Losing Virginity Stories

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Kerri's Descent Ch. 03

by Honey_Bee_16 on Sep 12, 2017
First Time

The weeks had flown by after I discovered how much I really liked spending "quality time" with my roommate Jessie. We had gotten into a routine. After class each day, we'd eat dinner together in the dining hall, go upstairs, do some homework, watch TV together, and then go to bed early to fool around for at least an hour or so. I had started to see Jessie as...

Losing My Virginity

by *Snatch on Aug 31, 2017
Humor & Satire

It took a lot of hard work and effort on my part, to lose my virginity. Well, not really...but it did take awhile! When I turned 18, I decided I was going to be de-virginized, one way or another. All through High School, I listened to other girls talk about sex, sex, sex. It seemed like everyone was fucking except for me! My boyfriend graduated a couple of...

It's My Brother's Fault

by alicia70 on Sep 2, 2017
Erotic Couplings

The summer before my freshman year in college I was looking for something in my older brother's room when discovered his stash of dirty girlie magazines and erotica. Some of the erotica were books and the ones that piqued my curiousity were about being submissive. As he was away for the summer, I took the three paperbacks into my room and started reading. I...

From Family Man to Bottom Bitch Ch. 02

by esclaro on May 18, 2020
Transgender & Crossdressers

In the years following my virtual encounters with Isabel, I felt driven to explore my attraction to transgender women. After seeing her and talking to her over the years, I knew that I would never be fulfilled sexually until I could realize my deepest desires. Desires which I never even knew that I had but which were now obvious and undeniable. What were t...

The Night

by KarennaC on Sep 17, 2017
First Time

It was "the night". Brock and I had talked a few times about sex. Well, maybe more than a few. A friend of a friend, Brock knew more about me than I was totally comfortable with, including the fact that at age twenty I was still a virgin. Brock had decided he wanted to be the one to change my status. A big part of the reason for my overdue loss of virgini...

My Indian Soulmate

by swollenbell on Sep 14, 2017
Interracial Love

I grew up in the outskirts on a medium sized city in the UK. We weren't poor or rich, just a solidly middle class English family. Education was really important to my parents and my sister and I both went to a local Grammar school (what would be called a magnet school in the US). One of my sister's friends was a beautiful Indian girl called Preeya. She had a...

Two Lovers' First Time

by SouthernWomenLover on Aug 30, 2017
First Time

(This is my second attempt at writing a Literotica story, this one, like the first, is based on a true story but has exaggerated events. This also serves as a pick-up from where I left off with the first story. I ask that you please read my first story before you read this one - It is titled Two Lovers' First Anal. It is a prelude to this, and can be found b...

Percy Jackson, cumdump of the hunt

by Emi on Jun 13, 2019
Transsexual

In this story, all the hunters are older than 18. "Sorry Seaweed brain, but I think we should end this relationship here." It all begun with this simple phrase, she never told him why she wanted to dump him, she just did. When he asked why, she just said that he wouldn't understand before leaving like that, like everything they've been through didn...

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Catelyn's Corruption

by NerdyRosie010109 on Jul 15, 2020
Anal

Catelyn leaned her head back onto Gabe's shoulder, snuggling closer to her boyfriend under the fuzzy blanket. A reality show was playing as the couple cuddled on the couch, enjoying the quiet Friday evening. Gabe's roommates were out at a concert, so he had taken advantage of the empty house and invited his girlfriend over. Catelyn was a junior journalism s...

Momdom a sissy son's wish

by Viking973 on Jun 20, 2020
Transsexual

Intro: You never had much luck with the girls in high school. You had a few girlfriends early in high school but the last 2 years before college was rough. It had come and gone, you enjoyed it, you weren't an outsider and had many friend groups but you never went out to parties or out of school to meet up with friends. You enjoyed video games and porn too mu...

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