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Introduction:

Yesterday you were a man. Today you're becoming an experienced woman. Wendy is now introducing you to sex. The sort of mind blowing sex that would have been impossible yesterday.
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 this are diverging story lines.

PLEASURE ISLAND: THE POOLSIDE ENCOUNTER

Chapter 4A Meeting Jacob

Laying there pretty much exposed with your ass hanging in the air your excitement is tangible. Then you realize exactly how far you're not only willing, but hoping that this will go. Ripples of excitement are coursing through your body to the extent that it's physically manifesting. Your abs are clenching and releasing, your ass cheeks are flexing and spreading of their own accord, and your breasts are heaving with each ragged breathe you take in anticipation. If something, anything doesn't happen soon then you're going to die.

You can hear Wendy behind you sorting through her newly bought bags and opening packages. Plastic pops as items are opened and messed with. You've discovered that each time your ass flexes it pulls the g string tight and rubs those pearls in an exotic and erotic way that you'd never have imagined. You're not even dripping wet anymore at this point you can feel your juices running down to meet your thigh highs. They are going to be soaked soon.

You feel Wendy behind you again. "Are you ready to lose your virginity to me?" She doesn't even give you enough time to process what she's said or for the slight panic to set in at her words before you feel something push against the outside of the lips of your little pussy. It strokes up and down a couple of times and then it's invading you. You can feel it push inside of you. You can't breathe as the length and width of it fills you. You try to pull forward, but Wendy's hands are on your hips holding you steady.

"It's ok baby." She whispers trying to soothe you. "The first inch is already in. I promise that you can take every bit that I give you and you'll love it."

The first inch? There has to already be at least 8 inside. It has to be bigger than a coke can around. It feels like it's going to split you in half. It doesn't hurt, it just feels so big! It's too much. "Relax baby. Deep breathe in deep breathe out. Don't clench. If I can take your big cock, then you can handle this little guy."

"Please don't refer to it as guy. I still don't swing that way," you mutter.

"Really because from back here it looks like you'd love the cock." Her voice is half laughing and you can't help but laugh as well. As soon as you do laugh you feel it slide DEEP. "Oh that's a good girl. Only about another inch to go."

"Oh fuck. It's huge." She doesn't move and just stays still so that you can get used to being stretched out. You start to breathe normal or at least closer to normal. You can still tell that your getting wetter and wetter.

"That's it baby. Big breathe in for me." As you take the breathe she pushes in. You can feel her hips against your ass now. "Oh yeah baby. I'm balls deep in you now." She leans forward and starts kissing on your neck and ear. "I'll be gentle... for now." Her words ignite fear and excitement both. You've always loved rough sex, but before it was you in control. You thrusting. You trying to feel her cervix with the head of your cock. Now you're taking dick deep within you in place that are not only unexplored, but didn't exist yesterday. But you still want it. You're already craving it deep, hard, fast, and even a little brutal.

She slides just slightly back. You don't know if it's a relief or a disappointment. She slides back forward. The pearls of your thong are pulled slightly in with the dildo and rub on your lips in the most amazing way. Holy shit! Your getting fucked with a dildo. No, a strap on. Her hands are still on your hips and she's not holding it, so it must be a strapon.

You can't help but open your eyes and look behind you. There she is. Blonde hair cascading around her face, green eyes twinkling, pouty pink lips turned into a smirk. Her tits are up against your back. You can see a black belt going across her waist. Wendy leans in for a deep passionate kiss. "You like the view." Mmmmm is all that you can manage for a reply. "Do you wanna see it?" She raises her top half of of you and slowly pulls back. You can barely see the strapon as it pulls out of your tight little pussy.

It's tiny. It's only half the girth of your cock, but you feel such an emptiness as it retreats. "Ahhh." Holy crap what is going on with the inability to speak. But God that felt good. You don't get to see how long it is because she's already pushing back in. This time it's lots of stuffing. The friction of it sliding in combined with those pearls hitting in all of the right places has your head lifting of its own accord. You're now leaning on your hands and did you just push back against Wendy? Either way, she has bottomed out again.

She pauses and then slides out and right back in. "Oh God." Your voice is ragged and broken, but at least you still have a voice. "Oh fuck me." It was meant as an expression more than anything, but Wendy takes advantage.

"Thatagirl, take every bit of that cock." She starts to slide in and out faster. "You're loving that cock aren't you?" The moans coming from you are all that you can give her. But it seems like that's all that she wants right now. "Get ready for your pussy to explode. I'm gonna make you come so fucking hard."

The rhythm of her hips driving into your ass is getting faster and faster. Your pussy is clenching that strapon as it takes you. The juices from your pussy are keeping it moving so freely. She reaches around and strokes your clit and you finally explode.

"Oh my fucking God, cum inside of my baby. I want to be your slut. Keep fucking me. Pound my pussy." Holy shit, you didn't even know you could yell that loud. The convulsions in your pussy keep coming. It's only getting stronger as your legs clamp together on their own. "Fuck me, don't stop."

"Oh fuck I'm gonna cum too," Wendy declares from behind you. "Your pussy is so good! I'm gonna fuck you all night. I'm gonna make you know that this pussy is mine." She keeps pounding into you even as your knees are shaking and barely keeping you upright.

"It's all yours. Keep on fucking me. Please don't stop. Mmmmmmffffffuuuuuccccckkk?"

"Oh, that's it baby!" She thrusts one last time hard into you and her hands come around you to plant on the dresser on either side. Her hips are shaking with her orgasm. Every quiver of her hips shakes the strapon inside you.

"I need to lay down baby," you tell her.

"Ummmhhhmmm." She slowly pulls out of you. As the head of the dildo pulls out you feel so empty now. God you already need it back in you.

Both of you make your way to the bed. She has you lay your head on her breast and hold you. "I told you that you could take it." You look down at your new best friend and realize it's not quite how you thought it would look. There is a leather strap that goes around it, but all of the others that you've seen has the dildo resting on the woman's hip bone.

This one is lower and the dildo goes through it not against it. You raise up to check it out closer. "You like Jacob?" she asks.

"Jacob?"

"Ummm, anything that makes two women cum that hard at the same time deserves a name don't you think?" You look closer and realize that it has a hook after passing through the material so that it curled inside her pussy. She had just fucked us both with Jacob.

"I think I'm falling in love with Jacob," you say as you lay your head back down on her chest.

Both of you could only lay there for so long. Your orgasm while taking Jacob nice and deep had lasted longer and been stronger than any you'd ever felt as a man. You're addicted now. You're already looking for your next fix.

But how do you want it? There are so many ways, but which one right now? You could mount her strapon right now and ride it until both of you have an amazing orgasm again. You could wear the strapon and fuck both of you to another orgasm. You could let Wendy take the lead and figure out what she wants to do to you next. You could 69 her. You could see what else is inside that huge bag of fun and pleasure.

At least all of the roads lead to more orgasms.

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