PLEASURE ISLAND: THE POOLSIDE ENCOUNTER Chapter 11AA Theme Trips/Tours-Pirates- Satisfying the Crew by Evolved+Prestige

Rating: 66%, Read 1824 times, Posted Mar 16, 2021

Fantasy | Bi-sexual, Blowjob, Body modification, Cum Swallowing, Erotica, Female, Fisting, Group Sex, Lesbian, Male, Pegging, Threesome, Transgendered

This is a repost from another site that I've been writing on. This has been a choose your own adventure series, so where there is an a or b following the chapter number these are diverging story lines.


Chapter 11AA Theme Trips/Tours-Pirates- Satisfying the Crew

With Wendy's announcement you go ahead and down your glass of rum. "Well this is going to be a busy night. There had better be a lot of lube available."

Wendy comes to you and kisses holding you behind the neck. Then she begins running her fingers over the shaved part of your head. "You're going to be getting a lot of lube baby, don't worry." Then she looks at the officers around the table. "Can you make sure that the rest of the crew is well fed and has some rum as well. You can start to pass the word that tonight's entertainment is almost ready." You breathe deeply and feel the first bit of true apprehension since arriving on the island.

As the others leave the room Wendy looks you in the eye. "Are you alright? Is this something that you're actually OK with?" You can tell that she's worried about you and you're honestly worried about her.

"With this many people on board are you going to want me again after I do all of this?" You're worried that after fucking this many people, especially in one night, that Wendy would never want anything to do with you again.

She pulls you in for another deep kiss. "Baby, I look at it as you are trying secure our future. You are taking care of us again. You are still my hero and always will be." She kisses you again. "I think that you should enjoy the night. Nobody is going to rape you or make you do anything that you don't want to do. You should honestly get a much out of this as anyone is getting out of you."

"Yeah?" You look at her trying to see the truth. Wendy's face and mannerisms tells you that she's being honest. As long as you're both communicating and both agree, then there's nothing that will pull the two of you apart.

"Baby, I love you and always will. And..." She pulls you in close again and runs a hand up your skirt grabbing your ass. "I'm going to be the first and last to have you tonight." She sits you back on the edge of the table lifting both of your skirts upward. She sinks we cock deep in immediately. Your pussy is already so wet from talking about all of the sex that it inhales every inch that she has.

"Yeah baby. This pussy is mine. I may be letting others get some use out of it, but it's coming back to me. I'll be the last one buried in it every night for the rest of our lives. I'm going to love watching you take every cock tonight. And then I'm going fuck you again." She's gently stroking in and out of you. She kisses you again. "I helped design you this body. It's built for sex. I can't wait to see how your doing by the time we are done tonight."

She slides the silk bust covering of your corset down so that she can have access to your nipples. A shocked smile covers her face. "Oh I like that." She pulls on your nipples and it's even better than before. You look down to see what she's doing. You have a small diameter but at least a 6 guage gold ring through each of your nipples. Wendy is still gently pulling on each ring.

It feels so amazing. "I guess that I know where my pirate rings have been," you say breathlessly. She lifts a nipple to her mouth taking a ring between her teeth pulling and covering her wet slick lips on the nipple. She's still thrusting into at a steady rhythm. Ah, that feels so good. Your filled with cock and getting your nipples taken care of. You feel a slight building toward your orgasm, but it really jump starts as she releases your nipple with her mouth and goes back to kissing. She's hammering inside of you now seeking her own release.

"Those rings stay from now on understood?" she demands. You can only mumble an agreement. She runs her fingers across the side shave of your head and grasps a hand full of the longer hair as she reaches it. Her other hand returns to a nipple tugging and pulling. Her hips are flying in and out of you. Finally with one last hard thrust she buries deep and let's out a torrent of cum filling you deep. It's pushed you over the edge and and your orgasm crashes over you. You wrap your legs around her hips pulling her even deeper.

"God damn, that cock is amazing!" You grip her dick tighter with your pelvic muscles emphasizing your point.

"Damn, I love watching you two." The sound of the voice is unexpected but not terrifying. You look over at Kemorea standing in the doorway. "There are a couple of people that would like to meet you." She steps aside and three guys walk in looking around a bit nervously. You're still enjoying the dying waves of your orgasm and can't even really take note of their looks.

You lean in close to Wendy. "Well baby, I guess I've got to get to work."

She laughs a little. "Have a good night. I hope that it's a good and productive shift." She slowly pulls out of you and you can feel her cum start to run out. You stand and strip. There's no since in getting cum all over your cloths when there's no washing machines handy. You look at the new comers. The tall blonde has pulled down his pants and staring rubbing himself hard. One of the dark haired guys is shorter. He has pulled his shirt off and tugged his pants down. He's still slightly limp at 4 inches. The other dark haired guy is medium height and build and standing naked fully erect at 6 inches.

You walk over and push the limo guy into a chair and take him into your mouth. You use your tongue and start coaxing him to harness. The guy that was already hard lines up with your pussy and buries himself inside of you. You're sucking and fucking now. You glance toward the bed and Wendy is stripped naked rubbing her pussy from underneath her cock. She's clearly enjoying the show. Without even touching her cock it's rock hard and thick with precum glistening from the tip.

The cock in your mouth is fully hard after two minutes and at five minutes you feel the guy behind you start to cum. It's not nearly as powerful as Wendy's and he's making really loud grunting sound as he finishes. She tapped out quickly and the other guy takes his place thrusting. She's a good bit bigger and you can feel the already deposited cum pushed out of the way as he sets claim to your pussy.

Another cock comes into view near your head and you start stroking it with a free hand. You make sure that you continue to suck off the guy in front of you while picking up the speed in your hand. You pull your mouth off of the one that you've been sucking and take the new arrival into your mouth. The guy in the chair starts jerking himself off and moves behind you getting in line for his turn inside you.

The guy fucking you now finishes and deposits his seed. The next dick in your pussy is thicker, but didn't reach into you as far but after a nice long blow job he's dedicated to making it good for. He's reaching under playing with your clit and driving himself good and hard into you. The dick in your mouth let's loose a nice flood and your able to drink all of that cum down.

The guy fucking you pushed hard on your clit and like a magic on switch he starts your orgasm. You continue sucking and start fucking backward onto his cock. As he starts to cum inside you you're cuming on his cock.

This continues for about an hour with you sucking cum out of almost half the guys that you suck and most of the guys that fuck you last less than 8 minutes. You need a break though. Your pussy isn't sore and your still horney, but you need a drink of something other than cum. Wendy pours you a cup of rum already knowing what your after.

"Oh God, this is so fucking hot. You've gotten off like 12 guys already. I've seen gang bang videos on that didn't have this many dicks." She tampers down her excitement slightly. "How are you doing?"

"Uh, actually... I feel fucking amazing," you confess. "My body is eating this up. I've had like four orgasms. All of the guys are using enough lube that I'm not hurting, fuck, I could go on like this forever."

She kisses you deeply again and you know that she can taste a couple guy's cum. "Nobody has used lube. Cum is the only lube that you've gotten. It's so hot watching a guy fuck another guy's cum out of your pussy. If I could record this, then we'd be millionaires." She kisses you again. "Who am I shitting? I want a copy so that I could fuck you while watching you fuck them all."

Kemorea walked up to you now. "Good news, or I guess bad news," she says looking at you. "You've already fucked almost half of the crew that are going to take you up on your offer. But this has really worked. Everyone is in great spirits. There's even fucking and blow jobs happening out on the deck. Straight people are experimenting in ways that they never have before, and I've never seen an orgy on any ship. I mean we all came to the island for sex, but most people can never let go this much."

Kemorea has definitely come around from dismissing you as just someone to deal with to now bring awestruck. "My lady, can the officers still get in on this?" he asks hopefully.

"I never said that she was going to fuck any of the officers," Wendy speaks up sternly. Kemorea looks taken back and a bit angry. He starts to argue but is cut off by Wendy, "I said that you'd be taken care of. And if I can't fuck any of the crew I can at least take care of my officers, right?" She pulls you in for one last kiss. "Back to work baby." She smiles at you as she leads Kemorea by the hand towards the bed.

You watch her ass away as she goes and you can see her cock swinging between her legs as she goes. She gets on all four facing towards your fuck station so that she can continue watching and Kemorea takes his place behind her. By the time that you've got your next couple of guys lined up and ready for you Wendy is already being pounded.

You lay on your back and are immediately filled with cock in your mouth and pussy. You're able to watch a Wendy is getting fucked and watching you get fucked. Being able to watch her heightens the experience and it doesn't take longer before you're cuming on the cock that is railing you currently. The cock in your mouth erupts making it even better. You clinch on the dick in you needing your other serving of cum. It didn't take but another second before your rewarded. He begins shooting his load inside of you.

By the end of the line of cocks you've had big and small, large loads and small loads, quick shooters and those able to give you an orgasm. Your skin is electric. Your body is primed with energy. Wendy has 4 of the officers in bed with her at once and they are all fucking and sucking each other. You decide to head out on deck to get fresh air and hopefully find some fresh dick. Sully is there looking over the railing.

"Hey big man. You're not getting your fill?" you ask.

"Uh, not really my thing," he replies in an uncertain tone that you never thought you'd here from the confident giant.

"You came to Pleasure Island and sex isn't really your thing? How does that work?"

"Long story," he admits barely over a whisper.

"I've got time." You can tell that something is really bothering him. You place your hand on his large forearm trying to show a much kindness as possible.

"Ugh, when I came to Pleasure Island I didn't know what I actually wanted. I was bi curious so I picked this body so that I could try it out. Now, I realize my mistake. I was much happier as a woman getting some where I could. Now there are no guys that want someone like me. Very few get guys are into a guy as big as me and those that are interested aren't wanting to be top."

Holy shit. Sully was a chick! And that chick now wants dick! Your mind is about to explode as the officers leave the Captain's cabin and a light bulb goes off. "Can you find Lucinda and bring her to me and Wendy?"

"Sure," Sully sounds so defeated nuts head off anyway.

You run in and find Wendy laying on the bed with cum all over her. Her stomach is coated from either her own cum or one of the officers. She has more on her breasts. You lean down and lick the cum off her nipple and suck it in deep. It's saltier than hers, and you immediately chuckle. "What's so funny?" she asks.

"First off, I'm eating cum off my girlfriend. Second, I love it. Third, I've eaten enough cum lately that I can tell that it's not yours."

She doubled over laughing. When she can finally talk again, "You're a CUMoisseur!" She's back to laughing. You can't help but laugh too at her stupid joke and the accuracy of it.

"Hey, I have something serious for you." Wendy calls down a bit and looks at you. "Sully needs to get laid as well."

"I was wondering where the giant was. I'll be honest though as big and built as that guy is I don't know if I could take that big of a dick if it's what I think it's going to be."

"Well, you may be in luck there. SHE isn't so happy with her transformation and SHE is a bottom." Wendy's eyes widen huge. "I know, I thought I'd be the only one that would be into a gender change. I didn't expect that anyone else would give it a try." You wrap your hand around her very familiar cock and give it a couple strokes. "And I know just the person to give her the dick that she wants."

"Julia, Lucinda is here," Sully says from outside the door.

"Can both of you come on inside," you answer. The door opens and both enter. Lucinda looks very excited and Sully is looking nervous. You pull a sheet over Wendy's hardening cock. "I think that all four of us can help each other." Lucinda comes over and sits on the bed, but Sully lingers back. "Sully, what name do you actually want to go by, or what name did you used to go by?"

Sully looks very nervous now. "My name used to be Sarah, but that didn't really matter anymore." Lucinda looks amazed.

"It's nice to meet you Sarah." You hold out a hand and she takes it wearily. "I used to go by a man's name until a few days ago," you explain. "So I get the weirdness of a gender change. I think that I like my change more than Wendy or me expected though. She wanted a lesbian filled week, and I honestly thought we were going to a normal beach for drinks and sex in the sand."

Wendy laughed coyly, Lucinda was pretty much also jawed, and Sullu actually smiled. "You told me that you were curious and that's why you chose the body that you did." Sully nodded. "Well, Wendy was a bit curious too. She's not a lot different from her normal, she's always been a blonde bomb shell, but she has bigger tits, a rounder ass, and..." You lower the sheet a bit exposing her eight inches of excitement. "And one other change. Wendy is actually the perfect person to be curious with as she has everything," you lift her cock out of the way to expose her dripping wet pussy, "to experiment with."

Sully can't look anywhere else except at the cock that is being offered. You look over at Lucinda and she is breathing hard already. Her nipples are showing through her top and she is taking everything in. "And you and I have a date as well." You reach out and grasp her breast giving it a squeeze. She moans into the feeling. You remove her top exposing her B cup breasts with very tight nipples poking out. She slides her pants off and lays next to you in bed and the two of you begin to kiss. She plays equally with your tits and pussy and you do the same.

After a few minutes you glance over and see Sully giving Wendy head. Sully is completely naked and the body that is exposed is chiseled from marble. Every movement makes the muscles look like they will cut their way out from under the skin. The dark skin reflects light from the lanterns that has been lit. Wendy looked to be in heaven. Both are moaning in time to each other.

Lucinda slides down your body and begins eating twenty plus guy's cum from your pussy. She seems to be in heaven as well. She puts four fingers in your stretched out pussy and pushes in until her thumb catches in the way. The feeling is amazing. Even with a much dick as you've sucked and fucked this evening your body needs more. You need more sex. You grab a handful of Lucinda's hair and pull her in tighter. She focuses on your clit and begins fucking you faster with her hand.

You hear Wendy groan as she cums into Sully's mouth and Sully moans as he drinks her down. You begin cuming as well. It's not the strongest orgasm of the day, but satisfying. Lucinda keeps on eating you out licking your clit as Sully lays down and Wendy mounts from the top. Sully's muscles tighten slightly as Wendy slides into that tight ass hole that hasn't been used in years. They are missing and you can see briefly from time to time their tongues dancing over one another. Wendy is stroking herself all of the way in and out of Sully's hole. Sully is moaning on every push forward.

Sully's cock is rock hard and with legs up allowing Wendy deep into that ass Sully's dick is almost titty fucking Wendy. Sully has to be thirteen inches long and even bigger around than a soda can. Wendy starts stroking the huge cock in time to her thrusts. Her hand doesn't even wrap fully around the big beastly cock and she has to use the other to support herself. You reach out and intertwine you fingers with hers and stroke Sully with her. The two of your hands barely reach all of the way around it.

Suddenly everything happens at once. Sully let's out a moan and arches up. You can feel the strong pulse through his shaft as cum rockets out. It hits Wendy's tits, it goes through them and lands on Sully's face, it shoots up and hits Wendy's face, and there is enough to begin dribbling down into your hand. Wendy moans as Sully's ass tightens around her cock and she thrusts as hard as she can and then holds deep inside Sully's bowels emptying herself. Lucinda hearing all of this has put her thumb into her hand and thrust further into you almost too her wrist.

She is fisting you now as hard and fast as she can all the while sucking hard on your clit. You explode on her hand. Your back arches up of the bed and your legs start to shake. "Ahhhh, fuck." Your not sure if anyone else shouted out or made any noises because all that you can hear is the blood pumping through your pussy and and the cum shooting out of your pussy.

--- Leave a comment of other chapter ideas that you'd like to see--

Rating: 66%, Read 1824 times, Posted Mar 16, 2021

Fantasy | Bi-sexual, Blowjob, Body modification, Cum Swallowing, Erotica, Female, Fisting, Group Sex, Lesbian, Male, Pegging, Threesome, Transgendered


Login to join the discussion