How I Lost My Virginity... Well, Sort Of. | 2016

One of my close friends in high school introduced me to her senior friend, I was 16 and he was 17 at the time, and somehow we started talking pretty often. He'd hit me up at the oddest of times, and it was really awesome as a friendship, he was cool, and treated me as a human, like so few men in high school do. We hit it off immediately. I had a reputation for being an absolute whore in high school, even though I was actually a virgin. No one knew I was, except the friend that introduced me to him. She had found out while feeling me up when we were making out, but that's a story for another time... Anyways, he asked me if I had gotten any recently, and I said no. It eventually turned into a discussion about becoming fuck buddies. I agreed instantly, because I did really want to have sex, the opportunity just hadn't arisen. Needless to say, I was a huge liar in high school, fabricating everything about my life to just about everyone, but no one ever fully caught on, at least not to the full extent of the problem. We arranged a time when his parents would be out of town, and I got driven to his house after a shift at work by my clueless grandma who was told I was going to a friends house for a sleepover. I slipped in the front door, and walked into the living room with a shit load of confidence that must have been convincing, as it was obvious he was nervous. He said he wasn't a virgin, but judging by his clueless fumbling, he was too. We talked for a while, and I eventually went upstairs to shower. I made it quick, as I was eager to get down to business. I wandered into his bedroom, wearing an oversize t shirt, a fancy bra, and some nice panties about 10 minutes later, and he was fully clothed, sitting awkwardly on his bed. I sat next to him, and we flirted, neither one wanting to make the first move. "Are we going to do this or what?" he asked a few minutes later. "Sure," I said. "I was waiting for you to make the first move." "I'm bad at first moves," he replied, not even looking at me. I eventually sat on his lap and pushed him over, and started making out with him. I would guess I had more experience kissing than he did, he was clumsy and occasionally bumped me with his teeth. He started to undress me, but refused to take off his shirt. I was a little peeved, but understood in a way. He was a chubby guy, and not very tall, so I assumed he was very self conscious. I pulled off his basketball shorts to reveal what I assume to be a rather small dick, with a raging boner. "Is it too small?" he asked immediately. "No," I giggled, and put it in my mouth, and gave him the best blowjob I knew how to. I must have nicked him with my teeth twenty times, and eventually, I rolled onto my back, and he started fingering me. It felt awesome, yet horrible at the same time. It didn't hurt, just was annoying. He eventually reached into my bag to find a condom, and we discovered it didn't fit him, after him struggling to put it on, and me eventually helping. He just brushed it off, saying he'd never used one before, and always went bareback. We tried every position in the book; nothing worked. It went in with no pain, but what worked to get it in didn't work for him to thrust. A whole 2 inches was probably usable with the amount of excess fat around his abdomen, and since I have a rather large ass and thick thighs, nothing worked. We eventually gave up, and I went back to sucking him off. He took over after a while, telling me he'd let me know when he was close so I could finish him off. After a long time, maybe 10 minutes of me watching him jerk off, he said it just wasn't going to happen, and threw his shorts back on. I got dressed too, and he told me I couldn't spend the night, and asked if there was anywhere he could drop me off. I expected to spend the night, and had no where to go. I frantically called my friends, looking for somewhere to go, as I could not go home, or my mom would have busted me. Eventually, I found a place to go. We drove in near silence, and he left me by the driveway, without even a kiss. And that's the story of my virginity, even though he didn't know...