Losing Virginity Stories

65,147 results
Orientation
Length
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Infinite Scroll

Sex at School? Naturally...

by MrsJ on Jan 13, 2018
First Time

Hello, I'm delighted you're interested to learn about my high school days, which have just finished – my recollections of a young girl learning the real meaning of 'life,' discovering those innocent teenage joys of sexual pleasure, losing my virginity, and leaving school very 'sexually active.' The school I attended is a private school, hours and hours awa...

Cedar Tree Resort Ch. 03

by PrincessErin on Sep 13, 2017
Erotic Horror

"Hey Cassie we're over here." Cassie grinned and saw her two best friends sitting at the table near the floor to ceiling windows. She walked over and sat down next to Ethan. "How did you guys sleep?" Cassie looked back and forth between her two best friends and was happy when a man her age brought over eggs, sausage, and toast. She smiled up at him, but his...

How I Became A Whore‏

by woman_inside on Sep 18, 2017
Transsexuals & Crossdressers

Some time ago, a complete stranger, a man, fondled me in the subway; to my horror, my cock immediately became rock-hard. I was shocked; my response showed that I was a faggot, a slut that wanted a total stranger's cock inside me, I wanted to be fucked. I knew my virginity was his for the asking. He whispered, 'What about going to a hotel?' The thought of...

Just Couldn't Give It Up

by Heavy_Bone on Apr 17, 2019
Loving Wives

Mary Annabelle Smith is a nice normal girl. She is 27, 5'8", 160lbs, 33B and a firm butt, short curly red hair, green eyes, with a beautiful face and smile. Mary is a nice girl and loves to volunteer at the hospital and other community outreach. Mary was, all and all, the perfect innocent girl. However, Mary has a secret. A dirty secret. She loves having di...

College Girl Olivia

by SoCaliDude on Jun 25, 2019
First Time

I met Olivia in one of my college media classes. She was about 5-foot-4, long brunette hair, brown eyes, average-to slender, C-cups that she normally wore in a halter top over blue jeans shorts and sandals. Cute legs, nice ass, a typical So Cal girl. One day, I decided to ask her out. We got talking about past relationships. She guessed that I was "experien...

Peggy's Diary, Excerpt 01

by Susie_O on Sep 15, 2017
First Time

Excerpts from the Diary of Peggy Douglas In which she meets Ron and decides to ask him to take her virginity Peggy has been keeping a diary since she was 8. She started when she received a paper diary as a gift and now keeps it in encrypted text files on a thumb drive. At the time of this first entry, Peggy is 18 and starting her first full year at the loc...

Caitlin in To Rule Hell's Harems

by kmwnname on Apr 17, 2012
Science Fiction

Caitlin Forscutt to all observers, seemed to be the perfect innocent schoolgirl. Intelligent, quiet and reserved, Caitlin didn’t go out of her way to attain high-school popularity but neither was she ostracized as a loser. She didn’t go looking for male attention, but it found her anyway. For many sensitive young men, she was their first unrequited love. Cai...

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The Mandingo Society

by truedragon on Jul 20, 2015
Fetish

You are John, a young white 19-year-old guy living in a small American town. In about a month, you'll be off to college. You work in a small curios shop, run by Ms. K, a shy but attractive black woman in her fifties. She has invited to a birthday party for her son, Carl, at her house, along with a few other friends and acquaintances who work in the shop. You...

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Explorations Ch. 08

by Manny2314 on Sep 14, 2017
First Time

Three days later was the next time that Laura and I were able to be alone. Really alone. For a change it was just the two of us having sex. We had taken a long time that afternoon, getting to know every nook and cranny of each other's bodies. Heaven knows we had explored it all before, but that afternoon we really got to know them. I really loved her tits....

Mia Mahal Matriculates Ch. 01

by boo56 on Sep 16, 2017
First Time

Mia Mahal Matriculates or Lady Luscious Licks Lingam Mia Mahal, the Calipinian Princess, arrived at her Ivy League university burdened with a very full, oversized suitcase and a troublesome virginity. The airport shuttle driver, with a half-full van, had unceremoniously dropped Mia and the suitcase at the curb in front of the university administration b...