I was a good girl all the way up through high school. Straight A’s, I never got into trouble, I always did as I was told, but, unknown to my parents, I’d gotten pretty heavily into watching porn. Watching the women sucking and fucking on the screen in my bedroom was the height of sexiness to me, and I, a virgin, knew beyond the shadow of a doubt that I 100% needed to get fucked.
Unfortunately, I hung out with a bunch of hopeless virgins like me, and I knew that the only way they managed to talk to me at all was to not view me as a sexual figure at all. Baggy clothes and no makeup only helped/hurt, I know, but I liked their company. Had I just whipped my tits out and announced my pussy open for business, I knew they would all run for the hills, so I did what I had to do to keep the friends I wanted. Graduation was only days away, though, and while I could have just walked into school with a tight top on and batted my eyes at some jock, I wanted something a little more personal.
So, I left home on a Wednesday night (with the full permission of my parents, getting fucked wasn’t worth getting grounded, as far as I was concerned), and walked over to my friend Joe’s house. Joe and I had been friends since elementary school, and he’d always been a great guy. I figured, if I was going to give my virginity to anyone, he would at least be appreciative. Plus I didn’t have my license yet, and he was the only friend I had within walking distance. Beggars can’t be choosers. I was wearing a baggy, zip up hoody over a low cut tanktop that framed my DDs very nicely, and some sweatpants that I knew would allow easy access. I knocked on his window like I’d done a thousand times before, and tried not to let him hear the tremble in my voice when I asked if he wanted to hang out somewhere. Less than a week before graduation, there was no homework to be done, so he was only too happy to have something to do for a couple hours before bed.
We walked to a park that was only about five minutes away. We hopped the chain to get into the softball field (the extent of our rebellious acts in our teens), and sat on the cool steel bleachers like we had a hundred times before. We talked about the usual things, everything and nothing, what video games he was playing, what movies we were excited about, and so on. I honestly couldn’t hear about half the conversation through the pounding in my ears. Finally, we touched on the topic of college. He was staying in-state to go to a technical college, while I was moving half way across the country to attend a fairly prestigious private college. I casually mentioned that I was looking forward to a fresh start, and he shot me a weird look. I shrugged and said “It’s not like I’m just a geek, Joe. I have other interests and desires.”
I think it was about that point that he knew what was about to happen. We just sat and stared at each other for a few moments before I leaned in and kissed him softly. He didn’t react at first. It was my first kiss, and I was pretty sure it was his, too, and I was just trying to channel everything I had ever seen in movies or read about. In retrospect, it wasn’t very good, even when he got into it and started kissing me back. I unzipped my hoodie and guided one of his hands inside, and he fumbled with it in a way that all the porn I had ever watched had failed to prepare me for. I would have laughed if the simple fact of a man touching me in such a forbidden way wasn’t such a complete turn on.
I let go of his arm and let him explore my tits at his own speed as I moved my now free hand between his legs. He was rock hard, like a steel bar. He flinched when I touched it, but groaned into my mouth. I’m surprised he didn’t cum right then. I ran my fingers up and down it through his cargo pants a few times before the anticipation got the better of me. I broke off the kiss and slid off the bleachers so I was kneeling in front of him. I struggled with the button for a while before he finally just unfastened it for me, unzipping his fly and pushing down the wasteband of his boxers to allow his rigid cock to spring free, all five inches of it. It was as impressive a cock as I’d ever imagined I’d see. I had to have it inside me.
Porn had taught me that the blowjob comes first, though, so I immediately inhaled the head, ignoring the smell. (Women know the smell of a man who wasn’t expecting to get any that night. Men, wash yourselfs!) I jacked it off the way I’d seen all those actresses do, slowly, with a twist in the wrist. He was in heaven, his head leaned all the way back, moaning his pleasure for all to hear. After a couple of quick pumps, I deep throated it in one quick, easy movement. That was game over. As soon as my lips touched the base of his cock, he exploded. His cum was more salty than I was expecting, and surprisingly thick. I gulped up all that I could, not that he came buckets or anything, but it was still a mouthful plus a bit. Once he finished, I pulled off his cock with a pop and smiled at him. He smiled back, sleepily. I could tell then that I wasn’t getting laid that night.
I got him to rub me through my sweats for a couple minutes (he had no idea what he was doing, but he managed to hit a few good notes) while I tried to jack him back to hardness, but it was obviously not going anywhere. To his credit, he kissed me with his cum still on my breath (guys need to do this more) when it was obvious he wasn’t going to be able to do anything else. I stood and straightened my pants and told him I had to get home. He asked if this was a one time thing, and I just smiled, shrugged, and winked at him. I left him to process what had just happened, but just before I hopped the chain to get back out of the softball field, I turned around, whistled to get his attention, and flashed my tits at him. He about fell off his seat. I went home and told my parents I was going to bed early, which wasn’t unusual for me. When I got to my bedroom, I shut off the lights, stripped down and, for the first time, frigged myself to orgasm while thinking of my very own sexual encounter.
Source: reddit.com/r/eroticliterature/comments/b3t5ua/how_i_almost_lost_my_virginity_fm_repost_blowjob