Chester Teaches Margo: Part I

      The doctor is a contender for one of my least favorite clients ever.

       Not because his session was unpleasant (though it was).  Not because he was unlikable (even though he was).   Not because he was a boundaries-pushing Chester Molester (he was).  

       I dislike him because he took advantage of my trust and my lack of experience and he cheated me out of my fee.  Successfully, which made it all the more humiliating and frustrating.  

        It’s an awful feeling to be scammed or ripped off, and know there’s nothing you can do.  It’s like being violated.  

        I was just starting to work independently outside the dungeon, and I had yet to learn one of the principle rules of the Biz–or any sex work: get the money up front and count it and hide it.  

         The doctor–let’s call him “Chester”–taught me that lesson.  

         I was terrified of being arrested, and thought that I was protecting myself by not asking for money.  Most clients know how the system works and would just leave an envelope on the coffee table or the bathroom, where I’d see it when I arrived.  A few waited until the end to pay me, which was always nerve-wracking, but they always came through before I left (a few of them wait till the end because they’re distracted and they forget.  But some are jerks who intentionally hold the money till the end in order to enjoy stressing the woman out and making her sweat.  They like to keep the power and make her worry.  It’s not nice at all.).

            Chester didn’t pay up front, but I thought it would be safe because I’d never been ripped off before, and it was obvious that Chester was a man of means.  He was a physician and a teacher with a successful practice and when I checked his apartment address as part of the screening process, a 1-bedroom apartment in his building was for rent at $3800/month.  Chester’s gorgeous apartment was 3-bedroom, so it’s not like I had any reason to believe that he wouldn’t have the ability to pay my fee.  

          I put some work into Chester prior to sessioning with him, too.  Like I said, I was just starting out and I let a lot of time-wasting clients…waste a lot of my time.  Chester was a control freak who wanted me to session with him and his wife, a switch session, and I got the feeling that he was trying to vett me so that I was “the right one” and wouldn’t make his wife uncomfortable, which seemed reasonable to me. 

         Now, though, I just think he wanted to discuss session ideas in detail because it was free sexual attention from me.  Le sigh!

         Via e-mail, we hammered out the plans for a 2-hour session at his apartment.  I was going to be dominant most of the time and submissive for maybe 30 minutes.

          What did my decent, unsuspecting, rookie ass do…?

            I fucking offered him a discount. 


            See, he’d contacted me through my switch/masochist ad, and when I sub professionally, I charge much more then when I’m a domme.  

            Since I wasn’t going to be dominant for most of the session, though, it seemed UNETHICAL of me to charge him my full submissive rate…so I charged him my domme fee for the first hour!  I offered it!  It only seemed fair!  I was just trying to be an honest businesswoman!  

            Doing this probably gave him the impression that I was vulnerable and an amateur.  If he was a decent human being, he would have been impressed or touched by the gesture, or at least appreciative of it.  But he wasn’t, as we shall see.  

          I just tried to be honest, and he ripped me off anyway, and that makes me even more angry!

          We confirmed a price.  It was agreed upon, explicit, laid out.

           So, I got dressed and packed my bag and went to meet Chester and his wife on the UES.  They wanted to meet me in public first, which is always fine with me.  It helps set me at ease if I get the opportunity to assess them first.  

           Well, I got to the restaurant on the corner and went in to meet them in the bar, and…

          ….it was just Chester (ChesterLie #1!)

          ….Chester did not match his photos or physical description (ChesterLie #2!)

           As I have said many times on this blog: I do not care what my clients look like.   I don’t care, don’t care, don’t care.  The only thing I care about is that they are clean and groomed, and if their feet are gross, it would be awesome and appreciated if they’d keep their socks on.  I have had many excellent sessions with plain-looking, or even homely-looking men.  Heck, in my private life, I’ve fucked plenty of ugly guys.  I don’t care!

          But this guy told me that he was handsome.  Repeatedly.  “Very handsome” was the exact phrase. I was not impressed by this claim, but I was expecting a conventionally attractive individual (and keep in mind, I like nerdy-looking guys.  I think a man can be very good-looking and not be, you know, Jude Law or Antonio Bandaras or whoever).  

         The only woman who would find Chester “very handsome” would be his mother.  And this was not a case of “Handsome at 35, but age has taken this natural toll.”  He was average at best.  

         Which is fine!  I only mention his physical appearance because he did!  He bragged about it!

         Chester…was a narcissist. 

         Chester told me that he wanted to meet me first, without his wife, to make sure that I would be a good match for them.  He didn’t want to upset her, he said, by bringing the wrong woman into the house.

       I immediately pegged him for a lying cheater (oh, if only I had the same sense with the Mathematician!).  

        Why’d he lie?  I don’t care if my clients are married!  I’m not having sex with them (and even if I was, I still wouldn’t care)!  Why lie?  Why lie to a sex worker?  It makes no sense.  

        We chatted.  I couldn’t exactly call him a liar, but I tried to feel him out.  He was nervous.  Clearly, he was cheating on Mrs. Chester.  I doubt he ever discussed me with her.  But…he was safe, obviously very white-collar with a lot to lose by seeing me.  I knew the type.  They can be pricks, but they are almost never physically violent.  They are paranoid and scared to death.  

         We went up to his apartment.  I followed him three minutes after he left–we went up separately.   Like I said: scared cheater.

        The scene in his apartment was something else.

         Chester lived in a high-rise and the glittering lights of Manhattan were laid out underneath the floor-to-ceiling windows.  There were two folding tray tables laid out with a bunch of really weird, expensive, obscure S&M gear.  I’m talking thousands of dollars worth of stuff.  I know good equipment when I see it.  

         There was weird European porn on the projector, and he had a surround-sound audio system, so the talk and sex noises sounded like they were coming from all over.  It sounded like there were other people in the room. 

         He asked me if I’d like a refreshment.  I asked for a bottle of water.  In my email to him, I expressed that I would only drink from AN UNOPENED BOTTLE.  

         He brought me a glass of carbonated water (Chester Lie #3).

         “Sorry, but I can’t drink this,” I said.

          “Why not?”

           I stared at him.  “You work in a hospital.  You have access to drugs.”

           “I would never do that to you.”

           I went and got some water from my bag.  

            Chester got dressed.  Get this…remember that gimp from Pulp Fiction?  That studded leather bodysuit with the hood?


             At first, it looked so ridiculous that I was biting the insides of my mouth trying not to laugh.  It was so fucking funny.  I mean, here I am, in this luxury high-rise with this sex maniac doctor in his gimp outfit and weird Euro porn all over the wall, and all of this ODD sexual equipment on the tray table(s).

            I knew that he had to be a surgeon because everything was immaculate, and when I washed my hands prior to session, he told me that I “did a good job.”  

          After about an hour, though, the doctor didn’t look so silly in his gimp suit.  

          He started to look weird as hell.  Not frightening, just…creepy.  

           I knew what I was looking at: a sex addict in thrall to his addiction.  He was in an obsessive place in his mind.  He wasn’t present with me, engaging.  I was just a prop.  I was never scared that he was going to rape or assault me, but I was acutely aware that he stopped seeing me as a human being once the session started, and the weirdness of the scene stopped being funny.

        I was trapped in the Haunted House with Chester.  Welcome to Chester’s Haunted House!

         And he kept pushing, and pushing…he’d back off, but even though I was the “domme,” I’m telling you, I was in the submissive role and I should have earned submissive rates for that session.  I know the difference in the emotional labor I have to do.

          I managed him and got through it.  He came down.  Or, more accurately, he came back.  

         The porn was turned off, the lights were turned on, and Chester changed into street clothes.  I changed and gathered my things.  I was mentally and emotionally drained, and I just wanted to get my money and go home.  

          I earned every red cent.  If I’d known what I was in for, I would have charged that man $1000.  Our agreed-upon fee was $600.  

          It didn’t work out that way.

           TO BE CONTINUED


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