I'd never date a working prostitute, it would be an utter mind fuck. Imagine being in bed and feeling frisky or just wanting to have a conversation about shit but your other half isn't interested because she's spent all sucking and fucking other men and making an effort to talk to them so they'll come back. You only have to look on SAAFE to see how many escort aren't interested in a recreational sex life because of the job. It would be madness to go from being a punter enjoying paid intimacy with a prostitute to being the boyfriend of a prostitute who doesn't need physical intimacy with you. It might seem very typical blokey to make it all about sex but the reason why many men punt is because of a lack of sex, therefore a fulfilling sex life is going to be an important part of a relationship.
I've made no secret of an enjoyable social relationship with an escort. We didn't spend every minute away from work in each other's company but we had a lot of contact that firmly crossed the client-escort boundary. When it was time for sex it was strictly paid although there continued some blurring of lines with bookings lasting a lot longer and other stuff, although we always practised safe sex.
The problems always started when emotions started coming in to play as the boundaries continued to crumble. It became obvious that there was a mutual attraction but neither of us wanted a relationship for good reasons. The problems started when the escort started acting like a girlfriend even though she wasn't. She started trying to change how I lived my life but never offered any real incentive to change. She claimed not to be jealous but then acted in a way that screamed jealousy, she was probably fucking far more different people than me. She made constant threats to never see me again when this kind of reaction was uncalled for. If I made a comment about her life it was a serious faux pas whilst, even though she did the same about my life all the time. She got upset when I referred to her as prostitute, something she'd called herself, but used the term punter on me as a form of attack and as another way to try and make me change with no incentive. During one booking she skipped on part of the service she had been paid for after telling me. How guilty she felt about another punter paying for a fuck but only having a blow job, that went down like a ton of shit and she blamed me for it, I was already the boyfriend of a prostitute at that point in her brain rather than a valued customer. Eventually she blurted out that she wanted a relationship with me and that it meant no more escorting for her and no more punting for me, we agreed to have a long conversation about it but then she backed off just as quickly, then she continued all the behaviour of trying to change how I was for no reason. In the end I did to her what she did to me and she couldn't handle it. I got a scathing character assassination message from her that both painted me as someone she would never date as well as telling me I'd broken her heart and made her completely incapable of getting close to anyone romantically or even trust wise again. My last reply to her set out in detail all the shit she'd done that had derailed a brilliant sexual service, a decent friendship and a possible post punting/prostitution relationship. To me the problem was built around x years in prostitution where she needed to be in control combined with a complete lack of self-esteem probably partly from the job and more than likely from other stuff I won't discuss on a forum.
When it was good it was really good, we had a lot of laughs and did some fun non-sexual activities together like meals out going Dutch and shared a lot of normal couple stuff.
Where it went wrong was how her insecurities turned her in to a control freak who started to try and destroy my self-esteem because of her own lack of self-esteem. Fortunately for me I'd already experienced that kind of relationship so knew how not to give in.
If she'd started to work on herself rather than trying to break me down things might have turned out differently.
Prostitution is a real head fuck. It attracts lots of women with problems because sex for money seems like an easy way to make a lot of money quickly, but it's not. If a woman is already damaged, mentally unhealthy or living a damaging lifestyle then sex work will most likely make those issues worse. Fucking men you wouldn't want to go anywhere near if there was no money involved is a sure fire way to increase your problems as much as your bank account.
There are escorts and punters who have had successful relationships. They're probably in the minority. It requires two people to actually deal with their own shit before dealing with having a healthy relationship.
