Overnight with an escort

[MscleLovr]

8 hours ago, starman05 said:

The one thing I regret is not asking him to whisper into my ear.…that he loved me.….Silly, I know.

This brought up a memory.
Years back, I was a volunteer at a sexual health charity and one time, I was hosting a discussion between 6 young male sex workers They shared details of various encounters with male clients.

One spoke of a man (married to a woman) who was muscled and in good shape. He liked to fuck a young man from behind. While he was pumping vigorously, he insisted the young man turn his head to look at him and say “I love you” as he came to climax.

That made the others chuckle. It turned out that the married man had sex at numerous times with each of them. And every time he required the young man to state “I love you”.

[Vin Marco]

On 5/30/2024 at 7:24 PM, Muscleking said:

5/6 hours of fun then he goes home

Seems a bit "rushed"  ( for an overnight if that's how he defines it ) 

Edited September 21, 2024 by Vin Marco

[whatdoidowiththisagain]

New to the hobby but I've been wondering why clients book overnights with providers. To me, I get everything I want from  1-2 hours. But I'm curious, what do you want from/ do get from overnights? I'm somewhat socially awkward and feel like I would run out of things to do, but I could see myself groping his dick for most of that time and enjoy more foreplay. I also have a slightly deviated septum so i snore and am self conscious about keeping him awake haha. Providers, do you care if the client is a snorer?

[56harrisond]

On 5/31/2024 at 3:36 AM, Simon Suraci said:

Overnights are different for everyone. You, the client, communicate what you want and what you expect. Your provider will propose a fee, a timeframe, and you go from there to land on a mutually agreeable arrangement.

Typical overnights are around 12 hours, sometimes a bit less, sometimes a bit more. Baseline: 9pm-9am. Maybe start earlier or end later. You negotiate and agree on expectations ahead of time in terms of duration, activities in bed, activities outside of bed, how much (if any) sleep you expect to get, sleeping arrangements, and the fee.

You might start early evening with dinner, maybe cocktails, or whatever relaxation activity floats your boat. See a movie, visit an art show, go to the beach, dance at a club, play video games, go shopping, whatever the client wants based on his interests. A lot of times it looks like a traditional nice dinner date. You talk, you flirt, you connect. Some of my clients like me to give them a massage, body scrub, and manscaping in addition to, or instead of, meals or other going out activities. It can look however you want. 

Then the really fun part. Usually one or more rounds of sexual activities you like, often going into the wee hours. It could last from 2-4 hours, maybe more, depending on a few factors. You might break these romps up with snacks, laying in one another’s arms, talking, watching a show, or what have you. For some of you kinky bitches, these can be pretty long, drawn out, and elaborate sessions. Maybe others join (arranged ahead), but usually just 1:1. 

Then some sleep. Perhaps only a few hours. Maybe 6-8 if the client is satisfied with plenty of action the night before and the morning after. You might like to sleep cuddled up with your provider. Or in an adjacent hotel bed, or in completely separate rooms at your home, or whatever works best for you both.

Some clients want and expect their provider to stay up all night. That’s ok too, but please do communicate your expectations up front. Most of us can’t go for 5-10 hours at a time just having sex, and not everyone will be good company staying up that late. There’s a natural limit. Drugs are another matter, however. If you want to party, be sure to find a compatible provider and be upfront with your expectations. 

After some nap time, you might wake up to your man initiating another round of sex. Morning wood is raging. Things happen. Then coffee/tea, breakfast, more chatter, showering, and getting dressed. Maybe you skip breakfast and go out for brunch.

Pay your provider, and he’s on his way!

 

[DznNYC]

5 hours ago, 56harrisond said:

 

This is actually super helpful!   I’m just starting to book some overnights right now.  So this is all excellent to keep in mind!    🙏🏻 

[whatdoidowiththisagain]

yes. you have some good ideas. i thought overnights were just like sex and sleep over haha. are the majority of them usually 12 hours? Just so i know if i'm being ripped off

[big-n-tall]

My area gets traveling providers, but not many I want to hire. So I started doing overnights because guys I was most interested in were located in other states. Many would not come to my area and I wasn't going to fly/train to an area for just a couple hours of meet up time.

As I got more comfortable with hiring, I started hiring for overnights (or longer), either bringing someone in or going to them. On a side note, I know people say don't hire someone for a overnight you have not met prior. However the majority of my overnights have been with guys I had not met. Most of these worked out for me. I can count on one hand the ones that didn't. I guess I have a good meter for selecting compatible providers.

Anyway... an overnight or longer is what you make it. Meaning it's not just limited to sex and sleeping. If you have a mutual interest or either of you are visiting a new area, it can be fun to explore together. The experience also can be different with each provider because some providers are more sexual and some are one and done (take a long time to recuperate).

Once I started doing overnights, I really started to enjoy the connections developed... the time to explore each other more and not feel rushed. A number of guys I have seen for overnights want to literally hole up in a hotel room and have sex as much as possible. Some like to be more of boyfriend experience and cuddle a lot, go to a nice dinner, etc.

Before you set an overnight up the key is communication. There should be no assumptions between the two of you.

Edited February 1 by big-n-tall

[Hot4latin]

2 hours ago, whatdoidowiththisagain said:

yes. you have some good ideas. i thought overnights were just like sex and sleep over haha. are the majority of them usually 12 hours? Just so i know if i'm being ripped off

Once you get out of the mindset of value assessment and risk aversion, you’ll be ready for an overnight with that provider. At that point, it will be all about the comprehensive experience. 

[Rod Hagen]

Many times I've written here on the joys of overnights.

All I'll say this time is, Coffee.  Wether you're the escort or you're the client (or for that matter you're partnered), bringing the other coffee in bed, or being the man receiving the coffee in bed first thing, is exceedingly romantic.  Sipping the coffee while getting morning head is especially hot.  Bringing a man a cup of coffee before he even rises to pee is an easy way to say: I care for you, enjoy this.

Edited February 1 by Rod Hagen

[+ BenjaminNicholas]

On 1/31/2025 at 2:23 PM, whatdoidowiththisagain said:

yes. you have some good ideas. i thought overnights were just like sex and sleep over haha. are the majority of them usually 12 hours? Just so i know if i'm being ripped off

If all you think about is being ripped off and money, you might not really be built for longer term engagements.

Edited February 2 by BenjaminNicholas

[whatdoidowiththisagain]

2 hours ago, BenjaminNicholas said:

If all you think about is being ripped off and money, you might not really be built for longer term engagements.

Not sure If "all you think about is being ripped off and money" is a fair generalization here. First and foremost it's important to not be naive about such things as the value of your money in a transactional relationship.  Let's not fool ourselves into believing that escorts in general do this because they want a relationship beyond the transactional one. Many escorts as well documented here on this forum are more than willing to take advantage of people. 

I sense an air of haughtiness that overly romanticizes this hobby in many here. Let's give ourselves a reality check

[+ Jamie21]

Reality check: you hired a guy you really like for an overnight. 12 hours. The evening started well, a drink in the bar, some flirting, getting to know each other. He’s engaging, intriguing, sexy. He looks only at you as you talk, he touches your hand as it rests on your thigh, he squeezes it while he casually orders you another drink. 

Over dinner he listens to your stories, smiling, nodding, asking questions. All the while dropping you teasers about what will happen later, in the bedroom both on and off the bed…especially off the bed. You’re hard under the table, driven there by the anticipation he’s built up. As you eat dessert your excitement causes you to get some ice cream on your fingers. He reaches over, takes your creamy hand slowly lifts it to his face, and licks your fingers clean… all the while maintaining eye contact with you. 

The lift takes for ever to reach your floor, stopping at every floor to let people out. He’s holding your hand, standing so close to you that you’re sure he can feel your heart beating. Now there’s just the two of you plus a hotel employee, who must be going to your floor, because the only remaining floor button lit up is yours. The lift ascends and as it does he leans in and kisses you, cradling your head with his hand, his body pressing you against the lift wall. The hotel employee turns to face the doors, and she exits quickly as they open on your floor. You try to move towards the door but he’s pinned you to the wall, kissing you passionately, his hard cock pressed against yours. Finally he steps back and taking your hand he leads you out of the lift and then he pauses, realising he doesn’t know your room number. You look at each other and grin, but before you can do anything he pulls you in for another kiss, and as he does so he reaches around to your back pocket and pulls out your room card, reads the number and silently leads you to the room. 

It’s early hours of the morning. You awake at the glint of light peeking through the gap in the curtains. He’s asleep next to you, facing away from you. Your arm is around his body, your chest against his back, you feel his warmth and slow deep breathing. You recall the two, three, was it four rounds of passionate sex. The shower session, the bedroom floor, the chair. Now he sleeps. A thought pops into your head: I paid $2400 for this, that’s $200 an hour…am I being ripped off for the hours he’s asleep?

 

[Archangel]

14 hours ago, BenjaminNicholas said:

If all you think about is being ripped off and money, you might not really be built for longer term engagements.

I disagree. My overnights have been much less about the minutes and hours, but actual time together. I’m actually hesitant to hire for anything less than an overnight precisely because the clock seems to be ticking in the background. Shorter “engagements” seem much easier to nickel and dime than overnights…Once you’ve committed to a couple hours, provider and client, ten minutes more or less don’t matter as much anymore. 

[+ BenjaminNicholas]

55 minutes ago, Archangel said:

I disagree. My overnights have been much less about the minutes and hours, but actual time together. I’m actually hesitant to hire for anything less than an overnight precisely because the clock seems to be ticking in the background. Shorter “engagements” seem much easier to nickel and dime than overnights…Once you’ve committed to a couple hours, provider and client, ten minutes more or less don’t matter as much anymore. 

We're saying the same thing  

I believe you misinterpreted my post.  

[+ BenjaminNicholas]

12 hours ago, whatdoidowiththisagain said:

Not sure If "all you think about is being ripped off and money" is a fair generalization here. First and foremost it's important to not be naive about such things as the value of your money in a transactional relationship.  Let's not fool ourselves into believing that escorts in general do this because they want a relationship beyond the transactional one. Many escorts as well documented here on this forum are more than willing to take advantage of people. 

I sense an air of haughtiness that overly romanticizes this hobby in many here. Let's give ourselves a reality check

What I said was perfectly straight forward.

Some guys are cut out for longer term and some aren't.  Simple.

This isn't about an escort taking advantage of anyone.  It's not about romanticizing anything.  

 

 

 

[starman05]

6 hours ago, Jamie21 said:

Reality check: you hired a guy you really like for an overnight. 12 hours. The evening started well, a drink in the bar, some flirting, getting to know each other. He’s engaging, intriguing, sexy. He looks only at you as you talk, he touches your hand as it rests on your thigh, he squeezes it while he casually orders you another drink. 

Over dinner he listens to your stories, smiling, nodding, asking questions. All the while dropping you teasers about what will happen later, in the bedroom both on and off the bed…especially off the bed. You’re hard under the table, driven there by the anticipation he’s built up. As you eat dessert your excitement causes you to get some ice cream on your fingers. He reaches over, takes your creamy hand slowly lifts it to his face, and licks your fingers clean… all the while maintaining eye contact with you. 

The lift takes for ever to reach your floor, stopping at every floor to let people out. He’s holding your hand, standing so close to you that you’re sure he can feel your heart beating. Now there’s just the two of you plus a hotel employee, who must be going to your floor, because the only remaining floor button lit up is yours. The lift ascends and as it does he leans in and kisses you, cradling your head with his hand, his body pressing you against the lift wall. The hotel employee turns to face the doors, and she exits quickly as they open on your floor. You try to move towards the door but he’s pinned you to the wall, kissing you passionately, his hard cock pressed against yours. Finally he steps back and taking your hand he leads you out of the lift and then he pauses, realising he doesn’t know your room number. You look at each other and grin, but before you can do anything he pulls you in for another kiss, and as he does so he reaches around to your back pocket and pulls out your room card, reads the number and silently leads you to the room. 

It’s early hours of the morning. You awake at the glint of light peeking through the gap in the curtains. He’s asleep next to you, facing away from you. Your arm is around his body, your chest against his back, you feel his warmth and slow deep breathing. You recall the two, three, was it four rounds of passionate sex. The shower session, the bedroom floor, the chair. Now he sleeps. A thought pops into your head: I paid $2400 for this, that’s $200 an hour…am I being ripped off for the hours he’s asleep?

 

You may be overpaying for the hours he sleeps, but you’re underpaying for the hours he’s awake IF you get the right guy

there are people who are in relationships who have nights like you describe all the time (swoon!)

there are people in relationships who never have nights like you describe

there are people who pay for nights like you described and they’ve been worth every fucking (no pun intended) penny

and then there are people who have never had a night like you describe ☹️

You’re a great writer, btw

the hotel employee riding up in the elevator being a “her” was a nice touch

no competition

 

 

 

 

 

[+ Jamie21]

52 minutes ago, starman05 said:

You’re a great writer, btw

😘

[pubic_assistance]

8 hours ago, Jamie21 said:

You recall the two, three, was it four rounds of passionate sex. The shower session, the bedroom floor, the chair. Now he sleeps. A thought pops into your head: I paid $2400 for this, that’s $200 an hour…am I being ripped off for the hours he’s asleep?

Thank you @Jamie21 Very well put.

Edited February 2 by pubic_assistance
meme

[pubic_assistance]

20 hours ago, starman05 said:

there are people who have never had a night like you describe ☹️

To dismantle a well-coordinated night of passion by a professional escort into an assessment of how many hours he was actually "working" (as in fucking your ass) is kinda humiliating and feels like sex slavery. Perhaps the people who want to calculate the value of each hour have missed the entire point of the experience. How often DO you get the chance to enjoy a romantic evening with an attractive person? If that answer is "never"..then your time was worth a lot more than the hourly rate you are nitpicking over.

Edited February 3 by pubic_assistance
spelling

[starman05]

On 2/2/2025 at 2:04 AM, Jamie21 said:

Reality check: you hired a guy you really like for an overnight. 12 hours. The evening started well, a drink in the bar, some flirting, getting to know each other. He’s engaging, intriguing, sexy. He looks only at you as you talk, he touches your hand as it rests on your thigh, he squeezes it while he casually orders you another drink. 

Over dinner he listens to your stories, smiling, nodding, asking questions. All the while dropping you teasers about what will happen later, in the bedroom both on and off the bed…especially off the bed. You’re hard under the table, driven there by the anticipation he’s built up. As you eat dessert your excitement causes you to get some ice cream on your fingers. He reaches over, takes your creamy hand slowly lifts it to his face, and licks your fingers clean… all the while maintaining eye contact with you. 

The lift takes for ever to reach your floor, stopping at every floor to let people out. He’s holding your hand, standing so close to you that you’re sure he can feel your heart beating. Now there’s just the two of you plus a hotel employee, who must be going to your floor, because the only remaining floor button lit up is yours. The lift ascends and as it does he leans in and kisses you, cradling your head with his hand, his body pressing you against the lift wall. The hotel employee turns to face the doors, and she exits quickly as they open on your floor. You try to move towards the door but he’s pinned you to the wall, kissing you passionately, his hard cock pressed against yours. Finally he steps back and taking your hand he leads you out of the lift and then he pauses, realising he doesn’t know your room number. You look at each other and grin, but before you can do anything he pulls you in for another kiss, and as he does so he reaches around to your back pocket and pulls out your room card, reads the number and silently leads you to the room. 

It’s early hours of the morning. You awake at the glint of light peeking through the gap in the curtains. He’s asleep next to you, facing away from you. Your arm is around his body, your chest against his back, you feel his warmth and slow deep breathing. You recall the two, three, was it four rounds of passionate sex. The shower session, the bedroom floor, the chair. Now he sleeps. A thought pops into your head: I paid $2400 for this, that’s $200 an hour…am I being ripped off for the hours he’s asleep?

 

btw, if there's anyone who can provide a scenario Jamie21 describes (I'm in Los Angeles) shoot me a DM. 

TIA! 

[Thelatin]

I used to do quite a few overnights - they were enjoyable I guess.  But if I’m honest with myself, I just as soon cuddle up with a whiskey and pizza after the guy leaves.  I’m the morning I love breakfast at a good cafe on my own.  
 

I had a great 4 hour date Saturday afternoon.  Then went out for an early dinner.  Ended up in a great conversation with another single guy.

Best day I’ve had in a long time.

[ncc1701d]

Very very interesting to read the wide range of interpretation. I like longer time engagements to have time for both fun and companionship. BUt overnights are not for me who needs his sleep ;-)...i've always thought of it as 12 hr of which at least 6-7 are sleeping. So that leave much less time for fun (once or twice) and chatting and activities (movie, bar or whatever). So i've typically asked for a day session of 6 hrs (typically less $ than ON), or a 24 hr session . BUt this thread confirms my mantra in hiring....be up front and clear...very clear!

[bimuscle]

My two cents.  I will not hire anyone that just gives a 10 to 12 hour window.

[Storm4U]

When I did overnights, I was expected to spend the night, wake-up with them the next morning and give them one more "send off," and sometimes even have breakfast with them before I left.

Edited February 28 by Storm4U

[+ Gar1eth]

 

On 1/31/2025 at 7:46 AM, whatdoidowiththisagain said:

New to the hobby but I've been wondering why clients book overnights with providers. To me, I get everything I want from  1-2 hours. But I'm curious, what do you want from/ do get from overnights? I'm somewhat socially awkward and feel like I would run out of things to do, but I could see myself groping his dick for most of that time and enjoy more foreplay. I also have a slightly deviated septum so i snore and am self conscious about keeping him awake haha. Providers, do you care if the client is a snorer?

In my previous hiring career, I did lots of overnights. ( I don't hire anymore-for one thing I have no money. And even if I did, my libido is mostly in the 'toilet'. My urologist on seeing how low my testosterone level was recently said, "I'm surprised you're awake.")

They were usually around 12 to 14 hours. But I made a night of it. I didn't usually have a lot of friends, so often if the timing worked we'd have dinner and go to a show of some type. It didn't always work out-but that was what I preferred. As for the 'playtime' when we finally made it back to the hotel-well let's  just say that Carol Hall had me in mind when she wrote, "lots of goodwill and maybe one small thrill. But there's nothing dirty going on". So it's not like my playtime lasted that long or would be considered overly strenuous by most experienced providers. 
 

I'm a bit of a night owl-ok-a lot of a night owl. So after a show-and maybe dessert -we might not get back to bed until 1 AM or later to play. Now of course in most cases, I'd discuss the plan of events with the guy to make sure he was ok with that. 
 

As for snoring-I have sleep apnea-and use a bipap machine. I always tried to remember to tell the escort to make sure they could get to sleep with me wearing it. If the escort told me they were a light sleeper, I knew, it wouldn't work out. At least one escort had his  own. So we had dueling machines overnight. 
 

In one case I forgot to mention me using a machine. When I told the escort-before we met- he acted like I was trying to pull something over on him.  And I canceled the meeting. I think he may still be advertising. 
 

In two particular cases that I can remember the guys didn't stay all night (probably happened more than that. But these two episodes stick in my mind. ) In another case one guy didn't even last thru the musical and left at intermission-but that's another story).  
 

These two episode were  not planned that  way (or at least not by me)-one  guy David (hasn't escorted in 20 years as far as I can tell so don't mind using his escort nom de plume) claimed he had bad back problems. It had been a pretty good meeting up to that point. I think we had eaten- and then gone to see a traveling production of Wicked in Miami or Ft. Lauderdale. The escort was nice enough and secure enough that he even allowed a bit of public affection (I'm not talking anything overboard. I think my hand was occasionally on his knee during the performance and vice versa). I think I remember being  mildly  out of sorts when he left. But again the night had been very nice -so I wasn't horribly put out. 
 

The other main time I remember. The escort's initials were AW. He doesn't have a great reputation on here. He was fairly decent to me-seemed a bit stuck on himself. Of course if I had looked like him very possibly -what do I mean possibly-I'd probably be worse. Turns out he was from Texas originally. So that was nice. (Some people on here might remember him)

 

We had gone to a show on broadway. Hugh Jackman was in something called 'The River'. Neither of us was that impressed by the play. After the play we went to The Palms steakhouse. (I wasn't that impressed by The Palms either. I don't know what it is. At a lot of these fancy steak restaurants-I wonder if they grill the steak with butter. Maybe that's not it. But the steaks often taste a bit sour to me.)

 

In any case after the show and dinner, we went back to the hotel. By this time it was very late. We played a bit. I'll have to admit that 'Junior' was a bit over anxious, and I came too soon.  He said he had dogs he had to care for and ended leaving probably around 3 AM. It was a bit disappointing. But on the other hand-often after I had  cum I wasn't that interested in continuing (in other cases I was wanting to cuddle), so I don't think I felt awful-also if I'm recalling right, he wasn't the best kisser. 
 

As for morning play-seems to me that didn't happen often.  But as I said, we often didn't get to sleep until around 3 AM. So the escorts  may have taken that into consideration. 
 

Oh and let me just state for the record-I wasn't into PNP-I'm just naturally a night owl. It's more difficult now that I'm in my 60's. But it's still the way my body time clock skews. 

Edited February 28 by Gar1eth