My Biggest Regret When it Comes To Escorts

Image with the blog post title along with a man showing regret

When guys talk about hookers, strippers, and partying in Vegas, there’s plenty of room for regret to sneak in there somewhere.

Usually, it has to do with money, being too trusting and getting ripped off, or just not knowing when to say enough is enough. But this story is a little different, and it’s more about regret when everything goes right.

If you have experience with escorts, I think you’ll understand what I’m about to say. If you’re new to the escort scene, this may give you some insight into how it can sometimes all come together.

Sex With Escorts Can Be Pretty Good

Sex with escorts isn’t always the best. Sometimes it’s clunky, or the escort is just not into it at all. Othertimes, you and the escort are just not a great match sexually. Finally, something can throw you off at the last minute, and you just don’t perform well. For example, she tries to hit you with some upsell, and it ruins the whole vibe.

But sometimes, everything goes even better than you thought. You and the hooker are a perfect match sexually. If you’re new to escorts, you may think this doesn’t happen, but experienced guys will tell you that it absolutely does.

It’s sort of random. It’s just a perfect combination of your tastes, the right girl, and the right time, all matching up for some amazing sex. When this happens, the reaction of the escort afterward confirms it wasn’t just all in your head.

Now, you may be thinking the escort was just acting, so you can’t believe that. But let me address that with two points.

1) I’ve had plenty of awkward encounters with escorts that weren’t great at all, and afterwards, you could totally tell by her reaction that she felt the exact same way.

2) After it’s over, she really doesn’t have to act anymore, and plenty of girls just stop the acting as soon as it’s over.

What I’m saying is that you can definitely tell if the sex with an escort was good (or at least fun), both from your perspective, but also from hers. Yes, sometimes her reaction is fake, but my point is, sometimes it’s genuine, and you can usually tell by the reaction afterward. If she had a good time, you’ll easily notice it. If she had a boring time, you’ll notice that too.

But that brings me to my biggest regret. It’s not from seeing the wrong escorts or spending too much money. Instead, it’s when I had one of those great encounters, and I didn’t follow up and see her again.

In my mind, I’ll occasionally remember back to a particularly great encounter with an escort. But then I wish I had tried to see her one more time to see if the experience was the same.

Of course, sometimes I did see the escort more than once, and sometimes it ended up being a lot of times until we both moved on.

But there were plenty of times I had an amazing time and just never contacted the girl again. And that’s always been a regret.

I’m not saying trying to recreate a great time will always be successful. Maybe you and the escort had just the right amount of alcohol, and she was in a great mood that particular night. If you tried it a second time, it may not have been nearly as wild as the first time.

But even with that possibility, I sometimes regret not seeing some of the amazing escorts I’ve met more than once.

What I’m saying is that if you have one of those experiences, don’t be afraid to immediately see her again. Here in Vegas, try to schedule for the next night, if you have the budget for it.

And yes, that may be another reason I’m not always quick to schedule again. If you drop $500, you may want to chill a bit before dropping another $500, but everybody is different with money.

But if you have the budget and the time, don’t be afraid to see the same escort again. It may not be as perfect as you imagined it the first time, but at least you won’t have any regret. And you never know, the second time may be even better.

Being in Vegas, I guess it’s sort of like gambling. You have to savor the wins because there are plenty of losses that go along with that one big jackpot. Finding the perfect escort isn’t common, so when it happens, try to enjoy it as much as possible while it lasts.

…Just don’t get carried away.


If you need the inside information about escorts and strip clubs before your trip to Vegas, check out my two complete guides: The Ultimate Vegas Strip Club Guide and The 2026 Vegas Escort Report. Both of these guides have information you won’t find anywhere else, and they’ll help you find the experience you’re looking for in Vegas.


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