Sexy Glamorous Drag Date - Bedroom Fantasies #51

My interest in drag began when I first saw RuPaul's film clip for the song Supermodel. It was that moment that I realised I was attracted to someone of the same gender but dressed as someone from the opposite gender.

Many years later and we now have RuPaul's Drag Race bringing drag to the mainstream and my enthusiasm for it has not left me. Though I'd dabbled in elements of crossdressing before, there were now countless tutorials online for how to get makeup just right and ways to best complete the look. As a pansexual man, the idea of dressing up as a high glam woman and then 'servicing' a masculine man is quite appealing so why not see where it can go?

After 'researching' many online clips and a lot of practice, I finally got my overall look down: high-gloss cherry red lipstick, smoky eyeshadow and a somewhat figure-hugging sparkly black dress, capped off with some shiny black five-inch high heels. In the right lighting, I looked pretty good, but the real test was to come.

I'd been chatting to a guy online for a few weeks and we both decided it was time to meet. I was all dolled up with somewhere to go. We met at a club but the attraction was so instant that we didn't stay long and he drove me to his apartment that had a fantastic view of the ocean. We only just got inside the door before he pressed me up against the wall and locked his lips to mine, his tongue tracing the outline of my mouth.

I slowly undid the buttons on his white shirt and exposed his muscular chest before leaning down to take his hardening nipple in my mouth and give it gentle licks with my tongue. That seemed to get him excited as he began to unzip his pants and I didn't need any more invitation than that. I traced my way down his torso with my tongue before finding his growing phallus right before my eyes. I'd only sucked one cock before and to be honest, it was a little small and didn't quite feel fulfilling. This one was just right though, about 6 inches with a generous thickness.

I danced my tongue across the tip of his penis before lowering my mouth over it and then letting it slide in and out. I felt as he grew harder and harder and before long, I could feel the pulsing that indicated he was about to cum. I let him know I wanted him to let me taste it by gripping his tight buttocks and pulling him in close to my face as he shot his warm salty load down my throat. I stood up and he kissed me, tasting himself on my tongue.

But this was just the entrée. We moved over to his floor-to-ceiling windows and hugged on his couch until he was ready to go again. He began by removing my dress, then he pulled my lace panties down and he took my member in his mouth. He knew just what to do and had me hard and dripping in no time.

But he wanted more.

He stood me up and took both our cocks in his hand, one on top of the other and stroked them for a moment before motioning for me to take a position against the window. 

I placed my hands on the glass and felt as he gently spread my ass cheeks apart, then I felt his warm tongue flick across my anus and a jolt of pleasure shot through my body. He kept flicking his tongue over my asshole until it was all wet and relaxed, then he stood and slowly pressed against me with his bulging cock. It took some work to get in and there was a little discomfort...but once he was in, it felt divine. I finally had a real cock inside me, filling my ass and sliding back and forth in me. 

I turned my head around as far as I could and we kissed as the stars twinkled in the background.

He continued thrusting into me as he reached around and played with the head of my dick, which was dripping with precum. I felt as he gripped my hips and thrust harder and deeper and knew he must be getting close. As it turns out, so was I. I felt as my own cock pulsed with rush after rush of pleasure until finally I came. Moments later he too ejaculated, spilling his hot seed deep inside me.

We both lay back on the couch in each other's arms and fell asleep to the sounds of waves crashing.

Submitted by Chris from Ballarat, Victoria Australia

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