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Her choice for going out to celebrate was a drag night at a club. It wasn't so much fixed on drag as it was on gender parodies and cross-dressing for fun. I had been a closet cross-dresser for a long time, although I had told a couple of girls I knew. Everyone was going to cross-dress and have fun, but I was going to revel in it. I had never been with a boy before, not even kissed one, but every time I was in women's clothing I wanted cock. During the daytime, I hung out with Karly and my other girlfriends including Olivia and Sinead. I had always seemed to find it easier to get on with girls than guys. We chatted generally before they asked what I was planning on wearing. I laughed, slight uneasily saying I wasn't sure. They asked me how far I planned to take it and I said that I'd shaved my legs anyway because I didn't like body hair. "Well we could help you get ready, see what looks good on you," said Karly. We rummaged through Karly’s wardrobe, picking outfits for me to try on.. I knew she was having a small orgasm as I felt her pussy contracting on my finger. “Are you okay?”I asked her after she took a deep breath and exhaled “that felt different” she said relaxing her legs. I kept my fingers inside her as I moved up sucking on a nipple that had started to rise.She grabbed my head and moaned as a warm feeling of cum slipped out around my fingers. I moved up and kissed her as she pushed her hips up off of the bed sucking my tongue into her mouth. With each orgasm she became wetter but still not wet enough to where I would be able to slip my cock inside her. I finally was able to move away and stand up, with a smile I undid my pants and grabbed my hard cock.She had a look of fear on her face as I moved between her spread legs and kissed her. She took a deep breath when I rubbed the head of my cock along her slit and tapped her clit with it. I smiled “relax honey you're not ready for this yet”but continued to rub it up and down on her.I pushed on my cock.
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