I’m meeting “Tommy” in the story in real life this Saturday, but I have no idea how it will really go. He may not even be interested in me. I’ll follow up later with the real story, if it goes well (and anybody cares to read it.)

Though I identify as straight, and have been married over 20 years, I’ve had a curiosity about engaging in oral sex with another man since I was in my teens. The urge to satisfy that curiosity has ranged from a mild, easily ignored buzz in the back of my mind, to an almost obsessive desire, but I never became motivated to actually try anything.

Well, that’s not entirely true. When I was 17, I did talk an older friend, who was bisexual, into having a go at it. It was nervous, adolescent fumbling on my part, and I think he just really didn’t find me to be his type, so nothing “came” of it (so to speak) for either of us. I’d had to have a good amount of beer to even get up the courage to do that, so my being inebriated may have had a hand in my not finding it particularly satisfying.

The urge had recently started building again to the point where almost all of my masturbation fantasies revolved around it. In my fantasies, I didn’t have a distinct person in mind; in fact, there wasn’t really even a face involved. I mostly “saw” a torso with a penis attached, and I licked and sucked the penis until it was over. To add as much realism to the fantasy (and because it has also always been a desire of mine to perform oral on myself), I would on occasion lay in bed and throw my legs over my head, rolling up in an attempt to suck myself. Of course I was never close, but I would masturbate this way until I came, and either let fly into my own face or in my mouth, at which point I would usually swallow some of it. I didn’t find the taste particularly pleasant afterwards, but in the heat of the moment it was what I wanted.

In fact, I often think that if I could actually suck myself, the urge to be with another man would probably go away altogether. But let’s face it; it’s easier to find a man to play around with (or so I thought) than to diet and exercise and become trim and flexible enough to suck yourself off.

Usually the urge would stay with me several days, maybe even a few weeks, but then eventually go away as other facets of life start taking over. But something was different about this time. For whatever reason, I was determined that this time, for good or ill, I would fulfill this fantasy. I was interested in seeing if the reality would be as exciting, once I was in moment. But how does a straight guy, with a reputation in the community to uphold, go about finding someone to satisfy this kind of curiosity with?

I turned to Craig’s List, and searched in the “Casual Encounters, m to m” section of the Personals. A lot of the ads were from aggressively gay guys who wanted to “ream” and “pound” and whatnot, and I just wasn’t interested in that. I was looking for someone more along my lines: married or attached, curious about oral (only), and willing to experiment in comfortable manner. I didn’t care at all about looks, and size wasn’t an issue as long as they were within a range of normal. I didn’t want a toothpick, but I didn’t want a salami either.

There were some promising ads, so I responded to a few with my stats (6’1″, 240, not really fat, but pudgy, 6.5″ cut, medium girth, etc). Most didn’t return my reply, and those that did would seem interested at first, then suddenly all communications would stop. I finally put out my own ad, and received a number of responses, which was encouraging. Most of them did not meet my criteria as I described above, but there were a few gems in the trash.

I had a promising conversation with a man who was also curious, and who’s wife wanted to watch us and maybe join in at some point, but that would be up to her. Once again, after some email and picture exchanges, they just dropped off the face of the earth. I was disappointed, because having a woman involved, even if she was only watching, seemed like a perfect bridge between what I was used to and what I wanted to do.

After that, there were a couple more false starts, and I eventually decided Craig’s List just wasn’t going to work. A lot of the ads ran over and over, and it just started seeming like most of them were insincere, or perhaps a scam of some kind. But I still had the urge.

Finally, I decided I would have to call in some expert help. I contacted a former co-worker, whom I knew to be gay, with the intention of asking for his advice on how to find someone that meets my criteria. Tommy (as he’ll be called here) didn’t meet my criteria, being openly gay (so definitely not straight but curious) and “married” to another guy. But I had the feeling from when we worked together that he found me attractive, and I hoped that he would have some insight on how to find the right situation. Perhaps, I reasoned, he even knows other married men who are curious and looking for a similar set of circumstances as I am.

I explained to Tommy that I’d like to meet him for a drink or something to get his advice, and he quickly agreed. So quickly, in fact, that I wondered if he had some clue, somehow, of what I was going to talk to him about. I considered the possibility that, when I laid out my situation to him, he might volunteer. At first the idea seemed a non-starter, not only for the fact that he didn’t meet my criteria, but I also didn’t know if he was really interested in my or not. And even if he were interested, being in a relationship with another man, I didn’t know if he would be the type to cheat.

However, as the days counted off to our “date”, as I’d started thinking of it, I realized that there were some other aspects of him that were appealing. We had a good rapport, and got along well. Plus, I just felt I could trust him, not only with the secret I would be revealing to him, but that, if we did do something together, he would respect my boundaries and not try to rush me or be overly aggressive. Besides, if he was interested, this would be perhaps the quickest, drama-free way to go about getting what I wanted.

On the day we met, my wife went to an event that I knew would keep her busy for at least three, and up to four, hours. Still, I had an alibi for being away from the house, just in case she came home early or called me to see how I was getting along. Everything was set, and I left soon after she did to meet Tommy. I was as nervous as I’d ever remembered, perhaps even more so than my first date as a teenager.

When I got to the grill, I looked around and spied Tommy at an out-of-the-way table in the back corner. This added to my suspicion that he had at least some idea of what the conversation would be. I approached and we said our hellos, shaking hands. I don’t know if he noticed how damp my palms were, but he didn’t say anything about it.

We made small talk as we looked over the menu. I finally ordered a beer and a burger, and Tommy ordered the same. When the beer was set before us, we raised our glasses to one another, and had a drink. With those social niceties out of the way, Tommy said “So, what did you want to talk about?”

Now I had been rehearsing how I would begin for the past week, and had gotten no further along in finding an appropriate manner during that time. I didn’t want to make it seem like I was asking him to have sex with me directly, but I didn’t want to be so subtle that he wouldn’t think to ask me if he would do.