Ultimate test of sex skill: Getting free sex from a hooker

Challenge:  Hire a hooker for one session.  By the end of that session, make her ACTUALLY enjoy the sex.  Then create an arrangement to continue having sex either for free, or in exchange for lessons in sex, kink, or English.

Challenge accepted.  Found an asian $160/Hour on backpage who happened to live two blocks away from me and could host.

  1.  First I made sure the session wouldn’t be a complete rip off.  First over text and then again on arrival BEFORE handing money over, I asked, “Does an hour actually mean an hour?”  “45 minutes with 15 min break inbetween” she responds.  That’s fine.  Some of them will try to say 5 minutes is an hour because it’s “full service” and won’t even bother making you cum.  Some preemptive statement can really improve the quality of her services.  “BTW I live down the street and if you’re nice to me, i’ll come by more often”  Ham-handed, but hard to ignore.  Then I said if she’s nice i’ll give her a little extra in the end.
  2. Hit her with some cocky funny right off the bar as I undressed.  “Hey aren’t you glad i’m not some old fat dude…and…check it out i’m shaved!  How often do you see that?”
  3. “I shaved too” she said.  It was an even funnier joke when i realized she was not, haha.
  4. Was very nice and respectful.  Always asked before touching her or doing something.  My first request was if i could give her a backrub.  At first she thought i was asking for one.  “Oh, you gave me!?!? hahah ok!” Then she yelled out to her colleague in the next room in Mandarin, that i wanted to give HER a backrub.  I explained that I love to rub beautiful bodies.  She was fucking stunning.  a 10.
  5. I attempted to connect to her inner true submissive, rather than the motive of contracted labor.  I kept asking her to do things, simple things, she kept complying.  No bj withouth a condom? Fine!  How about you kiss my balls?  She did it.  When she would legitimately impress me wit her calibration and sensitivity to my wants, I would say “Good girl!” , and she would giggle.  There’s usually a D/bg turn on lurking in there somewhere.  She even let me lightly spank her, and lightly hold her hair while fucking her doggy!  Standard price for a pro sub is $1000 an hour I believe.  I always asked first and said “Can i gently do X”?
  6. Sounds crazy but I planted a few seeds of an emotional connection.  “What’s your name” I asked while fucking her missionary.  “Oh Taiwan?  So Mandarin then? while i was fucking her doggy.  She was tiny and I checked in a few times to make sure I wasn’t hurting her
  7. Kept testing the limits further and further getting her to do things that almost NO standard priced hooker would ever do.  She agreed to let me switch positions.  She agreed to let me touch her as I pleased.  Get this, SHE KISSED ME!  Yes she allowed me to kiss her whenever i wanted.  This is when I noticed it without a doubt(i think)                                                                                                                                                                                                                  She was digging it!
  8. Guess what, no 15 minute break.
  9. Asked her if she’s into rough sex.  “What is…rough sex?” she asks.  At this point i started to suspect that she was faking her off-the-boatness.  She accidentally said one word with a near perfect American accent.  lol.  I told her, spanking, slapping, biting.  “No she laughed”  I told her she could make 5 times as much money doing that, and she wouldn’t even have to fuck guys.  She seemed genuinely interested.   I then asked her to gently slap my face.  She laughed and made the most half assed attempt to do it.  She was pretty uncomfortable with the idea.  Man how can a professional sex worker be SO fuckign clueless about sex? At this point it’s becoming clear that I was one of the best John’s she’s had in a while.
  10. She was making no complaints about time.  Usually hookers rush you, especially since we were nearing the 45 min mark.  I told her to let me know when she wants me to finish, because I could go on for hours.  “Really!?” she responded.  “So you have control?”
  11. Amazingly, i kept fucking her and moving her around and making her do this and do that, for another 20 minutes and not one complaint to ask me to wrap it up.  Though she was beginning to look a little anxious and not into it.  Her colleague knocked on the door at one point.  This was clearly a planned gimmick.  She ran out and came back in, and said her ‘parents’ were coming over.  Haha yeah right.  But she happily continued letting me fuck her and order her around.  I wasn’t really doing a dom role.  I was being sweet and nice.  I was complimenting her skills and how nice she was being.  I actually decided to anounce the ending cause i felt bad for her.  I could tell she felt uncomfortable making me stop.  This is UNHEARD OF for a hooker.
  12. I asked her to look at me while I came.  This is a request I always make and sometimes cause girls to have SCREAMING epiphanies, never before realizing what a meta-orgasm was.  In this case it was a bit too much, she couldn’t maintain eye contact for long.  Of course not, that’s an intense emotional bond.
  13. I scream like a maniac when I cum.  I sensed by her bodylanguage that this might blow up her spot with her neighbors.  I toned it down.  She kept sneaking smiles that, at least to me, clearly expressed “Wow, you’re different”
  14. As I was getting dressed I told her a bit about professional Femme Dommes.
  15. I tipped her $20 extra
  16. AS I was finishing getting dressed, I called her out on pretending to not speak English.  I did it in a playful, friendly , “Pretty slick, but i gotchya” sort of way.  She literally looked at me smitten for a moment.  Women really admire when one men in a thousand are actually observant.
  17. As i was walking out I made the pitch.  I offered to trade English lessons, and lessons on how to perform kink, in exchange for her services.  I made it clear I was serious about this, and she could become a much more highly esteemed professional.  “Just think about it ok?” I said as i walked away.  We parted with a handshake.

Note: This post is dedicated to a certain birthday girl today.

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