I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a policeman and dad played a nurse. It seemed they were role-playing, but mom was a man and dad was a woman?
After that night I took the courage to actually raid my mom’s closet. They were out and I wore her best dress, put on her best shoes and colored my lips. I looked lovely and I finally realized who I was at 22. A few days after that experience, I saw a club, a queer club. They had a crossdressing night party and that piqued my curiosity. I ran home to try the latest makeup trick I picked up at Sephora and attend this event.
My mom had this gorgeous red dress, made of silk and organza that I picked out. I had secretly bought a silver pair of heels and I wore those. With some eye makeup and a dash of lipstick, I was ready. I had put on a brunette wig completing my look. I called a taxi to take me to the club and entered a full house. There were many dressed as women and men. I knew I was attracted to males and one of my crossdressing fantasies was to have sex with a male. My eyes landed on the bartender; he was cute.
I make my way to the floor and meet so many like me, looking beautiful. I grab a drink and go back to the dancefloor. I have made a nice little group of friends. We chat and dance as the night moves on. I see the bartender making eye contact with me throughout and smiling. I return his smiles. I get to know so much about fashion and makeup as the night passed on. At closing time, I was met by the bartender saying, “You look cute.” “Thanks, you too,” I reply. We chat a bit and he asks if I wanted to go back to his place. I agree.
At his place, he offers me a cool drink and we talk some. I take the courage and kiss his lips. He returns the kiss and our tongues meet. I taste him and I want to keep on kissing. He holds my face, kissing me harder. He bites my lip and I feel horny and sexy. I feel powerful and attractive. His hands caress my buttock and I shiver in excitement. His hands move under my dress touching my thighs. Gradually he caresses my cock and it stands in attention. I look at him and lick my lips in anticipation.
He kneels and completely lifts my dress pulling my boxers down. He takes my cock in his hands and presses it. I am aroused completely and clutch the couch to not jump. This first sexual touch by a man is satisfying. He rubs my cock with one hand as he touches himself with the other. I can’t see his cock, but I know what he is doing. His head dips and he sucks the cockhead, pulling back the foreskin. “Ahh!” I exclaim at the sensitive touch. I really didn’t expect I would get so much pleasure enjoying my crossdressing fantasies. He presses my cock and my head drops back. Then both his hands are on me.
With one hand he is rubbing and pressing my cock as he sucks the head. With the other hand, he is fondling my balls pushing me to pleasure. I want to taste his cock too and I tell him. He sits on the couch and exposes his cock. I suck the whole length of his cock, trying to deep throat. I gag but he holds my head and pushes in further. “Breathe, breathe,” he instructs and I do. I blow him like that, deep throating and hearing his moans.
He stands up and gets a bottle as he pushes me to kneel on the couch. He adds the cool liquid to my ass, fingering me. My cock is still aroused as he does this. Then he pushes in his cock into my ass. Of course, it wasn’t at one go. I had never had anal sex. He tried twice and fingered me many times before his cock could get in. But now it is inside me. He is long and thick and my ass feels full. I am breathing hard as he begins fucking my asshole.
He moves, slowly, pulling back and coming in. His rough hands slap my ass once, twice, thrice. I scream each time, in throes of pleasure. And then he squeezes my cock and I cum. He cums in my ass too a bit later as I feel liquid filling me. He is still rubbing my cock, milking it, drawing more. I relax once he pulls out. He is kind enough to wipe my asshole filled with his cum. I wear my boxers again and sit down.
It is late, but we watch a movie together and when it is daylight I head home. My first experience as a crossdresser was excellent and I enjoyed living my crossdressing fantasies. Now I just had to figure out how to get my mom’s dress back in her closet.