Beginnings: My First time as a crossdresser (PT 1) - Sex Stories

Beginnings: My First time as a crossdresser (PT 1)

( Hi I am repostng because I want to string everything together for continuity ) Everything is connected so you should start at the beginning.) (This is a true story, the conversations in it are only as accurate as my memory can supply, as this happened Thirty years ago) When I was 17 I was dating a girl from the local college. I lived in a medium sized college town in a western state and it was 1983. It was Halloween weekend and we were both drinking some wine coolers she’d bought, the drinking age was eighteen at the time and she was nineteen, and smoking some pot I had brought over. We had planned on going to a party at a local frat house but it had gotten cancelled because the police had raided it the night before and busted them for u******e drinking at the frat.. So we had no specific plans and were bored, figuring out what to do with our Saturday night. Like I mentioned earlier it was Halloween so we absolutely had to go somewhere and party. She brought up Doctor Feelgoods which was a bar near campus, favored by college students and locals alike. I reminded her that my fake ID had been confis**ted a couple weeks earlier. “That’s okay. My roommate left her purse here and her ID is in it” Michelle said with a wicked glint in her eyes. I was confused, not seeing how it was relevant. “I’m sure if we dressed you up right you could pass for her. You’re both about the same height and have brown hair with green eyes. With your skinny frame all we’d have to do is put some of ...

... her clothes on you, style your hair right, and put some makeup on you and you would look like her. You two look practically like b*****r and s****r anyways.” I realized that she was right, I was fairly slender. I was a competitive bicycle racer and swimmer which kept me very lean, and I kept my body hairless like the other swimmers on my team (although it was as much a hairless fetish as anything else, I couldn’t stand body hair on me). I was 5’7” and 135#, smooth and hairless from the eyebrows down and my features weren’t particularly masculine, girls always thought of me as “cute” which was fine by me as long as it got me dates. My long brown hair (it was the eighties after all) was about the same length as Kayla’s. Other people had remarked upon the supposed f****y resemblance before so maybe we could pull it off. I had dabbled in crossdressing a few years before, sometimes stealing my mother’s panty hose and bras, putting them on and jerking off, while I pretended I was a hot teenage girl. Once I even dressed in her bra and panties while I sucked off my best friend and neighbor, who I experimented with a few times when we were younger. So the idea wasn’t completely out of the question. But by this time I was no longer a virgin with girls and I was quite sure I was straight, so the prospect of dressing up as a girl and going out in public did make me a bit nervous. But I was a bit buzzed and stoned so it didn’t take long for Michelle to convince me, especially when she ...