Nick - A Transgender Woman's First

His chest is smooth. We kiss some more, our tongues intertwining. I run my hand across his back, across his front. He smells clean, but with a distinctive musk.

I tug insistently on his belt and the hook of his pants, and his eyes widen as I caress his balls through his pants. I feel a shudder as I trace the outline of his hard cock on top of his briefs, but we quickly pull those off, too. He takes off his own socks.

His cock is at attention, and I lick my lips. "May I?" I ask. He nods, and I sit on the bed and lick a drop of pre-cum off of the tip of his cock. Salty and tangy, more like my own taste than I would have guessed. His penis smells intoxicating, with a hint of a tangy odor that sends me swooning. I mentally tick off a note about pheromones as I take him into my mouth.

I continue for a bit and then stand up. He fumbles at the zipper of my dress and I help him there. I shrug out of the dress, and he sees my bra and thong. "Am I as good in person as my pictures?" I ask. "Even better," he gasps.

He lowers his head to my breast, and gently suckles.

"You can do that harder," I say. I feel a slight tug. "No, really. You. Can. Do. That. Harder." He is more insistent, but it's not enough. "More," I command, and I feel a welcome pinch. As he sucks on my nipple I feel both of his hands on my ass, kneading my cheeks.

I sit down on the bed again and this time he kneels and tugs aside my thong. My own penis springs aside. He looks at me briefly, and then begins stroking my penis. He lowers his head and hesitatingly licks, and then takes me fully into his mouth. I arch my back and enjoy the sensation. He stops too soon.

I stand up and embrace him again, and even with my heels still on I have to reach up for my lips to touch his. My own penis, glistening slightly from the attention it's just received, brushes against Nick's still-hard, smooth cock. I arch an eyebrow and see even more desire in his eyes.

I tug my lover onto the bed. "You can ask for what you want, too, you know," I observe wryly.

"This is your fantasy, what are you thinking?"

"It's yours, too."

He lies on the bed, panting slightly, his cock still at attention. I inspect its sharp upwards curve. I push it down slightly and take him again into my mouth, beginning a blowjob in earnest. I pause and lick his balls, eliciting a groan.

"You like that, don't you?" I ask and he gasps out "Yes!"

The pre-cum oozing out of the tip of his cock is salty and I lap it up greedily. His cock smells clean and smooth, but as I had noticed before, his balls are musky with hints of something deeper and, until now, denied to me. I alternate licking his balls and deep-throating his cock until I realize the danger that he might very well not last much longer.

"Can you believe that's the first time I've done that?" I ask.

"I would never have guessed."

"I think I know what works."

I have no idea why I thought I needed to be coy by putting the condoms and lube in the hotel room's nightstand. I retrieve them and ask, "Are you ready for this?" He nods. I roll the condom down his cock and squeezed a dollop of lube onto it.

He spreads the lube around his cock as I straddle him, and I feel his lubed-up fingers enter me. I experience a pleasant fullness as one, then two fingers push in and began probing in-and-out. I stretch back and run my hands over his chest.

I don't need much more. I try settling back and feel his hardness near me, but can't connect. "Your aim needs help," I say, smiling. He takes his cock and repositions it, and I begin lowering myself onto him.

"Nice and slow, ok?" I whisper. I feel the tip of the head of his cock enter me, and ease onto it, bearing down. He was slightly smaller than the toy I was used to using, but he felt so much better. I slowly settle onto the length of his shaft and smile.

"This is probably a horrible tease for you, isn't it?"

"A little bit."

I grunt, and begin moving up and down on his cock, my own erect penis bobbing in front of us. I lose myself in the sensation for a bit, but am jolted as he pops out of my ass. We reposition. Fuck. Pop out.

"Here, do it this way," I say, as I climb off of him and get on my knees. Nick springs up, standing, and he quickly reenters me. We start a good rhythm, the sensation of fullness and motion sending jolts of pleasure throughout my body.

He thrusts into me; I push back, increasing our pace, imploring him for more. I bear down on his cock and feel a spasm. And then a pause.

My ass had apparently pulled the condom off of his cock. "The condom is still inside you," he explained apologetically as he gingerly extracts it from me. A dollop of cum drips onto the bedspread.

"That's why we have more than one," I shrugged. He goes to the bathroom to dispose of the used condom. He fumbles at the wrapper of the second one, his hands still slick with lube. I help open the wrapper, and he rolls the new condom over his cock.

But he was spent. He spends some time caressing me, brushing his fingers across my ass, gently touching my own balls. I run my hands through his hair, across his back. He has become sweaty, and the scent of sweat and sex was heavy in the room.

We spend a little more time cuddling before he finally stands up and goes to the bathroom to remove the condom and clean up. I stretch and retrieve a bottle of water and hand it to him. I reach into a dresser drawer and put on the satin robe I had stashed there earlier.

Nick began dressing. It was clear he wasn't planning on staying further; perhaps he was concerned about his performance.

"You like it...rough," he observed.

"I know what I like. That didn't seem too rough to me. I'm just enthusiastic."

He shook his head slightly, silently disagreeing as he buttons his shirt.

I stride towards him and hugged him, my head rubbing against his chest. I realize that I have a shit-eating grin on my face, and that it had been there for quite some time now.

"Thank you," I said. "I'm not sure what else to say, but...Thank you."

I breathe in the smell of his sweat mingled with my perfume and our sex, and realize that this moment would be unique for me. It was a first time, to be sure -- I had indeed just been deflowered. But I also realize that the two of us weren't likely to repeat this experience. I take in a breath, savoring the moment.

"You seemed to enjoy it," he says.

"I'm still grinning, aren't I?"

He gestures at me. "Are you staying here overnight?"

"I might as well." I shrug.

He leaves the room. I lie back down on the bed, still savoring the scent of his musk and our sex in the air.

A knock at the door. It's Nick, of course. "I can't find my car keys," he explains.

We rewind our memories trying to figure out when and where he shed his pants. We find his keys underneath the ottoman. We both smile and he leaves.

===

This story describes events that I lived. It is true. I started writing this story as a personal journal entry, but it took on a life of its own. I wrote about Nick and my 40th birthday so I would remember; perhaps I gave tangible form to my memories to shape them into the way I wanted to remember them.