MscleLovr

I appreciate that you gave a fairly succinct description. So forgive me for summarizing but surely the question is Do you want to see him again? Only you can answer this. It’s obvious you enjoyed the encounter, and the aspect of voyeurism was novel to you and gave an added frisson. Decide what you want first. The business aspect is secondary. Just be precise and specify that you want the boyfriend to watch (or participate) and mention that you’re now hirsute.

Personally, I see that as an endorsement. But then I’ve always enjoyed the company of handsome men, with fit bodies, who need financial support.

Why would he need us to do so? Surely he gets a significant bequest in your Will 😀

I know what you mean….but 40 years ago, Mykonos was VERY gay. And at that time, gay men and women were not so visible elsewhere. It’s still nice but it’s not what it was. My personal feeling is that something was lost when the heterosexuals began to arrive en masse. Key West too was changed in a similar fashion to Mykonos.

I understand your views and what you wrote @wanderlust307 I’d suggest, however, that some of the many reasons are not good for many holiday makers. So visit Mykonos if you like to party, enjoy crowds and want to spend lots of money on a hectic vacation. My reasons to avoid Mykonos include 1. there are more interesting/beautiful places to visit in Greece 2. Other countries have more unspoiled islands in the Mediterranean, eg Croatia, Italy and Spain 3. there are many interesting resorts with better food, even the South of France is cheaper than Mykonos

I always enjoyed 3somes. I’m a top only, but I can certainly relate to what the OP described. Sometimes with a couple of attractive professionals, I happened to prefer one man over the other. It might have been a mix of chemistry, better personality or a skillset in bed that meshed with mine. I’m sure we’ve all discovered that one man loves to suck cock but won’t rim, while another man kisses deeply with tongue and is an eager bottom. I had a similar difficulty as the OP a few years back. Two very handsome, fit-bodied young men worked together. I had a great time and I waited until one guy was in the shower and I was alone with the man I preferred. I simply said I’d love to spend time alone with you and asked how to arrange that - he just gave me his cellphone number. (He also aroused me: he told me he’d enjoyed being topped and wanted to see me again very soon; and he added ‘next time I’ll swallow your load’). I’d caution against that, unless you are an exhibitionist. Citing the duo above, my preferred guy worked very well solo on our dates. But each time, he stressed to me that I must be discreet and not tell the other guy what we did. It turned out that this handsome muscleboy was compliant and readily did things for me that their ad said they did not do.

I totally endorse what @Charlie wrote. Do it while you’re still healthy and feel fit and capable. If you wish to take ‘baby steps’, I’d suggest you first take a lengthy vacation say 3-6 months. You’ll get a good idea of the place you choose and can decide whether you want to visit for longer and travel within that country. FWIW (1) I lived in San Francisco for over 2 years, even tho I’d always preferred Sourhern California - I enjoyed my time in SF very much but my preference remains unchanged. (2) I lived in Buenos Aires for more than a year. I had some acquaintances there and I made a couple of friends, and I speak and read Spanish at what’s classed as ‘an advanced level’. Again I enjoyed that time and I had a lot of fun. But the problems of living there (bad pollution, high level of crime - I was not a victim, but I witnessed street crimes, general difficulties with banking and bureaucracy) led me to decide that was enough. (3) I lived in Amsterdam for more than a year. I made strenuous efforts to learn Dutch and that helped me immensely to make friends and access the quite distinct culture. I enjoyed it and it’s a useful base if you wish to visit Europe more widely I’d recommend the Baltic countries or Spain first as English is very widely spoken. It’s relatively easy to learn Spanish, and you could learn some basic phrases in the Baltic countries as it won’t be expected but it will be appreciated. And on a geopolitical front, I’d visit the Baltic countries before Putin decides to expand his territorial ambitions and embarks on another military adventure.

What a bad experience @Axiom2001 I’m glad that you were able to escape safely. This is why, when visiting strangers or an area I’m unfamiliar with, I take bottled water with me. It’s also the reason why I offer first-time visitors reassurance and an unopened bottle of water. My motto is Better Safe than Sorry!

I can’t say specifically about Peachyboy, but I’ve contacted other IG models via polite, generous, discreet DMs and had good success. Nick Topel was mentioned earlier by @jazboy as not being amenable. Nick has a great physique. I am surprised by his refusal as he often socialises with gay men. He has a couple of close friends (who also are gym-rats) and I know that his friends have made themselves available for $2-3000 (to include travel time and costs).

I can’t help with a name. A simple Google search reveals various such providers in San Diego.

I will not disclose any of the information shared privately but it’s now clear that @robberbaron4u and I were talking about the same man. I feel @robberbaron4u that you have a more generous nature than I possess. I would simply cut off all contact with this man. I think it’s potentially dangerous to have such an individual in your life, even if only as an acquaintance.

I feel that’s very unfair of you @DrownedBoy You might have paid for a trial session and seen whether they carried out a thorough cleaning of all your “nooks and crannies” Given today’s inflationary backdrop, the OP @JayJayStarr is rightly concerned about the cost of cleaning products. Employing naked cleaners would obviate the need to strip-search them for any products they might have purloined.

If I read this correctly, even with “relocating from the West Coast”, I very much doubt that this man (now in his 50s) with just over $1million, will be able to maintain a large, high-living existence for long. I have heard a similar tale once before. I wonder if this man you describe was latterly a real estate agent? I ask because there was some considerable gossip that he had (inadvertently or deliberately) hastened the demise of both his older partners. My concern here would be for you @robberbaron4u since this man may want to attach himself to you, just as a parasite always seeks a new host.

I spend some months there each year. Aside from seeing a male stripper at a friend’s private birthday party, I’m not aware of any. I’ll ask my local gay friends and report back if they know of any

That’s true of South Africa in general where equal rights for gay people are enshrined in the Constitution. Even there, social acceptance varies: a great deal of the tolerance reflects tourism, consumer spending and urban interests; there’s still homophobia in rural areas. In Kenya, I’d urge you to follow the advice of @dcman above IF you insist on hooking up. Homophobia is more open there, and you should be VERY discreet. Bear in mind that not only is there civil unrest in the capital but also the really poor areas are close by - a well-fed, well-dressed American or European will stand out and be a target.

Please report back!

And yet the city authorities wonder why tourists (with all their spending) choose to go elsewhere

My “grace period” is 15 minutes. I feel that’s long enough to wait for someone who has my phone number and can contact me. When I was dating (both regular guys and providers), I was clear about making plans and scheduling a date…and I always messaged mid-morning to confirm that we were meeting that evening as planned. I only ever had 2 working guys not respond to my message and they were no-shows, so my ‘Plan B’ took effect.

Interesting post. I don’t know the Pacific NorthWest well, but I would have thought that your skill set would be in great demand. As a client and total top, I’ve always valued highly a devoted cocksucker and cum-eater. When I was single and between boyfriends, I’d run an explicit profile online and I had plenty of providers contact me. I wonder if that approach would work better for you too. Advertise online and state you’re open to one-off meetings with (your preferred characteristics of) a total top. I suspect you’d find plenty of horny guys, both amateurs and providers.

If this referred to Latin America & Spain and possibly Italy, I’d completely agree. I’m less sure about other European countries: I don’t go to bars but I’ve been clubbing in France, Denmark & Sweden. I was treated well but I was always with a younger partner so I’m not sure how an older singleton might be treated. Culture aside, I wonder if economic circumstance plays a major part. I found that younger Italian and Spanish men often were interested in an older man. Some guys were discreet in public and trading sex in private. Some men appreciate an older, more mature man. Some undoubtedly seek a sugar daddy. Certainly, when I spent a long time in Buenos Aires in 2007-2014, I was startled at first by how often younger men came onto me. It seemed that a well-groomed, smartly- dressed older man in Argentina is prized by attractive young men who are not sex workers as such but looking for support and offering companionship.

I take issue with the thread title. I don’t accept that there is a “major aversion” here. We all have our individual preferences and make individual choices. In the same way, I bet most posters here have a range of friendships. I have 3 friends with whom I go to classical music recitals; I have only 1 other friend who likes opera; I’ve several friends who enjoy going out for dinner; but I’ve only 3 different friends with whom I go on vacation trips. Alas, only 1 of my friends is older than me. But I’m very glad to have 4 friends in their 30s while most friends are middle-aged.

I do this all the time. I send newspaper cuttings or photos of interesting articles and exhibitions etc.…but ONLY TO FRIENDS.

May I ask what aspect that is? And why do you find it troublesome?

Intriguing topic. Some 15 years ago, I had a long drive in a taxi from the airport in Melbourne, Australia. The middle-aged Australian driver chatted to me about how he lived mainly in Vietnam but ‘commuted’ to Melbourne for work. He said he returned every 4 months to work for 2 months or so. He added that he made enough money in his time in Australia to live very well in Vietnam.

Stop overthinking the Preparations. Relax. Just get ready in good time to greet him. And Enjoy the experience. To make him comfortable, all you have to do is have clean linen on the bed and clean towels for him to use. Definitely do not put this in writing anywhere. And if you are concerned about the condoms, get some latex-free as well as the ones you prefer - sending a message to a masseur about this seems tacky to me. I say Do Not. What happens if the dog gets bored or misbehaves in your place? Or if the dog needs to go outside during the session?