Overnight with an escort

[cany10011]

7 hours ago, Storm4U said:

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.

One of my best overnights was a Russian guy I met in Stockholm. He woke up before me, rinsed in the shower and gave me a wonderful morning "send off" instinctively... I didn't even know to ask for it, but he just did it. He's wonderful and I met up with him again last year in Warsaw. 

[Luv2play]

11 hours ago, Storm4U said:

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.

Yes. And…..

[MscleLovr]

Interesting thread overall.

i always enjoyed the overnight dates I had. The relaxed times we had talking at a play or gallery visit and over dinner acted as foreplay to the intense erotic times we spent exploring each other.

A big part of an overnight date for me was to have my guy fellate me in the morning. I’d wake up early and shower, and get back into bed to be sucked off to completion. The best times we’d cuddle afterwards and then eat breakfast.
 

If ever I found a potential overnight date wasn’t keen to have morning sex, I’d only arrange 2-3 hours in the afternoon or evening with him.

[Mo Mason]

On 2/2/2025 at 5:04 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?

 

No!  Worth every penny!

[Mo Mason]

On 9/18/2024 at 7:57 AM, SamRockdale said:

To each their own, but evening to late morning allows for play, ample cuddles, and a good morning kiss on the forehead.

You're into cuddles and kissing?  I wouldn't guess that based on your rentmen profiles.  "Toxic College Findom".  Yikes.

[+ BenjaminNicholas]

20 hours ago, Mo Mason said:

You're into cuddles and kissing?  I wouldn't guess that based on your rentmen profiles.  "Toxic College Findom".  Yikes.

Even Sears had a softer side

[TheBossBabyback]

On 2/28/2025 at 3:34 AM, Gar1eth said:

 

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. 

coming home from a play and dinner at 1 or 3 am? You were keeping gilded age all nighter hours. But considering they got to keep their clothes on, it sounds like a good deal. 

[Rod Hagen]

On 2/27/2025 at 10:17 PM, Storm4U said:

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.

Always breakfast . I loved breakfast in the morning with clients.  First blowjobs in bed with roomservice coffee.  Later they roll in the Table (pot of coffee, two doppio espressos, carafe of fresh squeezed orange juice or Watermelon Juice, bread and bakery basket, one dish of eggs and hash or eggs and bacon and one dish of waffle with vanilla and maple sauce, or Lemon Ricotta pancakes (I didn't know that was pedestrian when I was young, I only knew it was delicious), or French Toast and berries, also a bowl of berries) and if possible we ask to have it set up on the balcony, and if no balcony that's ok, because then it's safer for additional blowjobs under the tablecloth.

[Storm4U]

45 minutes ago, Rod Hagen said:

Always breakfast . I loved breakfast in the morning with clients.  First blowjobs in bed with roomservice coffee.  Later they roll in the Table (pot of coffee, two doppio espressos, carafe of fresh squeezed orange juice or Watermelon Juice, bread and bakery basket, one dish of eggs and hash or eggs and bacon and one dish of waffle with vanilla and maple sauce, or Lemon Ricotta pancakes (I didn't know that was pedestrian when I was young, I only knew it was delicious), or French Toast and berries, also a bowl of berries) and if possible we ask to have it set up on the balcony, and if no balcony that's ok, because then it's safer for additional blowjobs under the tablecloth.

Me too! When I think about the parts of the business that I miss… that is one of the things I miss the most!

Edited March 19 by Storm4U

[Pepper Young]

Even though I pursued this hobby for years now, I've never met a provider I'd seriously consider an overnight with. But I finally met one. (I did hire one guy for 5 - 6 hours and it was OK. Never saw him again and he stopped advertising. Just as well.)

Since this was new territory for me I had the usual questions. What is considered "overnight"? To me it's 12 hours. Cost? Just ask him. (My rule of thumb is not to negotiate with these guys. What's worth having is worth paying for. However, I'm not a fool.) Activities? Besides sex, they include dinner, drinks at a downtown bar or club, talk (I love hearing these guy's stories), cuddles. I pay for all extras. Coffee in bed the next morning sounds like heaven. 

Thanks for answering a lot of my questions! 

[Luv2play]

You’re going in the right direction. The only thing I don’t do is coffee in bed in the morning. I like to get up, clean myself up, and head down for breakfast with the escort if in a hotel or down to my kitchen where I make breakfast. 

[Guest]

Overnight is 12 hours. It's always been for at least the last 2 decades for me. 

But definitely ask for the provider's perspective beforehand.

I don't do pnp with escorts, I just really like the sleeping together part. Literal sleeping. So I would hope that the provider is comfortable with that.

[Player1Ready]

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

Hey guys I have a question.. I’m going on a work trip next week, and was chatting with a guy I hire from time to time and he proposed an overnight, I assumed for overnight means you stay with the escort all night have some fun then sleep together and wake up together etc, he explained to me that over night just means spending the whole night together not sleeping together so usually like 5/6 hours of fun then he goes home. 

I’ve never done an overnight so wasn’t sure how it works? Any advices ?

 

Breakfast in bed is a must for me.