Holiday Girl


Everyone says you should go on holiday to get laid. I'd never found that to be particularly true, or maybe I was too choosy to fuck the drunken 18 - 30 crowd. I liked a bit more than a quickie with some chubby office girl spending her money on cheap Spanish booze and so desperate to get a suntan she ended up looking like an under-cooked steak.

I prefer a conversation that is more than a shouted exchange across some club dance floor about the latest TV soap. Maybe Spain wasn't the right place I told myself. Perhaps I'd made a mistake coming here. Still it was cheap enough, a last minute booking in a reasonable hotel and there were some interesting and historic parts once you left the immediate beach area and explored the hills and villages that overlooked the hotel strip.

I'd been out cycling that day. I'd hired an off-road bike and gone up into the hills and had a great day climbing and descending some of the tracks. Now, showered and changed, I was relaxing by the bar near the pool. There weren't many people about at that time of day. They were either getting ready for a night in the clubs or were sleeping off a day's drinking, getting ready for more later in the night. One girl did catch my eye though. She lay on a lounger on the other side of the pool. Stretched out on her front, she was propped up on her elbows reading a book. Her dark brown body was coloured deeper than any tan.

I thought she must have had a least one black grandparent. She had long shapely legs that went all the way up to a really nice rounded arse - I do like a nice arse. Her long black hair fell over well shaped shoulders and almost down to her slim waist. Her fit figure was emphasised by a little white thong bikini which left her cheeks bare with just a thin strap between her legs and around her waist. She was topless and I could just see the swell of a neat perky little breast. I started to wonder how I could get to know this girl. How could I approach her without seeming too blunt or eager?

As I watched a man lay down on the lounger next to her. Just my luck I thought; a nice looking girl who actually reads books. It was inevitable that she'd have a man around somewhere. I watched them chatting. She seemed to keep shaking her head and trying to carry on reading. Soon she turned away from the man, sat up, put a towel round her shoulders, wrapped a sun dress round her waist, picked up her bag and walked towards the bar. Interesting body language I thought, they must have had an argument because she ignored the man and he just watched her tall shapely body walk away with no attempt to follow and a sulky look on his face.

Closer too she was even sexier looking. The sun dress she wore hardely reached the top of her legs and her breasts pressed out against the towel that covered them. She walked towards where I was sitting. I realised I'd been staring so I smiled and said, "Hi." She smiled back and returned my greeting with a quick look at me that seemed to read my soul and then a modest look down as if she regretted being so forward. Her long black hair fell over her shoulders and beautifully complimented her dark skin. It was now or never. I had to say something. I said the first thing that came into my head.

"What are you reading?"

Damn! Of all the great chat-up lines in the world that one ranked somewhere in the bottom 10 percent. She stopped by my chair and looked at the book in her hand.

"Oh it's just a novel," she said. "Nothing too challenging for holiday reading."

Her voice was rich and warm with just a trace of a Caribbean accent. She showed me the book. I recognised the author as one of the celebrated modern literary novelists who received favourable reviews in what used to be called the broadsheets.

"How about you?" she asked.

I told her I was reading a history of Spanish art. Damn again! That sounded so pretentious. Why didn't I just say I was reading a novel too? Idiot!

"That sounds interesting. I don't suppose there's much of it to see round here!" She laughed and I felt better. Maybe it wasn't so off-putting. Her eyes sparkled when she laughed. She had a very attractive smile. In for a penny I thought and made the big gamble.

"Perhaps I could buy you a drink if you'd like?" She considered this for a moment and then said

"That's sweet of you but I'm not really dressed for it. How about we have a drink before dinner - say 7.30, here?" Oh yes! My grin must have been obvious because she went on to say

"I'll take that as a yes then!"

"Yes, yes that would be great. Ermm - what about him?" I nodded to the guy by the pool.

"Him? Oh he's just some macho arsehole I never met before. He wanted to know if I'd like to sit on his 9 inch dick." Her face showed amusement and no embarrassment. I supposed she must get propositioned like that all the time.

"Jesus! What did you say to him?"

"I told him if it was that long he could bend it in half and go fuck himself with it!" We both laughed and then she smiled and said "See you later OK?"

I watched her walk towards the lobby. The light was shining through her thin sun skirt showing two lovely rounded arse cheeks and a narrow waist that undulated enticingly as she walked. My mind went into overtime. We'd have pre-dinner drinks. I'd invite her for dinner; she'd be stunned by my witty but serious personality. I'd touch her hand and she'd respond, we'd walk along the beach in the moonlight, I'd kiss her and feel her becoming excited and then we spend the night in my room fucking until breakfast. Idiot, I thought. She'll probably tell me to go and bend my cock in half too.


I was ready and waiting at a table. A few minutes after 7.30 she walked into the bar and you could tell from the sudden change in the tempo of conversation that everyone noticed her. She was wearing a long, light silky evening gown which left her shoulders bare and might just as well have left everything else bare too because you could see her braless breasts and nipples clearly outlined under the smooth top. I stood and went to meet her and felt jealous eyes stabbing into my back.

"Wow!" I said as I held out my hands to her. "You look incredible, quite stunning!" She smiled and laughed, a rich and natural sound that made you want to hear it again. I took her arm and steered her towards my table. I had to walk behind her to squeeze through the gaps between the tables. Her dress was low cut showing her smooth dark skin and her shapely back almost down to the crack of her arse which remained tantalisingly out of sight. But the smooth material of the dress did nothing to hide the sexy round cheeks of her behind. There was no hint of a panty line anywhere and I found it exciting to think she probably wasn't wearing any, or that they were so small they were invisible.

I ordered drinks and we chatted. Conversation came easily and ranged over the usual stuff like how we came to be here, the hotel, the food, the weather and then quickly turned to more interesting things. We found out we were both interested in art and politics. All the time we talked I was aware that I was gazing into her deep brown eyes with more than polite attention. I could look at this beautiful woman all night. She seemed to be enjoying herself too. We ordered a few more drinks and then I suggested dinner. We decided to go to a small local restaurant I'd found - off the tourist trail and mainly used by locals where you could still get decent Spanish food.

During the meal we had a few more drinks and both became pleasantly drunk. She was smiling and laughing a lot and somehow, I don't know if it was her or me or if it was mutual, we moved closer together and the conversation began to get raunchier. I made a joke about the guy with the 9 inch dick and in no time we were discussing whether size mattered and what was important in a sexual partner. We discussed past partners and when we first had sex. We even got onto same sex relationships and she asked me if I'd ever had sex with a man. I was a bit uncomfortable because when I was at school I actually had had sex with another boy, just wanking and sucking and I found it embarrassing to admit it now, but she squeezed my hand and told me it was OK, and in fact she thought it was sexy. I asked her if she'd had sex with a woman and she giggled a bit and said yes a few times but she preferred men.

Things were going really well so I slipped my hand into hers and leaned towards her and kissed her. To my delight she responded and gently kissed me back. I stroked her shoulders and pulled her tight feeling her firm round breast push against my chest through the thin fabric. She pulled away and looked at me for a moment as if coming to a decision. "Let's get the bill. I want to walk on the beach." Oh my God! My dreams were going to come true! I quickly paid the bill and we walked down through the town towards the deserted end of the beach. We strolled along the sand towards a rocky cove. The Mediterranean sparkled in the moonlight. Small waves flopped onto the sand with little sighs of completion. I stopped and pulled her towards me, kissing her and feeling again her beautiful breasts caressing my chest. I slipped my hands down her back and over her behind. It felt smooth and warm under her thin dress and she pulled me closer as I squeezed her cheeks kissing me more deeply.

Suddenly she pulled back and turned away from me breathing in short gasps. My arms were round her waist and she held them with her hands. Her neat firm cheeks caressed my cock, but she felt stiff and tense.

"What's the matter?" I asked.

"Nothing. This is perfect. It's just too soon."

"Too soon for what?"

"Too soon for me to, to..." she lapsed into silence.

"Look I really like you. You're intelligent, fun and I think you're very, very sexy. But if you don't want to do anything that's fine with me."

"No it's not that. I want to but I just..."

"What is it?"

"It's complicated," she sighed.

"How so?" I asked.

"Oh, look. Let's sit here and talk for a bit. I need some space to think."

We sat on a rock still warm from the day's heat. I decided not to force the issue. After a few minutes silence she said. "You know in the restaurant when I asked about you having sex with other men?" So that was it. She was worried about AIDS.

"Well it was years ago so there's no chance of catching anything nasty."

"That's not what I meant. I mean, did you enjoy it? Be honest please."

"Well, um, I suppose I did, yes. Otherwise I wouldn't have done it again."


"Well yes, it was for most of one summer actually." I was glad the soft moon-glow covering my embarrassment. "Is that what's worrying you?"

"Kind of."

"Kind of? Just tell me what's bothering you. I'm not going to get mad or anything."

She put her head on my shoulder. We sat in silence for a few moments. I felt her relax and then tense again. Suddenly she stood up, walked a couple of steps away and turned to face me. "I want to show you my body," she said. Before I could answer she let her dress slip from her shoulders revealing her naked breasts, smooth and prominent in the moonlight. I gasped. They were perfect; small, firm and nicely full. Her nipples stood proud and erect. I wasn't at all sure what was happening here but her beauty took my breath away and I didn't care where this was going.

Then she let the dress fall to her feet and stepped out of it. Although she was silhouetted by the moonlight I could see she was wearing a very small pair of white thong panties that held a thin piece of fabric which dipped in a neat vee from her narrow waist down over her sexily prominent pubic mound and disappeared between her thighs. She was just faultless. I couldn't see what she was worried about. Standing before me she looked like a goddess who'd just emerged from the sea to grant my every wish.

Then she reached down and slipped her hands under the sides of her panties. She bent slowly as she slid them down her thighs and let them drop. As she straightened up I gasped with surprise. I wasn't sure what I was looking at. Her prominent pubic mound had changed shape and now seemed to stick out and down. In fact it looked like a small cock. I blinked in the half light. It was a cock. She must have been wearing a little strap-on or something. This was weird. Did she want to fuck me with it? I looked closer. It was amazing how real it looked. It moved like a real cock as she stepped towards me.

"What do you think?" she asked softly. I didn't know what to say. I looked again at the thing hanging between her legs; except it was no longer hanging it was standing up. Then it hit me. It was a real cock! She was a man. No, she was a woman. She had a perfect female body, smooth skin, pert breasts, a narrow waist, lovely rounded hips and buttocks... but she had a cock too. My mind turned somersaults. Somewhere in the confusion my body decided to ignore my mind and told my cock to stiffen into an erection. She was standing close in front of me. As if in a dream where you observe yourself doing something over which you have no control I watched my hand reach out and lift her cock towards my mouth. I felt the smooth firm warmth as it slipped between my lips. I sucked it deeper into my mouth. I tasted the tang of her pre-cum as I started to suck it in and out. One hand cupped her balls and the other slipped round to her bottom and pulled her towards me encouraging her to fuck my mouth with her cock. She was moaning and groaning and leaking more and more pre-cum into my throat. Her balls tightened and I could feel her little cock about to explode.

"I'm going to come," she panted between thrusts and then cried out as she shot her first load into my mouth. I continued to suck and massage her cock and balls while she emptied herself into me. I swallowed and licked and sucked her until she was empty and clean. Then I stood up and kissed her deeply holding her close so I could feel her breasts and cock against me and she could feel my excitement.

"I'm sorry I didn't tell you sooner," she whispered into my embrace. "It's difficult sometimes. I didn't know how you'd react."

"Well, I will admit it was a shock, but I seemed to get over it quickly enough!" We both laughed.

"So you don't mind then?"

"Mind? No of course not. It's the best of both worlds; a sexy woman with a nice cock to suck."

She leaned closer, kissed me again "And a nice tight bottom to fuck if you want too," she giggled.

Oh God did I want too! I couldn't get her back to my room fast enough. The thought of sliding my cock into her tight shemale anus and buggering her nearly made me come in my pants there and then.

In fact we ended up in her room as she had the supplies we'd need. She had a bottle of massage oil with which I covered her back and her sexy feminine arse cheeks. Then I lubricated her anus. As I opened her and slipped my cock past her tight entrance into her willing backside she groaned and started to come almost immediately, spilling her seed onto the sheets as she moaned and cried out. The excited thrusting of her hips and the squeezing massage of her cheeks tight around my cock was too much to take. After a few thrusts I started to come, spurting deep inside her and filling her back passage with my semen. It was all over in a few minutes but it was the most satisfying climax I'd ever had. I didn't know until then what I had been missing.

We lay and talked for a while. She told me how she'd always been a feminine boy and was quite happy like that. But her parents and her peer group were not comfortable with her - it seemed to confuse them. Eventually, in her early 20's she realised it would be easier to become a woman so she could dress in sexy clothing and exhibit her feminine self without all the problems she'd had until then. So over a few years she metamorphosed into this beautiful person who lay beside me on the bed stroking me and giggling as I kissed her and fondled her cock and anus.

Later she started to stroke my anus with her finger. I responded by opening my legs. Suddenly I felt her tongue replace her finger and lick around and inside my backside. Then she was kneeling over me and spreading oil over my cheeks, dripping some directly into my arsehole. I relaxed as I felt her little cock enter me. She very gently eased it in and out until I was open enough for her to push it all the way into me. Ever since school I'd wondered what it would be like to have my anus fucked and now I knew. It was fabulous feeling her firm warm cock entering my virgin backside and at the same time her breasts and erect nipples massaged my oiled back. I was in heaven.

My cock grew hard again. She fucked me slowly and carefully and eventually came in my arse. After she filled my arse with her sexy fluid she turned me over, straddled me and guided my cock into her hungry bottom. She rocked backwards and forwards until my full length was buried deep in her. Her buttocks caressed my cock and balls while I stroked her little cock back to hardness. Now she was fucking my cock with her tight bum and wanking herself between my slippery hands. Her tight ring enfolded me in its smooth grip and soon brought me to a wild climax as I deposited another load deep inside her. She felt me coming and climaxed herself, spraying her cum over my hands and chest. Then she lay on top of me rubbing it into my chest with her pert breasts while kissing me and telling me it was the best fucking she'd ever had.

I had to agree with her. It was the sexiest, wildest and most erotic fuck I'd ever had too. To fuck this sexy man-woman's arse-cunt and to be fucked by her was very definitely the best of all possible worlds.

We didn't make it down for breakfast the next morning. Somehow we were distracted in the shower and then again when I helped her choose her panties for the day. Later we walked further along the beach to a deserted, tree-shaded cove where we swam and fucked and sunbathed until it was time to go back to the hotel and eat a light dinner and fuck again.

By the end of the week I was in love with this strange and beautiful creature. She accepted my offer and now lives with me in my house near London as my girlfriend. My closest friends know she's shemale, but in other company we laugh a lot when she gets lusty looks from the men and jealous glares from the women. If only they knew!

Well if they would like to meet someone like her all they need to do is book a holiday!

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by Anonymous

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by Anonymous07/21/18


sexy, surprising and eky well-written. More please.

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by nightjack07/16/18

Great story

Loved the way you bought in the twust to the story. I was utterly enthralled.

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by Anonymous07/14/18

Hope to see more

I liked this. Nice balance between story and sex. I hope you write more.

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by Anonymous07/12/18

Well crafted story !

Thanks , great read ! Amazing that the story could be told so well on just one page .
I will be checking for more swbiguy's work in Literotica in the future .

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