Where it happened: His room
Langauge: English
Sex: Female
Rating: 3
Category: Straight
I’m going to give you a description of myself just for the sake of painting a picture. My name’s Leila and a year and some months ago I had sex for the first time. I’m 5’4, with an hourglass figure, a nice pair of C cup boobs and very long reddish brown hair. I hope I satisfied the male readers, so here’s the story.
I knew for a while I was tired of being a virgin. Of course I wouldn’t give it up to anyone. They would have to be hot, at least average in brains and also willing to leave me the fuck alone when I got what I wanted from them.
The opportunity presented itself one fine Friday evening just as I had gotten home from my after school classes in the form of a phone call.
Derek was probably the hottest guy in my year in high school. Of course I didn’t look around a lot because most guys were decent enough to ask for a relationship and I didn’t want that. I never really knew Derek until we were sited next to each other. Through our small talk I found out he was actually smarter and much less “idgaf” than what he let people think. I eventually started liking him and he started making moves. Sexual tension was high, body parts were being grabbed and I was craving him like I had never craved anyone before. So, back to the story.
Derek called and asked me if I’d like to go over. Obviously realizing what that meant I accepted and having only half an hour to get there I decided shaving my legs was probably a safer bet and would take less time, leaving my crotch a bit hairy, but oh, well, it was trimmed at least. Still I wasn’t sure we’d have sex, although it was rather obvious.
He met me a few block away from his place and instead of hello, kissed me. That was the first time he kissed me, and it was also the second I realized I wouldn’t leave there a virgin. We walked to his house and as soon as he closed his front door he turned and pulled me up to him, making me wrap my legs around his waist. He kissed me again and then carried me to the living room. Setting me on the couch he lost no time getting on top of me and pulling my coat off. Hands were everywhere and we were kissing for quite a while. When he broke the kiss he asked me if I was ok with us hooking up every once in a while. I asked him in what sense he meant it and when he said by staying friends, I told him I though it was perfect. He kissed me again and then continued to ask me whether I’d like to go the bedroom. I said sure, and pulled him back in for a kiss, climbed in his lap and broke our kiss one last time by saying “oh, by the way, I’m a virgin”. He seemed a bit shocked (everyone seemed to assume I wasn’t a virgin since that ass was too hot to not have been tapped), but he said that was ok and led me to the bedroom.
Once there he took no time striping me, quickly leaving me only in my bra. He took everything off, and had me sit on the bed and asked me if I would suck him off. I said sure and he came to stand in front of me. Now I had never touched a dick before in my life, but I wanted to be good so I’d watched a few videos of how to give good blowjobs and it was time to use my theoretical skills. I took his dick in my hands and slowly put it in my mouth. I went up and down, sucking. Then took a break by licking his shaft then back again. I used a little trick I learned in one of the videos and he soon asked me to stop because he was getting very close to cumming. He left me for a second to put on a condom and then came back and got in bed next to me. I was lying on my back and he gave me a quick kiss before his mouth traveled down to my nipples. He licked and kissed and sucked lightly and I though that was the best feeling until he started doing the same to my clit. He didn’t stay there too long, playing with my clit and teasing me with his finger in my pussy. Soon I was a hot, wet, nervous mess and all I wanted was for him to get on top of me and fuck me till I scream.
Soon, he positioned himself between my legs and asked me once again if I wanted this. I said yes and he slowly started entering me. Oh, the pain. I closed my eyes and gripped his pillow thinking “I’m not made for this”, but I would have to bear it, so that I never had to feel it again. He had stopped, seeing that I was in pain, but I told him it was ok and he kept going. Too bad he apparently hadn’t had sex in a while because he was done in three thrusts. When he pulled out there was no blood though, which was a relief. I just waited for him to throw away the condom and clean up, and when he came back we just talked a bit. Then we started making out, and when he was finally hard he asked me if I wanted to be on top. I warily said ok, but didn’t expect I would be stunned by the pain. He tried to show me how to move but it was plain and simple that I couldn’t move at all. Everything hurt and I was just sitting on him. I told him it wouldn’t work, so we stopped but this time he got too nervous causing his *ahem* to go down. I was kinda disappointed and he was very embarrassed, joking about how he should have had masturbated more. I was still in pain and tried to make him feel better, unsuccessfully. It was just awkward and weird so I told him I should be going and he walked with me to the point from which he picked me up.
I still to this day don’t regret my decision to hook up with him, although I was quite disappointed we never got to try again. I thought my first time would be a time to learn but I didn’t learn anything and so I knew I’d be awkward the next time I had sex. That was really the only disappointing part, I expected the awkwardness and I know guys have technical issues sometimes so I didn’t mind that part. The only thing that really stands out in my memory from that night is the pain. The worst pain I’ve ever felt which led me to the decision that I’m better off adopting in the future. But it was rather fun before that. Days later I overheard some girls talking about him, one of them saying “I don’t understand why he doesn’t want me. He won’t even ask me to come over, not even with other people.” which made me feel great about myself considering this girl had been making moves on him all year. I’m still smug about it. But hey, I fucked the hottest guy in my school. He hadn’t had sex in a while before me (his words and actions prove it to be true). I fucked the hottest guy in school and nobody knows. 😀
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