When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. 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.
It was my first prom and I was nervous. 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. So, I never asked anyone for prom but secretly waited for Jared to collect some balls and ask me out. I would tease him every day, wearing makeup and popping my butt out at every occasion to make him notice my curves. He would simply ignore and walk away. At times, I would even doubt if he really was gay.
It was prom night and I walked in alone, in the name of making a statement. I entered the room with glittering lights and bubbling crowd to the song of ‘Summer of 69’ playing on the loudspeaker. I wore my mama’s favourite peacock designed jacket with shimmering white shirt and denims. I even wore the matching eye shadow and long feathered earrings. I was confident that I looked dazzling than even most of the girls in that room. Suddenly, a hand grabbed my hand. I turned around to see, it was Jared. 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.
We spiked our coke in the washroom and danced till wee hours to some legendary yet cliché rock songs like ‘It’s my life’. Then, Jared held my hand again and escorted me to the locked library through a secret door. 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. He started kissing me while removing my clothes. He was hasty and I was breathless. He kept kissing me down my throat, torso and now between my legs. His kisses were gentle, even on my hard cock. He opened his mouth wide to give me a suck. I shivered. He looked me in the eye and smiled followed by another suck. It went on for a bit till I was about to come, but he stopped at the right moment. He rose and whispered in my ears, “Let’s try some cross-dresser anal sex, shall we?” I nodded in approval. I knew the drill, so I got on my fours, protruding my butt, inviting him. He started by rimming me followed by a quick thrust. One thrust is all it took for me to lose it. He was gentle in the beginning, but my moans encouraged him to make it faster, till he filled me up. He pulled out and wiped it with an easily available piece of clothing, my peacock jacket.
Me and Jared are a thing now. We constantly keep experimenting with each other in the bedroom. We are often inspired by porn, but our attempts end up in giggles. Not just that he has even progressed from boring greys to colourful fun attires. Well, no surprises there, guess who’s not the only one cross-dresser in the school now. I’m a proud cross dressing gay male who enjoys all sexual pleasure I get.