Jan 042016
 

I first met Gabby when I finished college and moved back home. I didn’t have a job yet so I moved back home with my folks. I was spending time with friends when I met her and we began hanging out alot. One night when my parents were away on vacation Gabby decided to spend the night night with me and I knew it would happen. We made out on the couch and she said she wanted to have sex. I told her that I didn’t have a condom and she just replied “do you have at least have a bed?” I said “of course” and we went into my room. We kissed more and took each others clothes off. I started fingering her and she loved it. The she layed down and I started fucking her. She made me pull out and I came on the sheets. We had sex a few times in the next few weeks. A few weeks went by and then I found out she was pregnant. Even worse she said I probably wasn’t the father. She had sex with her ex shortly before me and he came inside her. She moved in with him and was crushed.

  • Name: Ben
  • Gender: Male
  • Age of Virginity Loss: 22
  • Current Age: 24
  • How would you categorize your story?: Regret
  • Country: USA
Dec 132015
 

My boyfriend of about 5 months came over the weekend after Halloween and we were in my bed watching movies and such. Things began to get heated and he started fingering me. He transitioned from being next to me, to on top. He then quickly took off my shorts and my underwear and continued. Then he started pulling down his shorts. At this point I just thought he’d stroke down there since he’d done it before. But he placed it like he was gonna enter me and asked me if it was too far. I said yes, so he pulled up his shorts and went back to fingering me. Something happened (I don’t remember) that he wanted a “prize” for. He lowered his shorts again and put it at the lower “hole” asking for anal. I told him that it wasn’t an entrance so he put it back on my vagina and lightly pushed.

He starting saying “just say no” but for some reason I would, I did keep scooting away every time he pushed a little. Then he said just once in and once out, once again I didn’t say anything. With that he pushed inside me and I felt a little pain. This went on for like five minutes until the realization hit me. I wasn’t a virgin. I was fifteen. I felt so ashamed. I stopped and curled into a ball, hiding my face and quietly crying. He cuddled me and asked what was wrong I just said nothing and refused to admit I was crying (though I obviously was). In a way it was against my will, but I didn’t say no so I can’t really claim that I guess.

We’re still dating but I’ve only told two people: my ex boyfriend over text when I was freaking out later that night (he’s practically my best friend) and the school psychologist (that’s a really long story). We’ve had sex two other times which were practically just as brief but at some points I’m still in denial about what I’ve done. As for a little advice, don’t be afraid to say no it’s better than regretting it in the long run.

  • Gender: Female
  • Age of Virginity Loss: 15
  • Current Age: 15
  • How would you categorize your story?: Regret
  • Country: Germany (US Territory)
Nov 232015
 

So i was 18 and she was 15, we did it in a public park the morning after I went to the club haha OMG. we both did regret it i used protection but she was crazy and kept calling me telling me she was pregnant, turns out she is super crazy and lied about it. REGRET IT SO MUCH

  • Gender: Male
  • Age of Virginity Loss: 18
  • Current Age: 18
  • How would you categorize your story?: Regret
  • Country: Australia
Nov 232015
 

I was a lost teen or whatever. I’ve heard those stories, I just never thought of it or about it lol. So there’s this boy I would text and later on he would tell me that he’s ganna loose my virginity and I would think he was joking. He came over one day and it was just me and him in my room and he was basically begging so in my mind I just thought whatever just get it over with no big deal. It happened and it hurt.. We just did it for like 2 minutes but he didn’t cum. He then left and then came back like 2 hours later and we did it again for 5 min and this time he did cum. Then he left and I hardly heard from him again. I swear I was so lost. I didn’t even know what I just did and that’s how you know I had no one that was ever there for me lol. I just didn’t know. I didn’t think it was a big deal and I never watched out for fuckboys, I didn’t even know what it was or what they want. It took me 3 years to finally realize what I actually did and why I did it. This is suppose to be a sexy story but there is a lesson learned about this. Everything does happen for a reason.

  • Gender: Female
  • Age of Virginity Loss: 13
  • Current Age: 17
  • How would you categorize your story?: Regret
  • Country: USA
Nov 152015
 

It happened my freshmen year of highschool. I will admit I was a pretty distraught teenager. There was this cute boy named Ben who had this daring rebellious thing about him that none of the other boys in my class had. We talked alot like all the time. It was an outsider thing I guess. His longer black hair and this black hoodie he used to wear constantly was so hot! Plus he played the guitar which OMG! Anyways one day after school Ben and I snuck to the downstairs bathroom and started making out. He didn’t really seem to know what he was doing but neither did I so I decided to push it even further.

I climbed down from the sink and undid his pants. His dick was bigger than I expected but I managed to get as much as I could in my mouth. He must’ve precummed because it all of a sudden tasted awful! But he lifted me up, took of my pants and ate my pussy which I’ll admit was awkward and I hadn’t shaved in a few days. When he stood up he started to pull his pants up and said we should go but I said we could have sex if he wanted. He had gone kinda soft but I grabbed it and guided it between my legs and told him all he had to do was push it inside me. He had gone from semi-hard to rock-hard in a second and he did.

He pushed his dick in as far as he could and i cried out letting him only pump a few times before pushing him out. He came after he was out and the cum was like running down his penis. There was only a little blood but I was embarrassed so I didn’t tell him. I just quickly pulled my pants up and I started crying. He said it was going to be okay and that we couldn’t tell anyone. I felt so guilty the next day I told a teacher. Ben and I both got in trouble but I told them all we did was oral even though him and I both know it was much more.

Maybe one day he’ll write a song about me on his guitar. I wish I could go back and save myself for someone else other than a horny teenage boy. It was a huge mistake and I’d recommend waiting. I feel gross just finishing this. But thats how I lost my virginity.

  • Name: Katy
  • Gender: Female
  • Age of Virginity Loss: 14
  • Current Age: 23
  • How would you categorize your story?: Regret
  • Country: Michigan, USA
Nov 152015
 

I was 14. It was the day before Thanksgiving of 2012. A Wednesday. My mother had gone to work and my brother was in Raleigh, NC with his girlfriend for a work convention. I had never done anything sexual other than a few kisses that involved tongue, but that’s it. D had texted me at like 7 o’clock in the morning asking if he could come over and I’m like.. “it’s 7am?? I’m not even up yet, plus, I have to wait until my mother leaves for work, which isn’t until 8am and I want to make sure she’s gone”. So, I told him to come over around 10:30am. He agreed. I immediately jumped up and ran to the bathroom to shower, SHAVE (the first time doing my cunt btw), and prepare for him because I wanted it to be perfect and didn’t want to have any setbacks. The whole while he’s texting me like “wyd?” and I’m like “..oh, you know, watching tv..lol” lying like a motherfucker.

Anyway, he ends up getting to my house early, around like 10am. Now, we hadn’t discussed doing any sexual activities. We were good friends and we had hung out alone before . Except, I was madly infatuated with this individual and he was mildly interested in me at most (at least that’s how I perceived it). We were watching tv sitting beside each other on the couch slightly cuddled up and.. the next thing I remember is leading him down the hallway to my bedroom. He asked me if I was ready and willing to have sex with him, and me feeling comfortable enough to say “No.”, I did. He said “Well, let me just take your clothes off.” I agreed. I was now naked. He was still clothed. He told me to reciprocate the same thing he did to me. His head got stuck in his shirt :/ it was awkward, as to be expected? I gave up and he said he’d just take the rest of his clothes off himself (which I suggested he do in the first place).

After he was down to his underwear he suggested he put on a condom. I hadn’t even thought of one! Thank God he brought one (although, in hindsight it should’ve been a sign that that’s really all he came over to do.. fuck me, which, I was surprisingly okay with). While he put on the condom, he said “Put on some Chief Keef.” REALLY??? You want to hear Chief Keef and you think I want that as background music when I’m about to lose my virginity? I didn’t argue with him any further and since he was still fumbling with that fucking condom I just laid across my bed diagonally with my legs spread wide. He finally turned around and I got to see my first cock. All veiny dark and thick, I couldn’t really be mad?? I’m still ambivalent around his dick. Anyway, he got on the bed, got in between my legs, and attempted to enter me… multiple times.

Okay, I’m skinny, I’m nervous, and I’m a virgin. It’s not really a good mix. Soon, he began to get frustrated and ultimately forced himself inside of me. I screamed out at the pain. All I felt was a sharp pain and tons of pressure. “What the fuck?” I said. “Sorry. Does it really hurt that bad?” he said. “Yes, just please go slow.” I said. After a few strokes, he decided to pick up speed. Somehow, he slid out too far and ended up shoving his entire penis into my ass.

WORST PHYSICAL FEELING I’VE EVER EXPERIENCED IN MY LIFE. FUUUUUUUUUCK. “STOP!” I screamed. “What? Does it really hurt that bad?” he asked. “I don’t know. Maybe we should find a ten foot pole, shove it up your ass, and then we can compare notes! Of course it fucking hurt!” I said, frustrated. He tried to cuddle with me after I obviously didn’t want to continue. He wasn’t large in length, but in width it felt like he could split me wide open. I kicked him out after that. We didn’t talk, text, or anything for a month. Maybe not until a couple of days before Christmas came around. We’re no longer good friends. That’s how I lost my virginity. It was shit, but what’re you going to do…

  • Name: Ambivalent
  • Gender: Female
  • Age of Virginity Loss: 14
  • Current Age: 17
  • How would you categorize your story?: Regret
  • Country: United States
Nov 012015
 

So last spring I was home from school and I was seeing this guy who I had met when I was home for the winter break. He was a little older than me and I knew the relationship wasn’t going anywhere, but for whatever reason I was still seeing him. We were on my making out on my parents couch. He reached up my skirt and took my underwear off, which I was ok with. In the middle of making out he blatantly entered me. I didn’t know what to say at first then I told him I wasn’t comfortable with this. I told him I didn’t really enjoy hanging out with him and that night I realized he didn’t respect me. I broke up with him and I left a few days later to go back to school. A few weeks passed by and I never got my period. I didn’t think I was pregnant because he wasn’t in me for long. I told my roommate and she said I should get tested. I did and I was shocked when I found out I was pregnant. I didn’t know what to do. I didn’t want to tell him either. I wound up having an abortion which sucked because I was always “the good girl” and careful about my sexulaity. I hope some girls out there will understand the importance of protection and waiting for the right person. Never put yourselves in a point like I did.

  • Name: Kayla
  • Gender: Female
  • Age of Virginity Loss: 19
  • Current Age: 20
  • How would you categorize your story?: Regret
  • Country: USA
Nov 012015
 

I never dated or held a job during high school; my teenage years kind of snuck up on me and before I knew it I had graduated and was working my first job at the local movie theater. This is also where I met my first girlfriend. I felt very inexperienced so I let her make all the first moves. We were making out on her couch at home and she moved my hand down from her shoulder to her tit, which surprised me enough I exclaimed “Oh my God!” She just giggled, and things rapidly snowballed from there; I lost my virginity within the first week of dating her. She was far more willing to let me take off her bottoms than her top, which annoyed me, but hey, first pussy! I wasn’t too upset given the circumstances. ;)

During those long, late night teenage phone conversations she had told me she preferred it when the man took charge, sexually. She wished I was more experienced than her, not less. However, I was a virgin and she was not, so I expected HER to take the lead and told her as much. So one night she and I were in her bedroom (with the door open to keep us from fooling around, for all the good that did!) and I was on top of her, kissing her. She reached under the pillow and produced a condom. We’d been talking about having sex so I wasn’t surprised. I rolled it onto my cock and got between her spread legs… and I couldn’t get it in!

The angle was just wrong and although I knew textbook female anatomy, the real world application was something else entirely. The reduced sensation from the condom probably didn’t help either. So after a few awkward attempts we gave up for the moment and went back to kissing and talking, albeit naked with the condom still on. About ten minutes later she said, “Ray?” “Yeah?” “Make love to me.” “Now?” “Now.” “Get on top of me.” And now that she finally took control, things went smoothly. She guided me into her pussy and slid down my cock, and I remember thinking at that moment, “Wow, I’m not a virgin anymore.”

The sensation was unusual, I’ve never experienced anything quite like it even afterwards; it was like all of the sensation was focused entirely on the ring of her vaginal entrance slowly sliding down my cock, almost like a cock ring. When she hit bottom she gave me a lustful look and asked if it felt anything like I expected. I breathlessly told her no, it wasn’t at all how I expected it to feel. We proceeded to make love, slowly and quietly so as to not get caught. Neither of us came, in fact neither of us came at all during that entire 6 month relationship! With 17 years of hindsight, I strongly suspect she didn’t really WANT to have sex so much as she did it because “that’s what boyfriends and girlfriends do.”

I know she felt a bit guilty for losing her virginity at 14, had yet to experience an orgasm, and probably had some issues with sex. I just wanted her to take the lead and teach me, she wanted the man to take charge so she could be swept up in it, and as a result we sort of fumbled around the whole relationship, sort of flying blind. If I had it to do over again I probably would have lost it to my second girlfriend, who was much more sexually assertive and would’ve ENJOYED “breaking me in.”

Ironically, it was after that that I gained enough confidence to take control in the bedroom, be rough if that’s what she wanted, and learn to FUCK instead of “making love.” So my takeaway is, don’t be in such a rush to lose your V-card that it prevents you from actually enjoying it. ;)

  • Name: Ray
  • Gender: Male
  • Age of Virginity Loss: 19
  • Current Age: 36
  • How would you categorize your story?: Regret
  • Country: USA
Nov 012015
 

So, I’m sure most of you know what it can be like being 17, ya know the whole “I hate my parents, I don’t want to live here” stuff. Ya, that was me alright to the point where I had been talking to a guy online who was 3 years older then me. We hit it off pretty easy, he seemed like a really nice guy. Finally it came to the point where a “friend of mine” and I decided we didn’t want to live with our parents anymore so we packed our bags and we ran away. We hitch hiked to the closest major city, which happened to be where the guy was from. Once we got there we headed for the mall and I texted him saying I was in town and asked if he wanted to meet finally. He replied saying ya, but he was bringing his room mate with him.

My friend and I waited in the mall and when he arrived he gave me this great big bear hug, which was amazing. After that, we all went to the theater and he paid for my ticket in which he stated ” If this movie sucks, you owe me a blowjob” Ya I had literally just met him and he was already talking like that. So ya, the movie sucked and we ended up back at his place where I did in fact give him a blowjob…. Which in turn led to my first time having anal, and his friend pretty much walking in on us..

I was pretty scared.. I ended up in the hospital the next day because he had been so rough during the anal that he bruised my ribs.. A few nights later he asked me out, I said yes of course because i thought he was a nice guy.. I was wrong. That first night of dating he took my virginity, which hurt alot.. Never having sex before that, I didnt really know what to expect and he also left a hickey on my throat that made it look like I had been attacked by a bear it was that big.., but every night after that we would have sex..

I wasnt even really ready to have sex at 17 but I did it so I could keep a roof over my head. Eventually I realized he wasnt a good guy.. It got worse everyday after I first lost my virginity, to the point where 5 months later he hit me with a door, and then when I tried to get out of the relationship I did end up in the hospital..

It was a mental rollercoaster,I mean I have a boyfriend now who treats me amazingly but memories like that never really go away. I worry that what my ex did to me will eventually screw over my current relationship due to all the issues I have now. But anyways thats how I lost my V….

  • Name: Dani
  • Gender: Female
  • Age of Virginity Loss: 17
  • Current Age: 22
  • How would you categorize your story?: Regret
  • Country: Canada
Nov 012015
 

I had just gotten out of school for the summer. There was this boy who went to high school hanging around the beach. I asked him his name and he said it was John. I was just starting to fill out a swim suit and noticing boys a lot more. Unfortunately my parents noticed and they put these restrictions on me. I couldn’t stay out late, I couldn’t go out on dates, and I had to wear this ugly 1 piece swim suit. I of course promptly got myself a bikini and was always at the beach, with friends, showing it off. Well this high school boy noticed me and I couldn’t believe it.

He asked me if we could go someplace and talk. I told my friends, who said I shouldn’t go but I ignored them thinking they were only jealous. We walked along until we came to this supply shed. He said he comes here when he wants to be alone and took me in. Pretty soon we were kissing pretty heavily and he was feeling up my breasts. (They were almost a B cup with padding) and I was in heaven. Here was a high school boy, practically a man, and he was making out with me, a 6th grader. I knew I should not be treated as a child. I was so wrapped up that I didn’t even notice my bikini bottoms sliding down. And soon I was on the floor of the shed and he had his trunks down and tossed away. I saw his penis but it was dark so I could only see it in the shadows and I started to get worried but then he said that I was the most beautiful girl he had ever seen and that he would love me if I let him. That sounded divine to a little 11 year old so I let him do as he wanted. He spread my legs and promptly started poking around down there looking for the opening.

It didn’t take him long to find it and soon his penis was pushing into me, past my hymen which hurt like hell. Then he started stroking it in and out. My bikini top joined my botoms and the padding I had put in there fell out of the cups but he didn’t seem to mind and whatever he was doing sure felt nice. Then he stiffened and I felt my inside filling with the sperm I had let him put in. He kissed me once and pulled out and threw me my bikini as he put his trunks back on. He said I was a great lay and left me there to dress.

It was horrible. he didn’t even wait for me and I couldn’t find him anywhere on the beach. The worst part is he got me pregnant. My parents nearly disowned me and I had to leave school. Pregnant 11 year olds are a bad influence on the other children. I had the baby, (cesarian I was way too small for the natural way) and although my parents didn’t kick me out , thay said I had to go to night school.

I hope anybody who reads this, especially those girls who think they are so grown up, will understand that just because your body is sexually mature doesn’t mean you are. and don’t do anything that might screw up your life as much as mine is.

  • Name: Lana
  • Gender: Female
  • Age of Virginity Loss: 11
  • Current Age: 13
  • How would you categorize your story?: Regret
  • Country: USA