Reader Hookup Confession: I Lost My Virginity To My Best Friend’s Boyfriend!

If there’s one thing girls can always bond about, it’s an embarrassing hookup story. Trust us: we all have them. So don’t be shy! Read this OMG reader hook-up confession, and then send your own to

I had never had a boyfriend before, but my best friend had had quite a few. One day, I was with her at her boyfriend’s house, and she had to go home to do some homework. I was going to go home too, but her BF, let’s call him Dan, said I should stay for a bit… after all we’d be hanging out quite a bit now that he was going out with my best friend!

So, after my bezzie had left, Dan and I started jumping on the bed. Eventually, I fell over; tripping him up, and he fell on top of me. We hugged and laughed and then he brushed some hair out of my face. He told me I looked beautiful and kissed my forehead. And then, somehow, we were making out!

I kept pushing him away, but he just said, “Shhh, it’s okay, she won’t find out,” and eventually I gave in. It went way too far and he ended up giving me oral sex. His mom walked in in the middle of my orgasm! She thought I was Dan’s girlfriend, excused herself and left. The next time my BFF and I were over there, his mom kept dropping hints. It was awful.

I feel like such a bitch. I lost my virginity to my best friend’s boyfriend!

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Guess who farted while these two were hooking up?

Posted in: Hookup Confessions
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  • kkzzz

    mate if you have sex with your best friends boyfriend / girlfriend , your a disgusting. its horrible imagine it happening to you, you would be devastated. your obviously not a good friend, and are extremely fake to do that.

  • marrissa

    Im 14 and my cousin is 20 she has a boyfriend and one night we were all hanging out and my cousin fell asleep on the couch and me and her noyfriend statrted talking with her boyfriend is not even near 20 he is my exact same age and so we were laughing about silly stories when he got closer and closer to me I was freakin out because I never got kissed before and so it got so hot and heavy I fell asleep so he carried me into his bedroom through me down on the bed and I was still asleep and so he started humping me which turned out to be very sexy and so he woke me up he said for me to sit on the bed so I did and he went on the floor and started sucking me and he grabbed my boobs and started sucking them 1 at a time andnthen my cousin walked in to go tocthe bathrom and so I hid under the covers so luckily she was really drunk from drinking so she didnt notoce me so he and I hooked up and now were dating and like every 2 minutes we have sex because u know so my cousin hates me so even though weve only knew each other for like 2 days bit weve hook ed up loke 20 times already

  • Jane

    I slept with my friends bf on 3/8/14 which is obviously not that long ago. I met him before I met her, everyone at my school knows I have the biggest crush on my best friend. So I had him over and usually we just nerd out and talk about video games and comics. Well my mum said it was fine for him to stay the night because I was going to be home alone. She sees him as her son so I’m guessing that’s why she did so. ANYWAYS, we started wrestling and I pinned him down and he rolled over and had me pinned. He leaned in closer and we made out for what seemed like hours. Once we were all hot and bothered he lifted my skirt and pulled his penis out and just went it. It was the best experience i had ever gone through. I don’t feel bad about what I did, if anything I might ring him up and go again.

  • heather

    I am 14 but my step sister is 17. She is always telling me off and saying how preppy I am and really sayd stupid things abt me when her bf is around. She likes to do that becoz he is 23 and she things it makes her look cool by doin tht.
    Last weeked she got real drunk and fell asleep wile making out wit him. I was in my room and he came to my room and we started chattin. I let him get close and he started kissin an cuddlin me. I had just my long TShirt n undies on and he made me take my undies off nd started kissin me between my legs. I had never been wit a guy before but it felt gud. He wus relly really nice n kept tellin me how he liked me. Evrythn went so quick n one thing led to another and i ended up havin sex with him.
    I didnt mind losing my virginity. I thought it wus a nice way of gettin back at my step sis.

    • Maci

      Umm… Sorry to inform you of this. .. But if he’s 23 and you’re only 14 then he’s a PEDOPHILE!! WHOMEVER RUNS THIS WEBSITE SHOULD BE IN TROUBLE FOR ALLOWING THE POSTING OF THE ABOVE STORY/REPLY !! DISGUSTING!! SHAME ON HIM!!!!!

    • Kaitlin

      Hey, Heather. I don’t want you to feel afraid or anything, and I know it’s been a while since you posted that comment, but if you ever need someone to talk to, or help with dealing with what you’ve been through, there are lots of support sites online. You are not alone, and what that man did to you was taking advantage and wrong. You are a strong woman, and you don’t need to explain away what happened in your mind. You are not alone.

  • Tracy

    I have a hookup confession!!! Me and my boyfriend were dating for 2 years and had considered going to a new level but never did. WE were getting really close and had wanted to have sex sooner or later. So one day, I was with my boyfriend, let’s just call him S, and we went back to his place after a party. I had never had sex before so I was kinda scared. Before I knew it, we were making out on his bed. Things got pretty heating and he was going fast. I groaned REALLY loud and eventually his bed’s legs broke. S got even faster and I was started to have an orgasm. THe bed was still rocking and we forgot to lock the dorr and his little sister who is 7 walked in and saw us… know what. We immediately got off of each other and stared at her. She asked what we were doing and we said we were wrestling and she bought it. My boyfriedn and i laughed about it but still it was the worst hookup ever

  • pinkCherry

    My best friend is away and I know her bf is on his own. I have always had a huge crush on him and I know he likes me too. He is away in Uni a lot and so I dont get to meet him a lot. I made bold to call him up and he invited me to go to his place. I am 14 and I have never had a bf. I have never done any thing with a guy before.
    I let him kiss me and things started happening. OMG he was so cool he didnt even mind me being 14. I felt guilty because he was my best friends bf but I liked him a lot too and wanted to feel that closeness with him. He fingered me and ate me out and I sucked him and stuff. Things happened so quick. I was very anxious but i really enjoyed all that was happening. It felt so good. 😛 😛 I had never felt such a strong orgasm before even when I masturbate. I let him take my virginity and we had sex a few times that day.
    I have promised him I will never mention this to anyone. Though I feel bad I dont regret what I did