I found out real quickly that no matter how much money you have, things still don't always work out. She and her husband to be had carefully invited friends and family in a way that fifty couples could be formed. But some could not come and, as she explained this to me when I reported to the penthouse in the hotel, there were six more men than women. I was one of three men that she believed would help her out. If only for one week I would switch to the other side then all events would have the right amount of couples. I struggled a bit although we both knew I wouldn't refuse her anything, but when I saw one of her best friends who would help in my transition to womanhood and who also would be my roommate for the week, I was sold. My cousin, Misty by the way, introduced me to her, Simone, a perfect redhead. I have a weakness for redheads, their long hair, their cute freckles, their tender skin, and preferably curves, like Jessica Rabbit. And Simone had all of that and more.

Her smile was warm, yet breathtaking. She understood my hesitation perfectly but she said "Don't worry, I'll help you all the way. We're gonna have an awesome week and you may not wanna switch back after that". I doubted that, but it was good to know she had my back. She was SEXY, all capitals, in her black shiny swimsuit. Did I mention she had red wavy hair? Beautifully contrasting with her light skin and black one piece. She gave me some swim trunks and showed me where to change. "Do you need help with that?" She smiled when she asked, but I shook my head, I'd love her to help me in my trunks but she'd see my hardon that had quickly developed in my pants. When I came out she had some goggles for me. "You don't want this water in your eyes" she simply said and put her own on. The jacuzzi was nice and deep, almost like a pool. It was just the two of us and we chatted like we'd known each other for years. She was sitting next to me, skin to skin, with some air bubbles blowing through my trunks, ballooning it up. I tried to push it back and she helped me and it was clear that some of the tent in my trunks were not caused by the air bubbles. She laughed "I should have given you latex trunks like my swimsuit, no bubble gets in, you see?" "That's latex?" I asked. She nodded and simply pulled my hand on top of her left breast. Now I've had my share of girlfriends and touched their breasts but this was different. I could clearly feel the weight and size of her breast pulled tightly under the latex, but the wet material added an extra dimension. I rubbed it and I could feel her nipple stiffen under my touch. She moaned "Keep on doing that" while her own hand disappeared in my trunks, where my member was redefining the meaning of stiff. She suddenly moved on top of me, sitting on my lap, so I could rub both her breasts. It was very erotic, with this woman I just met, but it got quickly very uncomfortable between my legs. "Listen", she said, "I appreciate what you're doing for Misty, it won't be easy for you, but you and I will have a lot of fun and a lot of sex. Girl on girl sex. But this thing has to go away for a while, we've something to help you with that. So if you promise to put real effort in being a girl I'll help you now". 

Well, I can guarantee you, if a beautiful woman says that to you, while you already promised you would help your cousin, no way you're going to say no. I simply nodded and the next thing I know is my trunks are gone and she's guiding my dick towards her now exposed pussy, the latex material simply pulled to the side. She sits down on it and with all the wetness down there I slide in without effort despite her tightness. The air bubbles are still massaging down there right on my engorged ballsack. She moves up and down on me while I hold her lips and she suddenly kisses my mouth. Her taste is sweet, her tongue strong and eager, her teeth perfect. I know I'm not going to last long but I can only moan at which she stops her movements and pulls her mouth away. "Jake, I don't want you to be a man trying to act like a girl. I want your mindset to turn female for a week. Your name is Jaclyn now, or Jackie if you like. Can you do that? Be my girl for a week? You'll be with boys, men, during the day, having fun with them, maybe kiss them, maybe even have sex with them. All perfectly normal for a single girl on a nice vacation. No one but Misty and me will know you are really a man, but everyone else will think you're a beautiful woman. And at night you will be my beautiful woman! Can you forget for a week who you really are? Be sexy Jaclyn for a week?"

Her voice was soft, sexy and hypnotic. Her green eyes looking deep in mine. They were beautiful, I could not pull away from them, did not want to either. I would do anything for her I suddenly knew. I would not play Jaclyn, I would be Jaclyn, her Jackie. I would make her proud, make my cousin proud. I nodded. "Yes", I said softly, trying my voice as a woman for the first time, "I will be Jaclyn, your Jackie Simone, I want to be yours". She kissed me again, then she said "Then cum for me baby, like you've never cum before, I want to feel it, I want you".

She moved one more time up and down on me and took me over the edge. I came indeed like I've never come before. My whole body was shaking although it could be her's, since she was cumming herself as well. I could feel it in my toes, my fingertips, my tongue, my nose. I pulled her tight in me and we both rode it out. If this is what it is to come as a woman I may indeed not go back next week. I suddenly tasted her tongue again, licked my own on the inside of her teeth, tasted her lipstick, her toothpaste. My eyes were closed by now while the fire in our bodies slowly dissipated. 

When she finally pulled off me I was limp and that was fine with me. I wouldn't need it for at least a week. Simone got her act together again and she said "Take this in your mouth and breath through it babe, I need you to fully submerge". She pushed a mouthpiece in my mouth which I recognized as a piece of diving equipment and she pushed my head underwater. If it wasn't for her I might have panicked but I simply breathed in through the mouthpiece and out through my nose, with my hands still on her hips. I could clearly see thanks to the goggles and I noticed her vagina being covered again by the latex suit. I suddenly wished I could put my tongue on it but the mouthpiece wouldn't let me. Instead I stroked her between her legs and I could hear her moan even here under water.

This lasted for another ten minutes or so, while it became clear to me what was going on. There must be some chemical in the water. My body had become hairless, I could see it and feel it in my crotch area, it was all smooth there, as was my chest and my legs. I felt my chin and it was smooth and I finally checked the top of my head and I was bald. Funny thing is it didn't bother me. I was becoming Jaclyn so I needed new hair no matter what. It must be easier to do so while I was bald rather than me having my scruffy hairdo. Finally Simone pulled me up and she helped me out. Then she patted me down with the softest towel ever and the feeling was amazing. I had no idea that being hairless could be so erotic. The goggles had not only protected my eyes but also my eyebrows and lashes. But I knew already they would need some work.

Simone had me step in some sort of a bodysuit with short sleeves for my legs and arms and sort of a sleeve for my neck as well. It felt a bit like her latex swimsuit, just softer. I could see what it was going to do, it added an extra layer to my hips and buttocks and what seemed like a female crotch. And I saw decent size breasts hanging from it. While she pulled it up around my crotch area she said "Don't look baby, but this is going to hurt a bit. Do you trust me?" I nodded, giving her a small squeeze on her shoulder. But I still wasn't ready for the pain that followed in my dick and in my balls. It was like a needle that went through it all. But it went numb real quickly and that gave some relief. She pulled up the suit over my crotch area and I saw tears in her eyes, like I had. "Sorry baby, remember I said we had to do something to prevent you from getting hard for the week? Plus we made a connection with the suit, it will actually help you to get pleasure as a woman. Top of the line, Misty said only the best for you". I nodded again, "Don't worry, I understand. Beauty is pain right?" She smiled, "Sometimes" she whispered. My logical mind said I would feel more pain when the breasts would cover my nipples and I was right, not as bad, but still.

Once my head was through the neck opening I looked down and got the first impression of what a woman sees. A pair of breasts sticking from my chest. And when I touched myself between my legs I felt a slit, nothing else. I just wish some of my belly fat were gone, that I was a bit slimmer, everything seemed a bit loose still. But Simone pulled me towards a shower cabin and pushed me in. She turned the water on, quite hot and closed the door. "Relax for a few minutes there Jackie". It was immediately clear what was going on. The bodysuit started shrinking on me, everything became very tight and I could only take small breaths. But my waist slimmed down, belly gone. This was indeed top of the line.

When Simone dried me again I saw a full length mirror and I gasped. My body was female. I had curves. You could not ever think my skin was not my own. I rubbed myself and it felt fully natural. My face needed a bit of work maybe but even that did not look male anymore. She fitted me with a bikini in the same material as her swimsuit and I felt some relief immediately from the weight of my breasts. "Get used to wearing a bra" was all she said with a smile.

She took me back to the common room where Misty was waiting and her mouth dropped while she stared at me. "Sorry to have you go through this, Jake, but you look great!" I smiled, "It's Jaclyn now cousin, but no worries, I quite like it. Are we still cousins by the way?" She shook her head, "No, that couldn't work. I can explain to the family why Jake isn't here, but I can't make up a new cousin out of nowhere. You're Simone's lesbian lover" and she winked at Simone. I was perfectly okay with that.

They both worked on me now. I got new nails on my toes and fingers. A long black wavy wig was glued to my head and they worked on my eyebrows and makeup. It seemed to me that they went for a Latina style which went well with my curves and my height which was never a lot. Simone is probably an inch taller than me. "Will this all come off again next week?" I asked slightly worried. "Sure, if you want to" they laughed, "if you don't mind being bald. But nothing is permanent, at least for now". Not sure what they meant with that last sentence but I was okay for now, I'm Jaclyn, a beautiful woman, and I'm planning to break some hearts. They saw my smile appear on my face and they clearly liked it. Before I knew it pictures were made, of me alone, with Simone and the three of us. My favorite one was Simone and me hugging and kissing in our latex swimwear. "One more question though. What's my last name? Just in case anyone asks?" Misty laughed, she gave me a purse and in it I found a drivers license and passport, both in name of Jaclyn Veronica Gomes, born in Miami with my birthday fairly close to my original.  The passport even had a stamp of me entering the country today. The pictures were quite close to what I looked like right now. When Misty saw the questioning look on my face she simply said "The things you can do when you have some money". The other thing I found in my purse apart from some makeup and a little spray bottle to use for my voice was a few hundred dollars. I've never ever carried that much around.

"Come Jackie" said Simone. "We have a lot of work to do to make you a real woman". "I thought I look pretty good" I replied. But she shook her head, "Sure, but can you do your makeup, pull on a bra, walk in heels, dance as a girl?" They both laughed once I realized what was ahead of me. We both pulled on a very fluffy bathrobe and slippers and went one level down to our room. Still decently sized with a stunning view. Simone took the lead and guided me onto the balcony. "You need a better tan, since you're a Latina. The bodysuit gives your skin a darker look but the rest of your arms, legs and your face need to match. We need to use the sun while we can". She rubbed all areas with some tanning lotion I assumed and had me lie down on my back in the sun, while she stayed in the shadow with her sensitive skin. We talked, a lot. About her mostly but also about me, about us. She explained that Friday night would be dinner with her parents and she would introduce me as her new girlfriend. I wasn't the first she explained and her mom was very critical, so our stories had to be solid. Her full name was Simone Noelle Dubergerac, born on Christmas Day from a French mother and American father. The French name and culture was very important growing up and Simone spoke it as fluent as she spoke English.

She has had boyfriends as well as girlfriends and I could tell she's still not one hundred percent sure where she stands. But it was clear to me that she had better experiences with females than males. I felt lucky actually, I was her girl for the week and hopefully she liked me enough that she would date me as a man afterwards. We kept my story as simple as possible. I had studied at MIT when my parents died in a car crash. Misty had spent six months with me in Boston to help me through this ordeal, which was actually true, although she helped me, her cousin rather than me as a friend. The Caucasian part of my family never liked that my mother married a Hispanic man, and I had no contact at all with them. My dad's side didn't like my mom for that and so I grew up without either family, thus having nothing left when my parents died. I had a full scholarship and when I graduated I was to spend five years at the company that had sponsored my scholarship. At one of Misty's parties I had met Simone and it was love at first sight for me although she had to take care of some loose ends before she was showing interest in me.

It was amazing how easily Simone sculpted my past, mixing true and made up events into a solid history with verifiable moments in regards to her different relationships. She made me remember earlier facts in my life as a girl, my first kiss, my first boyfriend, a destructive relationship that pushed me away from men. I remember names, dates, birthdays and then the start of us dating and becoming lovers. We actually had fun making up some of our shared memories, finding out we had a lot in common. She made sure I turned around often in the sun, my skin turning darker in just a few hours thanks to the lotion. When we were finally done and I looked in the mirror I had a nice tan worthy a Latina. I was a bit surprised when I saw the tan lines of my bikini which were sexy as hell by the way. Simone explained it was part of the skin properties of the very expensive body suit.

Next up was dressing, in lingerie at first. How to put on a bra or take it off, pulling up stockings, taking them off, none of which was easy with my new nails. I practiced with corsets, with girdles, with garter belts, with silk slips and dozens of other items I had no idea about. I could pull my hair in a ponytail with my eyes closed by now, so many times we practiced. I loved trying on all her dresses, she had brought dozens. Our size was similar but I needed an extra inch on my heels to wear the full length dresses. I walked what seemed like hours in higher and higher heels, getting the right sway in my hips, just to turn men's looks at me. I asked why we had to form a couple with guys, if we were lesbians, why could we not be our own couple. But that was a promise to Misty that we both had given. During the day of the wedding and some days after we would act straight and give our men all the attention that they required.

We ordered in salads, I had preferred pizza, but it was clear real quickly that I had to drop some pounds, just so I could breath easier with my tight waist. Simone actually used it to teach me more about maintaining a good figure, the do's and don'ts, things that you never think of as a man. But I liked to learn all these secrets, things that girls somehow learn over time without us boys knowing. And that brought us slowly to the topic of sex. With men. At my age I can't be a virgin, I have had relationships, remember, even a violent one. So I should have experience in pleasuring men, but don't worry she joked, later she would teach me also how to pleasure women. It didn't help a lot to get my nerves under control. I was in a sexy set of lingerie with stockings, garters and the highest heels I could handle. A simple look in the mirror made it clear, my male mind would die to get to spend the night with me.

But my female mind, that I had been working to develop so hard today, was scared shit when I saw Simone with a very realistic strap on. It was top of the line, she explained, the closest to the real thing as possible. Luckily it wasn't super big. She had me smell it, touch it, stroke it and eventually lick it. She explained where the most sensual parts were, how to stimulate it, stuff I had no idea about, I always took it for granted when a girlfriend would get me hard. I had to give her a blowjob, jerking her while doing it, suddenly realizing that it was getting bigger in my mouth. I also tasted some moist on the tip of her strap on. Don't think of it as a strap on, she told me, it's a dick, a penis, a cock, and it will grow bigger and harder and leak precum. "Top of the line, remember?" she laughed when I realized what was happening inside my mouth. I'm a girl now, I kept telling myself over and over again, millions do this to please their man, nothing special. So I concentrated on what I thought would pleasure my guy, thinking I actually have some advantage here, knowing both sides, and she kept growing in my mouth, until I started gagging. You're probably not ready for deep throating yet, she explained, so pull it back a bit so it doesn't hit the back of your throat. It was easier now and I actually felt proud I could make this thing so big that I could taste the precum. I liked the power I had. "Be careful now", she warned, "if you don't stop he may cum in your mouth. Not necessarily a bad thing if you're in a hurry and you like the taste. But you may consider pulling back so he can use it to penetrate your pussy".

It was pretty confusing now. As Jake if I were this hard I wouldn't want to waste anymore time and stick it in her cunt as quickly as possible. As Jaclyn though I had slowly gotten hornier myself, wishing for him to lick my nipples, French kiss my mouth, while slowly entering me. Simone's voice was a bit urgent now and I saw sweat running over her skin. "Let me take you baby, I need you" she whispered. She simply pulled me on the bed under her and she lowered herself on me. She kissed me hard, not slow at all, but I liked it. She was guiding her member into me, though I could hardly feel it as my pussy is fake. Until she hit something inside that hurt. "Sorry babe, I'm taking your flower" she said and pushed harder. By now I could feel something tear and it hurt like hell. I screamed from the pain and I suddenly had tears in my eyes. If my pussy is fake then why does it hurt? And somehow that triggered a subconscious decision. If my pussy hurts it must not be fake, it must be real. I'm losing my virginity to my lover, I see the tears in her eyes as well, so sorry she is. But she's not pulling out, she's getting in deeper. And the pain slowly subsides and I start feeling some pleasure. She's gentle, slowly moving back and forth, and it's feeling better and better. I stopped thinking how this could happen, I just sat back for the ride. I pulled her tighter on me, feeling her deeper in me. She started getting more vocal. "Oh baby, yes baby, I love you". Those last three words made me feel warm inside and I started matching her movements. We got into a rhythm, faster and faster and she started grunting. "Baby, I'm cumming, I'm cumming!" And I came with her, I felt her cum spraying my insides, while my eyes rolled back. My body was on fire, not one nerve unused. I could hear myself screaming, louder than her moans, this time from pleasure. We were one for a moment that lasted forever. I arched my back, easily lifting her up on me, causing her even deeper in me, until finally I no longer felt her spasms in me. I somehow squeezed on her dick but it started shrinking inside me and I couldn't hold on. Finally she slipped out of me, her heartbeat pounding on my chest. I held her tight, didn't want to lose more of her. I felt fluids dripping down my legs and my body finally started relaxing.

"Fuck!" was all she said. "What the hell?" I replied, "What is this thing you put on me? I felt everything!"

"Did you like it?" she asked with a smile. "Hell, yes! But I shouldn't. I felt like a virgin girl!"

"That may explain some of the blood here" and she pointed between my legs. I looked and saw what looked like cum dripping out of me, mixed with blood.

I suddenly was scared. "Please tell me what happened!"

I saw a worried look in her face, or maybe she felt sorry. "I told you it was a top of the line suit we put on you. Remember the pain you felt then in your crotch? It connected the suit to some nerves in your dick and ballsack. Some of those nerves gave you pain when I ruptured your hymen. The rest gave you a sense of pleasure when I got deeper in you. Very high tech! There's some of that in your nipples too". And she put her mouth on one of my nipples and sucked. I gave a gasp, it felt wonderful but the feeling went straight back to my crotch. "Stop!" I cried, "I can't handle that right now". She laughed, "Sorry. You can do that back to me later". And she actually licked her lips.

"Oh my god!" I whispered, "How can I ever go back to normal sex after this?" She laughed even louder now. "Don't get carried away now. I only tried to give you the experience of being with a man. You don't know lesbian sex yet! But if you like that too, there's no reason why you couldn't stay Jackie longer. You're welcome in my life". "You said you loved me" I replied. "Yes" she hesitated, "I'm sorry about that. I let myself go. We created your body based on my own fantasy. And you turned out so lovely. And then we seemed to match as well, I had so much fun talking with you today. I can't expect you to feel the same, sorry".

"But I do! I fell in love the moment I saw you. I didn't think love at first sight could actually happen. But then you turned me in a girl, your girl, and I would do anything to just be with you. When you said those three words I felt so warm and happy inside. I've never felt anything like that before and I don't want to lose that".

She looked incredulous and then suddenly kissed me deep on the mouth. "My mom is so gonna love you!"

The rest of the night was a bliss. We changed in different sexy outfits, played with toys I had never seen in my life even. I think my favorite toy was a double ended dildo as it gave us both the same control. But it didn't feel anything like my own dick, where every thing was centered on my cumming and hopefully my partner would get some fun out of it too. With this toy I could sense her pleasure as well as mine and we worked together to get the most out of it, for each of us. We triggered each other, one orgasm causing the next and I found we could go on and on. I loved the sixty nine position and taste her fluids when she orgasmed. She had more trouble with me as the first part of my pussy has no senses. But when she started using her fingers deep in me she could play me as a piano. The following day she would call the manufacturer of the suit to see if the whole vagina could be made sensitive, for now I was fine the way it was. We finally slept, her body curved around mine, in the sexiest nighties I could find. Made from the same material as her swimsuit that I so loved, just loosely rubbing on us in our sleep.