Questions on Overnight Appointments

[hwic04]

I’ve hired providers for weekends before. Paid for their airfare to various resort cities at which I was staying, all meals and of course their fee for the weekend. Activities both in and out of the bedroom have always proceeded naturally with play time in the hotel room and enjoying the resort city together, sightseeing, dining, etc,. otherwise.

But I’ve never hired for an overnight, and have some questions. I’m considering hiring a provider local to the resort city I’ll be visiting. What typically are the hours I should expect the overnight to consist of? (I realize these can vary and will discuss with the provider beforehand.) But should I expect dinner to be part of the evening? If not, is the appointment then typically spent entirely in the hotel room? A roll in the hay followed by conversation? Then another go-around if desired? Middle of the night play? Again in the morning prior to the agreed time of departure?

If that’s the scenario it just seems so scripted (if that’s the right word) than the weekends I’ve described above as oceeding naturally.

Am I wrong about how I envision the overnight appointment? Am I missing something?

Really appreciate answers to these questions and hearing from experienced providers. Thanks.

[+ sam.fitzpatrick]

@hwic04, in my experience, overnight appointments are not much different than weekend appointments.  The difference is there's a little less time to get the know the guys you are spending time with.  In my overnights, they have usually included dinner.   They don't always include morning activities.  

I do think amount of play time will vary based on whether you are planning a week night or weeknd appointment.  Many guys with jobs outside of escorting may indicate they need x hours of sleep to be ready for the office the next day.

 

[Jarrod_Uncut]

Well it sounds scripted, but it’s always good to have a plan and understanding in mind. It doesn’t have to be verbatim, but you can switch it up as either pleases to. 

Edited June 24, 2021 by Jarrod_Uncut

[WolfCompanion]

The overnight hours really depend on the provider you are hiring. I have seen providers stating 8 hrs as considered overnight, etc. For me, an overnight start anytime in the evening and goes until the next morning. I am not a clock watcher. The dinner will depend on what time you two are meeting. If you are meeting before 8pm, I would check with your provider the dinner options. After 8pm, I always expect that my client has already had dinner. But anyway, I was talk to my client in advance to set expectations from both. About the fun time before, during and after bed time, there's no right answer to that. I am okay with all of them. Just make sure your provider has a good amount of sleep and check with him if he does have a regular job and what time he needs to be up the next day. I work for myself and remotely, so I never have the problem but it is always nice to check with them.

Please feel free to message me if you have any questions. I am new to this but trying to share the little knowledge and the stories I have heard from my clients.

[Bargara Leatherboy]

I have hired many times, normally for a couple of hours, sometimes those hours just flow into 3 or 4 or even 5.

I have always allowed the provider to call the shots on that, if i pay for 2 hours and they watch the  clock and wrap activities up around the 2 hours thats fine by me.  I have had experiences where the time I have paid for is cut short, and I would never make that a repeat visit.

I have had one overnight,  I was going to Asia, and contacted a highly regarded international escort initially for a few hours.

I sent a message via his contact details on his website, he responded lets chat which we did.

 

So in the course of an hours messenger call, he upsold me to an overnight,  based on value to me that would come from an overnight.

Logistically he could not provide an in call, where I was staying was 2 hours away, so he requested to be paid for travel time, or suggested that we do an overnight, in his locality if i found somewhere to stay.

Based on that the overnight made sense.

 

I found a one bedroom villa with pool, in an amazing setting, big bedroom 4 poster bed, outdoor and indoor bathroom, big terrace, outdoor kitchen.

He told me that during that time he expected to have 5 or 6 hours sleep.

So we settled on an overnight starting at 8pm, we would eat dinner, play, sleep and play again in the morning.

 

How it panned out, the venue was amazing,  he was running late, but kept me updated,  he arrived, we hugged and chatted.

We had talked about my interests and preferences, and I had done my research and knew he like scotch and cigars, so I had organised some great scotch and some awesome cigars.

we had a drink and chatted,  organised for dinner to be delivered, had some exploratory play,  dinner arrived, we ate, we moved onto a great play session, relaxed and romantic,  we got up, the night was warm, we sat out on the terrace, naked, drank scotch, smoked cigars, i love the smell of cigars, and I like to suck while he is smoking a cigar.

 

we ended up in bed again, played again, slept, woke up in the morning, had some play, he took a shower, we had coffee and chat and he left about 10am which is the 14 hours we had agreed on.

 

I think the success of the evening comes down to expectations and communications, it cost me with tip and accomodation $1600, I normally hire in Sydney for a couple of hours and pay $600, my last session was the two hours we paid for then we sat and drank green tea for about an hour afterwards.  

 

I dont think overnights would become my standard hire, but i have great memories of that night and if the circumstances were the same again I would repeat it

 

 

 

 

[italianboyph]

I think it all just depends on the agreement. In my experience with overnights, they us usually start sometime in the evening into the next morning/late am. 

[CalTec]

IMO, the longer the adventure, the more communication is required beforehand. @westernsydit sounds like you guys did the communication thing pretty well.  Would you have changed anything from that specific encounter?

I feel like one overnight packs in enough information about each other to have a good idea about moving forward with repeat encounters or calling it a one-off. Yes, it is a bit of a gamble if you're on the fence, but hey...meeting a stranger and staying the night is always an adventure in some way! 

 

[Bargara Leatherboy]

It was a great night, I have awesome memories of it, and if the circumstances were all in place to make it happen again, I would go with it.

I guess my one disappointment was that on his website he talks about kink and leather, but does not have any of that great gear with him in Asia where he lives permanently.

I knew that going into the appointment but if i were to improve on the evening, some leather bondage and discipline would have taken it from 5 star to 6 star for me

 

[Mo Mason]

You are basically paying someone $12oo - $18oo to sleep next to you.

SCORE for those of you who have a sleep fetish!

[+ tassojunior]

I've sometimes arranged a 1-hour date in the day followed by a 1-hour date that night, or a date at night followed by date in the morning. I pay for 2 dates not an overnight. They usually want to stay over and sleep at night or hang around and do dinner in the day. But between the sessions I don't really care if the guy  sleeps at my place, sleeps at his place, or sleeps on the curb.

I have had one provider tell me some overnights want, and he provides, sex all night long. If I could fuck for 8 hours I'd be a paid provider myself, not a client.  

Edited July 5, 2021 by tassojunior

[+ nycman]

For the most part I dislike overnights. 
There have been a few exceptions that were "worth it". 
Mostly in Europe where the overnight rates aren’t as ridiculous, 
and usually following a 1-2 hour hire that we both mutually decided to extend. 
 

Otherwise, it’s a hard pass for me. 

[Jamie21]

I think most overnights are more like having company and chatting etc than continuous sex. That’s been my experience of doing them.
I’ve  only ever done two as it’s not really my thing. The first one I did my client wanted sex before sleep but during the overnight he slept and just wanted to cuddle me and wake up next to someone. He specifically said not to wake him for sex during the night but he wanted to fuck me in the morning as I slept and I was to pretend to stay asleep as he fucked me. So I played along and ‘slept’ through the morning fuck. I was actually asleep when he must have started but by the time he’d finished I was pretending. Then he got up and ordered breakfast which we had in bed (I actually hate breakfast in bed so there was more acting!). After breakfast I left because he had a work meeting (the meet was in a hotel while my client was in London at a conference). So it was quite a relaxing session. 

The other one was for a regular massage client at his apartment. He had always previously visited me at my studio but his wife was away and he wanted me to visit him. He’d booked an evening massage and his apartment was a long way from my base so he asked if I wanted to stay overnight. I don’t have an overnight rate because it’s not something I normally do but it made sense for me to stay because I’d miss the last train so we agreed a rate and I stayed until morning. He was more active overnight lol so I didn’t actually get much sleep and I caught up on sleep on the train home. 

The last one I did was supposed to be an overnight, also in a hotel which my client had booked, but it didn’t work out. He was a young guy mid 20’s and had insisted he wanted an overnight for his first experience with a guy. He told me he had a girlfriend but he wasn’t sure what he wanted sexually. So in the end I agreed to an overnight at a hotel with him, which I booked because he didn’t want any bookings in his name. He’d talked about all the things he wanted to try (I should have guessed at this point that it was going to go wrong lol) and he’d asked that when he turns up at the room (he wanted to arrive separately) I be naked in bed for him. I should leave the room door unlocked for him to walk in and we go from there. So I’m naked in bed and my client walks in undresses and he joins me and it’s clear he’s over excited, he starts to fuck me and then cums after about 3 thrusts. Then he says he’s made a terrible mistake and he can’t stay. I ask him was anything wrong and he said no I’m cool but he has guilt about it and can’t stay. Fortunately he’d paid me (I requested payment up front given I was booking the hotel). I suggested we talk it through but he was so anxious he said sorry but he had to go. So I stayed the night on my own! 

[+ tassojunior]

7 hours ago, Jamie21 said:

I think most overnights are more like having company and chatting etc than continuous sex. That’s been my experience of doing them.

I think that's why often some very good earners on Chaterbate just leave their cams on for people to see them playing video games and maybe a comment or two to a random poster but never any sex besides a tease.. Therapy or company.

Maybe therapy is so expensive people hire escorts or tip cam models to listen to them. 

[Luv2play]

When I do an overnight I prefer the scripted approach, sex in the evening, in the middle of the night, and in the morning. It doesn't always happen though even when I make my desires known in arranging the date. 

The biggest problem I've encountered is providers showing up tired. So either one or two of the events don't occur. With those I don't do a repeat.

[HotWhiteThirties]

Overnights are my favorite with the right person. So far, I've never struck out. They sorta follow a pattern, but I tend to just let it flow, and have never been disappointed!