Losing Virginity Stories

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Colourful Socks

by ILikeThighHighs on Dec 24, 2019
First Time

I knew I wanted to lose my virginity to an older man and I knew that I didn't want him to be gentle. I had a boyfriend when I was 15/16 - didn't enjoy the drama he came with. He was 3 years older than me. I then dated a man who was 25 years my senior when I was 18. I didn't lose my virginity to him, but that's another story. Late last year, I was in the pr...

Will I Regret It?

by TooTiredToCare on Sep 16, 2017
First Time

We were lying on his bed again. We were both over 18, but just barely. I was still very young. A great big bed, so comfortable, so lovely. We were "hanging out" before a party. I mean, that's what our parents thought. He was playing the music loud so anyone around couldn't hear my moans. A fast paced alternative rock. I was so used to hearing this when we...

Diary of a Slut: Losing Virginity

by SltCarly427 on Jun 9, 2020
First Time

You never forget your first time, no matter how good—or bad—it was. And even though mine was only a few months ago, and everything is still fresh in my mind, I don't think I'll ever not be able to remember every single detail. It was both an incredible experience and a horrible one at the same time, and a total accident. I never planned on losing my virgin...

Casanova Redux Ch. 16

by velvetpie on Sep 15, 2017
Non-Erotic

We were safe. When I showed Shakey the coin from Prince Brenton, he shouted so loudly that birds left the surrounding trees. I didn't offer any explanation; I simply walked over to where Withers knelt, steeling myself against the tears in his eyes and sliced through his rope bonds with a knife I found nearby. Shakey tried to protest losing his prisoners but...

My Step-mom Millie

by rumppumper on Feb 17, 2016
MILF

"Matt!" I hear someone shout from the crowd of people waiting at the exit to the airport. I look towards the direction of the sound, and I see a blonde woman in her mid-40s, short hair, and in a tight white top smiling at me and waving, and I recognise my step-mom Millie Smith. I smile back and wave, and walk towards her, pushing my luggage cart in...

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Darkman Cumeth

by humminbrd30 on Aug 18, 2017
First Time

Chris can look back and remember how it felt to lose her virginity. She was 18 years old and just decided that the next man that asked her for sex would get what he wanted. He was a total stranger; Chris didn't even know his real name. He called himself Darkman. Chris just felt like it was time to feel what all the fuss was about. Chris and her friend were...

You Mustn't Do That!

by Svenskaflicka on Sep 16, 2017
Anal

“You mustn’t! I’m not allowed to!” “Oh, come on, Fatima…” “No! I must be a virgin on my wedding night, or I’ll embarrass my whole family!” “OK, OK…” Dean sat up, horny and frustrated. Fatima put a hand on his naked shoulder. “Dean, I love you,” she whispered. “But I must save my virginity until I get married.” “I thought your family was modern.” “They...

Game People Play

by Ashson on Sep 12, 2017
First Time

Games People Play : The Start. They were all of age and all still virgins. The girls were virginal, that is. The selected men were also all of age but the girls had not actually inquired as to their virginal status, as they didn't really think it relevant to what they had planned. A little quiet negotiation had been going on for a while. The four girls want...

Cumming to Terms with Her Pt. 01

by contactsteph77 on Sep 4, 2018
Transsexuals & Crossdressers

My first experience of anal intercourse was a pretty traumatic one. I had been dating my girlfriend for about 6 months, and we had yet to consummate our relationship. Being a horny 21 year old man I was gagging for it. Don't get me wrong we had fooled around with oral play, and mutual masturbation. But I was 21 and still a virgin; the term "Blue Balls" did...

Vendetta

by RexEatapuss on Sep 17, 2017
Celebrities & Fan Fiction

This is a true story, I swear, up to a certain point. It then becomes a fantasy of what may have happened, had things continued. Conversations are repeated as closely as I can remember them. Some names and locations have been changed to protect the guilty. ---------------------------------------------------------- I love my wife, but due to various reason...