now sported inch-long French manicures. The technician had placed false fingernails on them, but I couldn’t even tell that they weren’t real. They looked beautiful! So feminine, and right on the line between classy and slutty. You could imagine women with these nails at a country club tea, and you could imagine them wrapped around a fat cock.
The biggest shock was looking in the mirror at my eyes. My eyes now looked huge, framed by long, midnight blue colored lashes. My brows were now darker than they were, and even more beautiful and perfectly shaped than when I first had them done. Coupled with my pouty lips, I looked much different than I had a few weeks prior and, even without makeup, appeared womanly.
“This tinting will last for several weeks. Come back after your trip and we can touch it up for you,” said Janet. “Look—perfect timing. Emma has just returned.”
Emma walked in and smiled at me. She had an overnight bag with her, but dropped it and gave me a big hug. “You look very pretty, Jamie. Let me see your nails! How do you feel? Happy?”
I had a stretched ass, extra smooth skin, cocksucker lips, sparkling eyes, beautiful nails on my hands and feet, and cum on my breath. Of course I was happy.
“I’m so glad,” Emma said, “Let’s get you dressed so we can go home.” Emma followed me back to the dressing room.
My clothes were gone.
Emma said, “I took your man clothes away. I just couldn’t stand it any longer. I know our plan is for you to fully dress like a woman when we get to Vegas, but I decided that we could start with some baby steps now.”
She started to unload the shopping bag. “I’ve gotten to know your sizes pretty well, and I’ll be very surprised if these things don’t fit.” As she unloaded the bag, I saw some dark women’s slacks, a silky camisole, and a white cotton blouse. And some silky black panties. “Go ahead, Jamie—start getting dressed.”
I slipped the panties on and they felt wonderful. My cock was starting to respond right away. “We’ll have to do something about that,” Emma said without elaboration. The cami felt cool and silky against my soft skin, and my nipples perked right up at the feeling. The blouse would have been tight a month ago, but it fit well and I awkwardly buttoned the buttons because they were on the “wrong” side and my new nails made manipulating them awkward. Finally, I put the slacks on and sipped up the zipper, which was located on the side.
“You look just right, Jamie. In dim light, you could still pass for a man but you don’t look like a woman just yet, either. You are right in between, and that is also right were you are in life, don’t you think?” I had to agree.
She gave me some new, jeweled flip flops to wear “so that I could show off my toes,” she said. As I checked myself in the mirror, I saw that my “Jamie” necklace was beautifully framed by the blouse’s collar.
“One last touch,” said Emma, and she sprayed me with some perfume. “Chanel Allure. I think that this is just the right scent for you. What do you think, Jamie?” I loved it. It smelled pretty and sophisticated, just like how I imagined myself sometimes. “It isn’t some cheap stuff like some youngh slut would wear, but neither of us are spring chickens any more,” Emma said. “I think that this is what a cock hungry cougar would wear when she sets out to find some young stud for some sport fucking.” I didn’t know that Emma thought in those terms, but I had to agree.
We were both in our 40s and, even with all the exercise and pampering, neither of us were going to look like clubhopping twentysomethings. Instead, Emma looked to me like a woman in full bloom. She was beautiful, sexy, confident, and out to get what she wants. If she were to fuck some young stud, as we talked about during our fantasy sessions, she would be ravenous. She would be the one showing him some new tricks, not the other way around. I hoped to look something like that when we got to Vegas, or at least like a woman having a late sexual awakening.
“Let’s go home. We can start getting our things ready. We can take our time tonight and tomorrow, and the airport limo picks us up bright and early the day after tomorrow.
“Say goodbye to your new friends,” she said as we started out toward the door after she paid with my debit card. Janet and the staff of the spa had all gathered by the entrance to see us off. Some were looking at me and whispering, and some were giggling under their hands.
“You look really good, Jamie. I love that blouse! It goes great with your new lashes,” said Janet. “I wish I could go with you to see what you have coming. Send us some pictures!”
“I will,” said Emma, “Don’t you worry. I want to remember all of this for a long, long time.” Pictures weren’t something I bargained for, but I didn’t say anything at that point. I waved goodbye to the girls with hands with new nails, thanked them for everything, and went with Emma to get in the car.
We drove home silently and quickly went into the house when we arrived. I walked into the bedroom and immediately saw that something was very different.
Last Nights At Home
Before I even entered my bedroom, I sensed something had changed. Emma had a sly grin on as we entered the house and walked down the hall to the bedroom. When I walked in, my closet door was open but I saw that it was almost empty except for clothes on a few hangers and a pair of women’s shoes.
“That’s right, Jamie dear. I’ve gotten rid of all your ickie man clothes. You are a sissy now, don’t you agree that it is silly for you to dress like you think you are a man?”
“Y-yes, but . . .”
“But nothing, honey. I think it will be best that you dress in sissy clothes from now until the end of our vacation. By starting now, you will be comfortable when you get all dolled up. I’ve put a pair of 3 inch heels in your closet so that you can wear them around the house and get used to walking in high heels. You wouldn’t want to drip at the party, now, would you? Go ahead and put them on. Good—they fit.
“Now don’t worry your little brain about where your man clothes are. As far as you are concerned, they don’t exist anymore. We will deal with what comes after our trip when that time comes. I want you to focus on being your best sissy self.”
I was still getting used to the idea, but I had to admit that it made sense. I liked the silky feel of the clothes that I had on and saw that I would enjoy dressing this way for the next couple of days. I was apprehensive about how I’d look while we were traveling to Vegas, but I figured that—like everything else—I’d just go with the flow.
“OK, honey. I’ve bought you some face powder and some pale, wet lipstick that is just about the same color as your natural lips. Why don’t you go in the bathroom and put it on. You need to get some practice with makeup—especially keeping your lipstick fresh.” I didn’t really know what she meant by that, but I figured that she meant I’d have to apply my lipstick several times a day like I have always seen women do.
I went in the bathroom and did as Emma told me to do. She praised me for how I put the lipstick on. It looked subtle—you almost couldn’t tell I was wearing lipstick—but it definitely enhanced my lips and look. I couldn’t believe how much better—that is, more womanly—I looked after the botox and other little enhancements. I was really proud of how I looked. I wasn’t a young beauty, but I was starting to look like someone who could attract horny men. I imagined how much fun it would be to be on the dance floor in Vegas, shaking my ass at Mr. E (my name for Emma when she will be dressed as my pimp) while I catch the eye of men checking me out. I’d be extra excited when Emma and I finally got to our hotel room to make love. I could imagine how the whole scenario would play out. I was sure that, when the vacation ended, we would be closer and more committed to each other than ever before.
I carefully walked to the kitchen and put together a light dinner for Emma and me. We ate it while watching a romantic comedy while curled up together on the couch. When it was over, Emma told me to come with her to the bedroom. She told me to go into the bathroom and get ready for bed and to come out wearing the pair of black thigh high stockings she then gave me and the high heels, and nothing else except for my jewelry. I was to put my “Sissy” anklet on around my ankle over my stocking.
I did as she instructed, and looked at myself in front of the mirror. I liked what I saw—I was lean, almost svelte. I had trimmed down so that I almost had the “thigh gap” that women were all trying to acheive about these days. I freshened my lipstick and blotted it on a Kleenex like Emma had showed me, and then rubbed some of the perfumed Chanel body lotion on myself. Looking in the mirror, I pinched my nipples and let out a moan at the electric pleasure that shot through me. I was warmed up and ready for sex.
But I wasn’t ready for what I saw when I opened the door. Emma stood there in front of me, looking like an Amazon warrior. I drank in the way that her whole body looked firm and strong. Although she was a white woman, Emma’s body had the proportions of a Brazilian samba dancer or a black dancer on a rap video. She had strong arms and shoulders, small B-cup breasts, a narrow waist, thick thighs, and a wonderful round ass. As a result of her weight lifting, it was all in formidable shape. She had also refreshed her makeup, with deep red lips and dramatic eye shadow. Like me, she was wearing black patent leather high heels. But unlike me, she was also sporting a huge hard cock.
Emma was wearing a big black strapon cock. It was about ten inches long, thick, and realistic with a big head, veins, and balls. Although she had used dildos on me before, I had never seen her with a strapon. She looked fabulous and full in charge.
“Get over here, sissy. I’m going to fuck you silly tonight. You are getting ready to fulfill your dream of looking like a woman, so I want you to get fucked like one. That is, to get fucked like a real man fucks a woman. So get on your knees and suck my big cock.”
I never wanted to do anything more in my life than to suck that cock. I knelt before my wife and sucked that strap on cock for all I was worth. “That’s it, bitch. Keep looking up here, in my eyes while you do it. I want to feel the connection while you kneel and suck.” Doing as I was told, she grabbed my head and pushed me onto that cock as I took it into my throat. “Deep throat that black cock, baby. You’ve been practicing, so I know you can do it. Now take it all the way in and press your nose into my tummy with that tick all the way down.” After a couple of failed attempts, I had the whole dick in my throat and I even extended my tongue to lick the balls.
“Nice blowjob—you do that like a real slut, baby,” said Emma. “Now get your head down, ass up, and I am going to fuck you. Now listen to me—do not touch your little sissy dick. I want to make you cum without anything touching it.” I bent down and put my ass in the air, waiting for her. I didn’t have to wait long—she coated my ass with lube with her fingers and stuck the head of the dildo in.
“Easy, babe. Let me get used to it,” I said.
Emma slapped me hard on the ass. “Shut the fuck up. I didn’t ask you how you felt. Take this cock and fuck it like the slut you are.” With that, she rammed the rest of the cock in me. It felt like an explosion that left my ass on fire. But quickly, that pain subsided as she jackhammered me and I felt that familiar pleasure of having a big dildo in my ass. I fucked her back as much as I could.
She pulled the dick out and my ass felt like it was open a mile wide and unnaturally empty. Emma slapped my ass again told me to get on the bed, on my back, with my legs spread wide and high in the air. As I did that, she stood at the edge of the bed and placed the tip of the cock against my hungry sissy pussy. Then she grabbed my ankles and, holding them firmly and wide apart, impaled me with that strapon cock. She then put my ankles on her shoulders and her hands on my nipples. I was in ecstasy, having totally surrendered to my beautiful, powerful wife. I loved the look of my stockinged legs in the air above me and my pump-shod feet framing the lust-filled look on Emma’s face as she drilled me. Just as I thought she was going to make me cum hard. Emma stopped and told me to lie back on the floor and hook my legs over her arms.
The next thing I knew, my head and shoulders were on the floor but my ass and legs were up in the air. I was doubled back on my self with Emma standing with her feet behind my shoulders. She stuck her cock in me and fucked me hard. In this position, my hard dick was just in front my own face. Unlike the last time I was in this position, the fucking that Emma was giving me pushed down on my hips. In just a few strokes, Emma pushed the head of my cock into my own mouth, where it exploded. I swallowed almost all of my cum, but a few spurts escaped to my cheek and chin. They were still there when Emma pulled the cock from my ass and roughly grabbed my head by the hair and pulled my mouth to the cock.
“That’s it, Jamie, you slut. Drink that cum. Now be a good bitch and suck this strap on cock fresh from your ass. You have done well with the rule of swallowing all the cum that comes out of you. I am now going to set two new rules which are to be observed until I say different. First, you are never allowed to cum unless you have something big in your ass. Second, when a dildo, toy, finger, or whatever leaves your ass, the first place it goes is in your mouth. Got it?”
I showed my approval by taking that cock down my throat again. If that meant I could get her to fuck my ass more, then I was all for these new rules.
After a few minutes, Emma told me to stop sucking and to come up and rest on the bed and lay on my back. Emma stroked my hairless body and said, “You did well tonight. I wanted to make sure you were ready for our trip. You seem like you have your mind in the right place play the whore at the party when we get to Vegas. Like they say, you’ve come a long way, baby.”
“Now I have one more rule to make, because I want to keep you ready for the next few days, “ Emma continued. She reached into her nightstand and pulled out a velvet bag. “I want you to be a truly motivated whore when we get to Vegas, so I am going to put this on you.”
I recognized what she pulled from the bag as a CB6000 chastity device for men. “I am going to put this on you to make sure that you don’t stroke your little cock before I am ready to let you. For now, that means I’ll keep you locked up for the next couple of days before the party. Be a good sissy, and I’ll let you out then.
“Beyond keeping you horny, I also want to get you in the right frame of mind for the party we are going to. You are going to play the whore, and a pimp controls every aspect of his whores. So I want you to be totally under my control. Locking up your dick—such as it is—will be a constant reminder that you are under my control right down to your core.
“And one other thing. This will also get you to focus your sexual pleasure away from your sissy clit and onto your ass and your nipples. You’ve already showed me that you can cum like a girl; now that will be the only way for you to cum. That will also keep you in the mood to play the whore.”
I had already come so far down the road of feminization, this seemed like just another step. Of course, I agreed with Emma. It would be better to say that I submitted to Emma; my agreement or disagreement no longer seemed material.
As Emma fitted the device onto me, she said, “You should know that this is the CB6000S model. The S stands for ‘small’, and it is for smaller than average penises. It looks like yours fits in there just fine.” With that she closed the lock with a pronounced click.
Emma took the key and threaded a think gold chain through it. “Jamie—help with the clasp, honey. I’m going to wear this as a necklace to remind you—and anyone else who sees it—that I control the key to your dick. I wonder how many people will know what is going on when they see it. Won’t it be fun trying to read their faces when they look?” I closed the clasp behind her neck.
“Just think, honey. In two days we will be in Vegas. And in just four we will be at the party, living out our fantasies. I’m so excited. I have checked on all the arrangements: our costumes, your makeover, our hotel, and entertainment for the evenings before the party. Everything is in order and we are going to have the time of our lives! Just thinking about it gets me all wet, and unlike you, I haven’t cum yet. I want you to fuck me with that big black dildo before we go to sleep.”
I did just that. After warming her up with my tongue and lubing up the dildo with my spit, I fucked her with the big black rubber cock. She had no trouble taking it all in, and she writhed on the sheets as I slid it in and out. “That is so good, “ she said, “I love that thick black cock. Fuck me with that black cock. I can’t get enough of that big black cock. HMmmmmmm. I’m cumming! Black cock always makes me cum so gooooood!” By the end, she was just babbling on and on about how she loved that black dildo. As she settled down, I pulled the dildo out of her, swabbed it clean with my tongue, and put it away. I spooned behind her, ready to go to sleep. My caged dick was nestled between her cheeks and I could feel her heat. For the first time, I felt my penis strain against the plastic cage. It wouldn’t be the last.
After waking up the next morning, I dressed in my femmie attire and high heels. Emma had to go to the gym and run errands for most of the day. My job was to clean up the house—Emma hates to return to a messy house after a trip—and make sure that I was packed. I carefully laid out my clothes and toiletries. I actually wasn’t taking many clothes because Emma had arranged for me to pick up more female clothes in Vegas after we arrived. I checked and double-checked everything. I also made sure that I put the dildos and sex toys we were bringing in my checked bag so that I wouldn’t be embarrassed going through security.
Emma got home in the late afternoon saying that she had had a doozy of a workout and then spent some time hanging out with her gym friends. I knew most of them were men, and I felt a little jealous. However, I didn’t say anything and focused on the great time together that we were about to have.
I let her know that I had everything packed and would be ready to go in the morning. Emma told me there was one other thing I needed—and she tossed me a baseball cap. She said that we both knew that I was going to get a wig when we got to Vegas, but that my short, balding man hair just wouldn’t do for the trip. She wanted me to wear the cap while we traveled. I looked at it and saw that it was white with the word “Pink” across the front. I recognized it as coming from Victoria’s Secret and recalled seeing teenage girls wearing hats like this around town. I actually agreed that the cap would be a good touch.
There was no sex that night. Emma said she was tired and we needed to get up early in the morning. Emma had arranged for one of her gym friends to drive us to the airport, and he would pick us up at 7AM. I had trouble sleeping because I was getting very horny. Also, my dick strained against the cage at night as it tried to get hard during my sex dreams, waking me up with a painful ache. I tried to remember that it wouldn’t be much longer and did my best to rest as much as I could.
I was awake well before dawn and dressed as I had in the previous few days—pretty panties, silky camisole, pretty blouse, dark slacks with the side zipper. Instead of heels, I wore a pair of fancy pink flip flops—Emma wanted me to have my pedicured toes exposed.
Emma dressed alone in the bathroom. When she emerged, I was stunned by how she looked. She looked magnificent. She wore a silky white blouse and a close fitting black skirt with a slit up the thigh. She also wore dark stockings and one could see the garter fastener at the slit when she sat down. She also had on 4 inch heel pumps—something she rarely wore out and about. Her makeup was perfect and her perfume smelled wonderful. The three buttons open on her blouse framed the little key she wore as a pendant and offered the faintest glimpse of a black lace bra if you had just the right angle. Her fit body seemed to ripple under the clothes, and her ass never looked better in that skirt. The overall effect was breathtaking. She looked like a strong woman in charge of her surroundings, which obviously included me.
“Are you ready?” she asked.
“OK. Here we go. This is going to be fun for everybody.”
I had made coffee for us, so we sipped it in the kitchen while we waited for the car. Emma said that she had forgotten something and went back to the bedroom, where the bags still were, and took care of it. She came back after a few minutes just as the car pulled up in the driveway. I went and brought the bags out as she went out to greet her friend.
As I approached the driveway, I saw that she had embraced the driver and kissed him hello. They whispered something together and laughed about it together as I brought the bags to the car. When I approached the car, I thought I heard Emma tell Darrell about how she was still, “sore from yesterday.” I guess she must have had a tough workout at the gym.
“Jamie, this is one of my . . . uh . . . workout partners, Darrell.”
“How do you do,” I said. I saw that Darrell was a large black man, about six foot two, with a weight lifter’s muscles. He looked like the embodiment of masculinity. It made me acute me aware of how far I was from that.
Darrell let out a little laugh as he gave my manicured hand a firm shake. “I’ve heard a lot about you, Jamie. Wait—what does your necklace say? Jamie Littlecock? That’s fucking hilarious.” Darrell and Emma shared a conspiratorial look.
“Never mind that, Darrell. It is all part of our vacation game,” Emma said. “Thanks for taking us to the airport. Jamie—you get in the back seat. Darrell will load the trunk. I don’t want you to chip a nail.”
We got to the airport where Darrell dropped us off and helped us get our checked bags to the curbside check in. “Have a good flight. See you soon!” he said, as he gave Emma a warm hug and then pulled off.
With the bags checked, Emma and I made our way to the gate. We already had our boarding passes, so we went straight to security. The TSA agent at the front of the line looked back and forth from my driver’s license to me and back again about a dozen times before clearing me to go on—I had to explain that I’d had my lips done and that is why I looked different from my picture. He shook his head and said, “I guess it takes all types,” and waved me on. My cheeks were burning because I was blushing so much.
Emma let me go ahead of her through the metal detector. Even though I didn’t have any pockets and wasn’t wearing any metal other than my jewelry, the metal detector went off. I went back and took off my necklaces and anklet, but the metal detector went off again. That’s when I remembered about the metal lock on my cock cage. I hadn’t thought about it setting off the security alarm, but that is what was happening and I couldn’t take it off. Deeply embarrassed, I stepped forward so the guard could use the wand on me. With everyone looking, it was clear that the alarm was triggered in my crotch area. “What is that?” the agent said.
“Umm. A lock.” I replied.
“A lock. OK, we get your types here now and then. However, we have to do a visual inspection to make sure that is what it really is. Follow this agent to our inspection room.”
I didn’t have any choice. I looked back at Emma, who had sailed through security, and she was wearing a big smile. She was enjoying every second of my embarrassment.
I followed the agent to the room and entered it. There were two agents there, one male and one female. “We can’t decide which gender you are, so we decided to both come,” the male said. “Please open your pants so we can visually confirm what set off the alarm.”
I took a deep breath and unzipped the zipper at my hip. I dropped my slacks and then pulled down the front of my lacy panties. The female TSA agent could help herself and covered her mouth as she tried to suppress the giggles. The male just said, “Damn—now I see why you are locked up. That thing is useless. You aren’t any danger to anyone with that. Get dressed and get on your way.” They turned around and shared a laugh at my expense.
I was mortified but relieved that the inspection was over and returned to the security station to pick up my carry on bag. When I got there, the agent picked up the bag and said, “Uh, sir . . . ma’am . . .uh . . . is this your bag?” I replied that it was. “And is this yours too?” With that, she pulled out the big black vibrator that I like to use. I was confused because I knew I packed it in the checked bag to avoid just this kind of problem. I looked around and saw Emma laughing at me. She must have put the vibrator in my carry on as a practical joke. She was really enjoying herself.
“Yes, officer, it is mine. Is there a problem?” I said, trying to hold it together.
“That depends. I need you to turn it on for me and show me how it works before I can let you proceed. I have to make sure that you don’t have something other than batteries in there.”
I walked over and took the vibrator from him and turned the dial so it started buzzing. “There, are you satisfied now?”
“No, but I bet you will be when you use this on yourself,” she said. “You can go.” I started gathering my things. “What a fucking sissy,” I heard her say under her breath. I saw that a small crowd had gathered watching me, and they were all smirking.
I was mortified by the whole situation. But I couldn’t help but notice that I was also turned on. My dick was straining against the cage.
I put my bag back together, slung it over my shoulder, and started to head toward the departure gate with the remaining shreds of dignity that I could muster. Emma joined me. “I couldn’t help myself. I was chuckling to myself the whole way here because I wanted to see how you’d react when they found your lock and the vibrator. You put on quite a show.” I noticed that Emma didn’t apologize.
I just wanted to get on the plane. We finally boarded and took our seats. Emma and I ordered bloody marys as soon as the beverage cart came, and I had another as soon as I could. Eventually, I dozed off. When I awoke, Emma wasn’t in her seat and I needed to pee. I got up and headed back to the lavatories, and I saw that Emma was chatting with some of the flight attendants in the back of the plane. As I got there, I heard one of them say, “And you really only let him cum when he has something big inside of him?” “Insider of her,” Emma said, “I call Jamie ‘she’ now.”
Just then, a male flight attendant saw me and said, “Well, speak of the she-devil. There she is.”
An older female attendant said, “Hello, Jamie. Your wife has been telling us about your big vacation plans. Sounds like she has some big things planned planned.” They all smiled at that. “I’m not sure if I believe everything she has told me, though.”
“Oh, you don’t?” said Emma. “Jamie—be a good girl and go get that black thing you have in your bag and come back here with it.”
“Emma, are you sure that is a good idea?” I said.
“Shut the fuck up, sissy. Do what I told you. Fetch that vibrator.” I turned right around and did as she instructed. When I came back, she told me to go back into the galley where the flight attendants—who seemed to be on break—could see me but the other passengers couldn’t. First, she told me to show her new friends how I could deep throat the vibrator. I spit on the nine inch plastic toy and spread it around to lube it up, and then opened my mouth and slid it all the way down in one stroke. “Hold it there. Hold it. OK—take it out,” said Emma. I did as she said and did my best to catch my breath.
“What else don’t you believe?” asked Emma.
“I don’t believe that Jamie can cum like a girl. I just can’t believe that anyone with a dick can cum without stroking it,” said the older flight attendant, whose name was Louise.
“I don’t either,” said the male. “I’m the bottom in my relationship with my boyfriend, but that has never been enough to satisfy me.” Obviously, he fit the cliché that most male flight attendants are gay.
“I’ll do you one better. Jamie is so feminized that she can cum just by fucking that vibrator, even though her dick is caged and can’t get hard.”
“I’d have to see that to believe it,” said Louise. “Me, too,” said Anthony, the steward.
“You heard her, Jamie. I don’t think that you should do that out here, but you go in the lav with Lisa and Anthony here and do what I said. Don’t stop fucking yourself until you cum. Don’t you dare prove me wrong, and be sure to follow all the rules.”
“Yes, Emma,” I said. I went in the lav and took off my slacks and panties. Louise and Anthony came in and stood there. “OK, start the show,” said Louise.
I put one leg up, setting my foot on top of the toilet and, lubed up the vibrator again with my spit. I turned it on and slipped it inside my ass. I closed my eyes and felt it hum deep inside me as I pushed it in and out. Before I knew it, all I could think about was how good it felt to have something fucking my ass. I worked my ass up and down on that vibrator while tweaking my nipples with my other hand. Louise stepped forward and started pinching both of my nipples while I steadied myself on the counter. She said to Anthony, “I think I’d like to have a sissy like this one. I’ve had some asshole men in my life, and it would be fun to be able to take out how pissed off I am on a feminized bitch like this one. It would be very therapeutic.”
With that, she gave my balls a hard slap, making me jump.
“I’d just like one to keep around and suck my dick whenever I wanted,” said Anthony.
My dick strained against the cage and then, in a big wave, spurted cum as Lisa twisted my nipples hard. I tried to stifle my moans, but I’m sure that people a couple of rows ahead could hear me. Out of habit, I caught the cum in my hand. When my hand was full, I immediately brought it to my mouth and started to lick it all up.
“Damn, Jamie. I wouldn’t have believed anyone could, or would, do that unless I saw it myself. I’ve fucked a lot of men in my life, but I’ve never seen anything like that,” said Anthony.
“Stop licking that cum, bitch,” said Louise. “I know you love the taste, but I want you to take what is left and smear it all over your face. Rub it in.” I was surprised at how angry she sounded. “I used to fuck this man who loved to cum on my face and always tried to make me walk around in public with his cum on my face. He wanted to mark me as his. I didn’t want to do it, but I wanted to please him so I did it a couple of times. It wasn’t long after that when I found him cheating on me. I can’t believe I humiliated myself like that.” She paused a beat.
“So I am humiliating you as his proxy. If he were here, I’d make him do it. But he isn’t, so I’m doing it to you. Don’t you dare wipe off your face until this flight is over.”
I did as she told me. Then I went to the next rule and took the vibrator from my ass and sucked it clean with my mouth. Anthony said, “I always do that, too. I love to suck my lover’s cock clean after he fucks me.”
“Emma has you trained well, I’ll give that to her,” said Louise. “She told me about her plans for you in Vegas. I just wish I could be there to take part. It is going to be unbelievable. You are the biggest sissy I have ever seen.”
When we departed the lav, Louise and Anthony told Emma how right she was. Louise then told Emma about her instructions to me, and Emma smiled with delight. “Anytime you want to take out your aggression, feel free to use Jamie as your punching bag.” I didn’t know what to make of this. I had thought that our fantasy weekend was something for me and Emma to share. This whole event put a different twist on things. I wasn’t going to talk back to her at this point, though. I had too much invested in the trip to make waves. I figured we could discuss it afterward
The flight attendants congratulated Emma on what she had done. They said they hoped that they were on our flight back so that they could hear all the juicy stories. Emma and I made our way back to our seats. I could already feel the cum on my face drying into a light glaze.
As we approached the Las Vegas airport, the captain made all the normal announcements about the gate and time of arrival. Then he added, “And folks, I want to let you know we have a couple making a special celebration on our flight. Please give a round of applause to Emma and Jamie, who are starting a new life together. Our crew wants to wish you all the best and let you know that they can’t wait to see you on our flight again.” The whole plane applauded.
As we exited the plane, I saw Louise nudge the captain and point me out as he was saying goodbye to the passengers. “Let me know when you fly back home,” he said. “We’d love a sissy show in the cockpit.” I was speechless, and blushed hard as I walked off the plane.
Girls in Vegas (Finally) (Part 3)
We took a taxi to our hotel, Paris, and went to the check in counter. The clerk looked us both up and down, and then said, “Welcome, ladies. It is good to have you here. Your suite is ready for you.” Emma handed over her ID and credit card—my card, I noticed—and took care of the formalities. “Why don’t you head up and I’ll have the bellman take up your bags. I know you will have a memorable visit.”
We thanked them and started to head to the elevators, when the clerk called after us, “We had your flight information, so I’ve taken the liberty to send up a complementary gift. I hope you enjoy it. We always love having girls like you here.”
We waved thank him, and then I noticed the signs that proclaimed the Paris hotel as LGBT friendly. I looked around, and I noticed a few girls who might have been crossdressers, but I couldn’t tell. Emma had made all the arrangements and wanted to keep the itinerary a surprise, but I had to agree that she picked the right place.
I knew that the Pimp & Ho Party would also be at this hotel, and the advertisement and online chatter had made it clear that it was the most diverse such party anywhere. There would be straight people, gay people, transgender people, white people, black people, and all other kinds of people. In previous years, there was also representation of BDSM people as well as real pimps and prostitutes. Basically, there were no rules except for trying to make others feel bad (unless they want to feel bad).
When we got to the room, we saw that there was a bottle of pink champagne waiting for us. Emma opened it and poured us a couple of glasses. “This is a toast to you, Jamie. I can’t thank you enough for opening up to me. A whole world of possibilities is now available. I want you to know that I love you and always will, no matter what.” We clinked glasses and savored the bubbly, but I had to wonder what “no matter what” meant.
The bellman delivered the bags and showed us around the suite. It was large—a big sitting area with a sectional couch and ottoman, two bedrooms, and a huge master bath with a hot tub that could easily fit four people. “Are you sure this isn’t too expensive, honey?” I asked.
“Don’t worry about it baby. It is all taken care of. Don’t worry your newly pretty little head over it.” I said OK while Emma tipped the bellman.
Emma said, “I don’t know about you, but I just want to relax today and take it easy tonight. I’ve arranged an appointment for you today at 4—it is about 2PM now—to get you a makeup lesson and some clothes. This will also allow us to confirm your sizes so you hooker costume fits perfectly for the party. I’ll go with you to make sure everything is just right.”
I was delighted. Finally, I’ll get a professional makeover and be able to appear as much like a woman as possible. Emma told me to take a shower and clean my face—of any lipstick and anything else—and we would head out.
At 3 we caught a cab to Just You, a business specializing in male-to-female transformation makeovers. Emma had been coordinating with Amy, the owner of Just You, for weeks and planned to use it as the base for dressing me and making me up.
We arrived a little early, and Amy greeted us enthusiastically. “Emma! I am so glad to finally meet you. I have done everything we talked about, and I think that we will be ready for a great few days.” When Amy finished hugging Emma, she turned to me, “Jamie—or should I say Jamie Littlecock?—I am so happy you are here. Put yourself in my hands and I am sure that I can deliver on the vision that Emma shared with me. You are going to be one happy girl, I promise!”
With that, Amy took me into the dressing room. A previous client—who looked like a woman ready for a night on the prowl for men—waved goodbye as she left.
Amy said, “Jamie, what we are doing here is a complete makeover and dress to present you to the world as a sexy woman. They way I work is to start from the very base level, so what I need you to do is to strip naked and stand on that little platform so I can see what I am working with.” She pointed to a platform about a foot high that stood before a set of three mirrors, much like you would see in a tailor or dressmaking shop.
I looked at Emma to see if that was right, but Emma said, “Don’t look at me. Amy is the expert here in helping sissies look like girls. Do what she says—its what we came all this way for.”
As Amy and Emma chatted, I took off my blouse, camisole, and pants. “Panties too,” I heard Amy say, so I took them off as well. I stood totally naked on the platform and waited for Amy to turn her attention to me.
After a couple of minutes, Amy came over and examined me up close. “Emma, you and Jamie have done a remarkable job. Her body is lean—I think the word is lithe. Well, almost lithe. Her basic architecture is still like a man, but we can do a few things about that for dress up. Really changing that will require more, uh, decisive methods.
“You have done a great job with her nails, hair removal, and skin care. I love what you’ve done with the eyebrows and lashes. And I really love the tan—it shows that Jamie has been getting into her girly mindset for some time.
“I don’t see any real problems with passing her as a reasonably attractive woman. I mean, she won’t be model pretty and anyone who really looks at her will see that she has the shoulders and frame of a man, but she will be a great looking sissy. The main issues are the waist and what to do about her penis. I see that she lives up to her name in that department, so this is a solvable problem. You can keep her caged but that shows a bulge, you can cover it up, or you can leave it relatively free if you expect to use it while in woman mode.”
“We’ll leave it caged for now. I will let you know tomorrow about what we will do for the party,” said Emma.
“That sounds fine,” said Amy. My recommendation is to dress her up now and make sure she can put on basic makeup. Then you come back tomorrow and we will dress her for the big event!” Wow! That means that from this afternoon forward I’d fully dress as a woman. I felt so happy, but I immediately registered that my dick was straining in its cage.
Emma agreed with that plan. “OK, Jamie. The first step I like to do with my girls is put them in some proper shoes. I want you to wear heels all the time from now on. Unless you are in the bath or shower, or you are sleeping, you should be wearing the shoes I give you. Do you understand? Every step from now on will be in heels. And it goes without saying that they stay on if Emma has any sex planned for you. Do you understand?” I agreed immediately.
Amy gave me gold strappy sandals with a high 4 or 5 inch heel. I wasn’t used to wearing heels this high, and it showed. “Walk back and forth in here a couple of times to get your sea legs, so to speak.” Still naked, I walked a few laps across the room. “Emma, you once again have my complements. Jamie is a little wobbly, but she swings her hips and knows how to walk in heels. Her ass looks high and round, and she has a great pair of legs. We need to be sure to show them off when she dresses up.”
I felt completely exposed as Emma and Amy inspected and talked about me. But I was thrilled as well, and loved the approval I was getting.
“OK, Jamie. I want to start changing your hair and a few other things, but I won’t leave you naked. Put on this robe and we will move on to the next steps.” Amy handed me a pale blue frilly dressing robe. I think the right word is chemise, and it felt heavenly—it was frilly and soft, and its every touch felt like a caress.
Amy sat me down and said, “Let’s find the right wig for you. This isn’t necessarily the hairdo you will have for the big party—we will work on your evening look later—but I think we need to get you some nice hair for the next day or so.” Emma had sent Amy pictures of me ahead of time, and Amy had already chosen a short blond wig with a pixie-like hairstyle. “Here, let’s try this,” she said as she placed the wig on my head and adjusted it.
“I’m going to let you look in the mirror now. I think you will like the effect,” Amy said. I looked in the mirror and was stunned. I hadn’t even put on any makeup and the wig made me look, well, pretty. At least almost pretty. Combined with me full lips, shaped brows, and tinted lashes, the effect was really transformative. My heart leapt.
“I love it,” I said, as my eye teared up.
“I thought you would. The color plays off of your natural skin tone and tan. I think that this is a feminine, but sporty look that goes with your fit body. A flowing or girlier hairdo would be out of sync with the rest of you. This says that you are a girl who knows how to use her body,” said Amy.
“That will come in handy,” smiled Emma. “You do look great, honey.”
Amy spun me around in the swivel chair. “OK, now let’s get you some jewelry and get you made up.”
Amy told me that normally, she likes to do a makeover so that the subject doesn’t see the result until the end. That is what she is going to do tomorrow, before the party, but today she wanted to show me how to make myself up so I could maintain my own makeup for the next day until the party.
Amy selected some pearl earrings and a short pearl necklace for me to wear alongside my “Jamie” and “Littlecock” necklaces. Then she showed me how to put on a makeup base, how to use blush, and how to paint my eyes and lips. “Tonight, I’m going for a wholesome, attractive look, like a woman who plays tennis at a country club. You will be pretty and attractive, but not as dramatic as you will look tomorrow. This look will be suitable for evening tonight, and all day tomorrow. You can also use this when you go home and want to dress up there. It is very versatile.”
That sounded wonderful to me. I’d live a whole day as a woman, without looking like a whore all the time.
“The skirt I am going to put you in will solve the bulge problem, but we need to address the waist. I’m going to put you in a corset that I’ve gotten ready for you. Emma sent me your measurements and, looking at you now, I am confident that it will work. Not only will the corset give you a much-improved figure, but also I normally tell my girls that it will improve their posture. However, in your case I see that you have wonderful posture and that isn’t necessary.” I silently thanked the universe for the barre classes; many people have noticed that my posture and general way of moving is better and more graceful since I started with that training.
Amy had me put my hands against the wall and lean out while she placed the black cotton corset on me. It was a relatively narrow, stiffly boned underbust corset that covered the length of my waist. It was already a little tight when she initially put it on me, but when she started lacing it up the constriction was almost too much to bear. I found it difficult to breathe and got a little light headed—I could definitely understand why Victorian women fainted in all of those 19th century novels.
The effect was immediate, however. Emma’s eyes widened and she said, “Oh my God, Jamie. You look wonderful. The corset gives you a wonderful hourglass shape—it must have taken five inches off of your waist.” She then broke out in what can only be called an evil grin; “You are going to have men chasing you all over the Strip.”
Amy was also pleased. “OK, I’m going to break my own rule. I want you to look in the mirror and see how this looks, because it is really remarkable.”
I turned and looked in the mirror, and almost couldn’t believe the (almost) woman that looked back at me. I was tall, lean, shapely, and attractive. My eyes lingered on the smooth legs, pretty nails, perfect hair, and small waist. I would definitely fuck me.
“That’s enough. Turn around and let’s finish the job.” Amy chose a pretty lace bra and D cup breast forms for me. “You need some big tits because of your broad shoulders. These will work tonight, but we can see if you need something bigger tomorrow.”
“That’s right—Jamie definitely needs some big titties,” said Emma, still smiling.
She then gave me some pretty matching white panties, a white garter belt, and tan stockings. I put them on and reveled in the feel of the lingerie and the weight of my new breasts. I caressed them with my hands for a minute, and felt a mixture of joy at having them and sadness because I didn’t feel anything when I tweaked the rubber nipples.
“Sit down here and I’ll help you with your makeup,” said Amy, and she led me to her well-stocked makeup table. She chose the foundation, blush, mascara, lipstick, and other makeup and Emma wrote down the selections so that I could buy my own stock. When she was done, she turned me around in the mirror and asked what I thought.
I was struck breathless. The face that looked back at me was feminine and beautiful. The makeup did its job, but remained somewhat subtle. “Jamie, let me show you what I did so you can do it yourself,” and she demonstrated her techniques for putting it all on. None of it was very complex, and given my experiments with makeup over time and what I had learned by watching Emma, I was confident that I could keep the makeup fresh and replicate it in the morning.
“One thing you should know. With most makeup, you need to wash your face clean every night. I know you are on a vacation here and I made sure that these are high quality products. It won’t damage your skin to go to bed with it on for a few nights.” She added, “I can tell that you might not want to pause to wash it off before getting what you need in the bedroom.”
Finally, Amy brought me the dress that she picked out for me. It was a light yellow sleeveless cotton dress with a form fitting upper body and light blue sash around the waist. The skirt was knee length and was meant to be worn with a lacy petticoat, which came with the dress. When I put it on, the skirt flared out gently, the dress fit beautifully. The petticoat made the dress flare out gently in a late-50s sort of way, but not so much as to look like a costume. It made me look like someone who was enjoying wearing a slightly unusual, but still attractive, dress while away from home.
“I think you will look pretty and sexy in this, but not too provocative. Most people will think you are a woman, but those who know what to look for will see you as a crossdresser who is very well dressed. I’m going to switch out your shoes to some pumps; I don’t think that the woman who would wear this dress would wear sandals while wearing stockings.” Amy gave me some light blue pumps with a 4 inch heel; the shoes matched the waist sash on the dress. She also picked out a purse in a similar color.
“Spin around a couple of times, Jamie,” said Emma, “I want to see how he skirt flies out when you spin.” I did as she said. The spinning felt flirty and wonderful, and the petticoat felt light butterfly wings on my legs. I was in heaven.
Amy put a pink bow in my hair that complemented the colors of the dress but didn’t match directly. “Ladies, I think you are ready to go out and see how lucky you can get in Las Vegas,” Amy was beaming as she spoke. “Jamie, you look wonderful. I hope that this is all you hoped for.”
I thanked Amy profusely, trying hard to keep my voice soft and feminine. Emma stepped back and looked me all over. “Jamie, you really look wonderful. I am so glad you told me you liked to wear women’s clothes. You were meant to look like this, really. I love you so much.” She actually gave me a little round of applause, as I curtseyed in response to her complement.
Amy said, “Emma, I want to show you one more thing. Jamie, please go ahead and lift up your skirt and push your panties down to your knees.” I didn’t know what was going on, but I did as she was told. My panties were on the outside of my garters, as Amy had showed me, so that I could take them off but keep the stockings on for sex. I lifted my skirt and exposed my penis cage.
Amy continued, “It is of course up to you, Emma, but one feature of this petticoat is that it covers up the bulge from the chastity device. By the way, let me complement you on taking charge of Jamie this way—I’ve noticed that she immediately does whatever you want her to do. I imagine there are millions of women who would like to see that from their husbands.
But what I meant to say was that the petticoat will also largely cover up her penis if you take it out of the cage. Because it is pretty small and the waist of the dress is well above Jamie’s hips, there will only be a small, um, tent if it gets hard. Nobody but the two of you will know that her dicklet is standing attention under the dress.”
“I see. Thanks for the tip. It might be fun to see how this works,” Emma said.
After confirming what time we would be back tomorrow, Emma and I departed the Just You studio. Amy had called a cab for us, and we went back to the hotel. When we arrived, Emma made a suggestion. “Jamie, why don’t you go to the bar and have a drink while I go up and get dressed. You should sit at the bar and see if anyone tries to hit on you—it will be fun.”
“I don’t know, Emma,” I said, starting to complain that I wasn’t ready to be alone en femme.
Emma cut me off, “Shut up, Jamie. I’m not asking. I’m telling you what to do next. You are in no position not to do what I tell you.”
I retreated and said I was sorry. I really was. I felt a wave of regret come over me at not obeying Emma’s wishes. I turned and headed to the lobby bar, and Emma went to the elevator. I did my best to glide across the lobby in my heels. I had long dreamed of arriving at a luxury hotel dressed as a woman and walking across the lobby feeling beautiful, sensing that eyes were on me. Now I was here, and it really did feel wonderful. I heard the ruffle of my dress and the click of my heels, and I thought I saw the gaze of some men as I made my way to the bar. I smiled to myself, batted my lashes, and felt my face flush with excitement.
Girls’ Night on the Town
I finally reached the bar, and felt like I was floating. It was still early evening and the bar was dimly lit. There was a small combo playing jazz standards with a nice looking middle-aged woman singing. The slow music set just the right mood and there were few people in the bar as I found a seat at the end of the bar. I smoothed my dress as I sat down and slowly crossed my legs. As I arranged myself, I raised me dress up to my knee because I liked to see my stockinged leg.
“What would you like, miss?” asked the bartender. He gave me a big smile and I could feel myself blushing. I ordered a cosmopolitan—it seemed like the kind of drink that a girl in Vegas would have. When the pink drink came, I took a big sip and batted my eyes as I felt the alcohol start to take effect.
Just then, a man came and sat in the stool next to me and said, “Hello. I couldn’t take my eyes off of you when you walked into the hotel and I just had to come over and introduce myself. My name is Wayne—how are you? May I buy you that drink?”
I couldn’t believe it. I was out in public dressed in women’s clothes for the first time and a man was hitting on my already. I looked at him and saw that he was a white guy in his mid 50s or so, with a nice suit, open collar, and short salt and pepper hair. “Hi, I’m Jamie,” I said.
Wayne was nice. He wasn’t all that confident, which I appreciated because I was so nervous. If he detected that I was a man, he never let on. We chatted about what we liked about Las Vegas, where we were from, and other small talk. He was a lawyer or businessman—obviously successful from the cut of his suit—and was in Vegas for a conference that had just ended. He was staying on for a couple of days to “see what happens” as he put it. He ordered me another drink, which I loved. I told him that I was here for a weekend with my girlfriend—meaning Emma—and that I was waiting for her before we went out to dinner.
He told me he stayed in the hotel and that he’d like to see me again. He asked me my room number, and I told him that I didn’t feel comfortable sharing that with him this soon. He said that he understood, and wrote down his room number and cell phone on a napkin, telling me to call him if I wanted to get together. With that, he told the bartender to put the bill on his room tab and gave me a hug and kiss on the cheek. As he did that, he whispered, “you know, you really look wonderful.” I felt like I was in heaven.
Emma walked in just in time to see Wayne kiss me on the cheek and see him walk away. Emma gave me a big smile. “Nice work, Jamie. Play your cards right and you can get men to buy you drinks from this time forward,” she said. “Or at least until the end of the weekend,” she added with a wry smile.
Emma looked wonderful, and much different than she had looked when she went upstairs. She wore a short blue dress that I hadn’t seen and sparkly blue open toe high heels. She must have known that she was going to wear those clothes, because her toenail polish and makeup highlights matched. In general, she looked like a cougar on the hunt for some young men to fuck. Her look contrasted with mine, because I looked more sweet than lusty in my white and pink. I probably looked like a suburban housewife on vacation wearing her most attractive dress, but unused to nightlife.
I also noticed that Emma was wearing an ankle bracelet on her right leg and toe rings on the second toes of both of her feet. I knew that this was a signal of a “hotwife” who was open to banging men other than her husband, especially black men. I didn’t know if Emma knew this, too, or if she had just added this to her look.
“Emma, you look wonderful. I don’t remember when you looked so sexy,” I said. “But . . . uh . . .do you know that what you are wearing on your feet is a signal? It says that you are looking for men to make love to.”
“You are so silly. It should say that I am looking for some black cock to FUCK,” she said. “If I want to ‘make love’ I have you. If I want to get fucked by a real man who will make me cum over and over and leave me satisfied, I have to look elsewhere, don’t I?”
I felt that intoxicating wave of humiliation that always excites me. I had to admit that she was correct but I hadn’t thought that sex with others is what we were looking for on our vacation.
“You look so cute when you are being submissive,” she giggled. “Don’t worry, Jamie, I’m not on the prowl for dick tonight. But I thought it would spice thins up tonight by inviting hot guys to come and talk to us. Tonight, we are two girlfriends on the town in Las Vegas—and when girlfriends go out, they like for men to hit on them, regardless of where it goes after that.
”Also, you know how black guys get me excited, so I thought it would be fun for you to spend some time with some of them, too.”
I felt relieved. But did I feel a little disappointed as well?
“I have a great night planned,” she said. Let’s have another drink here and then I have reservations for dinner over at the Venetian. We can just relax and enjoy some girl talk—you’ve earned it. Then let’s see what happens after that—this is Vegas, after all.”
That sounded wonderful to me. I was definitely feeling the drinks, but I enjoyed the opportunity to be a girl with Emma. I was almost done with my second cosmo when Emma ordered two more. She then turned to me and said, “I want you to go into the ladies’ room and take your cock cage off. I think you deserve to have your little dick free under those skirts.” I didn’t know what Emma had in mind, but I was grateful for the chance to take off the chastity device. Emma took the key off her necklace and handed it to me, telling me to take her purse with me and to have my cage in it when I came out of the bathroom.
I did as she told me, and couldn’t believe how good it felt to be free of the chastity device. The combination of the silky panties and the frilly petticoat under my skirt felt like heaven as I walked back to where Emma was sitting. As if on cue, two black men came up to us. “Hello, ladies,” said the taller one in a velvety deep voice. “My friend and I are going to buy you those drinks.”
Emma turned and smiled. She looked the two men up and down as if savoring a beautiful piece of art. “Thank you so much,” she said with an open smile, “we would love that.” She introduced us and we learned that their names were Balvin and Jerome. They were both in their 40s or early 50s—it was hard to tell—with shaved heads and muscular bodies. Both were well over 6 feet and Balvin was a little taller than Jerome, and was clean-shaven. Jerome had a well-trimmed goatee and had an intense, confident look about him.
“You really smell wonderful,” Emma said to Balvin. Placing her hand on his tricep, she leaned into him and took in a long breath through her nose. “ I love your cologne. Jamie, lean over hear and breathe in how good Balvin smells,” Emma pulled my arm over until I was pressing against Balvin, who put his arms around each of us. I couldn’t help but notice that he did smell intoxicating.
“You are smelling my own special blend, girls,” Balvin said. “I wear Calvin Klein’s Obsession for Men. I know that it is kind old fashioned these days, but I started using it in the 90s and never stopped. I also use cocoa butter every day, so you are smelling the mix of the two things.”
“MMMmmm. It is wonderful, but you are selling yourself short. You also have your own sexy man smell mixed in there,” said Emma, “The scent is pushing all my buttons. I think you need to dance with me so I don’t fall down.”
Emma took Balvin’s hand and led him to the dance floor, giving me a wink. The band was playing a slow jazz number, and soon I say her wrapped in Balvin’s arms swaying to the music. Jerome had been quiet up to now, but he took my hand and said, “I’m not standing here with them out there. We’re dancing too,” and he led me to the dance floor before I could think of anything.
We got to the center of the floor and he took me in his arms and held me close. He was a little taller than I am, and I felt the whiskers of his goatee against my face. His arms were like twisted steel and his body was rock hard. He smelled as wonderful as Balvin, but with different cologne. “Relax, baby—you are all tense. Just sway to the music,” he said.
He was right, I was tense. I closed my eyes and tried to give myself over to the moment. As I did, I felt Jerome’s hand slide down to my right butt cheek and he pushed me against him. I felt his cock against my hip—the first time I’ve ever felt another man’s cock against me. He wasn’t hard, but he felt like a firm sponge. I couldn’t tell how big he was, but I could tell he was thick and meaty.
I felt my own dick start to stiffen and I tried to roll my hips back. Jerome pushed me harder against him and said, “Don’t pull back, baby. I wasn’t sure at first, but I know that you have a little surprise under your frilly skirt. I’ve always had a thing for white chicks with dicks, so you are with the right man tonight.”
I didn’t know what to say. I had been locked in my cage for days, and I had a huge amount of sexual tension that was trying to get out. I started to breathe harder and get more and more excited. Jerome pressed me harder against him and started to grind against me as the band started a new, sultry tune.
I was just starting to respond when Jerome spun me around and brought me back against him with his arms around me and my ass pressing against his crotch. I now felt his swelling cock pressing between my ass cheeks while his hands roamed across my stomach and down against my dick. He took one of my hands and put it on his cock, pressed between us. “Feel what you are doing to me, baby. I can feel that your little sissy clitty is even more excited than I am. Fortunately, your skirt covers up your little tent pretty well, so grind that ass against me. That’s it.” I felt overwhelmed by my instinct to get fucked, like I was a bitch in heat rubbing my ass against anything with a penis.
From my half closed eyes I saw that Balvin had both his hands on Emma’s ass and they were grinding away while engaged in a deep kiss. I also saw her whispering something that made him smile and nod. I felt a mixture of jealousy and gladness that she was enjoying herself as I closed my eyes again and tried to merge my ass with Jerome’s crotch. His hands were strong and slow as they moved up and down my sides and I reached my free hand back over my shoulder and caressed the back of his neck (I silently thanked the Pilates and dance classes for improving my range of motion).
When the song ended, the band took a break and Emma and Balvin came over to the two of us. I felt the spell of the moment slowly fade as Balvin said, “Jerome, these lovely ladies already have plans and we need to get going to that other thing.” Jerome looked quizzical, but Balvin said, “You remember—that thing we have to do,” and gave him a conspiratorial look. Jerome looked disappointed, and I just knew that he had expected to get some sex from me (I was kind of disappointed, too).
“It was wonderful to meet you guys. I love meeting beautiful men like you,” Emma said. She gave Balvin another kiss on the lips and a kiss on the cheek to Jerome—I couldn’t tell, but it looked like she whispered something to him quickly. Both me kissed me on the cheek and Jerome gave me a squeeze on the ass. “See you around, baby,” he said with a grin as he moved away. Balvin and Jerome where chatting quietly about something and chuckling as they walked away, but not before looking over their shoulders at Emma and me. “Wave, Jamie—they like you. You never know—maybe we will see them again,” said Emma.
I was flustered, but we gathered ourselves together and went to the main entrance and got in a waiting cab to the Venetian. “You are going to love this, Jamie. The Venetian is amazing and there will be lots of eye candy—of all varieties.
“By the way, you are quite the mynx as a woman. The first time you go to a bar dressed like your sissy self you get a potential sugar daddy to buy you your first drink, and then in no time you are grinding away with a fine piece of chocolate. I think you like being a woman, don’t you? Is this as good as what you dreamed about?”
I had to admit that the experience so far was better than my fantasies. I also said that I think I understood why Emma liked black men. “The contrast of his skin against mine, the feel of his body, the way he talked were all really exciting,” I said.
“What about his dick? You didn’t mention that. I could feel that Balvin had a nice one—at least twice the size of yours—under those pants. I saw you groping Jerome’s—what do you think?” I was embarrassed and didn’t know what to say. “Come on, Jamie—dish. Don’t you know that us girls always compare their mens’ cocks when the guys aren’t around? Believe me, all the girls in your exercise classes know what you are—or rather, are not—packing.”
I blushed. Could that be true? Anyway, I said, “Jerome felt sooooo manly. When he twirled me around, it was like I weighed nothing and he could control me however he wanted. I could tell that his cock was really big. I don’t know how big, but it was very thick in my hand and seemed a foot long when he pressed it against me. Maybe bigger than any of our sex toys.”
“Well, its good that I broke it off because he might have broken you!” she said with a twinkle. “Balvin made me totally wet, but I didn’t want to ruin my plans for us tonight. Congratulations on joining the ‘I Love Big Black Cock’ club.”
We reverted to small talk for most of the ride until getting to the hotel. Emma was right about the Venetian; I loved it. The hotel was painted with a wonderful illusion of actually being in Venice, and it felt dreamy walking through the room that seemed like St. Mark’s square. The crowed was attractive and upscale, and I saw many sexy women walking around, including a number of apparent cougars. The average age was a little older than I had observed in other places, and there was little of the college/early 20s feel that seems to hold in parts of Las Vegas. As a result, the men were mostly well dressed in nice pants or suits, well groomed, and possessing the confidence that comes with the years.
It was about 8PM when we got to the quiet northern Italian restaurant that Emma had selected. The place was just right for us. Emma had pre-ordered pink champagne cocktails for us, and the tall Latin waiter brought them to us right after seating us. The lighting was soft and the background music was at just the right volume to keep conversations private without being too loud. Both Emma and I ordered an appetizer and salad for dinner, accompanied with an expertly paired bottle of wine. The dinner was relaxing and intimate. It was if Emma and I had placed the power relationship to the side and were just enjoying being together as a couple of girls on the town. Our table had a view of other diners and people walking through the hotel outside the restaurant, and Emma and I talked about what the other women were wearing, how the men’s butts looked, and what we supposed different people were off to do later in the evening. The waiter was a fine looking and flirted with both of us, although he was clearly more attentive to Emma—and Emma clearly enjoyed it.
The evening would have been perfect if it had ended there, but this was Las Vegas and we weren’t about to end things at 10PM—the time it was when we were finishing our Sambucas after dinner. I was fully enjoying myself as Jamie; I felt relaxed, happy, and amazingly comfortable. This was true even though I was wearing a very tight corset and this was my first time in public in a dress or heels (though it was far from my first time with a panties and bra under my clothes!). Just as I was reflecting on how right everything felt, Emma said, “Well, are you ready?”
“Ready for what?” I asked.
“For what comes next, silly. Our big Pimp & Ho night is tomorrow, so don’t you think that we need to keep getting ready?” I wasn’t sure what she meant—I mean, haven’t I been getting ready for months?
“I mean that we need to keep getting ready on the inside. We are both looking hot, so I think we are ready on the outside. But we need to get in the mindset of the sex trade, don’t you think? I thought we’d ease into it by going to a strip joint tonight. We can get comfortable with exchanging money for thrills. What do you think?
“I don’t know, Emma. I hadn’t anticipated that kind of thing.”
Emma’s mood immediately changed. “How many times do I need to fucking remind you? What you think isn’t important. I was being nice to you by making conversation, but your place is not to disagree with me. I’ll do what I want, and I’ll do with you what I want or I will expose you right now in front of everyone. How do you think that will go over?”
The reminder stung, but I felt my dick get hard. Part of me—the deep down part of me—craved being put in my place. “I’m sorry, Emma. You are right. I’m ready to do whatever you want.”
“Damn right you are.” Just then, our waiter came over to complete the check transaction. Emma looked at his nametag and said, “Hector, thanks for your service tonight. I had a wonderful time, as did my husband here. Let me ask you, could you tell that this panty-wearing bitch here was actually a weak, tiny-dicked failure as a man? Or did you think she was a woman?”
Hector was unflapped, as though he had seen this situation many times. “Ma’am, I wasn’t exactly sure. My complements to you, because she looks good. I could sense that something was a little different, though.”
He went on, “Actually, I was hoping that she was a guy in drag. I’m gay and I love to hook up with femme men who play the woman in the relationship. That’s why I came to Vegas—there are lots of sissy types here. Is she available?”
Emma smiled, “Well, Hector, I don’t know. Maybe she will be.” Emma wrote her number on a napkin and gave it to him, “We are going to the Pimp & Ho party at Paris tomorrow; call us after that and maybe we can work something out.”
Hector moved closer to me, so he was standing with his crotch very close to my face. I could feel the heat coming off of his body. He said, “Maybe I’ll see you at the party.” He grinned, “You know us gay men can’t resist a good costume occasion,” he turned to me, “You aren’t the only one who gets to dress up, honey.” He bent down and gave me a quick kiss on the cheek, “It was nice to meet you, Jamie—maybe I’ll see you tomorrow. By the way, I love your necklace.” I realized he got my name from my necklace. I couldn’t tell if he saw the “Littlecock” part, which was partially covered by my clothes. Had the other guys tonight seen that, too? I had forgotten I was wearing it.
I was speechless. Although I love to play with fake dicks with Emma, I didn’t think of myself as gay. However, I have now spent this evening flirting with two men at Paris and was now involved in possible plans with a tall gay Latino. This was well beyond the public crossdressing fantasy I had thought about before.
Emma said, “You are on fire tonight, Jamie. Just wait until you see the men at the club we are going to.” She checked her phone for a text; “The limo is outside waiting for us—let’s go.” I gathered myself and followed her to the main hotel entrance, where we got in a black limo.
Off to the Club
“You ladies look like you are ready for a good time. Do you still want to go to the Palomino?” the driver asked.
“Let’s go,” Emma said. “I’m ready to see some hot man-ass tonight.”
“Great! They have a big show tonight. Married women like yourself seem to really like to cut loose at it.” He must have noticed that we were both wearing wedding rings.
Emma explained to me that the Palomino is a club that she had read about online. It was in a sketchy part of town, but was reported to have very good-looking men in their lineup. “Especially black men,” she said, with relish.
We got to the club and I was nervous because the area did seem dangerous. Getting into the club involved passing some bouncers that looked more like criminals and passing by some bulletproof windows. The club had two sides—one with female dancers and one with male dancers. We moved to the one with the men and ordered some vodkas. Emma also ordered us a couple of shooters called, “screaming orgasms.” Before drinking it down, she looked me in the eyes and said, “I could really use one of these. I don’t think you have ever seen one of these before.” Then she winked at me and drank the shot right down. I followed her example.
As my eyes adjusted to the dark club, it looked like they were experiencing a break between dancers. The club was about half full but lots of women were starting to stream in. The crowd included a couple of bachelorette parties, and the girls were all excited and ready for some sexy fun. A dancer came out and started to work his magic on stage. He was a tall, muscular black man who was dressed in a faux-military uniform that he immediately started to take off. His second song was a slow jam, and he stripped down to a thong by the first chorus as he worked his way around the stage. The women in the crowd were not at all shy about shoving dollar bills into his thong as he worked his hips like he was slow-fucking the air. He had a big bulge and at the end of the song he ripped open the Velcro sides of his “costume” and started moving around the stage to a more up-tempo song with his cock swinging back and forth. As he would pause near women in the audience, he’d let their hands roam up his legs and hips—obviously the club had a loose policy when it came to touching dancers. Some women got bolder and felt his cock and balls, and he was hard by late in the song. You could sense the building excitement in the crowd as all eyes focused on that cock, which was perhaps the largest I had ever seen in person. It was 8 or 9 inches long, thick, and hairless as the dancer obviously kept himself free of all hair. His whole body glistened with baby oil under the lights, and the final song of his performance was spent walking around the tables in the audience as women shamelessly stroked his cock. The brides-to-be enthusiastically stroked the cock, and I wondered if they were thinking about what they were likely not going to see any more of after they married.
“Look at how these women are going crazy for that guy,” said Emma. “Do you see how many wedding rings were on the women reaching for that guy? They looked like they were starving for what he could offer.” I had to admit that I was struck by how openly lusty the women in the audience were. They weren’t acting ladylike, worrying about their reputations, or acting reserved in any way. It was like there was a collective sense of desire for hot, exciting, unbridled fucking without any constraints. I could almost feel the groupthink take over, overpowering any inhibitions. And I felt it come over me. I wanted to see more big cock, and I wanted my chance to touch it. And I wanted it as fast and as much as I could get it.
Suddenly, the lights flashed and an announcer said that the main part of the show was going to start. It was as though the previous dancer was foreplay designed to excite the women in the audience and the change in lights and music served to jolt the crowd to a higher level of excitement. The announcer welcomed the crowd and promised all satisfaction of the “deepest, darkest” desires. The bridal parties squealed in approval and the announcer called out the brides to be for a special welcome. He then made a point of welcoming all the married women in the audience, telling them that they would finally get what they needed here; the women roared in approval. Finally, after building the crowd to a crescendo, a curtain opened and a lineup of 10 men started dancing. Of the 10, 7 were black, one was Latino, and two were white.
The men danced around the stage and then jumped down and moved through the audience with women reaching and grabbing all the way. The excitement remained high through several songs as the dancers did a number as a group and then individuals took their turns, starting with the Latino and the white guys. The crowd was appreciative, but it seemed that they were all waiting for something.
A female announcer took to the stage, asking the women if they were having a good time and a couple of questions about were people were from. Then she brought the two brides-to-be to the stage, who took seats on either side of the stage while wearing little bridal veils. She then asked the girls if they were excited about getting married (they were). Both the brides were white, and the announcer asked the girls if the grooms were also white (they were). Then the announcer started teasing the crowd. “What do you ladies want to see?” she asked. There was little response.
“Come on, ladies. You know why you came to the Palomino. What do you really want to see?”
Someone shouted, “Big Black Cock!”
“That’s it,” said the announcer. “What do you ladies—especially you married ladies—really want?”
The crowd roared, “Big Black Cock.” Emma was shouting it.
“Damn right,” said the announcer. “There is nothing else like it.”
Soon the whole crowd was chanting, “Big Black Cock—Big Black Cock—Big Black Cock . . .” I was chanting all along, and I have to admit I meant it. I wanted it.
The announcer calmed the crowd down and then turned to the brides. “All right now, you heard all these ladies. They know what they want. Now, you are both getting married to nice white men this weekend. Let me ask you—what do you really want?”
“BIG! BLACK! COCK!” They each responded, to the applause of the crowd.
“Well then, you are going to get it!” With that, the curtain opened and four big, muscular, black men emerged. They were already naked. The whole crowed seemed to scream with excitement and gasp in amazement at the same time.
The men immediately focused their attention on the two brides, who each found themselves with two big swinging semi-hard black cocks grinding one either side of them. One of the brides—a young woman with short red hair, glasses, and the look of a schoolteacher—looked embarrassed initially. She was blushing and held her hands over her mouth. Her eyes kept darting between her friends in the audience—who were shouting encouragement—and the bodies of the men dancing next to her.
The other bride was a good-looking blonde who looked both a little preppy and had the look of a pretty girl who was used to the attention of men. Although she looked as though she belonged more in a country club than a strip club, she was not embarrassed at all. Instead, she had a big grin and her hands were immediately massaging the legs and stomach of the men next to her. One of her friends yelled, “Sarah—they must have known about your last Spring Break!” Sarah looked back and winked, and then her hands went to the men’s cocks. The dancers moved and thrust to the music like they were fucking her hands. Their dicks immediately got harder, and the mugged to the crowd urging more cheers and encouragement.
The other bride was warming up also. Seeing that she needed guidance, the men whispered encouragement to her and she nodded in compliance. She slowly stood up and found herself sandwiched between the two muscled dancers. One of them picked her up and held her with her legs wrapped around his hips. The second dancer put his cock between her covered butt cheeks and thrust against her. Soon the three of them were moving in unison as her hand reached back and wrapped around the neck of the dancer behind her. Her eyes closed and it was clear that she was getting aroused at the simulated double penetration.
Meanwhile, the blonde was enjoying herself as well. The men guided her off of the chair and set her on her knees on the floor with them flanking her. A stagehand gave one of the dancers a large towel. While the blonde was holding on to the two cocks on either side of her face, the smaller of the two dancers said, “We are going to give this beautiful bride a special treat. However, we can’t show you everything and still stay legal.” Then he gave his partner a corner of the towel and they held it in front of the bride and their cocks so that the crowd could only see the men from torso up, and all there of them from knee-high (or hip high, in the bride’s case) down. It was clear, though, that the bride was sucking their cocks and bobbing back and forth between them. The men gave running commentary:
“There you go, baby”
“Did you see that? She took it all the way down”
“Oh yeah, lick my balls”
“Your husband is a lucky man”
All the while, the crowd was hooping and hollering. Many were yelling, “give ME some of that” or “bring that beautiful cock over here.” I was amazed at the total lack of inhibition in the women. They were totally and completely consumed with what they were seeing. All the things that one can read about women not being as visual as men or being more reserved was clearly not true—these women were as bawdy and lusty as a frat party crowd being entertained by a couple of hookers.
This went on for a couple of songs. The bride who was getting dry humped by the two studs looked as though she came from the friction. She had given up all pretense of restraint and let the men feel her tits as she ground against them. She was flushed and breathing hard when she went back to her friend with a sheepish smile.
The men made faces and noises as though they were coming with the blond. When they dropped the towel and she returned to her seat, she wiped her mouth, kissed each of the men on the cheek, and slapped each of them on the ass. For their part, the men’s cocks were shiny and well lubricated as they exited the stage. One couldn’t be completely sure whether she had sucked them off, whether it all was simulated, or whether she was a plant from the club who blew the dancers to keep the crowd fired up. Whatever the truth, the crowd responded as though she was a heroine to them all with loud applause and affirmation.
The announcer came back out and said, “Alright ladies! Who is having a good time??!! Who wishes she had men like this to go home to???” The crowd roared in response. “Who wants some of what these two hot bitches just got?” The crowed roared again. “Well, let’s keep the party going!! Give a big welcome to the stars of the evening, Mr. Thick and Mr. Long!!!”
To the loudest applause yet, two more nearly naked black dancers came out and started dancing to a song with a raunchy beat. They quickly made their way down into the crowd and danced and strutted near the tables. Women were intoxicated with desire for them at this point, and they had their hands all over their bodies. Several women tried to suck their cocks as they came near, and some succeeded.
Emma yelled at one of the dancers—“Over here! Come over here, baby!” The dancer saw her and moved our way, which was near the bar. Emma pointed at me and showed the dancer a $100 bill. “Give my girlfriend here an extra special dance, baby, and I have something for you.” The dancer smiled and placed himself right in front of me. He smelled of sweat and baby oil, and his body was glistening as beads of sweat made their way down his rippling body. He must have been “Mr. Long” because his cock looked to be over a foot in length. Compared to me, he was also Mr. Thick because his cock was as big around as Emma’s wrist.
The beat slowed down and he danced in a very slow, sexy way in front of me. “How do you like it baby? Is this what you are looking for?” He said to me. I nodded “yes,” but felt very awkward and self-conscious.
“You can go ahead and give it a taste if you want,” he said. “You’re friend has paid for it.” I blushed and shook my head, but he took my hand and placed it on his shaft as he started to thrust. I felt his cock get harder and bigger. The male part of me was amazed at the idea that a man could actually charge women to suck his dick, and that they would yell in delight at the chance to suck it. Such a thing was beyond my imagining with my little one.
“She wants to put her mouth on it,” said Emma. “She is just shy. She has never seen a real man’s cock like yours.” The dancer winked at her and looked over to the bartender and held up his hand. Knowing what to expect, the bartender tossed a can of whipped cream, which the dancer expertly caught. He shook up the can and waved it to the crowd of women who where watching him—and me—all around us. They all started yelling, “Yeah. Do it! Go ahead, suck it! Suck that cock!”
The dancer took the whipped cream and sprayed it on the head and shaft of his dick. “Come on, baby. Open up. Dessert time!” he said. I looked at Emma, who looked at me with a serious expression and nodded with a movement of her head that was clearly a command.
I opened my mouth and licked up some of the cream. Then I licked more and started licking up and down his shaft. The licking was automatic—just liked I’d practiced at home with the dildo. “Damn, girl—you are good that this!” I heard him say. I then opened my mouth and took the front of his dick into my mouth. I thought about trying to deep throat him, but after a couple of pumps he pulled his cock out and lifted it up. With his other hand on the back of my neck, he directed my mouth to his balls as he laid his cock on my face. I greedily licked and sucked both of his balls into my mouth as the ladies around me were clapping approval.
“Thanks, honey” the dancer said. “I can’t cum yet though—still need to work the crowd.” He kissed me on the cheek and made his way to another table, along with the attention of the crowd.
Emma, however, was right there with me. “How does it feel to be a real cocksucker now?” she said. “You looked like you were meant to do that. Totally hot, Jamie. You are a natural.”
She then told me that my lipstick was now a mess, and took me to the ladies’ room so that I could fix my makeup. “Hold your purse in front of you, Jamie. Your little dick is making a tent in your skirt. I doubt if anyone would notice, but a girl can’t be too careful, can she?” I looked down and realized that I was indeed rock hard. “You must REALLY like sucking a big cock. Well, I can understand that. I do, too.”
The feelings were rushing over me in constant, confused waves. I was turned on and very attracted to the ebony sex god who was dancing just for me. I was disappointed that I hadn’t felt his cum on my mouth, and I wanted to find a way to satisfy that desire. I was embarrassed at the idea that I was now a cocksucker, and remembered the saying that “it only takes one.” I was amazed at the reality that I was now in a ladies’ room fixing my makeup like it was a routine thing for me, and shocked at how much sucking cock smeared lipstick across my cheek. On the one hand, I didn’t feel like myself—at least the self I thought I was for the previous four decades of my life. On the other hand, I felt like I was totally myself, doing and behaving exactly like I wanted to. I was ashamed that I was being bossed around my wife, but I was also happy and grateful to her for bringing me to this point. I know that, if left to myself, I’d still be wearing panties and jacking off alone to the idea of dressing in public and touching a black cock instead of doing it right out in the open.
Emma said, “I think that is enough of that for tonight. I need you ready for tomorrow, and I think that this was just the right warm-up. If this is the side of you that comes out in a white dress and petticoat, I can’t wait to see the whore side of you tomorrow.” I couldn’t imagine what else could happen tomorrow, as I had already surpassed about all of my fantasies, but by this point I knew better than to try and control or anticipate.
We downed the remainder of our drinks and made our way to the exit, to meet the limo that Emma must have planned to meet us there at the appointed time. It showed me that she really was in control of everything that was happening in this wonderful vacation.
Emma gave the driver directions to take us back to hotel. “Well, that was a big night, don’t you think? I’m going to be thinking of big black cocks all night, I think,” she said with a smile. “And speaking of cocks, or in this case little dicks, I think that it is time to put your little clitty back in its home, don’t you?”
I was very disappointed. I hoped that we would have some sex when we got back. But I knew that she was testing me and I didn’t want to risk getting out of line at this point. It wasn’t really a request. “Yes, Emma.”
“Good girl.” Emma took my chastity device out from her purse and, having me lift my skirt up to my shoulders—put it back on me. When it became time to close the lock, she said, “Jamie—why don’t you do it this time. I like the idea of you locking yourself up for me.” I did the only thing I could—I reached down and closed the lock with a pronounced click. Emma hung the key around her neck again and again, “Good girl.”
She then looked at her watch. “Oh look—it is well after midnight. Today is the day of the Pimp & Ho party. So instead of ‘good girl’ I guess I should say, ‘good little whore,’ shouldn’t I?” I agreed.
Jamie the Whore
She went on. “Because that is what you are today, isn’t it? You are a whore. A bitch. My little whore. Aren’t you?” I nodded. “Say it, bitch. Say what you are.”
“I’m your little whore.”
“That’s right. You’re not a man. You’re not a woman. You’re not a crossdressing sissy anymore. You are a whore.
“I’m not playing. We came out here for a Pimp & Ho party, but I decided long ago that this was not going to be just playtime. Lots of people are going to dress up and look comical, letting out some of the inhibitions that they don’t let out every day. That isn’t what we are doing here. You are my fucking whore, at least until the morning after next. Do you understand?”
“Yes. I’m your whore.”
“I doubt that you do understand. Whores are stupid. But you are going to understand by the time this is done.” I was amazed at how Emma’s mood had changed. Earlier, we had been two girlfriends out for dinner and having a sexy time at a strip club. Emma had become a little dominant there, but now she was more so than I had ever seen.
“So I am going to start making you understand. At their core, what do whores do, Jamie?”
“They have sex for money.”
“That’s only part of it. No, they give themselves over to others. They sell their most intimate parts for money, taking whatever they can get. But then what do they do? They give the money to their pimp or madam. They really give over their whole selves to the pimp, who makes all the decisions. The pimp or madam takes total charge of the whore—tells the bitch what to do and how to do it.
“The whore no longer owns anything. Not money, not possessions, not even her own body. It is all at the service of the pimp. And when the whore steps out of line, the pimp punishes her. Severely. All the whore has to do is provide money to the pimp in whatever way the pimp wants. The john rents the whore, but the pimp owns her. Now do you understand?”
“I think so,” I said.
“THAT is the fucking problem. Stop trying to think, whore. And you don’t understand, so I am going to tell you.
“You are a whore today. In fact, you have been my whore for a long time and you didn’t even know it. You have been working hard for the last 20 years or so and you have done a reasonable job of building up the family savings. We have a nice house, and we have a secure retirement. We have enough to do nice things, like go on vacations to Vegas.
“I thought that this is how things were, too. But now I know it was all wrong. I thought I had married a man, a man who would love me and who had the ability to take care of me. But then you came home with your sissy confession. And then I became phone friends with Alexa and learned all about what you are really like. And I decided that if you wanted to be a whore, then that is what you would be.”
The limo driver was shaking his head. “What are you laughing at?” asked Emma.
“I would never let my wife talk to me that way,” he said.
“Of course not. That is because you are a man. I didn’t marry a man—I married this little bitch here. And now I am going to tell her how much of a bitch she really is. Keep driving until I am done, and if you have 50 bucks Jamie will suck your cock.” The driver declined, thank God, saying he was going home to fuck his wife when he gets home.
Emma told me, “So I decided that if you were my whore, then I was going to get what I want. Think back, Jamie—when have you spent money in the past couple of months?”
I had to admit that I hadn’t spent anything except for getting gas when going back and forth from my exercise classes and appointments—Emma had taken care of that. “That’s right. You know why? You don’t have any money. I have taken everything out of our joint accounts and placed it into my own name. Everything that I could get signed over is signed over to me. I left you some money in the joint account, and we have been using that for everything leading up to this trip—the travel, the meals, the spa, my clothes—everything. They way I figure it, this trip will drain the last cent you can get to.”
I couldn’t believe my ears. I had spent a career building up a nest egg. I thought that I was actually done with the rat race. If I wanted, I could retire with Emma now. I looked forward to the rest of my working career as adding icing to the cake. Now Emma was telling me that I didn’t have anything.
“Of course, I couldn’t control everything. You still have some retirement accounts in your name and the house. But I refinanced the mortgage and took out all the cash I could and spent the shit out of your credit cards, so you also have a ton of debt that pretty much cancels out anything you may have.” I was reeling. Could this be true?
“So if you think about it, you have been my whore for 20 years. You worked your whole life up to now just to give everything you earned over to me. And you aren’t done. You are now really my whore, and you better get me my money.”
Emma took out a couple of papers from her purse. “ I know that there is still a little part of you that is trying to think your way out of this. A part of you that still thinks that you control part of this, or that it can’t be real. So look at this and let it sink in.” She handed me a letter from our financial advisor, Randy, and copies of our main account statements. They showed very small balances in all the accounts with my name on it, and the letter stated that Randy had executed all the trades and transfers of our assets to Emma’s accounts, according to Emma’s wishes. I knew that Emma had signature authority on our accounts and a blanket power of attorney from me, so I knew that she had the ability to do all of this. It was real. I had worked all my life, gone to school, paid off loans, invested wisely, grown my wealth, almost joined the top 1%.
Now I had nothing and Emma had everything.
“That’s right, Jamie. I see that it is sinking in. You have nothing. Your accomplishments have led to nothing for you. You thought you were working for us, but you have been working for me. I have everything, and you are nothing but a whore. Say it.”
It came easier than I ever could have imagined. “You have everything, I have nothing. I am nothing but your whore.”
“That’s right,” Emma said, looking out of the window. “Now you have only one job—to please me. A whore lives for the approval of her pimp or madam. That’s all that matters. So please me, Jamie, and I’ll take care of you.” She didn’t have to say the second part—displease me and I’ll throw you away like a piece of trash.
Up to now, every pain and humiliation had been part of a whole fantasy scenario. I had been grateful to Emma for setting it all up—grateful for making my fantasies come true and pushing them even farther than I imagined. I loved her for it and I was excited about the time we were sharing. But up to now it was, well, pretend. I always had the idea that we would go back to something like we had experienced before. Sure, I’d now be open with my sissy tendencies and we would deal with some new developments, but I imagined that they would bring us closer. I thought the “Pimp & Ho” party would be a spicy climax to this fantasy. But now things had suddenly become real in a way that I hadn’t anticipated. I wasn’t playing whore, giving a rest to the stress I feel from making leadership decisions at work every day. Emma was right, now I really was a whore and completely at her disposal, regardless of what happens after the next 48 hours.
“You always thought you were so smart, Jamie. But all along you have become nothing but my whore.”
We sat in silence for a while as the limo drove down the Strip. Emma signaled to the driver to take us to Paris, and a doorman opened our door when we pulled up. As we got out, the driver said to Emma, “Can I take a rain check on your offer?”
Emma said, “You bet, honey. Jamie will give you a blowjob anytime you want.” I was speechless. I just followed her into the hotel and up to our suite.
As we entered our room, I could see that things were different from when we left. There was some unfamiliar luggage in the place, and some used liquor glasses.
“Is everybody here?” Emma called out.
From the second bedroom came an answer. “You bet, baby. Give me a sec.” It was a man’s voice. I’d heard it before.
Walking out of the bedroom was a black man. I recognized him as Darrell, the limo driver who had taken us to the airport from our home? What is he doing here?
Another black man, much younger, also came out of the bedroom. I recognized him as one of the men from our gym back home, part of the weight lifting group that Emma hung out with. Then I realized that I had seen Darrell there, too.
Without even looking at me, Darrell came up and gave Emma a deep, opened mouth kiss. “I missed you, baby,” Emma said.
“Did you miss me, or did you miss this?” he said with a smile as he grabbed his crotch.
“A little of both, I guess,” Emma said.
The other man came up and gave Emma an equally big kiss, accompanied by a squeeze on the behind. “I hope you missed me, too, because I definitely missed that nice round ass,” he said.
“You know I need your cock, too, Edward,” said Emma.
“I hope you both had a good trip,” said Emma.
“It was fine. The upgrade to first class was a nice surprise. I think that the stewardess wanted to fuck Edward. We should probably thank Jamie for the flight,” said Darrell.
“You don’t thank Jamie for anything. Jamie is my whore now, and it is her job to please me and whomever I tell her to please. She should be satisfied with that and doesn’t deserve thanks. She should thank you for the opportunity to do something for you.”
Emma turned with her arms around the two men, one around each man’s waist. They were all smirking at me. “Jamie, this is Darrell and Edward. You should recognize both of them from home. You just paid for their trip out here to be with me. And you paid for their room, their drinks, and anything else they want while they are out here.
“You know that I like black men. Well, the fact of it is that black men like me, too. It has always been that way. They tell me it is because of my ass. So you might as well know now—I’ve been fucking Darrell since before we got married. You don’t think that I could be satisfied with your little dick after the fucking I was getting when I was single, do you? I mean, you’ve been dancing with some black men, watching some fine black men at the club, and you were even sucking a black man’s cock earlier tonight. So you must understand. You just can’t compete with the way that Darrell fucks me. His dick is huge and he knows how to use it—he makes me cum every time.
Edward here is a friend of mine. He’s a cop back home, and I started fucking him a couple of years ago. I was speeding to get to Darrell’s once and he pulled me over. I sucked his dick, so he didn’t give me a ticket, and we have been at it ever since.”
“That’s right. I’ve never seen a woman that loves fucking a black cock more than Emma here,” said Edward. “She has some good pussy, and is always ready for more. That’s why I bring my friends around, because she is more than any one man can handle alone.”
All three of them chuckled at that. Emma said, “Darrell and Edward know all about you, Jamie. Lift up your skirt and show them what you have under there.” Ashamed and confused, I did as Emma told me, and they all had a big laugh at my little dick in its cage.
“I wasn’t sure whether to believe you, Emma,” Darrell said, “but she is as pathetic as you described. I’m glad we found each other, or you would be a very unhappy woman.”
Emma told me to make drinks for the three of them and wait by the bar in the suite until told what to do. Emma and the men sat on the couch and chatted about the past few days. Emma asked after Susan, the woman from my barre class who had complemented me on my lips. Darrell said, “She will be here tomorrow. She is looking forward to the party and seeing what you have done to Jamie here. I think that she is totally ready to fuck some young dudes in Vegas.”
“That’s my Susan,” said Emma. I couldn’t believe it. Susan, my friend from my exercise class, was coming. I had enjoyed girl talk with her and thought of her as close. Now it turns out that she knew all about me, and probably knew about me all along. I wondered who else from our lives back home was in on the not-so-secret secret.
After more talk, Emma turned to me.
“Jamie—go into our bedroom and put on the nightgown that I have put in the closet for you. I also want you to wash off our makeup and get ready for bed. You have 5 minutes, and then you are going to sleep out here on the couch.
“Darrell and Edward are going to fuck the shit out of me in our—I mean, my—bedroom and then we are going to sleep together there. They have the beds in the other bedroom and I don’t want you messing the sheets up for them, so you need to sleep out here in the living room on the couch. It is too bad that this place doesn’t have maid’s quarters, but this will have to do. Try to ignore the sounds that will come from the bedroom and get your beauty sleep—you have a big day tomorrow and you need to look your best. I, on the other hand, need some real cock in me and these two guys are just the ones to give it to me.”
I was almost catatonic. Like a robot, I did as I was told. I changed and washed, but not without looking at myself in the mirror and seeing a middle aged sissy. Maybe I never was a man, but I certainly wasn’t one now. My wife had been fucking other men for our whole marriage and I never knew it. I knew that she liked black men and black cock, but I thought that was a wistful memory of sex before marriage, not an every week reality.
I came out into the living room and the three of them were half undressed. The men had their cocks out of their pants and Emma’s breasts were exposed. The cocks weren’t quite as big as those of the dancers I had seen earlier in the evening, but they were still huge and thick. I couldn’t help but admire them.
Emma’s panties were off. She came over to me with a glass of water and a pill, “Here Jamie—this is a sleeping pill so that you won’t stay up all night thinking about what is happening to you. Drink it down.” I took the sleeping pill.
“Good job. Now, I have one last job for you tonight. I’m going to bed with these guys and I am pretty sure that I’m going to get my ass fucked tonight. So get down on your knees and lick my ass until I tell you to stop. I need you to warm me up so I can be ready to take a big dick up there.” Right away, I dropped to my knees as Emma bent over the back of the couch. I ate her ass for all it was worth, thinking about how a big cock or two were going to slide up there in just a little while. Was she going to experience double penetration? Or suck one cock while buttfucking the other? I licked away and never wanted it to stop, until I started to feel a little wobbly.
“That is one thing you are good for, whore. You are good at licking ass. You should feel good about yourself for that—you aren’t entirely worthless.
Have a good sleep.”
They went into the bedroom and soon there were loud moans and the other telltale signs of fucking coming from the room. Part of my brain was aroused and struggled to stay awake and listen to more. But the pill took over the rest of my body, and I shut down and fell into a deep sleep to the sounds of my wife screaming at another man, “Fuck me. Fuck me. I love your big cock.”