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TIFU by falling for an escort

Patrick O'Neal

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I'm a lonely, nearly 40 year old divorced man and for the last nine months or so I've been scratching both my social and sexual itches by seeing various escorts every two weeks or so. It was going fine, I enjoyed chatting with the ladies I was meeting, then progressing to generally enjoyable sex.

A few months ago I met a new lady who I hit it off with. We had a massively similar range of other interests (and for clarity, this wasn't her just pretending to be interested in the same things, as these were things she volunteered first), similar sense of humour, and the sex was pretty damn good. I decided to keep seeing her regularly, but soon realised I was developing the feels. I decided to ask her on a date, making it clear it would be a personal engagement rather than a professional one, which she politely declined (which was fine, it was what I was expecting). We continued seeing each other on a semi-regular basis. A month or two later, I decided I was starting to have difficulty separating my feelings from our time together, so I decided it was time to move on before things got any worse. I met her for a final time, explaining to her why I could no longer see her as a client.

This is where things got weird. I expected her, based on our previous interactions, to understand this. Instead, she unexpectedly became quite emotional and said she didn't want to stop seeing me. After more discussion, she asked for my phone and promptly entered her proper name and personal phone number into it. This, I know, is basically breaking rule #1 for escorts, which is never reveal your personal details because of the issues over safety. She wanted me to get back in touch with her about a week afterwards, as she was aware I had care of my children for a period of time, and to organise an actual date with her.

Today was the end of my time with my kids, so I sent her a message asking her when she was available to meet up. She responded saying her boss had found out that she had given me her personal contact info and was mad at her because he believed in doing so she had lost me as a client (she had already effectively lost me as a client before she did this, as I had made it clear we wouldn't be meeting professionally anymore). She asked if we could delay meeting up and if I would come back to her as a client, which would get the heat from the boss off her, with the intent that once things had cooled down we could see each other without him knowing.

The cynic in me says that there was never any intention to go out, and that this was all just a desire to keep me as a client. But what confuses that for me is her giving me her personal details. Having been a client of this industry for some time now, I know how seriously these ladies guard their personal details, and handing them over for the sake of trying to retain one semi-regular client seems unlikely. I know also there is the possibility that her boss is coercing her to try and do this, eg threatening to stop her working as an escort.

The unfortunate end to the story is despite having convinced myself that there might actually be a genuine connection between us, one that could develop into something more, I've had to made the decision to just walk away. It's left me feeling both depressed at my hopes of finally having met someone being dashed, stupid for tricking myself into believing it in the first place, and angry that if this was a genuine connection, the circumstances of our meeting basically ruined any chances.

TL:DR: I managed to convince myself that there was a chance of a genuine relationship with an escort who I had been seeing for a few months, only to be disabused of that delusion today and now I'm depressed and venting at my own stupidity.
 

Dog Eater

Paint Tin ASMR Enjoyer
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TL:DR: I managed to convince myself that there was a chance of a genuine relationship with an escort who I had been seeing for a few months, only to be disabused of that delusion today and now I'm depressed and venting at my own stupidity.
TLDNR

Do you fuck her raw? Lick her asshole? Where do you cum?
 
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