Travel companionship with more intimate services

[+ SundayZip]

The I fucked up, help fixt it, thread created by @Coolwave35, fascinates me.  Back in the day, long before I retired, I day-dreamed that one day I might have enough money to entice a sexy young man to travel with me. We'd see far-off, exotic places together and have wonderful sex after a full day of marvelous activities (a lot like the vacation that @coolwave35 describes). It was just dream for me back then. Now that I'm retired, I'm somewhat surprised that I have the financial resources to do exactly that (a combination of good luck and good investing). What I've also discovered is that I prefer traveling with people closer to my own age with similar likes, dislikes and life experience; people who I know, with certainty, will enjoy my company regardless of who picks up the tab. Not that I don't enjoy occasional time spent with sexy young men who are compensated for their intimate companionship. But the terms of those dates should be well defined with me having no expectation that they'd choose to hang out with me 'off the clock.'

Maybe my change of heart is due to a lack of self-confidence. Maybe if I had more self-confidence, I'd assume that attractive young men, half my age, would choose to travel with me with no strings attached. Or maybe, I wouldn't care as long as they were convincing actors. But I think my own insecurities would get in the way.  

How do others feel about mixing extended, immersive travel companionship with more 'intimate services?' 

[+ ApexNomad]

2 hours ago, SundayZip said:

The I fucked up, help fixt it, thread created by @Coolwave35, fascinates me.  Back in the day, long before I retired, I day-dreamed that one day I might have enough money to entice a sexy young man to travel with me. We'd see far-off, exotic places together and have wonderful sex after a full day of marvelous activities (a lot like the vacation that @coolwave35 describes). It was just dream for me back then. Now that I'm retired, I'm somewhat surprised that I have the financial resources to do exactly that (a combination of good luck and good investing). What I've also discovered is that I prefer traveling with people closer to my own age with similar likes, dislikes and life experience; people who I know, with certainty, will enjoy my company regardless of who picks up the tab. Not that I don't enjoy occasional time spent with sexy young men who are compensated for their intimate companionship. But the terms of those dates should be well defined with me having no expectation that they'd choose to hang out with me 'off the clock.'

Maybe my change of heart is due to a lack of self-confidence. Maybe if I had more self-confidence, I'd assume that attractive young men, half my age, would choose to travel with me with no strings attached. Or maybe, I wouldn't care as long as they were convincing actors. But I think my own insecurities would get in the way.  

How do others feel about mixing extended, immersive travel companionship with more 'intimate services?' 

I wouldn’t call it a lack of self-confidence so much as a deep understanding of what truly makes you happy and fulfilled. There’s nothing wrong with valuing shared experiences with people who genuinely enjoy your company, and I think that clarity is something to celebrate.

Whenever there’s a transactional component, it’s important to understand that providers are there because you’re paying them to be there. That doesn’t mean the connection can’t feel enjoyable or even meaningful in the moment, but the terms need to be clear.

When it comes to mixing immersive travel with this dynamic, I think it becomes even more important to have those boundaries defined. Extended time together can blur lines, and while some people might enjoy that fantasy, it’s essential to keep expectations realistic to avoid disappointment. Great providers, however, will often sense any insecurities and make you feel like the king that you are. But again, it’s important to remember that this is a professional relationship.

Wishing you all the happiness and confidence to keep exploring what works for you!

[+ BenjaminNicholas]

This is my bread & butter.

If you can get over any existing hangups, there's nothing better than traveling with a co-pilot who can easily handle himself, share new cultural experiences together and has the travel intellect to make sure things go smoothly at all times. 

The sex comes naturally: Frankly, it's the easy part.

Finding someone to spend a week with (or more) is a little more difficult. You have to find a personality that can anticipate things, can be comfortable in a variety of situations and can make it all flow and feel perfectly natural. 

My suggestion is you explore this a bit. 

Regret is useless. 

[+ nycman]

I know myself well enough to know a long term hire isn’t for me. I’m not saying i haven’t had wild fantasies about being feed grapes on a remote Balinese island by a stunning escort for days on end. But I’m also old and wise enough to know that being stuck on a remote Balinese island for days on end with the wrong person is Hell on earth. Grapes or no fucking grapes.

If I did manage to find an escort that I honestly felt we clicked well enough to even attempt such an escapade, I’d be too frightened of actually falling for him to relax and have a good time. So it’s a "no" for me. 

I love hearing about @Coolwave35’s adventures and I greatly admire @BenjaminNicholas. We’re all built differently.

I think you need to worry about whether this is a good set up for you. Looking behind the curtain and trying to guess if the escort "likes’ you or "wants to be there with you" is a fools game. And that’s true regardless if we’re talking about a one hour love affair or a ten year "relationship". 

[TorontoDrew]

I think if I was going to hire for a travel companion it would have to be someone like @BenjaminNicholas.  Someone a bit older, more worldly and still has an amazing body.

I would want a provider who likes going to museums and art galleries and not clubs.  I also want one with a great body that I can worship before getting wounded into the mattress.  This is likely a niche market.

[+ Jamie21]

I think there’s a sweet spot in the ideal travel / sex companion that’s difficult to find. It needs to be someone with similar interests but not too similar. Some overlap but also some differences. If it’s someone who shares your worldview and experience then there’s no intellectual stimulation but if it’s someone from a completely different perspective and background then you have no place to start with shared perspectives. 

 

[Thelatin]

I have a young couple (in their 20’s) that I travel with for a week at a time.  It’s a lot of time in the pool, hot tub, drinks, a few clubs etc.  They both like me and we all chat weekly.  But I understand that they like me as an older friend and customer, nothing further.  I enjoy the relationship.

[+ SundayZip]

On 1/12/2025 at 4:03 PM, BenjaminNicholas said:

This is my bread & butter.

If you can get over any existing hangups, there's nothing better than traveling with a co-pilot who can easily handle himself, share new cultural experiences together and has the travel intellect to make sure things go smoothly at all times. 

The sex comes naturally: Frankly, it's the easy part.

Finding someone to spend a week with (or more) is a little more difficult. You have to find a personality that can anticipate things, can be comfortable in a variety of situations and can make it all flow and feel perfectly natural. 

My suggestion is you explore this a bit. 

Regret is useless. 

Quite honestly, BenjaminNicholas, if I were to hire a travel companion, I think it would be you. You're no longer 21 (I believe 🙂) which I view as positive. I also believe you're worldly enough to be wonderful company and have the "travel intellect" to ease the stressful parts of traveling. Please do not tempt the susceptible! 

[+ ApexNomad]

50 minutes ago, SundayZip said:

Quite honestly, BenjaminNicholas, if I were to hire a travel companion, I think it would be you. You're no longer 21 (I believe 🙂) which I view as positive. I also believe you're worldly enough to be wonderful company and have the "travel intellect" to ease the stressful parts of traveling. Please do not tempt the susceptible! 

I’d have to agree with you—if I were to jet off around the world, BenjaminNicholas seems like the perfect pick. He sounds like someone who really gets shit done, and honestly, I absolutely appreciate that in a person. Plus, the emphasis on being a co-pilot? That’s gold. It’s all about shared experiences and making the journey just as special as the destination. That’s how you travel right.

And I don’t know how to say this without it sounding indulgent, but there are times when I really value a man who can take care of me or take charge. Don’t get me wrong—I’ve taken care of myself and my loved ones my whole life. But there are moments when I don’t want to explain or talk. When I can just trust them—with me, my body, everything—and know they’ll handle it. There’s something deeply meaningful about letting someone plan the day, seeing the world through their vision, and knowing they’ll get it right. That kind of trust makes traveling feel effortless and unforgettable.

[Km411]

Well said and whole-heartedly agree. And traveling with @BenjaminNicholas is at the top of my bucket list!

[+ BenjaminNicholas]

3 hours ago, SundayZip said:

You're no longer 21

With duct tape and some Vaseline, I can still play late 20s.

 

[+ ApexNomad]

7 minutes ago, BenjaminNicholas said:

With duct tape and some Vaseline, I can still play late 20s.

 

[mattr]

I'm intrigued by this idea.   I'm retired now and find myself in a pretty good financial position and am wondering what something like this might cost. Obviously it would vary by destination but is $20k a reasonable guesstimate?

[Guest]

50 minutes ago, mattr said:

I'm intrigued by this idea.   I'm retired now and find myself in a pretty good financial position and am wondering what something like this might cost. Obviously it would vary by destination but is $20k a reasonable guesstimate?

I’m doing Egypt with a seeking boy for 12 days. I told him he has a $30k budget and as long as I sleep comfortably, meaning no hostels or hotels without AC, he can keep what we don’t spend. My suspicion is that we’ll spend all of it cuz he likes to do stuff. 

Edited January 15 by Coolwave35

[+ robear]

19 hours ago, Coolwave35 said:

I’m doing Egypt with a seeking boy for 12 days.

Enjoy your trip!! Please report back on the whole experience.

[+ Vegas_Millennial]

4 hours ago, robear said:

On 1/15/2025 at 9:27 AM, Coolwave35 said:

I’m doing Egypt with a seeking boy for 12 days.

Enjoy your trip!! Please report back on the whole experience.

And, please report back on the HOLE experience 😉 😈

Edited January 16 by Vegas_Millennial

[+ Just Sayin]

I've traveled with the same young man multiple times over the past four years; I've enjoyed it, and he has told me he's had wonderful times, but by nature of my own personality, I want to make certain we do what he would like to do so that he has a great time.  By contrast, when I travel alone, it's all about me--what to do, when and where to eat, would I like to get a massage, etc.; plus I do not have to share a bathroom with anyone!  For me at this stage of life, I sort of like having it be all about me sometimes; I am thinking the best path is to do both--travel with him from time to time, but also plan those solo trips.