High School Crush

In high school the most beautiful girl (voted on by the students and teachers) was Joan. A bit taller than the average girl, perfect body shape, incredible legs, nicely shaped ass and tits just the right size (though I never saw the ass or tits). Joan was so damn beautiful she was unapproachable. She dated outside of school, not that I would ever have asked her, I never asked any of the girls for dates. I was incredibly shy. That wore off in college at least.

Fast forward and in my life, I went on a fast track, graduate degrees at 20, made a name for myself in my business, and now travel the world on business sometimes staying over if I like a place. I keep an apartment in New York, Paris, Berlin and San Francisco. I am from the midwest and have a small home there but I guess you could say that I base mainly out of New York. I concentrate most of my efforts on business I don't spend much time dating, and haven't had a steady girlfriend since I first left grad school. I guess all that is a build up to making excuses of why I hire hookers.

In New York, I had an evening free and called of the the upscale services and had a girl come over. Yes, you saw this coming, it was Joan. She called herself Mara instead of Joan, and to tell the truth I didn't recognize her right off. I had to use my real name of course and after she saw me she recognized me. After an awkward "How are you" conversation we transacted business. We felt each other up, I stripped, then stripped her, and she sucked me hard, and I fucked her. Asking if she had time or had to go to another appointment, she said I was the last of the night. So we got dressed and I took her to dinner. I got the whole story. She had a college degree, actually held down a hospital lab job during the day and 2 evenings a week and on weekends when she was free she worked as an escort.

She was still strikingly beautiful, and I was right as a teen, her tits and ass, along with her pussy were perfect. She had a perfect body to go along with her perfect looks. She did the escort thing for money. Living on a lab salary with out a man in her life was tough in the city. I asked if she'd like to see each other or if only through the escort service. Hesitating she had to think about it.

She called me a few days later and asked over the phone if I could resolve myself to the fact that she was an escort. I asked if she could resolve herself that I was the type of man who needed to call escorts. That was the trick we dated a bit, without sex. I didn't want her to think that just because we'd had an escort transaction that it automatically meant that she was up for sex in her private life.

We did start having some sex privately, she was still escorting, even leaving me a few times to go to clients. I asked her to come back after. It took her a while but eventually she realized it didn't mean anything to me, and our sex started to be bareback without condoms, and I even talked her into anal sex occasionally.

That's where we are now. I've taken her to Europe and s. America with me on a few occasions, even vacationing together in the south of France for two weeks. I wouldn't mind asking her to move in with me, or even get married. Not sure she'd do it though. But I think she'd rather not be a high class hooker, but remembering her she might want me around as a reminder of that life.

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Comments

Anonymous

by Anonymous on Feb 16, 2024 at 12:13 PM

Why not I have dated women that were screwed by many for free. I think every women has some sort of slutty side to them. It won’t hurt to ask. I know my current GF who is gorgeous has been fucked by many. Who cares at the end of the day if you’re the one she chooses. Who cares. Definitely something to keep to yourselfs when asked how did you guys meet back up

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Anonymous

by Anonymous on Feb 16, 2024 at 2:02 PM

I had a LT 6’ super long legged green eyed blond gf who did modeling. Of course I was the jealous type which pissed her off, but later my thoughts were justified when she fucked around on me multiple times. Dont get too intense with this girl asap but gradually get closer. Take it from me, the hot ones you need to lock her down with a ring as quickly as you can without scaring her off or someone else will

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Anonymous

by Anonymous on Feb 17, 2024 at 6:47 PM

that's nice. you should ask her to stop escorting and then you can both enjoy the services of an escort, since she's a former escort she will probably like to be on the other side of it for once.

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