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Questions about overnights


Reluctant Daddy
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I've been kicking around hiring for an overnight session. Other than the obvious, dinner and sleep, what do most others do? How much of the obvious should be expected or anticipated? Generally what hours are considered overnight?

 

I've previously hired this guy for a couple one hour sessions, and given the time during those sessions, it was essentially pleasant small talk getting to know just a little bit about one another. I don't know that much about him, or him that much about me to make the evening interesting for him. I don't want The evening to be filled with awkward silence, punctuated with "sooooo"s. I'm much older then him and not sure that we would have enough in common.

 

I'd like to be be a fun experience for both of us.

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Once again I stress this, you are hiring this man. He is working for you. This is play for you, work for him. Like going to a ballgame and playing catch with one of the players before the game. Fun for you, work for him.

So, in that regard, be a good host. Allow him to do his job well. Pick a restaurant you like but only after asking about his preferences. See what matches and go there. You may need to initiate sexual activity. I used to be a three times in an overnight guy, but lately, those wake and fuck sessions in the morning are just not as much of a necessity for me as they once were. When they were, I would have to start because the escort usually would prefer beauty sleep. If he doesn't need to be prodded, so much he better. So..... I usually try to get something in before dinner, I like to get something in after dinner. The morning is a sleep late, quick breakfast, thank you for your kind attentions and an adios amigo.

Conversations are a two way street, but one thing that people love to talk about is themselves. So if you are lost for conversation, ask him about his hometown, his work out routine, when it was that he knew he had a massive schlong, You know, dinner conversation.

 

General topics to avoid in my opinion: 1 Number of clients that day, that week, that trip, that lifetime. Just assume it is a lot more than you have had and move on. 2 Finances Yours are none of his business and his are none of yours. Keep the financial discussion to the exchange for services for payment 3 Politics If you are hiring Stephen Kessler, you may have to stay up all night trying to convince him of the errors of his ways, and you will not do it. But for anyone else, politics never leads to bonding. You may both love Ronald Reagan but one may love him for his policies and the other for his movies. Both of you are wrong, but there is no sense dragging a long dead President into the conversation, unless it is time for payment.

 

Good luck. Overnights are fun. They are a sexy pajama party without the pajamas. Remember though, the best way for you to end up thinking that it was a sexy evening is to make sure that he knows that is what you want and you make sure that you get it. Also, ask him to bring his own chocolate eclairs. If you have to ask why, you are not using your imagination enough.

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Great advice from PK.

 

It really depends on your chemistry together.

 

But all of my overnights have had a little less sleep than fun, plus some social time (dinner, shopping, and/or gym time together). Maybe 45%/40%/15% fun/sleep/social. Although I have had one that went more like 70/20/10. ;)

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Great advice from PK.

 

It really depends on your chemistry together.

 

But all of my overnights have had a little less sleep than fun, plus some social time (dinner, shopping, and/or gym time together). Maybe 45%/40%/15% fun/sleep/social. Although I have had one that went more like 70/20/10. ;)

Wm you sexual animal you , 70% fun on a 12 hour overnight is 8.4 hours of play time. That is just about my yearly quota. Of course, I suggest that you can include meals in the sexy time, should you be so inclined. "Our dessert buffet will be served on Tristan Baldwin's rock hard abs. Feel free to lick your fingers, his fingers and anything else you want to lick."

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Wm you sexual animal you , 70% fun on a 12 hour overnight is 8.5 hours of sexy time. That is just about my yearly quota. Of course, I suggest that you can include meals in the sexy time, should you be so inclined. "Our dessert buffet will be served on Tristan Baldwin's rock hard abs. Feel free to lick your fingers, his fingers and anything else you want to lick."

Yeah--that was a 22 hour overnight. Started at 7 pm and we went to sleep around 8 am. We both brought snacks, so some of the food time was just a few seconds and, as you as astutely surmised, mostly overlapped with the fun time. Though we did go to an actual restaurant for a late lunch. Eventually.

 

Needless to say, that is not my norm. It is fueled by very intense chemistry.

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Yeah--that was a 22 hour overnight. Started at 7 pm and we went to sleep around 8 am. We both brought snacks, so some of the food time was just a few seconds and, as you as astutely surmised, mostly overlapped with the fun time. Though we did go to an actual restaurant for a late lunch. Eventually.

 

Needless to say, that is not my norm. It is fueled by very intense chemistry.

I haven't had that much chemistry since high school.

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At bedtime +2hrs, I get up to go pee, pat him on the butt and I climb back into bed and snuggle up and go to sleep.

 

At bedtime +5hrs, I get up go pee, think about patting him on the butt, then I climb back into bed and go back to sleep.

 

At bedtime +7hrs, I get up to go pee, fall back into bed and go back to sleep.

 

At bedtime +9hrs, I get up, stay up, and don't get any more sleep.

 

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I've been kicking around hiring for an overnight session. Other than the obvious, dinner and sleep, what do most others do? How much of the obvious should be expected or anticipated? Generally what hours are considered overnight?

 

I've previously hired this guy for a couple one hour sessions, and given the time during those sessions, it was essentially pleasant small talk getting to know just a little bit about one another. I don't know that much about him, or him that much about me to make the evening interesting for him. I don't want The evening to be filled with awkward silence, punctuated with "sooooo"s. I'm much older then him and not sure that we would have enough in common.

 

I'd like to be be a fun experience for both of us.

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I've been kicking around hiring for an overnight session. Other than the obvious, dinner and sleep, what do most others do? How much of the obvious should be expected or anticipated? Generally what hours are considered overnight?

 

I've previously hired this guy for a couple one hour sessions, and given the time during those sessions, it was essentially pleasant small talk getting to know just a little bit about one another. I don't know that much about him, or him that much about me to make the evening interesting for him. I don't want The evening to be filled with awkward silence, punctuated with "sooooo"s. I'm much older then him and not sure that we would have enough in common.

 

I'd like to be be a fun experience for both of us.

 

I like to build up to the overnight if at all possible to assure a mutually enjoyable time. You might consider an evening appointment as the next step....dinner and play for 3 or 4 hours....if it makes sense (sometimes the added cost of the overnight just doesn't make sense to just do the evening appointment). What I try to do is give an outline of what is enjoyable for me, which usually includes a very nice dinner, some relaxing time afterwards to watch a movie and then play before bed. I like early dinners so I try to make sure he is fine with that. Usually the escort is more than happy with whatever suggestions I make. Communicating in advance the ideas for the meeting, expectations and likes/dislikes will help make things go smoothly, in most cases.

 

I just had a very enjoyable overnight last night after meeting the guy for a dinner appointment a few weeks ago. He is an excellent conversationalist so that made it very easy to determine the type of overnight we would have. I understand very well the types of foods he really enjoys so I was able to make some suggestions for our dinner. I also found out he really enjoyed wine and cheese so I made sure that was on hand afterwards while we watched some TV. He is really interested in politics (his first time voting for the President) so we watched quite a bit of the cable news on the voting in SC and Nevada. While I fully understand that he is working for me, I just find it easier to identify things that are mutually enjoyable and set things up to focus on those so it enhances the appointment. Again, it's all about communications and planning things out in advance as much as possible.

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Overnights are not for the faint of heart. Unless one party has to fly to the other, my personal opinion is that they aren't worth all the communicating and planning that is required. I would much rather hire the guy for a couple of long appointments. They are so much more straightforward.

 

If you do proceed, you've got good advice above. I'd especially pay attention to the part where you might have to initiate the fun time or be very explicit in the planning. Before dinner, after dinner, two times, three times? It gets grey in an overnight and you can't expect your companion to take the lead.

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90% of the times I hire it is for at least an overnight. PK's recommendations are spot on.

 

The other thing to anticipate and not be startled by is needing to allow the escort some personal time to check his email/voice mail to respond to other clients. He won't need hours to do this, but a few minutes of personal time is reasonable. He may also need to check in on the pet sitter or make a nightly call to a sick family member.

(Many times, he will take care of these things while I freshen up.)

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If he's good, he'll make it work. Period. I mean 'full stop'. Research. You've met him for short appointments so you know whether you hit it off with him. If he has reviews of overnights that will help you. If his pitch talks about cuddling, getting to know his clients, liking to go to sleep holding hands or spooning, it would be a good sign. Although if you want him to pound you for eight hours maybe not. Only you can know whether the age difference might make things a little awkward.

 

I've mentioned my vast experience in this field and that one meeting was my first meeting with the guy. We met at 7pm, dinner for a couple of hours, hotel room fooling around for maybe three, sleep for seven, arms and legs intertwined (so definitely not 'wasted time' as is sometimes said of paying someone to be asleep with you), wake up, play around, shower then breakfast. All over by a little after 9am. The whole time flowed seamlessly, no awkward pauses, nothing felt rushed, if he was ever bored it never showed, and we exchanged emails afterwards saying we had enjoyed each other's company.

 

Sure, you are paying him to be there, but if it's a BFE you are buying, part of that is you contributing fully not just relying on him to make it happen.

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Since no one else has mentioned this in detail: What constitutes an overnight depends on the escort, but generally it's an at least twelve-hour period. Check. If it's less than that, consider that this might not be the escort's forte. If it's more than that, so much the better. Other than that, the timing is up to the two of you.

 

Most of my hires have been overnights. Usually we chat and connect first, go out to dinner, do some more chatting and connecting (this can go pretty late), cuddle and go to sleep, and often connect once more in the morning. We have never managed to make it to breakfast once. Even during a twenty-four hour appointment, it was after eleven am before we went out to find food.

 

I second the idea of a longer evening appointment first to see if the two of you can sustain a dinner conversation unless it's so close in price to the overnight not to make economic sense.

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What a knowledgeable post! +1 for me.

 

Many of us work differently, many alike all to achieve the same goal-- in hopes of a very satisfied new regular. It's great to explore new things. Espically when it benefits the body, and gives you ample matieral to think about later ;)

 

My favorite thing is a sugar scrub shower, it gives us closeness in a smaller area, plus I do all the work, you just stand there and watch ;) the sugar is mixed with essetial igrediants to ensure the dead skin is removed and a fresh, soft new skin is left. Great for everyone, even sensitive skins such as myself. That's the one down fall of being blonde and blue eyed.

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We have never managed to make it to breakfast once.

Breakfast wasn't part of the original agreement. After the shower (the pre-agreed end point) we discussed and agreed on breakfast ['I'll think about breakfast if I like the client']. He drove us there and drove me back to the hotel, I paid.

What constitutes an overnight depends on the escort,

I've seen 'overnights' defined as 7 hours (midnight to 7am, ffs?) to 6pm to 11am. Ask him what it means! Good guys are flexible.

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FWIW here's my view based on my own experience. If, apart from the obvious physical activity, all you've had so far is "essentially pleasant small talk" I suggest you do NOT hire for an overnight date. Rather you should next have an extended date of several hours once you have decided what it is exactly that you would like to enjoy in that extended hiring.

 

In the past, I've invited guys to an art exhibition, the theatre, major sports events. One guy suggested I work out with him. After those shared experiences, I invited the guys to dinner or lunch. I was younger then but I was careful to specify when I expected us to play together. Now that I'm older, I very much prefer to get physical in the bedroom first - it's good cardio for me - and then go out for an excellent dinner. Bottoms have told me they appreciate the 'reverse-date'. I can say that 12-15 years ago, I did many more overnight dates.

 

What you say resonates particularly with me because of overnight dates with two guys I'd dated several times beforehand. The first was with Jack, a 24 year old goodlooking muscleboy with probably the finest ripped physique I've seen, while the second was with Enzo, a very handsome preppy 23 year old Italian-Brazilian who was passionate and did everything. Jack was a voracious bottom and greedy cocksucker: he pleasured me before dinner at home, after dinner and once during the night, before finishing me off before breakfast and truly by then I was drained and spent. Jack had, however, zero conversational skills so dinner had been a little awkward. Enzo was always very chatty and keen to spend time with me: he arrived beautifully-dressed and we had great fun in bed together before we went to dinner in a very smart restaurant, where suddenly he had little to say and was unanimated. We cut dinner short and came home but he was lacklustre (he blamed it on over-work earlier in the week) and he was very apologetic when I drove him home in the morning. Nowadays, on an overnight date, I like to sleep well for 7 hours or so but I delight in being woken in the morning by a good blowjob. I have zero interest in sex during the night.

 

I mention all this to bring home to you that a guy can be great for an hour or two, but it's a very different skill-set to entertain a client for the 12 hours or so that constitute an overnight date. If you are determined to have a guy stay overnight, be very clear on what you desire and how often/when you want your desires met.

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