So continuing on with this story. And I’m not sure if this sub needs a trigger warning, but there will be pegging in this chapter so fyi.
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After getting back together and her gently shoving in my face the fact that she’d been getting dicked down by a hung guy between us breaking up and getting back together, things were okay for a few weeks. My mind kinda fixated on that. But it was honestly business as usual. School, work, and we’d hang out and it was like before we broke up. There were definitely some nights it seemed like she was working later than normal (plot twist, she wasn’t working late. But I’d find that out later), and she’d occasionally have weekend plans with the girls. But beyond that pretty normal with the exception of sex.
She kept alluding to things she’d done, as well as she wanted more. Like she was kinkier. Wanted me to be more dominant in bed. Tie her up. A few different things. We even got on the topic of anal, something I’d never done and wanted to. And she said “If I get to peg you, you can fuck my ass”, I’d never even really thought about buttplay before. But I really wanted to fuck her ass. In my head I think I assumed she’d never been fucked in the ass before and doing that would reclaim her for myself. And it was a little taboo. I wanted it. So I agreed, she could fuck my ass with a strap on if I could fuck her ass.
After a few weeks of training, I thought I was ready. I’d gotten a beginner butt plug kit and had worked up to using the biggest one and thought even that was overkill. It was like 6” long and 1.5” in diameter. Rachel had suggested I get that training set. And I thought we timed it up perfectly. Summer had just started and she had gotten a job from a family friend to watch their house for a week while they were out of town. I’m thinking this is perfect, we have a house all to ourselves for like 9 days. And at some point I’ll be able to fuck her ass.
That Friday night I head over with an overnight bag to meet her. We have take out for dinner and are just hanging around watching tv when I initiate. Start making out in the couch before going down on her. I got her to cum on my tongue before I ask if she wants to go to the bedroom and let me fuck her ass. She got this mischievous grin on her face and told me she wanted to go first. We get into the bedroom and she pulls this monster black cock out of her bag. Like definitely at least 9” and I’m thinking there’s no way that’s fitting inside me. But Rachel is so insistent and she kept asking “don’t you want to fuck my ass? You’ve got to take this first!” And my horny depraved mind said fuck it.
She’s got it 6” deep inside my stretched the fuck out ass when she tells me “I hope you like the mold of Kenny’s cock. That’s right baby, this is the same cock that’s been inside me. Now you get to experience it too. He made this for me” I didn’t even know what to say, my mind went blank. But she kept going “this is how it feels when you fuck me, and THIS (she pushed it balls deep. All 9” inside me) is how it felt when Kenny fucked me”
I fully understood in that moment that I couldn’t compete when she lodged all 9” inside my ass and used her hips to grind it inside me. I came. I came no hands and moaned like a bitch in heat into the bed sheets. I collapsed and at that point she leaned forward, strap on still buried fully in my ass, and whispered in my ear “now I’m going to really fuck you with it”. Then she pulled almost all the way out before slamming back into me. She leaned forward and put her weight on the middle of my back. Forcing me to arc my spine, pushing my ass up into the air and she started giving it to me no mercy. I felt her rearranging my ass with the mold of Kenny’s god cock. And I just screamed and moaned into the bed. Idk how long she went at it, I do know I came again.
When she finally pulled out, I could feel air on the inside of my ass. My asshole just wouldn’t or couldn’t close. I heard her giggle and say “omg, I can see inside you, I need a picture of this” and I heard the camera sound on her phone.
She asked if I was still down to fuck her tonight but I told her there was no way. Like I’d already cum multiple times and she’d blown out my back. She pouted, then told me she would make herself cum then and asked if I wanted to help. I of course said yes, not knowing what she had in mine. She went to the bathroom to wash off the strap on. Then came back and had me put it on. She rode my face as she lubed up the dildo. Then she positioned herself facing me with the head of the dildo just pushing her pussy lips apart. Then she started to work herself down onto it.
It was honestly one of the hottest things I’d ever seen. Watching her stretch herself until she got down to the base. Then she started fucking herself onto that monster cock. Like she was bouncing on it from the tip to the base. Just slamming herself down onto it. I watched as her pussy was stretched open on this dildo. Honestly I was getting hard again watching her and listening to how wet her pussy was.
Then she flipped around. I’ve always been a sucker for her ass. And from that position, god damn. Her ass looked good bouncing on that dildo. I tuned back in and started actually listening to what she was saying, “Fuck it’s so big”, “Ughhh I feel it so deep”, and more. Completely unprompted by me. She was in her own world working herself up to an orgasm while I just laid there. Finally we reached the crescendo and she just screams “Omggggg” and then she squirted. Something I’d never made her do. The strap on had the dildo just above my cock. So she squirted on my dick as she was fully impaled on this dildo mold.
Then she collapsed forward, pulling herself off the dildo as she fell. Her ass faced toward me and I could see her gaped pussy was winking at me. Then she looked back at me and said “Thanks baby, that felt so good” before getting up and wobbling to the bathroom on unsteady legs.
The following morning when I woke up she was already in the kitchen. She’d made breakfast. After we were done eating she said “I’ve got something else for you to eat” and stood up, took off her robe so she was standing naked. Then she turned around and leaned on the island before reaching back and spreading her ass “come on baby, don’t you want to fuck my ass? I want you to eat it”. So I walked over, dropped to my knees, and ate her fat ass like it was my last meal. I started fingering here and tonguing her asshole. I wanted her to cum right there and I made it happen. Then she stood up, grabbed me by my cock, and told me it was time for me to fuck her ass. Then she pulled me into the bedroom.
Words dont really describe how perfect she looked on that bed. Face down, ass up, pulling her cheeks apart, begging me to fuck her ass. I lubed my cock up and pushed in, and quickly realized I was not the first cock to be inside her ass. One more thing that another guy did to her first. All I could think about was that dildo mold ruining her ass. And I was pissed. I rage fucked her ass. And she loved every second. Kept begging for me to fuck her harder. To ruin her ass. Told me to call her a slut, a whore, to slap her ass. And I was more than happy to.
As I’m getting oh so close to cumming she starts screaming “Oh fuck, cum in my ass. Please fill my ass. I need to feel it” and that did it for me. I came harder than I could remember and filled her ass before pulling out and falling back onto the bed. I watched my cum leak from her loose asshole. Then I watched her reach back, scoop up my cum, and eat it off her fingers. Holy fuck. We didn’t leave the bed much that day. It was incredible.
And this has gotten terribly long and this is a perfect place to end.
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