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wanderer
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Sorry if something similar is posted elsewhere, I did a search and couldn't find much. I am still a newbie at this and would appreciate any opinions.

 

I recently hired someone for an overnight (my first time doing such). I had a good time, but he fell asleep faster than I expected which was a little disappointing. I tried to make a few advances when I felt like he was waking up, and at the time, I was not sure if he was really that tired or ignoring me. I had planned to give a decent tip, but I was disappointed that I didn't have fun more than once. He looked a little disappointed that he didn't receive a tip (or that was his sleepy face, but I assume the lack of tip).

 

It sort of worked out because my plans changed later that day. I ended up meeting him again, got my fun, and used the tip money (plus a little more) for his hourly. I make a decent buck, but I am not rich (and far, far, far from it), so the extra money was an annoyance. And if I am paying for an overnight and then a hourly on top of it, I would rather pay more and just request a longer time slot or a weekend.

 

I also found out that he had another client after he left me that morning, so of course, I am leaning more towards being ignored so he "save up" for his next client. I can care less about how many people he sees (I know this is his business), but I had a private little w-t-f moment at the idea of being ignored on my dime for the benefit of someone else. This is speculation on my part.

 

 

When booking an overnight, is it okay to flat out state “I would like to do x, y, and z this many times” or is that too demanding/off putting? If they fall asleep, is it okay to wake them up before their time to leave?

 

Do I tell him that this disappointed me or just let it go and state expectations better next time? I don't want it to come across the wrong way. He met/exceeded all my expectations besides this. I had such a good time, I would hire him again, except my speculation makes me hesitant.

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Welcome @wanderer. Lots of stuff here is posted with common themes and questions. The old timers get a little grumpy about it, (WE had this thread five years ago!!)

But as a relative newbie myself I always appreciate a newbie's questions and reports of experiences. My first overnight ever was with a well reviewed escort with loads of positive feedback. He even had won the coveted EOY a few years back. I remember teasing him about the award, and having to go to a pageant with a swimsuit competitions and such. He was not amused. (I have an odd sense of humor.) Unfortunately he was also an escort I had never met. (The general recommendation around these parts is try to meet the escort well in advance of the proposed overnight at an hourly appointment.)

 

Your description of your overnight experience brought back memories of my own. The intimate parts were nice, but much briefer than I had hoped. Dinner together was awkward. We were having a hard time finding something to talk about and he seemed a little fussy. His drink was too strong and he didn't like his entree. It seemed to bother him that I stopped on the way back to the hotel to pick up a redbull. When we got back to the hotel, the fun was even briefer. Then we went right to sleep. On his side of the bed. As far away from me as he could get so (I thought) as not to have to touch me. And he snored mercilessly. Keep me up most of the night. Then the next morning there was little if any morning intimacy. He quickly got dressed as soon as he awoke....didn't even stop to take a shower, which I had specifically told him I wanted to enjoy with him. Didn't want breakfast. Seemed like all he wanted was to get the hell out of that hotel room as quickly as he could.

 

Of course the memories above are just half of the story. The way he experienced the overnight, how he tells it from his experience of the evening, is far different from the way I tell it. I know this because when he left he forgot to take home the gift that I had bought him as a memento of the evening. It was something of no value and I certainly didn't blame it for leaving it behind. But a little while after he left there was a knock on my door. There he was, smiling and inviting, really for the first time. It was like his personality had changed. He said he forgot his gift. Got a great hug and a kiss. I took this as a good sign and later told him what I thought about the evening. I invited him to tell me what was his perception of the overnight. Boy did he ever. I'm aware I can be somewhat standoffish, but Jeezlouise.......the things he had to say. In the end we both laughed at the situation and agreed to try again. I am forever grateful he forgot his gift that day. For I have had the pleasure of his company and his friendship for almost a decade. I'm embarrassed to confess how much I have spent seeing him over the years. But I haven't wasted a dime, ever. Cause there's nothing I'd rather do with my money than spend it on him.

 

What I learned was to never take an overnight with someone I don't know. And understand that this is a relationship, whether it lasts an hour, an evening, or a decade. And that there are two people in this relationship. And we both have to do our parts to make it work.

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It is going to depend on the escort, but my experience

with overnights has generally gone like this:

 

1. Verbal greetings/discussion/catching up (may last as long as half an hour)

2. Fooling around (another hour or so)

3. Dinner (the timing of which we could never plan; see above)

4. More fooling around (varying amounts of time)

5. Sleep/cuddling (also varies, but at least 5-6 hours on his part, less on mine because I have a hard time getting to sleep)

6. More fooling around (he was usually ready, willing and able to go longer than I was)

7. Departure

 

It's more a matter of what the guy you hire is like. Making demands is not likely to go over well, as escorts are not automatons and what happens depends on factors like chemistry, interests, etc. It might be better to ask an escort what happens on a typical overnight and to hire him for a shorter period before an overnight.

 

If the chemistry is there and you have hired someone who truly enjoys what he does, you are likely to have a better experience than you did.

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Welcome @wanderer. Lots of stuff here is posted with common themes and questions. The old timers get a little grumpy about it, (WE had this thread five years ago!!)

But as a relative newbie myself I always appreciate a newbie's questions and reports of experiences. My first overnight ever was with a well reviewed escort with loads of positive feedback. He even had won the coveted EOY a few years back. I remember teasing him about the award, and having to go to a pageant with a swimsuit competitions and such. He was not amused. (I have an odd sense of humor.) Unfortunately he was also an escort I had never met. (The general recommendation around these parts is try to meet the escort well in advance of the proposed overnight at an hourly appointment.)

 

Your description of your overnight experience brought back memories of my own. The intimate parts were nice, but much briefer than I had hoped. Dinner together was awkward. We were having a hard time finding something to talk about and he seemed a little fussy. His drink was too strong and he didn't like his entree. It seemed to bother him that I stopped on the way back to the hotel to pick up a redbull. When we got back to the hotel, the fun was even briefer. Then we went right to sleep. On his side of the bed. As far away from me as he could get so (I thought) as not to have to touch me. And he snored mercilessly. Keep me up most of the night. Then the next morning there was little if any morning intimacy. He quickly got dressed as soon as he awoke....didn't even stop to take a shower, which I had specifically told him I wanted to enjoy with him. Didn't want breakfast. Seemed like all he wanted was to get the hell out of that hotel room as quickly as he could.

 

Of course the memories above are just half of the story. The way he experienced the overnight, how he tells it from his experience of the evening, is far different from the way I tell it. I know this because when he left he forgot to take home the gift that I had bought him as a memento of the evening. It was something of no value and I certainly didn't blame it for leaving it behind. But a little while after he left there was a knock on my door. There he was, smiling and inviting, really for the first time. It was like his personality had changed. He said he forgot his gift. Got a great hug and a kiss. I took this as a good sign and later told him what I thought about the evening. I invited him to tell me what was his perception of the overnight. Boy did he ever. I'm aware I can be somewhat standoffish, but Jeezlouise.......the things he had to say. In the end we both laughed at the situation and agreed to try again. I am forever grateful he forgot his gift that day. For I have had the pleasure of his company and his friendship for almost a decade. I'm embarrassed to confess how much I have spent seeing him over the years. But I haven't wasted a dime, ever. Cause there's nothing I'd rather do with my money than spend it on him.

 

What I learned was to never take an overnight with someone I don't know. And understand that this is a relationship, whether it lasts an hour, an evening, or a decade. And that there are two people in this relationship. And we both have to do our parts to make it work.

 

Thanks, I asked him to give me any feedback in terms of technique, but I didn't really think of asking his perception of the night in general. It is a good idea. I think part of the problem was that I was brief in terms of what I wanted to do that night. I essentially just told him I wanted to meet at the hotel, do something/anything in the city per his recommendation, and then return to the hotel. I thought an overnight implied I wanted to do it more than once.

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It is going to depend on the escort, but my experience

with overnights has generally gone like this:

 

1. Verbal greetings/discussion/catching up (may last as long as half an hour)

2. Fooling around (another hour or so)

3. Dinner (the timing of which we could never plan; see above)

4. More fooling around (varying amounts of time)

5. Sleep/cuddling (also varies, but at least 5-6 hours on his part, less on mine because I have a hard time getting to sleep)

6. More fooling around (he was usually ready, willing and able to go longer than I was)

7. Departure

 

It's more a matter of what the guy you hire is like. Making demands is not likely to go over well, as escorts are not automatons and what happens depends on factors like chemistry, interests, etc. It might be better to ask an escort what happens on a typical overnight and to hire him for a shorter period before an overnight.

 

If the chemistry is there and you have hired someone who truly enjoys what he does, you are likely to have a better experience than you did.

 

This was my thoughts on what an overnight would be like, except the verbal greeting lasted about 5 minutes which threw me and the fooling around lasted I think close to 2 hours. I don't want it to seem like I am looking at him as a machine, but I also want to have a certain level of intimacy.

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I don't tip overnighters, and an overnighter that produces only one play session will not be repeated, much less tipped. If he's good for a romp, hire him for the quickie and save 5 0r 6 hundred bucks.

 

I wish it was that easy. I either have to fly to them or have them fly to me. I have to add all these costs and I view a new encounter as a risk. I don't know what I am getting, I would like to find a regular to not worry about what I am walking into/personality/etc,. It also takes me a while, so an hourly quickie is hard unless I am only focused on them. It makes overnight tempting cause it's only several hundred more with substantial more time -- and I do look for other things besides fun; I do enjoy talking / spending regular time.

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Sorry if something similar is posted elsewhere, I did a search and couldn't find much. I am still a newbie at this and would appreciate any opinions.

 

I recently hired someone for an overnight (my first time doing such). I had a good time, but he fell asleep faster than I expected which was a little disappointing. I tried to make a few advances when I felt like he was waking up, and at the time, I was not sure if he was really that tired or ignoring me. I had planned to give a decent tip, but I was disappointed that I didn't have fun more than once. He looked a little disappointed that he didn't receive a tip (or that was his sleepy face, but I assume the lack of tip).

 

It sort of worked out because my plans changed later that day. I ended up meeting him again, got my fun, and used the tip money (plus a little more) for his hourly. I make a decent buck, but I am not rich (and far, far, far from it), so the extra money was an annoyance. And if I am paying for an overnight and then a hourly on top of it, I would rather pay more and just request a longer time slot or a weekend.

 

I also found out that he had another client after he left me that morning, so of course, I am leaning more towards being ignored so he "save up" for his next client. I can care less about how many people he sees (I know this is his business), but I had a private little w-t-f moment at the idea of being ignored on my dime for the benefit of someone else. This is speculation on my part.

 

 

When booking an overnight, is it okay to flat out state “I would like to do x, y, and z this many times” or is that too demanding/off putting? If they fall asleep, is it okay to wake them up before their time to leave?

 

Do I tell him that this disappointed me or just let it go and state expectations better next time? I don't want it to come across the wrong way. He met/exceeded all my expectations besides this. I had such a good time, I would hire him again, except my speculation makes me hesitant.

 

There's a learning curve to hiring and you're simply learning, so it might be best to take responsibility here and refine your approach. As an escort, I really appreciate when someone tells me what their expectations or requests or preferences are before we meet. This way, I know what is expected of me and I can inform my guy if I don't think it's something I can do. If you don't tell someone what you want, you can't really fault them for not coming through. I would let it go and communicate clearly with him in the future. If he agrees and doesn't follow through and doesn't give a good explanation, then it's on him. Until you say something, it's on you.

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Welcome @wanderer. Lots of stuff here is posted with common themes and questions. The old timers get a little grumpy about it, (WE had this thread five years ago!!)

But as a relative newbie myself I always appreciate a newbie's questions and reports of experiences. My first overnight ever was with a well reviewed escort with loads of positive feedback. He even had won the coveted EOY a few years back. I remember teasing him about the award, and having to go to a pageant with a swimsuit competitions and such. He was not amused. (I have an odd sense of humor.) Unfortunately he was also an escort I had never met. (The general recommendation around these parts is try to meet the escort well in advance of the proposed overnight at an hourly appointment.)

 

Your description of your overnight experience brought back memories of my own. The intimate parts were nice, but much briefer than I had hoped. Dinner together was awkward. We were having a hard time finding something to talk about and he seemed a little fussy. His drink was too strong and he didn't like his entree. It seemed to bother him that I stopped on the way back to the hotel to pick up a redbull. When we got back to the hotel, the fun was even briefer. Then we went right to sleep. On his side of the bed. As far away from me as he could get so (I thought) as not to have to touch me. And he snored mercilessly. Keep me up most of the night. Then the next morning there was little if any morning intimacy. He quickly got dressed as soon as he awoke....didn't even stop to take a shower, which I had specifically told him I wanted to enjoy with him. Didn't want breakfast. Seemed like all he wanted was to get the hell out of that hotel room as quickly as he could.

 

Of course the memories above are just half of the story. The way he experienced the overnight, how he tells it from his experience of the evening, is far different from the way I tell it. I know this because when he left he forgot to take home the gift that I had bought him as a memento of the evening. It was something of no value and I certainly didn't blame it for leaving it behind. But a little while after he left there was a knock on my door. There he was, smiling and inviting, really for the first time. It was like his personality had changed. He said he forgot his gift. Got a great hug and a kiss. I took this as a good sign and later told him what I thought about the evening. I invited him to tell me what was his perception of the overnight. Boy did he ever. I'm aware I can be somewhat standoffish, but Jeezlouise.......the things he had to say. In the end we both laughed at the situation and agreed to try again. I am forever grateful he forgot his gift that day. For I have had the pleasure of his company and his friendship for almost a decade. I'm embarrassed to confess how much I have spent seeing him over the years. But I haven't wasted a dime, ever. Cause there's nothing I'd rather do with my money than spend it on him.

 

What I learned was to never take an overnight with someone I don't know. And understand that this is a relationship, whether it lasts an hour, an evening, or a decade. And that there are two people in this relationship. And we both have to do our parts to make it work.

Wow! Thank you, Becket! One to grow on for sure!

 

As far as overnights, I've outgrown them. Kudos to those who enjoy them. Im far too greedy. I do dailies with escorts. I rather spend 8-12 hours of daytime with an escort than splurge on hearing him snore or me holding in gas :D. A daily also gives him plenty of opportunity for an night date with someone else and time to recover after he cums 2-3x with me. I feel sorry for his night date, but that's not my problem. I also like dailies bc I sleep like angel that night...a warm glow and a smile on my face. Try them gents & ladies. It is worth taking the day off from work, plus blackout shades can make any bright day a very sexy dark night.

 

PS @wanderer, plenty of hotels offer daily rates at deep discounts.

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There's a learning curve to hiring and you're simply learning, so it might be best to take responsibility here and refine your approach. As an escort, I really appreciate when someone tells me what their expectations or requests or preferences are before we meet. This way, I know what is expected of me and I can inform my guy if I don't think it's something I can do. If you don't tell someone what you want, you can't really fault them for not coming through. I would let it go and communicate clearly with him in the future. If he agrees and doesn't follow through and doesn't give a good explanation, then it's on him. Until you say something, it's on you.

You don't ask?

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When booking an overnight, is it okay to flat out state “I would like to do x, y, and z this many times” or is that too demanding/off putting? If they fall asleep, is it okay to wake them up before their time to leave?

 

Do I tell him that this disappointed me or just let it go and state expectations better next time? I don't want it to come across the wrong way. He met/exceeded all my expectations besides this. I had such a good time, I would hire him again, except my speculation makes me hesitant.

 

Very sorry to hear of your IMO negative experience, @wanderer. I felt bad reading the account of your session. IMO and at the risk of sounding pretentious, the dude you hired is not keeping the faith with some of the better, reasonable expectations of what we do as escorts. For instance, as a fitness buff I like to make it proactively clear that I prefer a certain number of hours of rest when a client books me for an overnight. I have a problem with this guy sounding like he basically fell asleep on you when you had different expectations.

 

Having said that, @Eric Hassan makes some good points. I absolutely think you should "man up," "get over" thinking you're being demanding and say what's on your mind in terms of expectations when you hire an escort for an overnight. It's the way one presents those expectations that makes the difference.

 

Personally, if I had been that escort I'd like to think I'm perceptive enough to have sensed that you weren't happy. I would have at least had a conversation with you about how we could make it right during additional time together and either not charged you or asked for less than my usual hourly. You just spent perhaps low four figures on the overnight. I for one would be looking more to making sure you are happy and perhaps want to repeat than getting more money/an hourly rate out of you right then despite you're not being entirely happy with the night before.

 

I just did this this past weekend with a kinda spastic 20-something who was in town for the Emmys: I was his first hire ever and he was so nervous he was doing things that made it difficult for him to help me give him what he was paying me for. I ended up stopping the attempts at more explicit stuff, talking him down, giving him some pointers/feedback, letting him hang/relax/drink two more of the Stella Artois I bought for him in advance and spending an additional hour with him . . . during which he ended up shooting like a fire hydrant all over himself. Now I wanna see him again. LOL.

 

By all means, you should have expressed your disappointment to this guy (and if I were you, I would not have given him more money). Doing so would make him a better escort.

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...When booking an overnight, is it okay to flat out state “I would like to do x, y, and z this many times” or is that too demanding/off putting?...

 

It is okay to have a conversation about likes and wants whether you are booking for an hour, and evening, and overnight, or a weekend. I prefer to keep the conversation about finding out what we both like to do and can/cannot do rather than about delivering a list of expectations and requirements.

 

...If they fall asleep, is it okay to wake them up before their time to leave?...

...I had a good time, but he fell asleep faster than I expected which was a little disappointing. I tried to make a few advances when I felt like he was waking up...

 

This isn't me being a smartass, this is me asking a question because I am thoroughly confused: Are we talking about an escort who fell asleep at 8:30 PM or an escort who fell asleep at 11:00 or midnight? I'm asking because everyone has different sleep needs. If you were expecting to play all night and the escort started getting tired at 11:30, there seems to be a disconnect between what you wanted and what the escort could provide. Sometimes I don't get tired until well after midnight and other times I am drowsy at 9:00.

 

Just to level-set, my expectation of an overnight appointment is that we are both going to get a full night's sleep unless we both can stay up and play all night. The latter has never happened. I do not expect the escort to play all night.

 

...I also found out that he had another client after he left me that morning, so of course, I am leaning more towards being ignored so he "save up" for his next client. I can care less about how many people he sees (I know this is his business), but I had a private little w-t-f moment at the idea of being ignored on my dime for the benefit of someone else. This is speculation on my part....

It sounds like you are reading into the situation. My take is you were not being ignored. He was sleeping. We all do that every day.

 

...Do I tell him that this disappointed me or just let it go and state expectations better next time? I don't want it to come across the wrong way. He met/exceeded all my expectations besides this. I had such a good time, I would hire him again, except my speculation makes me hesitant.

You haven't stated your expectations to us, so it is hard to make a call on what you should do. Based on what you stated, it sounds like you expected to play with this escort for an entire night with little time for sleep. I find that to be unreasonable. Perhaps you would have been better served by someone who stays up late. I would have a more open conversation the next time you hire for an overnight. I would even suggest you follow @Truereview 's example and hire for a day and not an overnight.

 

May I provide a few do's and don'ts for you to ponder?

 

  1. Do openly communicate with your escort. Explain what you are looking for, ask questions, and be open to the answers.
  2. Don't provide a list of "expectations." You might hear that he simply cannot meet them. Instead, have a conversation about what you like, what he likes, and whether the two of you are in sync.
  3. Do ask about bedtime and morning time. If you are a night owl who sleeps until 9:00 AM and the escort goes to bed at 9:30 and rises at 5:00 AM you will NOT have a fun playdate.
  4. Don't hire a guy for an overnight without first hiring him for shorter appointments. That way, you will get a feel for whether the two of you are well-suited for longer play.
  5. Do focus on the playtime and not on what the escort does before or after your playtime. Unless, of course, he is planning a robbery or something, but that's a different issue.

Hope this helps.

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It is okay to have a conversation about likes and wants whether you are booking for an hour, and evening, and overnight, or a weekend. I prefer to keep the conversation about finding out what we both like to do and can/cannot do rather than about delivering a list of expectations and requirements.

 

 

May I provide a few do's and don'ts for you to ponder?

 

  1. Do openly communicate with your escort. Explain what you are looking for, ask questions, and be open to the answers.
  2. Don't provide a list of "expectations." You might hear that he simply cannot meet them. Instead, have a conversation about what you like, what he likes, and whether the two of you are in sync.
  3. Do ask about bedtime and morning time. If you are a night owl who sleeps until 9:00 AM and the escort goes to bed at 9:30 and rises at 5:00 AM you will NOT have a fun playdate.
  4. Don't hire a guy for an overnight without first hiring him for shorter appointments. That way, you will get a feel for whether the two of you are well-suited for longer play.
  5. Do focus on the playtime and not on what the escort does before or after your playtime. Unless, of course, he is planning a robbery or something, but that's a different issue.

Hope this helps.

 

What a brilliant response! I really liked the distinction between having a conversation about where your likes, etc. overlap vs offering up a list of expectations. The do and don't list is excellent - simple, easy, and a great way to help insure a great time!

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What a brilliant response! I really liked the distinction between having a conversation about where your likes, etc. overlap vs offering up a list of expectations. The do and don't list is excellent - simple, easy, and a great way to help insure a great time!

Thank you.

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This is exactly why I clearly explain on my site what to expect of an overnight. I'm usually in bed by 10, but during an overnight I push that to 11 or midnight, so there is time for dinner and/or a show and a few hours of naked time. I definitely think that some mornin' lovin' is one of the best parts of an overnight, as long as the guy is up for it.

 

After some lovin' I usually make breakfast while he is showering, if we are at my place. If at a hotel, shower before heading out to breakfast or room service. I don't usually plan to finish an overnight until around 10 am the next morning unless the client has to be somewhere early.

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It is going to depend on the escort, but my experience

with overnights has generally gone like this:

 

1. Verbal greetings/discussion/catching up (may last as long as half an hour)

2. Fooling around (another hour or so)

3. Dinner (the timing of which we could never plan; see above)

4. More fooling around (varying amounts of time)

5. Sleep/cuddling (also varies, but at least 5-6 hours on his part, less on mine because I have a hard time getting to sleep)

6. More fooling around (he was usually ready, willing and able to go longer than I was)

7. Departure

 

It's more a matter of what the guy you hire is like. Making demands is not likely to go over well, as escorts are not automatons and what happens depends on factors like chemistry, interests, etc. It might be better to ask an escort what happens on a typical overnight and to hire him for a shorter period before an overnight.

 

If the chemistry is there and you have hired someone who truly enjoys what he does, you are likely to have a better experience than you did.

 

Sounds like you have a great formula and a great guy to go with it!

 

My preference is to suggest that the overnight is fine but could we start at 3 in the afternoon and end around 11-12 - that gives plenty of time for play - intimacy - chat - more play - dinner - more play - drinks - more play - Night Sweetie!!!

 

I do not sleep well in general and even less so with relative strangers - even with my regular buddy sleeping together is difficult

he is a light sleeper - I toss and turn - and after spooning till he is softly snoring - Im off to my side of the bed . . .

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There's a learning curve to hiring and you're simply learning, so it might be best to take responsibility here and refine your approach. As an escort, I really appreciate when someone tells me what their expectations or requests or preferences are before we meet. This way, I know what is expected of me and I can inform my guy if I don't think it's something I can do. If you don't tell someone what you want, you can't really fault them for not coming through. I would let it go and communicate clearly with him in the future. If he agrees and doesn't follow through and doesn't give a good explanation, then it's on him. Until you say something, it's on you.

 

Thanks for the input. I felt like if I e-mailed too much information it would be off putting. I just didn't anticipate this situation – I thought we would discuss things as they go. When I say he fell asleep, I mean he laid down, passed out, and was snoring up a storm in like 2 minutes – literally. I am actually sort of jealous of his ability to fall asleep so easily. When this happened, I lost that opportunity and then I just didn't know what to do or what was appropriate. I honestly assumed (and it was wrong of me) that when people pay for an overnight, there was going to be fun more than once.

 

 

 

Very sorry to hear of your IMO negative experience, @wanderer. I felt bad reading the account of your session. IMO and at the risk of sounding pretentious, the dude you hired is not keeping the faith with some of the better, reasonable expectations of what we do as escorts. For instance, as a fitness buff I like to make it proactively clear that I prefer a certain number of hours of rest when a client books me for an overnight. I have a problem with this guy sounding like he basically fell asleep on you when you had different expectations. . .

 

Personally, if I had been that escort I'd like to think I'm perceptive enough to have sensed that you weren't happy. I would have at least had a conversation with you about how we could make it right during additional time together and either not charged you or asked for less than my usual hourly. You just spent perhaps low four figures on the overnight. I for one would be looking more to making sure you are happy and perhaps want to repeat than getting more money/an hourly rate out of you right then despite you're not being entirely happy with the night before. . .

 

By all means, you should have expressed your disappointment to this guy (and if I were you, I would not have given him more money). Doing so would make him a better escort.

 

Such an offer from anyone would be highly appreciated, but I don't think I could ever accept it due to the nature of the work.

 

I want to clarify that I don't view it as a negative experience; like I said, he met all my expectations/wishes/wants/needs except for this one. I had good time. I really just wanted someone to chill with me, try things, and help me feel more comfortable with guys. I just felt disappointed that the trial period/aspect essentially ended earlier than expected and was confused about what to do.

 

I tried to give him the benefit of the doubt by doing the hourly. I wanted a little something more before I had to catch a flight, especially since I tend to stay in awful places for work for month at a time. I thought of going with someone else, but it seemed more complicated since I had limited time. Then the more I thought about it, the crappier I felt as I didn't know if I was purposefully being ignored or not. I tend to dwell on shit. It was a good experience overall, just how it ended put a dent in it.

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I agree. I'm a light sleeper anyway, and rarely sleep well in hotel rooms in general. Plus, I would rather pay for a day together doing whatever, vs pay to have you sleep next to me for x amount of hours. I could be in the minority, but that seems like a waste imo.

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It is okay to have a conversation about likes and wants whether you are booking for an hour, and evening, and overnight, or a weekend. I prefer to keep the conversation about finding out what we both like to do and can/cannot do rather than about delivering a list of expectations and requirements.

 

This isn't me being a smartass, this is me asking a question because I am thoroughly confused: Are we talking about an escort who fell asleep at 8:30 PM or an escort who fell asleep at 11:00 or midnight? I'm asking because everyone has different sleep needs. If you were expecting to play all night and the escort started getting tired at 11:30, there seems to be a disconnect between what you wanted and what the escort could provide. Sometimes I don't get tired until well after midnight and other times I am drowsy at 9:00.

 

Just to level-set, my expectation of an overnight appointment is that we are both going to get a full night's sleep unless we both can stay up and play all night. The latter has never happened. I do not expect the escort to play all night.

 

It sounds like you are reading into the situation. My take is you were not being ignored. He was sleeping. We all do that every day.

 

You haven't stated your expectations to us, so it is hard to make a call on what you should do. Based on what you stated, it sounds like you expected to play with this escort for an entire night with little time for sleep. I find that to be unreasonable. Perhaps you would have been better served by someone who stays up late. I would have a more open conversation the next time you hire for an overnight. I would even suggest you follow @Truereview 's example and hire for a day and not an overnight.

 

I met him at 11pm. When I meet someone that late with the discussed plan to go out/do something, I understand, and assume they understand, it is not going to be an early night. My only real expectation for the session was fun at the hotel more than once. I wanted to try different things, but I don't view these things as anything crazy and if he would of told me “let's stay with x and y and forget about z” that would have been fine. The entirety of the experience of things was more important to me than all the details.

 

May I provide a few do's and don'ts for you to ponder?

 

  1. Do openly communicate with your escort. Explain what you are looking for, ask questions, and be open to the answers.
  2. Don't provide a list of "expectations." You might hear that he simply cannot meet them. Instead, have a conversation about what you like, what he likes, and whether the two of you are in sync.
  3. Do ask about bedtime and morning time. If you are a night owl who sleeps until 9:00 AM and the escort goes to bed at 9:30 and rises at 5:00 AM you will NOT have a fun playdate.
  4. Don't hire a guy for an overnight without first hiring him for shorter appointments. That way, you will get a feel for whether the two of you are well-suited for longer play.
  5. Do focus on the playtime and not on what the escort does before or after your playtime. Unless, of course, he is planning a robbery or something, but that's a different issue.

Hope this helps.

 

I obviously wouldn't e-mail someone and be like “I expect...,” I would phrase it better than that, such as “I really would like... would this be possible?” At the end of the day, though, for me, it is still setting expectations for one another in order for a meet to work. I apologize for the connotation/word usage, I was trying to be concise for the posting. I appreciate the do and don't list.

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I've had a couple of overnights now, and if nothing else happens in the 'silent hours' the touch, occasional slight rousing, and cuddling can be wonderful. If you both retreat to your respective sides of the bed, not so much. I have had my companion wake up during the night and fuck me gently, it all depends on you, who he is and how he wants to play things. Also, think about the rates you are paying, I doubt the overnight fee is more than what it would cost for a few hours in the evening and a couple of hours in the morning. In any case, sharing your bed with a hot man is worth something.

 

Clearly you have to make sure that you and your companion are compatible. @Lance_Navarro's description of an overnight, with social and other interaction in the evening, sleeping together, a pleasant awakening then breakfast is delightful. To my mind, lamenting that you are paying for your, and his, sleep time misses the point.

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I met him at 11pm. When I meet someone that late with the discussed plan to go out/do something, I understand, and assume they understand, it is not going to be an early night. My only real expectation for the session was fun at the hotel more than once. I wanted to try different things, but I don't view these things as anything crazy and if he would of told me “let's stay with x and y and forget about z” that would have been fine. The entirety of the experience of things was more important to me than all the details.

 

 

 

I obviously wouldn't e-mail someone and be like “I expect...,” I would phrase it better than that, such as “I really would like... would this be possible?” At the end of the day, though, for me, it is still setting expectations for one another in order for a meet to work. I apologize for the connotation/word usage, I was trying to be concise for the posting. I appreciate the do and don't list.

 

If I started an overnight at 11, I would definitely be ready for bed within an hour or two, but that's why I would never take an overnight starting at 11. My overnight usually start around 7 if dinner is part of the evening or 8ish if not.

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I've had a couple of overnights now, and if nothing else happens in the 'silent hours' the touch, occasional slight rousing, and cuddling can be wonderful. If you both retreat to your respective sides of the bed, not so much. I have had my companion wake up during the night and fuck me gently, it all depends on you, who he is and how he wants to play things. Also, think about the rates you are paying, I doubt the overnight fee is more than what it would cost for a few hours in the evening and a couple of hours in the morning. In any case, sharing your bed with a hot man is worth something.

 

Clearly you have to make sure that you and your companion are compatible. @Lance_Navarro's description of an overnight, with social and other interaction in the evening, sleeping together, a pleasant awakening then breakfast is delightful. To my mind, lamenting that you are paying for your, and his, sleep time misses the point.

I haven't had an overnight companion in 20 years. An overnight might satisfy this void.

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