spidir

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It’s definitely part of my massage repertoire should the client want it. Of course I check the area (discreetly) beforehand and ask the client to shower first. 
I do think that the giver should really enjoy doing it for it to feel good. It’s fortunate that I love rimming, I love the reaction it gets and the eroticism of it. I’ll leave it to clients to decide whether or not my rimming is any good! They’re best placed to provide a critique. 
 

I LOVE rimming. It’s among my best sexual talents, and one of my specialties. I enjoy doing this for my clients, and sometimes they book me just for a rimming session. It’s not infrequent I make men cum this way. Great if a client enjoys rimming me too, but I’m truly a giver. I wrote a guide. Linking below:
 

You asked about legal problems.  Apart from a couple of stories I've read about online (i.e., no personal knowledge), I think that risk is very low. 
What seems to be a larger risk is extortion or, at least, attempts at extortion.  If you have a lot to lose if your hiring habit becomes known to others, then someone attempting to extort you puts you at risk.  That's why you'll see some here advocating the use of a burner phone and never meeting anyone where they live.  I didn't take either of those precautions and never had anyone try to extort me, but I did almost hire someone whom I subsequently read about here who did threaten to expose clients to their families.  I felt like I dodged a bullet there even though I don't think that being exposed to colleagues or family would have caused any problems for me other than whatever gossip people might have engaged in following the disclosure.

As long as you have your head on your shoulders, there's not a ton of risk in my opinion. Nothing revolving this is 100% guaranteed, but tons of people here have been hiring for decades. Overall, just stick to well reviewed guys and you should be okay. Avoid new guys without reviews, because those are going to be the kind of guys who you'd be likely to get more trouble from. That's not to say that new guys should be avoided at all costs, but if you're risk averse then that makes the most sense.
Sometimes men will think with their penis instead of their brains, and that's where you sometimes land yourself into trouble.

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I have a regular good friend of 4+ years, I’m 68 he’s 23. Not a problem. He’s a bit unique (mature) for his age…he’s definitely attracted to older/mature. It does happen!

I have never been attracted to guys my own age, always to younger. When I hire, my bracket is 18-25, 30 at the very most. Of course, I don’t card the guys, they can be older as long as they look the age I am looking for. In non-commercial hook-ups, I am more flexible, but usually not less than 10-15 years younger.
Full disclosure:  my current unpaid regular just turned 24, which means a 40-something year gap with yours truly. He is into daddies, and he is always horny as hell, pure dynamite in bed. We have great fun together.