High school friend is an escort

[John Doe II]

You are lucky. Just go for it. Don't overanalyse. Message him on insta/fb and see what happens. Be polite but direct. This is my advice.

Message him what though? About his ad? Wouldn't that be

One more thing: Make sure he is hot as you remember him. That he did not gone bald, or put on weight etc. ?

He is hotter now than from what I remember in my hs days haha

What would I message him though? About his ad? Isn't that too direct?

[The_Impeccable_G]

Message him what though? About his ad? Wouldn't that be

 

He is hotter now than from what I remember in my hs days haha

What would I message him though? About his ad? Isn't that too direct?

Start a casual chat catching up with an old friend and drive the conversation to what you want. Tell him he is better looking than hs, ask him how is work, money etc. I would bring up the ad as a last resort.

[The_Impeccable_G]

Start a casual chat catching up with an old friend and drive the conversation to what you want. Tell him he is better looking than hs, ask him how is work, money etc. I would bring up the ad as a last resort.

Ask him if he has done any modelling... This always works for the guys I want to pick up ?

[+ honcho]

We actually met another time in public at an event organized by a mutual friend and I let him be introduced to me as if I never met him.

 

Surprisingly, this was the subject of a Miss Manners column a long time ago - not so much about escorting, but how should gay men react when having met previously and anonymously in sordid circumstance - and Her suggestion was, in response to

"Joe, this is George, George, Joe" .. to smile and say "I don't believe we've been introduced ....".

 

I actually got to use that line, playing oboe trios with a friend and a friend of his who I had spotted on cam4 a few years previously ...

[Luv2play]

I agree. If there‘s not an active ad, let the fantasy fade.

 

At a very high brow benefit in NYC, I once ran into an escort I had hired.

He was the trainer of one of the mega corporate wife’s at the event.

As soon as he saw me, I saw the panic in his eyes that he might reveal

our secret and that he didn’t know how to greet me. When we were

formally introduced, I threw my arms open wide, screamed his real

name (which I didn’t know until that exact moment) and greeted him

like we were long lost best friends from the gym. I could feel his sigh

of relief as we hugged.

 

Crisis averted. He later sent me a text thanking me, and we’ve met

several times since. The lesson? It’s only awkward, if you make it

awkward.

You handled that situation very well. I probably would have pretended I had never met him before. Learning his real name on the spot might have thrown me as well. In any event I would have done nothing to embarrass him as I highly value discretion on both sides of the client/escort relationship.

[tj_forplay]

So I noticed an ad a while back of a friend who i recognized from high school is now an escort. I'd love to meet him but his ad is gone now. We are friends on FB and i follow him on insta. Any recomnendations?

I wouldn't go down that road. Just let it be. I was in a similar situation, my high school friend wasn't a escort but was "discreetly" on Grindr and posting on Craigslists how he was cum dump & wanted to be used. We were really good friends through middle school & high school but drifted apart after graduation, but were on each other's social media. I hadn't seen him in years before I came across his postings. I never thought he was into guys at all. It's kind of a long story but there's no fairy tale ending ?

[John Doe II]

I wouldn't go down that road. Just let it be. I was in a similar situation, my high school friend wasn't a escort but was "discreetly" on Grindr and posting on Craigslists how he was cum dump & wanted to be used. We were really good friends through middle school & high school but drifted apart after graduation, but were on each other's social media. I hadn't seen him in years before I came across his postings. I never thought he was into guys at all. It's kind of a long story but there's no fairy tale ending ?

I would say we where more acquaintances since we had a just few classes together. We never actually hung out. He is not discreet about his sexuallity and it doesn't seem from his FB posts that he is discreet about his "side business." He doesn't advertise in fb but there are very subtle hints about sex work via comments posts.

[nate_sf]

My suggestion would be to get in touch through Facebook and let him know you're gay. It gives a reason for getting in touch and can be a bonding experience.

 

If things go along OK, then ask him if he's on Insta (even though you already know that) or mention that you follow him there. This would give him an opportunity to share his sexier side, but would also allow him to put up a boundary if he's not wanting to go there.

 

I would not mention you'd seen the Rentmen ad. Different guys have different ways of compartmentalizing these things and it's hard to know what kind of reaction there could be, but it could be bad. Having been an escort and having done porn myself, there were a few instances where people from college told me they'd seen my videos. In one instance it was OK and we laughed about it (and then he invited me to a sex party at his house!), but with another the way he approached it was unnerving. I'd like to think I'm level-headed and knew what I was signing up for, but was surprised how I felt in the one instance.

[John Doe II]

My suggestion would be to get in touch through Facebook and let him know you're gay. It gives a reason for getting in touch and can be a bonding experience.

 

If things go along OK, then ask him if he's on Insta (even though you already know that) or mention that you follow him there. This would give him an opportunity to share his sexier side, but would also allow him to put up a boundary if he's not wanting to go there.

 

I would not mention you'd seen the Rentmen ad. Different guys have different ways of compartmentalizing these things and it's hard to know what kind of reaction there could be, but it could be bad. Having been an escort and having done porn myself, there were a few instances where people from college told me they'd seen my videos. In one instance it was OK and we laughed about it (and then he invited me to a sex party at his house!), but with another the way he approached it was unnerving. I'd like to think I'm level-headed and knew what I was signing up for, but was surprised how I felt in the one instance.

Thanks! I appreciate your advice. I really didn't have any intention to bring up his ad if I contacted him via insta/fb. At first, I thought about calling him up as soon as his ad came up again but decided against it because I didn't want to make him uncomfortable if/when he'd recognize me at the door.

[+ Coolwave35]

I have a grindr ad that I use to hire that doesn’t have any face pics. A very sexy guy that I was friendly with in high school messaged it.

 

I said I’d love to help him out, but that we were acquainted through school, and I felt bad knowing his identity while he didn’t know mine as I prefer anonymity when I hire.

 

He convinced himself that I was a teacher of his and I let him believe it.

 

He is a night attendant at a group home and invited me over at midnight after everyone was asleep. He immediately recognized me, said that the mystery of this was so hot, and that he was incredibly turned on.

 

We had a fun romp, I paid him, and before I could start my car, he had blocked me from all social media accounts and Grindr. It was still fun, and he definitely kept his sexyness, but I think he’s very scared to be outed, not that I ever would.

[John Doe II]

I have a grindr ad that I use to hire that doesn’t have any face pics. A very sexy guy that I was friendly with in high school messaged it.

 

I said I’d love to help him out, but that we were acquainted through school, and I felt bad knowing his identity while he didn’t know mine as I prefer anonymity when I hire.

 

He convinced himself that I was a teacher of his and I let him believe it.

 

He is a night attendant at a group home and invited me over at midnight after everyone was asleep. He immediately recognized me, said that the mystery of this was so hot, and that he was incredibly turned on.

 

We had a fun romp, I paid him, and before I could start my car, he had blocked me from all social media accounts and Grindr. It was still fun, and he definitely kept his sexyness, but I think he’s very scared to be outed, not that I ever would.

I take it he was not into repeat business... bummer

[stop]

I would say we where more acquaintances since we had a just few classes together. We never actually hung out. He is not discreet about his sexuallity and it doesn't seem from his FB posts that he is discreet about his "side business." He doesn't advertise in fb but there are very subtle hints about sex work via comments posts.

 

are you discreet about your sexuality? do you have any concerns about others finding out? this is a two way street he could out you if you are in the closet. for every 100 great guy escorts there is a brodie sinclair

[+ poolboy48220]

A couple I know casually had a massage ad up a couple of years ago, I hired them once. They've since split, one of them has had a Rentmen ad up for about three months, and the other just put an ad up. I'm still very locked down but I'd very much like to see the guy who just posted an ad again once it's safe.