Pleasure Island Ch. 03

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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.


Betsy led us into a different wing, knocked on the door, then introduced us to Jacqui and Becks. They invited us in and poured us drinks as we sat on the deck in the sun.

“I’ve briefed Jeff and Tina on their mission this week,” said Betsy, once we were all settled, “And they’re very willing to do all they can to ensure you’re both pregnant when you leave. Actually, Jeff’s spent the past week trying to impregnate another client, so I guess he’s had lots of practice.”

“Sounds like you’ve got a good job,” commented Jacqui, a tall blonde with a beautifully curvaceous figure, “I hope you saved some for us.”

“I’m sure there’s plenty more,” I told her, looking forward to having her alone to myself.

“Mmm, and for me, I hope,” added Becks, a shorter woman with dark hair and a slighter build. “What do you think of your partner knocking up all these women?” she asked Tina.

“Fine by me. My only stipulation is that I’m involved as well; we’re a couple and we’re very pleased that you’re happy for us both to be here with you.”

“Cool,” replied Becks, “So you’re into women as well as men? Would you class yourself as bi?”

“Not really, I guess, my experience with women is limited, but let’s say I’m an eager learner,” she replied with a grin.

“Sounds like it’ll be a fun week,” commented Jacqui, “Thanks very much for finding these two, Betsy. We’ll let you know how things go during the week.” She stopped, as though suddenly thinking of something. “You are fertile,” she asked, looking directly at me, “You’re not shooting blanks like the last guy, right?”

“Not as far as I know,” I replied, “Although I don’t have any track record in the breeding stakes. Most women seem to want to ensure they don’t get pregnant rather than try to become pregnant. I must say that so far it’s been a pleasant change.”

“Right, so it seems you guys are all good. I have work to do so if you’ll excuse me, I’ll be going. Have a fun week and if there are any problems, I’m just a call away.” Betsy stood and walked away as we thanked her for her help.

Once Betsy had left, Jacqui and Becks moved apart on the sofa and patted the seat between them, grinning at me. I took the hint and sat in the vacant space. Immediately both women were stroking and caressing me as they quickly stripped off my shirt and shorts, leaving me naked between them with an almost hard cock. They applied themselves to rectifying this and within a few moments I was hard and horny.

“You go first,” Becks told Jacqui, then turned to me and explained that she was further through her cycle so it was more urgent that I impregnate her as soon as possible.

Jacqui wasted no time in straddling my thighs, her short skirt riding up to reveal she was wearing nothing underneath. I reached under her elasticized top and lifted it off her, taking it over her head and exposing an impressive set of beautifully proportioned breasts with hard protruding nipples. She placed my hands on them and whispered into my ear, “Torture them, hard, darling.”

I did just that, squeezing her nipples hard, expecting her to cry out in pain. Instead, she closed her eyes, tilted her head back and let out a moan of arousal. Becks had been watching and I saw her out of the corner of my eye, grinning. She caught my gaze.

“She’s a complete pain slut,” she told me, “Loves pain, gets off on pain, enjoys pain more than sex, although when they’re combined, she’s in heaven.”

I took that as a cue and bent my head forward, biting a nipple quite hard. Instead of the scream and slap I half expected, she moaned deeply. “Oh, yessss, darling, oh yessssss.” She wriggled forwards on my lap until her bare pussy was pressed against my rigid cock. She lifted herself up, allowed my cock to slip between her thighs, then wriggled until it was at her opening. She grinned at me and nestled her head into my neck as she lowered herself onto me. The feeling of my erect cock slowly penetrating her silky love tunnel was amazing. Once she was right down and relaxed, I could feel her cunt clamping and releasing as her muscles contracted and relaxed.

“Ooohhh, that’s so nice,” I murmured in her ear, “Are you doing that or is it reflex?”

“That’s reflex,” she replied, “My muscles are just contracting by themselves. They must like you,” she said, leaning back slightly and grinning.

I noticed that Becks was no longer beside us and saw she was slowly introducing Tina to lesbian sex. Both women were naked on eryaman genç escort bayanlar the large, soft mat on the floor, kissing and caressing each other as they pressed a thigh against the other’s pussy, two sets of hard nipples indicating their arousal. Jacqui followed my gaze and whispered in my ear, “Becks will train Tina really well, just as she trained me. If she wasn’t bi before this, she sure will be by the end of the week. Now fuck me hard, squirt your hot, fertile cum in me, make a baby in me.”

She grasped my hips in her hands and began pulling and pushing, sliding herself back and forth along my thighs, pulling herself almost completely off my cock before plunging it deeper inside her. I could feel her hard clit sliding along the upper surface, watching her face take on a vacant stare as the sensations took over from any conscious thought. She grunted each time I was fully inside her, a regular, deep grunt as she tried to take even more inside her.

“You want more?” I asked.

“Yes, honey, give me all you’ve got.”

Next time she moved away, I pushed her off my knees, stood up and positioned her over the arm of the sofa, bent so her head rested on the cushions. I kneed her legs further apart then stroked her gaping trench a few times while she moaned with lust.

“Oh, push him in,” she begged, “Fill me up, darling.”

I held her hips and slowly pushed my swollen cock inside her sloppy cunt, further, further, feeling the head hit the end, but I pushed harder, feeling it press against the hard lump of her cervix.

“Yes, darling, like that, yessss, press harder against the end. Ooooohhhh, yes, it hurts so good.”

I knew that many women found it painful if I hit the cervix, but it seemed Jacqui enjoyed it; but then I remembered, she was a self-confessed pain slut. While continuing to press against her cervix, I reached around her and grasped her hanging nipples, squeezing them hard, pulling them away from her body. I was rewarded with another deep heart-felt moan of mixed pain and pleasure. I made a note to take her to the dungeon this week – often. While still holding her nipples, I began plunging in and out, fucking her hard as her moans increased. I felt my balls slapping against her clit with each thrust as she forced herself back against me, seeking more pressure and more depth. Her moans turned to cries of pleasure, which quickly became shrieks as we both climbed the slope towards our releases. I held back slightly, waiting for her, then I felt her go rigid beneath me, her breath held back, I thrust in again twice, quickly, hard, then I began spurting my hot cum against her cervix while she let out an immense shriek as her body began convulsing beneath me. I held her nipples hard, pressed my cock into her as far as possible, and held on for dear life as her body threatened to throw me onto the floor.

It was over in a short time. Jacqui’s body slowly relaxed, her shuddering stopping, and I was also able to relax. I noticed both Becks and Tina were watching us as they lay on the mat in a 69 position. After a few minutes I leant back pulling my softening cock out of its tunnel.

“Put in a ball,” said Becks, “On the counter. It’ll hold your sperm inside.”

I took one of the balls on the counter, noticing they were close to two inches diameter, then pressed it against Jacqui’s open entrance. I was surprised how easily it slid inside. Becks must have noticed the surprised look on my face as she grinned at me. “We often use them in our pussies, play lots of sexy games with them,” she explained.

Once Jacqui was plugged, she seemed to come back to life, slowly straightening, standing up, then she turned to me and we embraced.

“Jeez, you’re a fuckin’ good lover,” she said as we held each other, then kissed for a long time, “For a man, anyway,” she completed, grinning at Becks.

We wiped ourselves and remained naked, sitting on towels on the sofa as we watched our partners make love on the mat, each bringing the other to what looked to be a very satisfying orgasm. Once they recovered and wiped off, Becks suggested a swim. “You’ll be Ok with that ball in you. Probably help you to float,” she commented to Jacqui with a grin.

The pool felt cool and refreshing. We were pleased with the clothing optional rules because we could simply walk to the pool, swim, then sunbathe naked. We chatted idly as we dried in the sunshine, Becks stroking my cock as though it was her new toy.

“Hope you can get him up again today,” she said, “I’ll be very disappointed if Jacqui’s worn him out.”

“He’ll be fine,” said Tina, “He routinely manages four or sometimes even five a day, but not with me while we’ve been here, he’s been far too busy impregnating others.”

“So, when’re you having kids?” asked Jacqui.

“We haven’t discussed that,” replied Tina, “Don’t even know if we’ll have any. No plans yet anyway.”

“Well, I guess it’s great that Jeff can practise on others first. How do you feel about Jeff fucking other women?”

“No problems. ankara escort bayan We have an open relationship; we both have other partners. It’s only sex, it’s not like we form a true loving relationship with someone else; just a bit of fun. Besides, most of the time we’re with another couple or more and can watch each other enjoy themselves.”

“So, you don’t feel jealous or anything?” asked Becks, propping herself up on her elbow to better watch our faces as we responded.

“No, nothing like that, do we, honey?”

“Definitely not,” I replied. “We love each other; we feel comfortable in the knowledge that no matter who we each make love with, we will each be the only true love of the other. If we love each other like that, we want the best for each other, and if that best includes the ability to experience passionate sex with someone else, who are we to stop the other from having that experience? I never cease to be amazed reading about couples who break up a perfectly good marriage or relationship simply because one partner or the other strays, as they put it politely, or, to put it more bluntly, enjoys wild passionate sex with someone other than their partner. It’s all this puritanical bullshit that really annoys us. Anyway, I’ve ranted enough.”

“No, I totally see your points and admire that you’re able to retain your freedom while remaining in a committed partnership. Do you think you’ll ever become poly and open your relationship to someone else on a longer term?”

Tina and I exchanged a glance, then I nodded to Tina to answer. “Possibly, if we found the right person or couple to share with. But any relationship we did have like that would be along the same lines as our own. In a marriage, the main problem is that people vow to be true to each other, etc. People change. We have the option to leave each other at any time; every morning we wake up and choose to spend today together. We could split at any time, but we don’t, and it is this ability to choose which ironically is what keeps us together. We have freedom to choose, something which those in normal marriages have surrendered, which can cause them to feel trapped, and when you feel trapped, you want to leave. Many find the usual is boring while the unknown is attractive. We can have both the usual and the unknown.”

I leant down and gave Tina a kiss. “You put it so well, darling, as usual.”

“Anyway, I feel like I’m getting a bit burnt and I certainly don’t want that,” said Jacqui jumping to her feet, checking between her legs to ensure the ball was still in place. “Let’s have something to eat then decide what to do next.”

We strolled back to the cabin and ate a few snacks while drinking some wine. We chatted about sex and then the subject went round to the use of pain to enhance sexual pleasure. Jacqui commented that she really enjoyed pain in a sexual context, while Becks confessed she wasn’t really into pain, but enjoyed inflicting it.

“You see, we’re made for each other,” she joked with Jacqui.

“Have you been to the dungeon yet?” I asked.

“No,” replied Becks, “We heard about it but we were so focused on being impregnated last week that we never got around to it. Is it fun?”

“That depends on what you call fun,” replied Tina. “I like it gentle, and Jeff doesn’t like to hurt me, so we did a few things last week but nothing I’d call excessive.”

“So, like, you got caned on your clit and had your nipples pierced with needles and stuff like that?” asked Jacqui.

“Absolutely not! That would be far too painful for me,” exclaimed Tina. “Just a few light taps on the ass really. Stung at the time but was fine the next day.”

Jacqui looked disappointed. “Well, I guess we could check it out. Becks might like to get carried away and beat me to a pulp,” she grinned.

“What we did try was the Sybian. Have you used one?” asked Tina.

“Heard of them, watched women cum on them online, wished I had one, but no, never seen one in the flesh. Let’s do that now. Is it possible?” asked Jacqui.

“I’ll check,” I replied, “Anyway, have you still got that ball in your cunt holding in my sperm?”

“Yes, honey, could you take it out for me please? If it hasn’t found its way by now it never will.”

Jacqui moved to the sofa beside me and spread her legs wide apart, showing me her pussy lips held slightly open by the ball inside. “Can you push it out?” I asked.

Jacqui tried, her lips parting a little more so I could clearly see the ball inside. It was obviously going to need some help. “Looks like you’ll have to operate to remove it, doctor,” Jacqui laughed, “Push your fingers in around it and pull it out.”

“It could hurt you,” I replied, afraid to damage her beautiful pussy.

“Hey, remember, I get off on pain. Besides, babies come out of that hole. Just do it, please lover.”

I moved to her and sat between her legs, then used my thumbs to pull her labia apart, showing more of the ball. “You really should try a smaller ball,” I said, “Or at least etimesgut escort have a string on it.”

“What? And take away all of our fun?”

“I use a smaller ball with a string attached,” said Becks, “But I need to wear a harness to hold it inside me. I really enjoy harnesses like that.”

“Ok, here goes,” I said, pulling her lips apart as far as I could with my thumbs then pressing my fingers against the junction between ball and labia. The labia lifted slightly and I was able to ease a finger into her and push it as gently as possible inside, holding it tightly against the ball so as not to stretch her opening too much. I looked at her face, expecting to see a grimace of pain, but instead she had a smile and a look of utter enjoyment.

“You like me doing this?” I asked.

“Yes, darling, it feels so wonderfully, painfully sexy. It’d be so good if you put your whole hand in and fisted me properly. Maybe when the ball’s out you can do that, while I’m still stretched?”

At the thought of fisting her sweet pussy I felt my cock lurch and begin to harden. Becks noticed. “He’s getting hard,” she told everyone, “Looks like he wants to fist you, Jacqui.”

“Ooohh, goody,” she said, “So put some more fingers in me to stretch me further, darling.”

I looked towards Tina to see how she was taking this. She was smiling querulously, possibly wondering where this was going, possibly wondering if I’d be wanting to fist her also, possibly wondering if she’d allow me. I gave her a wink and then focused on what I was doing. I could just get my fingers behind the ball and began pulling outwards, watching her labia bulge and spread even more until with a sudden pop, the ball flew out and landed on the floor, leaving my fingers inside her wide-open entrance. Becks handed me a jar of lube. “Here, I’ll rub this over your hand; it’ll make it easier for you both.”

She spread a generous amount of lube over my hand as I turned it and moved it so she could have better access, then I squeezed my fingers together and pushed all my fingers inside as far as I could.

“How’s that feel?” I asked Jacqui.

“Great, honey, but I want your whole hand as a fist.”

I pulled out a little, placed my thumb against my palm, then pushed gently inside, feeling her lubed lips slide over the back of my hand and along my thumb as my fingers opened and explored her innermost depths. Then my fingertips pressed against the end of her tunnel and my hand stopped.

“Make a fist, darling, then you can go inside further. It feels so great, but I want more.”

I gently made a fist, feeling her muscular cunt expanding around my hand, then I pushed in further, her labia stretching over my knuckles then contracting slightly around my wrist. I noticed that Jacqui seemed to pull upwards with her muscles and I felt her cunt expand to allow me to go deeper until my knuckles pressed against the end.

“I feel so full,” she moaned, a broad grin on her face as she moved her hips gently so my hand would massage her from the inside. “Your fist’s bigger than Becks’. Just fuck me with your fist for a bit, darling.”

I did, gently turning my fist and moving in and out as I felt her muscles gripping and releasing me. She turned her head towards Becks. “Get the Hitachi,” she said, “I wanna cum.”

Becks retrieved the vibrator from the drawer and sat on the edge of the sofa, then placed the vibrator on Jacqui’s clit and turned it to medium. I immediately felt Jacqui’s cunt convulse as the sensations pulsed through her pussy, her head began turning from side to side and she gently moaned in pleasure. It took only a few moments it seemed before she let out a scream, her body shuddered then thrashed about, and her cunt clenched my fist tightly as she came hard.

Becks removed the vibe and gradually Jacqui’s breathing slowed as I eased my hand from her sopping love tunnel. She opened her eyes at last and grinned up at us.

“That was amazing,” she said, “Absolutely amazing. Every woman should have that experience. Thank you, darlings.”

We spent the remainder of the afternoon relaxing, swimming, sipping cocktails and enjoying the beautiful location. I took time to visit Sylvia and book a Dungeon session for tomorrow afternoon, then, after watching the sunset, we ate dinner together and retired to bed relatively early.

“Have you ever used a strap-on?” Jacqui asked Tina.

“No, never. Haven’t had much need with Jeff always nearby.”

“Well, tonight’s the night when you lose your strap-on virginity. Becks, it’s probably time you received a dose of potent sperm if you’re wanting to get pregnant, which leaves Tina and me to explore the wonders of the strap-on.”

While Becks accepted Jacqui’s suggestion and snuggled closer to me, Jacqui pulled a couple of dildos with a tangle of straps from a drawer and walked around the bed to Tina. “I’ll put it on first,” she said, “So you know what to do. It’s quite simple really. I’ve got two sorts here, one that just straps onto my crotch and has a pad that presses against my clit to give me some sensations too, while the other is double ended, one end fitting into my cunt while I push the other end into yours. That gives us both lots of arousal. Key thing is lubrication, especial to start, once we start producing our own it’s not so bad.”

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