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Awkward

Age when it happend: 17
Where it happened: His parents' house
Langauge: English
Sex: Male
Rating: 9
Category: Straight

I was sleeping over at Tom’s house. Our two friends were staying over, too, and we had all decided to crash in the lounge upstairs. Our one friend, Joe, had a cold, and fell asleep with a box of tissues under his arm. Our other friend, Lou, was the most awkward and conservative guy I’d ever met. So Tom had just (finally) come out to me after I told him 6 months earlier that I was gay and had a thing for him. Lou and Joe were asleep, and we started to kiss. It was terrible; he was one of those kissers who puts your entire mouth in his mouth, and you get all saliva-y all over your face and lower nose. But whatever, I was so excited to finally be kissing a boy, and we had been best friends for so long, I really was in love with him. What I didn’t expect was for Tom to go further. Ocean’s 11 (the new one) was on TV, and with Brad Pitt, Matt Damon and George Clooney affecting our adolescent libidos, I should’ve known it wouldn’t end at just kissing. He pulled my shirt off my head and snuggled up behind me. He was kissing my neck and the back of my head, then he reached down my pants. Of course I was hard, and no one had ever touched my dick before. His fingers were soft, and he wasn’t using much pressure at all, nor was he moving too fast. It was slow, and if I turned my head hard enough, I could kiss him while he jerked me off. He humped my ass as he jerked me off, until finally, I knew I was going to cum. I had never orgasmed so intensely in my life, it felt incredible. I caught all of my ejaculate in my hand, and then it hit me: there were two awkward teenage straight guys in the room with us, and the tissues were being held hostage by a snoring Joe. Tom slowly crept up to Joe, grabbed a throw pillow and snuck it under Joe’s arm, grabbing the box of tissue in exchange. Joe didn’t wake up, and Tom cleaned me up. I asked him if he wanted me to reciprocate, and he refused.

We ended up dating on and off for a while. He was the first guy I ever loved, and a part of me always will love the person he was. Oh well …

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