First Time Anal Stories

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First Time Anal

by bigtasty101 on Sep 19, 2017
Anal

This is a work of fiction based on real life events. All characters are over the age of 18. All characters are fiction and any likeness to real people is pure coincidence. ***** I was nervous meeting Erica for the first time. We had chatted online so I knew a bit about her. And I also had an idea what she looked like. We had agreed to meet outside a superm...

First Time Anal

by burmohini on Sep 14, 2017
Anal

One night my boyfriend came over and we were doing all the usual stuff. A little bit of missionary, I got on top, a bump or two of doggie style. All the right moves were being made because we've got that rhythm now; however, something made me decide to throw an added bonus on the table. "So... you've been saying you wanted to go back door?" I asked with sm...

First Time Anal

by pillow996 on Nov 5, 2018
Anal

I am riding my bike home from a long day at work. I'm really pumping hard working to get to the top of the hill I am climbing. I am enjoying the feeling of my legs screaming at me and the pulse of pleasure each time my asshole and taint rubs against my seat. As I turn the corner I spot two older men on the outside of their van setting up a parasail. I stop m...

First Time Anal

by pollyplummer on Mar 18, 2020
Anal

(For clarification. All events in this story occurred when both parties were 18 years old). My first real boyfriend was Kevin. He was on swim team and had the kind of body I like-- thin and strong but not bulky. He had strong Germanic features, curly dark blond hair. He treated me well, too, never cheated and always showed caring about me and my feelings. I...

First Time Anal

by SexWriter.SDK777 on Apr 29, 2025

She was always so quiet and reserved when I met her but my sometimes awkward desires would get to her even if it were something she'd already said she'd never do. I got her into oral sex with a little patience and care, and showing to her how wonderful it could feel, as well as shaving her pubes; more than her usual trimming, anyway. She's still as quiet as...

First Time Anal At A Nudist Resort

by StaceG on Sep 13, 2017
Exhibitionist & Voyeur

We'd been seeing each other for a few weeks. I'd pop round on the way home from school for a quick fuck, sometimes on your settee in the living room, other times on the stairs right in the hall. A couple of times you picked me up from school and took me on a short drive into the woods. Sometimes, if I had ten minutes and I was at home, I'd pop round and give...

First Time Anal Fuck

by xxxcutiepiexxx on Sep 16, 2017
Anal

Alice pondered her situation. She was 21 and had been dating a hot guy for a few months. He was the best fuck she'd ever had, but having said that, she wasn't all that experienced. During conversation one day it had emerged that her boyfriend, Sam, had been much more adventurous than she could have imagined: he'd been involved in group sex and even had anal...

First Time Anal by the Pool

by quietcantor on Sep 16, 2017
Anal

It was a hot day and as soon as I could finish work I headed home with the intention of having some cold drinks and lazing round the pool. I’m in my early 40s (OK, 44) and live alone with my 18 year old daughter, Suzie. My divorce was settled recently and I’ve got no plans other than seeing Suzie through university and living a comfortable uncomplicated life...

First Time Anal Online

by KeKaneAnoi on Sep 16, 2017
Anal

Before you read this, keep in mind I am typing this as my fiancé and I do it! So if my typing isn't perfect, sorry! It's a little hard to think about grammar and punctuation when you're getting fucked! And if it's not in quotations, that's because it's my thoughts and not my words. This is incredibly difficult to type. As a challenge, my fiancé asked me to...

Late Night First Time Anal

by hung_cunnilinguist on Sep 25, 2017
Anal

I met Arriana when I was dating my high school sweetheart, Natalie. I would see her every 2 months or so as she was the best friend of my girlfriend's sister. We would see each other at parties or we would all go out to dinner or bar hopping together. We would always engage in good natured flirting, which always felt safe because we both knew there was no wa...