Losing a Bet on Purpose

On Halloween last year, I let my girlfriend talk me into dressing as a girl. What she didn't know was that I have been dressing as a girl my whole life and that I would do anything to become a girl for the rest of my life. When my girlfriend came by my apartment to pick me up for the party, she was blown away by how convincing I looked as a woman. I went all out; I went to a salon and had my shoulder length brown hair frosted and styled into a feminine look, I had acrylic nails put on (the girl said they would last a month and a half), and I had my eyebrows waxed into a thin, highly arched line. I also went to the mall and bought a new outfit including new heels and I stopped at the piercing place and had my ears pierced. I answered the door wearing a red, long sleeve, button up the back, silk blouse, a grey with black buttons and wide black belt mini skirt, suntan support pantyhose, red panties and matching bra, grey, open toed, four inch heels, a silver ankle bracelet, six silver bangle bracelets, a silver ladies watch and large, four inch silver hoop earrings. I was also carrying a grey purse with my makeup, perfume, id, and cash in it. When I got into her car, she couldn't stop asking me questions about how I was dressed. I told her that she was just jealous because I looked better as a girl than she did; this did not sit well with her and she said that she could at least pick up a guy before I could. I told her I doubt it, then asked her if this was a bet. She thought about it for a few minutes then said, "Yes, it is a bet." She went on to say if I lost, I had to have sex with a man that she picks and that she would film the whole thing and that I had to stay dressed as a woman for a whole week and go out with her anywhere she chose. If I win the bet, she would have to have sex with me any way I wanted and any place I chose, any time I say. The first one of us to French kiss a guy would be the winner and the bet starts as soon as we arrive at the bar where the party was being held. We both agreed and I said, "Let the best woman win." I couldn't believe how many guys were hitting on me, I felt like the woman I so longed to be; it all felt so normal to me. After about my third or fourth drink, I had to use the rest room. I decided I should use the men's room; I walked in and went to a stall where I sat down and urinated. All of a sudden, the stall door opened and a man entered my stall, closing the door behind him. He was standing right in front of me and without a word being spoken, he pulled out his package. I complied with what he wanted. I looked up at him when we were done and he smiled at me, and then left the stall. I pulled up my panties and hose, straightened out my skirt, and then went back into the bar. As I walked towards our table, I saw my girlfriend sitting in the booth with a man next to her. I walked over to the booth and slid in across from my girlfriend and her new friend. She introduced me as Cassandra and him as Mitch. Making sure I was looking directly at her, she grabbed Mitch by his face and leaned over and kissed him full on the lips, a few seconds later I see them French kissing. When they were done, Mitch excused himself to use the restroom. My girlfriend couldn't wait to gloat, plus the fact that she was pretty drunk. She said, "I win!" I said, "Yeah, I lost so you pick out a guy." She said, "You don't seem too upset about it; are you gay?" I stopped her and told her, "I lost the bet, I agreed to the bet and I will pay my bet." "Well," she said, "I am not waiting. I want you to do Mitch, I just need to get my camera out of the glove box because I am filming every minute of this. If it's not too much trouble, could you look up at the camera while you're doing it?" I just ignored her and told her I will be waiting out by the car. They came out ten minutes later. My girlfriend was true to her word, she was nonstop filming. When we were finished, he gave me a kiss then got out of the car and went back to the bar. My girlfriend got in the car and asked me if I liked it. I told her it was not that bad and I would do it again if I had to. Of course this just got her started. She said, "When I saw how far you went dressing as a woman, I thought you were gay. There is no man out there that could look as good as you do for only dressing up one time. Now you say you would pleasure a guy again. You've done this before, haven't you?" "Look," I said, "I paid some of my debt off tonight, now all I have to do is spend a week as Cassandra and go with you wherever you decide to take me." "That's right," she said, "and tomorrow I am taking you to all my girlfriend's houses to let them see the sissy I am dating and show them the video I just took. Then, I am thinking of taking you over to my mother's house, then to your mother's house to let them see what a sissy you are, but as for now, I want to take you to the store so we can get you a night gown to sleep in and I need a can of hair spray." I started the car and headed to the store to get my night gown and hair spray.

— Adam, 28

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