tagTranssexuals & CrossdressersYou're Gorgeous and I'm Curious

You're Gorgeous and I'm Curious


I love a lady in a short, short skirt, and this lady was wearing one of the shortest I'd ever seen: a bit of sky blue denim that barely reached her upper thighs and left her long, luscious legs mostly in view, covered as they were in just the tightest thigh-high white stockings.

She was perched on a barstool not six feet away, one thigh crossed over the other, her short skirt riding up her legs so high it was easy to see the white garter straps that crossed her lightly tanned flesh before vanishing under the skirt.

The rest of her was smoking hot too: nice breasts beneath a long-sleeve blue top, shoulder length bottle blonde hair, and a pretty if angular face. Maybe thirty, give or take a couple years. She was certainly better looking than the girl she was talking to. In fact she was the best looking thing I'd seen that night in the club, and that included the semi-drunk college girl my buddy was off dancing with. Like I said, I'm a sucker for a girl in short skirt.

I kept my eye on her as I nursed my vodka cranberry, imagining what it'd be like to run my hands over those sexy stockings, slowly rolling up that short skirt and diving my fingers along her panties. I was looking for a chance to go up and say hello, but this part of the club was a small bar jutting off the main dance floor, and it was loud and crowded. So I clung to my spot against the back wall, watching Miss Sexy Legs and nursing my drink and waiting for my opportunity.

Like I said, Sexy Legs was talking to a slender, brown-haired girl at the bar next to her. They had to press their heads together and shout to make themselves heard. I certainly couldn't hear them or anyone else around me, not that I cared. I had a nice buzz going and those legs were looking sweet, in fact they were getting me stiff.

She glanced over my way after a moment, no doubt she'd caught me checking her out, so I gave her a smile and an eyebrow. She turned her head back quick to her friend, embarrassed, but she smiled to herself and after a moment or two sent a few shy glances back in my direction. She had absolutely stunning red lips and her smile that really brought out the beauty in her face. Maybe she was a little flushed from the attention, as she slid one hand absently along her stocking, teasing the garter strap nervously while she nodded to some comment her friend was making.

Just then a third girl came up and put her hand around the brunette, and all three of them started waving their hands to get the bartender's attention. After a bit they got their drinks, so Sexy Legs gathered up some dollar bills from her friends for the tip jar. I guess she meant to give the bartender a bonus, but she ended up giving me a bonus too.

She stood up off her stool -- tall gal! -- and then leaned out across the bar, tucking the notes into a jar almost out of reach. That movement was heavenly, because it lifted the back of her skirt up another few inches and gave me a fleeting glimpse of tight white panties nestled between a couple of smooth, perfect ass cheeks, before she sat down again. That lovely sight nearly made me spit my drink and there was no 'nearly' about it now when it came to my pants: that was prime erection fuel, no lie.

I recovered a little bit, sipping my drink and moving my eyes up and down the line of people at the rest of the crowded bar. Didn't want to make it too obvious I was staring just at Sexy Legs, of course. There were a couple of other cuties around now, but it was so crowded and they were much further down the bar that I really didn't have a chance to make eye contact with any of them. And I certainly couldn't see them as well as I could Sexy Legs, perched as she was on her stool just opposite of me.

My eyes inevitably wandered back to her and her friends, just in time to catch the two other girls heading out onto the dance floor, whether as a couple or to look for someone to dance with, I wasn't sure. Legs turned in her chair to put her friends' drinks beside hers, then spun around on the stool, half facing the alcove again.

She had uncrossed her legs when sitting down again, and now I could just make out another glimpse of her tight white panties under the skirt, this time from the front. Oh yes, I thought. Move those legs a little wider, slip that skirt up a little higher, slide that ass further down the stool.

She was totally unconscious of this, now having turned her upper body back towards the bar and asking the bartender something. As she did though, what I had hoped for was exactly what happened. Absent-mindedly she shifted one leg almost at a ninety degree angle to the other, while inching down the seat a bit. This caused her skirt to rise up her hips, giving me the shock of the night.

Her panties were packing a huge bulge.

Seriously. That was a cock under that tight, white silk. I was sure of it. It was too prominent, shaped too exactly to be mistaken for a large labia or some bunched up pubic hair. Plus, now I could just make out a bit of the smooth, hairless flesh of her sac forming a crease between legs and panties.

I stared, couldn't help it. I definitely wasn't expecting that! This club was gay-friendly, sure, but it was not a gay club, and certainly not a transgender or cross-dresser hangout, not that I was aware of.

Like I said, I like girls, especially girls in short skirts. The whole guy thing just doesn't do it for me. But a chick with a dick, that was okay with me too, pretty exciting really. At least in theory. Truth was, while I'd seen a lot of shemale porn, that's all it was -- just a pornographic fantasy. I never thought I'd actually meet a girl like that, especially at a bar in my town. But there she was. My hard-on was raging by now.

It couldn't have lasted more than nine or ten seconds, when she abruptly looked over at me and saw me staring, then looked down and turned bright red and turned around really fast. She certainly hadn't meant to flash the bar like that. She turned around quickly and slipped off the stool, pulling her skirt down over the back of her ass and smoothing out the creases. I looked up and down the bar, particularly at the guys talking loudly next to me, but nobody else seemed to have noticed. I grinned and took another sip of my drink, checking out her ass under that short skirt again with renewed interest. Damn! It was about as round and tempting as any girl's ass I'd ever seen. Just knowing there was a plump, juicy surprise tucked under that skirt too was driving me even crazier. I finished my drink and made my way over to the bar, slipping into the space her friends had vacated.

She noticed me, so I turned towards her and smiled. She had big, pretty brown eyes and a nervous look on her face, stirring the straw of her drink in a slow, dainty circle. Her features were flushed, either from drinking or embarrassment, maybe both. "Hi!" I shouted over the driving beat. She smiled back softly and looked away, though she made a little half-turn towards me as I sat down on the bar stool next to her. I glanced down at her lap, but her legs were firmly crossed again.

I grinned and leaned in towards her. "You gave me a little surprise!" I said.


"I said, you gave me a little shock!" I said, yelling this time into her ear. The music was ridiculously loud, but her hair smelled nice. There was a gold piercing in her ear. She pulled her head back and nodded, then turned to lean in towards my ear:

"Sorry! It's this stupid skirt. It's too short."

I shook my head and grinned. My turn to lean in and shout in her ear: "No I like it. Very cute!"

She smiled at that, blushing again, but she turned more towards me on her stool so it was easier to lean in and talk. Her crossed legs bumped mine, the heel on her raised foot gently resting against my knee. Mercifully the music dropped in volume a bit, just as the bartender came and gave me a drink. We chatted.

Her name was Alicia, she was a teacher a private academy not far from here, out clubbing with her two friends. Me too, I told her, mentioning my buddy who was off dancing somewhere. As we chatted, I got a better look at her: sure, the makeup was a touch heavy, but I could the shape of her breasts, the skin and cleavage showing under the light blouse that she was certainly a transsexual, not a cross-dresser. Those breasts were delightfully feminine. Maybe it was the slight buzz, or the dark, moody lighting in the club, but she looked absolutely gorgeous, and I told her so.

"Thank you hon!" Alicia grinned, giving my bicep a squeeze. "You're not so bad yourself." She took a big swig from her drink, then with a playful sparkle in her big brown eyes, asked, "So much how did you see?"

I grinned, reaching out to touch her upper arm with my finger. "I was checking out those sexy legs from just over there for a bit. Then when you leaned over the bar to put money in the tip jar, I got a nice look up the back of your skirt!" She opened her eyes at that, then laughed again, obviously not realizing she had done that. "Then when you sat down with your legs apart, I saw your you-know-what," I finished.

"My what?"

I leaned in close to her ear, raising my voice against the music. "Your cock!"

We both laughed at that, and took another drink. She leaned in again. "You're OK with that?"

I shrugged, nodding. "Sure! New to me, but you're gorgeous and I'm curious."

She grinned, and we finished our drinks as the music kicked up again. "Curious? And a little excited too," she said. She teased her high heel across the front of my Jeans, where my rather prominent erection was tenting the fabric quite obviously. "Now you're getting me worked up too!" she said, leaning in closer.

She uncrossed her legs, then turned fully towards me, arms entwined with mine, and pulling me to a standing position between her knees. She remained seated on the bar stool, facing me. With how close we were now, I was the only one who could see between her legs, which had my rapt attention.

Her thighs slowly spread wider, lifting up her skirt and showing me her bulging panties, deliberately this time. There was no question about her transexuality now, the previous bulge had hardened into quite a stiff little erection, making a naughty little cylinder in the white silk panties, above the curvy base of her balls. As I stared, maybe drooling for all I know, she reached down and began to stroke her cock through her panties.

I couldn't believe it, it was the most hottest thing I had ever seen. I had never seen a t-girl before, not in person, and now I had met a pretty one, and she was ... showing me this. "Do you like that?" she smiled, leaning her face close to mine.

I nodded, lifting her chin with my finger until our lips locked. Kissing her deeply and pulling her close. "I love it. I want you babe," I muttered, all eloquence, I know. But when you're aroused, you're aroused.

"I want you too, babe," she whispered back, tongue tickling my ear. She pulled her head back, letting me see between her legs again. The tip of her cock was peeking out the top of her panties like a pink mushroom across a silk-covered column. Her hand took my wrist, and guided it against her sex.

I felt her cock through the silk panties. I felt all of it, the whole length and circumference. My fingertips strayed up to the tip, naked where it jutted over the band of her panties. "Oh so hard, yet so soft," I murmured. My hand roamed down the trapped cylinder to her base, to stroke her thick and playful balls through the thin fabric of the panties. She felt soft and smooth down there. "You are driving me crazy. Come home with me tonight!"

She smiled, and kissed my ear. "Can't do that. Got to take friends home -- but..."

"But what? Dance, maybe?" I was grasping for straws.

"No, not that. In this skirt, this hard?" She laughed, and kissed me again. "I have an idea though. Follow me." And just like that she slipped out of my arms and off the bar stool, straightening her skirt and leading the way.

She led me to a stairwell that went to the roof where the smokers went, but it was deserted right now. Two steps ahead of me, I had my eyes on that short skirt and tight ass as we went up the first flight of stairs, then the second. The stairwell was ours alone.

"Wait," she said, smiling over her shoulder. "Turn around. No peeking." I did, though I was reluctant to take my eyes off that tight ass. I heard her take a step or two, then the zip of her purse. "It's OK now, you can turn around," she smiled.

She was halfway up the next half stair, smiling down at me. She still had her short skirt on, but the panties were gone. Her cock was in her hand, long and slender as she stroked it, the pink tip almost seeming to wink at me.

I groaned, and charged up the stairs, but she kept a few steps ahead of me, turning around now so I could see her bare ass cheeks, quite naked under that tiny skirt. Two smooth, tanned globes, as lovely a roundness as I've ever seen. With another step, her thigh lifting boot to the carpeted tread and I could see her semi-erect cock dangling down between her thighs. I could've creamed right there, I could have died.

She teased me up the last of the stairs, then burst open the door into the smoking area. Chill night air blasted us both, and the soft buzz of a few smoker's voices. My alarm went off a little bit -- other people were around -- but she just smiled and took my hand, leading me around to a gate on the side of the stairwell building. "I know a place. I hope it's unlocked," she whispered and tried the gate, and it was.

We stepped into a little wooden gated area alongside the stair access where some bins and boxes were stored, and shut the gate behind us. We were in our own little world now. "Great spot!" I said.

She stepped right up to me and grabbed the front of my jeans again, stroking my erection with one hand as her other unclasped my belt and nearly tore the buttons off. I just moaned, letting my pants and boxers fall to my ankles. "It's perfect," she said.

Catching her eye, I pulled her in close for an open-mouthed, tongue-grappling kiss, which she stepped into, pressing her thighs on mine, lifting her cock up out of her skirt and rubbing it against my hardness in the cool night air. "Just perfect," she moaned, as her hand entwined both our cocks, rubbing them together with expert precision until I could feel the precum oiling from my tip.

It was seventh heaven, my first time with a girl like her and I couldn't believe how hot it was, despite the cold night air. Desire kept me warm: her body wrapped against mine, her bare breasts beneath the thin fabric of her blouse pressed against my chest, her lips and tongue wetly grapping; the feel of her long, stiff girlcock rubbing against mine, her hands expertly slapping the two pricks together as her free hand found my balls and began to pull and stroke.

"Babe, I'm going to explode," I moaned.

She slipped her blouse off and tossed it to the ground, then knelt on it. What happened next was the most fantastic blowjob I've ever had. She knew just where to lick, when to touch, what to kiss, how to suck. It wasn't but a moment or two before my cock twitched, hard, sending a wet sticky stream shooting down my jerking length. She pulled my tip out her mouth just as I came, working it between her fingers as my load coated her bare breasts. I opened my eyes and looked down, saw her beautiful breasts glistening with cum. She continued to jerk her own stiff prick while nuzzling my drooping member.

After a moment of licking and sucking me dry, she rose to her feet again and guided her erection against my sticky tip. We frotted again, while our mouths found each other for a long, lewd kiss. Her cock was erect as ever, teasing my excited prick back in its half-erect state. "Want to do me?" she asked, and I nodded. I was eager for this.

I dropped to my knees on her blouse, and looked down to see the most lovely femmecock I've ever seen -- and it was real. I dove hands-in, gripping that throbbing length and stroking it up and down with one hand, fondling and feeling her smooth, hairless shemale sac with the other. So soft and feminine, yet so unexpected! I had to have more.

Mouth open, I zeroed in for my first taste of trans-cock. It was moist, throbbing, but it smelled lovely, a mingling of her perfume and deodorant, with a naughty, nasty under taste of salty sweat. I opened wide, eagerly and greedily cramming my mouth full of her cock. So long and hard, it tasted just right as my lips clamped down on the smooth skin, sliding her girth in and out of my mouth. My fingertips found the smooth, soft spaces beneath her balls and I teased her there and sucked her off.

It wasn't long before she too was on the verge, so she pulled out of my mouth then pulled me to my feet. Her hands found my cock again, and she came right across it, splattering my naked balls as she frotted our pricks together again, her pretty face clenched in an expression of soaring bliss.

Moments later and we were both quickly redressed, her blouse somewhat the worse for wear. I helped her step into her panties again, playfully tucking her surprise back into its silk sheath as she smiled.

She gave me her number and a kiss goodnight. Now, I just got to give her a call about that ass...

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byCeledriel© 14 comments/ 118299 views/ 67 favorites
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by Anonymous

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Such an exciting short story. You've laid the groundwork for a dynamite follow-up.
Even if you never finish this storyline, please keep writing. I really enjoyed your style.

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by donnaeliza2505/16/15

Hot and Wet

This was such a great story, I felt like i was there. Have to write more about their adventures. xx

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