This happened a few months ago
I stop at this gas station on my way home from work frequently and more often than not there is a chubby dark haired girl working the register. She's about 10-12 years younger than me (she's in her mid-late twenties), cute enough face, small tits for her size with a huge ass
For weeks she would talk me up in a semi-flirty way and I'd sit and talk to her for a while. One night I had worked late and was coming home later than usual and stopped in. She told me she was getting off in twenty minutes and I made a lame joke about knowing she was going to "get off" which she laughed way too hard at. We ended up hooking up that night at her apartment.Things went great, we both had fun. She called me "daddy" a few times which I didn't love but she seemed to get off from it
She bugged me a few more times about hooking up again but I never had time around her schedule. A few weeks later I stopped in and she had a friend she was talking to. I wasn't trying to listen in but at one point I heaed her tell her friend "I don't do anal, it's fucking humiliating". I kind of laughed to myself taking that as personal challenge
Fast forward a few weeks later, I stopped in again later than usual. We talked for a bit and she made the comment she was getting off in a few minutes and that I should come over and smoke with her. We get to her place and I barely get through the door before her hands are all over me so we immediately got to business. At one point I am behind her fucking her doggystyle watching her huge ass bounce off me, catching winks of her dark asshole. I was wearing a condom and she suggested I take it off. Something clicked in me and I responded "the only way it's coming off is if I go up your ass" and she immediately replied "no way I don't do anal anymore" in an actual pleasant voice. I pushed a bit further and said "you're just embarrassed because your ass is too dirty for it"....she was actually somewhat offended by this. "My ass is not dirty!". I told her to prove it. She said fine go ahead but to be somewhat gentle at least
So I took the condom off and spit on her asshole and slowly rubbed my head on it and started to push in. She actually moaned and didn't pull away. "Mmm you like this don't you?" I said.."no....it's not bad" she said. After a few more minutes I was pulling almost all the way out and slowly pushing back in, I decided to throw some dirty talk in "you like getting your tight dirty sh!thole fucked don't you?"
She bucked into it and started rubbing her pussy "yes daddy, push my sh!t in!" She gasped. This girl had a filthy mouth once she got going. She came several times all of them gushing squirting orgasms and I blasted an absolutely massive load up her ass. We have hooked up twice more since but that was by far my favorite time
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