Paradise Island

by: Nurture Nature

Chapter Index

Chapter 8



Week 1 Day 5



John - American-Caucasian, 34 years old, married, father of 2
Alec - American-Caucasian, 51 years old, divorced, father of 3
Sergio - Russian, 45 years old, manager
Pamela - Brazilian, 17 years old, assistant, 5'-5", brown hair, Stage 4
Darrel - African, 58 years old, divorced, father of 2
Juan - Puerto-Rican, 40 years old, single
Trista - French, brunette, 11 years old, Stage 2
Alissa - Ukraine, dirty-blonde, 10 years old, Stage 1


Pamela suggested to everybody to take a break this morning, though it wasn't mandatory. The guys agreed, and because it was another beautiful day, decided to spend time down at the beach before lunch.

"Look. There they are." Juan pointed.

"Hard to see. Looks like ten of them. Naked. Too bad we can't play with them." Darrel squinted over in the direction.

"I wonder what gives with the break this morning?" Juan asked.

"I'm not really sure. She did say it was optional though." Darrel replied.

"Think about it." Alec chuckled.

"Hey now, I'm only 40, in my prime!" Juan chuckled back.

"Yeah, but it never hurts to build back up." Alec laughed. "I think it's more for the girls though. Pamela and Nina observe the girls pretty routinely, just to make sure everything's ok."

"You think something happened?" Darrel wondered.

"No, no... nothing we need to worry about. But, maybe ask John." Alec laughed.

"Why ask me?" John asked defensively.

"Lighten up John, it's all in fun. It's just that, well, look at yourself!" Alec said amusingly. "No, seriously, Pamela mentioned that Alissa is coming along, but thinks that a short break might be good."

"Oh, so it's John's fault!" Darrel laughed.

"Actually, Pamela has a pretty good method. She's been having John use a cock sleeve to prevent him from penetrating too deeply." Alec explained.

"Really..." Juan wanted more detail.

"Pamela didn't want to overwhelm Alissa her first go, and considering her size... What, five and half inches the first day, John? Anyway, Pamela started him on a 3 inch sleeve, and has been cutting about half an inch off every day. Alissa's a real trooper. I think Pamela just wanted her to relax and rest up this morning." Alec explained.

"Damn! John, do you think she'll be able to take it all?" Darrel asked.

"I don't know." John said plainly.

"Come on... you're the one that's fucking it. What do you think?"

"Come on, John, fill us in!" Juan became quickly curious.

"I don't want to hurt her."

"Ok, so? Do you think she'll eventually be able to take it all?" Juan insisted on an answer.

"It's hard to tell with the vibrator on."

"Vibrator? What's that have to do with how deep you go?"

"The sleeve has a vibrator in it. When I'm fucking, it almost feels like my whole cock is inside. But I can feel when the sleeve hits her mound, so that's all the deeper I go."

"But you feel the end of your cock? How does it feel? How does she respond?" Darrel inquired.

"I don't know." John sighed. "It's like... she feels the vibrations too. I can sort of tell she struggles. Her face and body twitches... it's like her body tries to move away when I thrust. But then she orgasms." John further explained.

"It's a bit of a struggle." Alec followed up. "But I think the vibrator makes it more pleasurable. John's cock is stretching her pretty good, without the vibrator she'd probably bail. John?"

"Yeah. It's pretty tight."

"So, day after tomorrow, you'll be home free?" Darrel hoped.

"By then there won't be anything left of the sleeve. Today it gets cut down to an inch, and that just leaves the vibrator part of it. It can't be cut any more than that." Alec said.

"Damn." Juan said.

"Well, maybe the vibrator is key." Alec brainstormed. "John, you can use a standard silicone vibrating cock ring. Fuck her slow at first, inch in, and let her adjust. When you're just about balls deep, the clitoral pad will vibrate against the clit and maybe that'll do the trick."

"Man, I'd love to see that." Darrel said with envy. "How's yours, Alec?"

"Perfect. Almost like a seasoned whore once I tell her what I want. All of the girls have had good training."

"You're using a sleeve too?"

"No, I'm just six and a half... don't really need to. Well, you saw Trista. She's not fat by any means, but she is a little more meaty than yours are. Just be easy on the ass." Alec chuckled. "Someday they'll be able to take it all, no need to injure them now."

"One thing I've noticed is how well they're cleaned. It's never a problem sticking it into her ass a few inches, and then slip it right into the cunt." Darrel added.

"Remember the first day? You guys were let down that they weren't like Pamela. What happened?" Alec prodded.

"I'd still hit Pamela in a heart beat. Come on, Alec, she's beautiful! No doubt her firm ass would take it all!"

"Yeah she is. But, nah... like I said, way too old for me. What about you, John?"

"Pamela is what I had in mind."

"Well, you're not complaining anymore. Once pussy is soaking wet and sucking that cock, nature seems to take its course."

"What I like is, there's nothing to worry about, if you know what I mean." Darrel added.

"All this talk is getting me worked up." Juan laughed.

"Quick game of volley-ball, then we'll hit lunch..." Alec suggested.



Chapter 9



©2020 Nurture Nature