How to ask a regular hire if he'll do more with you

[antelope]

I have a regular hire with who i've hung out, had dinners and drinks and we stay in touch.  As far as anything sexual all i have done is watched him jerk off, felt his muscles and body and grabbed his cock.  I definitely would like to do more with him but i'm not sure how to go about it without changing how things are between us.  What's the best way to go about this without things getting weird and awkward between us and to allow me to keep seeing him?  I met him while he was working at a strip club.

[Luv2play]

The thing to keep in mind is that strippers are not escorts, unless they advertise that fact. In my extensive experience with strippers a couple of decades ago when Montreal had the best stripper clubs in North America, I rarely encountered strippers who would provide the full services of escorts. 

Eventually I resorted to only hiring escorts because the value for money just wasn't there with strippers. With escorts you can be pretty sure what it is they will do or not do. Their business model is different from that of strippers.   

Edited March 27, 2023 by Luv2play

[pubic_assistance]

How to ask a regular hire if he'll do more with you

Offer money.$$$

Edited March 27, 2023 by pubic_assistance

[BuffaloKyle]

I'd just ask when you are setting up another appt! Just say something like I really enjoy our sessions together. Would you be opposed to letting me preform oral on you sometime. We can talk about it during our next appt as well if you wanna think about it. It'll probably cost more money but you've hired him multiple times so if he's comfortable enough with you to get into that he will. Let us know what happens!

[+ nycman]

[+ DrownedBoy]

Everyone here is right.

Make sure his money is in a pile. Take a Benjamin, and ask your question while holding that bill over the pile.

[+ Coolwave35]

I found strippers to be incredibly open to additional opportunities, including regulars, when the money is right. 

Hell I got 11 strippers to play Survivor at my house and agree to be filmed in full on orgies with each me and each other.  It all started with a bank withdrawal slip and the courage to ask.

Go for it!  

[+ Pensant]

Just be open about any fetishes/desires you have before the first meet. I have specific things I like and 90% of the time I have a successful meet-up. I have the ability to broach these things in a light-hearted way, so I don’t come across as creepy. I’m always amazed at how many sessions my little coterie of special friends have avoided because of what they probably perceived as a potential “creep”.

[Jaroslav]

Ask. 

The very fact that you're asking here about a change in dynamic suggests that you care more about the relationship you have with him than he does with you, which is in some ways a problem. Escorts, while they may be friendly, aren't our friends as long as they're taking our money. If you offer more money for what you want above and beyond what you've been doing with him, and he doesn't accept, then that's just the way it is. He's more than likely not going to think differently of you because your'e a client and he has other clients.

Be careful of thinking the escort feels any kind of loyalty to you because of a historic past good relationship. Your loyalty and concern for him is probably, likely greater than his is to yours. That isn't to say that escorts are bad people or aren't friendly. They're just in this for the work component of it – otherwise they wouldn't be looking to get paid. As long as money is transacted every single time you get together, it's not a business relationship, not a friendship no matter how friendly you may be. I'm friendly with the dentist, but he's not going to check out my mouth for free.

[+ Pensant]

18 hours ago, Jaroslav said:

Escorts, while they may be friendly, aren't our friends as long as they're taking our money.

That’s the case 99% of the time but I’ve had a few exceptions, including currently.

[Jamie21]

Just ask and open your wallet. If you’re concerned that he might say ‘no’ and that might influence the relationship…don’t be. It’s very unlikely that he views the relationship in the same way you do (despite how he may behave in the session- that’s just because he’s good at his job). 

[Alex93108]

Agree on all the above. In some cases the provider might actually like you enough to throw in off the clock hours and others favors from my personal experience.  I found the whole concept off of the clock confusing, i posted here to ask the group if I was handling it fairly  In the end I think I handled it well, thanks to the collective wisdom of the group. 

Just ask - but I realize for some, asking is awkward, so I empathize with the dilemma.  In the end do what you feel comfortable, but lean in on the collective wisdom of those that replied. 

[italianboyph]

Just be honest and upfront about your desires that you wanna do with him, nothing wrong with that.