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Chapter 11 by jk89
What are you thinking?
It's time to slide your dick in her ass
Unable to resist the site of her puckered hole in front of you, you begin lightly rubbing your thumb around the rim. "I've already had my dick in two of your holes Kelly, I think it's time I put it in your third." you told her, more than asked her, with a tone of authority to your voice. "I'm going to be the one to pop your anal cherry, and it might as well be today. How hot will it be knowing I'm putting my cock in the one place Brandon never has, or ever will?" you asked her, slipping your thumb into her sphincter up to the first knuckle.
"Ohhh fuccckk!" she groaned out at the feeling of your thumb entering her backside while sounding like she's drunk from the multiple orgasms she's had. . "David, you can do whatever you want to me. Just use some lube. There's a bottle in my nightstand." she said, indicating the one closest to you.
Expecting to see a drawer overflowing with random objects and odds and ends, you were pleasantly surprised to see that the drawer appeared to be dedicated to storing sexual products and toys, with a variety of different sized dildos, a couple of vibrators, and a pair of handcuffs and blindfold, in addition to the lubricant you were looking for. Smiling at the site, you make a mental note that the two of you will have to experiment with some of those things in the future, before grabbing the bottle of lube and generously coating your dick.
As you positioned yourself behind her, Kelly arched her ass up for you, apparently ready and willing to take her first dick in her ass. The sight of her curvaceous ass, ready for you to claim it, is intoxicating and you position the tip of your cock then slowly push into her tight asshole. She took in a sharp breath of air through clenched teeth and her muscles constricted reflexively around your dick as your mushroom tip slipped past her tight anal ring causing you to pause your movements to let her become used to you.

"Don't worry, I'll start slow." you told her in a soft, soothing tone, bringing your mouth to her ear. "Tell me, have you ever used any of those toys I just saw in your drawer up your ass?" you asked her, trying to gauge how much anal experience she's actually had while also getting her to think about something other than the feeling of you trying to violate her with your swollen shaft.
"Right before I found out Brandon was cheating on me... Unnnnggghhh... I started experimenting a couple times with the smaller ones, thinking I could try to spice up our sex life. Nothing as big as you thouggghhhh...." she said before her words turned into a long, distracted groan as you managed to penetrate her even more.
Her ass seemed to relax a bit when she talked so you figured you'd keep it up. "God, I just got harder thinking about that. I bet you looked so hot doing it. Tell me how you did it. Did you ride it or did you hold it in your hand?"
"I've tried both of those ways," she admitted to you "but I liked holding it and being on my knees better. I was able to relax easier."
"Oh fuck, Kelly, I can feel you relaxing for me too. You've already let me put half my dick inside you. I'm glad we're not letting that practice go to waste." you told her as you admired the site of your thick meat pole penetrating her backdoor. "So, were you able to make yourself cum when you fucked your own ass?" you asked her as you began to introduce short movements in and out of her.
"Ohhh... One time I did... I...I was watching a porn where the girl was on her hands and knees getting absolutely drilled in her ass. She was loving it so much David." she told you as her breathing became more labored. "It was so hot... I started speeding up to match their pace... Picturing I was the one getting fucked like that. Before I knew it, I was screaming and cumming along with her... Oh fuck, that's starting to feel good!" she then told you moaning as her attention was drawn back to the situation at hand.
"Oh yeah Kelly, it is starting to feel good." you agreed with her. "Fuck, look how quick your ass has opened up for me! Do you want it fast like that porn you watched?" you asked as you began increasing the length of cock you slid in and out of her.
"Oh fuck David, I think I do! I think I want you to make me your anal slut! God I'm such a whore for your cock. Make me cum again with your fantastic dick stretching out my ass!" she begged you, apparently becoming accustomed to the anal intrusion and no longer tensing against it.
With how quickly Kelly relaxed and started begging you to "make her your anal slut", you had the thought that maybe her anal experience might be a little more than what she was admitting to. She was still tight as hell, though, and you really didn't give a fuck at that point. All you cared about was taking full advantage of this opportunity and started picking up your pace to give her what she asked for.

"Oh fuck David! It's so fucking much! You're gonna split me in half, but I don't care! Fuck my tight little shit hole like it's my pussy!" she screamed as you speared in and out of her tight sphincter. "Fuck my ass like you own it and make those balls slap against my pussy!... Oh god YES! YES! Use my ass! Do whatever you want to me, just keep fucking me with that cock!"
You've fucked a few girls up the ass before, and some of them were really into it, but none of them could match the enthusiasm mixed with the filthy talk that was spewing from your sister-in-law's mouth at that point. Combining that with extra, tight grip around your dick, and it wasn't long before found yourself tantalizingly close to cumming once again. You had no intention of pulling out this time and continued working in and out of her thick, jiggly ass until you felt your balls begin to tighten, then buried your cockmeat as deep into her ass as possible. Letting out an uncontained, guttural yell, the first blast erupted from your tip, spraying your jizz deep into her bowels. Kelly's screams joined yours at the feeling of your release, and you continued pounding in and out of her ass, lost in the moment, pumping wave after wave of your ejaculate into her anal cavity from some hidden reservoir of semen you didn't know you possessed, until she was brimming with your cum. Your orgasm was never going to last forever though, and when you felt your contractions slow, then eventually stop, you kept yourself buried inside her for a few seconds, plugging her hole as the two of you, sweaty and breathing heavy, tried to recover.
Physically spent, your body couldn't maintain your erection any longer and you felt your dick begin to soften inside her. You knew it was only a matter of time before your flaccid member slipped from her confines, but that's not how you wanted things to end. "Stay just how you are." you instructed Kelly as you began withdrawing from her rear end, then focused on the site below you as you slid yourself free, pulling some of your cum along with you, and causing it to leak down onto her pussy lips. "Let me see you push that load out for me." you told her next as you began stroking and massaging her plump ass cheek.

Kelly listened like the good slut she'd shown herself to be and the next moment, the first rivulet of cum began leaking from her ass. A second later she let out a surprised "Ooh!" as a larger globule was ejected with a loud "pfft", coating her pussy lips even more before dripping down between her legs to land on her bed.
"Fuck Kelly, you're incredible." you complimented her, not for the first time today. "Sex with you is amazing! I don't think I've ever been with anyone quite like you before." you said as you moved to lie down on the bed next to her.
Letting out a small laugh at your remark, Kelly lied down next to you, pulling her body against yours, and rested her head on your chest. "Thanks David, but that was wild even for me! You just brought it out of me I guess, so you deserve some of the credit too." she said as she began lightly rubbing your chest with her hand.
"So what did you think of your first anal, if it really was your first?" you asked her, wanting to answer the doubts that had come to mind.
"I wasn't lying about that David, I've never had anyone fuck my ass before. You were my first, and it was intense. I think I'm going to be sore for at least the next few days, maybe even the rest of the week." she laughed. "I don't think we could have gone that hard if you hadn't gotten me so worked up and made me cum so many times before that, but I'd definitely let you do it again... Just not right now!" she said, before you could get any ideas.
"Don't worry Kelly, I think it'll be a little while before I can perform again." you reassured her then the two of you fell into silence, eventually nodding off to sleep in each other's arms.
What's next?
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A Saturday to remember
You get to live as a 28 year old in the prime of his life. You have a wonderful, sexy girlfriend but also other women throwing themselves at you. How will you choose to live your day?
You get to live as a 28 year old in the prime of his life. You have a wonderful, sexy girlfriend but also other women throwing themselves at you. How will you choose to live your day? Do you try to stay faithful? Or is today the day you start cheating on her?
Updated on Dec 24, 2024
by jk89
Created on Feb 16, 2019
by jk89
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With every decision at the end of a chapter your game state can change. Here are your current variables.
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