The first and last time I [M] did anal [F]

So just some backstory, if you want the action, skip to the dashed line

This was in 2019 when I [21 at the time] was a senior in college and it was the first time I had my own room on campus. My roommates were all seniors, one of them being a guy I knew girls found especially creepy, one who was super quiet and nice, a real lad. The other worked for the school but was laid back and let us drink in the dorms, bend rules, etc.

At this point I had a summer fling stay on campus once or twice and a friend from another campus who was definitely a r/nicegirl but what’s important is this new girl I met after getting out of a late class. I only had been at this campus a year prior and my summer fling told me she was moving to Tennessee so I was looking for some new girl to be with.

I went to the coffee house around 7pm and I could tell she was new. A bit nervous and giggly, about 5’6, long brown hair,skinny, pasty and had freckles. Nothing special although I was feeling flirty and she seemed nice. For reference I’m 5’10, slim athletic build, lightskinned, short light brown hair. I ended up leaving her my number so she could message me if she wanted and if not it’s no big deal.

I get back to my room and she asked me if I was from a certain area because of my number and she actually lived pretty close, so we talked about that then I joked about having her come over and bringing a change of clothes, and she showed up. Change of clothes, her bag for her morning classes and a smile. We sat on my bed, shared poetry, and talked awhile before the tension finally broke and we were all over eachother

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I pulled her onto my lap and started kissing her neck before taking off her shirt then mine, quickly taking off her bra to play with her tits. They were 32C, had pink nipples and also covered in freckles, which I honestly liked.
I sucked and licked on them while she moaned and kept grinding into me before I picked her up and pushed her against the wall to undo my pants and she pushed me back onto the bed while stripping.

She gets down and starts sucking my dick [7 inches, thick], really trying to go as deep as possible as I hold her hair back, making eye contact and moaning before I pull her up and onto the bed, spreading her legs to eat her out and right before I start, she asks me to turn off the lights [this is important later]. I oblige and start eating her out grabbing her ass, realizing she had pretty wide hips for a skinny girl which made me eat her out much more enthusiastically.

I wanted to make her cum that way but she started to moan “Fuck me, please!” So I grabbed a condom and teased her clit as I rolled it down with my free hand, having her ass right off the bed and her legs on my shoulders before I slid it inside of her. I started going to town and we both were getting a bit loud.

I switch her around and get her on her knees with her ass in the air, I put one leg on the bed to get a deep angle and keep going, then i feel her reach back and stop me. I ask if shes okay and she asked if I wanted to do anal. Before this I always turned it down. I never saw the appeal but I knew how it went from second hand accounts or porn. So I said sure and realized I had lube in my dresser.

I massage her asshole and apply some and generously apply with to the head of my dick and my shaft before I assume the as position as before and go slowly. I feel the tips of her fingers brush against my balls as she plays with her pussy and I couldnt help but to pull out completely and slam my dick into her, feeling her nails against my balls sent shivers down my spine. She either was in heaven because she only got more rough with her clit as I smacked her ass and kept ramming her until I came ropes into her ass.

Here’s why this was the last time I did anal

I knew she got off at that point so I decided to pull out, so I pull out slowly and realize that a good amount of shit is coming out. I decided to grab the shirt I was wearing and put it under her while I pulled out and told her it was just a lot of cum. She actually believed me and since it was dark she couldn’t see for herself. I kept quiet and wiped my dick off with the remainder of the shirt, put it in 2 bags and tied them up tight so the smell wouldnt get out. It was a school shirt I got that semester so I wasn’t worried, and I ended up getting a good laugh out of it when I told my best friend later because he always bragged about how great anal is.

I ended up asking my one roommate for a new shirt and I just told him the other one caught on a door and tore, but I feel like he had some idea that it was due to another reason.

This girl ended up being a bit unpredictable and started showing up at my place unannounced a lot to come over and all so I cut her off and she ended up sleeping with my creepy roommate to get my attention. Later I found out she had a boyfriend back at home and the creepy guy still didn’t care until she broke his heart.

All I can say is that shirt got a nice funeral in the school dumpster, a fallen soldier I’ll always honor who died in the line of duty

Source: reddit.com/r/gonewildstories/comments/kh8411/the_first_and_last_time_i_m_did_anal_f