Getting involved with a stripper/escort?

Is there likely to be a pimp in the background being that she escorts?

Yes, but it might not be a pimp but just a drug dealer she hangs (just friends or fucking/sucking) with to get free drugs from.

Am I crazy for wanting to date her?

No.

What should I prepare myself for (as far as all the stuff that comes with dating her)?

Dont discuss your other sexual partners, dont ask her about her partners. If she asks you, answer honestly, and then ask her. Its best if both sides remain unaware of what happens when you say bye for the night. Even if you suspect she would fuck a homeless bum for a rock, you dont want to admit to yourself and you dont want to convince your heart/dick that she actually does that. You will loose your feelings for her if you know she gives up the same experience to anybody. Just never ask about other partners but assume they are there in the back of your head, but you need to pretend they dont exist.

I would advise to try to fight those feelings. You'll just end up hurt as she disappoints you over and over again. I know it's not easy, and the little head is screaming right now drowning out the big head. But if your even asking here that means the big head has it there. Listen to the big head on this.

Is there likely to be a pimp in the background being that she escorts?
Not necessarily. But she will have boyfriends as well as customers.

Am I crazy for wanting to date her?
Yes.

What should I prepare myself for (as far as all the stuff that comes with dating her)?
Drama. Drugs. Wild times. Heartbreak if you really like her.

Women can and do leave the sex industry. The thing to watch out for is, if it was emotional damage and bad judgement that led her into the sex industry, and is she became more damaged in the sex industry, that won't just go away when she's out. I do think many of these women progress and mature once they're out -- it's been proven that drug addiction causes emotional maturity to delay at the age that the addiction started and then progresses again once the addiction is kicked, and based on what I've experienced, I'm convinced the same happens to many women in the sex industry.

My experiences mirror Jackslash's:
-->"What should I prepare myself for (as far as all the stuff that comes with dating her)?
Drama. Drugs. Wild times. Heartbreak if you really like her."

I have a great cautionary tale to tell you, but I'll skip to the ending: the next morning, the ex-stripper with whom I'd become friends-with-benefits with, sat naked on my bed and called her (wealthy) fiance, and assured him she had just stayed in last night and slept over her parents house. The End.

Of course, there ARE stories of this working out. I'd proceed with extreme caution though.

I'd be more cautious with someone planning to clean up than someone who has already cleaned up.

Not dated either and I'd avoid doing so. I dated a well known English glamour model/porn star a long time ago, probably the best looking girl I ever dated.

"her pussy is a profit center" Lol

I heard Estafador dated a hooker once, I wonder how it went for him?

Great insight guys, I appreciate it.

@Subraman

"I have a great cautionary tale to tell you, but I'll skip to the ending: the next morning, the ex-stripper with whom I'd become friends-with-benefits with, sat naked on my bed and called her (wealthy) fiance, and assured him she had just stayed in last night and slept over her parents house. The End."

Yep. If you date a stripper, you are asking for drama that only 14 and 15 year old girls can cook up. Your story sounds like a teenage girl and her parents. Since most strippers are damaged goods, remember you are just another boy toy in her harem, and just the way you (I assume) thrive of having a harem of girls/strippers for the ego boost, she has a harem of men/customers for her ego boost.

Another plus of dealing with 20 or 30 year old strippers who have the maturity of a 15 year old girl is, they are as passionate and fuck as crazy as back in HS. Its a rush being with them.

I wish you the best with this girl. I'd say you aren't crazy - but since you admit you heavily lust over her - you are probably still operating with blinders on (a little).

There may not be a pimp - depending on how much escorting vs dancing (and OTC) she does.

You should find out if she has a drug habit. I'd highly recommend finding out before she comes to your place. If she has a habit - think twice - and meet out somewhere.

It's never happened to me - because I haven't brought dancers home. But a buddy experienced a home invasion - and was tied up while two dirt bags ransacked his home - only two days after he entertained a dancer in his home.

I'd say on the pimp question, there's a very good chance she does not have a pimp, if she's at least charging lower-midrange prices (say, $250 & up) and advertises in places other than bottom-feeder sites (e.g., backpage). There's a huge non-pimped independent escort community, and the further away you get from low-end, the less likely you are to find pimps

Gingerbread is a stripper who does OTC regularly. So she verges on being an escort. She has a long term boyfriend who knows that she strips but doesn't know that she does extras or OTC. Several of my other strippers also date guys without telling them that they do OTC with customers. I think this is very common that strippers hide their prostitution work from boyfriends and dates.

So you should assume that this girl will continue to do escorting if you date her. Either you can live with that or you can't. I see no reason to think that she must have a pimp. None of my girls have pimps to the best of my knowledge.

I know it is easy to establish feelings for these honeys, but, ask yourself why you want a real relationship. You can already spend time with and fuck whenever you want. When done send her back to the drama without owning it. Why fuck up a good thing?

As far as drugs, she loves her weed (she smokes weed everyday). That's the only drug she does.

Okay fishy, she makes XXX for a few hours of work escorting, unless you know another job where she can make XXX for a few hours of work, she's probably not going to stop, that is unless you supplement her income equally to what she makes escorting.

I've been all over and in some weird relationships, but the closest I've come is:

1. There was an escort that I would visit when I was in town. She would spend the night with me (no charge) we would usually go out to eat, sometimes party and always have sex. We would sometimes have breakfast the next morning then she would leave. Eventually she found a much older guy and she didn't have to work any job (at all) after getting with him. That would be my guess on the ONLY reason she quit escorting. My only guess on how I was so lucky was I was younger than her and she loved sex, and just wanted to fuck someone her age instead of all the old guys she hooked for.

I'm guessing Fishy is still in Cap'n Sav-A-Ho mode, I say to you go ahead, go for it, and get it out of your system. It's just going cost you money, time & probably a lot of drama in the end. When all is said and done it's still not going to be what you want anyway. You want someone here to tell you different you are in the wrong place.

These hoes ain't loyal.

I'd say go for it as I am in a similar situation now. But prepare for some chaos and harden yourself to her likely quirks and bad habits. Most likely she doesn't have a pimp but try to make sure for yourself. If she still escorts and does OTC you should feel free to date others if/when the opportunity arises as long as that continues.

Proverbs 6:26

AMP version

For on account of a prostitute one is reduced to a piece of bread [to be eaten up], And the immoral woman hunts [with a hook] the precious life [of a man].

Unfortunately I have a lot of experience in this area. I've been in serious relationshipside with 3 pornstars and 3 strippers. Each was over a year.

First of all you can't be the jealous type. She probably has many guy friends. The other issue is you mentioned she smokes every day. That's a problem. She's likely lazy and as long as she's smoking she'll never hold a decent job. The other problem with her habit is the weed man. They're going to flirt. And at some point she'll have a new weed man and another.

Do not get emotionally attached to these girls. I learned that years ago and life's been better ever since.

I think twentyfive has good advice. Give it a go - and enjoy it while it lasts. It's probably not going to end well -

The other piece of this, of course... on StripperWeb, you often hear the girls talk about dating a customer (most have rules about NOT dating customers, but a huge % came by that rule because they dated a customer at least once), and they say something like, "these guys think they're in love with me, until they get to know me and find out I'm a real person".

Which is a pretty big spin -- it's not that these girls are "real people", I think we all know they are, it's that we find out that their hustle personal is covering the fact that they're horrible people, or more often, people who have some wonderful things about them but also damage and bad things about them on a level most guys would never have run into when civilian dating. This, really, is the crux of the problem ... it's not easy to tell how much they're covering up that damaged parts that lead to drama, infidelity, manipulation, heartbreak...

Thanks for the insight fellas.