Lost my virginity to my best friend (mf) (Cheating)

So to start this off, I'm here to turn people on, not start a moral debate, if you don't like what I've done, don't read it.

In my last year in high school I was a bit of a late bloomer. I had a handful of girlfriends but nothing past second base. I started getting close to Erika and Anna both at the end of the year. Anna was in a long term relationship, but we had grown extremely close to the point that I considered her my closest friend. Anna was about 5'2'', blonde, blue eyes, with curvy hips and D cups. Erika, while on the less attractive end of the scale, had a great personality, with red hair and freckles. She never wore makeup and was a tom-boy.

Erika and I entered a highschool type, hands holding, light peck kisses only type of relationship a couple months before prom. We never had sex, she'd barely touch me for the most part. We had next to zero chemistry, but I wanted to give it a go anyways, since I had gotten desperate. As the partying picked up, Anna and I would flirt more and more. Grinding, arm on the leg when laughing ect. The sexual tension between us became palpable when we were alone.

One night, after a usual night of Erika staying sober, driving her friends home early and ditching me at the bar. Anna and I were dancing our asses off together, having a blast. Our group of friends began to make arrangements for getting home. Anna had no ride, so I suggested (genuinely innocently) that she could just sleep in my bed and I'd take the couch. I got a couple of strange looks from some of my friends, but I thought nothing of it since my friend was in a relationship and clearly not interested in me.

We got home, and I got some blankets for the couch and plopped down. Anna sat down next to me, practically on my lap. We started talking about random stuff like we always do. She yawned and said she was going to bed, then said it was nonsense for me to sleep on the terrible couch and invited me to her bed. Again, completely innocently I stripped down to my boxers and jumped in next to her. For another hour or two we just chatted about our relationships, our plans, ect. As we laid there her hand slowly started moving closer and closer to me. Eventually she rolled on top of me and just sat there, and we kept talking. At this point I realized that something was up, (Yes i know I'm a genius), her lips were half an inch from mine, I could feel the heat off of them as we talked. Clearly things were getting heated and my cock started to stiffen beneath her, which she clearly noticed, as her hips very slowly started grinding on me. Eventually, all the blood left my brain, and I pushed my lips the final gap and I had one of the most deep, electrifying, explosive kiss of my life. Months of sexual tension finally released, our hands ran up and down one another.

After a few minutes of us making out, I finally snapped to it and realized what was going on. I rolled her off me and told her we couldn't go back if we went any further. Her hand moved down to my cock and started stroking me through my boxers. I let out a soft moan and she asked me if it felt wrong. I'll admit, it didn't, at all. I slid my hand under panties and felt the warmth radiating off of her pussy. My finger spread her lips and she moaned and her legs squeezed around my hand, losing her concentration on stroking me. I started sliding my finger in and out of her. She moaned and wiggled and gripped the sheets roughly.

The anticipation was making my heart pound. Then a silence fell over the room, we hadn't said a word in ten minutes. Then I heard those words I'll never forget; "Are you going to tease me all night, or are you going to get over here and fuck me". At that point, all bets were off, I didn't care about any consequences. I ripped her panties off and rolled on top of her, pushing her knees to her chest. Pressing my cock against her wet slit. I let out a moan as i pressed forward. It was an unforgettable wave of ecstacy that completely took me. In that moment I was in another place, another world. I started thrusting into her, trying not to cum instantly. The feeling was overwhelming. I plunged into her then stopped there, we kissed deeply and her nails scratched across my back, leaving deep red marks across my backs. As I became more and more used to it, I started thrusting all the way out, and slamming back in as hard as I can. She let out a yelp every time I slammed into her. Her eyes closed and she started screaming; fuck, fuck fuck fuck, fuck yes! I slid out of her, grabbed her hips and pulled her to the edge of my bed. Her legs were too short to even touch the ground, she dangled there as I plunged into her again, spreading her cheeks. I grabbed both of her wrists and pulled them behind her and started ramming her as quick as I could. I could feel the orgasm building up inside me and I told Anna I was close. She started to moan herself, I could feel her pussy tensing up on me, my eyes rolled back and we were both moaning loudly. I told her I was cumming and she told me to pull out. I let go of her arms and she immediately rolled over and opened her mouth. I moaned out; "OH FUCK ANNA" and rope after rope of cum shot all over her chest and chin. We both laughed and I kissed her deeply. We cleaned up and cuddled and kept cuddling. We woke up in the morning and went for breakfast, from that point on, our friendship would never be the same. I couldnt believe that I had finally lost my virginity, and to my best friend, and that it had been fucking unreal. Then I also thought about Erika, and realized that asking her out had been a terrible mistake, and that I had to end it with her immediately. Unfortunately…The affair lasted much longer than I anticipated…but that's another story.

Extra Part: My mom had been working night shifts, so I thought we had been home alone, after we had fucked for half an hour, extremely loudly, we heard a cough and then someone leaving the house. Apparently my moms boyfriend had been sleeping in the other bedroom the entire time. He never once questioned me about it. Total Bro.

Source: reddit.com/r/gonewildstories/comments/3zdb6n/lost_my_virginity_to_my_best_friend_mf_cheating

15 comments

  1. I have a really good girl friend that got cheated on, damn, me & some friends got so mad – the fucker was in a hospital for about a month and a half and we never saw him again, thats not even all that cheaters deserve

  2. believe me if you want, huh, like i care… but make sure you satisfy yourself with some cheating stories, scum…

  3. Dude, he literally named them Erika and Anna… as in Elsa and Anna from Frozen. And all he did was switch the defining features. Cool your jets, it was fake.

  4. I actually didn’t make that comparison, but that’s really funny! Although they’re not quite the same, Anna was short and a little curvy, and Erika was not that good looking, unlike both characters you referenced. These aren’t their real names for obvious reasons, but it is a true story.

  5. I despise cheating too but that’s a bit much putting someone in the hospital for it.

  6. there is way, way worse stuff on Reddit that you could be going after than cheating, chief

  7. Don’t feel bad, I was in the same situation you were. Dating a girl just to date her, while being incredibly attracted to another girl.

  8. I do feel bad. It was a shitty thing to do and I could have handled it all much better than I did. I love definitely learner from it though

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