Trip With a Masseur

[Rocca]

There is a masseur that i am totally smitten with. I would like to take him with me to Maui for a week and I want to hire him to give me a massage everyday we’re there. I adore this guy and his massage is magnifique! He doesn’t advertise as an escort but there is a great HE with the massage, so I’m not sure if he’d be open to this, and I dont want to offendj. I will be compensating him for every day that he’s with me. Has anyone ever done this?

Edited March 26, 2021 by Rocca

[Guest]

You better be very clear what you expect during these 7 days, and his boundaries.

Wouldn't want either of you stuck being unhappy, for a week, on an island...

[Guest fm0322]

Your offer is generous and he's lucky to know you. If he goes, he loses a week of income and runs the risk of travel. HI has strict entry rules and he may face costs associated with it. You don't mention if there is a financial arrangement. I agree with @Oaktown about boundaries. I suggest you move slowly and not damage what sounds like a nice arrangement.

[Jamie21]

Often with these ideas the fantasy is more appealing than the reality. It may be better to keep it in your head as a nice dream and a possibility but not do anything proactive to make it happen.

You could say to him next time you’re with him that you are thinking of a solo trip to Maui and see what his reaction is.

[MscleLovr]

Wonderful idea @Rocca. I say Go for it, provided you can afford the costly trip. A week in Maui with an obliging masseur sounds terrific. But as others have said, you must be explicit and detailed about what you are offering to him.

 

FWIW I once took a swimming coach away with me, not to Maui but to an equally lovely longhaul destination. The coach was fit, mid 20s and had a very good body. I had a real crush on him so I took him out for coffee or lunch after lessons 2x a week. After a few weeks, we were showering together after the lesson when he suggested I would enjoy using the sauna (he serviced me orally and I gave him a handjob). That became an enjoyable routine.

 

When I thought about going away for some Winter sun, I asked him out for dinner to discuss my idea. Luckily I had thought out all the details (as previously I’d hired fit young men for trips). I told him I’d pay for the flights and the hotel as well as all the meals and drinks, and I said I’d want a lesson each day before breakfast and again probably late afternoon. I emphasised we’d have breakfast together and then he’d be free for most of the day until we had the 2nd lesson and dinner together.

 

He was interested and asked questions. I was a bit surprised at his questions. He didn’t mention money. He did ask if he’d have his own room. I said No, we‘d share a room. And added that the hotel beds are king sized. He asked me if I was gay and I said I was. He then asked about sex. And I said I enjoyed getting oral to completion, and I liked seeing him come…and I was totally OK if that was all he wanted to do. (I’d met some of his friends and they all seemed very fit and str8). I did spell out that I enjoyed having sex every night.

 

He agreed there and then. But I followed up with a phone call the next day to confirm the dates etc. Again he didn’t ask about money. He did say he was a little worried that he didn’t have the right clothes for a 5* hotel. So I took him shopping which was good fun. I then raised the question of money. He asked if I was really going to pay for everything and when I confirmed that, he said I won’t need $$$ as it’s totally free.

 

Overall, we had a really great time on the trip. He was excited on the flight out and he seemed relaxed at the hotel (where they knew I was gay and obviously saw him as my young man). He did spend almost all the time with me. He worked out in the gym every day but wanted to come with me on excursions and hikes.

 

He initiated sex the first night and told me we could try more than the usual stuff. During the week, I got him to bottom 2x for me but I had the feeling he really wasn’t into it, so I told him full oral was just fine for me. During our last breakfast, I told him I’d had a good time with him. He countered that it had been his best vacation ever, and he’d had an amazing time with me. I raised the topic of money but he commented he hadn’t been able to spend any and “we had the best food” all week. I knew his income was small and erratic, so when we got back to the room to pack, I insisted on giving him $1000. He refused the $$$ but was so grateful when I insisted, that we had good sex to end the vacation on a high.

[Rocca]

Your offer is generous and he's lucky to know you. If he goes, he loses a week of income and runs the risk of travel. HI has strict entry rules and he may face costs associated with it. You don't mention if there is a financial arrangement. I agree with @Oaktown about boundaries. I suggest you move slowly and not damage what sounds like a nice arrangement.

I will be compensating him for every day that he’s there to make it worth while.

Edited March 26, 2021 by Rocca

[Rocca]

Been there done that too... My experience did not end well and would be more than willing to explain in private.

Im paying him for everyday that he’s there, he will have his own alone time too. As long as i get my massages and H/E at the end of the evening, I’ll be happy ?. Im low maintenance.

[NJ_hiker]

Im paying him for everyday that he’s there, he will have his own alone time too. As long as i get my massages and H/E at the end of the evening, I’ll be happy ?. Im low maintenance.

Go for it man. Let us know how it goes.

[Redwine56]

I will be compensating him for every day that he’s there to make it worth while.

Is this compensation in addition to travel expenses and meals? If so, I think it's a win win for both of you as long as you keep your emotions in check. Spending an entire week on a romantic Island with someone that you are "smitten with" who may not meet your expectations will be very disappointing. However, it could turn out to be a wonderful time for both of you. Let us know if he accepts your offer. If not, I'm sure you will find several Forum members willing to pack their bags in a hurry.

[Rocca]

I see it as win/win too. All expenses and meals paid in addition to a per diem fee to make it worth his while. Ill update you all if he accepts or declines the offer.

[MscleLovr]

I assume you’ve already spent some considerable social time and enjoyed meals together @Rocca ?

 

If not, I’d urge you to do so. A week together on a lovely island is not the time and place to discover that you and your companion don’t share some interests and that congenial conversation is not easy at mealtimes.

[+ Tygerscent]

You better be very clear what you expect during these 7 days, and his boundaries.

Wouldn't want either of you stuck being unhappy, for a week, on an island...

It may also be to both of your benefit to establish and self evaluate each of your experience traveling with another person involving various levels of intimacy~ Simply to agree on a travel and financial arrangement may not be enough~

~ Tyger~

[+ sniper]

This is one of those things that I think sounds great in theory but IRL I'm too much of an introvert to make it work.

[Rocca]

I assume you’ve already spent some considerable social time and enjoyed meals together @Rocca ?

 

If not, I’d urge you to do so. A week together on a lovely island is not the time and place to discover that you and your companion don’t share some interests and that congenial conversation is not easy at mealtimes.

Yes, I’ve gotten to know him socially.

[Rocca]

Just to update: i asked and he said yes????????????????????????????????????

I’ll let u guys know how it goes. I can’t wait. After how 2020 went. I really need this.

[Guest fm0322]

Just to update: i asked and he said yes????????????????????????????????????

I’ll let u guys know how it goes. I can’t wait. After how 2020 went. I really need this.

Chapter 1: Should I Do It? Chapter 2: He Said Yes. Chapter 3: ....

 

I can't wait to read it!!

[Rocca]

A couple of people have messaged me privately to ask how the trip went, so I’m updating this here. It was absolutely marvelous! We spent a week in Hawaii, had an amazing time and the masseur who accompanied me is wonderful!!!! So much so that I plan to do it with him again as soon as my schedule permits, and he said he’d love to Join me again.  I’m so glad I did it!!!

Edited November 17, 2021 by Rocca

[Redwine56]

On 11/17/2021 at 7:02 AM, Rocca said:

A couple of people have messaged me privately to ask how the trip went, so I’m updating this here. It was absolutely marvelous! We spent a week in Hawaii, had an amazing time and the masseur who accompanied me is wonderful!!!! So much so that I plan to do it with him again as soon as my schedule permits, and he said he’d love to Join me again.  I’m so glad I did it!!!

A perfect example of .  .  . Nothing ventured, nothing gained.  I'm so glad it worked out for both of you.  Sometimes, you have to go with the gut.  It appeared as if you gave it enough thought before making your decision.  

 

 

[DapperGent]

On 3/26/2021 at 12:54 AM, Rocca said:

There is a masseur that i am totally smitten with. I would like to take him with me to Maui for a week and I want to hire him to give me a massage everyday we’re there. I adore this guy and his massage is magnifique! He doesn’t advertise as an escort but there is a great HE with the massage, so I’m not sure if he’d be open to this, and I dont want to offendj. I will be compensating him for every day that he’s with me. Has anyone ever done this?

I think you got to define, in the heart of hearts, if you have fallen in love with him and you secretly hope he falls for you during this trip. If your motivation is purely hedonistic, I would not only define rates and expectations but also be reasonable and give him a day off from massage and from you, remember, you’re a just a client.

Edited March 1, 2022 by DapperGent

[Terpmaniac]

Seven days on a trip with someone I barely know? No. A thousand times no. Glad it worked for you though but no way could I do this either way. As the client or the masseur.  Nope.

[Redwine56]

2 hours ago, Terpmaniac said:

Seven days on a trip with someone I barely know? No. A thousand times no. Glad it worked for you though but no way could I do this either way. As the client or the masseur.  Nope.

That's because our Terp is not allowing anyone to lay claim to his beautifully rounded baby cakes.  No one!! 🤔