First overnight

[peter]

Hi there

 

I have just recently booked an overnight session with an escort for the very first time and I'm unsure what I should I do? We haven't confirmed times but he will be staying at my hotel room overnight and leaving in the morning. Apart from the obvious what sort of things typically happen on an overnight? I have only ever had 1 hour sessions before and not too many of them. Any advice would be greatly appreciated thank you

[liubit]

Every overnight is different, @peter. Everything varies: from amount of time spent, to number of fun times, to activities. Talk to your escort to set everything up. Remember, communication, communication, communication is the key.

 

In my case, a typical overnight usually ran from 7pm to 7-8 am. Introductory light or heavy fun, dinner, heavy fun, sleep, maybe some middle-of-the-night fun, definitely morning fun, optional breakfast, and goodbye kisses. But it varies, I cannot stress it enough. Good luck.

[spider]

My pattern is more or less:

 

Meet at about 7.

Have some wine and wild monkey sex.

Go out for dinner at a nice place. Or if we’re really mellow just order in a pizza or something.

A bit of personal time to check email and messages.

Second round of fun - slower, more mellow.

Sleepy time.

Often, middle of the night round, usually just oral. This is often impromptu. I get up to pee, slip back into bed put an arm around him and start to play a little bit. He begins to respond and it goes from there.

Morning. One more round often starting in the shower. Maybe followed by breakfast, maybe not.

 

I actually prefer a longer daytime session:

 

Meet in the afternoon and have that wild monkey sex as above.

Go out and do something together - museum or whatever. Sometimes he just shows me around town.

Back to hotel for drinks and sex and cleanup for dinner out somewhere.

Back to hotel for the last round of just great low key sex.

He’s out the door by about midnight and I get a good night’s sleep.

Edited June 12, 2019 by spider

[+ BenjaminNicholas]

Every overnight is different, @peter. Everything varies: from amount of time spent, to number of fun times, to activities. Talk to your escort to set everything up. Remember, communication, communication, communication is the key.

 

This.

 

Don't listen to the timetables of a dozen online guys you don't know: Think about your needs, communicate them and hopefully you've picked a guy who can take your cues and run with them.

[+ azdr0710]

have you already met this guy before for one of the one-hours??.....I really hope so!!.........

 

treat the overnight like you're hanging out with a buddy......don't overplan it (don't cram too much into the schedule), ask what he'd like to do, give him some time to himself to do some personal chores (as suggested upthread)......

 

are you ok sleeping with somebody in the same bed?....or same room?.....(I'm not)

 

smile, don't try to impress him, talk slowly, be yourself

[hypothetically]

Apart from the obvious what sort of things typically happen on an overnight?

 

Whatever you would like to happen. Communicate your ideal scenario to the provider so he has a general feel of where you’d like the evening to go, but let everything happen organically. Relax and have fun.

[spider]

This.

 

Don't listen to the timetables of a dozen online guys you don't know: Think about your needs, communicate them and hopefully you've picked a guy who can take your cues and run with them.

 

The OP asked us “what should I do...any advice?” and now I’m being criticized for doing exactly that? Jeez.

[+ BenjaminNicholas]

The OP asked us “what should I do...any advice?” and now I’m being criticized for doing exactly that? Jeez.

 

Thicker skin sir. That wasn't criticism. You'll know when I'm being critical.

 

What I offered was the advice he actually needed to hear: Advice that cuts through confusion and will serve him well into multiple meets.

[peter]

have you already met this guy before for one of the one-hours??.....I really hope so!!.........

 

treat the overnight like you're hanging out with a buddy......don't overplan it (don't cram too much into the schedule), ask what he'd like to do, give him some time to himself to do some personal chores (as suggested upthread)......

 

are you ok sleeping with somebody in the same bed?....or same room?.....(I'm not)

 

smile, don't try to impress him, talk slowly, be yourself

Hi yes I have met him before and he was really good. I will ask him what he would like to do as well and what normally happens on his overnights thanks

[jawjateck]

Longer meetings are awesome. You just have to start doing them to figure them out. With practice, you refine your needs and fantasies, how to communicate and set up successful meets, etc. Have a great time!

[+ Pensant]

Longer meetings are awesome. You just have to start doing them to figure them out. With practice, you refine your needs and fantasies, how to communicate and set up successful meets, etc. Have a great time!

Well put. My regular arrives tomorrow night for three nights. I’ve lost count of the number of meets, which I suppose is a good thing!

[MscleLovr]

I'm unsure what I should I do?

 

You have a lot of good advice above, especially from @liubit I did a lot of overnight dates and as it happens, I had a very similar routine to that outlined by @liubit and @spider

 

My strong advice would be that you must decide what you need/want. If you want a BFE with lots of kissing and cuddling, say so; if you like to bottom, prepare well and tell the guy; and if you only top, tell the guy that so he can prepare.

 

FWIW I disagree with the advice from @azdr0710. I would NOT ask what he wants to do (tho I always asked about his diet before booking dinner) and I certainly would NOT allow time for his “personal chores” - for goodness sake, it’s only 10-12 hours and you’re paying for him to focus on you and your needs, tho you should allow him to shower by himself after you’ve had fun ;-)

[+ tassojunior]

I have had escort friends admit that a few overnights have meant vigorous sex all night usually with young clients and that intrigues me if I ever get Trimix. My #1 would enjoy that but as a top 2 hours is my normal limit even with Cialis and Viagra. Otherwise since I have regulars who live with me off and on for long visits, the concept of paying them to sleep at my house is a foreign concept for me at least.

 

When on visits to other cities I prefer seeing an especially hot guy early in the day for sex and then again later at night after which I get decent sleep. That always works out better money-wise, usually half what an overnight costs. And that helps them as they usually have the most other clients in early evening. BFE or not, you have to realize this is a guy's livelihood and helping them make the most money is a compliment. I can't see paying a guy for me to provide them dinner or a place to sleep otherwise. What they do outside our sex is their business also (except for my whoreish #1, another story).

 

This is just to reinforce what @liubit said about every overnight being different. It's not always "play around/dinner/sex/sleep/play-around/goodbye". And the concept of all-night rough sex intrigues me immensely. Different strokes for different folks.

[spider]

You have a lot of good advice above, especially from @liubit I did a lot of overnight dates and as it happens, I had a very similar routine to that outlined by @liubit and @spider

 

My strong advice would be that you must decide what you need/want. If you want a BFE with lots of kissing and cuddling, say so; if you like to bottom, prepare well and tell the guy; and if you only top, tell the guy that so he can prepare.

 

FWIW I disagree with the advice from @azdr0710. I would NOT ask what he wants to do (tho I always asked about his diet before booking dinner) and I certainly would NOT allow time for his “personal chores” - for goodness sake, it’s only 10-12 hours and you’re paying for him to focus on you and your needs, tho you should allow him to shower by himself after you’ve had fun ;-)

 

When I said allow personal time I was thinking of a few minutes. Rather than sneaking looks at our phones it just seem much better to suggest a short break to catch up on things. I really don’t need it, but I think it’s polite to just ask “would you like a few minutes to check your mail and texts? I wouldn’t mind doing the same.” Overnight maybe not necessary but certainly for a multi-day meeting. But in that case it’s easier. You can just say “I’m going to go find us some coffee, I’ll be back in a few”. It gives you both a bit of time alone to do such things.

[GTMike]

Hi there

 

I have just recently booked an overnight session with an escort for the very first time and I'm unsure what I should I do? We haven't confirmed times but he will be staying at my hotel room overnight and leaving in the morning. Apart from the obvious what sort of things typically happen on an overnight? I have only ever had 1 hour sessions before and not too many of them. Any advice would be greatly appreciated thank you

Good question and lots of various good answers irrespective of the apparent contradictions. You never know for sure what chemistry might exist between you guys so in some cases one person's approach and advice above might work out better in that specific scenario versus anothers advice but all worthy to consider. In my case i always host the overnight and am very comfortable in the setting and can be very flexible, so i do my best to make the environment as most comfortable and relaxed for the gentlemen as possible. For a first timer the most awkward situation i've faced throughout the years is how to communicate when it might be time for "fun time" (which means going upstairs to play for the 1st time), and to get a sense whether the person thinks that means the rest of the night is just that then sleep? Or does that mean go have fun for an hour for example and then rinse, watch a movie or something and repeat a couple times throughout the rest of the night. So i agree with everyone suggesting to "communicate". Once we meet for a while into the evening, (again this is for a 1st timer and I'm hosting) i set broad expectations (if we haven't yet) or confirm them, but do so in a balanced way so the guy understands what I'm looking for and what to expect. But be perpared to be flexible and don't over do it like micro-managing a situation. That's why i also agree with "asking" what the person might want to do, but that question is in relation to and should fit into whatever context the overrrideing broad plan was that you guys mutually decided worked well for both of you. Hopefully this helps a bit.

[+ WilliamM]

@azdr0710 gave excellent advice: treat the overnight like you are hanging out with a buddy.

 

I did not know what with a quiet

but knowledgeable college student from New York state who met me in Philadelphia in 1991. We metb in a bar in New York City, and I wanted him badly. But, we also talked on the phone often. So we knew each other. And the conversation continued, until he took his clothes off. He stayed until the next evening

[MscleLovr]

escort friends admit that a few overnights have meant vigorous sex all night usually with young clients

 

We don’t know how old @peter is - if he’s young, this may be very interesting info for him.

 

A few years back, when I was in my 50s, I had the same ‘admission’ made to me by a very hot blond muscleboy (a dedicated bottom with a submissive streak). I’d enjoyed several dates with him before I suggested playing overnight. He asked what I had in mind and I outlined my usual routine, also stating there’d be 7 hours sleep and he could decide where we had dinner. He was unsure what to charge me, so we left that part vague.

 

On the day, he arrived around 5pm and left before 9am. We had great fun together and I ended up topping him 3x and he also sucked me off to completion 2x. In the morning, he told me it’d been very enjoyable as he liked how I fucked him and he’d had 7 hours sleep...so he charged me 3x his (quite high) hourly rate. He confided that I was only the 2nd guy to play with him overnight.

 

His first overnight had been 2 weeks earlier with a guy of 30 who topped him 6x in the night and he (the bottom) was unable to sleep and felt very fully “used” by the morning. So he charged the guy 5x his hourly rate.

[+ WilliamM]

We don’t know how old @peter is - if he’s young, this may be very interesting info for him.

 

A few years back, when I was in my 50s, I had the same ‘admission’ made to me by a very hot blond muscleboy (a dedicated bottom with a submissive streak). I’d enjoyed several dates with him before I suggested playing overnight. He asked what I had in mind and I outlined my usual routine, also stating there’d be 7 hours sleep and he could decide where we had dinner. He was unsure what to charge me, so we left that part vague.

 

On the day, he arrived around 5pm and left before 9am. We had great fun together and I ended up topping him 3x and he also sucked me off to completion 2x. In the morning, he told me it’d been very enjoyable as he liked how I fucked him and he’d had 7 hours sleep...so he charged me 3x his (quite high) hourly rate. He confided that I was only the 2nd guy to play with him overnight.

 

His first overnight had been 2 weeks earlier with a guy of 30 who topped him 6x in the night and he (the bottom) was unable to sleep and felt very fully “used” by the morning. So he charged the guy 5x his hourly rate.

 

Thanks, @MscleLovr excellent contribution.

[peter]

Hey thanks everyone for the advice I am 30 so would be up to extended sessions with him. Also i have asked him what he would like to do as well. Reading the posts has really helped me so thanks to everyone who posted

[+ nycman]

I’d also suggest keeping your expectations low. I’ve rarely had overnights

work out well, even though the vast majority were with guys I had had

incredible 1-2 hour sessions with before.

 

If fact the few great overnights I’ve had were with guys I’d never hired

before. Nonetheless, I don’t recommend it.

 

I really enjoy having dinner with my escorts and I don’t mind paying for

their company or their “time”, but I do find most overnight rates to

be excessively high (especially in the US).

 

At this point I stick with 1-2 hour sessions before dinner and then invite

the escort to dinner if we’re really hitting it off. Most politely decline.

No problem.

 

I’d love to find a dude who can truly “escort” in all senses of the word.

They are a rare breed.

[Smurof]

I have never understood the overnight hire unless necessary. A prolonged period of time like that to me would need to be a weekend getaway hire to be worthwhile. Otherwise, I'm donating hundreds more to hear him snore and eat breakfast.

[MscleLovr]

Hey thanks everyone for the advice I am 30 so would be up to extended sessions with him. Also i have asked him what he would like to do as well. Reading the posts has really helped me so thanks to everyone who posted

 

Hope it goes very well for you. Please report back afterwards @peter

[desertguy1954]

Relax and enjoy. The important thing is to communicate with each other as to what some of the expectations you both have.

The first time I hired for 24 hrs, I was very nervous. I let him know that and we texted back and forth for the months leading up to our meeting. I started relaxing the minute I opened the door and saw that wonderful smiling face.

Sometimes the text from him was to just say hello and see how things were going. I found a nice place close to the beach and we had a fantastic time. This year, we spent three fantastic days together. I got a place right across from beach. Looking forward to the next time we see each other.