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This page is for our crossdressers to send in their stories and share their experiences of all things feminine and girly. I’m a proud cross dressing gay male who enjoys all sexual pleasure I get.Crossdressing Stories – Kinky Crossdressers Well, no surprises there, guess who’s not the only one cross-dresser in the school now. Not just that he has even progressed from boring greys to colourful fun attires. We are often inspired by porn, but our attempts end up in giggles. We constantly keep experimenting with each other in the bedroom. He pulled out and wiped it with an easily available piece of clothing, my peacock jacket. He was gentle in the beginning, but my moans encouraged him to make it faster, till he filled me up. One thrust is all it took for me to lose it. He started by rimming me followed by a quick thrust. I knew the drill, so I got on my fours, protruding my butt, inviting him. I am still closeted, but I get to fulfill my fantasy every once in a while. He rose and whispered in my ears, “Let’s try some cross-dresser anal sex, shall we?” I nodded in approval. That night, by that muscular, big dicked black man, I was introduced into the world of crossdressing and I became a 'b s' crossdresser. It went on for a bit till I was about to come, but he stopped at the right moment. He looked me in the eye and smiled followed by another suck. He opened his mouth wide to give me a suck. His kisses were gentle, even on my hard cock. He kept kissing me down my throat, torso and now between my legs. He started kissing me while removing my clothes.
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We both giggled as we stood there alone in the dark library with just the moon light on our faces from the Gregorian styled windows. Then, Jared held my hand again and escorted me to the locked library through a secret door. We spiked our coke in the washroom and danced till wee hours to some legendary yet cliché rock songs like ‘It’s my life’. He looked me deep in to my eyes and said, “You know what’s going to happen tonight Ronald, I am going to make love to a cross-dresser”, as insulting as it sounded, I was turned on. I was confident that I looked dazzling than even most of the girls in that room. I even wore the matching eye shadow and long feathered earrings. I wore my mama’s favourite peacock designed jacket with shimmering white shirt and denims. I entered the room with glittering lights and bubbling crowd to the song of ‘Summer of 69’ playing on the loudspeaker. It was prom night and I walked in alone, in the name of making a statement.
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At times, I would even doubt if he really was gay. I would tease him every day, wearing makeup and popping my butt out at every occasion to make him notice my curves. So, I never asked anyone for prom but secretly waited for Jared to collect some balls and ask me out. I was worried that I will be made fun of at school, but my mama encouraged me to be who I really am and wait for that right person to come appreciate it, the way I like it. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male. I would walk around the store, making my mother laugh out loud. When I was 12, I went to shop for shoes with my mother.