Paradise Island

by: Nurture Nature

Chapter Index

Chapter 7



Week 1 Day 3



John - American-Caucasian, 34 years old, married, father of 2
Alec - American-Caucasian, 51 years old, divorced, father of 3
Pamela - Brazilian, 17 years old, assistant, 5'-5", brown hair, Stage 4
Trista - French, brunette, 11 years old, Stage 2
Alissa - Ukraine, dirty-blonde, 10 years old, Stage 1



John heard a knock at his door...

"Come in."

"Hey, John, everything alright?"

"I don't know. This isn't right."

"I thought you had a hell of a great time this morning. I was serious when I told you that was the hottest fuck I've ever seen."

"Alec. I have a wife and kids. What am I doing here?"

"It's your first time. Of course you're going to have reservations. It gets easier."

"Do you understand? I have a daughter."

"I have one too, John. And 2 sons."

"They're grown. Mine aren't. I can't even imagine if something like that ever happened to them."

"Look. Yours are being raised the way you and Joyce want them to be raised. But, so are the ones here. It's just a different lifestyle."

"Lifestyle? This is a business, Alec, and you know that."

"Exactly. It's a business, just like our own businesses back home. Don't get all worked up because of back-home societal pressure."

"I can't believe Pamela allowed that to happen. She even helped!"

"Pamela is their trainer. Of course she's going to help."

John thought on that for a moment.

"Look, John, you knew this was a fuck trip. You lucked out. This is the hardest core experience anyone can possibly have. Tonight, just try to remember how hot that little thing looked in that g-string. And let me tell you, it gets even better."

"How so?"

"Don't worry about it right now. Just let things happen, it'll all present itself."

"Well, I'm going to hit the sack. It's been a long day."

"Yeah. I think I'm going to turn in early too. See you at breakfast."


The following morning just before breakfast concluded...

"Good morning, gentlemen!"

"Hi, Pamela!"

"Have you enjoyed yesterday, Darrel?"

"Oh yes, very much!"

"And you, John?" Pamela winked.

"Ah... yeah." John politely responded.

"That is good! Gentlemen, I offer this morning. Of course our place provide everything in the imagination. So today you may visit the object room and you may choose!"

"Object room?"

"Ah, yes, Juan! Anything, such as the nipple clamps, the bondage, anything at all! And then Nina provide!"

"Sounds great!" Darrel exclaimed.

"Count me in."

"Of course, Alec!" Pamela chuckled.

Then men entered the object room...

"Wow. Get a load of this." Darrel looked all around the room. "I've never seen so much stuff."

"John, can I make another suggestion?" Alec offered.

John didn't respond.

"Check this rack out. It's fully adjustable. You can put her into any position without help from anybody." Alec explained as he moved the arm and leg bars into various positions. "It's fully rotatable, she can be suspended in the air at any height, allowing you unrestricted access to any part of her body. It's actually my favorite device."

"This is hard-core." John said under his breath.

"Yeah. Hey, if you want, I don't mind sharing the room with you again. I can show you a few things that took me a while to figure out." Alec offered.

John thought for a minute. He really did like the functionality of the rack, but would never have considered it without Alec's help.

"I guess."

"Great. While we're at it, let's reserve some nipple clamps. I'll pick some other things out."

After John and Alec were finished reserving the items, Alec pulled Pamela to the side.

"Pamela, I spoke to John. I'm wondering, if it's not too much trouble, for us to share a room again later this morning?"

"Alec, that is 2 times! However, for you, I provide. Please remember no touch the other selection!" Pamela smiled.

"Thanks, Pamela. Yes, I understand. The afternoon session we'll each take our own separate rooms."

"You make reserve?"

"Yes, everything is picked out."

"John, I spoke with Pamela, it's all set."

"Ok. Hey, listen, I'm going to rest up a little. How about if I just meet you there?"

"Sure thing. Don't forget to turn the blue light off to let them know you're on your way. Otherwise they'll send a search party out looking for you." Alec chuckled.

About an hour had passed while John was in his room waiting for the blue light to turn on. He was still having second thoughts. John tried to forget about things until it was time, but being alone made it a challenge. Finally, the blue light came on startling him. He gazed at it, still contemplating, but then decided that since Alec was meeting him there, he would go. John turned the blue light off and then closed the door behind him. He arrived at Room #3 where Alec was already waiting.

Alec took his robe off and hung it on the hook. John did the same. John opened the door and entered first with Alec right behind. Alissa and Trista were both in the room, wearing their chosen outfits.

John noticed that the pink g-string was the same identical one she had on before, only now it hung looser on her due to John pulling and stretching at the strings yesterday.

"John, be a little more assertive today."

John looked at Alissa and the rack behind her, and then took several deep breaths.

"Have you done this before?" John inquired nervously?

"Pamela teached us."

"Teached you?"

"Pamela teached in training how to get in."

"With... other men, or boys?

"No. Just to get in."

John trembled. "Can you... secure yourself in?"

Alissa leaned her back against the padded bar. She raised one leg, placed her foot on the foot peg and hoisted herself up. She then raised her other leg, placed that foot on the other peg, and then closed each bracket over her ankles. Alissa rested her head against the padded portion of the device. She swung another bracket over her neck and locked it into place.

John saw that she was unable to secure the brackets around her wrists so he assisted with those. Once done, John moved the appendages around to test mobility. He decided that he wanted her spread eagle so he moved the appendages accordingly. Alissa's body looked incredible in that position as it fully exposed her, not only from a frontal view, but from the back as well. John re-positioned the device so that Alissa lay horizontally with her back to the floor.

Alec suggested to John to pull an auxiliary bar over Alissa, about a foot above her chest. John did so and locked that into place.

"Put the gag in her mouth."

John followed Alec's instructions.

"Grab that pair of nipple clamps. Throw them over the bar and attach them to her nipples."

"I don't think it'll work." John said.

"What do you mean?"

"Come on, Alec. She doesn't have anything. Her nipples are tiny."

"They'll go on. Just pull on the nips and attach them.

John managed to attach a clamp to one of the nipples, but there was not enough chain to for the other clamp to reach the other one.

"Lower the bar closer to her."

John did. But when he attached the clamp to the other nipple, the first one slid off.

"Tighten the screw." Alec told him. "Tug on it to make sure, and then give it an extra turn."

Alissa whimpered and winced her eyes as John tightened the screw another revolution. John proceeded to the other nipple and attached the clamp the same way.

"Ok, now slowly raise the bar."

"What?"

"Go ahead." Alec confirmed.

John slowly turned the knob, raising the bar, bringing Alissa's nipples up with it. She didn't have any breasts so about an inch was all that rose.

"Wait, lower it back down." Alec said. "That one clamp is starting to slip off again."

John lowered the bar again and reattached the failing clamp. After it was secure, he turned both knobs another full revolution.

"They shouldn't come off now." John confirmed.

Alec was becoming impatient so he walked over to Alissa and turned the knobs an extra full revolution.

"They won't now." Alec assured as Alissa whimpered loudly.

John slowly raised the bar once again, creating one inch tee-pees.

"A little more." Alec told John again."

"It's pretty snug."

Alissa whimpered louder.

"Raise it a little more." Alec said, preoccupied with Trista.

John turned the crank again and slowly raised the bar. The skin in front of Alissa's arm pits stretched as her nipples rose higher. Alissa whimpered louder yet. John stopped when he felt the bar would not rise any higher, not wanting to tear her delicate beige nipples.

Alec turned his attention from Trista to John and Asissa again. "Whoa. I didn't realize you raised it that much. Touch lightly and see if there's any play in her skin."

"No, none at all. I'm going to lower it about a quarter of an inch."

"No... just leave it. It's already in place. Rotate the rack over so that she's facing the floor."

John spun the device over. The bar over her chest remained in position.

Alissa's legs were still spread eagle as were her arms.

"Go ahead and lube your cock." Alec instructed.

Lubing his cock generously, John stared at Alissa's slit.

"Now, squirt some lube into her asshole."

"Alec, no."

"You worry too much. Just do it."

John became nervous again, staring at Alissa's ass.

"Don't forget to put this on." Alec handed John the vibrating cock sleeve. "Especially for that little ass."

John convinced himself that he would be gentle, and that Alec was probably right - some women actually do enjoy anal sex, and they all start somewhere.

John stood behind Alissa holding his rock hard boner. He caressed her smooth, dimpled back just above her ass, along her sides down to her protruding hip-bones, and then placed each hand on each of her spread, beautiful ass cheeks. John spread her ass cheecks further apart to see if the lightly colored rose-bud would slightly gape, but, it didn't.

"Trista, go over and help out." Alec instructed. "Pull her ass cheeks apart and don't let go."

John positioned his cock head against Alissa's beautiful rose-bud. He pushed a few times but met with resistance. Trista was doing a good job of spreading them apart so it wasn't a problem on her end. John inserted his middle finger into the well-greased hole to loosen Alissa up.

John pressed against the rose-bud again using more force, causing his cock to slip and almost penetrate her pussy. He gained better footing, this time holding his cock with a hand. He pushed in again keeping perfect aim, until his cock head entered her sphincter.

Shackled in, along with her nipples being stretched, Alissa didn't move an inch. She let out a yelp, but the gag muffled most of it.

John pushed his cock in another inch, and while at that depth he picked up the tube of lube and squirted more along the exposed part of his shaft. He pulled slightly out, and then used his hand to evenly distribute the lube. John pushed in again. Alissa's asshole was tight indeed.

Meanwhile, Alec was enjoying watching this almost as much as doing it himself. He would use John and Alissa to provide him with visuals that would lead to his own arousal with Trista.

John pushed deeper inside while Trista continued holding Alissa's ass cheeks wide apart. Now, he was about half way in.

"John, she has limits. Don't go any more than three quarters." Alec instructed. "Go ahead and fuck it, but don't cum inside."

John picked up speed. Not intending to hurt Alissa, he had no problem using her asshole to provide pleasure to his cock. John's cock was now thrusting rapidly in and out. Trista maintained her grip pulling both of Alissa's cheeks apart. Alissa continued to yelp but the noises were muffled by the gag.

John sensed his cock leaking pre-cum inside of Alissa's asshole. He knew that it would be less than a minute before his cock would explode. He slowed his rhythm, savoring and memorizing the sensation, and then extracted.

"Go ahead and detach her now." Alec said.

Trista let go of Alissa's cheeks. John turned Alissa over so that he could gain access to her front. He released the lever and slowly lowered the bar, giving slack to the nipple clamps that forced her nipples into tee-pees.

John removed the clamps from Alissa's tiny buds which were now flattened out like a piece of paper. He was surprised to see that they did not spring completely back to their flattened state, but instead protruded slightly from her ribbed chest. John removed the brackets from Alissa's neck, wrists and then her feet, took the gag out of her mouth and then helped her climb down off of the rack.

"John, hand that to Alissa. Have her get into doggy on the floor mat."



John repeated the instructions to Alissa.

Alissa took the device from John and positioned herself into doggy. She reached one hand around to her beautiful, firm bottom and slowly pushed the 4-1/2 inch vibrator inside of her ass, leaving the attached string dangling off to the side of her slit.

"John, use the baby-wipe to clean the lube off of your cock and kneel down behind Alissa."

Now on his knees, John placed both of his hands on Alissa's firm, round bottom and caressed it. He was still intrigued with the dimples on each side of the small of her back and moved his fingers to that area. He grabbed Alissa by her protruding hip bones and positioned his cock.

"Not yet." Alec interrupted. "Stimulate her clit. Get her cunt soaking wet."

Alissa was still on her knees in doggy. John pushed Alissa's head down to the floor, then reached under her abdomen and lifted her ass up toward the ceiling. He couldn't believe how light the girl was as he hoisted and positioned the little rag doll. John spread Alissa's legs further apart to gain better access and rubbed her clit with his saliva covered fingers. Soon enough Alissa's vagina leaked more natural lubrication.

"Push it deeper into her ass."

Alissa grunted when she felt the device penetrate her deeper. John and Alec noticed that her ass tried to expel the device.

"Hello everybody!" Pamela entered the room.

"Oh, hi Pamela! I didn't know that you were coming today?" Alec greeted with a smile.

"I come to do the vibrating sleeve. Each day John go deeper, yes?"

"It actually worked out well when he fucked her ass."

"Ah, very good! He is ready for vaginal now?"

"Yeah." Alec said.

Pamela used a pair of scissors to cut the sleeve making it half an inch shorter.

"Tomorrow I do again." Pamela handed the sleeve back to John.

"Do you want to stick around and watch?"

"Yes of course! Thank you Alec!"

"John, it expelled a little. Push it back it in and hold it in with your finger. You'll feel a little switch on the end of it."

"Oh my, a vibrator in her ass as well?" Pamela smiled.

Inserting his middle finger into Alissa's ass, John located the switch. Upon flicking it, Alissa jolted, feeling the device rattle her rectum. John rested his hand on the small of her back and used his thumb of the same hand to keep the vibrator pushed inside.

John then turned the vibrating cock sleeve on and pressed his cock head against Alissa's dripping slit. With one single motion he sunk his shaft halfway into her vagina. The vibration around his throbbing cock was indescribable. He withdrew and sunk halfway in again, coating his shaft with Alissa's vaginal juices. John penetrated deeper yet into the slick, tight vagina, feeling intensity around his entire cock as both the vibrator and John's cock rattled Alissa's innards.

Both John and Alissa noticed the difference half an inch made as his cock sunk in deeper. Alissa breathed heavily, shaking her head side to side, trying to move forward and away from John. But Alec was in front of Alissa and stopped her from disengaging. One thing Alissa and John had in common was that neither of them had ever done anything like this before.

As stimulated as Alissa was, she was not going to be able to endure much longer. Likewise, John wasn't going to be able to hold back much longer, feeling his cum begin to boil.

"Ohhhhh... ohhhhhhh!" John breathed heavily, arching and hunching his back.

John maintained holding the vibrator in place using his thumb. His other free hand, however, shifted back and forth from grabbing Alissa by her hip bone, to squeezing and spreading her beautiful ass cheek. Alissa's body was John's playground, one that he enjoyed more than anything he could remember.

Alec noticed a few drops running down the side of Alissa's face. Grunting, Alissa maintained doggy position, shifting her knees from time to time in order to keep herself balanced.

Alissa's breaths became shorter and quicker. Instinctively, she steadied one hand to the ground and reached the other between her legs.

"Cum... together..." John whispered

Alissa nodded yes.

"Alissa, feel that shaft using your cunt. He's going to fill you with semen. Is that what you want him to do?"

Alissa breathed heavily and nodded yes.

"Feel those vibrations. Spray that semen deep inside of that unprotected cunt."

John was less than 15 seconds from unloading. Alissa made a pause sign with the palm of her hand between her legs, but then moved it to her abdomen and lightly pressed against it.

"Ohhhhhhhhh!" Ohhhhhhhhh!" John groaned.

"Hu...hu...hu... Ohhhh!... Hu...hu... Ohhhhh!" Alissa let out a very high-pitched squeel at exactly the same time.

John filled her canal with rope after rope of thick semen. Alissa felt the lake being pumped deep inside of her.

Immediately after both had climaxed, Trista knew that John and Alissa would be in no condition to deal with the vibrator still lodged in Alissa's ass. So she quickly went over, shoved her finger into Alissa and turned it off.

John's cock limped slightly, though it was still blood-filled enough to post-fuck a little longer. Alissa's cunt was fully loaded with jizz, but a good amount of semen ran down both of her skinny legs. Alissa stayed on her knees while John caressed his limping cock inside of her vagina. At times she rocked back forth, indicating that she was enjoying it too.

"Tomorrow I cut half an inch again." Pamela told John as she stroked Alissa's hair.

"You two sticking around to watch?" Alec asked.

"Sure." John replied.

Once John and Alissa finished up they moved to Alec's side of the room. John took a seat Indian-style on the floor mat. He felt comfortable enough with Alissa to sit her down between his legs and wrapped his arms around her holding her from behind. Alissa leaned back into John's chest to watch the show. Within moments, Alissa's cunt began leaking semen which John felt pooling by his crossed feet.

"Are you ok?" John whispered into Alissa's ear.

"Yes." Alissa replied softly.



Chapter 8



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