24 hours with an escort

[rml]

So I have made arrangements for an extended period of time with an escort (noon to noon) at the end of this month. I'm wondering what I should plan - meals, activities in & out of the bedroom, giving him some quiet time if he would like, etc. I've done overnights before (Billy Herrington RIP); this will be the longest date in my history.

 

Any thoughts?

[+ Avalon]

Your place? His place? Hotel?

 

There should be three meals - lunch, dinner, breakfast.

 

Are there places to do things where you live?

 

Because it's only 24 hours I wouldn't think he'd need quiet time.

 

How many times do you expect to climax? Him to climax?

 

Lots to consider.

[MiamiLooker]

So I have made arrangements for an extended period of time with an escort (noon to noon) at the end of this month. I'm wondering what I should plan - meals, activities in & out of the bedroom, giving him some quiet time if he would like, etc. I've done overnights before (Billy Herrington RIP); this will be the longest date in my history.

 

Any thoughts?

Wouldn't you want to discuss this with the escort so you both have the same expectations for the appointment?

[rml]

Your place? His place? Hotel? During the day, my place. Then overnight in a hotel.

 

There should be three meals - lunch, dinner, breakfast. Perfect; that's what I am thinking.

 

Are there places to do things where you live? Currently researching...

 

Because it's only 24 hours I wouldn't think he'd need quiet time.

 

How many times do you expect to climax? Him to climax? Is 3 too many? Not enough?

 

Lots to consider.

[rml]

Wouldn't you want to discuss this with the escort so you both have the same expectations for the appointment?

 

Absolutely. I just am looking for things to consider, before I start the asking process.

[nsguy45]

So I have made arrangements for an extended period of time with an escort (noon to noon) at the end of this month. I'm wondering what I should plan - meals, activities in & out of the bedroom, giving him some quiet time if he would like, etc. I've done overnights before (Billy Herrington RIP); this will be the longest date in my history.

 

Any thoughts?

Why 24 hours? The longest I've ever gone with an escort is 12, 7:00 PM to 7:00 AM. That included dinner out, a movie in and lots of sack time and pillow talk.

[rml]

Why 24 hours? The longest I've ever gone with an escort is 12, 7:00 PM to 7:00 AM. That included dinner out, a movie in and lots of sack time and pillow talk.

 

It's just how the timing worked out. It's going to be a new personal best for me

[Shawn Monroe]

I’ve done a few “extended period of time” arrangements, the longest being Friday at 1am (about when my flight got in) to Saturday at 7am (enough time for me to fly home and get to Texas for a wedding).

 

Though there was a lot of discussion and lead time, we didn’t discuss too much of the specifics before, though some was implied.

 

Started with a massage and HE. then we slept in, breakfast in bed, he showed me some of the city, then dinner and a comedy show, then more some more fun.

 

So I think we both got off twice. No down time for me. In a few instances where I’ve had a longer arrangement, an event - something where I was a companion like a concert or comedy show - worked well.

 

But it does at least work to have some of the arrangemeents worked out beforehand.

[rml]

I’ve done a few “extended period of time” arrangements, the longest being Friday at 1am (about when my flight got in) to Saturday at 7am (enough time for me to fly home and get to Texas for a wedding).

 

Though there was a lot of discussion and lead time, we didn’t discuss too much of the specifics before, though some was implied.

 

Started with a massage and HE. then we slept in, breakfast in bed, he showed me some of the city, then dinner and a comedy show, then more some more fun.

 

So I think we both got off twice. No down time for me. In a few instances where I’ve had a longer arrangement, an event - something where I was a companion like a concert or comedy show - worked well.

 

But it does at least work to have some of the arrangemeents worked out beforehand.

 

Thank you Shawn!

[+ Pensant]

I prefer weekend engagements and those I’ve spent time with have usually had such a high level of rapport with me that we’ve both been shocked at how quickly the time flew by. I’m pretty chill, so I’ve had no problem if a provider wanted to go to a party one of the nights. I enjoyed a good night’s sleep and they were back early the next morning. The successful weekends and overnights were always preceded by a shorter session, to establish compatibility. When arranging an overnight with an untested provider, the satisfaction level dropped considerably.

[+ BenjaminNicholas]

So I have made arrangements for an extended period of time with an escort (noon to noon) at the end of this month. I'm wondering what I should plan - meals, activities in & out of the bedroom, giving him some quiet time if he would like, etc. I've done overnights before (Billy Herrington RIP); this will be the longest date in my history.

 

Any thoughts?

 

 

Don't overthink or plan it. Just communicate openly with him and go with the flow.

 

I just spent 10 days in Hawaii with a regular. It went by in a flash. And we made zero plans beforehand.

[Jomo]

I've spent a couple of weekends with an escort. Started out shorter than that, and grew from there. They've all been a blast. I would talk to him about what he'd be interested in outside of the sack. Whether it being zip lining, car racing, shopping, museums, jumping out of a perfectly fine airplane, etc. u gotta get out of the room, or you'll both go stir crazy. Have fun!

[big-n-tall]

I say maybe have a basic structure of what you want to do, but don't have a hard and fast schedule unless you booked something for a specific time (like a play, a movie, etc.). As for how much sexy time you have, a lot of it has to do with chemistry and how horny you both are. You might need to discuss the quantity you expect. Some guys are very much one and done after orgasm. Others are like rabbits and not only can keep going for hours but do it multiple times a day.

 

The most time I've spent with a working guy (on the clock) was 4 days. I will be spending 5 days with that same guy later this summer. Basically, nothing was planned/set in stone, except one reservation I made ahead of time. We did stuff each day on a whim. Two of the four days we had sexy time twice in one day, in one day 3 times, and the other day 4. I gave him the opportunity for alone time and to venture out on his own if he so chose. However, except for when he went to work out, he wanted to go with me everywhere. There was very little physical separation.

[cany10011]

I guess it depends what your escort is interested in as well. Or, is he visiting your city? Are there any sights you would take a friend/visitor? How about restaurants - food preferences? What about a show or activity you can participate in together? 24 hours is really not much time if you include sleeping and fucking, so just limit to something in the afternoon/early evening and dinner. The next day, you will likely like to fool around before bfast and noon is around the corner with not much time in between.

[rml]

Great comments everyone; I appreciate all your insights!

[hougalwizard]

To change up the scenario a bit: Is is appropriate to set up a multi-day visit to the provider’s city (but not necessarily his own abode), and ask him for a basic suggested (basic) itinerary? If the visit were for more than 24 hours, having separate places might allow for some alone time, more akin to a real dating situation, IMHO. Moreover, it keeps the arrangement from being too much like a sex AirB&B and guide service (which is a whole ‘nother scenario/question area).

[ncc1701d]

I say maybe have a basic structure of what you want to do, but don't have a hard and fast schedule unless you booked something for a specific time (like a play, a movie, etc.). As for how much sexy time you have, a lot of it has to do with chemistry and how horny you both are. You might need to discuss the quantity you expect. Some guys are very much one and done after orgasm. Others are like rabbits and not only can keep going for hours but do it multiple times a day.

 

The most time I've spent with a working guy (on the clock) was 4 days. I will be spending 5 days with that same guy later this summer. Basically, nothing was planned/set in stone, except one reservation I made ahead of time. We did stuff each day on a whim. Two of the four days we had sexy time twice in one day, in one day 3 times, and the other day 4. I gave him the opportunity for alone time and to venture out on his own if he so chose. However, except for when he went to work out, he wanted to go with me everywhere. There was very little physical separation.

 

Wow 3-4 times a day!! Care to name that escort, even if in PM?

My longest was 5 days, and it was twice a day of fun, and of course gym/email time for him (and me) daily, with meals etc. Some planned and unplanned activities.

[big-n-tall]

Wow 3-4 times a day!! Care to name that escort, even if in PM?

My longest was 5 days, and it was twice a day of fun, and of course gym/email time for him (and me) daily, with meals etc. Some planned and unplanned activities.

 

The guy in question isn’t currently advertising. So I don’t feel ok with naming him, even in private.

 

Besides, of the 4 days we were together, two of the days, sexy time was only twice a day. It wasn’t a constant barrage of sex. Seriously though, I don’t know if he is that sexual with everybody. We have very, and I do mean very, good chemistry. Like I mentioned, when given the opportunity for his alone time, he refused and preferred to stay in my company. The only time we were apart was during his workout time. Even then I think if I wanted I could have gone to workout with him.

 

With that said, another guy (who is advertising) I had a lot of sexy time with in the short 2 days we were together was Kristian Elix. That man is amazing and insatiable. He was my 1st multiple day hire, so I wasn’t sure how much I should initiate sexy time. I think if I could have handled it... we could have gone almost non-stop. I wish he would travel more. I don’t get to see him as much as I’d like.

[big-n-tall]

To change up the scenario a bit: Is is appropriate to set up a multi-day visit to the provider’s city (but not necessarily his own abode), and ask him for a basic suggested (basic) itinerary? If the visit were for more than 24 hours, having separate places might allow for some alone time, more akin to a real dating situation, IMHO. Moreover, it keeps the arrangement from being too much like a sex AirB&B and guide service (which is a whole ‘nother scenario/question area).

 

I don’t think that would be a problem. Some guys like to play tour guide if you visit their city. As in all things, talk to the provider you are interested in. At most we on the forum can only give you suggestions. The provider you choose can answer all your questions and agree or disagree to your terms or desires.

[Ryan Roman]

So I have made arrangements for an extended period of time with an escort (noon to noon) at the end of this month. I'm wondering what I should plan - meals, activities in & out of the bedroom, giving him some quiet time if he would like, etc. I've done overnights before (Billy Herrington RIP); this will be the longest date in my history.

 

Any thoughts?

 

I have a regular client that will book me for 3 nights. Other than discussing places to stay while he is in town, we tend to spend most our time in the hotel room and only venturing out for lunch or dinner. It never hurts to have a few details organized in advance... IMO...

[Racketjock]

As another has said, good communication is key. I've had a few extended times with trusted and long term escort relationships. We have usually each picked places we want to see, places we want to eat, and things of interest then work around what makes for fun and relaxation. I have been lucky and since they are prior hires, never had an issue with having more fun time in the sack that I could handle! My two cents is to communicate and do so with someone you have spent some time with before and are comfortable.

[gallahadesquire]

Make sure that you have plenty of space. One of my regulars I see for multiple days at a time, and he knows just to take time when he needs it, which is usually first thing in the morning when he disappears for an hour. What and/or who is he doing? Don't really want to know.

 

Space, though ... if possible, get a suite, not just a room. At WDW during the Winter Olympics 2006, we had a bedroom and a living room. That fellow hated sleeping together, so he got the couch by his own choice. But there was a kitchen and other places to hang out.

[+ Avalon]

I have a regular client that will book me for 3 nights. Other than discussing places to stay while he is in town, we tend to spend most our time in the hotel room and only venturing out for lunch or dinner. It never hurts to have a few details organized in advance... IMO...

 

Too bad the hotel doesn't have room service. ;-)))

[Floridasexman]

Booking an escort for the weekend. The city is large and lots to do

May I assume we should act like boyfriends the entite weekend?

[MiamiLooker]

Booking an escort for the weekend. The city is large and lots to do

May I assume we should act like boyfriends the entite weekend?

assume nothing