Sleepovers with sugar dates

Sarah, an old ‘gal pal’ I used to know many years ago said to me once:  ‘Dave I can’t believe you did a sleepover.  Sleepovers are weird, you actually hold someone in your arms overnight’.  ‘So what? I like them’ I responded.  I have only done a very small number of sleepovers. A few with someone I almost married long time ago, and only 3 with old SBs. I offered one to someone who, let’s call her, ‘Blondie’ years ago but she said ‘Montrose, both you and I know better so I will politely decline’. She was right perhaps. She was referring to the fact that once you sleepover with someone it may become something more and it also signifies that while you are sugaring the liaison is developing into something more and the two of you have become very comfortable with each other.

Let’s see how my old sleepovers went:

1. The first one was in Texas when I flew over this lady I was seeing in NY. She stayed with me for the weekend which was a mistake. Why? because I feel weird hosting people in general so having someone for 2 and a half days right on top of me was a bit too much. We ended up having a little fight via email when I mentioned that while it was nice there were a few details (like sex) which did not go as planned. I liked it but it could have been better

2.   A couple with Serena. Those were the best and I was amazed how open she was to the idea of having one.  Interestingly, she broke up after our second one. We hadn’t seen each other for a while, she started seeing someone else, then we had the sleepover, then she gave me a kiss on the cheek and took off. It happens, I guess.  Come to think of it, after each one of these sleepovers we broke up

3. The French Moroccan lady in London, ages ago.  It was hot, but after that I just wanted to get rid of her,, way too much bubbly personality

4. College: playful and close, and time will tell what happened

So sleepovers are tricky: if you already friends and get along personally, that’s great. If not, then might as well just remaining casual dating partners and skip the whole sleepover idea


This entry was posted in Dating, mutually beneficial relationships, No strings attached relationships, NSA, Sugar Daddy and tagged . Bookmark the permalink.

9 Responses to Sleepovers with sugar dates

  1. Ah, sleepovers… haven’t ever had one. I sort of draw a line there, although I really wanted to have one with Hayden (my 3-year lover) and with Jade (because she was so sweet). But they never worked out. Still sort of feeling that out. I’m pretty sure I’ll come to think it was a mistake, but still…

  2. Hey, downtown LASD, please no names. I hope those were pseudonyms. Just to protect the privacy of others.

  3. Kit SB says:

    I’ve had countless sleepovers with my sugar daddy. He loves them and I do too. It’s nice once in awhile!

  4. Robert says:

    I try to avoid SB’s . I like escorts, I pay them to leave.

  5. Robert says:

    That is why I like escorts, I pay them to leave

  6. KittyKat says:

    Just don’t do it. It makes it something else and if that’s not what it is…don’t go there. You are setting yourself up! All I have to say.

  7. Hmm..makes it something else, yes…you are correct. It’s not recreational NSA anymore.The two parties will leave thinking a lot about each other

  8. Southern Gentlemen says:

    I have a SB in Texas that I see every two weeks. I pay for her a monthly allowance that is exactly for her apartment. So I sleepover every two weeks. I love waking up next to her, except on my 4:30 early flight mornings when she like me to be quite and not turn on the light!! We have been together for over a year and it has not made our NSA deal something it is not.

    She has a serious BF and I have a Wife. We just don’t make a big deal about it. But sleeping over is my favorite part of seeing her. Also it makes it feel like she is not an escort. I know she is not but it makes our arrangement much better. Also a hotel room is $ 300 a night that I save so it makes our arrangement that much cheaper.

    Don’t knock it till you try it. I love it.

    • Have tried on several occasions and had a great time. I am concerned that, depending on the SB, she may start thinking it as something it is not and making all kinds of conclusions in her own mind. Been in that place as well

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