Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 21 by MonsterBox MonsterBox

Risky play. Is she up for it?

Enthusiastically so!

Alex: God, I thought you’d never ask!

Alex: (Alex grins up at you from her bed, then waves a little shyly with one hand; she then uses it to pick up the big, red dildo, much shinier than it was last time you saw it, and move her hand down; she pans right past the vibrator working her pussy, then spread her legs and lets you see her gently rest the head of the dildo against her asshole)

Alex: I don’t know if that’s going to fit, Adam.

You: Aw. Are you asking to stop?

Alex: Not even a little.

You: Then take my big, hard cock up your tiny, sexy ass.

Alex: (the toy pushes past the tight ring of Alex’s asshole, and she moves the camera back up; definitely a good sense of cinematography, because the pained, excited expression she makes as she starts to feed what she’s thinking about as you into her butt and the agonized groan she still makes with a broad, uninhibited smile drives you absolutely crazy)

Alex: I feel like your personal porn start right now!

Alex: Mm, I also feel so fucking full of you.

Alex: It’s hard to wait for the real thing, thinking about having something even bigger in my ass.

You: Are you ready to start getting a real buttfucking, then?

Alex: Please do!

You: Ram your tight ass with my cock while you feel my fingers on your clit.

You: I want you to feel every inch of this, let it soak into you.

You: Fuck, I can feel your ass strangling my prick right now!

You’re not lying, either, as you speed up, precum coating your cock as you imagine fucking your girlfriend’s sexy ass. The videos she’s sending aren’t helping you slow down, either, positively captivating your attention with how her face looks taking something hard and rough in her asshole, along with how her actual butt clenches lovingly around the toy both of you are imaging as your violating prick.

Alex: God, harder!

Alex: (Alex’s next video is a little blurrier, but it’s not hard to see that she’s hammering her ass with the dildo, the buzz of it telling you it’s quivering inside her with each thrust; she screams and gasps, then transitions from what she’s doing to her butt to how her face looks right now, clearly starting to cum for the first time tonight, showing you her bouncing tits as she works herself over)

Alex: I’m already cumming, Adam! Don’t stop!

Alex: You’re ripping me apart, keep going!

You: I love hearing you beg for this!

You: (in the heat of the moment, it’s possible this isn’t the best idea … but you don’t care; you take a short video, then send it, letting her see you pumping your cock, wet and throbbing and so ready to burst)

Alex: Oh my GOD!

Alex: You weren’t fucking kidding, huh?

Alex: Shit, I’m about to cum again! Please fuck my naughty little ass, please make it rough!

You: I’m about to cum, thinking about pillaging you from behind.

You: Squeeze that fine ass around me, make me fill you up!

You: You’re so fucking sexy, I don’t think you can even take all the cum you’re about to make me give you!

Alex: Do it! Please cum in my ass, Adam!

Alex: Fuck, I’m cumming again, please fill me up! God, make me overflow, make me swell, make me burst!

Alex: (Alex’s pussy is already dripping, but starts to squirt violently as she gets hit with orgasm after orgasm as the sex toy inside her strikes with increasing ****; you can’t see her face this time, but the high-pitched, violent screams of joy as she cums are more than enough to help you over the edge)

You: Yes, God, yes! Take it, Alex! Take every last drop of my cum!

You grunt as you finally explode, balls tightening as your pulsing prick gushes over your hand. It’s a lot, even for you, but clean-up is for post-orgasm-you to deal with. Your eyes roll back as you hear her repeated requests to fuck her harder and her orgasmic cries.

You: (you let her see you cum, too, the sheer amount of semen flowing out of you absolutely insane by now; you can’t even imagine how much of it she could actually take, but you’d hardly mind seeing her overflowing with your seed or covered in it … though the more violent images she suggests also show up as you keep jerking, only stopping when you can feel your nerves overload and start to make the sensations more uncomfortable than enjoyable)

Alex: Holy shit, baby.

Alex: I thought I was exaggerating.

Alex: You always cum that much?

You: Honestly, not until I started jerking off to you.

You: You just put me into overdrive, then … well …

Alex: I get that, trust me!

Alex: Thanks for helping a girl out, though.

You: Really feel like you did more for me than I did for you there.

Alex: Uh-uh. I can’t boss myself around. Giving up control is so exciting.

Alex: I love trusting you and giving you full reign, it’s something I can’t do with anyone else.

Alex: Though I’m sure I’ll love it a LITTLE more when it’s that absolute creature pounding me instead of a piece of rubber.

You: And I love that you trust me that much. Also, the name-calling and the rough sex parts.

Alex: I miss you.

You: Tell me when we’re booked, and I’ll be there.

You: I miss you, too. This whole date thing is horrifying, but I’m so excited.

You: It’s going to feel so good to be able to touch you again.

Alex: I know!

Alex: I can hardly wait, but I will. I can be patient.

Alex: Oh, do you have a TV? Or a streaming thing?

You: I … can.

You: Why?

Alex: I don’t know, I just … it’s stupid.

Alex: I had some shows I wanted to get you to watch. And I thought we might be able to, you know, watch it together?

Alex: If we can’t be in the same room yet, maybe it’d be a nice, relaxing thing after a hard day to still be able to chill out with each other and do something mindless.

You: It’s not stupid. But I’ll need to figure out how to make it work. My place is crazy out-of-date.

You: What were you thinking of?

As the two of you discuss viewing options, as well as how to get you the ability to view them, the night calms. With your urges both fairly spent, you take most of your time talking, joking, prodding each other’s taste in questionable media, and thinking about what the future might hold. It’s never seemed so likely to you that it might actually have something good in store.

Let's check in on your date night. Feel ready?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)