Tuesday, August 6, 2013

Too Many Questions

When it comes to online hookups, it’s usually pretty easy to tell whether the other guy is serious or not. Usually it boils down to one thing: whether they ask too many questions, and about the wrong things.

This last Sunday I placed an ad stating I wanted to give head. Nothing complicated. Nothing too weird. I said I just wanted to walk in, take down a guy’s pants, suck him to completion, swallow the load, and get the hell out. (Okay, I didn’t actually state the very last part. I hoped it would be inferred.)

After I’d discarded the overwhelming number of replies over my photo that of course read with variations on, Hot dick! You should let me suck it!, I was left with a couple of promising possibilities.

I wrote the guy who was most local first. His first reply had asked, Are you looking for now? I wrote back that I was indeed. What’s your body like? he wanted to know. Are you fat, fit, overweight, what? I wrote back that I was six-three and a hundred and sixty-five pounds, and that I was actually pretty lean, as he should have been able to tell by my photos, which had been taken that morning. He wrote back another email saying Well I don’t want you showing up and seeing you’re a fat slob.

Are you looking for now or not?, I wrote. He wrote back, I notice you didn’t answer my question about whether you’re a fat slob or not. Photos can lie you know. At this point, I figured the guy was just dicking me around. Out of politeness, I wrote him and said that I had in fact answered his question in my second email, that my photos were current, and thank you, but I was going to look elsewhere.

Five minutes later I got another email from him. So are you looking for now or not?

I didn’t answer. This was not a guy who was going to hook up.

A guy down I-95 seemed a little more promising at first, when he sent me an email saying he could host all afternoon and needed someone on his big dick soon. You got any more pics?, he asked when I wrote and told him I was available at that moment. When I sent pics, he wrote back, Any more? Face? I pointed out that I’d sent a face pic in my last email, and sent another. Any pics of your ass?, he wrote.

I wrote back declining to share one of those, because he wasn’t going to be seeing my ass, much less doing anything with it. You got any videos of yourself? he wanted to know.

I just stopped answering.

The last guy was a Puerto Rican kid. Early twenties. Fucking hot, from his photos. Huge dick. I mean, easily nine inches of uncut skinny dick that he said he wanted sucked. I could cope with that. Are you free now?, I asked.

Do you have more pics?, he of course asked. I sighed, considered just signing off and going about my business, but in the end gave him a chance and sent a few mixed X and G shots. He replied with a few more of his own, which at least gave me slight hope. Are you discrete? was his next question.

I replied that I was very discreet, and used the correct spelling. How far away are you?, he asked. I told him it was no more than ten minutes from my place to his. Will you suck me deep down? he wrote back. I sighed, pretty sure that every new email was reducing my chances of actually seeing that Puerto Rican dick by about twenty percent. But I told him I’d suck him deep down. Can I take a video of you sucking me? was next.

Look, I’ve got about ninety minutes, I wrote him. Do you want me to come over and suck you now, or should we put it off until later?, as in never, I was secretly thinking. But then to my surprise, he gave me his address and told me to text him after I’d parked. I was out the door like a shot before he changed his mind.

The area in which I live has these odd and unpredictable outcroppings of granite that jut out of the earth like giant building-sized teeth; they’re massive fuck-yous from some ancient glacier that just dropped them millennia ago. It’s easier to construct urban areas around the damned things than excavate or destroy them. And this guy’s apartment building, I found out, was build atop one of the rockiest and highest plateaus in the city. I had to park at the bottom of his street, walk a steep incline to his parking lot, walk another incline to his building, and only then did I see him coming toward me—down a long and twisty staircase. I’m not totally out of shape. I do a lot of walking. But I was already winded from the uphill climb, and when I saw I still had another small-sized mountain to scale just to get to the door of the apartment building, my heart sank. But I followed him up and even assayed another flight of stairs to get to the second floor.

By the time I was finally in his apartment, my heart was pounding like I’d undergone an old-fashioned stress test at the doctor’s office. “We have to get it done before my roommate comes back,” he whispered to me.

“When’s your roommate back?” I asked. He shrugged. Which didn’t allay my anxiety level, let me tell you.

Now, as I said, in his photos the guy was hot. I mean, super-hot. In person . . . not so much. I didn’t get a general sense that his photos were old or manipulated. I think he merely photographs spectacularly well, given his looks. Which weren’t ugly, exactly. But they surely weren’t pretty.

I wasn’t there for his face, though. I yanked down his gym shorts and got my mouth on his dick. “Suck it deep,” he commanded. Not a hard order to follow, since he was soft. I ran my tongue around the inside of his foreskin and took him down to the root, slobbering over his dark-skinned stick and letting the tip of my tongue tickle his nuts when I hit bottom. He started to get hard almost instantly.

“Get naked,” he whispered.

I took my mouth off his dick. “I’m not getting naked if your roommate is going to walk in at any second,” I told him.

“Show me your dick,” he begged. I was just wearing a pair of flimsy sweat shorts. No underwear. Big cock ring. I let the shorts fall around my ankles, and showed him my hard dick. “Show me your ass,” he pleaded. I complied, then started to kneel between his legs again. “Come on me,” he whispered. “Cum on my dick and lick both our loads off.”

And then—I’d been in the apartment maybe for all of a minute and a half at that point—he started to dribble a very small load all over himself and the carpet. Mostly the carpet. I stood there, still half out of breath and astonished at the lightning speed with which this kid shot, just kind of gaping at him. “Come on me!” he said again.

Well. I might as well get some kind of nut out of it. I stood between his legs and beat at my dick. “Hurry,” he ordered. Because that’s the way to get me feeling sexy, of course.

I let go of my cock and stooped to pull up my shorts. “I think I’m just gonna head out. . . .”

He cursed en español. “I got cum on the carpet!” he yelled. “Fuck! I’m going to be in trouble!” Like he’d been stung by hornets, he jumped up and ran to the kitchen, presumably for something to wipe up with. He returned wild-eyed. “You gotta go! My roommate’s gonna be home any time!” It wasn’t even until I was out the door that I thought to check for my keys. Luckily I had everything.

Gentlemen (and ladies), learn a lesson from me. Sometimes it just behooves you to honor your instincts. And sometimes it’s just doesn’t pay to leave your house. Even for a nine-inch Puerto Rican cock.


  1. Sounds like his roommate was a relative or parent O_O

    1. Yeah, I was thinking the same thing. I was guessing brother or cousin, from the furnishings. They didn't really seem old enough to belong to his parents.

  2. Your ability to take any encounter, however mundane, forgettable, or just plain annoying, and turn it into an engrossing, witty, humorous tale(or serious and thought provoking, if need be), is a real gift.
    Thanks for sharing your gift with us.

    Another Rob

  3. At least you didn't have to travel far for nothing other then an uphill stress test.

    Like what was said the other day with your craigslist blog, people just don't read or pay attention. How hard is "...walk in, take down a guy’s pants, suck him to completion, swallow the load, and leave" to understand.

  4. deja vu all over again! i've had the same experience - but not a well told as yours.

    i make my ads clear too, and it amazing the number of guys that don't want to read, or don't seem to grasp, the concepts embedded in 25 words or less. if you can't seal the deal with a quick exchange of photos, and address and a time then move on.

    some of the hottest experiences i have had come from quick, easy exchanges where we both seem to want the same thing - me on my knees sucking him off.

    i've whittled it down to "u come - i suck - u cum - u go" and they still can't figure it out! lol

    1. I seem to run into trouble whenever I look for anything outside my usual wheelhouse. If I put up an ad asking for bottoms to savage, I'm pretty sure I could get one easily. Showing my dick and asking someone to dominate it just doesn't seem to compute with guys. I tried putting the ad up again this week, and the first response I got was from someone asking if I ever rough up guys for cash with my dick. (True story.)

  5. In contrast to gh_lovr, I haven't had the same experience, or anything close to it. But I still enjoyed reading your account of this frustrating encounter. The whole concept of having sex with total strangers is far out of my world, such that most of what I imagine knowing about the subject comes from your blog. No doubt there are other sources, but, as anon. 10 am suggested, you have the gift for describing the phenomenon as it is, and not as it's idealized in gay porn.

    1. Thanks, Steve. I really appreciate it.

  6. I'm always mystified that the zillion question guys really get anything out of that kind of time-wasting. I know exactly what you mean here, that feeling of "Question number three suddenly made me realize we are just not going to fuck." It's not even always the same question, or even the same kind of question; it's just that if someone was really turned on and wanted to screw, they wouldn't ask it, they'd be saying something else. This behavior has seemed more and more common lately, or maybe I'm just getting older and crankier and less tolerant of it. But honestly, for those dudes, how exciting can the exchange "how big is your dick"/"n inches" be? Do they sit there all night doing that to various guys? Aren't there any cartoons on? Wouldn't it be more fun to just take a nap?

    1. You nailed it with this: "It's just that if someone was really turned on and wanted to screw, they wouldn't ask it, they'd be saying something else." On the money, CoolTop.