I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each other's fantasies and fetishes and did our best to fulfill them. It started with her admitting to her desire to give head while driving around in the city. I mentioned my longing to be tied up and teased and after a drive to her place I found myself tied to her bed for two and a half hours of torturous fun.
It was soon after that night that I told her about my biggest fantasy, to be dressed in drag and play the female for an evening. I saw the spark in her eye as the possibilities ran through her head. She asked if I had ever been in drag before (which I had once), and if I owned and female garments (I didn't at the time), but to my disappointment after that night nothing else about it was mentioned.
For weeks after that she subtly pried for more info about my past history and what I was open to, finding out if I had an exhibitionist streak, what lingerie and perfumes I liked and didn't like, even drug out the details of an encounter I had with a friend that ended with me giving him head. I even admitted to her I would be open to it again provided it was the right situation and person, but I had no desire for male contact beyond that.
As time passed we both got busy and finding time to see each other was difficult. After about seven weeks of not even talking to Lisa I left a message inviting her to a party my roommate was throwing to celebrate quitting his job. I didn't receive a reply but was happy to see her when she showed up with a few of her friends thinking I would get a little action that night. Unfortunately she had to leave kind of early but on the way out the door she told me she had been thinking about my unfulfilled fantasy a lot lately.
I wasn't surprised when she phoned the following Thursday and asked if I was available for the next weekend. She had just finished her last exams and was looking to blow off a little steam, thinking a weekend of sex would be just what the doctor ordered. I of course agreed. She was thrilled and told me to pack for everything from going to the beach to going to a club. "See you Friday before dinner!" is how she ended the conversation before hanging up.
Friday came and a knocked on Lisa's door just before five o'clock, she answered wearing a pair of shorts and a hoodie, not what I was expecting but looking cute nonetheless.
"Are you still interested in living out you crossdressing fantasy?" she asked bluntly.
"Sure" I said excitedly.
"O.K., this is what I have planned." She started. " I have been trying to plan your ultimate fantasy weekend for a while. I was thinking that instead of just one night you could spend the whole weekend as a girl. What do you think?"
"Wow" I was stunned and I'm sure it showed. "I hadn't thought that big but it sounds like fun."
"Great!" she shouted. "Here's the deal, I think I know you pretty well so I want you to let me take control, you can trust me to not push you past your limits. If I do push you too far just say "I love Margaret Thatcher" and we'll stop. Do you trust me?"
I did trust her, plus I was so turned on at the prospect my fantasy coming true I probably would have agreed to anything.
"I want you to hit the shower and give yourself a nice close shave.... Everywhere. Got it, bald from the neck down." she said with a wicked grin. "Oh, and no rubbing out a quick one either."
In the bathroom I found a women's razor and a fresh can of shaving cream. After the soaping part of the shower I lathered up my right leg and thought to myself that this was the point of no return. Fifteen minutes later even my arms were hairless and I was more aroused than I could have ever imagined. I got out of the shower and toweled off on my way into the bedroom where Lisa was waiting with her wicked grin.
"While you were in the shower I took your clothes and bag back to your place for you so you have no choice but to wear what I have for you. I have also noticed that after you cum your desire for keeping with fantasies drops off so I want you to put this on." she said handing me some sort of plastic device. "It's called The Curve and it's a lockable chastity device. But first we have to get rid of your hard on to put it on." Handing me a bag of ice to cool of my privates she took the device apart. A few minutes later I was staring at my penis encased in plastic with a brass padlock at the top, trying in vein to get hard again. "The beauty of this is that you can't even get hard let alone cum without the key which I put in my safe, so it will be a very frustrating weekend for you. Now let's get you dressed up."
She pulled out all the stops for me and I was soon dressed in matching bra, thong, garters and fishnet stockings with a short black skirt and a sleeveless top that showed of my mid section. She even found a fake navel ring to finish the look. After the fake breasts stuffed in my bra (C-cupish), a dark brown wig, and some make up (including bright red lipstick) I looked pretty convincing. Lisa was thrilled with her work and I was impressed.
Living in a big city has it's advantages like being able to go out but not see anyone you know if you hit the other side of the city. "I thought we should go out for dinner to celebrate the new you!" Lisa announced. I hadn't really thought about going out in public dressed in drag but it seemed Lisa had in fact planned on it. She could see the hesitation in my face and tried to comfort me "We'll go to the other side of town, no one knows us. Plus you look fantastic." Who was I to argue, I did trust her decisions.
We had a rather uneventful dinner (other than the inquisitive looks from our waitress) at a dark little Italian place where Lisa announced we were going dancing at a club next. I just about shit a brick. Dinner in a small restaurant was one thing but dancing at a club was a different story all together, I would have no choice but to interact closely with a ton of people. Lisa told me not too worry it would be dark, loud and we could pretend to be lesbians. With a smile she then reminded me how convincing I looked and that with the chastity device I wouldn't have to worry about putting a telltale tent my skirt. The combination of wine and her confidence soon had me convinced and we were on our way. The club turned out to be quite crowded and loud so my fears were mostly just in my head, I was even the victim of a few ass grabs. The only close call was when I almost went into the guy's bathroom out of habit but the bouncer caught me and directed me the ladies room.
