Carman Fox

Overnights

Mike_Hunt

Active member
Nov 23, 2008
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A fellow Perbster (Perbite?) sent me an email asking for tips for one of my favourite ways to spend time with an escort - overnights. I think there have been a few posts on this topic, but I will add a few of my own thoughts and experiences and see if there is interest in further discussion. My own approach is to treat an overnight with the same attitude I would if this were a "real" relationship - that is with great respect for boundaries, and a focus on mutual pleasure. I get much more enjoyment when I can show a gorgeous woman a pleasurable time, both sexually and personally.

I have two types of overnights - "dinner date" overnights, and regular overnights.

I have one or two special women that I will start an overnight earlier in the evening, maybe 6pm, so we can have round one of sex before going out for dinner together. Having sex first works well because we are both pretty horny and it is fun to work up an appetite. Usually for a dinner date overnight, I am visiting out of town so there is little likelihood of running into friends or acquaintances, but we will have some sort of cover story just in case. I only do the dinner date overnights with escorts that I have seen before and have a good connection, and interesting things to talk about. As dinner is winding down, our conversation might shift to some whispered suggestions of what we will be doing next. One of my ATFs is very good at generating creative ideas, and it is fun to discuss while she rubs my thigh under the table. Back to the hotel for round 2, usually drawn out over 2-3 hours. We usually share a glass of wine or two, but not to the point of getting intoxicated. Depending on the time, after round 2 we might have a shower together and then watch some Netflix - usually something that doesn't require much attention like some stand-up comedy show. Then lights out and snuggling to fall asleep. We will already have discussed sleep requirements and preferences. Most women will want at least 7 hours sleep time, and request limited body contact during that time. We might agree that my arm lightly on her shoulder would be okay, but not on tits or pussy. Most overnights will end at around 8 or 9 am, so hopefully she wakes up at around 7 am. We might snuggle for a bit and stroke pussy/dick. Before getting into business, we take turns going for a pee and brushing teeth. Morning sex is usually a bit shorter, maybe 45 minutes or so. Then she gets up and showers while I doze in bed. She comes back for a goodbye hug and kiss.

The regular overnight usually starts at 9pm and is much the same as above without the dinner portion. I do these with escorts that I might not have the same personal connection with, and there is a lot less time for conversation - just 2 or 3 hours of intense fucking before sleeping, and then another round in the morning.

The rate for overnights is hugely variable. Some women charge up to $4k for 12 hours. I have never done this, and I wonder if that is for younger guys who can MSOG all night long. I am seeing escorts who will charge $1500-$2000 range, and expect and need sleep time (as do I).

Any other comments or suggestions?
Mike
 

RobBC

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Oct 27, 2002
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Thanks for writing all this up, very insightful.

I've never done an overnight myself, so maybe a question I'd ask those who have is: if you were to be booking a overnight with someone, what questions should you ask beforehand? Like you mentioned in that post coming up with a cover story, and setting expectations around sleep, anything else that should get figured out beforehand?
 

Mike_Hunt

Active member
Nov 23, 2008
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There are endless possibilities with a longer time together.
Get creative and explore new territory.
Some women will offer to play out a fantasy, or be willing to try out something you suggest. The sexy secretary is always good fun.
I will usually ask for some specific lingerie. I am in a rut, and always prefer sheer black stockings, garter, and a certain type of high heel.
Ask what sort of beverage she would like. I have one lady who likes to explore different locally produced liquors.
Of course chocolates or some other treats are always good. Then there is the "where did I hide the chocolate game"
If there is a jacuzzi in the hotel room, then there are even more possibilities. Another lady I see likes to do skin treatments with some special products she brings along.
Maybe a bit of kink if she is into it.
Mostly, have fun!
Mike
 

Mike_Hunt

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Nov 23, 2008
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Yes, connection and compatibility is key.
For long sessions of playing, I think pleasuring her is very important. I want someone who really enjoys sex, has good orgasms and has a nice pussy to eat. Usually, it is almost 50:50 as to who is pleasuring who (whom?).
Asking her to bring along toys she likes is always good. Then you can play who can swallow the dildo deeper. I always lose though.
Also make sure you have agreed under what conditions she will untie you in the morning so the hotel housekeeping staff don't have to .
 

PuntMeister

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Jul 13, 2003
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Great advice Mike. I was nodding my head as I read your threads while fondly remembering my overnighters.

Just want to add a few thoughts on this.

First, I would say don’t go for an overnighter too quickly. Build up to it with dinner & dessert dates, longer evening sessions, hanging out casually together, and discovering common passions, world views, and life purposes as you would with a real GF. Develop the “F” in GF. Also, dont’t expext that sexual tension to last all night long, more like a cozy togetherness where you are both relaxed but not alone. The evening goes kind of like “GGGG-FFF-FFFFFFFFFFF-GG-F”

It helps to have a mindset that this is not a one-time-thing, even if infrequent. My first overnight was actually in separate rooms at an sp’s incall (me in the playroom and her in the bedroom). That progressed over time to the point where there is no way now she’d let me sleep alone even if I wanted too. The natural escalation was a great journey in itself. Patience.

Things went well with an overnight session whenever I felt fortunate and grateful for what was, and didn’t dwell on what wasn’t. To that end, it has been constructive to decide/agree in advance who’s deciding where we go for dinner, and taking the lead on ummmmm GGG things. Sometimes I will express a hankering for a favourite ethnic cuisine, sometimes I will say I really want to take you xxxxxx, sometimes “Your call on dinner tonight babe”, and then totally go with the flow. Likewise, I either express a theme in advance for the evening (general vibe or specific roleplay, but never scripted), or simply leave it to her to take the lead in whatever way she sees fit. This clarity has worked out really really well.

Lastly, I would say the texts / convo’s before and after are part of the experience for both of us. We express that we get stoked in anticipation of the big date, and we exchsnge warm thoughts for a day or two afterwards.

Anyways, that’s my feeling on overnighters. Hope that helps if you’re considering these extended sessions.
 
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cr_tallguy

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Aug 9, 2015
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Campbell River
I agree 100% with the idea of spending long periods of time with a lady first and getting to know her well before booking an overnight. In my experience it makes the overnight go very smoothly.
 
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Andrew69913

How do you guys actually fall asleep during overnights? lol Even when I am in a new relationship, it takes me awhile to actually be able to sleep with someone else in the bed, which usually results in a couple weeks of no sleep for me while she's snoring away, dreaming about puppies or whatever. I really liked Punt's scenario with the separate sleeping rooms, that would be cool to start. It kind of sucks because I DO really love snuggling lol. I don't think I would have a difficult time with conversation or anything as I'm a naturally inquisitive person who likes talking. So much so, we sometimes almost run out of time to do the deed during a 1hr or 2 hr appointment lol (no I have never been denied sex due to this). Anyway, yeah, I can see the point that you want to establish some sort of familiarity before indulging in an overnight stay, on the other hand there is only one way you can become comfortable in these situations, and that's by doing them. Can't start a fire without a spark, even if you're just dancing in the dark.
 
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ExpCharlee

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I miss overnights, I feel like I used to get more than I do now—for covid reasons I think (a lot of mine were trips). I love the closeness and fun they bring. I love eating breakfast together.

trips add a whole other level to overnights too because you get to explore a new place together, make memories, interact with others, and end up cozy at the end of an exciting day with someone engaging to reflect on it with.

There’s nothing like the closeness in sessions that happen after an overnight either. I feel like they bring two people closer together in a special way, and even shorter sessions together after that are greatly improved.

I personally love sleeping separately especially the first couple of times, which is why I have a daybed in my living room: I can sneak out of bed for an overnight if I can’t sleep. I’m a hot and rather light sleeper so being touched or cuddled while trying to sleep is not an option ?
 
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masterpoonhunter

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Just throwing in here. I have had a couple of SP-overnights. Both involved very little sleeping. Significant amounts of evening partying, copious quantities of getting down to it and of course great early morning sex all in the mix but as I recall it, if there was sleep it could not have been more than a couple hours.

Sleeping with (insert your acronym here) is always great once all the compatibility things are worked out. For me it opens up the opportunity to be vulnerable and shed the usual armour I tend to carry and frankly if I admit it, some of the pillow talk is the most intimate of many of the times together.

On the issue of body heat, I tend to run hot and end up on top of the covers a lot, so I sympathize with those who have trouble sleeping with another body generating all those BTU's.

Good topic!!
 
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Riza

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I offer overnights and I break them down into 2 categories. Gfe overnight and Pse overnight. Fairly self explanitory.

Gfe includes going out for dinner, dancing drinks, returning home for fun then snuggling for the night. Also a quick get to know you bang is a good way to start and work up a appitite before going out for dinner. Oh and I love morning wood before you head out.

Pse is partying all night, banging until morning then departing. I don't do PSE overnights. Like Charlee I would need a week to recover.
 

steverino

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Feb 15, 2004
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While I just don't have the mindset for an overnight, I enjoyed the comments as they seem quite insightful. Just like the excitement for a youngster going to Disneyland begins the day s/he finds out that they are going, I could see how the time between booking the overnight and it coming to fruition can generate the anticipatory high. I sense the ladies who manage that part of the experience well will have delighted customers.
 

RobBC

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Oct 27, 2002
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Just like the excitement for a youngster going to Disneyland begins the day s/he finds out that they are going, I could see how the time between booking the overnight and it coming to fruition can generate the anticipatory high.
As someone who has an overnight coming up next week I can say this is exactly how it feels for me right now. Perfect description.
 

Fullhouse

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Nov 6, 2007
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As someone who has an overnight coming up next week I can say this is exactly how it feels for me right now. Perfect description.
Well, I'm NOT looking forward to my 'overnighter' later this week.

I got caught forgetting to pay for a box of condoms at Shoppers Drug Mart. They charged me.
The judge gave me a 24 hour jail term, to be served this Thursday.
 

johnnydepth

Average Sized Member
Nov 14, 2015
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Well, I'm NOT looking forward to my 'overnighter' later this week.

I got caught forgetting to pay for a box of condoms at Shoppers Drug Mart. They charged me.
The judge gave me a 24 hour jail term, to be served this Thursday.
Holy crap, where do you live? In Winnipeg it seems like you get time served if you stab someone.
 

Fullhouse

Well-known member
Nov 6, 2007
1,196
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Vancouver - Richmond
Well, I'm NOT looking forward to my 'overnighter' later this week.

I got caught forgetting to pay for a box of condoms at Shoppers Drug Mart. They charged me.
The judge gave me a 24 hour jail term, to be served this Thursday.

Gee, some of you actually believed this.......WOW ...... for you - I have some Ocean Front Property in Prince George
that I would love to sell you. ... Anybody interested ???
 

PuntMeister

Punt-on!
Jul 13, 2003
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Gee, some of you actually believed this.......WOW ...... for you - I have some Ocean Front Property in Prince George
that I would love to sell you. ... Anybody interested ???
OMG!

PG OFront!

Thought it might take “The Biggie” to see PG OF on the market.

Put me down for 2 acres or 300’, whichever doesn’t have a grow op on it (unless they’re mature plants and the hydroponics are in good shape).
 

Fullhouse

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Nov 6, 2007
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[QUOTE="PuntMeister, post: 2148347, member: 193

Put me down for 2 acres or 300’, whichever doesn’t have a grow op on it (unless they’re mature plants and the hydroponics are in good shape).
[/QUOTE]

Hey, Puntmeister, I can only put you down for 200' of Ocean Front Property. A couple of Sps have picked up the land on either side,
(Big tittie Mittie and Miss Vagina from Regina). .... And the only dope I have on that property lives in the little beach house.

But it does come with a snow blower and an ice auger if you are into outdoor activities.
 
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