Losing Virginity Stories

65,147 results
Orientation
Length
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Infinite Scroll

Who Is Ch. 03

by CatRun on Sep 16, 2017
Novels and Novellas

So you really have never had sex before that point? Correct. But look at you. You're gorgeous. And you're smart and you're... you're the whole package. So I've been told. How could you not have had sex like a thousand times before that day? I guess that's what happens when you get hurt. Plus, I was young and inexperienced. Who was your first time with?...

Why I Liked School Ch. 1

by freedom666 on Sep 19, 2017
Group Sex

Anna lay with her legs open. God she was wet. I moved forward, and positioned myself between her legs. She was begging me to take her. I rubbed my head around her entrance, while at the same time massaging her legs (she has great legs, and I have always had a soft spot for great legs!). Finally I was ready. I thrust my cock inside Anna. I couldn’t believe my...

Boat Girl

by XXscribbler on Jul 4, 2018
First Time

"Would you like to kiss me, Doctor K?" The question came out of the blue, and nearly unmanned him. The asker, Danielle, was by far the most beautiful girl he'd ever seen -- and he'd seen a lot in his time. Her Mom was full-blooded first generation Chinese, her father plain mongrel American White Boy. Danielle had turned eighteen a few weeks ago, at sea. T...

A Virgin Trans Girl's Mission

by thehuntsman-king on Aug 24, 2020
Transsexual

On many levels, Eleanor was very proud of herself. She had just graduated high school, with a strong GPA and class ranking, a partial scholarship to a good university and several extracurriculars. She'd done this while figuring out her gender identity, figuring out coming out and hormones and all the other often embarrassing and difficult details that came w...

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Keeping My Scholarships

by SouthenDaisyBelle on Sep 14, 2017
First Time

I twisted a strand of my long, neon red hair through my fingers as I waited for class to end. The curl bounced back into place as I released it. The professor droned on and on about economics and our upcoming final, but all I could think about was the minute hand ticking by slowly. I crossed my legs and tugged at my short red leather skirt, attempting to hid...

Who I Am Ch. 06

by AngelSand on Sep 14, 2017
Novels and Novellas

Hello There! I am so so so very sorry that I have been gone for so long. I know I may have lost some of you, but I intend to earn you back as quickly as I can. I humbly present to you the last chapter of -Who I Am. To fully understand this story, I suggest you start with chapter 1. For those of you who are enjoying Karen's story, this is not the end. I h...

Life's Dream

by shy_boy on Aug 31, 2017
Erotic Couplings

Jane came home this weekend. I’d had a crush on her for as long as I could remember. Back in grade six, when erotic thoughts first started to cross my mind, she was my first sexual fantasy. I used to sit in class and dream that I was on top of her, my penis buried deep inside her, pumping madly at her waiting vagina. Of course, at the time I didn’t realize...

The Whore of Babylon

by JSmith82 on Sep 17, 2017
Loving Wives

Episode 1: From virgin to cheating slut Chapter 1: Losing my virginity Where did it all begin? Where did I start my career? How did I go from a sweet college eighteen year old to being a professional girl and a Madam? Ah, the memories!! Let's start at the beginning. My real (married) name is Jennifer Harrison and I was eighteen and a very nice clean gir...

Clutz

by KarennaC on Sep 14, 2017
Humor & Satire

My name is Karenna, and I'm a clutz. I've been a clutz since I was a child. I fell so frequently my knees still bear the scars. After a while, my parents learned to ignore the thumps unless I started to cry. Which was seldom; I was usually too busy laughing at myself. My first French kiss, I couldn't figure out how to get my teeth out of the way. Poor guy'...

Halloween Deception

by NymphWriter on Sep 13, 2017
First Time

Why is it when people share stories about losing their virginity, it sounds like a fucking fairy tale? If you just dig a little deeper and you learn the truth is nowhere near close. Oh, and don't get me started on the bullshit stories people write about how when a girl is deflowered by the man of her dreams, making it sound like a loving gesture of passion a...