Pleasure Island Ch. 05 – Erotic Couplings – Free Sex Story

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Trudi, Dennis, April and Tony

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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As we entered the meeting room, the first thing we noticed was that there were far more service staff than usual, probably meaning that most or all clients had departed. That would explain why there had been so much air and sea traffic this morning. We chatted with others and partook of the refreshments that were on offer, until after a short time, during which a few others arrived, Betsy walked in and made her way to the front. The hubbub of chatter slowly died until she could begin.

“Good morning, everyone. Well, what a wonderful few weeks we’ve had. I hope you’ve all enjoyed it as much as your clients seem to have.” There were murmurings of agreement. “Now I realize that many of you are approaching the end of your time here, so, as usual, for your final week before part-timers return to their studies, we have something slightly different planned.”

She paused, looking around the room. I wondered what special event could be planned for the remainder of our time here.

“Many couples experience boredom with one another after a while. They don’t want all the hassles of divorce, yet they seek variety, a modern-day manifestation of the possibly ancient caveman need to have several partners to increase procreation. Many also enjoy polyamory, which in this context would be enjoying Sex with more than one semi-permanent partner. Interestingly, it seems to be as applicable to women as to men these days. So, this week becomes a swinging party, where couples or trios, usually members of one of several Wife swapping, swinging or polyamory clubs, come here to mix and match as they wish. Indeed, some couples choose a different partner and go home together, living with that partner for a year before returning to swap again the following year, maybe going back to their original partner, maybe someone new. Regardless, it’s always a fun time.

“There can be several motivations for desiring a multi-partner relationship. One of the motivations for these exchanges is that partners have different desires which may not be met in their normal relationship. A classic example is that of one partner wanting BDSM activities while the other partner does not, or partners enjoying exhibitionist or voyeur activities which they cannot achieve with their partner. So, by mixing here, they can usually find someone or some situation in which to act out their desires, allowing them to satiate this need without any long-term disruption to their lives. Another motivation could be that one of the partners, usually a male, is infertile and his partner wishes to have a child, so they partner with a couple with a fertile male to make a child a possibility. These are two obvious cases; there are, of course, many more.”

Betsy paused and surveyed the group, noting looks of puzzlement as well as smiles of anticipation.

“I’m sure that those of you who have not experienced this week before are wondering what your roles are. As usual, they are to facilitate and expedite required services for our valued clients. There are several ways of achieving this, as you are undoubtedly aware. You could provide a service yourself or you could facilitate the fulfilment of a desire by finding someone else to provide a service. Your level of participation is, as usual, up to you; remember that your participation in anything is always voluntary, but for this week, your role is primarily to ensure that the clients can interact with each other in whatever manner they wish. However, remember also that you’re here to make money as well as to have fun, so the more you participate, the more money you’re likely to make in tips. Basically, however, just continue to provide the excellent service you have been providing, volunteer only for what you wish, and you’ll be fine.”

Betsy paused and looked around the room, judging our responses.

“The other aspect is that, due to the flexible nature of the groups this week, you are not assigned to a particular couple. This will mean that you are expected to provide reasonable services for whoever requests them. Service personnel in previous years have found that during this week they tend to associate with a few couples for whom they provide or organize any required services, so don’t feel that because you are not allocated to any specific people, you have to meet the requests of everyone. That is neither beneficial for you nor for anyone else. Have fun and enjoy. Clients will begin arriving around 10am tomorrow morning, so please make yourselves available from then when the helicopters and ferries begin to arrive. Until then, you have some time for yourselves. Are there any questions?”

Betsy paused and people began talking softly amongst themselves

“Sounds like fun,” said Tina.

“Yeah, sure does,” I agreed.

Someone raised their hand and Betsy acknowledged them, waiting until the murmuring died away before signalling to speak.

“Do the clients belong to any organization or are they all in couples or small groups, or even singles?”

“Good question, thank you. The majority of them belong to one of two types of organizations, either a polyamory partner swapping club or a BDSM club, but there will be several of each type represented here. There are usually a few freelancing couples, but we do not cater for singles. That could upset a whole lot of people and change the sharing ambience of the event. It is very usual for club members to observe other members as they undertake activities and club members are usually very welcoming of other members and non-members who wish to participate; in fact, I have been told that the clubs have gained many members from these weeks.”

Betsy paused for a few moments to let this information sink in.

“You could be excused for thinking that this week is one massive and continuous orgy.” She paused and grinned. “In which case you’d be mostly correct. The other thing I haven’t mentioned is that on the last night there is a special event which I’m sure you’ll all enjoy. Any other questions?”

There was considerably more chatter after that announcement, but no further questions, so Betsy again addressed the service personnel. “The one part of the resort which tends to become overloaded this week is the dungeon. Therefore, we are converting the rec room into a second dungeon-like atmosphere, so we need to install temporary equipment there this morning as well as place foam pads on the floor adjacent to the walls to provide more group activity spaces and also a venue for the final night’s activities. It’s quite likely that during the week you’ll find you spend some of your time in the rec room rather than in your own units, but I advise you to just play it by ear. So, before you leave this morning, can you please help with installing the equipment.”

We followed Betsy to a store room and for the next hour or so helped move foam pads, massage tables, whipping and caning frames and tables as well as other restraint equipment into the rec room, setting it up ready for use tomorrow. Then Betsy thanked us all, told us to enjoy the rest of the day at leisure, and people began leaving. Betsy made her way towards us through the small groups.

“How’s it going, Tina and Jeff?” she asked with a grin.

“Really great, thanks Betsy.” Tina replied.

“Good. Pleased it’s not all one way.” We must have looked puzzled because she hurried on. “I’ve received several reports from your clients. Invariably they have given you excellent ratings, so congratulations.”

“Thank you,” I replied, “It’s definitely been a pleasure, I can assure you.”

“Also, congratulations to you, Jeff. Beth tells me you’re going to be a daddy. She had a positive pregnancy test yesterday and sounded overjoyed on the phone, so well done.”

“Thank you. I assure you that also was a pleasure.”

“Jacqui and Becks also contacted me and told me that they also think they’re pregnant, but haven’t had tests yet. So, you must be doing something right. Do you guys have anything planned for today?”

Tina and I looked at each other and shook our heads.

“Great. So, would you object too much if I spent some time with you now? I’d Love to see how accurate all the rave reviews about you are.”

I’d envisaged a quiet day relaxing under the palms, swimming and making Love with Tina, but our plans were very flexible and it could be fun to spend some time as a threesome with Betsy. I checked with Tina, who nodded, then told Betsy that we’d Love to spend the day with her. We arranged to meet by the pool in an hour.

We returned to our room, tidied it up, sorted dirty clothing and linen and took those to the laundry, made the bed with fresh linen and walked down to the pool to find Betsy already waiting for us. We were, as usual, naked, but Betsy was wearing what I guess could be called the tiniest bikini in creation. Basically, it was a thin strap around her waist with another thin strap from front to back through her crotch, disappearing between her Pussy lips in front and reappearing from between her Ass cheeks behind. The top, if it could be called a top, was the same thin strapping holding rings over her aureoles through which her nipples protruded. These were pierced by two gold rods which also passed through holes in the rings on both sides of her pierced nipples. The rings were fastened together in front and tied behind her back, with another strap from her rings going around her neck, effectively holding her ample breasts up higher than would be natural.

“Wow,” I commented, “I Love the outfit.”

Betsy grinned. “You ain’t seen the half of it yet, sweetie. Have a good look at it.”

I did, making sure I cupped her breasts, feeling their firmness. I pulled up on the top strap and her breasts lifted higher, before dropping slightly when I let go.

“That’s cool,” I said, “I Love the effect. Maybe you could get your nipples pierced, eh honey,” I suggested to Tina.

“Mmmm, a definite maybe,” she replied, “I’d just need to see what you’d be willing to trade first.”

“Do you want to investigate further?” asked Betsy.

“You mean there’s more surprises?” I asked.

“Oh yes, come with me.”

She led us to a padded bench and lay down on her back, legs wide apart with feet on the ground on either side. From this new angle I could see that there was a plug of some sort in her Pussy, with the crotch strap of the bikini passing through a hole in the end. I knelt down between her legs for a better look.

“What is it?” I asked.

“Just a dildo,” Betsy replied, “I like feeling full so I like to feel something inside me. I usually wear it for several hours each day, but in my official capacity, I’m usually at least mainly dressed.”

“How big is it?”

“The end is only an inch across, but further inside it flares to two inches. Here, feel it.”

She took my hand and pressed it against her belly just above her pubic bone. I could feel a hard rounded lump inside. I moved my fingers upwards and found the end of it.

“How long is it?” I asked.

“This is the eight inch one. I can keep it inside all day. I have a ten inch one as well but it is too uncomfortable to keep inside for long. However, each evening I try to keep it inside for a bit longer. Those are my cunt training sessions. Anyway, enough of me, let’s have a swim.”

She sat up and we all walked the few steps to the edge and dived in, swimming to the other end, then sitting on the underwater step. I was hard from the thought of what Betsy had inside her, but, of course, Betsy couldn’t take advantage of that, so Tina did, facing me and straddling my thighs. I felt myself sliding into her warm Love chute as she pressed her nipples against my chest and lay her head on my shoulder.

“I Love you, darling,” I heard her murmur against my neck as she kissed me.

I stroked her head while watching Betsy as she sat alongside me, rocking her hips gently to move the end of her dildo, which obviously stimulated her.

“Are you able to cum just from wriggling the dildo inside you?” I asked.

“I wish!” she exclaimed, “No, so far, not quite. This means that I can sit in my office and move my hips, arousing me but never quite enough. Really frustrating, but it sure makes my release amazing, once I finish work.”

“I’ll bet. So best scenario, what would you like to do this afternoon?”

“I want you to fuck me at least a couple of times. I’ve heard that your recovery time is really short, so I want to put that to the test. You up for that, honey?”

I grinned, anticipating an interesting afternoon. “Sure thing,” I replied, “And I guess I’m not required for breeding this week either, so no need to conserve sperm.”

We only spent a short time in the pool then we climbed out and dripped dry as we walked to our room. Once inside, I made us drinks and we all piled onto the big bed. Betsy immediately lay on her back and spread her legs wide.

“Can’t fuck with it in, darling, so I suggest you remove it.”

I untied the waist strap and pulled the crotch strap down, then began pulling the dildo out. It was more difficult than I’d expected due to the larger size that was inside her, but it slid out, stretching her opening until it finally plopped onto the bed.

“Can I try it please?” asked Tina, kneeling on the bed with her knees wide apart.

“Sure,” replied Betsy, “Lie on your back and I’ll help you slide it in. Could be a bit tight first time.”

She lay on her back, legs wide apart, and Betsy knelt between her thighs and placed the end between her labia at her entrance. Tina was wet from arousal and the dildo was still wet from Betsy’s cunt, so, with only a little persuasion, Tina’s labia spread apart and the dildo slid inside. Betsy removed her hand and allowed Tina to push it all the way inside until the last inch seemed to slide in by itself due to the narrowing at the end. Tina had a look of concentration on her face as she’d craned her head forward watching the monster enter her, but now she smiled at me triumphantly.

“It fits perfectly,” she told us, “Just touching the end. It feels great; I feel so full. I think I’ll have to get one. Just imagine attending lectures with this inside; it’d be such fun. Then you could pull it out each afternoon and fuck me till I couldn’t stand.”

“Sounds like fun to me,” I replied, grinning.

“Maybe it does and maybe it will be, but right now I feel empty and I want a real cock inside me. Come on, darling, fuck me hard.”

Betsy was kneeling on the bed so I pushed her sideways, spread her legs apart, placed my arms behind her knees and pushed them apart and upwards, spreading her wide open as I positioned the head of my cock at her gaping entrance. I rested on my elbows and cupped her breasts, squeezing the pierced nipples and eliciting a low moan from Betsy.

“That’s sooo nice, but push him in me, darling, don’t keep me waiting.”

I began nibbling and kissing her breasts alternately as the head of my cock rested just inside her entrance. She wriggled her hips, trying to suck more inside, but to no avail. This continued for several minutes as Betsy became more and more frustrated. Just before I decided that she’d had enough, I was startled by a hard spank on my Ass. My reaction thrust my hips forward, my cock sliding effortlessly inside Betsy’s oozing cunt, until my pubic bone pressed against her clit.

“Thank you, sweetie,” said Betsy, looking over my shoulder.

I began thrusting in and out of Betsy’s cunt hard and fast, each inward thrust causing her to emit a grunt as the force expelled air from her lungs. It took only a few moments before she started rolling her head from side to side, making a high-pitched keening wail, which I was to learn was her sound as she approached her climax. I didn’t let up, and felt her body beginning to shudder beneath me, her hips pushing upwards to meet each thrust, then she clutched my back hard, digging her nails into my skin as her body seemed to go into orbit.

“YES, YES, YESSSS, I’M CUMMMMMMINGGGGGG!!!” she screamed, her body shuddering.

I stopped moving, holding my cock fully inside her as her clasping cunt contracted around me, trying to suck my cum, which I wasn’t yet ready to give. I remembered that she wanted to test my recovery time, so I decided she needed a couple of orgasms at least before I shot a load into her, then a few more afterwards for good measure, I hoped.

Gradually she calmed down, her breathing easing, and she grinned up at me.

“That was wonderful,” she said softly, “Again?”

“Again,” I confirmed as I began moving inside her once more, fingers stimulating her hardened, pierced nipples as I ground my pubic bone against her clit. It took less time this time before she was shuddering, the keening wail, then she was Cumming hard once more as she writhed beneath me. I managed to hold back that time also, but doubted I could do it a third time.

Again, after a short break, I began fucking her hard, feeling myself approaching my climax as I thrust deeply inside her pulsating cunt. I squeezed her nipples again, causing her to moan, then begin her keening wail once again as we both approached our climaxes. I felt my body beginning to clench up and deliberately relaxed and slowed down as she moved against me, thrusting upwards, seeking more stimulation. I stopped moving, allowing her to do all the work, the effort of lifting her hips and thrusting onto my hard cock was pushing her towards her next release, just as it was pushing me to mine. A few more thrusts and I’d be there. I began thrusting again, pushing into her hard, squeezing her clit between our bodies as she began her wail once more. I pulled out all stops and thrust into her harder, feeling my Hot cum spurting through my cock and into her clasping cunt. She obviously felt it filling her as her body went wild, shaking, shuddering, writhing in ecstasy beneath me as waves of release poured through me.

It was over in a few moments. I collapsed onto her still-shuddering body and we both relaxed, our heavy breathing gradually slowing. I pushed myself upwards and released her legs, looking sideways towards Tina, sitting on the edge of the bed, stroking her Pussy with her fingers.

“Looked like a good one, honey,” she said with a grin, “I Love watching you cum in someone else.”

I gave her a wink, then sat back and gazed down at Betsy, looking far more dishevelled than her usual tidy self.

“You want more?” I asked with a grin.

“You got more?”

“Sure, there’s more, unless you’re too exhausted. You’re on top this time.”

I lay on my back beside her as she sat up and straddled me, crawling upwards until our lips met and we kissed lovingly, tongue wrestling for a few seconds before she sat back, then wriggled down my body a little, leaving a trail of our juices, until she could hold my cock. She stroked it, feeling it harden in her hands as it again readied itself for action.

“Seems he wants more,” she said, “Are you completely insatiable?”

“Don’t know. Do you want to find out?”

“Well, it would be fun.” Then Betsy turned to Tina. “Or I could just ask,” she added with a grin.

“Once only he’s been so fucked out that he couldn’t get it up, but I think I’d had about a zillion orgasms that weekend, and he’d cum a dozen times at least.”

“Hmmm, I think I’ll take your word for it then.”

I was once again hard and ready and she placed her Pussy over my cock and moved back and forth, massaging her trench with my hard cock as I felt him growing harder from the stimulation. Then, without warning, she slipped him inside and sat down hard, pressing her clit against me as I probed the end of her cunt. She then started a gentle back and forth movement, causing my cock head to move deliciously over her cervix while she massaged her clit against my hairy pubic bone. She tilted her head back and closed her eyes, enjoying the sensations as I moved my hands to her tits again, playing with her engorged nipples at first then gently squeezing them as her back and forth movements increased in pace.

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