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Going On Holiday

Going On Holiday

       I consider myself to be very lucky. Debby, my wife, is the most amazing woman I have ever met. She’s smart and funny, loving and kind. There are days when she makes me laugh so hard my sides feel like bursting. She is everything I ever wanted in a woman, and that’s not to mention the way she looks. Oh boy!

When we’re out and about men turn and stare at Debby. They notice her long lithe legs, her luscious breasts, and her silky black hair, which cascades down around her shoulders. Yep, I’m one lucky guy.

Compared to some of my previous girlfriends, Debby is also a bit of a nympho. We have sex at least once a day, more if we can get the kids out of the way. We have enjoyed toys and videos, and we have even had sex in places that others might find a bit kinky (that time in one of the cubicles in the ladies at the local pub was wild!).

But it was an ex-girlfriend, Holly, who gave me the most exciting sexual experience of my life. I don’t hide this from Debby. I’ve told her all about it more than once. We both get off on it, so much so that we’ve even talked about trying to recreate the experience. It all happened one summer, eight long years ago, when I was just twenty.

I met Holly during F.A.F. week in my second year at university. F.A.F. stands for Fuck a Fresher, and some buddies and I made a bet. A tenner each on who could F.A.F the most in the first month of term. I was confident I could win, but wound up utterly humiliated. My first F.A.F. was Holly and after meeting her, and having such a great time, I couldn’t bring myself to F.A.F anyone else. We were inseparable for the rest of the year and decided to go on holiday together that summer.

I’ve never been into beach holidays. I’m more of a museums and monuments person, but to please Holly, I booked an apartment on the Costa del Sol. It was right at the start of the season, which meant that the package was cheap enough for us poor students to afford. The cost also reflected that the town was one of the smaller, less well-known places on the coast.

The complex we stayed in had five apartments around a shared swimming pool and sunbathing area. Three of the other apartments were empty the week we were there. But in the apartment next to ours were five guys our age that messed about in the pool, played loud music, drank a lot and generally did the typical Brits abroad thing. They were all fresh out of Sixth Form, off on their first jolly without parents, and making the most of it. Holly and I hit it off with them straight away.

At nineteen, Holly was a hard bodied beauty, a real cracker, and the guys next door made no secret of the fact they thought so too. They would wolf whistle and holler every time she sat out by the pool.

I could tell Holly found these guys attractive and even though they were acting like morons, she loved the attention. She played up to it, selecting her skimpiest bikinis to wear during the day, and her lowest-cut, most revealing dresses during the warm evenings. She also turned it on in the sack. She fucked my brains into mush each and every night, not caring if the guys next door could hear us through the thin walls. Their attention had lit her pilot light, and I was having trouble putting it out.

One evening, around eleven, as we walked back from a beach bar, we met the lads on their way back to the complex too. They were bemoaning the lack of late night bars and discos in the area. Holly and I agreed that the town was rather sleepy. One of them, Baron, changed the direction of the conversation. "Hey man, you’re one lucky geezer, you know."

"Yeah," said another, his name was Duncan. "This girlfriend of yours is something else. I only wish you’d gone topless, Holly. Now that would have been a sight."

Holly blushed.

Duncan continued, "We were hoping there’d be some fit women here, especially Derek." He nudged his friend in the ribs. "But we never imagined there’d be babe like you here."

We reached our apartment.

"Would you guys like to come in?" I asked. "We can start our own party. I mean it’s not as if we’ve got any neighbours to complain or anything." They readily agreed. Two of them retrieved some booze from their place, and I fished out some music and put it on the stereo.

We planned to party well into the early hours. The booze flowed almost non-stop, with one of the guys popping out to an all-night shop to get more when we ran out. But by two, we were all starting to flag, and I changed the music from the hardcore dance tunes we had been playing to more seductive, slow and smoochy tunes.

I danced with Holly while the others watched, and the booze must have really affected her because as our tune came to an end and the next one started, she pushed me away and grabbed the nearest of our new friends.

The lucky guy was Baron. They danced very slowly, and when the next tune came on Holly again switched partners. She carried on switching partners until she was dancing with Josh, the last of the group.

As I sucked on yet another beer, I noticed that Josh was pulling the zip of her dress down, revealing the soft, tight, tanned back. Holly kissed Josh, and he slowly slipped the dress off her shoulders and let it drop to the floor. Under the dress Holly had on her sexist undies – sheer black bra and thong-back panties that left little to the imagination.

"Like I said, you’re one lucky geezer," Baron said.

"Too fucking right," said Duncan. He and Baron clinked the necks of their beer bottles together.

"And don’t you boys fucking well know it," I replied. I clinked the neck of the beer bottles of all the guys sitting down with me.

Our boozy good cheer was interrupted by a loud, low moan from Holly. She had her head tipped back. Josh was massaging her tit with one hand and had his other hand inside her knickers. The rest of us watched, transfixed, as Josh’s fingers worked magic on Holly.

In just a few short minutes, she was grinding her hips against his hand, and moaning louder and more frequently as her orgasm approached. When it hit, it surprised the rest of us with its ferocity. She wrapped her arms around Josh’s neck as her legs gave way, and she screamed her pleasure at the top of her voice.

I didn’t feel the slightest twinge of jealousy as I watched this virtual stranger bring my girlfriend to an earth-shattering climax. If anything, I felt pride that they all found my Holly so sexy, and excitement at where this all might lead. I was young, dumb and far too full of cum to give a toss about things like fidelity, or even disease. All I cared about right then was empting my balls and becoming just a little less full of cum. When she came down from her high, Holly unpeeled herself from Josh and stepped back.

"Oh," she said. "That was nice." A wide grin spread across her face and she added, "Well, since I’m already wet, I may as well go for a swim."

She bounded across the room to the French doors, flung them open and stepped out onto the patio. The five of us watched, cocks bulging in our jeans, as she skipped to the pools edge and peeled her soaking wet panties off. She threw them over to the doors, then reached up behind her back and unhooked her bra. She threw this over to us as well and then dived into the pool before any of us had gotten a good look at her charms.

I already knew them well of course, but the five lads were desperate to have a good gawp, and rushed out to the poolside as fast as their erections would allow. I strolled along behind, curious about what the next development might be. Holly swam a couple of lengths, front crawl, and we all watched her arse intently as the water lapped over it. It was heavenly.

Then she really pleased the guys by turning over and doing two laps of the pool on her back. The guys all cheered as her glorious tits poked up out of the water, her nipples looking painfully erect from the cool night air.

When she came back around to where we were, she stood in the pool, crouching so that her tits were just below the water line. "Well aren’t any of you going to join me?"

Within seconds, all our clothes were off and we dived into the pool. Baron and Josh were the first to swim up to Holly, each of them grabbing a handful of tit. Duncan came up behind her and reached down to feel her arse. The other two, Derek and Philip, were with me, not too far away, watching.

"Fucking A," Philip said.

"Fucking A star," added Derek.

Holly kissed Josh, then Baron, then Josh again. Her breathing was shallow and she was moaning again. Duncan had moved his hands from her arse to her cunt.

"I want to get fucked," she said suddenly, surprising us. I suppose we should have expected it.

"She is one hot bitch," Philip said. "I can hear the pair of you from my room, so I known you’ve been at it like fucking rabbits."

"I can’t believe she wants to fuck all of us," said Derek. His eyes lit up with anticipation.

We wasted no-more time, helping her out of the pool and laying her down on one of the sun-beds nearby. Josh knelt down between her legs and began lapping at her cunt. Baron and Duncan each offered her their inflated pricks. She took one in each hand and alternated her mouth between them.

Not to be left out, Philip knelt down and sucked on one tit, and Derek turned his attention to the other. I stood back and watched, proud that this sexy, wanton woman was mine to take home when we’d all finished for the night. Holly writhed about on the sun-bed, trying to keep her mouth full of Baron and Duncan’s cocks, but not doing very well. I was busting, and I could tell that Holly was getting close again. I tapped Josh on the shoulder and when he looked up at me I said, "She’s mine, so I get to go first, yeah."

"No problem man," he said, "as long as we all get a piece."

"Oh, you’ll all get some," Holly said. "But unless I get a cock inside me now, none of you will get a fucking thing."

Josh stepped aside, and I took his place between her legs. Rather than putting my tongue against her pussy, I rubbed the head of my dick up and down her slit.

"Stop pissing about and just fuck me," she screamed.

So I did. I slid inside her velvety depths, and she instantly stopped rubbing Duncan and Baron’s cocks. My boiler was well and truly stoked, and I rammed into her with lighting speed. She came before I did, but not by much. In fact, I’m sure her orgasm triggered my own. When I had finished depositing my load inside her, I pulled out, stepped back, and watched as Josh took my place. I knew that I had taken Holly’s virginity just nine months earlier, and this would only be the second cock she’d ever had inside her. Her eyes were wide as Josh aimed his prick at her cunt. Her mouth formed a small ‘o’ shape. She gasped silently as he slid in as far as he could.

After bottoming out, Josh withdrew slowly, clearly savouring the sensations of Holly’s tight little hole. Twice more he slid in and out slowly, and then he set about pounding her relentlessly. He didn’t last long, but it was still long enough for Holly to cum yet again. The third time that night!

When Josh was finished, Holly experienced the third, fourth and fifth cocks of her life as Duncan, Baron and Philip serviced my sweet, sexy girlfriend.

When Philip was finished, he moved aside, leaving Holly looking sexier than ever. She lay on the sun-bed, glowing with lust. The remnants of five loads of spunk dribbled from her pussy and down the crack of her arse.

"I count six men but only five lovely hard dicks," she said, dreamily. "Who am I still waiting for?"

All eyes turned to Derek, who stood stock still, petrified.

"Come on man, fill yer boots," I said. "It’s not every day you find a girl who’s literally begging to be fucked."

Duncan started to laugh and said, "Derek’s our resident virgin. The whole point of this holiday was for us to help him pop his cherry."

"Well you’ll never have a better opportunity," I said. "Or have many sexier women."

"Hey," Holly said haughtily, "He’ll never have a sexier woman, period."

"You’re not wrong," Duncan replied with a chuckle.

"Come on Derek," Holly said in a voice laced with sexual desire. "I’ll give you a first time you’ll never forget. But let’s go inside first."

Holly jumped up from the sun-bed, and despite being a little unsteady on her feet, she took Derek by the hand and led him into the apartment. They went through the lounge and into the bedroom. Derek’s face was expressionless, but his cock was standing out straight, proud and ready for action.

The rest of us had followed and were gathered around the bed to watch Holly take Derek’s virginity. Holly pushed him down onto the bed and then crawled between his legs.

"So how much of a virgin are you Derek?" she asked. "Have you ever had a blow-job?"

"Y... yes," he managed. "J... just once."

"Did you enjoy it?" Holly asked. "Don’t answer that, I’ve never met a man who didn’t enjoy a blow-job."

The five of us around the bed laughed and agreed that there were few things in life as fine as quality fellatio. Holly put her manicured hands around Derek’s stiff prick, and he jumped. I swear he nearly came right then, and I was impressed that he managed to hold back even when Holly licked around the head of his dick.

She teased a little more and then swallowed as much of his cock as she could. She bobbed her head up and down over his swollen member, trying to suck his spunk out of the end. It wasn’t long before she got her reward. Derek bucked his hips, grabbed Holly’s head and tried to fuck her face.

She seemed more than willing to let him, and she moved one hand from Derek’s cock to between her own legs. Josh stepped forward and looked as if he might fill Holly’s cunt again, but Duncan held him back, telling him that this was all about their friend. Josh complained but nevertheless, complied.

Meantime, Derek was empting the contents of his young balls into Holly’s mouth, and she was swallowing it as if it were cold, fresh beer. When he was finished, Derek let go of Holly’s head, and she sat up.

"Hey," said Baron, "I thought you were going to fuck him."

"Oh, I am," said Holly. "I just didn’t want his first time to be over in seconds. This way he’ll last longer. At least, that’s the plan."

Derek’s cock was still like a rock, and Holly shifted her body so that she was sitting on his stomach.


Derek nodded his response. Holly lifted her hips, reached behind her back and aimed Derek’s dick at the entrance to her body. Slowly, very slowly, she sat down, lowering herself onto him.

From my position at the foot of the bed, I had a perfect view of Derek’s prick as it pushed past Holly’s pussy lips. I could see her pubic hair tickling his dick as it slid into her, and his pubes mixing with hers when he was all the way in. That sight has fuelled my wanking fantasies ever since.

Holly sat on him, letting him enjoy the feeling of being completely inside a woman for the first time. She slowly pulled herself up and then forced her body back down, causing both of them to gasp. She did this twice more, and then built up some speed, bouncing up and down, faster and faster.

Derek grabbed her arse and started to thrust up to meet Holly as she came down. They kept up this incredible pace for ages, finally coming together. Holly screamed louder than at any other point in the night. She collapsed on top of Derek, both of them breathing very heavily.

Those of us that had been watching the show were all desperate for our own release, but it was clear that Holly was done for the night. Instead of sucking or fucking any more of us, she rolled off Derek and lay on her back as the five of us wanked our cocks over her until we shot five loads of thick, creamy sperm all over her body.

One by one, the boys wandered back to their own beds in the next-door apartment, and I was able to crawl into bed with my girlfriend. None of us left the complex the next day, sunbathing nude the whole time, and Holly got fucked by each of us over and over again for the rest of the week-long holiday. It was, without a doubt, the most sex she had ever had, and the best holiday I had ever had.

Whether it had anything to do with the events of that week or not, I don’t know, but Holly and I stopped seeing each other not long after getting back from Spain. The last I heard she was also married with two kids, just like me. Her husband was a high-powered lawyer and prospective Conservative parliamentary candidate, so I can’t imagine that she’d told him about that holiday. I, on the other hand, shared everything with Debby. We’ve booked two weeks at the exact same complex for next summer while Debby’s parents take the kids to Disneyland Paris. We’re looking forward to it.

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