Jamie’s Story: Final Feminine Preparations

Final Feminine Preparations

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.

Departure

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.

“Yes, dear.”

“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.