Halloween Sex

Last Halloween, my roommate and I went to a costume party. I was dressed as Marilyn Monroe from that picture where her skirt blows up. I actually looked pretty passable and most people at the party didn't realize I was a guy. My friend and I got pretty drunk, took a cab home, and both helped each other back into our apartment. We kind of fell onto the couch together and he started to play with by fake breasts. One thing led to another and before long, I found myself giving him oral. When we were done, I got up and went straight to bed. The next day when I saw him, he asked if he could see Marilyn again. A few nights later, I dressed again and made him dinner. It was like a real date and afterwards, I changed into a naughty little nighty that I had bought for the occasion and we went to his room and had sex. I spent the night with him and woke him up the next morning with more fantastic oral sex. Since then, I have expanded my wardrobe and spend most of my time at home dressed as a woman. Fortunately, I pass as a very believable woman and we have even gone out of the house on dates. Before this, both of us had only dated women; but since that night, the sex has been so good neither of us has dated anyone else.

— Joel, 30

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