Jamie’s Story

Jamie's Story

Download Jamie’s Story Part I

March 1, 2014 March Treat Part I
Jamie’s Story
March Treat for Houseboys
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
“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
“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.”
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