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Sleepovers. a good or bad idea?

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Lately I've been pondering having an overnight encounter. I miss that feeling of falling asleep next to someone and waking up next to them. The unique circumstances of my last relationship prevented my gf from being able to sleep over. So it's been a while since I've actually slept next to a woman. I'm currently lying here now and really kinda sad and lonely and missing it.

 

But I have worries about an overnight encounter causing the lines to get blurred. I'm afraid that the added intimacy of spending an extended amount of time together and sleeping together (actually sleeping) could cause me to develop certain feelings which are better left unfelt. I know what this buesiness is and I don't and won't have any illusions.... if I were to develop such feelings I would probably not act on it for fear of putting her in an awkward position....but I still would like to avoid that emotional rollercoaster in the first place if I can. For these reasons I've never spent more than an hour at a time with any SP...to keep the lines clear in my mind. Lately I've been tempted though. I guess I'll never know for sure if this problem would even arise if I don't try.

 

Guys, have any of you encountered this sort of problem from an overnight encounter? And if so....how did you deal with it? Ladies....have you experienced any similar problems from longer encounters with trusted clients? Looking forward to any input.

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I think being clear with yourself about who you are and your boundaries is a great start. Why not take little baby steps and have a longer (2-4 hours) engagement with an SP you like? If that goes well, you can try an overnight.

 

Also, there are many SP's who cater to the sort of relationship you may be interested in cultivating with an SP. The intimacy and closeness you need are still there and still very genuine and it's still understood that it is a business relationship.

 

Like any relationship, business or otherwise, when emotions become involved things can get tough. It might end badly,or you might discover you have an incredibly rewarding relationship that goes on for years.

 

A better question to ask yourself is this: Is the risk of becoming emotionally involved and having to (potentially) stop seeing your provider worth the intimacy and closeness that you desire?

 

Or, a better way to put it might be: life is too short to worry about potential future issues that may or may not happen. If you want to try an overnight, do it! You have to follow your feelings. You have a need that is not being met. You might become emotionally involved and you might have to end it and that would suck. But you'd probably still say that it was worth it anyway. You can't live your life always trying to prevent bad things from happening.

 

Alternately, you might also find that your feelings, should you develop any, are not unrequited at all, but in fact, returned by your SP. I'm not saying you should hope for this or think this would happen--but it HAS happened now and again (though it is generally rare).

 

Get out there and have some sleepover fun!

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Heya Castle

It sounds like you answered your own question there in a way. Whatever you decide, I'm sure you will be fine but I will say this.

Anyone that doesn't have some sort of feelings for the person touching them or sleeping with them then there may be something wrong with them. Everyone has feelings or thoughts like "she's nice" or "what a sweet heart". Myself I wouldn't let someone touch me if I didnt have a positive feeling about them. It's a great thing to have positive feelings for someone you are sharing a special moment with, keeps us human. What's the worst that could happen? You call her again?

Though I'm sure you mean feelings as in heart string tugging feelings. You mentioned that you haven't felt the warmth of a woman in a while, in the case of heart strings, I'd for sure second Berlin's motion of extending your sessions a wee longer at first. Your heart is vulnerable, not just to SP's. Be the King of your Castle that you are and you will be just fine. And hey, if you just need to feel a soft female, sleep beside you to feel great, I don't blame you.. I'll come over, we'll play some poker, I'll pee with the door open, eat your food and talk about my ex a lot and how you remind me of him, then I may or may not nag you for something you'll never know so you'll be on your guard...Finally when I've exhausted you and we've watched our 3rd season of Gilmore girls, we will pass out together in each others arms because I wont let you leave anyways and if you try to pee I'll ask "where you going?, hurry up" We will ultimately cuddle since you will already be curled in the fetal position, straddling your pillow asking yourself "is it morning yet?" I will wake you in the morning from the sounds of the loud gas passing that I held in until now, forgetting you were next to me, roll over and ask for payment, heck, I'll do for free, any day, cause, I care that much. Then I do believe you won't have to worry about your feelings interfering :)

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I don't want to get too in depth or personal. I don't now you that well, and this isn't the place, but here goes with a some of my thoughts.

 

Once again, I get the feeling you are similar to me. If you are already worried about awakening or creating feelings that are better left unfelt, there's a good chance your subconscious is trying to tell you something. Being alone definitely sucks sometimes, but sometimes our brain tends to fixate on the quickest/easiest solution. Unfortunately the quickest or the easiest solution is usually not the best one. Don't get hurt dude.

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Heya Castle

It sounds like you answered your own question there in a way. Whatever you decide, I'm sure you will be fine but I will say this.

Anyone that doesn't have some sort of feelings for the person touching them or sleeping with them then there may be something wrong with them. Everyone has feelings or thoughts like "she's nice" or "what a sweet heart". Myself I wouldn't let someone touch me if I didnt have a positive feeling about them. It's a great thing to have positive feelings for someone you are sharing a special moment with, keeps us human. What's the worst that could happen? You call her again?

Though I'm sure you mean feelings as in heart string tugging feelings. You mentioned that you haven't felt the warmth of a woman in a while, in the case of heart strings, I'd for sure second Berlin's motion of extending your sessions a wee longer at first. Your heart is vulnerable, not just to SP's. Be the King of your Castle that you are and you will be just fine. And hey, if you just need to feel a soft female, sleep beside you to feel great, I don't blame you.. I'll come over, we'll play some poker, I'll pee with the door open, eat your food and talk about my ex a lot and how you remind me of him, then I may or may not nag you for something you'll never know so you'll be on your guard...Finally when I've exhausted you and we've watched our 3rd season of Gilmore girls, we will pass out together in each others arms because I wont let you leave anyways and if you try to pee I'll ask "where you going?, hurry up" We will ultimately cuddle since you will already be curled in the fetal position, straddling your pillow asking yourself "is it morning yet?" I will wake you in the morning from the sounds of the loud gas passing that I held in until now, forgetting you were next to me, roll over and ask for payment, heck, I'll do for free, any day, cause, I care that much. Then I do believe you won't have to worry about your feelings interfering :)

 

Waaaaay too funny ! I like your sense of humour JuliasUndies. And I agree with the advice. Go for longer sessions first. Overnights are not for everybody. I have had three with very special SP's. Did I fall for them? I love ALL the ladies I choose to be with for more than an hour and I don't need to feel like they are my wife or gf at least not emotionally or to the point where I leave the door open to pee !

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Castle,

I don't know you well either, but have read your posts. I think Surf Nazi makes a good point, not that the others haven't either from their perspectives.

 

Lonely isn't always that much fun. It is in the small hours of the morning I find it too. BUT the one person you can't escape at 4am is (often the darker part of) yourself. He's the guy who doesn't need any more anguish than he has now.

 

"Baby steps" is right, but it is both warm and pleasant and the edge of slippery slope if you can't keep the boundaries. As was said in lots of other threads, communication with your companion upfront may be the best reassurance you can get that things will stay on an even keel. You may have to work at it !

 

Take Care,

CB

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This thread certainly touches a sensitive part for me. First Berlin, I love everything you write and your post here certainly has my thoughts and beliefs well captured. I got into this hobby just over 2 yrs ago. On surface thinking it was because of the sexual encounter, excitement and satisfaction. I've learned I was missing much more in my life. A partner, intimacy, a friend. I know this now more than ever. So reconciling that need vs the other extreme...(it is ONLY a 2 hr business appointment) has been very difficult for me. Both to find a lady that would allow me to go there and want to share that in a 'relationship'. It has evolved but has meant a great deal of communications between us and an almost constant self-reflection on where I am and what I'm feeling. It is abit of an emotional roller-coaster but I also think the personal process has helped me grow and become a better, more confident and self-assured man. I'm not totally there yet but would not change a thing in how we/I have evolved. And as some have suggested our dates have expanded from 2 hrs, longer dinner dates, and not long ago an overnight.

 

My advice, know yourself well...which it sounds like you do. Keep checking in on what is going on inside you. Communicate with your partner. Best of luck. Cub

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The overnight encounter does indeed present a set of dynamics different from a short one hour encounter or even from that of a longer multi-hour liaison. I appreciate and truly understand everything that Castle has written here as I have had the identical questions and musings. I absolutely understand the sadness and loneliness that at night sometimes comes with the realization that there is not a special someone to curl up to, or just touch and hold. That is a feeling that cannot be replicated without having a special someone to share it with.

 

The lines can easily be blurred, and it is important to keep in mind the context of CERB, how and why initial meetings happened, and that there are boundaries. That is not to say that in special circumstances those boundaries cannot be mutually crossed, but I would think that that would be the exceptionally rare circumstance.

 

An overnight is potentially a very intimate sharing experience between two people.

 

I have had overnight dates, and they were very special, not only to me, but I believe as well for the women who shared the experience with me. They were more than simply business transactions. Did they cause 'feelings' to develop? For me the answer is no, because those 'feelings' were already there prior to the overnight, otherwise the overnight would never have happened in the first place.

 

So what are those `feelings.` For me it is not love as I have defined it for so many years. It is caring. It is connection. It is respect. It is having that extra comfort level with another person. It is mutual pleasure. It is a meeting of minds. It is the ability to relax and share things about oneself and with each other. It is learning new things and perspectives. It is in whatever context, a special friendship. Without those things already being present I would not seek out an overnight. The overnight can enhance these things beyond my ability to express, but with care, communication, truth, honesty and sincerity, it can be something that both parties can enjoy as special without assuming anything more.

 

If you can do that, and yes, it is an emotional rollercoaster, then an overnight is a truly special thing.

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Castle there is nothing wrong with what you are wanting. Berling make many good points ; none better than ' life is too short to worry about potential future issues that may or may not happen.'

Personally I really like the overnight experience. For me it is about connecting with another person . Spending time talking, shareing, laughing and exchangeing ideas and then there is the lots of great sex aspect. A regular date with a lady can be all of those things except the lots of great sex is not a given.

And of course there is the going to sleep with a new person and wakeing up with her. I can't say there is anything better.

For me it happened quite early in my ' hobbying' I had only see 2or 3 SPs before I saw a young ladies' ad and I knew that I wanted to sleep with her. When I enquired about it I found that she worked with an agency and the arranging lady ( madam) ( what is the word I want) said that we couldn't do that.She recommended that I see the lady several times to see if it would work, so I book a 2 hr appointment at my earliest date.I knew that my point would be to make myself as desireable in those 2 hours as possible.

The appointment was wonderful but as I expected not as long as I wished. The next time I called the agency I asked about an overnight appointment the arranging ladys said she would ask the lady and get back to me.She got back to me the next day saying, the lady liked our experience very much and we need only set a date and a time.

My very first night was a beautiful experience. Since that time the lady has left the agency. We are close friends that see each other a number of times each year and keep in touch often. It is always an overnight. It is always wonderful.

I still see other ladies, a few of them I have shared over night experiences with and some a few times.

Each of these ladies are a different experience for me and I suppose I am a little different experience with each of them .

For me the overnight is the ultimate experience and I guess in a way, although I don't intend it, the a regular 2 hour appointment for me is like an interview to see if we would be compatable for a much longer appointment.

I don't have trouble loseing track of the idea of an exchange of money.

All this said I think that you can assume that many ladies are would rather not have this type of arrangement ; but from my standpoint it is very satisfying.

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Guest **cely***r***ne

I love overnight encounters! I have had a couple of them with the same person.

 

As JuliasUndies (I really like your name btw) somewhat mentioned, if there were no feelings towards the parties involved the whole thing would just be so awkward and robotic, when it should be all about enjoying eachothers company, and having a blast!

With sleepovers, you get more time to really get to know them, and see certain sides of their personality you just wouldnt get a chance to with a shorter date. I can understand how this would "tug at heart strings" though. I for one believe in love at first site. So I am probably contradicting myself a little when I say that a sleepover with an SP wouldnt have you falling head over heels, because it does happen. And sometimes it really sucks to put the business aspect aside, because you could potentially genuinely care for her.

 

Knowing you personally Castle, I can say that you are a true sweetheart, and the lady who gets to sleepover with you is a lucky one! But how would we ever know anything if we didnt first try and see how it goes?

 

We all love the feeling of someone beside us, the warmth of their body, the security we feel and a certain level of inner happiness it brings.

 

I hope this makes sense to you, I am writing this without having any caffeine in my system.

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We are close friends that see each other a number of times each year and keep in touch often. It is always an overnight. It is always wonderful.

 

It is not uncommon to become friends with someone you do business with, be it Wallstreet, massage, or escorts.

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I agree with what others have said. I particularly want to underscore Berlin's advice to try longer meetings because my intuition is that you want more than sex, you're looking for an intimate connection.

 

I love the meetings that start out with dinner. Usually, we've exchanged e-mail, maybe we've talked on the phone a time or two. By the time we meet, we have a lot to talk about and dinner is a great thing to share. It feels like there is a more genuine, natural connection by the time we move on to other things.

 

That said, the stereotype that many men just want to talk to escorts and don't have sex with them really is true more often than one might imagine. I've had fabulous evenings with amazing, thoughtful, caring gentlemen without ever getting into bed. I know that neither of us ever felt cheated or let down because we didn't have sex. The connection, conversation and engagement were all we needed.

 

I only do overnight meetings with clients I know and am sure that we will both spending so much time together. Sleeping with someone is such an intimate activity for me that I'm very cautious about it.

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