Losing Virginity Stories

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Most Memorable Loss of Virginity

by csljr1j on Jun 12, 2019
First Time

I mentioned to you before that while I had eaten pussy a few times and received a blowjob once, I hadn't fucked 'properly' and was still a virgin. You had latter brought up a plan to change that last fact, and hinted it would be an exceptionally memorable way to lose my virginity. I was on my way to your place, eagerly anticipating losing my virginity to you...

Losing My Virginity at 20

by Sensual4u22 on Sep 13, 2017
First Time

Losing my virginity at 22 to a 46-year-old man I met online (100% True) I was never really interested in sex while in High School. Certain things were occurring in my life at that time that really kind of pushed it from my mind. After leaving my home to attend college all that began to change. I began having recurring fantasies about losing my virginity to...

Teacher's Aid

by Pissfan1234 on Dec 3, 2019
First Time

True story, names have been changed to respect privacy. All characters 18 years of age or older. * Memories of senior year in high school means different things to different people. Maybe the one shy introverted kid finally got the date with the one cheerleader, or maybe the unpopular girls got invited to a party at the popular girl's house. For me. though...

A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...

Scaly Butts

by Zozzon on Apr 22, 2025

The bonfire burned brightly, lighting up the entire camp as the music played. The party was in full swing as all the goers danced, ate, drank and fucked, enjoying the celebration. All of them were kobolds. All of them part of the same tribe. And all were celebrating one of their own. To anyone else, this would've looked like an orgy gone wild. But to these b...

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Video Story: Lost Virginity Leads to a Ruined Couch

by LitTV on Dec 3, 2019
First Time

Literotica is happy to introduce LitTV - a place where community members can share sexy stories in video format. Please share your opinions and suggestions for the future of LitTV. Want to share your sexy video story, erotic vlog, or hot how-to? It's easy and fun! Click here to get started. --- In this video, Alexis tells how she lost her virginity. What...

Kelly's New Experiences Ch. 6

by Develish on Aug 29, 2017
Erotic Couplings

Kelly ordered Stan to sit in her father's chair. His cock was now limp, having spent his load over Kelly's stomach. The blonde girl, now only wearing a little black thong, quickly got to her knees and began licking at Stan's cock. At the same time, she started playing with herself, getting very worked up. She expertly sucked on Stan's cock and soon his cock...

Two F***ing Years at University

by MrsJ on Sep 12, 2017
First Time

Hello, I'm Sarah. I'm a university student. A student almost at the end of her second year at university. I'm also quite sexually active - and not always from choice! I was thrilled to be accepted to university - one sited away from home, in a town that is predominantly a 'university town'. I was naïve when I enrolled - and probably still am. One of my f...

SELENA GETS ENGAGED

by Bondage4u on Apr 29, 2025

A man opens the door of a lavish, expensive, and private mansion... "sweetie I'm here where are you", "up here in the bedroom...I have a surprise for you"; The five foot nine, blue-eyed and brown-haired male heads upstairs... "a surprise for me, OH BOY" as he enters his Girlfriends-soon to be fiancées Boudoir! He sees her standi...

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Her Best Friend's Dad

by Goldeniangel on Sep 18, 2017
First Time

Author's Note: This story could arguably belong in several categories, including First Time. It's got a sexy alpha male who is much older than the young woman whose virginity he takes, so it could have gone in the Mature category. Because they know each other outside of the situation and she balks a little at first it could be considered 'reluctant' and have...