Sleeping with Escorts

[Luv2play]

I have racked up quite a bit of experience with sleeping with escorts and found that the experience conditions my likelihood of hiring the same individual again. 
Not all providers are alike and while some make wonderful bed partners during an 8 to 12 hour session, others have sleeping habits that make them difficult to tolerate. 
I like a partner who can perform at least three times during the night but can also sleep restfully for a considerable stretch in between like I do. That way there is a nice balance of excitement and blissful rest. 
The ones I don’t enjoy are restless sleepers, who move around too much, have nightmares or talk in their sleep, sometimes with disturbing monologues. The kickers are the worst, who jolt you awake with their feet licking you. 
What has your experience been, both as clients and providers?

[pubic_assistance]

2 minutes ago, Luv2play said:

I like a partner who can perform at least three times during the night

[Luv2play]

To clarify, I think it is reasonable to have a play session early in the evening, then once during the middle of the night and then in the early morning before breakfast. 

Considering the expense of an overnight where the fee is more than triple compared to three one hour sessions and usually involves providing an expensive dinner and nice breakfast I think my expectations are reasonable. 

[pubic_assistance]

[+ KensingtonHomo]

1 hour ago, Luv2play said:

To clarify, I think it is reasonable to have a play session early in the evening, then once during the middle of the night and then in the early morning before breakfast. 

Considering the expense of an overnight where the fee is more than triple compared to three one hour sessions and usually involves providing an expensive dinner and nice breakfast I think my expectations are reasonable. 

I sleep with my husband and our dog every night. There's no room for anyone else. 

Plus I don't really want to have sex three times in twelve hours. And I'm not a great sleeper, so you'd not want to share a bed with me. 

[Luv2play]

3 minutes ago, KensingtonHomo said:

I sleep with my husband and our dog every night. There's no room for anyone else. 

Plus I don't really want to have sex three times in twelve hours. And I'm not a great sleeper, so you'd not want to share a bed with me. 

Agreed. I live alone so having an overnight is a treat. I’m also a good sleeper and have regular sleeping habits so the occasional night where sleep is disrupted by a good fucking is also welcomed. 

[+ Pensant]

I rarely do overnights anymore, but when I doA usually book two queen beds since I have a hard time sleeping with someone, although that isn’t the case with longer-term companions. Sex before bed and sex in the morning is all I need. If he wants to play during the night, I consider that an unexpected treat. 

[+ Jamie21]

If I hired for overnight it would definitely be separate beds!  Doing overnights for clients is not on my repertoire. 

[Simon Suraci]

I have a great time doing overnights, but only with regulars I know and trust. They wipe me out for the next day and it takes me a few days to recover my sleep schedule. Overnights with a new client are a huge gamble and I rarely do them. I charge a premium for a new client wanting an overnight. You have to click for these to work well. Mutual consideration and respect go a long way.

One of my regulars prefers overnights starting late at his hotel while he’s in town. In no particular order:

Therapeutic massage time on my table. Sometimes only 30 mins to work a problem spot. Sometimes an hour or two.

We fuck for about two hours straight. Yes, it’s true, we can go that long with only a few five minute breaks, and some flip flopping along the way. He loves bottoming so much that’s what we do for 90% of the fuck time. And to think… he used to be a strict top before he met me!

Often in the wee hours before we get to sleep: Lots of cuddle time, chatting, sharing. Golden Girls quoting. Kvetching. Kissing. Often leading to round two. Or one of us wakes the other up for round two. More cuddling. Spooning him to sleep.

Sleep time. Might only last 2-4 hours. With other clients, longer. He typically has to work, and I typically have some responsibility at home to attend to, so we get up in the early morning. After silencing my alarm, I suck his cock until his little head swells into a raging wood, and eventually his big head comes-to. Then it’s not long until I bring him to the edge and he explodes, satisfied, and lays peacefully resting as I take a shower and set out a small continental breakfast.

For other clients, we do more activities in the early evening, in addition to the above. Often dinner, some entertainment, drinks, other typical date stuff. It varies. I might sleep longer considering we do 1-2 rounds of sex before bed. Usually some form of sex in the morning. Everyone is different, and client moods and desires vary in the moment.

Overnights can be great with even the most terrible sleeping companions when you arrange for separate beds, or separate rooms. Say you have a suite in your hotel, or a guest room in your home. Snoring, thrashing, night terrors, whatever. It’s contained. What matters more is what you do before sleep time, and after you get up. And perhaps waking up to have a randy round in the night. Cuddling you can do before falling asleep, and switch beds or rooms before you do.

There are so many workarounds to enjoy the best aspects of overnights while mitigating the worst aspects. Sleep masks, earplugs, two blankets, etc. You can make it work. Planning, flexibility, and care for one another go a long way.

Some men are blessed. They’re great sleeping companions. For the rest of us with less than ideal sleeping habits, you find a way.

[Archangel]

Sleeping together is part of the BFE for me. The sex of course is important but it’s really the *experience* that includes all sorts of stuff. I like to think that I enjoy a guy’s time as an escort in the true sense of that word as much as I do a fucker. So yes – sleeping is important to me.

That said, I had one provider tell me I snore badly. So I’m sure that wasn’t pleasant for him… 😬 

[BuffaloKyle]

On 12/24/2024 at 9:59 AM, Jamie21 said:

If I hired for overnight it would definitely be separate beds! 

I have a queen bed but need my personal space at night. If I ever did an overnight, which would be a longshot anyway, it'd have to be in a king sized bed for sure.

[Luv2play]

29 minutes ago, Archangel said:

Sleeping together is part of the BFE for me. The sex of course is important but it’s really the *experience* that includes all sorts of stuff. I like to think that I enjoy a guy’s time as an escort in the true sense of that word as much as I do a fucker. So yes – sleeping is important to me.

That said, I had one provider tell me I snore badly. So I’m sure that wasn’t pleasant for him… 😬 

Yeah, snoring can be a nuisance. I snore the odd time but generally never when I’m sleeping with an escort. I do tell them before going to sleep to just turn me over if I start snoring. Or it that fails stuff their cock in my mouth. 

[Luv2play]

1 minute ago, BuffaloKyle said:

I have a queen bed but need my personal space at night. If I ever did an overnight, which would be a longshot anyway, it'd have to be in a king sized bed for sure.

I have two bedrooms each with a double bed. When I’m hosting, most escorts will sleep with me but the odd one will go to the other room to sleep. When they do that I will crawl into bed with them in the early morning, which is nice to get into a warm bed. 

[marylander1940]

On 12/23/2024 at 8:30 AM, Luv2play said:

To clarify, I think it is reasonable to have a play session early in the evening, then once during the middle of the night and then in the early morning before breakfast. 

Considering the expense of an overnight where the fee is more than triple compared to three one hour sessions and usually involves providing an expensive dinner and nice breakfast I think my expectations are reasonable. 

Do you want him to cum three times? 

Can you do it? 

Twice makes sense but having sex in the middle of the night whatever that means it's just not for everyone.

You're expectations are reasonable but one thing is having sex twice, 3 is a stretch.

[BuffaloKyle]

53 minutes ago, marylander1940 said:

Do you want him to cum three times? 

Can you do it? 

Twice makes sense but having sex in the middle of the night whatever that means it's just not for everyone.

You're expectations are reasonable but one thing is having sex twice, 3 is a stretch.

Again I've never done an overnight but I would think sex three times in an overnight would be something like sex upon arrival. Then you have a snack and watch a movie or something. Then sex again after that which could even include some shower play. Then sleeping and then morning sex. 

[Daniel84]

58 minutes ago, marylander1940 said:

Do you want him to cum three times? 

Can you do it? 

Twice makes sense but having sex in the middle of the night whatever that means it's just not for everyone.

You're expectations are reasonable but one thing is having sex twice, 3 is a stretch.

I agree, if I do an overnight, we usually have sex maybe twice. I once had an overnight that he wanted to fuck every other hour. I told him I’m not a battery powered dildo. Granted i can fuck for hours without getting off. 

[Daniel84]

4 minutes ago, BuffaloKyle said:

Again I've never done an overnight but I would think sex three times in an overnight would be something like sex upon arrival. Then you have a snack and watch a movie or something. Then sex again after that which could even include some shower play. Then sleeping and then morning sex. 

Once i am sleeping and if a client wakes me up i would be pissed off and moody lol. There’s a time in a place all my overnights have been extremely satisfied, but they know not to wake me up four in the morning to fuck. lol 

[BuffaloKyle]

Just now, Daniel84 said:

Once i am sleeping and if a client wakes me up i would be pissed off and moody lol. There’s a time in a place all my overnights have been extremely satisfied, but they know not to wake me up four in the morning to fuck. lol 

By morning sex not 4am for sure. Pitch dark outside is not morning yet.

[marylander1940]

7 hours ago, Daniel84 said:

I agree, if I do an overnight, we usually have sex maybe twice. I once had an overnight that he wanted to fuck every other hour. I told him I’m not a battery powered dildo. Granted i can fuck for hours without getting off. 

exactly, that was abusive and because of that many escort want to know the client's expectations before agreeing to having an overnight. 

7 hours ago, BuffaloKyle said:

Again I've never done an overnight but I would think sex three times in an overnight would be something like sex upon arrival. Then you have a snack and watch a movie or something. Then sex again after that which could even include some shower play. Then sleeping and then morning sex. 

That makes sense but not sex at 2 or 4 AM as implied by the OP. 

A snack? What about dinner? 

One more thing, many clients are overweight, and I've never met a fat person who doesn't snore. 

[Luv2play]

8 hours ago, marylander1940 said:

Do you want him to cum three times? 

Can you do it? 

Twice makes sense but having sex in the middle of the night whatever that means it's just not for everyone.

You're expectations are reasonable but one thing is having sex twice, 3 is a stretch.

It may be a stretch for some providers. I always ask in advance and select those providers for an overnight who are up for it. 
 

After all were talking about a sizeable fee which represents a week’s earnings to most folks. 

[marylander1940]

9 minutes ago, Luv2play said:

It may be a stretch for some providers. I always ask in advance and select those providers for an overnight who are up for it. 
 

After all were talking about a sizeable fee which represents a week’s earnings to most folks. 

I'm sure most would do it. I'm glad you're telling them they should up for 3 f... in a row.

Around what time is the 2nd time: 2, 4 AM? Midnight (after a recovery meal) like @BuffaloKyle says makes sense but not after falling asleep. 

What time do you wake them up if they have their own room?

Yes, but they can also earn the same amount having 2, 3 or 4 clients in a day. I know a local escort who goes to Richmond every month to see a client for 2 hours in the evening and 2 hours the next morning, same amount as an overnight but he gets to sleep by himself and have some "me time". 

Edited December 27, 2024 by marylander1940

[+ Pensant]

1 hour ago, marylander1940 said:

One more thing, many clients are overweight, and I've never met a fat person who doesn't snore. 

😂

[marylander1940]

10 hours ago, Daniel84 said:

Once i am sleeping and if a client wakes me up i would be pissed off and moody lol. There’s a time in a place all my overnights have been extremely satisfied, but they know not to wake me up four in the morning to fuck. lol 

common sense/good manners!

[Archangel]

12 hours ago, marylander1940 said:

Do you want him to cum three times? 

Can you do it? 

Twice makes sense but having sex in the middle of the night whatever that means it's just not for everyone.

You're expectations are reasonable but one thing is having sex twice, 3 is a stretch.

“Can you do brain surgery?”

I don’t pay just anyone to do something specialized that I could do myself. An escort can be expected to do things sexually that aren’t what are “typical.” In fact, that’s part of their offering – the extraordinary experience! Further, it wouldn’t be difficult to bottom three times…Depends what the arrangement is at the time of booking. If sex three times is a requirement and the escort can’t deliver, he should say so up front. There are going to be guys who can.

[marylander1940]

5 minutes ago, Archangel said:

“Can you do brain surgery?”

I don’t pay just anyone to do something specialized that I could do myself. An escort can be expected to do things sexually that aren’t what are “typical.” In fact, that’s part of their offering – the extraordinary experience! Further, it wouldn’t be difficult to bottom three times…Depends what the arrangement is at the time of booking. If sex three times is a requirement and the escort can’t deliver, he should say so up front. There are going to be guys who can.

Did you forget about having sex with people that are in 99% of cases he wouldn't be interested in....