tagTranssexuals & CrossdressersA Night to Remember

A Night to Remember


Hi there reader. This is a new story of mine, and is one of what will be many attempts to break out and try to write in a very different category to the ones I'm used to. I will be giving several categories a go, many of which I haven't ever written in before, or in some cases even thought about. I hope you enjoy the experiment!


Christmas time. The jolliest part of the year, but for me it means only one thing: end-of-year functions, Christmas parties, big work dinners...every year it puts a bad spin on the season for me. All I want to do is start my holidays, relax for a while, and instead I have to sit through endless banter with people I spend too much of my free time with already.

Now I know what you're thinking, but no I'm not Scrooge, I don't hate Christmas, but when you're in a dead end job in a boring town it's hard to get excited. It's even worse when you end up getting dragged along to your dad's work function too. See, dad and his boss are old Air Force buddies, I get invited along a lot of the time, and at 22 I'm expected to make an appearance as a fully grown adult and friend of the family.

This year was particularly bad, since I'd broken up with my girlfriend about two months ago and was finding it hard living alone. Ok, so I say broken up with but what I really meant was she fucked my step-brother and his friend at my dad's house. I'm over her now -- no point being upset over a slut -- but at the time I broke my step-brother's nose. Needless to say I wasn't welcome there for a while and dad is still hoping to reconcile things.

So here I am, stuck at another party with dad and Janine -- she isn't MY mum -- with no date and, let's face it, going on my third month without sex. I mean, I think I'm fairly good looking: I'm quite tall, with tanned skin, a good sense of style and fairly gym fit without looking like I spend more time doing crunches and less time eating, or breathing, for that matter. The problem is there just aren't any decent girls around, not ones that you want to hold on to, and I just don't know if I'm really into the NSA side of life. For all that I am I'm also usually fairly shy around girls, at least to start with, so approaching one for a quickie isn't exactly one of my strong suits.

To be fair it wasn't a totally lost night...despite all that trouble above I ended up doing something I definitely have NEVER done before.

I'd made it about halfway through the night before I needed to get away from Janine's icy stares and dad's boss clapping me on the shoulder and joking about how I needed to be more like his daughter's fiancé, who of course was perfect apparently. Stepping out into the night and getting a breath of fresh air was such a relief. It was warm out, and dressed in a sharp blue shirt and blue tie I was quite comfortable. I walked away from the building a little and lit a cigarette, leaning against a light post. The function building stood directly opposite a big wooded park, and there weren't any other streetlights around, so it was all dark. But it was a full moon that night, and as the breeze kicked up it pushed away the dark clouds in the sky for a moment, and that's when I saw her.

She stepped out of the building next door, fully lit up in the moonlight, tall and slender, her long brown hair cascading around her shoulders and down her back, a few locks falling across her face. She wore a green dress, falling to about her knee height, with bare arms and a v neck, but not low enough to be too revealing. Around her slender waist was a black belt, with matching black high heels and a pair of stockings to finish the outfit. She carried a small purse with her, rummaging through it before she stopped and sighed, her shoulders sagging. Looking around, she saw me and slowly wandered over, stopping just outside the light of the streetlamp.

"Mind if I steal one of those?" she asked, one hand on her hip, holding her bag in her hand. I held the packet out to her invitingly, along with my lighter.

"It's a cheap brand," I said as she took two from me, "but it does the job." She shook her head to say it didn't matter and I caught a glimpse of soft brown eyes as she lit up, holding one smoke between her fingers as she stepped into the beam of the lamp to hand back my lighter, putting her own lighter and the spare smoke in her handbag. She was tall -- even if I was still taller -- and around my age too, perhaps only a few years older at the most. Her lips were a perfect pink, while her skin was smooth and a soft creamy light colour, touched by a mere hint of makeup to render her absolutely stunning.

"It's like anything life," she said, "a cigarette's a cigarette, and when you're all out anything will do." She blew a cloud of smoke out gently, her lips forming a perfect O as she did it. I felt instantly attracted to her voice. Something about her just stood out, like nothing I'd seen or heard or felt before. Being the quiet sort of guy I am I nodded, taking another drag as she did. We stood in silence for a moment.

"I'm Francine," she said softly, gazing at me. "Everyone calls me Frankie. What's your name?"

"Alex," I murmured back.

Looking over her shoulder at the building, Frankie glanced back at me. "Christmas party Alex?"

I nodded. "Dad's, boss is a friend of the family." Frankie nodded slowly, listening as I explained their connection, along with my particular distaste at being there with my stepmother, leaving out the exact nature of it all. Her eyes bored into me, making me feel slightly intimidated, but in a good way. Despite my shyness I was a comfortable flirter and she didn't mind, flirting back a little as we stood under the light. We chatted a little more about the work I do since this wasn't my work's thing, and I found out her beef tonight was with one of her colleagues who wanted to get a little closer but didn't know how to approach it right. She preferred the kind of guy who could take control, but knew how to act around a lady. Being single for a fair bit of time now, I pointed out that I had recently dealt with a girl with an attitude problem too, and how sometimes you just have to push this sort of crap to one side and move on, ignore the troublemaker.

"It's more than him...I just can't stand these things, work functions. All your co-workers getting drunk, boss is busy pretending to associate with you and you just get so fucking OVER it all." Frankie sighed, the tinge of what had probably been free sparkly on her breath, but she wasn't slurring; this girl could hold her liquor. She took one last drag, dropping the smoke and looking me up and down. "Are you as bored as I am?" she asked, stepping on the cigarette with the toe of her high heels.

Her question threw me a little, but I nodded, wondering what would happen next. She gave a flirty little smile and stepped a bit closer.

But you're going back in?" Again, I nodded. "Well why don't we have a little fun in the park instead?" I blushed as she glanced over to the park opposite the buildings, feeling a tension in my pants as ideas raced through my mind. I had hardly known her for ten minutes! I'm sure she could tell I was nervous, but she stepped close to me and rested her hand on my crotch, feeling how hard I was for her as she took my smoke, taking a long puff on it. She placed it back in my mouth and I could taste the faintest trace of her on the butt. My cock pulsed under her palm and she smiled naughtily.

We heard a noise from the building -- the door leading back to her party opened and a man stepped out, looking around, a slight wobble visible in his stance. Frankie quickly took my hand and pulled me towards the park, dropping my smoke as we ducked into the shadow of a large tree. The man stood there looking for a few more seconds, then turned and disappeared back inside.

I turned to look at Frankie. She was leaning back against the trunk of the tree, one heel braced against it, looking at me invitingly. For all my shyness I moved forward, enticed by this unbelievably sexy girl. My hands slid around her waist as she reached up behind me and pulled me to her, pressing her lips against mine in an amazing kiss, long and soft, willing me to push her back harder. My hand slid down her waist to her hip, gently caressing her ass as she moaned into the kiss, one hand moving down to grip my cock through my trousers. Suddenly she pulled away, and took my hand, looking a little bit nervous herself.

"What's wrong?" I asked. She bit her lip, then looked around and, leading me by the hand, took me further into the park towards a long bench in the open.

"Here," she said. "Much better." Dropping her handbag, she sat with me and kissed me again, hungrier, rubbing the front of my trousers aggressively. She pulled back and I felt my fly go down slowly, her slender hand reaching into my pants and pulling my cock out of my boxers. I sighed as her fingers wrapped around my shaft and gave it a few gentle pumps, kissing me hard, her tongue finding mine. In one swift movement she pulled her tongue from my mouth and leaned over, her lips sliding smoothly down my cock, sucking on my head. I gasped with shock and pleasure as she bobbed her lips up and down, getting more of me in with each movement until her nose pressed gently against my thigh.

I was really enjoying her sucking me off, but just as she got into a rhythm she pulled back and took my free hand, guiding it to her belly.

"Do you like that?" she asked. I nodded vigorously. Her dress was so soft to the touch, her belly tight and smooth beneath it. She slid my hands down, over the wide black belt around her midsection. "You want some more? You really want me?"

"Fuck yes," I moaned. She was amazing, her hand jerking me off as I felt her push my palm lower, over her hips and towards her crotch. I bit my lip as she leaned back, her nipples poking through the dress at me.

"Touch me..." she breathed. God I wanted to touch her so bad. Her hand still on top of mine, I leant forward and slid my fingers down her dress to rub between her thighs and felt...something.

I had been expecting a tender wet patch soaking through her underwear, but instead my fingers slid down the length of a long, hard, warm object, the fabric of her dress hiding nothing from my touch. 'Hard? Warm?' I thought to myself. I looked down in absolute shock, confirming what my fingertips had told me; there was a distinctly hard outline beneath the hem of her dress! Her hand closed mine around the hard length of the object and, as if I hadn't already guessed what it was, it pulsed in my hand, reacting to being held.

"Y-you're...you're a chick with..." I stuttered. She just looked at me, her brown eyes mesmerising in the moonlight. Despite my apparent shock I never felt the urge to remove my hand from her groin, her fingers tightly wrapping mine around her member through the dress. What's more, I was still hard, and her hand slowly worked up and down my shaft as if to confirm that even though she had extra equipment, her efforts had made me desperately horny.

Frankie gave me a slow smile, then without another word she leant back over and took my cock into her mouth again, parting her lips around it lovingly as she slid it all the way down her throat. Unable to contain my excitement, I sat back on the bench, letting her suck me as she let go of my other hand and reached up under her own dress. A moment later she moaned around my cock as her hand slowly moved back and forth out of sight. Part of me was curious and a little unsure about seeing what she was doing, but my pleasure had gotten the better of me so I just sat there, feeling her tongue curl around the head of my dick.

My God it felt good. It had felt good before I knew what she was and it was still good now, and hers were definitely the sexiest pair of lips to ever service my meat like this. I let out a moan as she gave me an extra hard suck. Frankie's hand was pumping me hard now and she looked up as she worked, sensing that I was getting close to cumming. She held the base of my shaft and sat back up, looking at me lustfully.

"Can I sit on it?" she asked, giving me a squeeze.

I could hardly talk. I just stared at her, shocked. Getting a blowjob from a hot chick's mouth was one thing, but fucking her...I honestly didn't know whether I was curious enough to try it, what it might feel like to let her. She must have been able to tell what I was thinking because she sat up and grabbed her handbag, taking out a little bottle of lube and squirting some into her hand. Smiling at me, she reached down and rubbed it up and down my cock, slicking it up. Then she put her handbag down and stood up in front of me, her package making a noticeable tent under her dress as she leaned over and pulled her panties down, stepping out of them and turning around.

As I watched her, a slender hand lifted the back of her dress up, revealing a perfectly round, smooth ass, good enough to eat. Frankie reached between her legs and took my cock in hand, guiding it to her opening as she backed up over me, her legs on the outside of mine. The head of my slippery cock bumped gently against her puckered hole, and in slow motion she lowered herself down and I felt her asshole give way to my shaft, felt it slide up inside her until she was sitting in my lap and I was engulfed by her cheeks.

It was unbelievable. I felt her moan vibrate down through her sexy, slender body and into my crotch as she slowly rolled her ass around on my lap, adjusting to me being inside her. It didn't take long for her to get impatient, however, and she started to lift herself up and almost all the way off me before slamming back down, driving my hard cock deep into her ass. I gasped, almost paralysed, as she started to ride me, slowly getting faster and harder, pushing her hips down on me to get deeper with each thrust. I felt her hand grip my leg in front of her for balance, but I also felt something else -- a rhythmic movement coming from her other hand.

Timidly I reached around the side of her hips -- God, those soft bumcheeks were divine! -- and felt that the front of her skirt was up. My fingertips reached out more and suddenly I could feel a soft, warm fleshy pouch where her pussy should have been. Very slowly, I moved my hand further around and gently clutched her balls, feeling them up as she rode my cock. I could feel the pinkie of her other hand as it moved up and down her own throbbing member, bumping my hand with every downstroke. She moaned as I caressed her, speeding up with both her tugging and riding.

As suddenly as things had gotten to this point, I felt a familiar boiling in my groin. Unable to speak, I released Frankie's balls and could only grip her soft, exquisite sides tightly as she bucked wildly on top of me, moaning loudly to herself. Her long brown hair was brushing over my face as she leant her head back and bounced up and down, and I could smell her perfume as one hand trailed up to slip inside the top of her dress. My fingertips felt perfectly soft flesh and a hard, responsive nipple and my brain had just enough time to register how real it felt before my balls noticed how perfect she was and I let out a strained groan, blowing my wad deep inside her ass. I shut my eyes, gripping her even tighter as I went completely rigid. Frankie leaned back further, pressing her shoulders against my chest as she ground her bum hard into my lap. She was crushing my stiff body against the bench as she panted on top of me, my shaft pulsing as it pumped my cream into her waiting hole.

"I...I can feel it...oh God..." she gasped with delight, her soft cheeks planted firmly into my lap as I came. It was as though I had died. All I could feel was her ass, squeezing around the very base of my shaft as she let out a long moan of her own and pressed back against me very hard. Her nails dug into my leg and I had just enough consciousness to open my eyes and tilt my head forward to see her arm jerking, a long, sticky string of white spunk flying out before her, landing on the grass in front of the bench. She shot two more loads as I filled her from behind before I felt the rest pooling on the inside of my thigh, slowly dripping down between the gaps in the wood we sat on. Her ejaculation finished a moment before mine, my hot, quivering member dumping one more thick blast of cum in her ass as she breathed a sigh of relief on top of me.

"Whew. Now...that's a party." She breathed, turning her head to lightly kiss my cheek, her hand seductively rubbing my thigh. "Oh wow, I haven't felt so full in a long time..." I felt her hand slide around her body, her slender fingers intertwining with mine as she took my hand and squeezed it, lifting it and holding it against her belly -- as a lover would. I didn't speak. I couldn't, even as she turned around and took my head in her hand, stroking my cheek as she planted her soft, wet lips on mine for a long, hot, kiss. Her tongue entered my mouth and found mine, lashing it lovingly before she pulled back, letting it slide from between her lips. She smiled at me, looking deep into my eyes with joy and fulfilment before she turned and lay back down, catching her breath.

"Mmmm...feels good to be so...stretched..." she purred, rocking her bum side to side in my lap, my cock shifting against the cum soaked walls of her insides as her sweet scented hair lightly caressed my face. Her hand still held mine, resting my palm on the soft material of her dress, hiked up around her waist, the rise and fall of her stomach slowing as she tried to calm down from her orgasm.

A few minutes later Frankie gingerly sat up, letting go of my hand as it drifted down her side. With a sigh she reached back, gripping the base of my cock as she slipped it out of her hole. It made a slight slurping sound as my head withdrew, eliciting a quiet gasp from her. She stood and now I could see my cum leaking out of her spent opening, running down her leg, along with her massive cock slowly wilting in front of me. My own piece was covered in my cum and still pointing skyward as she slipped her panties back up over her perfect ass and turned around, smoothening her dress down over the tool she shouldn't have had. She looked up at me and smiled that sexy smile, completely a woman again, her tit showing slightly from where I had pulled her dress to the side, a hard, pink nipple pointing at me.

I don't know what came over me. I guess part of me felt amazed that she had gotten off from the feeling of my cum gushing into her butt, yet even as I thought it I felt a hint of fear and uncertainty seep into my head as the full reality of my situation sank in. As such, I quickly pulled my boxers up over my cock and did my pants up, barely hearing her soft, feminine voice as she elaborated on her enjoyed pleasure. I nodded absentmindedly and turned away, finally noticing the rather large puddle of fresh cum on the grass, shining brightly in the moonlight, as if I might have missed it somehow. I had started walking back towards the building and the boring Christmas party awaiting me when I heard her speak again.

"Thanks for the smoke, Alex," she purred. In accordance with some strange desire that had overcome me tonight I turned to face her again, watching as a vixen in a slim, green dress, her brown hair falling magically around her shoulders, lighting up the second cigarette I had given her with well manicured hands, holding the stick in her fingertips as she blew out a cloud of smoke from between those perfect, pink lips. I remembered the feeling of those lips on mine as I turned to go, her brown eyes boring deep into me every step of the way.

When I got home from the party, after dropping dad and Janine back at their house, I sat down on the bed and fell backwards, asleep before I had even changed. In the morning, after the gentlest night sleep I had enjoyed since my break up, I woke with the most raging, desperate hard on I can remember ever having, along with a sudden, painful realisation tinged with regret that I never got her number, and that I couldn't remember the name of the company she worked at. I couldn't remember anything, except for amazing brown eyes, soft pink lips, and her name...Frankie.

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byMaster_and_Sex_Kitten© 8 comments/ 45823 views/ 27 favorites

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