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

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

... some condoms in there. “What’s this?” I asked, rolling my eyes at her. “Oh those are Kayla’s, put them back!” she said, then winked “Besides a girl can never be too careful.” I put them back and took another hit off the pipe for courage and we left the dorm. It was pretty chilly that night and the fishnet stockings did nothing to cut the cold. My legs had goosebumps and I was shivering by the time we got to the bar “This will be good for you” Mikki said, “Now you’ll understand what we go through for you guys.” What I understood was that my feet were killing me after the long two block walk to the bar and I couldn’t wait to get into the bar. Fortunately the bouncer barely glanced at Kayla’s license before waiving us in. The bar was very crowded and noisy with about ½ of the patrons dressed in costume. A lot of the girls there were dressed in similar fashion to me and Mikki, ala’ trashy Madonna style, although the phrase New Wave Hooker comes to mind also. It was definitely an eye-opening experience as we made our way through the crowded bar. I lost count of the number of times I was propositioned or groped by the time we got over to a booth that Mikki led us to, saying she knew someone at the table. There were a couple of girls from Michelle’s dorm sitting at the table and they invited us to join them. “Where’s your little boyfriend Mikki?” one asked. “Oh, he lost his Fake and I wasn’t about to miss out on Halloween at Dr Feelgoods. It’s the best party of the year! “ She ...

... exclaimed “This is Kayla’s cousin Bobbi. She’s in town visiting for the weekend checking out the campus to see if she wants to go to college here next year. “ The two girls introduced themselves, Cindy was a tallish blonde with big permed hair, Danni was a petite asian girl with a cute pixie cut. Both were dressed in classic eighties slutwear with heavy makeup “Where’s Kayla” asked Cindy “Oh, she had a sorority rush function she had to attend so she asked me to show Bobbi around, and keep her company tonight. “ “She trusted you with her cousin? That’s fresh!” They all laughed and I wondered what I had gotten myself into. One of the bartenders stopped by our table and said “Hi ladies, Mikki, good to see you again. Haven’t seen you in a couple weeks since we took your little boyfriends ID. I still cant see what you see in him. He’s just a pretty boy that cant even get into bar now.” I was glaring at him because he was the one who had taken it but he didn’t seem to notice ”Who’s the fresh meat?” he asked looking me over with apparent admiration. I blushed and was about to say something rude when Mikki put her arm protectively around me. “Don’t get any ideas Derek, she’s Kayla’s cousin and she’ll roast your balls over an open fire if you even try to hookup with her. And as for my boyfriend if you could eat pussy half as good as he can maybe I wouldn’t have dumped you.” The girls laughed while I turned a deep red, and Derek took our order and huffed off to the bar. I couldn’t believe ...