Pleasure Island Ch. 01

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Pegging

Author’s notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author’s knowledge, bears no relationship to any factual occurrence.

3. All characters in this story are over the age of 18.

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Tina gently lay forward, stretching her legs beside mine, as our breathing gradually slowed. My hands slowly caressed her back, her hair, her ass cheeks as I felt myself softening inside her still pulsating love tunnel.

“Oh, I love you, darling,” she murmured against my shoulder, “You’re such a wonderful lover, honey.”

“Mmmm, same goes for you, sweetheart.”

We lay silently for a few minutes, then she seemed to remember something we had to do. She leant back and looked at me.

“We have to organize our holiday work, today. No time for lying in bed, nice though it is, or we’ll find ourselves on the street with no money and only love to feed us. And as enjoyable as that would be, you’d soon be complaining of hunger. So, we need to go look for something that’ll keep wolf from door.”

I realized she was right; end of term had come, exams were complete, we now had six weeks before we had to think about our post-grad courses, and our current lease ended in a couple of days. So, we had to do something urgently. But I had an idea that I hadn’t shared with Tina yet. I reached for an advertising flyer on the side table.

“Have a look at this and tell me what you think,” I said, handing it to her as she rolled off onto her back, my cock feeling strangely lonely almost immediately it popped out of its warm sheath.

Tina skim read the article and then grinned at me.

“What do you think?” she asked.

“Well, I wouldn’t have shown it to you if I didn’t like the idea. Could be a great summer. What’re your thoughts?” I asked, knowing that she was always more timid than me, more reluctant to dive in the deep end and hope everything worked out.

“Well, it looks good, but I just wonder what the catch is. You know the old saying, if something looks too good to be true, it usually is.”

“Yes, maybe, but just maybe, for us, there will be no catch. Reading between the lines I would guess that the ‘personal services’ that we’d be supplying to club patrons would be interesting to say the least, and could even be very enjoyable. Obviously, they don’t want to advertise too blatantly, so the very least we can do is to give them a call, don’t you think?”

“Well, that can’t do any harm and we are getting to the stage where we really need something to bring in some money quite urgently. The live-in aspect of having accommodation and meals free of charge sounds great, in fact, too great, which makes me suspicious. Let’s call them anyway and then reassess.”

We sat in our small lounge after the call, wearing bath robes, and feeling excited by what we’d heard.

“Great that their reps are in town today and that they had a spare slot for an interview,” said Tina, “Sounds like we’ve got an advantage being an established couple also, and you were right in thinking that the personal services could be of a sexual nature. I think I’m OK with that. After all, it wouldn’t be much different from the couple of orgies we’ve attended, would it?”

“Probably not, but those were fairly tame with people we knew well, these may be a bit different,” I replied, aware that, unusually for me, I was now playing the cautious partner. “However, let’s see after our appointment.”

We spent the remainder of the morning sorting and packing our belongings ready to move out. Summer stuff went into our packs, winter stuff into boxes to go into storage. We weren’t likely to need our books and academic stuff so that also was destined for storage. After lunch we walked the short distance downtown to attend the interview.

“Welcome to Pleasure Island Vacations,” greeted the very attractive young woman who came around from behind the desk and gave us each a hug. “My name’s Sasha, and you must be Tina and Jeff, right?”

We agreed that she was right, and she showed us to comfortable chairs in the corner, where we sat for what turned out to be a pre-interview chat, during which she skilfully discovered a great deal of information about us, what we were studying, how old we were, where our families were based and the nature of our relationship. After about ten minutes, the door opened and a very sporty looking guy walked in and joined us, introducing himself as Brad and shaking my hand before giving Tina a slightly more prolonged than polite hug. I noticed she was slightly flushed when she sat down and he pulled a chair over and sat beside her.

Our interview proper now began with Sasha taking notes while eryaman genç escort bayanlar Brad did most of the questioning. After he appeared to be satisfied with the details, he then explained a bit about the Pleasure Island Vacations business. It was essentially a tourism venture which owned exclusive rights to occupy and use a lavish and luxurious resort complex on a privately owned island. The resort catered for the rich and famous who wanted absolute luxury and privacy and were prepared to pay for it.

“We have a very high ratio of staff to guests, allowing for exquisite service in everything that the guests desire. Their word is final; if it is available, we will find it and provide it, regardless of cost. We have access to several private jets to fly goods and people in for our guests’ pleasure. This is where you come in. As service personnel, you would be assigned to a couple for the duration of their stay, usually a week, although some stay longer, catering to their every whim at any time of the day or night.”

Brad paused and looked at us to check our reactions. We were both smiling, waiting for him to continue.

“You will live on site, of course, and meals will be available for you in the staff dining room. Believe me, those meals are really something. I guess that as you’re relying on this work to fund your studies for the next year, you’ll be interested in the financial arrangements. Accommodation and meals are free of charge, so essentially you have no living costs, and you’ll be paid a small retainer. Where you do make your money is in tips. Service staff can usually rely on receiving around $100 per day each if they’re doing a good job of providing what their guests desire. Obviously, if they are unable or unwilling to provide a sufficiently high standard of service, that will be considerably less, and we’ll also hear about it and replace that staff member as soon as possible, unless, of course, we consider the request made by a guest to be unreasonable.”

Brad stopped talking and looked at us, as though waiting for expected questions. I glanced at Tina, saw she was bursting to ask a question, as was I, so I nodded for her to go first.

“What sort of services might guests want and what sort of services might we be unable or unwilling to provide?” she asked.

Brad glanced at Sasha, as though silently consulting with her, then replied. “It should come as no surprise to you, as mature adults, that many of the services you’ll be required to supply may be of a sexual nature. You may also be aware that the rich and famous are often slightly, or very, weird in their sexual preferences for some reason, possibly because they can, possibly because they enjoy the thrill of doing things which normal people would either be unable to afford or for which they would be unwilling to accept the consequences. This could include normal sex, of course, as well as oral and anal sex, cross-dressing, bdsm, orgies and other bizarre practices that they may have dreamed up.”

Brad paused, glancing slightly nervously at each of us, as though judging how we were accepting this revelation. I was unsurprised, expecting something of the sort, and looked nervously at Tina, expecting her to display horror and distaste, or to be prepared to walk out. Instead, she had a broad grin on her face. I was even more surprised when she replied to Brad.

“Sounds like fun to me. Where do I sign?”

It was at that stage I realized that, even though we’d be living and loving together for three years, I didn’t yet know the real Tina.

That evening we continued packing up the apartment, then sat with glasses of wine recounting the remainder of the interview. Once Brad had ensured that Tina was OK with what he was proposing, he asked us to complete official application forms, then told us there was a final test we needed to pass. He and Sasha stood, and each held a hand out for us to go with them, Brad leading Tina to one door while Sasha led me through another. Tina and I hadn’t shared what happened in the separate rooms yet, so over a glass of wine we opened up to each other. Tina won the rock-paper-scissors, so she went first.

“Once we were inside, Brad asked me to strip as sexily as I could. I imagined stripper music in my head, some of the same music that played at the strip show we visited last year, remember, and I slowly and, I hope, sexily removed my top and skirt, leaving me with only my frilly pair of panties on. I then slowly and sexily walked over to Brad and asked him to remove my panties with his teeth. He, of course, grinned broadly as he knelt down and gripped the elastic with his teeth and pulled them downwards, slowly exposing my shaved pussy that you know so well. I stepped out of my panties as he rocked back on his heels to catch a full eyeful of my naked body. He reached towards me but I batted his hands away, determined to prolong his agony of lust for as long as possible.

“I pranced around in front of him for a short time, ankara escort bayan bending over, spreading my legs and lips, which were flowing with my juices by now, and never allowing him to touch me. Then I commanded him to stand and slowly kissed him, holding his arms down so he couldn’t touch me, then I slowly stripped him, shirt, trousers, underpants, causing his rock-hard cock to spring up in the air as it was released. I again knelt in front of him and caressed his cock and balls, before engulfing his cock with my mouth. You know how I like deep-throating you, well, I did that to him and it just about drove him nuts. I was very careful not to allow him to cum though.”

I put my drink down and unfastened my shorts, pushing them downwards until my own rock-hard cock sprung upwards. Tina reached for it and held it as she resumed her story.

“I asked him how he wanted me and he said he wanted me to ride him hard. So, he lay on the bed and I straddled his legs, edging my way up his body as his hands kneaded and caressed my tits. He squeezed and twisted my nipples just like you do, and, as you know, that drives me wild. I moved up his body faster, lifting off him to position his cock at my sopping entrance, before sitting down on him hard. I loved the way he moaned with pleasure, just like you do sometimes. After that, it was pretty much routine. I moved back and forth, he came in me quite quickly, then I leant further forwards and concentrated on my own pleasure, cumming noisily a few moments later. You probably heard me.”

“Yes, I did, your trademark scream followed by loud grunts as you finished off.”

“Then we dressed, except he insisted on retaining my panties, which is why I’m commando now.” Tina lifted her skirt to show me and took a sip of her wine. “Anyway, that’s my story, how about yours?”

“Well, I might be able to help you there,” I replied with a grin, reaching into my pocket and removing a pair of panties, which I offered to Tina, “Sasha insisted I take these; she said I’d probably find someone who needed them.”

Tina laughed out loud, then stood up, took them from my hand, sniffed them then pulled them on. They fitted really well and looked far sexier on her than in my hand.

“Looks like she’s much the same size as me,” she chuckled as I stroked her panty-clad pussy lips, “Anyway, your turn; what happened with Sasha apart from her giving you her panties?”

“Well, once the door was closed, she pressed her body against me and we kissed while we both caressed each other’s ass through our clothes. Then she whispered in my ear ‘Strip me, darling, slowly and sexily.’ Well, you know how I do that, so I did it exactly as I do it for you, removing an item at a time, slowly, kissing every square inch of newly exposed skin as it made its appearance. Her nipples were engorged and she let out little moans as I kissed and sucked them, while she couldn’t resist stroking my now hard cock. I was pleased we’d made love this morning or I might have cum too soon, such was my arousal.

“Eventually I knelt down and slid her panties to the floor, not with my teeth, however; my mouth was busy licking and sucking her gorgeous pussy which had only a very thin, blonde landing strip ending just above her prominent clit. I spent some time sucking her pussy, using my tongue to stimulate her clit while she pulled my head into her crotch. I must have been doing this for around ten minutes when I felt her tense, press her hips against me and heard her breathing change as I tasted her juices flooding down her passage. I realized then that she’d cum on my tongue, so I looked upwards into her eyes, seeing her lustful grin. ‘Fuck me, darling,’ she said softly, ‘Hard.'”

I wriggled around a little as Tina lay on the sofa and took my rigid cock into her mouth, not sucking, just allowing it to be there as one hand caressed and gently squeezed my balls. After a few seconds, I continued.

“I stood up and scooped her into my arms, carrying her to the bed and laying her gently on her back. ‘How do you want it?’ I asked, and in reply she simply bent her legs, gripped her knees with her hands, then spread them wide apart. ‘Hard, sweetie, as hard as you can,’ she replied. I took this as a signal that she liked it a bit rough, so if that’s what the lady wanted, that’s what she’d get. I knelt between her thighs, adjusted my position until my cock head nudged between her puffy, wet lips, then thrust in and down as hard as I could. An ‘Ooooff’ came from her mouth as I penetrated her deeply with one thrust, my pubic bone pressing against her clit but my cock not reaching the end of her cunt. She must be huge, because I’m certainly above average size.”

“Well, Brad’s certainly no larger than you are, so Sasha hasn’t been elongated by him. Be interesting to find out how she became so large once we know them a bit better. Maybe I’ll use that method for you, darling.”

“Hmm, well, I quite enjoy pressing against the end of your cunt; etimesgut escort feels good. Anyway, I began sliding in and out, focusing on pressing against her clit to increase her arousal and enjoyment. It wasn’t long before she was lifting her hips to meet my thrusts, her hands on my ass cheeks pulling me into her deeper and her breathing becoming faster and shallower. I cupped her tits in my hands and began squeezing her nipples hard in time with my thrusting inside her. She moaned an almost continual low moan as her head rolled from side to side, then she wrapped her arms around me and pressed her head against my chest to muffle her cry as she writhed in the ecstasy of her orgasm. I continued to thrust inside her as she came, until she was obviously coming down from her peak, when I slowed until I was sliding gently in and out, using my cock to massage her from the inside.

“She reached up and pulled my head down, kissing me hard on the lips before whispering in my ear ‘Fuck my ass, lover.’ It’s not my favorite pastime, as you know, but right then her wish was my command. I slid out of her and she flipped over, presenting her sopping pussy and tight asshole for my pleasure. I spent a few minutes loosening and lubing, using her copious juices until I could slide first one and then two fingers into her tight rear passage. I then pressed the slippery head of my cock against her asshole and pressed in firmly. Slowly I entered her, sliding in to gain some ground, then withdrawing part way, and in a little more until I was completely inside her. She moaned softly, then told me how good it felt. ‘Just gently, and I want you to squirt in me,’ she told me, ‘I won’t cum again’.

“I knew this wouldn’t take long; the whole eroticism of the situation meant I’d been holding off for some time now. I fucked her ass for several minutes, slowly and gently feeling my arousal growing. I reached around her and grasped her swinging tits, once again squeezing and pulling her nipples, resulting in several moans and shudders from her body. Without meaning to, I realized I had sped up and was thrusting harder as my orgasm approached; then I was there and spurted my hot cum inside her ass as she let out a loud moan as she came once again, her body shuddering beneath me as I filled her before she collapsed forward and downwards, and I went with her, lying on her back, my cock still twitching involuntarily deep in her ass.

“We cleaned up and dressed, she thrust her panties into my pocket and we returned to the interview room to re-join you and Brad. I wonder if they’ll be on the island with us. Wouldn’t mind another session with Sasha.”

Tina gave me a playful thump on the arm. “Remember, have as much fun as you like, but you’re mine, right?”

“Right, darling, same goes the other way. It’s really great to be able to trust one another and allow each other to have sex with other people, yet remain true to each other. After all, if you really love someone, wouldn’t you want then to have all the joy and pleasure and excitement possible? Why would you limit that by insisting on boring monogamy?”

“You’re right,” replied Tina, “I’m so pleased we agreed on this soon after we first met. Think of all the fun we’d have missed if we just fucked each other. We’ve had some really enjoyable and loving fuckfests, and hopefully we’ll have lots more in future. This summer sounds like it’s shaping up to be very memorable.”

Tina stood up and took my nearly empty glass from my hand, placing it on the table with hers, then took off Sasha’s panties and spread her legs as she straddled my legs until she was directly above my hard cock. Then looking me in the eyes to watch my reaction, she did her special trick of allowing her feet to slide sideways, lowering her pussy onto my cock as her widening stance spread her lips apart. She was athletic enough to do the splits on the floor, so she continued to drop as I entered, then slowly penetrated deep inside her love tunnel, until she had all her weight on me rather than on her feet, which she even managed to lift off the floor for a short time. She then leant forward against me, my pubic bone pressing even harder against her clit, and lay her head on my shoulder, both of us feeling completely fulfilled and satisfied with life as it was right then.

It normally took ten minutes to reach Pleasure Island from the mainland airport, but that was for guests and travel was by helicopter. Our trip to the island took over two hours by supply boat from the dock. This gave us plenty of time to observe the views as we slowly approached the island and also gave us time to chat with the boat’s captain, who filled in many of the details about the behind-the-scenes activities that occurred on the island. It turned out that he was a staff member and spent much of his time on the island, helping out as required and occasionally taking part in some of the more enjoyable activities.

“Usually the customer service staff look after the guests, but occasionally, usually near the end of the season, everyone, from grounds, restaurant, maintenance and administration are invited to an end of season party, which invariably turns into an all-night orgy. Some guests enjoy that experience so much that they book for that time each year,” he explained.

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