Where it happened: His bedroom
Langauge: English
Sex: Female
Rating: 5
Category: Straight
The guy I had sex with was Ben. He was two years older than me and getting ready to go to college. I was 16. We’d been on again/off again for about 5 years. (Which is just crazy for middle school/high school standards) But in the end I had decided that he didn’t make good boyfriend material. This was probably due to the fact that he was incredibly selfish and EXTREMELY feminine. I mean, this guy had the entire gay persona about him. Name any quality of a stereotypical gay guy, and Ben had it.
Anyway, it was apparent that he still liked me. And while I was no where near wanting to date him again, I did still like him too. And once while we were backstage at a summer play rehearsal, I had to seriously fight the urge to jump on him right then and there. Despite his less than attractive face and body.
Two weeks later I sent him a message on facebook saying, “Okay this is going to seem really really weird. But I remember you once saying that you’d be willing to have sex with me. Are you still willing?”
After a few days of awkward messages we decided to do it. We were both virgins and both figured that we could make this a summer to remember.
So I snuck out of my house one night around midnight. His mom was out of town and his dad was working night shift. I drove to Wall Greens and bought some condoms. The guy at the register just sort of shook his head at me, which hurt. But hey, at least I was using protection, right?
I got to his house and he answered the door. All we could say to each other was, “Hey.” The awkwardness hung in clumps in the air. And the grocery bag containing condoms didn’t help any.
We walked up to his room without talking. When we got there I made some retarded joke about something to ease the tension. I don’t even remember what. He kind of smiled but didn’t say anything. So we stood and looked at each other for about ten seconds. And finally I got up the nerve to walk toward him. I looked into his eyes, put my arms around his neck, and kissed him.
That led to some more boring kissing and before we knew it, we were laying down on his bed with me on top of him. His hands went slowly up my shirt and he daringly pulled it off. I did the same. But this whole situation was still completely awkward. So I got up, hid my breasts with my arms, and turned off the light.
Yeah, that was better.
We went back to kissing. His boney chest was warm against mine. Then, uncharacteristically, he rolled over on top of me. Since I preferred to be submissive, it really turned me on. I’d always fantasized about him tying me down and having his way with me. Of course I realized this wasn’t going to happen, especially since he too liked submissive. So him on top of me was good enough.
He unzipped my pants and pulled them off. Fortunately (haha) my panties came off too. He started to finger me. And to tell the truth, I was actually proud of him that he knew where my vagina was. (my last boyfriend totally didn’t.) So he pleasured me until I came for the first time in my life. It was intense. The orgasm rattled its way through my entire body and I moaned. Geez. We should have started doing this sooner.
I then took charge and rolled him over so that I was dominant. I might like being submissive, but at that point in time, I felt like making him my bitch. I pulled off his jeans to reveal his sickly pale legs. Gross, right? And then I pulled off his boxers to reveal a four inch penis. I didn’t let my disappointment show. I hadn’t expected much to tell the truth. I just closed my eyes and blew him like the slut I was. When he came and moaned my name, I had to stifle the urge to laugh. Sorry, but it was really funny. Mostly because I’d never seen him so broken down and he sounded like he did when he imitated a scene from Legally Blonde the Musical. (Told you he was gay)
Afterwards I broke into that condom box and later climbed right on top of him so that I could shove him inside of me. At first it hurt like hell and it took a couple of awkward tries for it to go in at all. I let out a tiny scream of pain when my hymen tore. But after that it was all good. No really, it was good. Surprisingly enough. His hardness was in stark contrast to my insides, but I loved it. I rode him like my whole life depended on it.
At some point he placed his clammy hands on my hips. Which was a little sickening, but at that point I was already orgasm-ing and hardly noticed. He came and as soon as it began, it was over. We were no longer virgins.
We had sex so many times that night that we didn’t stop until we ran out of condoms. It was amazing. And believe it or not, my bondage fantasy came true. =D
I left around 4 to go home and my parents never suspected a thing.
When I told my friend Alyssa what had happened, she almost threw up. But then she just laughed and said, “Well since you both are sticks, I’m surprised you didn’t start a fire.”
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