Oct 122015
 

I graduated from high school in May of this year. Four of my best friends and I celebrated by taking a trip to the beach, Before we left the converstaion of sex came up. I was the only one that had remained a virgin so they told me they thought it would be a good time to “loose it’ because they all expected to get laid on the trip. Before the trip we amde a run to the drugstore and purchased condoms. Once we were at the beach it didn’t take long for guys to start hitting on all of us and by the second day we all had a guy friend. The next evening we all ended up in our rooms drinking. It didn’t take long for the friend I was rooming with to hit the bedroom. The guy I was with finally made his move by first playing with my tits then getting his hand in my pants. I had gone that far before but he quickly got me far more excited than I had ever been. He had unbuttoned my shorts to get his hand down them so when he unzipped them and layed me down on the sofa I didn’t resist. Off came my shorts and panties so I knew I was going to loose my virginity. I ask if he had a condom to which he said yes and got it out and put it on. He had gotten me so wet that he had no problem taking my prize quickly. I was so excited that I didn’t realized each time he went deep I was letting out a loud sigh. The next thing I know I hear my friend say “Go girl…see what you’ve been missing?” Then I could feel the guy throbbing inside me and I let out a with “ohhh yeah!!!” as I had my first real orgasm. When he had finally stopped comming he pulled out and said “Good luck..hope you don’t get pregnant…the condom broke.” When I ask why he hadn’t stopped he said I was enjoying it so much he figured if he came in me I would really like it….which I did. I freaked because I knew it was a bad time of the month for him to have come in me. Of course, that spoiled the rest of the trip for me. I was a nervous wreck for the next couple of weeks but I started right on time when my period was due.

 

 

  • Name: Renee G
  • Gender: Female
  • Age of Virginity Loss: 18
  • Current Age: 18
  • How would you categorize your story?: Regret
  • Country: USA
Oct 122015
 

Really bad title aside, I dated this girl who was a horseback rider, and was also two years older than I was, which makes her 17 in this story. I don’t wanna slut shame, so I will just say she’s been around, and when we met she was far from pure. I thought she was cute, so we tried dating. Things escalated really quickly, to the point where I pleasured her only a few weeks in, but no sex yet. I wanted to wait, since I was only a freshman and didn’t want to rush. Too bad that didn’t work. My penis did the thinking, she had a nice body which told me to just do it. I bought condoms, and we planned when and where it would happen.

Fast forward, and we’re alone, in the woods of all places. I try to put on a condom for the first time, screwing up and slipping from nervousness, which frustrates her, to my surprise at the time. Once it’s on, I decide to take charge and be on top, and I go in. So the pain begins. Seeing as this girl rode horses, she was a bit stretched out, so not very much pleasure was had on my end. Mind you, I don’t really have a very large package, and I’ll admit that, so that didn’t resonate with her large chasm-vag. This is why I lasted almost an hour combined, since I faked an orgasm the first time we did it that day just to get a break from thrusting. It tuckerwd me out. Second time, which doesn’t really count as losing my virginity so it’s gone now, she was on top a lot, and I freaked out because she started bleeding. She said it wasn’t her time of the month, but there went a good condom, to waste. I wasn’t prepared to see blood, or really for sex at all. We did end up doing it again two more times another day, and only the fourth time I orgasmed for real. I labeled this story as regret, simply because I wish I had waited. I’m not friends with this girl anymore, and I don’t feel like I gained anything except for this one piece of knowledge; I seem to be manipulated by my dick really easily. Don’t fuck around like an idiot, kiddies.

  • Gender: Male
  • Age of Virginity Loss: 15
  • Current Age: 16
  • How would you categorize your story?: Regret
  • Country: USA
Aug 092015
 

It was with myself and this girl I was dating at the time. It was early October and we were visiting my grandparents while they were camping with their horses. Myself, Emily and my sister were hanging out at a park in the camp grounds. My sister had to pee, so she ran off. It left myself and Emily together. We decided to sneak off. We headed from the park to a trail. We walked about 30 minutes and stopped when we found a blocked trail. We followed the blocked trail for another 5 minutes. When we stopped, she pulled out a lighter and a joint. We both smoked one and were pretty high. (I don’t condone drugs! They’re bad, mkay?) We rested on a fallen tree and started making out.We were both getting turned on. It was electric! I was hard, and she was turned on. She looked at me and asked “Ryan, dear? I’m ready.” I blinked and choked on my spit! She could have meant anything! I nodded and agreed. I pulled her pants down and really didn’t acknowledge her privates (I’ve seen them already, numerous times.) She pulled mine down and started sucking me off. She sucked me off for about 20 minutes when she oooked into my eyes and smiled. I smiled back, unbeknownst to her, I was very nervous! She bent over the tree we were sitting on and spread herself open. I closed the distance between us. I tried putting it in, but was pushing into the wrong hole (whoops!!). She had to grab me and point me to her pussy. When I felt her lips around my head, I was getting “that feeling”. You know, the feeling you get when you’re about to cum. I started going to town in her. It was only 20 seconds long. The finish was, less than desired. I regret it, tbh. It was the worst sex I’ve had, ever.

  • Name: Ryan
  • Gender: Male
  • Age of Virginity Loss: 14
  • Current Age: 18
  • How would you categorize your story?: Regret
  • Country: USA

 

Jul 112015
 

So I was seeing this guy since last summer and at first it wasn’t serious. Couple months passed and he began to express his feelings for me, he presented me to his parents, we were only seeing each other. I was a virgin and he wasn’t. He had MULTIPLE partners back then , but with me he didn’t mind to wait because it was different. The last time a went to his house was the time I lost my V CARD. We were watching Netflix on his bed and we kissed and everithing as usual. When it was time to pass the act I asked him if he gonna put a condom on and his answer was: oh so you want me to put one on? in my head I thought that not because I was clean that he was also , even if I trusted him. So he starts to penetrate and as he does he goes faster and deeper. It hurted like hell . Then he turned me into positions and gave me head. He looked at me with eyes I never saw before. At the end he just stopped and laughed with me I dont even know why. After that day , I learned from a dude that he fucked a girl a week before me . Now he wants me back . Fuckboy.

  • Gender: Female
  • Age of Virginity Loss: 17
  • Current Age: 18
  • How would you categorize your story?: Regret
  • Country: States
Jul 112015
 

I had previously dated a girl, Samantha, and we had broken up before our relationship got too serious. It was a year later when we went for coffee, and a walk afterwards and found ourselves making out in a park. We both went home and agreed to meet up later in the week. She came over to my house, my mom was out for the night and we had the place to ourselves. As soon as Sam came over we began making out heavily on the couch and that’s when I decided to take her to my bedroom. We started making out in the bed and soon our clothes were coming off. She had lost her virginity the year before in a quick fling, and told me later that she couldn’t wait to get with me that night.

She was still in her bra and panties when she pushed me down on the bed and un-zipped my pants and took me directly into her mouth. I had never been so hard and she looked into my eyes and told me that my dick was perfect (with this cute look of fascination on her face as she held it in her hand – I was in heaven) Then she hopped on top of me and slid me all the way in. She slid up and down maybe twice before she just stopped and I could feel all of her muscles tighten around me. She continued to slide up and down while sitting straight up (so hot!) she moved slowly on me for a few more minutes clearly working to climax and we sped up until she just stopped with me deep in her.

It suddenly felt like somebody poured a pitcher of water on me. She had an amazed/happy look of joy mixed with shock as she came.Neither of us were sure what had happened (did I cum?!) until she looked at me and said ‘I think you just made me squirt… A lot!’ She had never done this before. She went down on me again and told me it tasted sweet. She began licking me all over as if she wanted it all. Then I moved around and took her on her knees. There was a mirror to the left of us and we both watched as I made her cum again. I continued slowly for a bit longer and asked her where she wanted me to cum (not wanting to surprise her) and she replied ‘anywhere you like’ and those were the magic words because I immediately pulled out and came over her ass and back. She moaned again as if it gave her more satisfaction and said how warm it felt.

Before moving, she wiped some of my cum up with her fingers and put it in her mouth smiling at me. It was and still might have been the hottest look a girl ever gave me. It was so hot that I slid inside her again and whipped up the rest with my fingers and held them in her mouth for a moment. From then we fucked like rabbits for a few years. And that’s how I lost my virginity! (We hooked up a few times years later and she tried to squirt again from being on top or any other way. She said that was the only time she had ever squirted. And it was my first time!

  • Name: Jake
  • Gender: Male
  • Age of Virginity Loss: 17
  • Current Age: 28
  • How would you categorize your story?: Awesome
  • Country: Canada
May 172015
 

It was 3 months ago. The guy was my crush.I stupidly promised him a blowjob for his birthday. Once his birthday came ,me ,him and all our friends were hanging out. He took me to a porta pottie, but I didn’t want to because I knew he was gonna ignore me forever afterwards, I didn’t say anything because I was too scared to.  He caressed my cheek and I gave in once he was done. I swallowed his cum. Then when he finished,  we walked back to our friends. 3 months after he consumes my thoughts. I think I love him but I don’t want to.

  • Gender: Female
  • Age of Virginity Loss: 14
  • Current Age: 14
  • How would you categorize your story?: Regret
  • Country: USA
May 032015
 

Soo here’s how it goes. His name was Erin he followed me on Instagram and back and forth we’d like each others pictures until one day he messaged me. We started texting and flirting later on one day he asked when we would chill so I said whenever with no intentions of having sex with him at that point and I stupidly agreed to hanging out with him at 2 am. That night was pretty much crap , not as good as people make it out to be, his wang was ridiculously big so it hurt also. Me being the paranoid person I am I thought I was pregnant (it being my first time) thankfully I wasn’t. I don’t so much regret it because of all the things told to me by my religion but I do regret it to the fact that it meant nothing to me with somewhere who was basically a stranger to me.

  • Gender: Female
  • Age of Virginity Loss: 17
  • Current Age: 18
  • Story Title: Stupid decisions
  • How would you categorize your story?: Stranger
  • Country: USA
May 032015
 

I had only been with my boyfriend for 2 months but he was ready to have sex. I went to his house thinking that we would “chill” but things escalated. Somehow he managed to get me naked, and he was sucking my breasts while fingering me. He finally tried to put his dick in. It took a while because it was really tight and I kept asking him to stop due to the unbearable pain. He finally broke the cervix and I started bleeding and crying. I asked him to stop at that point and he did. I didn’t even realize it was without a condom. I regret losing it to him because he cheated on me a few weeks later.

  • Name: Anonymous
  • Gender: Female
  • Age of Virginity Loss: 15
  • Current Age: 15
  • How would you categorize your story?: Regret
  • Country: Usa
Mar 232015
 

I went back with my ex bf, and he started talking about how he would love to fuck because he was a virgin but I lied and told him that I wasn’t, well 2 weeks after I went back with him I ended up having sex with him, during the sex I was having a bad pain cause it was the first time and after he came he got hard again so we fucked again and the same pain and after the sex I was just laying there holding him and trying to cuddle him but he wasn’t even holding me too so after that day he stopped texting me, and I thought that sex sucked but now I am really having fun sex with another man. I lost it to a boy who I thought was a man.

  • Gender: Female
  • Age of Virginity Loss: 16
  • Current Age: 17
  • How would you categorize your story?: Regret
  • Country: USA
Sep 202014
 

So it happened about mid August of 2014, this girl whom I have known for a while told me she thought I was attractive. We went on a field trip on which she kissed me the next day she came over to my house while my father was away.

We made out for a while, then she showed me her boobs. We made out more, I took off my pants, she gave me a blowjob. She didn’t get to finish the blowjob because her mother called and asked when she would be home and she didn’t want to leave me with “blue balls”. So we ended up having unprotected sex in the doggy style position.

I’m not going to lie, I enjoyed it, but afterward there was an overwhelming feeling of regret and now I really wish I could have taken it all back.

  • Gender: Male
  • Age of Virginity Loss: 16
  • Current Age: 16
  • How would you categorize your story?: Regret