Hogmanay

Story Info
An unexpected encounter with a sexy trans.
5.1k words
4.67
15.8k
47
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is a work of fiction. It involves an encounter with a female transexual. Nobody is forced to do anything and there is no element of humiliation. If you need either of those things in stories of this kind, this isn't for you.

*

"If you're really going to do it, you've got to go to Scotland." That's what all my friends said when I broached the idea of getting out of London for New Year. So that's what I did. I booked a cheap B&B in Edinburgh (though 'cheap' here is something of a relative term at that time of year) and a ticket for the celebrations. A few months later there I was, in Prince's Street Gardens in the closing minutes of the year. Thankfully the weather had remained dry, though bitterly cold - the wind blowing off the North Sea and roaring up from Leith is biting enough to freeze your balls off if you don't dress for the cold. I'd had a great evening. The atmosphere was fantastic. The music had been exhilarating and the nips of whiskey I'd had from my hip-flask had certainly eased my inhibitions.

This was exactly what I needed. A month or so previously my long-term girlfriend Rachel and I had split up. I say "split up"; the fact is that I caught her in our bed with a guy from her office. I walked in to find her impaled on his cock as he was emptying his balls inside her. After our being together for four years that came as a bit of a shock. She moved out the next day after spending the night with her mother. Since then I've felt alternately angry, lonely and horny. I suppose, if I'm honest, I knew there was something wrong with our relationship. I suppose, too, if I'm honest, in the following weeks I nursed my anger, basked in my loneliness and obsessed on my horniness. In short it had been a while since I had really let go and just allowed myself to enjoy myself. Now here I was in the excited crowds in, soaking up the atmosphere, sharing in the laughter and moments of shared dancing, and enjoying the bonhomie.

By the time they started counting down to midnight I was in the best mood I had been in for weeks. The castle was lit up and everyone was waiting for the gun. The crowd were chanting down the seconds and the band on stage were already playing the intro to Auld Lang Syne. Three. Two. One. The gun thumped and the crowd roared. I turned to my right and there was a gorgeous young woman with blonde hair in a bubbly perm wearing a gold coloured pleated, padded jacket. She turned toward me at the same time and we embraced. Without thinking I planted a kiss on her full, red lips. It was on the spur of the moment. I know you don't do that sort of thing. I get the whole sexual harassment thing.

"Sorry!" I mumbled pulling away from her. "Got carried away for a moment. I'll..."

She looked me up and down. Then she smiled and said in a lilting Scottish accent, "That's OK. If I'm gonnae get molested I could do worse." Then she put her arms around me and kissed me back. I felt her lips part and her tongue slipped cheekily into my mouth for a moment before she pulled away again. "I take it, from your accent, that you're no' from round here. Not that that's unusual at this time o' year."

"London." I answered. "My name's Colin."

"Michelle," she replied. She gave me a broad smile and continued, "Well Colin, as my friend seems tae have found something - or someone - better to do, why don't we watch the fireworks for a bit, then find ourselves a bar?" She put her arm around my waist and I slipped mine around her shoulders and we both looked to the sky as it exploded with light and sound and colour. Edinburgh doesn't skimp on fireworks so it was a really impressive show, but after a few minutes Michelle took my hand and just said, "Drink" and began to lead me away.

She led me from Prince's Street Gardens to the far side of the castle and an area known as the Grassmarket. There we found a bar and went in. It was a simple sort of place - a few tables, wooden floor, plain decor. I went to the bar and ordered a pint of lager for myself and a gin and tonic for Michelle. While I was waiting I looked back at her. She was taking off her padded jacket and hanging it on the back of her chair. She was wearing a mid-brown Fair Isle sweater and a knee-length red skirt. Both managed to somehow hide and enhance her curves. There was clearly a pair of substantial breasts beneath that sweater and her curvy backside suggested that the rest of her body complemented them.

Returning with the drinks I took off my coat and hung it on the back of the chair and sat down. We drank our drinks and we chatted. She told me a little about herself - her job, what she liked to do - and I did likewise. All the while I kept looking at her face - round and open with generous, full lips and big blue eyes the colour of cornflowers. At last she finished her drink and asked, "Do you have somewhere to go tonight?"

"I've got a B and B out at Corstorphine," I replied.

"Oh. Corstorphine?" she said smiling at my pronunciation, putting the emphasis on the second syllable and pronouncing the third as 'fin'. "You'll find it hard getting a taxi tonight and that's a bit of a hike." She got up from her chair and took her coat from it's back. "My flat's a lot closer. Get your coat," she said, a broad smile spreading across her face. "You've pulled."

Her flat was in an area called the Lawnmarket. It was on the third floor of an old tenement building. At the top of a narrow, dimly-lit stairway she turned her key in her door and let us in. A short corridor led us past three doors to a small darkened living room. Michelle turned on a small lamp in the corner of the room to reveal a comfortable two-seater red settee, a coffee table and a few other simple furnishings. "Sit down," she said, directing me to the settee. "I'll just be a moment". I did as she said and she disappeared for a few moments, returning with a partly-consumed bottle of Merlot and two glasses. "Pour us a drink," she said, putting them down on the coffee table. "I'm just going to freshen up a bit."

While she was out of the room I poured the wine and had a look around. She had a few books on a bookshelf - mostly detective fiction - and a few DVDs sat next to her television. I picked them up and looked at them. Looking out of the window there were a few fireworks still going off. I picked up a couple of ornaments and examined them. Then I sat down and began to sip my wine. After about ten minutes Michelle returned. She was dressed only in a white towelling dressing gown and she looked gorgeous. I lifted her glass from the coffee table and proffered it to her and she took it from me and sat down beside me. I put my arm around her soft shoulders and she snuggled up to me, curling up on the seat beside me. I kicked off my shoes and socks and enjoyed feeling the warmth of her body.

We drank our wine fairly quickly, exchanging kisses between mouthfuls. I finished first and, setting my glass down on the coffee table, I slipped my hand beneath her dressing gown and cupped her left breast. It was full and firm, her skin smooth and warm and her nipple hard under my hand. "Mmmm..." she murmured. "I like that." She unbuttoned my shirt and ran her hand over my chest and stomach. "That's very nearly a six-pack there," she whispered. "At least a four pack." I felt my cock responding to her touch and I kissed her again. Her lips parted and my tongue rolled over hers. Abruptly she broke away and downed what remained of her wine. "Time to take this party elsewhere," she said and got up off the settee.. Gesturing me toward the door she turned off the lamp as I stepped into the corridor.

A few seconds later we were in her bedroom; my shirt was off and Michelle's hands were at the waistband of my trousers. Our lips locked and I ran my hands inside her dressing gown. I could hear her breath getting faster as I caressed her fine, full breasts. I felt my trousers coming loose and them being pushed urgently over my backside along with my underpants. The backs of my legs were against the bed so I sat down to take off my trousers. At the same time Michelle stepped back a little, untied her dressing gown and, shrugging it off her shoulders, allowed it to tumble to the floor. For the first time I got a look at her naked body: her magnificent breasts, the beautiful curve of her stomach, wonderfully rounded hips that spoke of a bum I would really want to get to know. And a six inch penis jutting out from her groin at near full erection.

I sat there, open-mouthed, in shock for a moment. I must have looked like an imbecile. "Shit! I'm sorry. I thought you realised," Michelle was saying. "I thought I'd dropped enough hints."

My brain was whirling. There were things she had said during our conversation about 'not being like other girls' and 'having a bit extra' over most women. I'd simply dismissed them as the boasts of gin and wine. Damn - she'd even mentioned hormone treatments. "It's just," I began. "It's just I've never been with..." I was going to say 'a man', but when I looked away from her groin to those gorgeous breasts and the softness of her curves; to the fulness of her lips and the cascade of curly blonde hair I saw something else. Then I looked into those big blue eyes. And that was it.

"You can sleep on the settee, if you like," she said bending to pick up her dressing gown. In response I stood up and, smiling at her, opened my arms and gave a "come here" gesture. She gave me a sultry, suggestive grin and stepped toward me and slipped her arms around my waist. "You're sure?" she asked and I took her soft, sensual body in my arms and pulled her close. I pressed my lips to hers and our tongues lashed at each other. My hands drifted down and cupped her deliciously soft arse as she stroked mine and pulled me closer. It felt so strange to feel her firm breasts pressed against my chest and, at the same time, to feel her hard cock against my stomach, but now I was so caught up in the new experience and the familiar sense of lust that I scarcely questioned it.

I sat back down on the bed, this time Michelle, her legs astride my thighs was sitting on my lap. Her breasts were right in front of my face and I rolled my tongue over one nipple then the other and I heard Michelle moan softly. She slipped her hand between us and wrapped her soft warm fingers around my now very rigid cock and a shiver of pleasure rolled through me. "Mmmm..." she said huskily. "Someone's pretty sure about this". She moved a little and gathered her own hard shaft into her hand together with mine. It felt so strange, so different but incredibly erotic. We rolled sideways and were lying together on the bed, exploring each other's bodies, my hands thrilling to the satin smoothness of her warm hairless body and her hands eliciting excitement enough to make my shaft as hard as steel.

There came a point when Michelle was on her back and I was stroking her stomach and nibbling her nipples and I went into auto-pilot. I began to kiss my way down her body - as I had done so often with Rachel - and getting closer and closer to what was between her legs. I could hear her breathing growing faster and her stomach muscles jumped in that familiar, excited and exciting way as my lips and tongue moved down her body. At last I came to her cock. It was so hard and seemed to tremble as I got close to it. Here was a point of no return and I knew it.

I have always thought of myself as straight - I still do - but many years ago, when I was about nineteen, I was sitting in a cubicle in a public toilet. There was a piece of toilet paper hanging on the wall of the partition between my cubicle and the next. It covered a hole and, as I was cleaning myself up, the toilet paper fell away and a semi-erect penis was pushed through the hole. I knew what it's owner wanted, of course, and I panicked. I pulled up my trousers and fled the place as fast as I could. Yet I was left wondering, all these years - what would it have been like if I had stayed? Now here I was, about to know. This time, though, I had kissed my way down a beautiful feminine body to get to the point where I was about to take a cock in my mouth.

I felt Michelle's soft hand gently caressing my hard shaft while her other stroked my hair. "Yes..." she whispered and I took her magenta tip into my mouth. I rolled my tongue over it and tasted the saltiness of a drop of precum that seeped from its tiny slit. Slowly I took more and more in, my lips tight around his shaft, enjoying the feeling of her skin moving against them, the sound of her moaning as I retreated, sucking as I went. "Shit yesss..." she murmured as my mouth began a second descent down her shaft, enjoying the sensation of the ridge on its underside running along my tongue.

Then I began to suck her cock in earnest. My mouth moved up and down its length in a regular, rhythmic way, feeling my cheeks hollowing on the upstrokes and my cheek brushing her skin on the downstrokes. All the time her left hand was playing with my own rigid dick and straying up to my sensitive anus. Driven on by the newness and excitement of it all I managed to take her whole six inches in on each stroke, my nose descending to the tight, naked skin of her balls. Responding, perhaps, to her own activity around my bum I pushed the tip of one of my fingers into her knothole.

That's what took her to the edge. I could hear her gasping and her strokes on my shaft became more frantic and more irregular. Her legs began to tremble and I could see, from the corner of my eye on the upstroke, that her other hand was grasping at the bedsheet. Was I going to do this, I thought for a moment. Was I going to take cum in my mouth? Then I began to suck a shade more determinedly. I felt Michelle's cock swelling and straining between my lips, her hips rising from the bed. I heard her moaning, "Uuuugghhhnnnn!" then a burst of warm, thick semen filled my mouth. It was salty and, I thought, a little sweet. I swallowed as another pulse followed the first and then there was another, each followed by a sweet little cry of happiness from Michelle.

At last I had emptied her and I flopped back on the bed beside her, my tongue coated with, and still tasting, her hot sticky cum. I could feel some on my chin and around my mouth where I had been unable to contain it all. Sensually Michelle rolled onto her side and snuggled up to me. Propping herself up on her arm, her breasts pressed to my chest and her soft hair caressing my cheek, she leaned over and kissed me, her tongue sharing the savour of her semen with mine. "Oh Sweetie," she said at last. "That was brilliant. You deserve a treat after that."

Rolling over she reached into a drawer in her bedside cabinet. From it she took a pink plastic tube then she rolled back over and handed it to me. It was a lubricant jelly of some kind. "Strawberry flavoured," she said as she got an all fours on the bed, her legs parted and her limp penis hanging beneath her soft feminine stomach. I was struck again by how beautifully round, smooth and feminine her bottom was. I gently stroked it, then opened the bottle of lube, squeezing a little onto the tips of the fingers of my right hand. Delicately I parted her cheeks with my left and applied the slick, slippery gel to her cute, pink anus. She sighed a little and said, softly, "Make sure it gets inside," so I pushed my index finger inside, eliciting a soft moan from Michelle's lips.

I applied a layer of cool, unctuous lube to my rigid cock and held its swollen tip to Michelle's knot-hole, then, with a gentle but insistent push I sank it into her beautiful rear. I heard her breath trembling as my shaft slip through her sphincter as it clutched at it convulsively. She sighed as I began to thrust my hips forward and back, driving into her and retreating, thrusting my cock deeper and deeper into her delectable rear. I'd tried anal with a couple of girls over the years, but neither seemed to enjoy it - especially Rachel, for whom one time had been enough. What I was experiencing now, though, was something quite different. Michelle was moaning gutturally as I impaled her again and again. At last my whole length was inside her and my groin was pounding at the soft rounded cheeks of her arse.

"Oh fuck yes!" I could hear Michelle moaning over and over as I began to pick up the pace and to drive my rod into her with greater frequency and greater force, maintaining a steady but increasingly insistent rhythm. I reached around her and took her round, firm tits in my hands as my cock moved to and fro in her warm, yielding back passage, her anus gripping its girth. At length, with a quivering cry Michelle fell forward onto the bed to lie flat on her stomach, her face buried in the pillow. Harder and faster I ploughed her arse. She was clutching, clawing, the sheets, her knuckles white. Then, for a moment her breath seemed to stop, her body shook beneath me, then she let out a wail. Her sphincter convulsively gripped and released me, as if her arse were milking my cock. Successfully. Wave after wave of pure unadulterated pleasure roared through my shaft to fill my groin, my spine, before exploding in my brain as I emptied my seed into her.

We lay panting on the bed. I rolled off, my softening manhood slipping from her soft, smooth arse., to lie on my back beside her. "Wow!" she said, propping herself up on her elbows. "Just wow!" She leaned over and kissed me gently on the lips before returning the lube to the bedside cabinet and turning the bedside light of. We slipped beneath the duvet and she snuggled up close to me, her soft, feminine body warm against mine. Spent, I nodded off.

I may have slept for an hour so. Then I woke and lay in the darkness, my brain on overdrive processing what had happened. I turned over and over seeking sleep but it eluded me. At last Michelle turned on the bedside light and propped herself up on one elbow. "Cannae sleep?" she asked. "Feeling guilty?"

"No," I replied. "Not even a little bit." And that was true. I kissed her, softly, on her full, generous lips then lay on my back thinking for a moment before I continued: "When I was... inside you...earlier. You really seemed to get something out of it." I explained that neither of the women I'd tried anal with before had seemed quite so enthusiastic.

"Aye," she said with an amused grin, "it doesnae happen every time, but when it does it's fantastic." She went on to tell me about prostate orgasms; how they are different from penis orgasms and a little about how they felt. She gave me a knowing smile and said, "You seem very interested in this." Then she snuggled up close to me and caressed my stomach, sending little thrills through my abdomen. I could feel her warm breath at my ear as she whispered, "Are you wanting me to fuck you?" There was something about the lascivious way she pronounced that word in her husky, feminine Scottish brogue that sent a jolt of excitement the length of my body. Before I'd even thought about it I had said 'yes'. "In that case," she said, throwing back the duvet and getting off the bed, "there's a wee ritual to carry out." She offered her pale, soft hand to me and I took it, letting her lead me through to the bathroom.

While she ran some warm water into the handbasin she cupped my balls in her soft, delicate hand and brought my cock back to an impressive rigidity. Then, when she had added some shower gel to the water, she took an object from the bathroom cabinet beneath the basin and showed it to me. It was a rubber ball with a long, tapering nozzle. "D'ye ken what this is?" she asked.

I looked at it for a moment and replied, "It looks like a thing my Dad has for blowing dust off the mirror in his camera."

Michelle failed to contain a short laugh. "We'll not be cleaning any cameras with this when I'm finished with it." Squeezing the rubber ball and releasing it she sucked some water up from the basin then, guiding me to stand with my legs astride the toilet bowl she got me to bend forward a little. Then, squatting next to me, she parted the cheeks of my arse with one hand and eased the end of the nozzle into my arse than, with a firm pulse, she squirted warm soapy water into my rear and I felt it flooding my anal channel. "Hold it!" she said, guiding me to sit, "And let it go". We repeated this another couple of times, her soft hand stroking my arse and stomach all the time. It may well be the most intimate experience of my life. "And now," she said stepping in front of me as I sat on the toilet, her semi-erect cock right in front of me, "You'll be all sweet and clean for my wee pal here."

12