“I’m falling in love with an escort”

I have been seeing an escort for paid sex on an irregular basis since April. I had seen other girls before, but this one was the first that I liked enough to see again. I understand you may have already judged me as some vile pervert just from those first sentences, and I would not blame you. I take no pride in it, but hear me out. I really like her. We connected on a physical and intellectual level, I enjoyed the conversation as much as the sex, which says something as the sex is incredible.

I also think that because I’m the only client near her age — I’m 24 and she’s 21 — she feels that she can open up and relax with me. Last time we met she didn’t seem to want me to go, despite my paid time being up, because we were so deep in conversation. I had to stop it to leave as I felt bad I was taking up her free time. She also seems to like that I care that she enjoys our time as much as I do and comments about my oral skills every time.

I’ve recently joined the Army and start in less than a week. I told her that this means I can no longer see her due to the risk on dismissal and that this week will be the last, but she wants to write to me while I’m at training and even said she wants to send me pictures to keep my spirits up. I’ve had feelings for her since we first met, thus why I continued to see her, but I thought she would never see me as anything more than a client. I’m still not sure. It feels like she’s taking a personal interest in me, but I might be misreading the situation. I also don’t know how to win the heart of a girl who has men pay for her company, not that her profession bothers me.

If something were to blossom between us, I wouldn’t put any pressure on her to stop. That can only be her choice. I see her on Saturday, I’m thinking of just telling her how I feel. I doubt she’ll be shocked, but at least I’ll know where I stand after that.

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5 thoughts on ““I’m falling in love with an escort”

  1. Anonymous says:

    I think you should. She is a person just like anyone else. Go for it! Just don’t judge her if she turns you down. Best of luck to you with her and over seas.

  2. Anonymous says:

    This is interesting as I’ve had a somewhat similar experience. I have some very good perspective on the subject from both sides. Tell her how you feel, but be cautious. You’re right to feel that it’s difficult to win her heart and many sex workers are only going to be interested in you for the cash. Being a good customer, being someone she enjoys spending time with are bonuses for the most part and let’s face it, good for business. So go forward with that in mind, and tell her that you would like to see her without it being a transaction and not involving sex. If that can happen, you’ll have a much clearer idea of how she’s feeling. That’s your starting point. If she won’t see you in that way, you’re just a customer. Period, end of story.
    That’s your starting point. Second, you say that you don’t care that she works as an escort and you wouldn’t put pressure on her to quit. I’ve heard this from a few sex workers, it’s very difficult for them to do that job if they are dating. Because if their partner is okay with the job, that’s not a good thing. And if their partner is not okay with the job, that’s also not a good thing. You want her to quit. You don’t have to pressure her, but if you want to be with her, you need her to quit for your relationship to be healthy. If you’re able to see her personally (unpaid) then you should tell her that. If escorting is her only source of income, that’s not going to be easy for her. If she has other employment outside of sex work, that’s a very good thing. If you can start dating her with the idea that if you become exclusive she will need to quit, then you might have a chance to build something solid. If that is not a possibility, you’re in for rough times ahead. At some point, it will bother you that she’s having sex with other men. And if it doesn’t bother you, it will bother her that you don’t care. You can’t love her so much that you don’t care about that side of her life. Remember that this is a job for her, a source of income and chances are high that she’s not looking for a romance with a client. Maybe things are different for you two, but you need to be careful that you’re not being blinded by the situation.
    For me, I saw a few girls regularly, but never had feelings for anyone but this one girl. I saw her exclusively while she worked and we became very close. I could never be sure of her feelings until she agreed to see me in real life. At that point, she would also pay for dinners and lunches, especially in the beginning. Then we would take turns at my insistence. We grew very close, but it’s also more complicated because I’m married and I don’t know if we’ll get the chance to be together.

  3. Anonymous says:

    Dear Ano #2: Have you talked to your wife about being polyamourus or considered a open marriage?

    • Anonymous says:

      No, that could never happen with either of the women. My wife and I are talking about our issues that we’ve had and are going for counselling to work on it. I’ve cut contact with the other woman while we work on fixing our marriage.

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