tagTransgender & CrossdressersIt was Supposed to be a Quickie

It was Supposed to be a Quickie


I was in a strange place, around nobody I knew, and feeling the distance. I sat at the outside bar on the beach at a popular club in Key West. My name is Jenny and I was here for a week at least, escaping.

It was a beautiful night and even though I was suffering lonely thoughts and feeling like an outsider I could appreciate where I was at and the beauty surrounding me. The sun was setting and the red glow in the west was slowly fading away, the clouds capturing the last of the color.

I was half sauced and was not sure what I was doing here. I'd left Miami after Jason, my (now) exboyfriend had proven what a dick he could be and just run here .... it seemed a good port in the storm. It proved to be that ..... with no Jason around anyway, but there were none of my friends either. If you didn't count the little shit I ran down here with. She could be, well, exasperating to say the least. A slut she was, but I didn't begrudge her that as long as she had fun. Hell, I could be a slut at times, really it's like necessary isn't it sometimes? But she would leave you alone in a bar at the most inopportune times, some times when you really needed the company. Ahh well....she was Sammy, she was sweet, you had to love her.

The night was over half gone if you were going to sleep at all and the prospects were slim pickings. Just a few people around on this late midweek night. And I was horny .... again.

I noticed I was being eyeballed by this hunk that had the look of a guy whose days fishing was over and now he wanted laid. It was written all over his eager, little face. I sighed, knowing the revelation that lay ahead. Wondering which tack to take. The hunk might get more than he bargained for. Although honestly, that was okay. Maybe I could take him if he didn't like it, maybe not, but it might be fun if he struggled just a little as I started to work him over.

I am a big girl. 6'1 1/2" in my bare feet, pushing 6'4" or 5" in stilettos. Thing is, although I'm tall and carrying 168 lbs. it was all in the right places. I had beautifully formed legs that even I couldn't keep my hands off of when I was horny, muscular but not knobbly and so shapely and enticing in a micro skirt that fit just right for a waist that was small and tight like mine. With the eye watering proportions of the rest of my frame not to mention a bust that was enough to make a eunuch salivate, I was smoking. In short, I was hot ..... damn, I could even turn myself on, and obviously Jason was a fool popped to the forefront of my mind .... but hey ... fuck Jason. I was in Key West, he was in Miami and I was on my own. I would do what I wanted, to whom I wanted .... maybe even giving them a choice.

I gave the hunk a little help. A look, a smile, if that wasn't enough he didn't deserve to get any closer. It worked, he came over, I was a little disappointed. As he got up out of his booth to head my way the illusion of size that his musculature had fostered disappeared. Tonight I would really rather have been taken, ravaged, made to want it....to need it.... almost to be brutally filled. Looking at "the hunk" (he was now in apostrophes in my mind), that wasn't going to happen.

It's okay. I can go either way. I can be taken, ravaged, as I wanted tonight. Or I can take control .... I really enjoy that too, with the right, little, willing victim.

"So sailor," I purred, " What are you doing here?" Cool huh? The line was lame but I didn't really care. At this point he was meat on a stick and I was gonna bite.

"I don't know, God. I just got in a little while ago. Charter's over, boats all cleaned up, captain cut me loose." he grinned beguilingly. "How 'bout you?"

Jeeez he sure was cute. Needs a shower, maybe a shave .... but definitely looking good enough to turn out for at least a one night stand. I could already feel my nails raking down his back, a hard, taut, muscular, little back at that.

"I'm good, you need to catch up, what are you drinking?" I asked. I didn't give him the chance to offer. This was kind of the opposite of normal but so? I wasn't quite normal either, especially tonight .... he just didn't need to know how much yet.

"C'mon," I said, " let's get outta here."

So we grabbed fresh beers and wandered down to the beach and started walking. He seemed a little out of his element and I figured girls didn't pick him up every day. Although his musculature was tight and firm, ( I just wanted to jump on him, I couldn't help it, I was horny) he was a little dude. At about 5 ft. and 100 lbs. he was smaller than I was by a noticeable sum. But hey, if you were a guy like him and a girl (admittedly bigger) like me hit on you, what would you do? Say no? I didn't think so.

Is okay. I could salve his manly feelings, his anxieties with a little girl stuff. Guy's are basically easy. Just flash them a little or touch them a little and you can lead them by the dick wherever you want them to go. Of course it doesn't hurt if you're a hottie either. Almost never fails. I'm really surprised women don't rule the world. Maybe they do and the guys just don't know it.

I couldn't help myself. As we walked and talked I bumped up next to him and ran a hand over his rather plump, muscular, bubble butt. He grinned at me uncertainly and I tried to wake him up with a kiss, tongue searching for entry and the hand not holding a beer now energetically exploring his ass.

It evidently had been a while for my little buddy. He practically jumped on me. We landed in the sand and I thought, oh no, ..... not going there.

"Hey sugar," I cooed. "Let's go to my place. We just spilled our beer all over me and you both and I'm thinking a shower would feel great."

I jumped up, grabbed his outstretched arm and hauled him up into a tight clutch, both my hands now on that fine tail of his. I pulled him into my thigh, gave him a quick rub up and down and squeezed his butt cheeks with my strong hands. It was tasty just mauling him like this. I was fairly vibrating with the horns by this time. I smacked his shoulder, with his brown, doe eyes looking up at me and spinning I ran for the surf and plunged in.

Our clothes had to be washed anyway and the water would surely make them smell better than the beer if a little salty. He was coming in right behind me and tackled me. Down we went, him groping my tits and me with a hand on the front of his crotch caressing his growing member and the other still parsing the prize I'd awarded myself for the night...... his ass.

I slipped my hand into the back of his jeans, slid my hand down his butt and with my middle finger exploring his crack I hit pay dirt. (no pun intended) He stiffened slightly and his finger's grip tightened on my nipples, which really set me off, and I entered his pucker just slightly. Sliding out and down his butt I returned with crooked fingers and dragged a fingernail lightly over his rosebud with the rest of my nails trailing over his ass.

"Ahhhh," he cried, and my nipple now in his mouth suffered a teensy bite, although I sure couldn't call it suffering as I hunched, quivering over his mouth, and squeezed him back.

"Come on," I ordered him. "If we stay here I'm gonna rape you in front of everybody."

He knew that was supposed to sound good and it did... it did sound good, but somehow it didn't sound quite right and things weren't going exactly like any good night of fucking around he'd ever done before. He shivered just a little. Nothing ventured nothing gained he thought crazily. And she was one hot bitch, fuck!!

He followed Jenny out of the surf and struggled to keep up as she ran down the beach. This gal had long legs, a positively delectable ass, and a physique a champion runner would have been proud of. Johnny almost had his tongue hanging out by the time she slowed in front of a beachfront cabana. Dripping wet, horny as hell, starstruck a little, he decided on a frontal assault. Gonna just tell it like it is he thought.

"Sweetie, I swear," he rasped out. She had manhandled his package enough enough already so that he thought he knew her intentions. That bolstered his courage a bit and he went on. " I'm gonna do things to you that'll make you scream and you'll love it!" Johnny had it in him and he knew it. Not exactly where it was, but he knew he had it.

"Ooohhh," she laid it on thick. " What'cha gonna do to me baby?" She hungrily took in his fine, lithe form, the soaked clothing showed her all and her eyes lit up when she saw the pretty good sized dick outlined in his pants. She scraped her fingernails up his shaft, gripped it and squeezed.

"Oh shit," he said. "What won't I do. You know what I really want to do to you, right now, this minute?"

Hmmm, hmmm. Okay....I'm listening. This could be good she thought. As she stroked his cock she said, " What loverboy .... what do you want to do to me as badly as I want to suck your cock? Hmmm?" She had to giggle at the look on his face.

Trying to regain control, he stammered out, " I want to eat you just as bad as you do me, split your slit with my tongue, ream you out and suck down your juices." That was a mouthful he thought and he was proud of himself, he gotten it all out straight.

"Well," she said. " That might be just a little hard to do but we'll work something out, okay sweetie?" She looked almost fondly at him.

"What do you say we go fuck, baby doll," Jenny moan huskily. " Let's us get physical - real physical." His eyes widened and just saying the words made Jenny hotter, less in control. So she tweaked the little monster's dick she was teasing and bit his lip lustily.

She carried on, kissing him gently, still stroking a dick that was now rock hard. Then she couldn't resist rubbing his buns again, sliding her finger back down his crack, pulling him tight to her, always slightly to the side with her thigh in his crotch, bouncing his stiff dick on the muscles in her hard leg just a little.

"By the way, I'm Jenny ..... sweet cheeks," she whispered with her tongue in his ear. "What is your name anyway?"

He was cringing against her, her tongue driving him nuts. If she kept this up, he was gonna come in his pants. "Oh...oh Johnny....me ....that's me." he croaked.

Jenny laughed out loud, straightened up, hooked her arm in his and opened the door. "You look like a Johnny. You really do."

"What?" he cried. "What's wrong with Johnny?"

"Nothing baby," she crooned. "It's cute, suits you to a T." She kicked the door closed, pushed him up against the wall, got a handful of shirt with each hand and ripped it open!

"Hey.... hey!" Johnny wasn't so sure about this, he'd never been manhandled by a lady before. His eyes glazed over as her nails scraped over his chest and he found himself surrendering to the most demanding sex partner he'd ever played with.

"Shhhhh," she said. "Relax, I just wanted at your nipples baby." She sank down and captured one with her teeth, sucked on it, nibbled it, and tonguing it hard she ran her hands, nails and arms up his sides and around behind him. Enjoying the animal feel of him, she moved her mouth to his other little titty. Hard, muscular, flat little titties but with delicious nipples that were pointing up nicely. By the time she slid downward Johnny's breath was coming fast again and he stared enraptured at the top of her head and toyed with her beautiful, jet black hair.

Jenny grabbed his pants and with equal abandon jerked them down his hips. His cock got caught and flipped back up and would have smacked her but she caught it in her mouth and inhaled it, raking her teeth over it lightly as she drew back off of it, tasting it, sucking at it with her tongue. At that Johnny almost fell, his legs turning to butter, no strength to be had. She tightened her grip holding him in place and started making love to a most wonderful shaft. The little man wasn't small everywhere!

She was determined to pop his cork now. She wanted to taste his cum, always a thrill. She sucked his hot rod hard. She needed him with his limbs limp, compliant. And it tasted so good, felt so good to be assaulting his dick with her mouth. No making love now .... we're gonna be fucking!

It didn't take long when she really went to work on him. He'd been played with too long already, and the working over his dick was getting now by this captivating creature, was putting him on the edge of losing it all.

Then he did lose it. No apologies, he exploded, held her against him and filled her mouth with his salty come. He palmed her head gently as rocking against her he gently put fingers in her ears, softly moving them in circles inside her lobes. He was sure he was in love and certainly in lovely lust and now he had to bring her to that state too. This was the best sex he'd ever had in his life and he didn't want to give that up.

She came up off his tasty dick with come dripping off her tongue and she kissed him, opened his mouth with hers and as she tongued him gave him a mouthful of his own come. Her tongue dancing in his mouth, sparring with his tongue, they traded his come back and forth as she kissed him. He took it from her, tasting his jizz and went straight back at her and gave it back. Goooodammnn!! He was ecstatic, it just didn't get any hotter than this. These were his thoughts, but then, he didn't know everything yet did he?

He had his crotch, dick and balls pressed into her stomach and with his arms and legs, locked her up. She loved the way the little guy felt to her. And he had a really nice dick. He was all wrapped around her and she felt between them with both hands, found his nipples and pinched them hard in a quick burst. His arms and legs tightened in a quick convulsion as he hugged her hard, bit her neck, his chest rubbing across her breasts!

"Ooohhhhhhhh," she chuckled......... "that felt so goddamned good!".... Damn, she liked this little monkey!

Johnny was almost frantic to reciprocate. She hadn't gotten off yet. It was her turn and he slid down her body, got his feet on the floor and was just about the right height to attack her tits, which he did, like a starving man. Jenny grabbed his head and pressed him into her breasts, rubbing the nips side to side roughly across his seeking teeth and lips.

"Hey," she said. Raising his face and bussing his lips she bit down slightly watching his eyes droop in lust, she said, " Let's take a break and get in the shower. We still haven't made it past the front door."

He grinned stupidly at her. "I totally don't give a shit," he said.

Shaking her head at him she grinned back and said, " Well I do Johnny boy." She grabbed his shoulders, pivoted him, gave him a push and said, " Second door on the left, take your clothes with you and throw them in the washer, we'll turn it on later. Get in the shower and get it warmed up. I'll be there in a minute."

She watched the delectable, little butt walk down the hall. He looked at her as he turned to go in the bathroom and did a Groucho Marks eyebrow wiggle.

She bent, grabbed a shoe, threw it down the hall toward him and said, "Git!"

He ducked in the door and she heard the washer open and close and moments later the shower coming on. She started taking off the tight pants she had on, made worse because they were still half salt water wet. Finally she got them off and reached in her crotch to free the monster. That's how she thought of him anyway ... and always as a him. A good size tool to play with...... my little man. To violate little Johnny's ass with. She was pretty sure he'd be willing or almost willing, by now.

She stretched her limbs, loving the way she felt. Sex was so invigorating. You felt so goddamned good! So far she hadn't received anything, she was on the negative side of the cum roster. But her turn was coming right now and besides, she just loved to make a good man squirm. Make him holler and cum harder than he ever had. She knew it was a gift she had but maybe she was good at it because it was just so much fun. Shooting dicks and shuddering little boys.....hmmmmm!

She went to the bath and went in. He was covered in suds and he was scrubbing his hair, both hands busy, eyes squeezed tightly shut. He heard the door shut.

"Hey, get in here," he said, blowing bubbles with his words. "It's warm and I've got room for you right here behind me."

He couldn't see her evil little grin. Right behind him huh? Hmmmm? "Coming baby. Slide over 'till I get this door shut."

She pirouetted quickly under the spray and slid in behind him. He was covered in suds and her hands slid, slippery over him. Delving down his back, over his butt and into his crack. She slid her middle finger into his rosebud all the way to the hilt and leaving it there gripping his butt with her hand she reached around and grabbed his dick. She hauled up on him and raised him up on his toes.

"Hey, hey, hey," he cried. " What are you doing?" He felt her finger violating his ass joined by another, the soap suds making it all as slippery as need be. He'd already jerked on that cock of his before she got in here because he was already half hard when she grabbed him. Now it was hardening right up. Maybe he was just thinking of her and couldn't help himself. She decided she liked that one.

She eased him down off his tiptoes, slid her fingers in and out a couple more times, stroked his woody with a firm touch and let him go of him completely.

"C'mon," she said. " Let's get all this soap off of you so you can wash me." She took the wand off the wall and began energetically rinsing him down, pinching him in little jolts as she ran her hands up and down his tight little body. He was so damn cute, she thought. Too much so.

" I pronounce you clean," she said. "My turn." She dragged her nails up the backs of his thighs and smacked his butt ..... hard!

He laid back against her, rolled his head to the side, reaching up and capturing her lips, and kissed her sweetly. She reached for his nipples and pinching them lightly she pulled him tight to her as she pressed her fully erect cock into his round little butt.

He jumped. His eyes were wide looking back up into her face. "You... you've got a dick," he blurted.

And I thought you'd never notice she grinned to herself. She noticed he didn't struggle away from her, not that it would have done any good at this point, so she ran her hands down his chest, grabbing his sides and hips and she ground herself into him.

"Are you really a guy?" he asked somewhat timidly.

"What do you think?" she said. "I think I'm about the most woman you've ever had, aren't I?"

"Well yeah," he moaned. " But you got a dick, a big one!"

"Yeah I do baby .... but turn around here." She took him by the shoulders and spun him to face her. His eyes dropped immediately to the pole sticking up between them. His not so much smaller shaft was sword fighting with hers .... and losing he chuckled to himself. Wait, that wasn't funny.

" Hey you, look at me." Jenny pulled his face up to hers and kissed him soundly with her tongue playing in and out of his lips. She groaned. "I really need you to not care that I've got a dick just for tonight. I need you to like it. 'Kay honey?"

This was unreal he thought. But his libido was so strung out from the past hour with this woman he tried to not care. He reached out and caressed her shaft. Her big boobs with those delicious nips were in his face as he stared at the first cock besides his own he'd ever touched. But it wasn't a guy's cock, it was Jennys. And Jesus Christ she was all woman......well, almost all anyway, he temporized.

"Hey," Jenny said. "I need to get a shower taken. I'd really like for you to wash me." She hammed it up for him. " And I would really like for you to use those wonderful hands of yours to do it."

She didn't know if he was any good with his hands or not, she hadn't given him much of a chance to show her. Didn't matter, in her state, whatever he did would be fine launching point.

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