Jan 032016
 

So my “best friend” was telling my boyfriend a bunch of lies about me, he broke up with me but didn’t really give me a reason, later I found out what happened. I was so mad but I pretended I didn’t know since my best friend (I’ll call her Sarah) was throwing a party the weekend coming up. I thought it was the perfect time for revenge. The night of the party I was hanging out with Sarah, her boyfriend (I’ll call him Josh) and a couple other people. I pulled Josh away and I kept handing him drinks so he would get drunk enough so I could make my move. Then I took him up into Sarah’s room and I started undressing him. He said “what are you doing” I said don’t worry about it. He undressed me and put on a condom and well you know what happened from there. After about 15 minutes Sarah walked in! Her reaction was hilarious. She started yelling at us, I got dressed and while leaving her room I whispered in her ear “Karma’s a bitch” and left the party. I haven’t talked to either one of them since then

  • Gender: Female
  • Age of Virginity Loss: 16
  • Current Age: 16
  • How would you categorize your story?: Funny
  • Country: Canada
Nov 292015
 

So my bf is 23 and he’s had sex before but never with a girlfriend. Once with some girl he met on holiday and another time with a classmate. You’d think he’s a player but he’s actually such a mummy’s boy it sometimes scares me. Anyway, we have been dating for a month and he thinks I loss my virginity to my ex (who I’ve only gone down on). We get a room in a sleazy hotel and TRY to have sex. And honestly, by try, I mean we spent the entire day trying to get his dick in me. He wasn’t small or anything, I was just really tight I guess. After 12 hours of foreplay, a lot of fingering, blowjobs and 6 condoms, we give up and check out. Fast forward a couple of months, he comes over to my place in the summer when my sister and parents are at school/work. We got so heated up and had a very pleasant fuck. HAHA mind my language, but it was amazing. I rode him twice and we missionary once. I think he came 4 times. Still remembered him saying “Babe I think I’ve ran out of cum” which just made me burst out in tears. I cried a little after because I’ve been waiting for it for so long. We were so into it and loved how we felt that day that we “made love” every week after that day. Had a lot of pregnancy scares because sometimes he would pull out and my period is really irregular but I never felt awkward or dirty or it being sexual. It just felt right. We are still together almost a year on and I’m glad it was with him.

  • Gender: Female
  • Age of Virginity Loss: 18
  • Current Age: 19
  • How would you categorize your story?: Funny
  • Country: Singapore
Nov 012015
 

So this summer my cousin and i were snap-chatting this guy named zach and well zach tries getting with anyone he can. so he asked my cousin and i for a threesome. so we took this as a chance to play a joke which we tend to do a lot. so we told him yes but we were going to tell him we were trans right before we did it. So we got all dolled up and met him at the golf course parking lot a half mile away from my cousins house. he met us there and we were talking outside his truck for like two minutes and we couldn’t tell him we were trans so my cousin pretended to be drunk but I’m a terrible liar so i couldn’t.

so we got in his truck and were driving around for a good twenty minutes so we decided to go down this dirt road and he stopped his truck and told my cousin to get out of the truck so she did and he climbed in the back seat and told me to so i asked why and he said so we could talk well i got in the back and he grabbed me and tarted kissing me and then grabbing my boobs and pussy he then took off my shirt and bikini top then my shorts and swimsuit bottoms i then took off his clothes his dick was huge i then started sucking it and then he layed me down on the seat and spread my legs they went really far because I’m a cheerleader and extremely flexible so he found the hole but it took him a long time but he finally found it it was really hard to fuck because it was really small but he finally came.

then i got dressed and he opened the door to tell my cousin to come back she got back in the truck and he was driving us home and he decide to call his best friend the guy i had a thing with and tell him so that didn’t end well but we still fuck almost everyday after cheer and football practice. 

  • Name: madison
  • Gender: Female
  • Age of Virginity Loss: 15
  • Current Age: 15
  • How would you categorize your story?: Funny
  • Country: USA
Oct 122015
 

Period. Shower. Sex. It was with my best friend and it had to be that day because I was leaving for college and we wanted to do it before I left. I was stressed with so much going on so my period came early. We decided to do it anyway. It was the most awkward experience of my life because we wanted it to be with each other even though we aren’t a thing. We figured the best place to do it was in the shower to not destroy my sheets with blood. Well we both ended up slipping and then sat there laughing in the tub. I somehow don’t regret a thing.

  • Gender: Female
  • Age of Virginity Loss: 17
  • Current Age: 17
  • How would you categorize your story?: Funny
  • Country: USA
Aug 092015
 

I met this guy two years ago and we both were virgins. we tried having sex but he got too nervous so it never worked out. we ended up becoming best friends and then two years later i lost it to his roommate/best friend in his bed while he wasn’t home. it was the same bed me and him originally tried to lose it in too.

  • Age of Virginity Loss: 17
  • Current Age: 17
  • How would you categorize your story?: Funny
  • Country: USA
Aug 032015
 

My boyfriend and I had been dating for about six or seven months, and I knew that I was ready for sex. I wasn’t necessarily sure I was in love with him at the time (looking back, I definitely was), but I just knew that I was physically and emotionally ready to lose my virginity at that point. My best friend’s parents were out of town one weekend, and she had a party. My boyfriend and I both went, and I got slightly tipsy while he got pretty drunk. He handles his alcohol really well, however, so I couldn’t even tell he was drunk until he told me. Anyway, I was pretty frustrated because we had been trying to have sex for about a month, but when you’re 16 it’s pretty tough to find the right time (ie: a time when your parents are out of the house and not watching you like hawks). So even though the two of us being tipsy didn’t fit with the ideal, romantic notions most teen girls have about losing their virginity, I was just like ‘fuck it, I am so ready to have sex and I don’t even care if I’ve had a couple beers’.

Anyway, so as the party was starting to wind down and people were starting to either crash or head home, we claimed the guest bedroom. Just to be clear, the girl who was throwing the party has been my best friend for 15 years now, and I practically grew up in her house. We would always sleep in her guest bedroom when we had sleepovers, and I have so many memories of lying in the bed in there talking about boys and playing truth or dare and marry/kiss/kill. So many fond childhood memories…and I will never look at that room the same way. Anyway, it didn’t hurt very much at all, which surprised me since everyone always talks about how painful sex is the first time. He promised to be gentle, and he really was. He was a lot more experienced than me, and did most of the work; I actually ended up coming 3 times! There was a lot of laughing and cuddling and it was definitely a pretty great night.

I’ve always been super loud, and the next morning my friend was just like ‘I can’t believe you lost your virginity in my guest bedroom’. And I was like lol sorrynotsorry. People always have this idealized image of what losing your virginity is supposed to be like; it’s supposed to be incredibly special and life-altering, and of course it’s going to hurt like hell, but you’re going to come out of it totally in love with the guy. It’s not always like that. It wasn’t like that for me, and I’m happy about that. Even though I did end up totally falling for my boyfriend, it didn’t have much to do with whether we had sex or not. And even though I lost my virginity in my friend’s guest bedroom, and it wasn’t with someone I was madly in love with at the time, and it wasn’t his first time (not by a long shot), I’m so happy it wasn’t that perfect, idealized virginity loss. It wasn’t awkward, and it didn’t hurt, and that’s good enough for me! So yeah. That’s how I lost my virginity.

  • Name: Cassie
  • Gender: Female
  • Age of Virginity Loss: 15
  • Current Age: 19
  • How would you categorize your story?: Funny
  • Country: Canada
Aug 032015
 

I’m 16 years old. I have been babysitting for a couple since i was 12 and for the last couple of years I have had a silly crush on the husband. A couple of weeks ago I sat for them then he drove me home. On the way he made a comment on how I had grown up to be a beautiful lady. I thanked him then to my surprise he put his hand on my leg. I didn’t say anything but looked at him and he smiled. I melted !!! He pulled into a vacant parking lot pulled me over and kissed me. I so flattered that we started kissing. At first it was very simple but before long it got really passionate. That was as far as I had gone with guys I have dated.

As we were in the middle of one of the kisses he started to ease me down in the seat and I just said “Ohh Mr. A___ !!!” He was between my legs then he ran his hand in my panties. With that I told he I had never done anything. When he ask if he could be my firat then only thing I said was “Oh my God !!” I guess he took that for a yes and he started getting himself out. I was so excited that I broke out in a sweat and could hardly get my breath. Then he started in me. I let out a sigh and he ask if I was ok to which I said yes. It was awesome. When I ask if he wasn’t afraid he might get pregnant he said he wouldn’t mind if I did.

When he finally came in me my whole body shook. Once we were finished he drove me home and he kissed me goodnight. A few days later I got my period and I was actually a little disappointed but also knew it was best.

  • Name: Renee
  • Gender: Female
  • Age of Virginity Loss: 16
  • Current Age: 16
  • How would you categorize your story?: Friend
  • Country: United States
Jun 142015
 

So I’m watching Supernatural with my boyfriend and I just start kissing him on his neck and I work my way down to his chest. after awhile of me just kissing him, he rolls over on top of me (we’re both shirtless at this point) and asks me if I want to have sex. I told him that I didn’t know if I really wanted to (the only reason I said that though is because he is from a christian family and was taught that sex before marriage was bad). I told him that I didn’t want to pressure him into anything and that I wasn’t the one with the moral issue. I left the decision up to him and he decided that he wanted to do it, so then I asked if he wanted to be on top or me. We decided to try him topping, but when he got it in, I stopped him because he was literally in as far as he could go and he wasn’t even fully inside (I guess that I wasn’t as turned on as I thought I was). Anyway, I decided that I should go on top so that I could get adjusted at my own speed (let me tell you, it felt a lot better when I was in control).

Since he has a bunk bed, when I first got on top I hit my head, but then I found out that I could use the bars underneath the top bed as handles so that I didn’t have to hunch over to put my hands down. I finally got to the point that it didn’t hurt anymore after only a minute or so, so I started speeding up and my boyfriend started using his fingers. I stopped him when I was about to come, because I wouldn’t have been able to keep going if I had, and I wanted to try and get him off. After awhile my legs were getting tired so we went back to him being on the top. This lasted for awhile and it felt a lot better than when I was doing all of the work, but after awhile we finally got to tired to continue (we had spent the entire day at the lake doing stuff like water skiing and tubing, so we were already tired to start with). We decided to stop and take a break. We watched a few more episodes of Supernatural while talking about how much respect we had for pornstars, because holy shit that’s a lot of work. He ended up getting me off with his fingers, and his parents came home right as I was going down on him, so he was stuck with blue balls for the rest of the night.

It was both of our first times and I wouldn’t have done it any differently (except maybe turn the tv off while we were doing it, because we both took turns watching it when we were on bottom).

  • Name: sam
  • Gender: Female
  • Age of Virginity Loss: 17
  • Current Age: 17
  • How would you categorize your story?: Funny
  • Country: USA
May 252015
 

I just turned 17 when I lost my virginity, I lost it to my ex boyfriend who was 16. (We weren’t together when I lost it to him, but we were still really good friends and we’ve talked about me giving him my virginity, even though he wasn’t one himself.) anyways, it took place at a Pow-wow, in a tent. (A pow-wow is a First Nations event that usually takes place for three days.) Me, him and his cousin were all hanging out in his cousins tent, drinking a little bit of alcohol. We got a good buzz before it happend. I took off to go use the bathroom, and when I got back he was already asking me to get in the tent with him. So I did, since I planned it. We only had our bottoms off. Also I was completely off my period, so that was kinda embarrassing. We didn’t really do much but just the usual missionary position. It wasn’t great in my opinion. The tent was a small two person tent. (His air mattress took most of the room.)

I felt so claustrophobic. I gave him oral and that also wasn’t great.. After 2-5 minutes of “sex” I had to go because my friend found me, and bugging me to come out and help her with something. After we got our bottoms on I said “I have to go, Gotham City needs me.” Then I left. We also did it again the next night which was also pretty lame. I’ve had two other sexual partners after him and I say they were much better. #noragrets

  • Name: Danneh
  • Gender: Female
  • Age of Virginity Loss: 17
  • Current Age: 18
  • How would you categorize your story?: Funny
  • Country: Canada
May 102015
 

So i have been dating my current boyfriend for about 10 months now. he’s one of my best friends and i trust him with my life. we had come very close to going all the way multiple times, but every time there was something stopping us (ie, parents coming home, on my period, ect). so one day we were at his best friend luke’s house for a party. there wasn’t a lot of people there (only like 10) so us being missing from the scene would have been noticed. we had both been drinking when we snuck out of the room. we went into luke’s bedroom and started hooking up. soon things got really heated and we went all the way. in the middle of *ahem* you know, luke thought it would be funny (being quite wasted himself) to pound on the door saying we needed to get out because his parents were home. we panicked and snuck out of his window, breaking the screen, to sneak back into the basement so lukes parents wouldn’t know we were in there. when we managed to get back into the house, luke was laughing his ass off saying they weren’t actually home and he was just messing with us. i love my boyfriend, i only wish i had been sober for it. i don’t regret it, it definitely was not how i expected it to go, but it was memorable.

  • Name: sarah
  • Gender: Female
  • Age of Virginity Loss: 15
  • Current Age: 15
  • How would you categorize your story?: Funny
  • Country: USA