How I lost my virginity. [F,M] | 2016

This story takes place a few years ago, the month after my 18th birthday.

I had known Dylan since we were both in Pre-K. He was always one of those bully types toward girls that he liked. I was always one of the girls he enjoyed picking on. This eventually turned into us being best friends throughout middle and high school. I was always one of the guys around his group of friends, but when we were alone, things seemed sexually tense between the two of us. Regardless, Dylan and I remained friends until after graduation when I moved to college.

A little after my 18th birthday, I got a Facebook message from Dylan, telling me he had heard I moved and that we apparently lived not too far from each other's respective colleges. To shorten a long story- Dylan and I talked on Facebook for around a week, flirting heavily, until one day he invited me to meet him. He gave me directions to his place, and I showed up around 7 pm.

Seeing Dylan that night was like meeting him for the first time. I was shocked when he opened the door, to see his normally unruly mop of brunette hair now trimmed neatly, his usual pudgy midsection now toned, and his thick frames seemed to be nowhere in sight. I stood back, a little shocked, to take in the sight of him. We joked about how "hot" I now thought he was as he showed me to the couch.

I couldn't help but stare as Dylan plopped down on the couch next to me, remote in hand, staring intently at the channel guide. Unexpectantly, Dylan turned, smiling at me, his one dimple shadowing in the dim light of the tv. I giggled a little as he took my hand in his and told me how cute I was. Before I could grasp the situation, Dylan was leading me by the hand toward his bedroom.

I shut the door behind myself and wrapped my arms around Dylan's shoulders, pulling him roughly in to a kiss. I felt a familiar heat rush in between my legs as our tongues twisted together sloppily and quickly. I threw my shirt off and ran my hand down Dylan's body to hook my fingers under the edge of his to pull it off as well. He backed us over to the bed, pulling our pants and underwear off as we went, never breaking the kiss. I felt the backs of my knees hit the bed and let myself fall back onto it, pulling Dylan on top of me.

I could feel his hard cock rubbing against my already swollen clit as he scooted his way up on me a little more before backing away completely. Dylan took each of my legs in his hands and pulled them apart, wrapping them around his shoulders. I knew I was soaking wet as he ran his tongue up my thigh and traced it around the edge of my pussy before he stuck two fingers into me. Up until that point in my life, I'd never done more than kiss a boy, so his fingers made me gasp in pain and pleasure. He kept working his tongue on my clit as he pumped his fingers in and out of my sopping wet pussy. I could feel my juices leaking onto the bed and I knew he could too, because just as I was about to cum hard, Dylan pulled his fingers out of me quickly.

I pulled him up further into the bed and pushed him gently onto his back. Then I made my way down his body to his cock. I thought it was really strange seeing one in person for the first time, it was obviously throbbing at about 6 inches long and decently thick. I felt like I was going to cum just seeing how hard I had made my old friend.

I licked all the way from the base of his cock to the head and swirled my tongue around it a couple times, licking the pre cum off as I went. Then I took the whole head of his cock into my mouth and sucked hard, trying to fit more of it in as I went. Being my first blow job, it wasn't very sexy, and it was extremely sloppy, but Dylan had his fingers twisted in my hair in a matter of minutes, grunting and thrusting into my mouth.

Seeing that he was close, I quickly pulled my mouth off his cock and climbed up next to him in bed. I spread my legs as he positioned himself on his knees inbetween them. He took his cock in his hand and ran it up and down my slit, pressing hard over my clit as he went a few times before he started to slowly slip it into my pussy. It hurt as I felt the head push in, but I was extremely wet; I wrapped my legs around his ass and pulled him into me all the way. I could feel my pussy stretching tightly around his big cock. I moaned again at the mix of pain and ecstasy I was in. As he pumped in and out of me, my pussy stopped hurting as much and I was really able to get into it. I reached down to rub my clit quickly and soon felt myself about to cum.

As my pussy tightened and spasmed around his cock, Dylan began to breathe heavily and pump even faster into me. This sent me over the edge again and I came moaning his name. I felt his dick twitching inside of me just before he shot his hot load all in my pussy.

Thanks for reading!