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Heather’s Working Holiday

Category: Group Sex
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My mother always said that I was an entrepreneur and after my holiday in Spain she was proven right.

I went out with my girl friend Heather on one of those budget self catering holidays that you can buy cheaply on the Internet. Neither of us had a lot of spending money but there should have been enough to last us the three weeks we were staying in Spain.

I say “should have”, because Heather managed to loose the wallet with all our money in it on only our third day in the apartment complex we were staying in. I had told her we shouldn’t take it all out with us, but Heather thinks she knows best and she ignored me and then the silly bitch went and lost it all.

I was furious with her as you can imagine. She was really upset, mainly because we had rowed over her bringing the wallet out in the first place and she knew she was totally to blame for its loss. Her green eyes were watering dangerously as we back tracked our steps in the hope we found the bulging wallet lying on the sidewalk. We didn’t of course.

“You fucking silly cow,” I said angrily to her when we finally gave up and headed back to our small two roomed apartment in the complex we were staying in, “What are we supposed to do now for the next three weeks?”

“I don’t know!” she wailed and she flung herself onto the sofa and cried which wasn’t very helpful and only made me madder.

“This is all your fault,” I said peevishly and she howled louder, mainly because she knew it was true.

“I didn’t mean it,” she bawled, “It was an accident!”

I glowered at her, for one as gorgeous looking as Heather; she was really very stupid sometimes. And I mean really stupid. Her only assets were her tits and ass, because her brains weren’t of much use. She had the body and physical assets of a model but the brains of a vegetable garden.

This thought made me smile inwardly and it was at that moment that I got the idea of how to save our holiday from sinking faster than the Titanic.

I stared at my crying girlfriend, seeing her evenly tanned flesh, her long slender legs, her thick wavy golden hair, generous mouth and beguiling green eyes. Her rounded ass was firm and pert, her tits were all her own, nature had given her a pair of real beauties. She was also shit hot in the sack, what she lacked in brain power she made up in fucking power. My cock growled in my pants just thinking about how good she looked when her pretty little ankles were around her ears.

“You made this mess,” I heard myself say loudly, “So you’re going to have to sort it out.”

“How can I sort it out?” Heather wailed looking up at me with tear stained eyes, “I don’t have any money Jake, you know I don’t, I maxed my credit card out paying for the tickets.”

“You’re going to have to earn it,” I said calmly and I sat down beside her on the sofa.

Her tears stopped. She looked at me with a puzzled expression on her face.

“It’s your fault,” I said calmly, “So you’re going to earn have the money for our holiday.”

“How?” she asked.

I told her my idea. She looked at me in horror.

“I can’t do that!” she wailed and she began to cry again.

“Oh yes you can,” I said flatly, “Unless you want us bloody starve, because I don’t even have the money to phone to ask my brother to bail us out, anyway it will teach you a really good lesson, to be more careful next time, won’t it?”

She snivelled, hiccupped, tried to protest a little bit more but she soon realised there was nothing else to be done. And it was her fault we were in this predicament.

“How will I do it?” she asked me finally and I knew she had accepted the idea.

My groin stirred, but I kept myself calm as I spoke.

“We’ll go to the bars and clubs,” I said, “I’m sure we’ll get you plenty of customers, there’s a lot of guys who would be willing to pay to fuck you, of that I am pretty sure!”

Heather licked her moist red lips.

“Are you sure?”

It suddenly occurred to me that Heather was secretly turned on by what I was suggesting. I could see it in her eyes, she was trying to disguise it but I’ve been fucking this girl for two years now, and I know her inside out, upside down.

I smiled, “Oh yes,” I said, “We can make plenty of money for our holiday selling your hot little ass, but you won’t be able to fake it, you’ll be paid for the real thing.”

She nodded her head. I stood up.

”Well you better get ready then,” I said briskly, “Wear something short and sluttish, that white dress will do, and wear a thong, oh and shave your pussy, men like that.”

I have to admit Heather did me proud. The short white dress I had suggested really did the trick, she looked so slutty, I wanted to rip it off her and fuck her silly.

It’s one of those cheap sheer numbers; it goes just below the thigh and flares out like silk. It’s sleeveless and the top part that covered Heather’s tits is so transparent you can see her pert cherry coloured nipples under it without even trying.

She wore her cream favourite four inch high stilettos and her tightest most revealing thong.

“How much do you think we will make tonight?” she asked me anxiously as we left the complex together and made our way toward the busy centre where the bars and clubs were beginning to fill up.

“Depends,” I said cautiously.

“Where will I do it?” she asked me.

”Wherever the guy wants,” I said slipping my arm through hers, “Probably in the toilets or in some alleyway out back, I’ll get the money off the guy and you go and fuck them, I’ll drum up business for you.”

“What will you charge?” I could Heather’s voice change slightly, she was getting turned on, so was I but I had a job to do. I was about to sell my girlfriend’s ass to pay for our holiday.

“Leave that to me,” I said and she nodded her head meekly. I smiled inwardly. This was going to be fun.

We found a promising looking bar ten minutes from our apartment. It wasn’t too crowded but there were a lot of potential punters for Heather’s ass. It was surprisingly easy to drum up our first lot of business, easier than I had thought, I been a bit worried at first though I hadn’t let Heather know this.

Heather’s first customer was an American boy who sidled up to us and asked Heather to dance. He was quick to realise that Heather was for sale and he gave me £20 without a word and they disappeared into the men’s toilet for 20 minutes.

Although I didn’t get to watch I could just imagine what was going on and my cock groaned in my pants.

The American boy had a grin on his face when he finally came out, he was fastening his pants and he gave me the thumbs up sign before disappearing to get himself a much needed drink at the bar. I nodded my head at him and a couple of minutes later Heather was back by my side. She was red faced, her top was crumpled. There was a trickle of cum sliding down her leg.

She sat down and I looked at her expectantly.

“Well?” I said, “Did you enjoy it?”

She blushed. I grinned.

“I hope you did,” I whispered in her ear, “Because it’s turning me on, I know we need the money but God Heather, it make me horny thinking of you being fucked by other guys, it really does!”

She swallowed hard and licked her lips.

“He was pretty good,” she admitted, “God, Jake I wish you could watch, that would be fantastic if you could watch!”

I had thought of that too but I didn’t see how I could, it was really frustrating, for both of us.

It was the one of the waiters who helped us out in that area. He came over with the drinks I had ordered and asked if he could have a word with me on my own. I left Heather sipping her drink and he took me to one side.

“I saw the American boy pay you for your girlfriend,” he said and I stiffened at his words, he smiled and shook his head, “No problem Senore, but perhaps you’d like somewhere where she can go to, er work?”

I eyed the waiter suspiciously but he explained. His name was Paulo, and he ran this bar for his Uncle. Upstairs he had two rooms, one had a double bed in whilst the other was connected to it via two way mirror.

“We make amateur videos,” he said coughing slightly, “You obviously want to make some money, well why don’t we help each other? Your girlfriend can take her clients upstairs and you can watch.”

“What do you get out of it?” I asked.

Paulo smiled broadly, “Well I get to watch too, but I’ll film her at work, my payment will be selling copies of the video, whilst you both get to take home what she makes.”

It was too good a deal to turn down. We shook hands on it.

“My uncle has four other bars all over the city,” Paulo told me, “With a similar set up, she’ll have lots of work, a lot!”

I grinned.

“I should hope so,” I said reverently, “Oh I hope so…”

Heather was a bit doubtful about the deal I had struck up with Paulo, I didn’t mention the videoing but I told her I’d get to watch and she’d have the privacy of a nice bedroom above the club to get down to business. Better than being shagged up against a wall, didn’t she think?

She did.

Paulo proved useful in getting Heather clients, and very soon Heather was going upstairs with her next customer, an English boy who paid me £20 and as they shut the bedroom door I slipped into the next room and sat down opposite the mirror to watch.

Paulo had already set up the recording equipment, he was too busy to watch at the moment but he would come up later he said.

The room was a large square shaped room with a sturdy high mattress bed pushed against the wall opposite the large two way mirror, plain light walls so that everything could be seen from the room next door, a polished soap stone floor and one chair with plenty of towels piled on it in a far corner.

I also noticed there was also a tiny wet shower room leading off the bedroom but it didn’t have a door. I got the feeling that the solid bars bolted onto the shower walls weren’t used solely for towels. The room was large and airy and was custom made for fucking and filming.

The English boy was horny, and Heather certainly earnt her £20. There were no social niceties, Heather was a fuck commodity and he made this abundantly clear to her.

She had barely got through the door before he was behind her, his hands grasping both her tits and squeezing them. Heather gasped and then moaned, as his hands slid down her midriff and slid under the hem of her slut white dress and then down into her crotch.

“You’ve got a juicy cunt,” the boy said, his fingers moving in and out making Heather squirm, “Let’s see you’re worth the money I’ve just paid for you!”

“I am worth it!” Heather moaned thrusting back and forth on his roughly probing hand hands.

“You better fucking be bitch or I’ll want a refund!” he said in a hard voice, “Now get on your knees and let me see that mouth of yours do some work!”

Heather obeyed, gliding to her knees, and quickly opening the boy’s pants. He had a hard on, and Heather quickly made it bigger, her luscious mouth slurping and licking his rippling shaft.

They boy grabbed two handfuls of her hair and began to thrust hard into her mouth with his swollen cock. My hand immediately went to my crotch and I found myself rubbing my rapidly swelling dick, I could see Heather’s face, her eyes were bulging as the boy brutally used her mouth. She gagged at first, reflex did that but soon she was moving with him, her hands clutching at his hips for better leverage.

”Suck harder you filthy slut!” the boy shouted, “Come on, do it properly!”

Heather desperately sucked harder, her baby pink cheeks were bulging with the girth of his cock, and amazingly he was big and getting bigger!

I was rubbing my pants harder my eyes glued to the mirror in front of me; I was panting heavily, totally turned on by what I was watching. I had to fumble with my zip to let my painfully cramping cock free from the confines of my trousers.

“OH YES!” the boy shouted over and over again as Heather sucked him toward an orgasm, “OH YES!”

He didn’t come right then, he slid out of Heather’s mouth with a sudden pop, his pre-cum dribbling down her chin and said with eager relish.

“I’m going to fuck you up the ass!” and before she could utter a protest he pushed her onto the bed on her belly, forcing her to get on all fours. She was panting and mewling, unsure what to do next but I could see she was horny as he was.

He yanked up her the hem of her dress and dragged down her thong to reveal a round, firm strong pert bottom. He parted her bum cheeks, lowered his face to her musky bum hole and began to gobble at her squirming ass crack.

She bucked and screeched in pleasure, as his tongue pushed inside her; he lubed her ass with eager strong strokes of his tongue. He then sucked on three of his fingers and then rammed them up her bum hole really hard.

Heather let out a bellow and practically flew off the other side of the bed. He held onto her, by grabbing the back of her neck pulling her back and wiggling his fingers inside her, making her rump buck and thrust against them in shocked pleasure.

He was getting her off and I was practically hammering my dick into oblivion watching him do it!

All this for £20! What a fucking good deal was all I could think!

“OH YES!” my slut girlfriend shouted over and over again, her body heaving and thrashing about as her pert little bottom was brutally aroused, “OH YES! YES! YES! YES!”

The boy ate her ass some more and then he was ready. Even as lubed as she was, Heather bum hole really had to stretch to accommodate him and she hollered, bucked, bounced, and cried out in willing protest as he pushed his meat up her ass.


The last word was a wail of pure orgasmic pleasure as the boy’s cock finally slid all the way up her ass to its shaft.

He began to pump, not gently, thrusting real hard making her move up the bed whilst she bucked and rasped out her pleasure.

I could even hear his balls slapping against her rump, he was thundering into her and she was crowing so loud I was sure that they could probably hear her downstairs in the bar!

My hand was working over time on my cock as I watched, I intended to come at the same time as Heather, I would make it last, I bloody well would!

The boy leaned into her, straining and heaving inside of her, his hands grasped her tits and he began to fondle them, squeezing the nipples until her juices flowed. Heather cried out with the sensation and she eagerly licked his fingers when he pushed them into her straining, groaning mouth.

“I’m going to fill you slut ass up with my spunk!” the boy was gasping now, getting ready to come, “I’m going to make you think you’ve got the Hoover Dam coming out of your asshole when I’ve finished with you, you dirty little slut!”

He was as good as his word, and he exploded inside Heather just as she herself started to come, he grabbed her soaking wet crotch and began to vigorously rub it, forcing his fingers over her already over sensitive clit. She screamed. A scream of raw primeval pleasure, it made him come again as he was still up her ass, shooting a second load inside her and at that moment my cock spurted, luckily I had grabbed a towel and was jacking myself off with it so I didn’t make too much of a mess.

Cum gushed out of her stretched ass hole, and Heather fell forward with a gut churning cry and the boy let out a whoop now that he was fully sated.

He kissed each of Heathers’ bum cheeks which were still up in the air, trembling as her orgasm slowly died down.

“You’re one hell of a fuck,” he said and then he left after mopping himself up with a towel from the chair in the corner of the room.

Heather couldn’t move for a few minutes.

I slipped into the room and shakily she managed to get back to her feet. She had to sit down on the bed, I handed her one of the towels from the chair as the boy’s spunk was sliding out of her and down her legs. She was also out of breath.

“He was only about 19,” she gasped, “He fucked like a stallion!”

“You took it like a stallion,” I said and she giggled.

“Did you like it?” I purred at her and she physically trembled at my words.

“Yes,” she whispered, “Oh yes Jake, it was unbelievable!”

“And we got paid for it,” I said patting my back pocket.

She groaned at the wickedness of my words. We both knew it was wrong, but it felt so good…

”I’m such a slut,” she said with a giggle.

”You certainly are,” I agreed but before she could say anything else the bedroom door opened and Paulo stuck his head around the opening.

“You’ve got more customers,” he said smiling at us both.

Heather’s eyes widened and she licked her moist lips.

“How many?” she asked, she was holding her breath I could see, and her tits were straining against her crumpled top. My dirty slut girlfriend was ready to go again, not just one more time but a LOT more times I suspected.

“Ten and still counting” he said grinning and her eyes almost popped out of her head.

“I’m not sure I’m up to it…” she began trying to be all demure and coy.

“Oh yes you are,” I interrupted her, “Remember it’s your fault we’re without any money, you’re going to earn it back with interest, now move your ass and get cleaned up, you’re going to learn a hard lesson Heather, but you’re going to learn it well!”

She flushed, her face going scarlet at my words but she knew I was right.

“There’s one group of four who want to gang bang her,” Paulo said to me as Heather hurried to have a quick shower before her next job.

“Sure,” I said, “But it will cost extra.”

Paulo nodded his head.

“I’ll send them up,” he said, “They should get her juices going.”

“Oh they will,” I assured Jake, “They certainly will!”

Heather earnt £100 for the gang bang and Paulo wasn’t kidding when he said that they would get her juices going! She was awesome; I came two times myself watching her.

The four guys were from Australia and they sure knew how to fuck a girl.

First she had to suck them off, one at a time, they made her sweat I can tell you and their cocks, oh boy, Heather’s lips were going to be real sore that was sure!

I sat in my room watching my girlfriend take it from all directions. She was total dynamite; her orgasms were as loud and messy as her clients! Her tits bounced back and forth like two vigorously played with basketballs in a practice session.

One of the Australians suggested that they take turns and fuck Heather in the wet bathroom so I got to see those iron bars in action, not to mention two of the Australians who took a fancy to fucking Heather whilst she lay splayed out on the bed, one giving it to her between her legs, the other sitting on her face his cock thrusting in and out her spasming mouth whilst she clutched at his bare buttocks with two eager hands that was practically pulling him down her throat.

I was almost sure I could see his spunk filled balls disappear into her mouth every second stroke! The other two Australians watched, cheering and laughing and saying what a “hot fucking cunt they had paid for and it was worth every single penny!”

All in all it was a spectacular night, and by the time Heather’s last customer had left with empty balls and a smile on his face, my girlfriend had fucked at least 18 guys in a variety of filthy delicious ways and made £360 plus the Australians had left a £50 tip which I quietly pocketed without telling her.

She was a real spunk queen even after having several showers. It was oozing out of the corner of her mouth, trickling out of her ass and cunt and she was as sore as hell she admitted to me with a satisfied look on her face. Her cunt was on fire, her ass was throbbing and her tits had been sucked so often she had started to lactate!

“You were real hot!” I said to her, “I knew you were a slut but you’ve taken slutdom to heights I didn’t even know existed!”

“I think I’ve learnt my lesson?” she said hopefully as she got to her feet. She winced as she put her dress back on; her tits were so tender even the cheap material of the dress hurt them.

I didn’t answer her, we had just less than three weeks here, Heather’s ass could make a mint and I intended that she work her tits, cunt and ass off every single day until it was time to fly home. She’d do it. She’d balk at first but she’d do it.

Also I didn’t intend to give Heather half of the money; she had no idea what I was charging and she’d believe me when I told her that I was charging £10 a fuck. I intended to put the price up to £30, Paulo said I’d get it, and then I’d give Heather £5 for each guy she fucked, she’d think we were splitting the money down the middle but in fact I’d be taking over 80% of her earnings.

Not only that but I’d make her pay half the costs for food and such like so I’d make a profit on that too. She’d never know and this turned me on as watching her get fucked for money!

Paulo drove us back to the apartment complex; it was three thirty in the morning and quite a few pubs and clubs were still open for business but Paulo left his cousin in charge so he could drive us back.

I invited Paulo up for a coffee and he agreed. His eyes were on Heather and I knew he had the hots for her. She noticed it too; she squirmed and tried to notice it.

Paulo was real good looking, in fact he was the spitting image of the Latino crooner Ricky Martin, only more slender around the waist and his hair was dark brown instead of black and he had blue eyes, a gift from his half German mother he hold me.

“He wants to fuck you!” I whispered in Heather’s ear as he walked behind us, heading for our sixth floor apartment.

“Oh God!” she breathed back, her tits mottling under her flimsy dress and she whimpered, “I’m too sore, I’ve had 18 guys up my snatch today, it’s on fire!”

”Let’s round it off,” I whispered back, “Make it 20, I want to come in your juicy bum hole that’s all nice and spunked up and I know Paulo would love to shoot a load of cum into your cunt, and I know you want it too, I can see your titties have gone hard already, you want it too!”

“I don’t know if I can take it! I’m so sore!” she whimpered almost desperately.

Paulo was suddenly at her side, he knew what we were talking about, we had stepped out of the lift that I don’t even remember us getting into and we were walking along the silent corridor to our door.

Paulo stroked her arm, running his fingers up and down Heather’s goose pimpled flesh. She moaned.

I unlocked the door and as soon as we were inside, Paulo was pulling Heather’s dress over her head and tossing it to one side, leaving her standing in her cum stained knickers. She mewled out a protest but when he kissed her hot salty mouth, she melted and together we led Heather into the bedroom, kissing and caressing her trembling, moaning body.

We both latched onto a swollen tit each, she cried out in pleasure and pain, our mouths filled with her hot lactating juices, and her chest bucked into our mouths.

“OH! OH! OH! OH!” she cried out and she grabbed at the back of both our heads and ran her fingers through our hair.

Paulo’s gobbled at her tit eagerly as did I.

“I want to eat her pussy,” he said hoarsely, “Help me eat this slut’s pussy Jake!”

I was more than willing to oblige. I pushed my moaning girlfriend onto the bed and made her spread her legs as wide as possible. Paulo yanked down her thong and tossed it to one side.

“She’s real stretched down there,” I said with a chuckle as I looked at Heather’s shaven crotch which was glistening with her juices and those of the men who had come inside her earlier, this turned Paulo on completely and he practically dived into her.

Heather bucked against his face, crying out she did with hot even little mewls like a virgin filly about to be shafted by the alpha stallion “Her cunt has worked real hard today, so has her mouth, I think it needs to work a little harder, open wide Heather my hot little slut, help get my cock nice and lubed to push up your spunk filled ass!”

I straddled her face like the Australian had and she obeyed me, her mouth and lips rippling over my the ridges on my circumcised cock, I slid down her elastic throat like an ice lolly melting in the sun and her lips nibbled at my balls, making me groan with pleasure at the delicious sensation.

I gripped her two handfuls of her damp golden hair and made sure she took me in her mouth as far as was possible.

Heather’s eyes were practically out on stalks, they bulged under the pressure and she began to drool, she clawed at my buttocks and I moved backwards and almost out of her mouth, letting air explode out of her lungs in a rush, she thrashed against Paulo’s face and he moaned in pleasure as she smeared his face with her hot fiery juices.

She greedily slurped and sucked my cock into a swelling throbbing mass of eager flesh, ready for her quivering, already overstretched and well filled bum hole.

Finally both Paulo, and I were ready to round up Heather’s total to 20 and she was more than ready too.

“Fuck me until I pass out!” she begged us both taking us by surprise, “Fuck me until I’m unconscious, oh yes, you have to do it! do it! do it!”

Both Paulo and I were more than willing to comply.

Somehow Paulo and I managed to slide our respective cocks up Heather’s cunt and ass hole almost simultaneously, and at this moment her mouth rippled over her teeth in shock at the sheer sensation of it and she came with a flood of streaming juices at that very moment, neither of us were expecting that and we almost shot our loads prematurely but we hung on, thrusting into her, with vigorous short strokes.

“OHHHHHHHHHHHHHHHHHHHHHHHHHH!” she screamed and she bucked and bucked against us both in violent, thrashing orgasmic spasms before passing out from the sheer mind blowing experience.

That didn’t stop Paulo and me fucking her still trembling, spasming but now very unconscious body. It responded to us, but Heather was totally gone, her eyes were closed, her mouth slack and dribbling but she came two more times even when unconscious. I marvelled at her stamina, her body was a veritable shrine to the art of fucking.

I had been banging her for the last couple of years but even I was impressed by what she was capable off. She was fucking (forgive the pun here please!) awesome!

Paulo was finishing off her tits as he shot the last of his spunk inside of her.

We both slid out of her unconscious body, letting our juices flood out of her.

He flopped onto the floor and fell asleep instantly, I went to have a shower, I was tired but I had one last thing to do before I went to bed.

After my shower I straddled Heather’s now sleeping but steadily breathing body, positioning myself in direct line with her face and I began to jack off my cock. I took my time, but it wasn’t long before I was ready to cum, first I squeezed Heather’s mouth open with one hand gently pushed the hard head of my cock to her lips.

Instinctively even though she was now asleep her lips pursed and she began to suck the end, waves of pleasure shot up my cock and I moaned. Cum slid into her mouth and I made sure she swallowed several mouthfuls. I still hadn’t come completely. I jacked off over her tits and smeared it all over them; I wanted her to smell of raw sex juices when she woke in the morning.

I didn’t intend to let her to shower until Paulo and I had “given” her, her breakfast, two lots of hot juicy come which she was going to lap up and smack her lips over, of that I was more than sure.

Finally I was finished and I settled down to get some sleep.

As my eyes closed and I drifted off into a contented slumber I was working out in my head how much money my slut girlfriend Heather was going to earn on her “working” holiday.

Also I intended that Paulo give me a cut of the money he made from the videos of Heather banging her customers. Heather didn’t know it yet but she about to become Spain’s hottest underground porn star!

And all of this from just loosing a wallet!

And by the time we got on the plane to go home in three weeks time Heather would have the most stretched bum hole in Spain, a burning spunk filled juicy cunt, tits so swollen they’d be like plums and a mouth so hot and sore she’s be speaking nasally.

She’d probably be pregnant too, but I didn’t mind that, after all it was only right that Heather got to take a Spanish souvenir home with her. I mean it’s her holiday too and she should get something out of it too….

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