tanman4u

@tanman4u   good to see you 'round these parts again........

This is the core of the problem. In most of the US, making an appointment with a new guy is risky for both parties. 
If I say what I want, I'm committing a crime. If he says what he'll do, he's committing a crime. If he says what it costs, he's committing a crime. Then there's the service itself...
If he does what I hired him to do, he's committing a crime.  If I pay for his work, we're both committing a crime.  And afterward, if I disclose the details, I could endanger his business and his freedom. 

“I don’t have a recent photo, but can send you a link to a courtroom artist’s sketch, if that will help”
🤣

I have quite a bit of travel coming up and traveling is my only time to hookup with guys.  I'll probably have time for two separate multiple hour meetings on this trip.  Typically with any Q&A with an escort I'm considering, he'll say something like "what are you into"?  
Here's my question, would it be wrong for me to answer with "whatever turns you on the most"?  Since I rarely get to spend time with a nuclear hot guy damn near anything will be pretty amazing for me.  The escort obviously spends WAAAAY more time with guys so I'd be more about whatever makes him happier or hornier or whatever.  I don't mean does he prefer to top or bottom as I'm always going to choose a top.  This would be more like wild versus mild?  Role play?  More oral than anal?
What do y'all think?

When I joined I was pretty obsessed with being tan. Glad I grew out of that........oh wait!

One thing I can assure you is that sex in your 50s can be great but it is likely to be different than sex in your sixties.  In my fifties I was still able to orgasm 3 times in a 2 hour session and usually 5 times in an overnight providing the provider was willing to keep going.   While I now am able to enjoy a full two hour session, it is usually a one shot deal for me.  Knowing that ahead of time, I can take my time and fully enjoy the non-orgasmic aspects of sex rather than rushing to get orgasm number 2 and number three done before my guest is ready to leave.  I have grown to appreciate watching and controlling my partner orgasm for a second or even a third time during our session.  I encourage him to come rather than having him holding out to please me and while watching my partner orgasm is not as physically satisfying as having an orgasm myself, it is usually emotionally more satisfying. It plays into my sense of power and control.  Knowing that I am able to get my sexual partner aroused a second time, feeling his erection grow and then watching as his muscles tense and then watching him convulse in pleasure a second or third time has made my one orgasm as memorable as most sessions when I came two or three times. And in the end, once my partner has come two or three times, I have the ultimate pleasure of having a younger man lying tired and sexually spent while I come to completion over his sweaty prone body.
With overnights, which I tend to have less often these days, the nighttime session is usually a prolonged session with multiple orgasms for him and a final orgasm for me.  The morning session is all about getting me off a second time, which was once an easy task, but which now requires my partner to work diligently to get the job done.
Fair warning here, you need to find a partner that is willing to make the commitment to have multiple orgasms and who is able to change the focus from getting you off to one in which he allows himself to be the focus of the quest for orgasm and who still has energy enough to insure your orgasm at the end.   Having a regular partner who knows this is the goal makes it easier.  Finding such a regular does take effort as many escorts are not so interested in allowing you to enjoy their orgasm as they are in getting the client off.  
As a result, I usually hire mid week during the early afternoon and I am able to send my partner off to the rest of their day, while I am able to lie in the warm sweaty sheets inhaling the thick musky scents of the remnants of my sexual encounter.  

And from what I just heard on a podcast of a morning radio show in LA that I listen to, everything's already sold out.

I agree with everything that has been said here. In my own experience it wasn’t something I took to automatically, and with fervor. Rather, it was more of an evolution - both physically and mentally.
 
When I first started playing with guys, I swore up and down that I would *never* bottom. Not because I wasn’t curious (that was my secret), but I think because I was all caught up in the whole tops are the “guys”, and bottoms are the “girls” BS. Stupid I know. But to me at that time -the big, hairy, rugby jock- it made sense. In reality it just gave me an excuse to not dip my toe in those bottoming waters regardless of how much I wanted to. The first time I did give in, and give it up, it was to another jock (hockey) which I think helped me to think it was ok. But, what freaked me out was I liked it - I mean *really* liked it. So much so, I didn’t go back down that path again until I was in my late 20’s when a FWB flipped the script on me, and there I was in bliss again. After that, it became a “secret”- I dated guys as a top, but hooked up or engaged gents as a bottom. I was about 32 when I finally gave up the ghost, and just accepted my preferred role. Have I topped since? Absolutely - but those times have been organic, in the moment times - nothing was ever planned.
 
As others have said, much MUCH of you enjoying being a bottom has to do with the skill of your top. If your top doesn’t know how to captain his ship, it probably won’t be enjoyable. Skill, size, patience all come into play literally when you’re a bottom. There is also a mental aspect - getting over whatever preconceived notions you may in your head about what it may mean to be a bottom. Some of that can be countered by playing back there on your own - fingers, toys, massagers. But to really get past those mental notions, you will need the real thing.
 
Who knows? Maybe you’ll try it, (I’d recommend a few times), and realise bottoming really isn’t for you - the fantasy is better than the reality. That’s great too. I know a few friends who have tried the bottom role, but don’t enjoy it at all. Same way, I have other friends that don’t get any pleasure from topping. There’s a lid for every pot, and all that.
 
When you do decide to bottom, just remember three golden rules:
1. Cleanliness is next to godliness
2. Slow and steady wins the race
3. Lube (and more lube) is your best friend
 
Good luck to you, @nycboi! Let us know how it goes, and if a provider, who you’re considering ?

I think a lot of hirers are probably like me and only hire while traveling, and travel is WAAAY down this year (and of course last year). I f*cking love to travel but it’s all biz related and that’s just now starting to move again. My normal 12-14 stateside trips in a normal year dropped to 3 last year and hopefully may hit 5 this year (fingers crossed).

Numero dos por favor.