You don't meet a celebrity every day. And I didn't realize it until I tried my luck, seeing a lonely woman sitting at the bar in the hotel where I was staying. I had noticed her glass was empty, so I asked the bartender first to give her a refill, and one for me as well, before I asked if the seat next to her was free.



Smooth, she said, and waved her hand over the stool, indicating for me to sit down. Only then I realized she looked very much like Kim, a woman I secretly admired. Kim? I asked, it was out of my mouth before I could stop myself.



She smiled. I go by Cara here. Trying to stay away from publicity, so please keep it down. I'm sorry Cara, I said, your secret is safe with me. I didn't mean to recognize you. Only when she laughed, did I realize what a stupid comment that was. But I laughed sheepishly with her.



When our drinks arrived she said, I don't take drinks from strangers, so what's your name? I could feel my face turn a shade, where were my manners? Sorry, I said, my name is Paul. Well Paul, she said as she held up the glass for a toast, hope you like pink drinks.



I'm typically fairly smooth, but in the presence of this beauty my brain moved like it was stuck in mud. All I could say as I tipped my glass against hers was, I like pink.



If nothing else, she accepted my company, as we both took a sip. It was a girly drink for sure, but it tasted okay, a bit sweet maybe, but quite a dose of vodka. So I took another sip, a good size, a slight shiver going through me when it burned my throat. She laughed again, saying, you know Paul, I think we could be friends.



So we chatted like friends as she ordered another set of pink drinks. She wanted to know where I was from, why I was there, and if I was involved with anybody.



I was there for a conference that took place in another hotel, but they had run out of rooms. And no, I wasn't involved with anyone. She suggested that perhaps I secretly hoped that I would end up naked in bed with a celebrity. At which I replied, I rather see you in one of your leather dresses.



It must have been the alcohol that made me speak my fantasy, rather than the confirmation she expected, when inviting someone to her bed. But instead of being mad, her interest was peaked. You like me in leather? And I nodded, my face clearly coloring again.



Luckily for me, there is one thing leather lovers have in common, and she clearly is one. We like talking about leather, the feel, the smell, the color, the softness. And two more drinks later she knew exactly what my ever favorite dress on her was. And because it was one of her favorites as well, did she carry it with her when she traveled.



She wanted to know what I'd do, if she dressed up. I was honest, I simply wanted to take her picture, a few closeups and maybe a video. To sell to the tabloids? she wanted to know. At which I shook my head, only for my own pleasure. But she was still not satisfied. What pleasure is that, she demanded. You're just looking? Or you're fantasizing?



It was a fair question. I've never really watched her reality shows, and not everyone likes her, but no one would ever deny she is a stunningly beautiful woman. And I have spent many times rubbing one out, with her picture in my other hand. So I tried to be honest, but also diplomatic.



You're a beautiful woman, I said, I don't think any man could deny that. And yes, you're my fantasy as well, my perfect woman. And now that I have seen you up close, I realize you're even more breathtaking than I thought. And I want to remember that. For the rest of my life.



It was pretty smooth and I saw a flash of pleasure for a second on her face. Because it was the truth. Just not all of it. And somehow she knew. So, she started, you just look at my picture? Nothing else? That's a bit disappointing. Since you're rock-hard right now, and haven't even seen me in my leather yet. And she grabbed me softly in my crotch, just enough to feel the hardness in my pants. I want the full truth! Or the deal is off.



My shoulders slumped, I knew I had to tell her, or I would lose her. Okay, I said, the truth. The truth is, you do turn me on. I often wank off, with your picture on my phone. Once I have your closeup, in my favorite dress, I doubt I will wank off on anything else ever again.



She said nothing as she probably considered I was a pervert. Then, to my relief, she nodded. Okay, you're probably not alone in that. So here is my proposal. And in the minutes following she explained how this would be a two way deal. I would have to agree to wear one of her dresses as well, of her choice. And she would make pictures and close-ups of me. If I ever published any of mine, she would use hers also.



And it wasn't just dressing in her dress. I would allow her to make me look like a woman, with a wig and makeup and some other changes to my body to adjust my posture. I was to agree to all, or no deal. As she said, she wanted to be able to masturbate as well, on me, whatever she'd make me look like.



Now I had a few questions. Like what dress she had in mind, and it happened to be one of my favorites as well, and it would hide most of my body. But most importantly, I did not want to look like a guy in drag, to which she fully agreed. She also promised it would be fun, and it could be more than just a one night thing. I need a friend who is as kinky as me, she confessed.



As we left the bar, I paid for all our drinks. The barkeeper winked at me, having his own opinion of what was going to happen between us. In the elevator I had the first example of what it means to be around a woman like Kim. She had the penthouse and she had a special key to make the elevator go there.



Her suite had multiple rooms, one being used as her closet, containing dozens of dresses, tops, skirts, pants, leggings, shoes and numerous pieces of lingerie. She showed me the snakeskin leather dress that has ruled my fantasies about her. And made me touch the leather, which sent a shiver through my system, as the material felt like I had never touched before. I was wondering if I were allowed to touch it still, once the dress was on her.



Kim suggested we would both dress at the same time, rather than she go first, and then I bailing out after I had made my pictures. Of course I protested I would never do that, but when she let me touch "my" dress, I was speechless. The pure black leather was much thicker yet it was buttersoft. I simply wanted to know what it would feel like on my own skin. I actually suggested I'd go first, and although that got a smile from her, she decreed we'd go together.



It wasn't that easy though. As she explained, the clothing, gloves and boots would all be so tight, with my body hair it would be very uncomfortable, if not painful. So, she had me undress completely, nothing she hadn't seen before, she joked. Then she squirted lotion from what she said was a 500 dollar bottle, and she rubbed it all over my skin.



To tell you the truth, I wasn't the gentleman that I tried to be, but in my defense, if a beautiful woman, whom I had a crush on, rubs you all over, including my crotch, it's impossible not to get a hard-on. In her defense, again it was nothing she hadn't seen before, and she promised me we'd take care of that problem after my shower. She had me use her shampoo and soap, and as I cleaned myself every hair on my body came off, including my face, except my eyebrows and on top of my head.



She used a different lotion on me afterwards, saying that would keep my skin soft and smooth for at least a week. By then, she had started her first piece of lingerie, which was needed under her dress. It was a practically nude corset, that narrowed her waist and made her breasts much more pronounced. I couldn't help it but my hard-on came back, just by looking at her.



She was non-plussed about it, saying first my own corset. It was an elaborate contraption, made from the same soft leather, just thinner than the dress. It was designed to give her more curves under the dress, otherwise she'd look too flat under the thick leather. These would be my curves now.



Before she tightened the corset on me, she filled the cups with a set of falsies, although the weight was immediately noticeable. Then, with the corset tighter and tighter, they stood out farther, and it would have hurt my posture and probably my back, if it weren't for the very same corset. My breathing became more and more shallow, but Kim knew how tight my waist needed to be, in order to fit the dress.



Part of the corset was designed to pad my hips and buttocks, and even my thighs, as she pushed flaps of "skin" onto my own skin.

In a cruel twist of fate, when I saw myself in the mirror however, my own curvy body excited me, and my dick started growing again, an awkward sight on my now very female body.



Aha, Kim said, how about you take care of that? And in a very experienced move did she pull a condom over my dick. Would you mind if we add a bit of kink? And she showed me a pink egg, or at least that was the only thing that came to my mind, with a tail attached. I had no idea what it was, but it looked innocent, so I said, sure.



That's when she slowly started inserting the egg into her bare pussy, which was a very erotic show, resulting in my member growing rapidly. But nothing prepared me for the little remote she pushed in my hand, indicating to push the button. When I did so, everything about her changed.



I could actually see the skin of her pussy vibrate, as her legs gave in and she fell back on the bed. Quickly I pushed the button again and the vibration stopped. But she moaned, use the dial but don't stop. So I pushed the button again and turned the dial to the left, which clearly reduced the vibration and gave her a bit relief. Quickly it became a game, where I turned it up and saw her body arc, then down for some relief.



It was simple, her not knowing what to expect or when, was extremely erotic, for both of us. I had begun to stroke myself with my other hand, getting bigger and bigger, even though I couldn't see it at all with my breasts in the way. The power I had over her rushed to my brain through my dick. I could feel I was going to cum soon, and I timed my control over her so that she came at the same time.



Her scream topped it off, as I heard myself moan as well, shooting my load into the rubber protection. I knew it would have been a huge mess in her room, so I was grateful for her awareness of the situation.



When I turned around and looked in the mirror, I could see an enormous load hanging down. I started removing the rubber when Kim said, let me take care of that. I moved back towards the bed, where she was now sitting, her face still flushed with pleasure. I could feel her remove the protection, but I couldn't see what she was doing down there, other than that she had a wet towel in her hands.



Suddenly I heard a hiss, and my whole crotch area was freezing. I cried, but she said, no worries, I'm taking care of it. The next thing I hear was a tiny click. And then she moved a few flaps that were still hanging down between my legs, and it snapped all together somehow. Now take a look, she said.



I turned to look in the mirror and my dick was gone. It looked very much like I had a pussy now. And my curves were even more extreme. But female, no question about it. Ready for your part of the kink? she asked, as I thought things couldn't get weirder than this. She took my silence as a confirmation and showed me a pink egg with tail similar to the one still peeping out from her. Except this one was all glistening with moist. Was she going to use that in my new pussy?



But I had to put my hands on the bed, bending over and as I felt the weight of my chest hanging down, she moved behind me, and although it felt like she was inserting it into my ass, I couldn't feel a thing. And then suddenly I could.



Something was sliding up my ass smoothly and it went deeper and deeper without any resistance. The moist must have been some jelly. I tried squeezing a bit to stop the progress, but instead it sucked in deeper. Oops, Kim said, that wasn't supposed to happen. What? I cried, worried by now.



Normally we keep the tip visible, she explained, so it can be pulled out easily again. But this one just disappeared from sight. Don't worry though, it'll come out the first time you do a, you know, a number two.



But what about my dick, I begged, what happened to that? Oh right, she replied, simple really. I cooled it down to shrink it. Then I put a chastity cage around it to keep it that small. We don't want it to grow once you wear that dress, right? Not to worry, here is the key, you can keep it if you want.



She showed me what looked like a needle or a pin, with a diamond head. At closer look the metal had some groves, which had to make up the key part. It's the safest and most comfortable chastity money can buy, she said, it should not hurt if you get an erection again, it simply won't happen. There's only one key, that fits the smallest lock possible. Without the key it would require surgery to remove your testicles, in order to free you from the cage. The pin can be worn as a brooch by the key holder, or I can simply keep it in my safe.



She pointed at the safe that stood open, and which probably had contained the cage and egg toys. I gave the pin back to her and said, please keep it safe, I don't want to accidentally lose it. But tell me, why can't I see the cage, it looks like I have a pussy.



Yes, she answered, obviously the dress and corset were designed for me. I needed the extra padding to give me more curves. The padded pussy would allow access to my vagina, there is some lining to feed it into my real pussy, but obviously you have nothing behind it. I would also need a thin tube to extend my pee hole and something bigger to line up with my anal hole. The first tube is inserted into your penis and held there thanks to the cage. You can pee, as long as you sit down like a girl. And likewise, as I said, you can poo as well.



I was stunned. It sounded so logical and simple as she described it. And I had the key, so we could undo it all anytime I wanted. As a matter of fact, maybe it was caused by the tube, but I felt like I had to go. Kim showed me where the bathroom was and suggested she'd hang around, to explain how women clean up afterwards. I was grateful for that suggestion.



It was a truly weird experience. When I let go of my bladder, the pee came out somewhere behind where my scrotum used to be. But it sprayed nicely into the toilet, although Kim pointed out how a part of my "fake" skin there was also wet. And I used toilet paper to wipe it.



Anyway, relieved that everything still was according to plan, at least Kim's plan, I was ready for the dress. But she suggested I first try out the button on the remote control again. Man, she is kinky, I thought, as I pushed the button. She reacted instantly again, but now I could feel a tremendous buzz in my rear as well. It was pleasant for sure, as a moan escaped from my mouth, but in seconds it triggered what normally would give me an erection.



The erection did not happen and it turned into an uncomfortable dissatisfaction. All I could do was twist the knob to the left, giving both Kim and I some relief. The buzz was pleasant now but nothing more. Then I pushed the off button, as Kim looked at me with a smile. We're in the same boat now, she said, we're linked by our kink. By the way, that remote works from a mile away, so let's keep it between us, or someone can drive us crazy.



From that moment it was all simple fun. I got to wear my first thong, which was quite an experience with part of my buttocks being fake, so it cut in deep. Then I had to wear boots that came up almost to my crotch, so tight that I was indeed thankful I was hairless now. Obviously the four inch spiked heels were also a first. We practiced at least for half an hour, until she was convinced I wasn't going to trip while wearing the dress. Twice she surprised me with turning on the remote, but I did not topple over. What was interesting was that it got more and more pleasant as I accepted that the intruder in my rear was now a part of me.



Finally the dress. She went first, as I made pictures during the process. She posed sexily for me each time, and I felt myself falling for her in a way not experienced before. When the dress was on she let me feel her all over and it was better than just feeling the dress. When I fondled her breasts, she moaned and turned the remote on softly, and as I moaned with her she kissed me.



Now, this is a woman with tremendous experience, as seen on TV and in many magazines. Us fans can only imagine what it would feel like, and how much passion would be in it. Reality simply blew me away.



It was pure passion, impossible to fake. Her kiss was soft, while her tongue ravaged me. She pulled my face into her, so I couldn't pull back, and I tasted her lips, her tongue, the drink we had before and something that I could only call pure femininity. When I tried to answer her kiss, our tongues tangled in a flirty dance, until she allowed me in and I could skim her perfect teeth and now I tasted desire.



I simply forgot to breath and started getting lightheaded, but she sensed it and pulled back a bit so I could pull some air in. I was hanging on to her now, my arms wrapped around her, my hands on her leather butt, and I could only conclude I was in heaven. Yet when we finally pulled back, she exclaimed, wow, that was fantastic! I could only nod.