Crossdressers First time

A Fantasy

I had met Steve thru GMM, we exchanged messages over a few weeks and then finally agreed to meet. I was very nervous on the way over to Steve's for two reasons. One was it was going to be my first gay encounter. The Second reason, and one i had only agreed to after Steve's insistence, was that i was going completely crossdressed.
I'd gotten dressed at home as Steve wanted. Putting on a satin and lace garter belt which i attached to lace top suspender stockings, then a lace bra with a satin and lace bustier over, the suspender straps also clipped on to the stocking tops. A lace thong, 6 inch pump heels and a little black velvet dress finished the clothing. Make up, lipstick and a wig finished off the look. I then hopped in my car for the drive across town to his flat. I loved the feeling of driving cross-dressed. The trip took over an hour in the busy traffic until i turned into his street.
Parking in the street was quite limited, the only spot was quite a distance up the street on the opposite side of the road. For a minute i waited hoping for a closer car park but there was no other choice. i would have get out and walk. i exited my vehicle, crossed when there was a gap in the traffic, trying to walk as quickly as i could in the high heeled pumps. Suspender straps pulled beautifully against my thighs as i walked, before i had to ascend three flights of stairs up to his third story apartment. With each step up the stairs i had to try and stop the little black dress riding right up and over the stocking tops
The door opened to let me in shortly after i knocked, i stepped past Steve into his flat. He was quite good looking, very fit, and wearing only a satin bath robe, which showed he was also quite well endowed. We stepped towards each other and started with a quick kiss. I stepped back not knowing what to do next. Steve sensed this. Reaching out his hands, finding my waist, pulling me against him, we began to kiss deeply. While our tongues played with each other , his hands found the hem of my dress, lifting it up. Our kissing stopping briefly, while the dress came completely up and off, then cast to the floor, then resumed with passion as i pushed my lingerie clad body against his. i could feel his erect cock rubbing against mine, i couldn't help but grind against him when his found my butt, grabbing running his fingernails at the sensitive cheeks.
Steve pulled away a little slipping his satin robe off, i looked down to see his 8 inch cock standing up hard between us. "i think i need you down there" Steve said, placing a hand on my shoulder, pushing me down until i was on my knees with his cock in my face. With one hand i guided him into my mouth, moving my head back and forwards as i began to suck my first dick. I slid my hand up and down the shaft, wanking him as i sucked hard on the big helmet, stopping only to lick and kiss his big dick, before sliding it back into my mouth, resuming my best noisy slurping sissy cock sucking . Steve began to move his hips with the motion, pushing him further into my mouth with each thrust, then both his hands worked their way down and cupped either side of my head. Now with each move my head was getting pushed further onto his knob. it was all i could to hold hips thrusting hips and brace while his big cock slid in and out of my mouth. Steve slowed his thrusts then looked down as i looked up, my lips wrapped around the head of his cock. "Wow, what a natural little cocksucker are, you just loved having it in your mouth didn't you? Now let's see if your tarty little rear loves it also.
Getting up off my knees, Steve guided me onto a single seater couch and onto my back my high heeled feet in the air. Applying some lube to my ring and some to his hard dick he spread my legs and slid in between them. Lubed up, his cock pushed against my slippery ring, the big head pushing into me as i let out a gasp. He slid in about half way then almost pulled right out, before pushing slowly back in again. There i was on my back, high heeled legs in the air, a sexy guy holding them apart while he slowly fucked me. "Ohh, Ohhh, Ohhhhh Yeah" i moaned as he penetrated my tight ass. It felt so good i could feel myself start to get hard. We continued this way for what seemed like hours, until Steve started to change our position. Pushing me further up into the couch, and sliding right up between my legs. His cock pushed again into me, deeper until he was fully inside me. He held it there, his cock buried inside me as far as he could go. Sliding his hips back he slid out quite a way, then pushed back fully inside me again. Each thrust back in came with a little more push until he was pounding his cock deep inside my sissy ass with each thrust. Bam bam bam bam he fucked me, almost taking my breath away at times, at others i screamed and moaned aloud, "Oh God, Oh Fuck, Oh Oh Oh, you are so deep inside me, Fuck, Fuck Fuck. Steve fucked me relentlessly his hard cock pounding my sissy butt.
After grinding away deep inside me Steve pulled out, slipping off the protection he then moved up a little, pulling his hard cock until he moaned loudly, hot cum spurting up onto my chest and neck creating a pearl necklace of dripping jizz. My legs were left trembling after my first fuck, Steve reached down his fingers beginning to pull my dick, still hot from all the sex it wasn't long before i was spurting cum all over myself too.
As i walked back to my car, my legs still a little shaky , i was a sexually happy little crossdresser. Having Sucked, Fucked and Cum my way thru my first dressed up sex encounter.
5starstarstarstarstarstarstarstarstarstar(20)