Just Chuck

If I am organizing an outcall I don't mind- I consider covering the uber the outcall fee. 
I think also its to ensure you are serious and the provider won't be left sitting in a hotel lobby after paying for their own uber. 
 
 
 

I’ve had more than one provider say they look at the Uber as a form of “deposit”, i.e. if you arrange and setup the Uber it’s makes the client appear more serious/reliable. I’ve done that on occasion.
There is no reason why it should come up late in the conversation though. 

They can get the shape right. But I've never seen one with the right combination of soft and stiff.   

They can get the shape right. But I've never seen one with the right combination of soft and stiff.   

They can get the shape right. But I've never seen one with the right combination of soft and stiff.   

Yes, yes, yes.
You have to WANT the other man inside of you.
Desperately WANT. 

Definitely not an expert in bottoming, but(t) being in the business of learning, I can recommend the book "The Ultimate Guide to Anal Sex for Men". Right away, I can tell that if you don't bottom then try an oversized dildo, there might be an issue there.
As for "the right one", yes, I think that's a real thing. The times I've bottomed has been because the right person has led me to it, not because I deliverately want to.
Not an expert in bottoming, but an expert in learning, and as such, I'd say look for good, reliable information resources on the topic, that is in addition to info from people who are experienced.

I found it impossible to enjoy bottoming until my early 30s. Believe me I tried. I wanted to know what the big deal was.
 
Bodies change, yours can too. If you are able to enjoy it in a self-love session, you can learn to enjoy it with a guy. My suggestion, get a smallish plug. Leave it in for an extended period (an hour or so). Do this on a regular basis. Eventually you learn to get much more comfortable with the sensation, so it helps to relax oneself, both physically and mentally, so that a cock is possible. 
 
And poppers. Lots of poppers. 

I have only engaged in anal at all a handful of times, and bottomed all of those times except once… being a little guy means that the vast majority of suitors want to top me.  Bottoming was painful every time I tried it, despite being very turned on by it.  Part of the reason I’m interested in providers is to do a few “test runs” of topping before I have to worry about the bottom enjoying it.  I chickened out on my one and only session with a provider (last week) but will try to go for it next time.

He looked just like the photos when I met him this fall, except he was taller than I expected.

I think she’s great. I love gender-bending people. 

He no-call-no-showed for an appointment with me in DFW too. Later that evening, he texted an excuse that his ex-boyfriend was seen in town with a key to his apartment and he had to rush home.

JDHATX:
https://rentmasseur.com/JDHATX
For me hands down one of the most memorable massages I’ve experienced thus far. You can PM if you’re interested in the details.

I think she’s great. I love gender-bending people. 

He no-call-no-showed for an appointment with me in DFW too. Later that evening, he texted an excuse that his ex-boyfriend was seen in town with a key to his apartment and he had to rush home.

He no-call-no-showed for an appointment with me in DFW too. Later that evening, he texted an excuse that his ex-boyfriend was seen in town with a key to his apartment and he had to rush home.

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