I understand your dilemma, having spent a good part of the last 30 years being an "Uber Road Warrior" myself. If you're above the level of middle management, then you should have well-honed instinct and intuition when it comes to gauging the motives and sincerity of others. Use these just as you would while listening to a business pitch.
As you said, the net is full of flakes and it can be very difficult determining if someone is on the level. If your situation allows, it may be easier if you look for guys interested in being “buddies� versus just quick sex connections. This approach allows you to establish a dialogue that you can use to determine if someone is worth your time or not (and can work wonders if you expect to be back somewhere again). However, if you’re only interested in quick connects, use care in describing yourself. Don’t advertise that your situation requires discretion, or allude to your corporate and/or social standing. That is sure to attract a considerable amount of undesirable attention. Instead, just indicate that you’re a business traveler, when you’ll be there, and what kind of action you’re looking for. Also, specify you will only respond to those who include a clear, recent G-rated photo along with any racier ones. My experience has consistently demonstrated that guys who won’t send a face pic for an intro are usually a waste of time. Another thing you can do is try searching a site’s message boards for other postings by that person. If they do post, you may be able to get an idea where they’re coming from before you expend any effort.
I really prefer the old-fashioned approach of just meeting guys in realtime. It’s far easier to determine if someone’s worthwhile when all of your senses can be used for the scoping process. The hotel bar route has been one of the most productive for me, but also hitting places like a nearby pub or sports bar also work quite well. Since I get the impression that you are very concerned about discretion at this stage of your life, I don’t think going to gay bars or other cruising haunts on your own would be particularly productive or comfortable.
Drop by the bar at happy hour, or right after dinnertime. When on the road, guys are often either feeling exuberant, or wanting to forget their day right after work (often this means they're horny). After dinner, guys are usually mellowed-out some and contemplating being bored for the rest of the night (and also probably horny). In either case, just sidle-up to someone who appeals to you. If he’s with a group, discreetly listen to the conversation, and if you see an opportunity to politely jump in, do so. If he’s by himself, look for cues, like he seems lost or bored, and try an opener like “how long are you in for?� or something like that. Engaging a prospect in a cordial conversation that has nothing to do with sex gives you plenty of time and maneuvering room to decide if you want to pursue him and whether he’s interested. And, even if sex isn’t going to happen with him, at least you’ve given yourself an opportunity to relax a bit and possibly catch the attention of someone else who might pan out.
Later in the evening, there’s a far greater likelihood that men at a hotel bar are looking for some action. Again, engage in some polite conversation and see where it goes.
Another tactic is to hit the head when someone you’re interested in does. If you’re alone with him, try the “relief sigh� or say something like “thank heavens for these things� and see if he responds verbally. If he does, then look his way and make some innocent chit-chat. If he’s open to the idea of playing, with you’ll get the message in short order.
Good hunting.
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