First Times at Ridgemont High

There's something about the first time that is incredibly sexy. At least, idealistically. The idea of a perfect first time turns me on.

Probably because in reality, the first time is awkward, and uncomfortable.

Usually.

Can I tell you about the first time I sucked a dick? It was high school, and my best friend, (we'll call him P Diddy for the time being), and I had been out drinking beer and chasing tail. We had already set it up so he was spending the night at my place.

So, we're lying there in the dark, me in bed, him on my couch. I had been fantasizing about him for ages, and had just enough beer in me to feel daring.

So, we start talking, in the dark, about sex. He'd gotten laid a few times, because he was hunky and the women loved him. I was a gangly teenager, and was still a virgin, at age 17.

Anyway, I confessed that I liked wearing girls clothes. He said "Cool", and I don't remember the details, but I ended up showing him my stash of Mom's satin slips. That was that, no problem, he promised not to tell anyone, and back to bed we went.

After a couple of minutes, I said, "If you were to crawl into bed with me, I'd give you a blow job." A few seconds went by, and he slid into bed with me. We lay there for a minute, and then my hand went to his crotch.

His dick was huge. Soft, but huge. And I eagerly went down on him. And he never got fully hard. I didn't know what to do, but hold this big soft snake in my mouth, until my jaw started to hurt.

Then he went down on me. And I couldn't get it up. Sheesh.

So, I offered to let him fuck me, but, as you can already guess, there was no penetration, because there was no irresistible force to push through the immovable object that was my asshole.

He went back to the couch, and nothing was ever, ever said about it. After high school, he joined the Marines, and I didn't see him again until our high school reunion. Where nothing happened.

(Although there was a rumor going 'round that while he was stationed in the Philippines, he was shacked up with a couple of shemales.)

See? Awkward. But, it got a little better. At least with giving blowjobs.

Now, my other first time experience was good, but unfortunately, was my only experience.

In college, I'd fantasized about a guy in my dorm, about 3 doors down. We'll call him Antony, for the sake of the narrative. If I had to label Antony, I'd use the word "twink". Well, I fantasized for years, but never did anything, because while he was twinky, he always seemed to have a girlfriend.

Heh.

Senior year. He's living off-campus, with his old roommate from the dorm. I'm living off campus with two friends. There's a kegger at my place. And our keg parties were pretty much what you'd expect. Lots of noise and cheap beer.

My ex-girlfriend shows up. The one I was still pining for. (Still carry a bit of a torch for her today, despite my best intentions.) At one point, she grabs me, pulls me into my bedroom, throws me on my bed, jumps on top of me, and kisses me. For about 2 minutes. Then jumps up, says something to the effect of "I'm sorry, I'm sorry, I'm sorry. This just isn't going to work. I'm sorry." Then, she leaves.

I know, right?

I put on a brave face, and return to the party. Some time later, I'm feeling drunk, tired and sorry for myself, and slip into my room, for a breather.

Antony comes in, sits down next to me on the bed, and asks me what's wrong. We talk for a bit, and then, he leans in and kisses me. And what a kisser! I fall backwards, and he climbs on top.

(I hope you're seeing the irony here. Not an hour before, I was in the exact same position with the woman I thought I loved.)

Antony and I make out for a while, before I push him off. "Not here," I say. There's no privacy. So, we decide to head to his place. I borrow my roommate's keys, because my car is stuck in a snowdrift, and we head out.

And when I say "head", I mean it. We're not two blocks away before Antony has his face in my lap, and my pants open. So, I'm driving drunk, on icy streets, in a car that's not mine, getting a blowjob from another guy. In my college town, had we been caught, we'd have been shot on sight, I'm sure.

Anyhow, we get to his place, and Antony says we have to be quiet, because his roommate is home and asleep. Well, shit. That sucks.

And so do I. As soon as we're in his room, I return the blowjob favor.

(Antony, by the way, was probably The One That Got Away. I pine for him probably more than for the silly girlfriend.)

We eventually get each other undressed, and into a nice 69 before I manage to tell him that I want him "inside me". Dunno why I like that phrase, but I do.

He puts on a rubber, and positions me doggy style. And it hurts. It hurts like a motherfucker. And I ask him to stop, but I don't want to quit. So, I lay on my back, and have him mount me, missionary style. And it was heavenly. My god was it good. I don't think he came, and I didn't, but I sure enjoyed the fucking.

And after we lay there in the dark for a few minutes, guilt crept in. And I left. And I regret that to this day.

That was the only time I was properly fucked. And I properly fucked myself by leaving.

Every lover with a penis I've had since then, has been a bottom, like me. And I haven't found a top I wanted to top me. (For the record, there've been a couple of women with strap-ons, but it's not the same.)

And not knowing how to end this, I'll just stop typi