A Night to Remember Ch. 02

"I want your cum, but you can fuck me, if you want to," she whispered, not taking her eyes off of my cock. "I'm tight, and I'm ready for it." I looked over and she held a bottle of lube in her hand. I desperately wanted to fuck her by this point, before I blew my load in her hand, but to my great surprise something else happened instead.

I don't know what convinced me to do it, nor does it matter anymore. I took the bottle and set it down next to the bench, and then I leaned down, lifted Sarah's skirt up and put my head underneath it. She was completely hairless beneath the skirt and her inner thighs were super smooth, just like the rest of her, but I found myself staring at her panties. They were white and lacy, and I could see the definite outline of a thick, hard cock in them. With a gentle hand I reached out and pulled the front of her panties down, releasing her cock and letting it spring out in front of me. It was a little bit smaller than mine, but absolutely rock hard, so I timidly and wrapped my fingers around it, my palm rubbing the underside. Sarah's cock was very warm to touch and I heard her breathe in sharply as I felt her up and down, running my fingers over her.

"Please do it," she begged above me. I knew what she wanted me to do, even without fully knowing what I was doing, or what had come over me. I gave her a few long, soft strokes, getting used to the idea of what I was about to do, then I leaned forward and very slowly took her into my mouth, my lips parting around the head of her cock.

"Ohhhh," she breathed, one hand gripping my shoulder as she leaned back slightly. I had no idea how to suck a cock, but I had dreamed about doing it to Frankie, and I knew what I liked myself, so I thought about Sarah, Amy, Frankie and how they did it to me, and tried to copy their work as best I could. I slid my lips up and down her length and stroked her shaft when my mouth pulled back, licking it and getting it nice and wet. I could feel her breathing above me, her belly rising and falling as she clearly enjoyed what I was doing to her. It was a powerful feeling. With deliberate slowness I tried to ease my lips all the way down her shaft, but struggled to get past half way and had to pull back.

I felt the warm evening breeze on my face as Sarah pulled the front of the skirt up to look down at me, the slender fingers of one hand stroking my hair gently. I tried to take her deep again and got a tiny bit further, and as I pulled back I felt her reach down and cup the back of my head near my neck, her fingers running through my hair as she held me.

Having a girl's hand on the back of my head as I sucked a cock felt strange, foreign, almost unbelievable, yet her touch was warm and caring, like she was making love to my mouth. I looked up at her and the look of intense pleasure on her face made my current situation seem all the more outrageous, and feel twice as kinky. I bobbed my head up and down on her and felt her hand pulling me down with each motion, gently forcing my mouth over her cock.

"Oh baby, this feels amazing," she moaned above me. "Keep doing that, I -- oh god, I can't hold it much longer." I felt her hips move beneath me slightly as she gently angled to thrust up towards me when I slid down her shaft, reaching the limit of my deepthroating abilities each time. Her hand held me a little bit tighter and I started to feel her thrusting up into my mouth much faster, then she stopped me from moving altogether, pulling my head down low and holding me there as she worked her cock in and out of my mouth.

I felt slightly out of control as Sarah lightly fucked my head, but it felt exciting, naughty, kinky...in some ways wrong, but not in a bad way, not by a long shot. I was giving her pleasure, and I wanted to please her badly. Her fingers dug into the back of my head as she gently thrust into me, her cock moving fluidly between my lips as she panted and groaned, making little "uh, uh, uh..." noises.

One of my hands gripped the bench as I felt her suddenly start going much faster, the other hand resting on her hip in case I needed to stop her, but at this point it very much felt like I wouldn't be able to. Sarah was thrusting her cock into my mouth hard now, and her eyes were closed as she leaned back on the bench, her chest rising and falling with the effort.

"Oh shit yeah...fuck I'm gonna cum, you want my cum baby? You want it?" she panted. I looked up at her and she opened her eyes and stared back, her emerald eyes widening as she took in the sight of me sucking her cock.

"Oh -- FUCK!" she cried, throwing her head back again. Before I had the chance to reply properly I felt her dig her nails in and a jet of warm, salty cum shot into my mouth. The suddenness of it caught me completely by surprise, so much so that my mouth was half full before I could react. It wasn't as bad as I feared, in fact knowing the pleasure I was giving her made it exciting, but being new to it all I half-choked and had to pull my mouth away to spit her cum out onto the grass next to the bench as her cock pumped one last spurt out over my hand.

I sat up looking at Sarah's trembling body, her breasts heaving as she gasped for air, her hands gripping the bench to hold herself up, her long smooth feminine legs and, underneath her short skirt, poking out from her lacy silk panties, her long, hard cock, a string of hot white cum leaking out of the tip. Sarah took it in her hand and gently worked it back and forth, letting one last drop of cum work its way out onto her fingers as she stroked herself off.

When she was finished Sarah sat upright and hung both legs straight over the bench to sit next to me, shoulder to shoulder, her hands gripping the edges of the seat as she leaned forward, panting slightly, a blush on her face. She looked over at me and with her cock now hidden beneath her skirt she looked like a normal girl again, a warm and very satisfied smile on her face.

"Thank you," she said happily. "That was great, I've never cum so fast before! Most guys..." She paused for a moment before reaching behind my head again, but this time pulling me forward for a long, hot kiss, her fingers running through my hair as she moaned into my mouth. It wasn't entirely charged with sexual desire, there was something...else there. After a minute she pulled away slightly, just enough for me to see a cheeky, sexy glint in her deep green eyes.

"I think I know what you want now." Without waiting for a reply she stood up and reached under her skirt, pulling her panties down to just above her knees and spreading her legs, keeping her panties from falling down and swaying her hips from side to side as she smiled at me.

"If you want me, you can have me," she purred. "After a first date act like that I can hardly wait." In an instant I was on my feet and kissing her hard, my hands running up her back and down over her ass. My tongue found hers lovingly and my hands grasped her bumcheeks as she reached down between us and rubbed the extremely hard bulge in my pants. She knew exactly what I wanted, gently grinding her groin against me.

With a strange, animalistic feeling I turned her around and she bent over, a quiet gasp of joy escaping her lips. I watched with hunger as she quickly pulled her panties all the way down her silky thighs and kicked them off her shoe as she got down on her hands and knees on the grass. Sarah flipped her skirt up to show herself off, arching her back down slightly to lift it her ass into the air before me. I had to admit she had a very round bubble butt, and as she spread her legs she looked over her shoulder at me and wiggled it around, smiling cheekily.

"Come fuck me big boy," she said giggling. I didn't need much more urging than that. I pulled my pants completely off and moved towards her, kneeling down between her feet and grabbing the bottle of lube again, opening it and rubbing some up and down my shaft. I shuffled closer and pressed my cock against her hole, moving it around and spreading the lube over her hole gently. Sarah leaned down with her chest on the grass, ready for me, and as her hands reached back to spread her cheeks wide I pushed the head of my cock into her.

She was tight, as in ridiculously tight. I heard her gasp and she clenched around me, so I stopped, but then she relaxed and I began easing into her again, a little slower. I could hear her breath shuddering in front of me and I knew she must be feeling stretched, but I kept going. Suddenly she gave a small cry and I stopped again, worried I'd hurt her this time, but instead of pulling me out, Sarah pushed back against me until the last inch of my cock disappeared up her hole, her bumcheeks nestled firmly in my lap.

"Woooow..." she breathed from in front of me. My hands slid down her spine and back to her ass, my fingers trailing gingerly over her smooth body. I couldn't believe how hot and tight she was, and I was so incredibly deep inside her too. A long unsatisfied urge took over. I pulled halfway out and plunged my cock back into her ass, making Sarah cry out with both pleasure and shock. It was music to my ears.

My fingers gripped Sarah's smooth hips above the waistline of her skirt and I started to fuck her, pumping my cock smoothly in and out of her ass. Her breath came in pants and moans as we rocked back and forth, the sound of my thighs hitting her cheeks filling the night. I couldn't get enough of her tight, hot ass and the feeling of ramming my cock into it over and over again.

After her amazing blowjob, and the thrill of fucking her up the ass, I knew I wasn't going to last, but I wanted to make this one count. I started moving faster, really pounding her asshole, the head of my cock pushing deep into her belly as I fucked her from behind. Sarah's moans paused slightly and she reached back with one slender hand, pressing against my thigh.

"Oh god...ahhh wait, baby, slow down a bit...not so hard," she panted. I eased up on slamming my cock into her as deep as I could, but I didn't slow down. I couldn't, not when I was so close to cumming inside her, coating her walls with my seed. I was desperate, and I held her close as I leaned forward, my hands sliding up the sides of her body and underneath her shirt. When I reached her bra I hiked her shirt up, exposing her belly and bra, then lifted the whole bra up higher on her chest and let her breasts hang, rubbing them between my fingers as I fucked her. Sarah bucked and writhed beneath me as I thrust into her, feeling my release coming fast as I held her tits in my hands.

"AHHH fuck me! Yes, cum deep in me baby!" she cried as I pushed my hips against her asscheeks, my cock driving deep into her again. Sarah pushed her bum back against me as I gave her one big thrust as hard and as deep as I could, feeling like I was about to shoot my load straight into her belly. She gave a long, desperate cry and that set me off; I came hard, filling her up as I pumped my load deep inside her, our bodies rocking together, joined in a sweaty, sexy mess. We groaned together and collapsed forward on the grass, Sarah lying flat on her belly with me on top of her as my cock pulsed in her tight, hot little asshole.

We lay like that for a minute or two until I finally felt like I had stopped, my hands caressing her beautiful little breasts as she leaned up on her elbows, her head hanging. Slowly but surely we knelt back up together and Sarah got onto her hands and knees as I leaned back, her hand taking mine and wrapping it around her cock, which was rock hard again. We stroked it together as I gently thrust back and forth inside her asshole, making her moan and hang her head forward.

"God I could go again after that," she panted. "But...I think I'd have trouble sitting if we did!" With a gentle move she released my hand and pulled her bottom forward, my cock easing backwards out of her boy pussy. I pulled out with a sudden slip and a line of cum spilled from her asshole, running down her leg as she shivered before falling flat on the grass again, lying on her cheek and looking over at me sleepily.

"Whew, really you filled me," she laughed. Sarah knelt again and stood up shakily, a little off-balance on her wobbly legs. She fumbled around on the grass and started slipping her undies on but then paused halfway, her face blushing dark red.

"Ummm...I can't hold that..." she said quietly, then took a few hurried steps away and knelt down, her breasts still out and her undies dangling around one ankle. With one hand she held her skirt up while the other pressed gently on her lower abdomen, and I turned away, blushing madly as well, as she took care of the problem. I heard her wander back over and she collapsed on the grass again, her arms shakily holding herself up.

"So, umm, have you done this a lot?" she asked me, kneeling up and pulling her skirt back into place. I felt ashamed of myself, and was torn between admitting that I had been with a girl before -- and also admitting that it had been completely different, much more gentle -- or telling her she was the first sex-specific meeting slash hook-up like this I had been part of, which would at least partly make the reason behind my amateurish behaviour clear to her.

"Not really..." I eventually replied. I felt humiliated as I looked over at her. Sarah's breasts hung beautifully from her bare chest as she worked her bra back down, fitting them back into the cups before pulling her top down over her breasts and belly. She was a very sexy girl -- and I could only think of her as a girl -- and I had just made a fool of myself while having sex with her. She saw me looking and smiled at me.

"Well, we should do it again sometime." I couldn't believe my ears.

"Really?"

"Yeah. I mean, it'd be different, you know, the second time around. Maybe you could come to my house. I've got a big bed...it sure would be more comfortable than out here." Sarah grinned sheepishly at me. "Plus I won't get grass stains on the front of my top...or my knees." I blushed and she giggled again.

"Yeah...sure, we can do that."

"Cool." She stood up and wiped some grass off her bottom, jiggling it and her breasts perkily. "Well, are you going to walk a girl back to her car?" she asked, giggling again. I fixed myself up and we stood for a moment, the slightly awkward feeling of two relative strangers who just had messy sex and weren't sure how to feel yet, but we walked together back to the carpark. Along the way I kept stealing side glances at her, blushing whenever she caught me staring and gave me a dazzling smile. Sarah's long light brown hair draped over one shoulder, exposing her slender neck and her bare chest above the cut of her top. It really did hug her form quite well, and the rest of her look told me the kind of casual girl she usually was. I found myself actually liking it, if I could only come to terms with my inner turmoil about this whole scenario, and what I'd done tonight.

I led her over to her small car and she unlocked the door, dropping her backpack inside and turning towards me.

"Well," she said quietly. "It was...fun, a lot of fun," she said with a nod and a smile. "I hope we can meet up again soon." She paused for a second, then stepped forward and gave me a hug, her breasts pressing against my chest. I hugged her back and when we pulled apart I felt even more awkward. She looked just as awkward, but suddenly stepped forward again and kissed my lips lightly, playfully, and I enjoyed it.

"I look forward to it," I said to her. Sarah gave me a very happy glowing smile and turned back towards her car, then stopped and turned back quickly.

Just so you know I'm not free this weekend. There's a sex expo on that I want to go to. Have you heard of it?" I shook my head and her eyes lit up as she leaned forward on her car door.

"Oh it's this big event, you can usually meet a lot of other LGBT people there, and..." she paused, and this time it was her turn to blush. "Well, there's a lot of porn stars there too." Suddenly I was very interested.

"Oh, really. Shemale ones as well, then?"

"Yeah, loads of them. Why, do you think you might go?"

I did, very much so, which is how I ended up here.

---

So, as we leave our hero for now we find him reminiscing about how he ended up at a sex expo with transsexual porn stars. But the question is...which ones?

After talking with a few different people and getting some advice, I have compiled a small list of a few shemale pornstars. They aren't the top ten or the world's hottest or most active, just a couple who grabbed people's attention enough for them to pass their names on to me, and one or two who are less known but who I have seen myself, but they more or less fit the bill for Alex's tastes. Now I need your help: to choose who Alex will go after at Sexpo!

Transsexuals and Crossdresser fans, do your research, pick a favourite two or three, and either leave your vote in the comments below or, if you prefer, send me a private message with your choice or choices. And of course, you can always suggest your own favourite for me to consider! The ones I currently looking at are:

Bailey Jay (naturally)

Mandy Mitchell

Sadie Hawkins (also known as Riley Kilo)

Hazel Tucker (either pre or post-boob job, up to you as well!)

Bianca Freire (same as above)

Holly Parker

Sienna Grace

Sarina Valentina

Brielle Bop (also known as Chloe Callahan)

Kimber James

Vanity

Chloe Remy

These are just some of the many girls out there to choose from, the list is endless! But let me know what you think and once I have a few suggestions I'll consider each option, and one of them will feature in part 3! Thanks for reading!