Best Friend Takes My Virginity

From the very moment I laid eyes on her she became almost my sole fantasy when it came to sex. I met her through a friend during a night of clubbing and after some banter and a few drinks, we exchanged numbers but nothing really came of it as i was a social retard. Over the next couple years we would occasionally run into each other due to mutual friends and remained friendly.

One day by some insane coincidence or act of god, she got a job in the same department as me, having no idea that i also worked there. We began to become a lot closer while working with each other and my attraction to her continued to grow, we even flirted with each other quite frequently. As time went on, she appeared to lead me on and this was when my infatuation with her started to skyrocket, however, after several outings outside of work and intimate encounters, my dream of pounding her senseless seemed like it would remain just a dream more and more, she had a good looking, wealthy, and successful boyfriend.

I spent so much of my time daydreaming about the idea of finally sliding my rock hard cock deep into her tight little pussy. I used to imagine what would it would feel like to pull up that tight work skirt or slide off those skimpy little shorts and grab that perfectly tight round ass which I could only ever catch glimpses of when it was covered by the bare minimum length shorts that she seemed to love wearing to tease guys like me with, along with the rest of her flawless body.

As we got closer and closer, she began to ask me more and more intimate questions, one night she asked me how long it had been since i last had sex. Being 20 years old and extremely anxious about the fact that i had never even seen a girl naked in real life, let alone fucked one, I hesitated before i decided to lie and say "it's been a while". Apparently she saw right through my bullshit and kept pressing me for more information, eventually proclaiming in a slightly mocking tone "aww.. sweetie you're still a virgin aren't you? My poor sweeties never gotten any".

We had hung out in my room together half a dozen times watching movies together and i never made a move due to the fact that i was terrified, and because she also had a boyfriend. One night she came over crying because of a conflict she had with one of her family members. I wasn't sure how to console her so i did what i usually did and suggested we watch a movie to get her mind off things. Although we had lay in bed together before, I never really attempted to touch her and always kept myself slightly separated from her. This night however she pulled my arm around her and we began cuddling for the first time.

It sounds sad in hindsight but this was one of the most blissful experiences of my life as I had never been this physically intimate with a girl before, and this was the girl of my dreams. Eventually as the night went on we would low-key brush parts of our body against each other and it was making me really hard. Out of nowhere she asked me "Do you ever think about doing me?" I said yes, and kind of confessed my feelings for her, "would you wanna do me right now?" was the next question.

I was so nervous and scared and excited and terrified at the same time that I don't even remember exactly what i said, but it must've been something along the lines of "god yes I wanna do you so fucking bad right now". Ignoring the fact that she had a boyfriend, which i wasn't about to bring up, we started to touch each others bodies and feel each other in places i had only dreamed i would ever be able to feel. Eventually this led to us kissing (very badly and awkwardly on my part) and finally after about an hour of enjoying every part of each other besides what was still covered by her skimpy shorts and tight black underwear, she told me she wanted to feel my dick inside her, sliding off her pants and opening her legs for me, spreading them apart.

Even as i lowered myself in between her legs i was freaking out, filled to the brim with anticipation of what i was about to do, with her help i managed to find the opening of her pussy, pushing against it and feeling it slowly slide into her warm tight hole (She didn't make me use a condom because she was on birth control for her bf). I couldn't believe how good it was, how tight, wet, and warm it felt as i tried my best to keep a steady rhythm while sliding in and out of her. I admittedly didn't last very long but it didn't really matter because this was just the first of a long period of several months where she let me shove dick into her almost daily. She even started letting me record us :)