Escort keeps asking me to bottom (I'm a top)

[SteelFan]

On the flip side, have any of you ever hired an escort who claimed to be strictly top and then convinced him to bottom for you?

[big-n-tall]

On the flip side, have any of you ever hired an escort who claimed to be strictly top and then convinced him to bottom for you?

 

Well... sort of...

A guy I see (sadly, not very often) never claimed to be strictly top. However, because of his build and penis size most people assume he is a strict top. One day I just randomly asked did he bottom. He told me he did, but not very often. He said it was more than a few years ago since he did. What got me super excited was that he was immediately game for me to top him... no hesitation. The one condition was we had to work him up to it with a lot of butt play. Let's just say the entire experience was awesome. Lotsa kissing, body contact, sexy talk (with a heavy dose of encouragement), all while playing with his ass.

 

Needless to say, we both had a really good time. He texted me many times for days after about the experience, how much he enjoyed it, and when I was coming back to his area.

 

It's moments like that that gives you a huge, and I mean huge, boost of confidence.

[Rudynate]

On the flip side, have any of you ever hired an escort who claimed to be strictly top and then convinced him to bottom for you?

 

He volunteered. I had hired him to top me. And he asked me if I was a top. And I said, "Yes, usually." So he asked me if I would like to flip, which I really love doing. So it worked out

[Juan Vancouver]

Wolfer,

 

I realize that I am getting late to the party, but since I am going to write something that nobody has written yet, I thought, what the heck.

 

I have two things to say to you:

 

Chill. You are waaaaaayyyy overthinking this whole thing.

 

and

 

Chill. This is not your boyfriend. This is not a lover or a fuck buddy.

 

This is not someone with whom you have to go through complex negotiations trying to read between the lines, wondering whether he really wants this or not, whether he likes you or not, whether he is unfulfilled with you or has a secret agenda. There is absolutely no guess work here.

 

He is just doing his job. Not smoothly, I agree, but he's just trying to make you happy. Granted, it would be nicer if he remembered that you already said no, but he is not trying to force you, corner you or convince you to bottom for him. Its not that he secretly needs to fuck some ass and is trying to use your time. Believe me, if he wants to fuck ass he will find someone who wants it.

 

All he is doing, which becomes almost a reflex when one works as an escort for a long time, is making sure he is offering a varied, fulfilling experience. Also, since most of his work is as a top, he might equate fucking with being a good escort. He just wants to be good with you as well. Some gay men feel a little shame when being fucked, because they assume it's the getting fucked that is fun, so their partners are missing out. Again, he just wants you to be on the right side of pleasure.

 

And... even if he was trying to convince you to get fucked... who gives a rat's ass? Why does this matter? All you say is "No, I prefer to fuck you." Period. If he is ready for that and agrees, then that's wonderful. Reading your post it seems as if he is perfectly happy with that, so I really don't see why there would need to be a complication.

 

One of the biggest mistakes that I see people doing when entering a professional relationship like this is wanting to apply the same rules and dynamics that are relevant in romantic relationships. The whole point of being with an escort is that you don't have to guess whether he is withdrawn, or angry at you, whether he is in the mood or not, whether he really likes you or not.

 

This is comparable to going to the psychologist and ask: "Why are you so quiet? You never tell me anything about you! Do you like me?"

 

Not relevant.

 

Be polite. Communicate clearly. Honour your agreements. Show up in time, prepared and clean. Pay the agreed fee. Forget entirely about the whole thing until you feel like booking again. If you do this, he will think you are the best.

 

He will try to do the same in return, always making sure that he keeps remind you about his broad skills portfolio in case one day you feel ready for something else. He doesn't mean anything.

 

Take it easy. He is an escort. Enjoy the good, forget everything when you are done. Not worth it to waste your time trying to decode his secret plan. He has none.

 

It's supposed to be fun. It IS fun. Don't complicate it.

[TruthBTold]

Juan, the above is why I love you.

[rocksinurhead]

escorts sometimes tell me i have a nice ass and ask me if i ever bottom. i just take it as a compliment and politely decline.

[mattr]

Wolfer,

 

I realize that I am getting late to the party, but since I am going to write something that nobody has written yet, I thought, what the heck.

 

I have two things to say to you:

 

Chill. You are waaaaaayyyy overthinking this whole thing.

 

and

 

Chill. This is not your boyfriend. This is not a lover or a fuck buddy.

 

This is not someone with whom you have to go through complex negotiations trying to read between the lines, wondering whether he really wants this or not, whether he likes you or not, whether he is unfulfilled with you or has a secret agenda. There is absolutely no guess work here.

 

He is just doing his job. Not smoothly, I agree, but he's just trying to make you happy. Granted, it would be nicer if he remembered that you already said no, but he is not trying to force you, corner you or convince you to bottom for him. Its not that he secretly needs to fuck some ass and is trying to use your time. Believe me, if he wants to fuck ass he will find someone who wants it.

 

All he is doing, which becomes almost a reflex when one works as an escort for a long time, is making sure he is offering a varied, fulfilling experience. Also, since most of his work is as a top, he might equate fucking with being a good escort. He just wants to be good with you as well. Some gay men feel a little shame when being fucked, because they assume it's the getting fucked that is fun, so their partners are missing out. Again, he just wants you to be on the right side of pleasure.

 

And... even if he was trying to convince you to get fucked... who gives a rat's ass? Why does this matter? All you say is "No, I prefer to fuck you." Period. If he is ready for that and agrees, then that's wonderful. Reading your post it seems as if he is perfectly happy with that, so I really don't see why there would need to be a complication.

 

One of the biggest mistakes that I see people doing when entering a professional relationship like this is wanting to apply the same rules and dynamics that are relevant in romantic relationships. The whole point of being with an escort is that you don't have to guess whether he is withdrawn, or angry at you, whether he is in the mood or not, whether he really likes you or not.

 

This is comparable to going to the psychologist and ask: "Why are you so quiet? You never tell me anything about you! Do you like me?"

 

Not relevant.

 

Be polite. Communicate clearly. Honour your agreements. Show up in time, prepared and clean. Pay the agreed fee. Forget entirely about the whole thing until you feel like booking again. If you do this, he will think you are the best.

 

He will try to do the same in return, always making sure that he keeps remind you about his broad skills portfolio in case one day you feel ready for something else. He doesn't mean anything.

 

Take it easy. He is an escort. Enjoy the good, forget everything when you are done. Not worth it to waste your time trying to decode his secret plan. He has none.

 

It's supposed to be fun. It IS fun. Don't complicate it.

 

When are you coming to NY??

[Juan Vancouver]

When are you coming to NY??

 

I am there every now and then, but since I am being flown there to see a specific client I don't post an ad or see other people.

 

I love it there.

[+ VeryHappyCustomer]

On the flip side, have any of you ever hired an escort who claimed to be strictly top and then convinced him to bottom for you?

Yes. This happened with my most recent hire. His ad said versatile, but when we started he said "I don't get fucked. I'll fuck you... all the guys want it but they can't always take it 'cause I'm such a big guy... blah blah blah". It sounded like a porno script. I repeated his lines back to him and he perked up fast. Then I did what I'd intended to do all along.

 

Maybe it was a play within a play.