This was in the second year at college. When we came back to campus, we both had moved out of the dorms. Samantha (read my stories before) ended up with a beautiful one bedroom with tons of space and I was living with a few friends in a tight spot further away from school. She came from considerable wealth while I was skating by on a mix of student loans and savings from my hourly jobs the summer before.
We hadn’t really connected over the break, but when we showed back up we picked back up as friends. And to my delight, she was the one to late night text me on the weekends to hookup. And it became a regular thing of quietly sneaking off from my friends at the end of the night to go finish the night at her house.
This particular story happened in the morning after a long night of fucking. I woke up spoon Samantha our legs intertwined, solid headache from going out late, with raging morning wood pressed up to her ass. I start going for my standard move of rubbing my throbbing cock up and down her pussy while she is just starting to wake. I slide right in since she is still slippery and sticky from the cum I’d left there a few hours before. We rock back and forth slowly waking up to the sunrise.
It was pretty slippery and from the side angle I ended up sliding out as we were moving. We repositioned to come back in, her shifting around and while I pushed. It was either her devious plan or just the mix of being relaxed and very lubed from all of our sex that when I went to push back in it was hard to slide in and her eyes lt up with surprise. Not thinking much and being in a wake up fog, I pushed harder and she let out a yelp!
We both look at each other and I realize I’m not in her pussy anymore but 2 inches in her ass. Now while I played with her ass while we had been in doggy on occasion. I’m pretty sure (based on her face) no one had been in her ass, and I’d never experienced it with a girl before. She looked at me with an expression of pain, submission and “well you are already back there” and pushed her ass further back.
Samantha was one always willing to try new things and apparently this accident was one of them. We went slow and I never really pushed past 4 inches. We stayed in our spoon position while she rubbed her pussy faster and faster. I think prefer PIV but when she orgasmed from rubbing her clit, she clenched down on me in her ass and I instantly came sending a large load into her ass.
I pulled out slowly “saying wow I didn’t expect that, I can’t believe I came in your ass”. To which she responded, “I know, but it was worth the experience”. At the point, I get out of bed to go clean up and I get a beautiful view of her leaking from her ass with a glistening pussy that I had filled the night before.
Source: reddit.com/r/gonewildstories/comments/wtwcmq/mf_accidental_anal
Great story! She sounds like a fun girl!
Are y’all still dating? How long ago was it?
Did y’all do anal more regularly after?
Thanks for sharing
Good girl for letting you keep going
I agree with you about preferring vaginal sex over anal but there’s something very hot about anal that still makes me want to experience it every once in a while