I’ve only once in my entire life have been with a prostitute (that I know).
To me a huge thing about the chase is the ego boost when I have to work for it and a smart, beautiful woman falls for me. Don’t get me wrong, if I do the math I think prostitutes may be the smarter choice. Without 2 divorces to my name, I wouldn’t even have to work at this stage in my life (but I probably would, I enjoy what I do).
I have been to corporate events in Cuba and Hungary and Russia and Manila and many others, and high class professionals were there and beautiful, and aplenty. I was very tempted in Cuba (you find every mix of shape, skin and hair color you can imagine, and she was spectacular) and Hungary (probably the most classically beautiful woman I have ever seen, and very classy on top) but passed both times even though afterwards I probably masturbated myself raw in the hotel room. Both of them never talked about bulge or size, it never came up, they just said I’d do them a favor by picking them, because there were a lot of other execs in the party that… simply didn’t look or talk like me. But I said sorry.
But in Vegas, her name was Simone. I was in the sh*t zone with my ex-wife, she’d withheld sex for over a year and I had not been with anyone else because I really, really cared about her and wanted us to work out. But there I am, very high end corporate party in that club on the top floor of Mandalay Bay or THE Hotel, forgot which, black tie event. I wasn’t strictly invited, but was friends with the salesperson of the year (who had designs on me, I found out later in the week) so went as her date, but we both were like “Hey, once there we’re free to see”. So she quickly found her guy and she said bye, and I am there spending time talking here and there with the very few people I knew, noticing that everybody was completely drunk by 8pm while I actually had been paying attention to the very good jazz band they had. And this is Vegas, and at night, so there were ladies of the night around even though it was a private event. So I sit at the bar and order myself a glass of dry French rose and sip on it, and after a while, this exquisite vision materializes next to me. She is super-exotic and has a shape on her that would tease an erection out of the statue of a monk. She later told me she was PolynesianHawaian-AfricanAmerican-Scandinavian, and I believe that. We start to talk about stuff, I share her traits of exotic looks which people can never place, and we share our DNA histories and where we have lived and blabla. But in talking I find out she is definitely not in the industry that sponsored the event, and ask her about that. She is quite direct - turns out she had been hired to provide entertainment to a VIP guest, and that’s exactly what my tag said, bless my friend. There were 10 of them in the event, she said (I had seen some other spectacular women walking around) and she touched my event badge and told me “I like you. You know how to handle yourself around a woman. I do what I do, but I do it with class, and want to be treated with class. Your badge here [tap] can make me $1.5k. You can show me off for 4 hours, or take me to your room for 2 hours. What do you think?” I proposed “Women like you can be a cruel bunch, I have heard. You say you have class, so let me make up my mind. You know you are spectacular, but I have never done this before. So, I’ll throw in a bottle of Dom Perignon and a nice dinner, and if I want you after I’ll throw in an extra 750 for the exquisite company.” And she’s “Spoken like a true gentleman, I accept. I like how you do business.” And I smile and say “Wait until I do pleasure” and she laughs. So yeah, I’ll cut the story short, we clicked and ended up in my room.
She knew her business. She asked “Do you want to play some music?” and I played some upbeat Jagged Edge song I liked at the time, and she was like “Wow, I love this song, I am surprised you know it” and started to dance and undress. I was worried about my cock not getting hard with what, in the end, was a prostitute, but boy was I wrong. She danced, she was naked, I muzzled on those absolutely gorgeous tits, and then I undressed. She was amazing. Now I have always told you guys I truly have never seen myself as particularly big -I finally accepted I was big about 5 years ago or though, I just didn’t give it much thought- but when she saw my cock, Simone went “Daaaamn P. I didn’t bring extra large condoms. You should have told me something hon. You look very healthy, but no condom is an extra 5k, I only do that with long term customers, but I like you.” I answered “That’s exactly why we’ll either use a condom or find some other way, Simone. I have some and you can inspect them.” And so she did. I told this story to a more experienced friend of mine and he told me in theory they are not allowed to do that.
One thing she consistently did that shows she was a professional - she never kissed me on the lips. But she let me kiss her cheeks, her neck, her back, her magnificent ass and her upper inner thigh. And when we fucked, she did react to me. Of course she was was a prostitute, but as I am doing my favorite thing, she does what women do when they want to get off, she gets on top of me and you can tell she’s developing her own little cadence, and then she trembles and sighs as I suck on her nipple (she had nipples similar to a Romanian ex of mine, who loved to ride me and would cum if I sucked on her nipples at the same time), and she buckles some. She truly says “Boy you’re so good” and we go some more. But I can’t cum in her with the condom on. It just doesn’t trigger me. She’s then “I don’t want to leave you hanging - what do you want?” and I ask “Baby oil, handjob and your tits?” and she’s “Oh yeah!”. Minutes later, I shoot my first cum over a woman in over a year, and it was a good one. And then she didn’t leave. She was curious about me, as in “Why does a man like you do this?” and I answer “Two things, Simone. First of all, you know you are spectacular. Second of all, my wife doesn’t fuck me, and honestly it’s my damn fault.” Then she’s like “How about we go downstairs and have another drink? I like being with you.” And so we did. After the drink (we spend a good 2 hours talking, it was after 1.30am), she’s like “Do you want me to come up again?” and I ask her “How much?” and she just says “Whatever you want to give me. I am tempted to come up for free, but I can’t.” And she was true to that. We did it again. Because we had established more intimacy, this time I did cum really good (with a condom) while stoking her good. She did the exact thing on top again. Afterwards she was “You know women, your wife is lucky” and I say “Wish she’d think the same, then again I don’t think I’ll let you call her and tell her, you know?”. She then left, but gave me her number and said “I’d really like to hear from you again, I had such a good time.”
I never called her again, but it’s the one time I was with a prostitute, and she was awesome.