Pleasure Island Ch. 02

"Just so you know, Colin has had a vasectomy so he can't give me a baby, which I most definitely want. So, Jeff is doing the honors this week in an effort to impregnate me. Therefore, I need all his cum so sorry, ladies, he's not allowed to cum this afternoon, he has to store it up for me tonight."

"That's not very fair," commented Georgia, stroking my cock through my tight shorts, "Making guys cum is the part I like most."

"Well, Ok, I'll relent a little. You can make him cum, but only once and only if he spurts deep inside my pussy. I don't want it to go to waste. Who knows, the sperm to impregnate me might be the next one in line."

"I don't think it's quite like that," chuckled Georgia, "But Ok, if you insist on that I'll take great pleasure in causing him to lose his load inside you. I'm sure that Terry will be only too willing to let me drain him, won't you darling?"

Terry gave her a hug as he agreed that he'd look forward to the opportunity to pump her full of his sperm. Just then the dungeon Domme, Sylvia, arrived and took control, having everyone kneel before her, her multitailed whip being used gently on Terry and Colin, who showed initial reluctance to obey her orders.

"You have a choice here," Sylvia began her pep talk, "You can obey me or you can receive punishment and then obey me."

She continued her introduction with a few safety rules, specifying the safe word and its use, then ordered us to our feet and we all filed into the inner room. While Tina and I had looked inside on the orientation day, this was the first time we'd been able to have a good look and to wonder what the equipment was used for. Sylvia consulted a page of paper before announcing what would be happening.

"I see that Georgia has requested mainly sexual and bondage type activities rather than any punishment, but she has permitted me to administer gentle punishment if I consider it necessary. Rather a shame really, a waste of fresh skin; nothing I like better than to send a group like you out from here with reddened asses from a good caning. Oh well, I'll just have to look carefully to see who deserves to be punished."

"I'd like to make a request, please mistress," said Beth nervously.

Sylvia glared at her. "Yes, what is it?"

"I'm trying to become pregnant with Jeff, so if he's made to cum, and I hope he isn't because he usually does that with me each night, that he spurt his sperm deep into my cunt, please Mistress."

Sylvia gave one of her rare smiles. "I'm sure that can be arranged. I think possibly a good dose of arousal while withholding his orgasm would be very effective also. I assume that you do not want Terry or Troy to cum inside you either in case they, not Jeff, impregnate you."

My heart sank. I was teased each morning by Tina without having to suffer an afternoon arousal as well. Oh well, I guess this was all part of the service for which I'd been employed.

"Yes, that's correct, Mistress," agreed Beth.

"So first off, you need to strip each other, after which I'll see what I can organize to meet your needs."

Sylvia arranged us into pairs so that we each stripped another. I stripped Georgia, slowly, caressing her body as she was slowly revealed, cupping and massaging her breasts and stroking gently between her legs, feeling her warmth and womanly juices begin to flow. Then she stripped me, gently squeezing my balls before softly stroking my almost fully hard cock.

"You're going to have a hard time not cumming, I think," she commented, as she pressed her warm soft body against mine, spreading her legs so my cock could slip between them, before kissing me very sexily. She moved her lips to my ear, then whispered: "I want you inside me before I go home again. Terry and I are here for two weeks, so I'm going to see if you and Tina can service us next week, lover."

We'd barely started the dungeon session, and I felt myself a few thrusts away from losing my load as Georgia kissed and caressed me. I tried to focus on math problems to take my mind off her soft, luscious and willing body, but found it impossible. Fortunately, Sylvia began speaking so we all stood apart and listened to her words, nobody wanting to be the one punished.

"Come with me to the sex swings," Sylvia said, moving to a corner of the room where two swings hung from ceiling beams. "Who would like to ride the swing first?" she asked, looking at the four women who were all concentrating on not meeting her gaze. "Sue, you know the drill, don't you?"

Sue tried not to appear too eager as she stepped forward. "Thank you, Mistress, I'd love to demonstrate the swing. I think it's almost my most favorite thing here."

She positioned herself on the swing as Sylvia fastened the straps around her hips and shoulders, then she cuffed her wrists to her bent knees and to the swing so her arms held her thighs wide apart, presenting her pussy that extended slightly over the edge of the swing. We could all see her opened labia, shiny with her juices, alongside her moist slit, just waiting to be penetrated.

"Who would you like first?" asked Sylvia.

"Well, the only guy I haven't had is Colin, so I guess he's first."

Colin stepped forward and took his place beside the swing, facing Sue. Sylvia tilted the swing and raised it slightly until his cock lined up perfectly with Sue's opening.

"You ready, Colin?" she asked.

"Sure, what do I do? Just push into her?"

"Oh, no. It's far more fun than that. Just step back a little, Colin, then I pull Sue back and she swings forwards. Your goal is to enter Sue as she swings towards you; her goal is to hold on so she doesn't swing back. Sue needs to clench her pussy muscles as tight as she can when you get fully inside. Too soon and you won't go all the way in, too late and you'll come out. Ready?"

Colin nodded, a look of concentration on his face, and Sylvia pulled Sue back a little then released her. She swung towards Colin's cock as he watched his target approach, but he missed, his cock pressed into her upper thigh an inch from her entrance.

"Ow," cried Sue as Sylvia pulled her backwards again for the next attempt.

Sue swung towards Colin's cock once again and this time he found his mark. His cock entered Sue's tunnel part way, then she swung backwards, sliding off him, unable to hold on.

"You need to go in further," Sylvia told Colin, "So I'll swing Sue back a little further now you've got your eye in."

The third time Sylvia drew the swing back further, Colin lined himself up with his target, Sylvia released the swing, which travelled much faster towards Colin, but his aim remained true and he speared Sue's entrance as her momentum caused her to completely engulf him, ending with an audible thud as their groins came together. For a few seconds it looked like Sue might slide off again even though the concentration on her face showed all her focus was on holding on, but then they stopped moving, Colin deeply implanted inside Sue as she gripped his cock hard.

"What now?" asked Colin.

"You mean you don't know?" asked Sylvia with a grin, "You've impaled her, she's held on, so now you fuck her. Cum if you like, make her cum if you want, over to you."

Colin took a step forward, allowing Sue to relax her grip, then he began sliding out and pushing back inside as he held her breasts with both hands, squeezing her nipples between thumbs and fingers. I watched Sue close her eyes, a grin on her face as she enjoyed the feeling of Colin fucking her hard, their bodies making wet slapping sounds each time they came together. I became aware of Beth, one arm around my waist as she gently caressed my rock-hard cock, her gaze fixed on her husband fucking Sue on the swing.

After a few minutes, Colin pushed Sue away, withdrawing from her.

"Someone else want a turn?" he asked, looking at Terry and Troy.

"Yeah, I'll have a go," replied Terry, "Then Troy can fuck Georgia. Deal?"

"Deal," said Troy, grinning.

"Hey, don't the girls have any say in this?" protested Georgia.

"You can fuck who you like, so long as I get Jeff's and only Jeff's sperm," replied Beth.

Sylvia suggested that Beth use the other swing so we both moved the short distance and Sylvia helped Beth into the swing. I watched partly, but also kept an eye on the swing with Sue. Terry had stepped up to the swing and prepared himself, then pushed the swing gently backwards, allowing it to swing forwards until his cock pressed to the left of Sue's gaping entrance. A slightly harder push and he ended up slightly to the right, then, with a grin, he pushed her away harder and entered her easily as she swung back, moving about half way in before she slipped off. Sue grinned encouragingly.

"Harder, lover," she coaxed.

He pushed her swing harder then took a small step backwards and positioned himself perfectly to fully penetrate her slippery love tunnel as she reached him. Again, Sue focused on holding him, but he slipped out as she swung back. Another swing, another penetration, same result.

"The second person is lots harder to grip than the first because your pussy's more open and more slippery," said Sylvia, grinning as she saw Terry and Sue's predicament. "It's possible that what you've got is all you'll get, but keep trying anyway."

They tried another ten or so times, without success. Sue was becoming frustrated while Terry thought it was great fun.

"I want to cum," protested Sue, "Ooohhh, I need to be fucked hard."

"So do I," complained Beth, temporarily abandoned on the swing.

I turned back to her and positioned myself before Sylvia pulled her swing back, then released it. She swung towards me and I missed, adjusted my position slightly, then pushed her away from me. This time I entered her partially, but Beth wanted more of me, she was done waiting.

"Just fuck me," she cried, "Forget the swing, fuck me and make a baby in me."

I gripped her waist and pulled her fully onto me, feeling the head of my cock press against her cervix. It felt like my cum was boiling in my balls and I thrust hard inside her several times, before relaxing a little and focusing on arousing her some more. She was almost ready, it seemed, and protested my gentler approach.

"No, harder, much harder, honey, I'm almost there. Fuck me hard, fill my cunt with your cum."

I increased my thrusting, fucking into her as hard as I could as her keening wail began, rising to a crescendo as I made a final thrust and stayed inside her, filling her with my potent seed as she writhed around, confined by the bonds holding her to the swing.

It was over in a few seconds, it seemed, and I relaxed, feeling her pulsating cunt walls milking the last of my cum from my softening cock. I looked over my shoulder in time to see Terry cumming inside Sue as she moaned and writhed in orgasm on the swing.

Georgia and Troy were kissing, waiting for their turn on the swing, Colin was sitting, recovering it seemed, and Tina appeared to be at a loose end.

"Tina, you want to try a Sybian?" asked Sylvia.

"Never heard of it. What's it do?"

"Well, what doesn't it do would be a better question," replied Sylvia as she opened a cupboard and wheeled out the machine. She showed Tina how it worked and some attachments as Colin, Sue and Terry joined and listened in, then she invited Tina to ride first. I watched as my darling selected a seven-inch dildo then mounted the machine, the dildo sliding easily into her aroused tunnel. I unfastened Beth from the swing as Sylvia fastened Tina's knees to the base, preventing her from lifting off the machine. She then explained the workings of the remote and handed it to Colin with a grin.

"Give her a good ride," she instructed, "But don't let her cum too soon."

Colin adjusted the machine so it was rotating and vibrating at a moderate pace, causing Tina to grip the end of the machine with a vacant look on her face as she felt the arousal pulsing through her. She began moving her hips slowly, sliding her clit over the vibrating fingers. She sat back to gain balance then cupped her breasts and squeezed her nipples hard, pulling them away from her chest as her arousal increased. She began moaning and Sylvia indicated that Colin should tone the stimulation down a bit, which he did.

Tina opened her eyes and glared at Colin, who simply grinned, knowing that she would have a longer and more frustrating ride. A few minutes later Tina was moaning again.

"Oooohhhh, yes, faster please, I'm soooo close, I need to cum, more, more, faster."

Colin grinned as he slowed the machine down slightly, causing Tina to give a mournful groan as she realized that she would have an even longer period of frustration. I heard a scream and turned in time to see Troy giving a final thrust into Georgia as she writhed in ecstasy on the swing. It was clear Troy was filling her with his cum, then I turned back to watch Tina begin to shake, holding onto the front of the machine as her body writhed in her first Sybian orgasm. After a few moments for recovery, she sat back and squeezed her nipples hard as Colin sped the machine up to almost full speed, causing Tina to emit several short, sharp shrieks as her hips moved back and forth rapidly, seeking more stimulation as her body was racked with another, even more intense orgasm.

In a few moments it was all over. Georgia lay passive on the swing, Tina sat slumped over the front of the Sybian. Troy unfastened Georgia and I stepped forward and unfastened her knees then helped Tina stand up, the dildo sliding from her gushing pussy. We hugged and kissed, my cock responding slightly despite its recent orgasm. We gathered around Sylvia.

"How's everyone?" she asked.

We all agreed we were fine, exhausted, cummed out.

"Great, that's what this place is for. One final thing, are you ladies sure you don't want a few strokes of the cane on your asses before you leave?"

The four women looked at each other. Georgia and Beth seemed a little reluctant so Sue and Tina reassured them that it wouldn't be a real caning, just a couple of gentle strokes each. They looked doubtfully at Sylvia as she held a short cane in her hand, and after seeing her nod, agreeing with Sue and Tina, they finally agreed, so long as they didn't have to go first.

"What about the guys?" asked Tina.

It was something I hadn't experienced and hadn't considered, until now. I was not too concerned, trusting Sylvia to know what she was doing and feeling reasonably certain that she would do no permanent harm. Then Terry replied, making my thoughts superfluous.

"We'll have one stroke each," he replied, looking around to judge our responses; I noticed that we were all nodding in agreement. "And I'm happy to go first."

Sylvia grinned and nodded, accepting Terry's compromise. Terry stepped forward and bent over the padded caning bench indicated by Sylvia. She tapped his shoulders and he lowered them, relaxing more, then she struck a sharp stroke across his ass cheeks. He bore it silently, then stood up.

"There, that wasn't bad, was it?" asked Sylvia.

"No, that was Ok," he agreed, rubbing his ass, "Just stung a little." He turned his back to Georgia. "How's it look?"

"Yeah, a single red line, no skin broken, doesn't really look sore at all," she replied, "Maybe you need to get a few more."

"Yeah, that's fine, so long as I can cane you too," he replied with a grin.

"I'll see about that after I receive mine. After all, we do have next week as well."

Each of the guys in turn bent over the bench to receive their stroke, rubbed away the sting and then grinned at the thought of our lovely ladies receiving a few more than we had, how many we did not know. Georgia decided to go first.

She walked to the bench, bent over it, waiting for Sylvia. First stroke, a sharp "Ow" from Georgia, and she reflexively stood up, rubbing her ass with her hand before grinning.

"Yeah, not bad at all."

Sylvia patiently tapped her shoulders and she gulped, then bent over again.

"After each stroke, stay in position," commanded Sylvia, handing two dice to Terry. "Throw them so I know how many more to give."

He threw the dice, a 4 and a 5, 9 total.

"You will receive a further eight strokes," announced Sylvia.

Sylvia used moderate strokes, waiting about 15 seconds between strokes to allow Georgia to fully feel the effects of the previous stroke. After the ninth stroke, Sylvia offered her hand to Georgia to help her straighten up. Georgia rubbed her ass, trying to reduce the stinging. I noticed that her nipples were engorged and standing out from her breasts, indicating her arousal. She returned to stand in front of Terry, leaning back against him and placing his hands on her breasts as she rubbed her ass against his semi-hard cock. Meanwhile, Beth bent over the caning bench and Sylvia applied a stroke across her ass, causing her to give a sharp yelp, before relaxing again, waiting for Colin to throw the dice. He threw a total of 7.

"Another six to go," Sylvia announced to Beth.

Again, Sylvia applied the six strokes, again as Beth stood afterwards, she showed clear signs of arousal as she walked over to Colin. I noticed that Terry had his arms around Georgia, his fingers between her legs. Tina was up next and I threw two threes, then watched as she received her six strokes. When she returned to me, she seemed very amorous, pressing her body against me and kissing me sexily as I gently massaged her hot ass cheeks. Finally, Sue took her place and, as luck would have it, Troy threw double six. Sue groaned when it was announced, then took the additional 11 strokes after her first, spending a while after she stood as she rubbed her ass, before walking over to Troy and pressing herself against him.

"I need to fuck," she told him, loudly enough for me to hear from alongside her.

"I'm sure you have several willing volunteers here," he replied with a grin.

Sylvia thanked us for coming today and hoped she'd see us again soon. We also thanked her, then left, heading to a spa pool. We all piled into the pool, swapped partners, then the guys sat on the underwater benches, water up to our armpits, and the ladies straddled our thighs facing us, Beth choosing me.

"I'm so horny, darling, please fuck me," whispered Beth in my ear.

I could feel my cock hardening. After watching four nubile naked young women cum and be caned over the past hour, I was unsurprised. She wriggled on me, positioning herself then, when everything lined up, she sat downwards and I slid into her effortlessly. She put her head on my shoulder, pressed her body against me, and relaxed there. As each couple connected, normal conversation resumed slowly. It was a strange feeling being with a group of people, knowing that each woman was riding the cock of a guy who was not her usual partner, yet continuing normal conversation as though nothing unusual was happening. I guess, by Pleasure Island standards, this was quite usual and nothing unusual was happening.

Over the course of the next hour or so, everyone came at least once. Sue came several times and I noticed that Tina also seemed to reach at least two major climaxes. I gave Beth another injection of sperm but I'm almost certain she came more than once judging by the pulsing of her cunt around my cock. As the sun set, we all finally parted, agreeing to meet up in the dining room for dinner.

After we'd eaten, we danced for a while, sipping cocktails before finally heading to bed for the last time with Colin and Beth. Beth and I watched as Colin and Tina fucked up a storm, Colin bringing Tina to two screaming orgasms before he finally came deep inside her. Then it was our turn, and for a start Beth rode me, her hips moving back and forth quickly as she ground her clit against me. I had no doubt that I would have cum early if I wasn't almost completely cummed out from the afternoon activities. Once she'd cum, she rolled onto her back, spread her legs wide and beckoned me to her.