As I approach another birthday, and reflect on my life, I also realized I am coming up on the 4 year anniversary of my first time in the "hobby".  Needless to say, it has been a wild and exhilarating ride, while I also encountered a few bumps in the road.  Just thinking back on one my of amazing recent encounters, I realize I have come a long, long way from my first time.  Thank God for TER which finally set me straight.  So I started wondering, how does my first time compare to other hobbyists.  I am also curious how some providers might describe their first time.  Come on NY TER, care to share the Good, bad or the ugly.  I will start...  And yes, I made EVERY rookie mistake there is.  I count my lucky stars I was not horribly ripped off, extorted or busted by LE.  And yes, I am using an alias for this one.    
   
 I was on a business trip to Chicago, had been wandering the NoSex desert for quite some time and I just couldn't take it any more.  Despite it being freezing cold, I was pretty much walking around with a permanent hard on, and taking care of business myself just wasn't going to satisfy the urge.  My options were limited.  At that time, Craigslist was getting a fair amount of press, so I decided to check it out.  Sure enough, lots of smoking hot women to chose from.  
   
 So after about 20 mins of perusing CL, I came across an ad with a picture of this gorgeous looking Eurasian looking babe in a bikini laying on the beach.  Ding, ding, ding, we have a winner.  So I pick up my (work) cell phone and call the number.  No answer, bummer.  Ok, keep looking.  A few mins later, my phone rings and it's her - awesome!  So I say, " Um, hi, yes, I saw your ad on CL and was hoping you could come over."  The conversation was a bit awkward, but she tells me $200 for an hour, and she can be there in 30mins.  I say,"great, I am at XYZ hotel in room 1234, see you in a half hour."   I hang up my phone and think, holy cow, this CL thing is amazing!    
   
 I end up running across the street to the ATM and withdraw said $200. I run back to my hotel room, hop in the shower, brush my teeth, etc, and throw some clothes back on to get ready for my big date.  My heart is racing and I am sporting a raging erection.  I sit on the bed twiddling my thumbs waiting for her to arrive.  30mins go by, nothing.  45 mins, I call and no answer.  Uh oh, maybe something happened.  1hr later and the phone in my room rings.  Huh?  "Good evening sir, this is hotel security in the lobby, you have a visitor here to see you."  OH SHIT!!!! I didn't realize after a certain hour the hotel went into lock down.  I politely tell the security guy, "ok, I will be right down."  So I get down to the lobby feeling totally uneasy at this point and lay eyes for the first time on my date.  Needless to say, she looks NOTHING like the picture.  Not even the same race.  She was more a cross of Latin and African.  Not terrible looking, maybe a 5 or 6, but a far cry from the woman in the ad.  Given I am down in the lobby, the security guys are looking at me with that dumb smirk indicating they know exactly what is going on I make a split decision.  "Hey Hun, how are you?  You're late, let's head on up stairs."  We turn around and head up the elevator.  
   
 When we get up to the room, she asks for the money.  I open my wallet, pull out the $200 and hand it to her.  Of course no envelope.  You are probably wondering at this point is she proceeded to count the money out in front of me.  Come on, you know the answer...  Once the business side was taken care of, she excuses herself to the bathroom.  After what felt like an eternity, she comes out in her bra and panties, and that was when I realized she had a lot more junk in the trunk that had been covered up by her winter coat.  Oh well.  She then comes up to me, tells me to strip.  No kissing, no touching at this point.  So I strip down (her bra and panties still on) there is some bad LFK that follows.  She then lies down on the bed and tells me to get on top of her.  Yes, let the dry humping begin.  After a few minutes of bad dry humping, she says "bring that cock up to me." Great, I am finally going to get some action.  So I straddle her face and she takes me in her mouth for BBBJ.  It was actually quite good, and given my heightened state I have no control.  One Minute later,  and with no warning, Kilauea erupts!  Needless to say, I had no idea CIM was not on the menu.  She pushes me off her, goes running to the bathroom to spit out and rinse.  She comes back out and yells, "ya know, you're not supposed to do that!!!!"  "Ummm, I am so so sorry, I really did not mean to, was a total accident."    
   
 So at this point, I am a little bummed and feeling like a HS premature ejaculator.  But then I remember I paid for the hour, so I will get another shot on goal.  When I approach my date about another round, I am told, "honey don't you know how it works?  You cum, you done!"  She does eventually offer me another round if I am willing to give her another $100 bucks!  At this point, I say no thanks.  She goes back to the bathroom, gets dressed and walked out the door.  There ends my first time in the hobby.    
   
 It took me a very long while to try again.  Luckily I found TER, started to learn a few things.  Moved up from CL to Backpage, lol, and started to have much better experiences...  
   
 Hope you enjoyed my story, and hope others will share their tale.  
   
 Happy Holidays everyone!

-- Modified on 12/10/2013 9:54:39 PM