Regrets for Wasted Time

There are some internet hookups that don't exactly turn out like you want them to. One hookup led me to a boyfriend of two years that I still keep in touch with (and love just a little bit)--an awkwardly tall man with a skinny frame and a thin face that changed shape when he smiled. But this isn't about him. The problem with a hookup that turns into something more with a guy like that, it's always because the guy is a disappointment.

There are few more disheartening experiences than realizing on the stoop of a strange man's house/apartment that the picture he had online was no as sexy as he actually is. What do you do? Do you come in? Do you say "No, thanks," and walk away? Do you you just grin and bear it while you go through with the dirty deeds you both have agreed to do with unspoken words? For the first year, I would let myself have sex with the ugliest most unappealing men just because I said I would.

Once, I was cruising on the internet for a hookup. I was horny, and I was willing to jump at something less than perfect. Shoot, whenever I look for perfect I usually get barely acceptable. I should have known looking for less that perfect would yield creepers and weirdos. And that's exactly what happened.

The usual old men started prowling for my young ass, and I was thinking about it. The youngest that I was getting interest with was a thirty year-old. The most intriguing part was that he was a red-head. Now, let me admit that this was when I was first trying out the internet as a resource for sex. The options were limited, and I was only 17 and on a dial-up connection. I could never let my parents know, so the window for searching was small. I had to work fast and quickly. The redhead would do, and I was turned on by the idea of getting fucked by a fire-crotch. I agreed. His place would be available in an hour. He gave me the address. I wrote it down. I deleted the gay websites from my browsing history and went to a dozen dummy sites so my parents wouldn't get suspicious.

I went into my room and played around with my dick while I read a few gay porn stories I had printed out one day. I was getting close, so I decided to stop, and hoped it was time. It was thirty minutes until the guy would be free, about ten or fifteen minutes before I had to leave. I figured it would be better to leave and come with a cock full of cum later than to show up and stay soft the whole time he was fucking me. I decided to go to a Borders and sneak a peak at one of the novels in the Gay and Lesbian section.

I drove my car to Borders and when I got to Borders I was still 15 minutes early for my hookup, so I pretended to browse the fiction, and waited for an appropriately unnoticed moment to grab a book from the gay section. I grabbed one and walked a few aisles away from the section and pretended I was looking at a novel in the mystery section.

It was the first gay animated porn book I had ever seen. It was so hot. When I first opened the book I immediately started to get an erection. It was so graphic, I immediately shut it and looked around to see if anyone noticed me or the book, or my tenting pants. There didn't seem to be any suspicious glances around. I opened the book and snuck another peek. There was a series of pictures of a guy bouncing up and down on another guys cock. I will always remember that picture because as soon as I saw it I had to touch my dick.

As soon as I touched my dick I came in my pants. It didn't expected it. I froze mid-aisle as someone passed, freaking out, and desperately trying to hide the book, immediately crouching to hide my raging hard-on, the semen in my short, and pathetically trying to avoid shouting with ecstasy. Even with my mouth shut, I knew I let out a queer sounding squeal. A guy further down the aisle definitely noticed my strange noises, but didn't seem to think much of it.

I remained crouched down, wriggling my toes, counting in my head, and trying to do anything to keep my mind off my cock so that it would soften. It seemed to take minute after minute. I would look down and still notice the bulge of my cockhead in my shorts and continue counting to distract my mind from the hottest orgasm I had thus experienced in my life.

After my erection subsided I walked as quickly as possible to the bathroom. I had stashed the porn book behind the shelf of books I was looking at, behind a couple of Ken Follett mystery novels. When I got to the bathroom I found what I had expected. I washed off my penis and pubic area of cum. My underwear was a mess. I took the boxers off and when no one was in the bath room came out of the stall and tossed my underwear in the trashcan. I didn't even want to be the unsuspecting visitor who might have noticed my cum-soaked drawers in the trashcan of a public bathroom.

"Fuck!" I thought. I was late for my meeting, and I had cum. This meeting was going to suck. I ran to my car and drove as quickly as I could to his place. He didn't seem surprised that I was late, but I was surprised by him. He was indeed a redhead, but I could barely tell because he was so bald and his hair was so light. He had an (unfortunately) well-defined beer belly and acne scarring his face. When he took off his shirt his back had even worse patches of red blotched and white-headed pimples, and I was afraid to touch his back. He chest was covered with a thick mat of almost blond hair and a pubic region that was not trimmed. (I prefer trimmed pubes.)

I couldn't say a word. He kissed every part of my body and I couldn't reciprocate. The first thing I said when he was about to fuck me without a condom was, "Aren't you going to use a condom?"

"Oh shit," was all he said. He seemed mad I noticed and/or cared. He got up and put a condom on. Maybe he was mad, but I was not turned on. We fucked in the missionary position, and I voluntarily turned around to doggie style so I wouldn't have to look at the ugly old fuck who was fucking me. How did I let this happen? Was I too overcome by coming accidentally in public to say no to this guy? I had never said no to a guy before. Was this just a result of being too afraid to reject someone? Was I so desperate for a cock in my ass that I didn't care what was fucking me?

I left with my ass feeling fine because his dick wasn't that big. I left with lube still in my ass. I left because he was turned on by the (unintentional) fact that I came commando. I hadn't come, even though he stroked my dick so hard it started to hurt. I left saying just, "Thanks man," without a smile on my face.

I guess since his response was, "Anytime," I could imagine I wasn't exactly the most arousing fuck. But I know I'm cute, and I know I'm a pretty good fuck, and I know I'm probably better than his average. So what I he knew I knew he was ugly. Should he appreciate the screw with good looking guy anyhow? Is that not how that works?

I didn't know anything then. He was probably the third or fourth guy I slept with in my life. He was one of the early ones. All of the early ones leave an impression. All of the men I have actually slept with still leave an impression, but the first ones were particularly important.

I left thinking my regret was first actually having sex with someone I clearly knew I did not want to have sex with. I left regretting the waste of time. Why do I embarrass myself for some satisfaction?

Sometimes I don't understand why I do the stupid shit I do, or have done.

PS. Thanks for the comments! I really appreciate the appreciation, and even the criticism.