About: "It began as my friend trying to get me to lose it with her boyfriend Then it turned into something else"

Title: Losing It


Dana was mature. Very mature. She had huge breasts, a D I would say, and she was only 18. She was hot too. Dana had had sex with about ten guys. I on the other hand was a B cute but not HOT. I had told her that I wanted to lose it, but I couldn't find a good enough guy. So we went on a feild trip up in the mountains. We stayed in a very nice hotel. Dana and i shared a room. So that night before we went to bed she brought up the subject on sex. She talked on and on about how good it felt. before I knew it I was fingering myself under my covers. Then we went to bed.

It was about 2am when she woke me up. "You said you wanted to lose it, right" she said, "Here's your chance," she pointed to Brett her boyfriend. he was sitting on her bed in his boxers. I got up. Did she really want me to have sex with him. I looked at her confused. "Go ahead. It's fine. This is what friends are for." She got off the bed and Brett came over.

At first we were making out. The he slid his hand up my shirt. I was wearing a tank top and underwear. Her fingered around with my nipples. The he took my shirt off. He my upper body and it fealt good. The part that got scary is when he pulled a condom out. Slowly he pulled down his boxers;I helped. Then he took off my underwear. I was so scared.

He began to put his penis into my vagina. It was huge. He saw my eyes expand."It's OK" he said. The he pushed in. It hurt so badly. He got deeper and deeper. I started to cry. Dana was on her bed watching." It's O.K" she told me, "Brett, let her be on top" she said He got off then Laid on the bed. His dick stuck up high. I looked at Dana for advice. "Sit on it" she said. I did; it still hurt.Then Brett took completly over. He Fingered me, well actually "Fisted me" Then sucked my pussy. After he was done he left the room and went bakc to his. Dana looked at me in disapointment.

The next night he came bakc this time Dana said she would help. He anal fucked her while she fucked my pussy. It fealt really good. The next night brett got caught. So it was just me and Dana. I decide to go to bed because I wasn't "lesbian"

At 12am she woke me up. I was completely naked and so was she. She was silently fingering me.I got up and she looked startled and hurt at the same time. I said that i would much more like it if i was awake too. Then she began to kiss me. She moved down and scukced on em again. We did that and played with eachother for about an hour. Then she got up. i thougt she was done. Dana went to her sucase and got out a plastic dick. It was about the size of Brett's. She used it on me but it fealt good this time. I went into orgasim about five time that night. Now we meet up every now and agian and do it. Dana is married, but it doesn't stop her. Me on the other hand am scarred by Brett and never had sex with a guy again. I'm strictly On girls.


Comment on This Story

Provide feedback on this story for the author. All comments are moderated before appearing below. Please use courtesy and common sense when commenting. We do not accept discussions refering to beasitality, rape, or reference to underage characters.


Rate this Story

★ ★ ★ ★ ★ ★ ★ ★ ★ ★  "Losing It"
Current Rating: 0 out of 5 from 0 votes
- Click a star to rate ☆ ☆ ☆ ☆ ☆ ★ ★ ★ ★ ★ 



Special! For Our Readers: Live Full Screen Genuine 100% FREE Webcam Show - Girls, Guys, Straight, Gay and Lesbian.

Other Stories From Our First time sex story Category:



  • My First Man Experience - He pulled away from me and I am standing there naked with my cock standing straight up completely disoriented wondering what was to come... This Story was published on Aug 19, 2014 and is from the SexTails First time sex story section. Story written by Ray.
  • Virgin College Student No More - I was changing from a heterosexual to a bisexual even though I was still technically a virgin and the closest I had ever come to sex was an inordinate amount of masturbation... This Story was published on Dec 6, 2013 and is from the SexTails First time sex story section. Story written by Tommy Tudor.
  • A Very Special Birthday - My boyfriend said he had a special birthday present for me at his house. There he carried out a well executed seduction... This Story was published on Jun 25, 2012 and is from the SexTails First time sex story section. Story written by .
  • Honeymoon Instruction - My bride and I were virgins on our wedding night when we could not consummate our marriage a mysterious stranger taught us how to make love... This Story was published on Jan 27, 2012 and is from the SexTails First time sex story section. Story written by Recipient.
  • How I Lost My Innocence in June's Bed - Young man loses his virginity to older married woman who enjoys plenty of sex... This Story was published on Jan 24, 2012 and is from the SexTails First time sex story section. Story written by Dave.
  • Archbishops Opportunity - He was going to see a womans bra and boobs and cleavage for the first time in his life... This Story was published on Oct 30, 2010 and is from the SexTails First time sex story section. Story written by StonyPoint.
  • Princess Virgin - You have some of the most incredibly sexy thighs a woman ever could have... This Story was published on Oct 28, 2010 and is from the SexTails First time sex story section. Story written by StonyPoint.
  • First Time was at Mardi Gras - Since she had not orgamsed yet he said she was calling for me to get up there and lick her to orgasm.... This Story was published on May 23, 2010 and is from the SexTails First time sex story section. Story written by luvstoshare.

Read Our Latest Stories:



  • Captain Garth Clint: Sex Slave in the Outback! - Part 3 - This is the third chapter of the erotic story involving Captain Garth Clint in the Outback... This Story was published on Sep 14, 2014 and is from the SexTails Erotic Stories section. Story written by Adelbert.
  • Thirty One Days - Chapter 23 - This is the 23rd chapter of the sexy story Thirty One Days, a challenge that involves sex, thirty-one women, and will take 31 days... This Story was published on Sep 10, 2014 and is from the SexTails Sex Story Series section. Story written by Ronan Jackson Jefferson.
  • My Bi-Sexual Road Trip - Chapters 23 - 25 - That afternoon I had my chance at her big brown hole and I got Jen kneeling on the bed I fucked her pussy for a while making my cock nice and wet with her cum... This Story was published on Sep 10, 2014 and is from the SexTails Sex Story Series section. Story written by Deepprobsix.
  • Cock Worshipper - PART 5 - The night I first hooked up with a posh lad called David Hetherington who let me worship his cock before pushing my face lower down and between his legs... This Story was published on Sep 10, 2014 and is from the SexTails Gay erotic stories section. Story written by Jason Kason.
  • Captain Garth Clint: Sex Slave in the Outback! - Part 2 - The second installment of the erotic tale involving Captain Garth Clint in the Outback... This Story was published on Sep 7, 2014 and is from the SexTails Erotic Stories section. Story written by Adelbert.
  • Doubling Up - Chapter 2 - My son and I discuss how we can use a double-ended dildo together without compromising our close relationship... This Story was published on Sep 7, 2014 and is from the SexTails Gay erotic stories section. Story written by Robert Furlong.
  • Captain Garth Clint: Sex Slave in the Outback! - Part 1 - In this erotic story Captain Garth Clint returns in his sexual adventures, this time he is in the Outback... This Story was published on Sep 3, 2014 and is from the SexTails Erotic Stories section. Story written by Adelbert.
  • My Bi-Sexual Road Trip - Chapter 21 - 22 - I finished fucking her from the rear and I finger fucked her arse while fucking her cunt... This Story was published on Sep 3, 2014 and is from the SexTails Sex Story Series section. Story written by Deepprobsix.
Link to This Erotic Sex Story Titled: "Losing It"
NOTE: Sextails.com contains erotic sex stories, do not read the tales if they will offend you or cause you to break local laws. By following any links you declare you are not a minor, or in the company of a minor, and entitled to access material intended for mature responsible members of society capable of making decisions about the erotica they read. All characters and terms in any story on this web site refer to persons age 18 and over.