mood strikes me for multi-hour sessions like you are planning, so I haven't jerked off in nearly 20 years.  

 
If you are good for MSOG and can manage three, most providers give a pretty good massage, so you can divide the 5 hours like this . . . . fuck, massage, fuck, massage, fuck.  If you are not anticipating being able to have that much sex, then a meal can be added, or watch a movie together, or teach her how to play backgammon for money and then win half the donation back.  

Are you sure about seeing her for 5 hours? If you get in that room and for some reason you dont click, maybe a personality difference for example, that is a disaster for you waiting to happen and the money for that kind of session is no doubt exorbitant. I would suggest you see her first for a 90 mins or 2 hour date first but that is just my 2 cents.

 
I have done the 5 hour+ date on many occasions and with the right girl, they can be an awesome experience. I usually start with Champagne/wine with appetizers i.e. cheese/crackers/fruit/hummus etc. That gives you plenty of chat time and allows the girl to feel comfortable with you. For these type of dates I like to do outcall so I can prepare everything before the girl arrives. I also like to get a suite, as a an ordinary hotel room can be a bit cramped for that amount of time.  

 
Typically I also bring a bottle for cold shots as they are always fun. Many women love the flavored vodkas or something like Fireball, a cinnamon whiskey but I get the girls take on that first. A small gift at the end can cap a truly memorable experience.

You don't say if she requires "public time". Many providers do require you spend time time outside the room, something like lunch or dinner.
I have done a number of these and always bring my own condoms and lube, just in case. I don't drink on dates but you may consider wine and some snacks.  
If you have any interest in it, ask her if she has various types of toys.
Above all, discuss with her what you are looking for.

Do long dates, usually four hours though.  We start with dinner.  I usually try to get a booth and sit on the same side.  Get close and see how affectionate she is.  Does she touch your arm, leg, give pecks on the cheek or lips occasionally when you say something funny?  Try to build a rapport.  Lots of flirting.  It's a wonderful way to start the evening.

Take a good hour at least at dinner.  Drinks, appetizer, main dish.  Then I recommend getting a dessert to go.  Take it back to your room and refrigerate for later.

Start on the couch and move slow.  Lots of foreplay, you have the time.  

Enjoy the dessert together between play.  Show off pictures of your kids or other things you can talk about.

If you want to abstinate beforehand that will make your first orgasm quite powerful but you may need more time between sessions to wake up.

Anyway, I think you will enjoy the experience.  Quite curious who this is you're seeing.

Carry some Tylenol and a good book to read.. I hope you like reading...  LOL...  

 
Bitches start yapping too much, I tune them out and bury myself in a book.

You asked this on the newbie board, so how did that date work out??? Did you end up finger bangin her at the restaurant?...lol.

-- Modified on 11/10/2022 9:17:40 PM

5 Hours

Just my ten cents....

Take her out for a 30 minute coffee date.
If the conversation is lively with natural flow
and you feel instant chemistry,  then proceed.

Five hours is significant for one of you to just
fall asleep after the first three hours......zzzzz

-- Modified on 11/11/2022 2:35:17 PM

Get round one out of the way, then dinner,  then round 2...and 3.

A five hour session with a new provider is just plain stupid in my opinion. If you live close to her and she’s in your town why not spread that time over days or weeks? I’m in this for the sex, not dinner or conversation, and five one hour sessions or even a one and then two two hour sessions will probably result in 4x or 5x more actual engaged sex time!  

Also, I like to mentally review a session for some time while planning my next session! What did I like? What did she like? What positions did we forget to try?  

When I click with a provider and then I return shortly thereafter, she usually seems genuinely excited and appreciative of the return! This is a great time for a two hour session! In every case I think I can say the experience gets more intimate, and the sex gets better with 3-4 repeat sessions over a month than when compared to one marathon session.

This is just my approach, although I realize we all have different time constraints and budgets!

I live somewhere not that close to high end providers so shorter appointments with upscale providers aren't really an option.

Thanks to everyone for the above

secrtasianman128,
  First of all, If I was you. I never would have scheduled a long 5 hour session with any Escort (High End or not). You got to figure out what to do during those sessions. Are you going out for 3 to 4 hours then heading back to her place? Be safe!!!