I will have a longer date when in Miami for business. Coming from a cold country I want to enjoy the the sun after a long winter. So I dont want to spend all the time in my hotel room and thinking about having a nice day with a provider like welcome drink at the pool bar-  sex - pool time, some cuddling in the poo l -sex-dinner - sex - and goodbye.  

the lady you are interested in if she would like to join you for a pool date/private time.
I have done a few pool dates with gents who were in their 50s one of the dates was at a topless pool.
We got a couple of looks maybe more than a few but I wasn't paying attention and especially in a cabana there is quite a bit of privacy
I had no issue with the age difference I know every lady is different.
Who cares if you get looks?
There is always going to be some people who will look when they see a younger woman and older guy.
Enjoy yourself it is all about the time you two are spending together

Would be that any public pool time or other public time was discreet and with him NOT all over me. Especially if there is a big age difference or attractiveness difference. Nothing screams hooker and john more than those two things.

My wife can be really clueless. This guy comes down to the beach. Pasty white skin and had to be at least 375 pounds. he was short of breath from just walking. He lays down on his towel and about 5 minutes later  this really hot 20 YO with one of the smallest bikinis lays her towel down next to his and commences to slather him with badly needed sunscreen. My wife is stunned. She says to me "I can't believe she is with that guy". I look at her and say really? Don't you get it? She's a pro. Still had no idea. So I had to explain to her by saying pro I mean she's a hooker. she wouldn't believe me.

My first thought when I see a guy who is older and who may not be as attractive is never john and hooker, my first thought is he either has money, a great personality or both.  Second thought is good for her she has an open mind.  Of course, it also depends on the setting, in Vegas I am more likely to think hooker and John.   Anyway, at the end of the day, if people want to stare and make up their own story, who cares?  

ohhhhh... america problems.

what a great country to live in when it comes to so many things, but goodness gracious ...we are such prudes when it comes to judging others sex lives!
its a good thing you will be in miami and that place is sugar baby central.
relax & have fun.
xo

"And what makes you such an expert on the subject?"

Think before engaging the old tongue.

The better response to her would have been:

"Some people see the beauty within."

Then you would have gotten a very satisfying "harrumph"

ou might want to book 2 or 3 providers in Miami for separate one hour sessions, then pick the one you have the best chemistry with for a longer 'pool' date.  You really don't want to commit a lot of $$$ with a provider you've never met before.

I was in a relationship with an older man at the time, maybe 34.  We were out and about and I saw a business called "Cindys Stress Relief" or something like that.  Being completely naive at the time, I joked to him, "What does Cindy do to relieve stress?  Blow jobs?  Lol."  He just looked at me and smiled.

Tell her the itinerary with plenty of notice so she can have a change of clothes and book enough time to do it all but it sounds like a great date

I do a lot of dates in public settings from dinner to pool time to shows. I am a beautiful woman & used to people staring doesn't matter if I'm alone of with someone. Let them stare & have fun focusing on your date. You will be too busy having fun to worry I promise.

during my stay at the same hotel... no. If so, well of course I am going to be uncomfortable being seen with various men at the same place. I have worked in the hospitality industry before and I can assure you... we notice.

-- Modified on 4/26/2015 7:26:16 PM

Beautiful women are accustomed to strangers looking at them... they have dealt with it since they were probably 16.  The issue likely won't be people looking, but I guess it could be that she might not want to hang out at the pool with you if she lives in Miami.  What about having a lady you already know join you or meet you there?