The Gangsta

The Gangsta gets his own blog post for a few reasons.   He was one of the first guys to message me on the dating website after I set up my profile.  He's 21 and said he wanted an older woman to teach him stuff.  Ok.  I can do that.  Secondly, he is the cutest, most pain-in-the-ass boy I haven't even officially had actual sex with yet.

The story begins with the usual few messages on the dating website until we very quickly switched to texting.  Almost every single night he would text me and we'd have long involved conversations about what we wanted to do or not do.  He immediately had me laughing to myself at his audacity to just blurt out certain things or offer me advice that I'd obviously not need from a 21 year old.  (just get on birth control!) All of our conversations were alternately hot, interesting, adorable, or flat-out entertaining.  We both agreed that we had to meet soon.

Now the thing is, when dealing with guys that young, you are sometimes confronted with things like "I don't have a car", "I don't have bus money this week", or "I can only meet you at 5:30 in the morning"....adorable!  Several times he texted me in the wee morning hours ordering me to call in sick so we could fuck all day.  Adorable!  Audacious!  Ridiculous!  (no I never called in sick to meet this guy)

One day he agreed to meet me on a Sunday and "fuck me all day", something he'd been promising for quite some time but still hasn't come through.  I said it might be fun if we drank or at least did a couple of shots so I asked what he'd like to drink. 

Peach Ciroc.

Really?  Now kids, keep in mind that Ciroc is P-Diddy's brand of vodka.  This is why he earned the nickname "The Gangsta" because all at once, he thought he was some kind of hip-hop star wannabe while at the same time favoring a drink that is very much NOT gangsta!  So I bought him a bottle of Peach Ciroc.

He never showed up.  That bottle is looooong gone, having been shared with another guy who shall have his own chapter much later in the program.

Now, The Gangsta also had some fantasy about meeting me in the woods and taking a walk on some kind of trail late late at night.  I told him no, I'm a grown woman and I have my own place so there's no need to fuck in the woods like a teenager!  I actually finally gave in and agreed to this a couple of times, but it never happened for one reason or another.  I went back and forth about whether or not I'd meet him like this and he continued to refuse to simply take the bus to my place.

Argh!!!

Yet I still kept on with this kid for some reason...he had some kind of hold over me.

Finally, one day I agreed to meet him as we both agreed it was time.  Keep in mind we'd been communicating for about a month at this point and it was getting pretty ridiculous.  So one evening he texted me an intersection north of downtown.  I took a cab there around 11pm and found myself deposited in a very dark corner park.  He was nowhere to be seen.  I texted him and he assured me he was on his way. 

Finally I saw him walking towards me in the darkness...he walked up and kissed me.  
After I let him know I didn't appreciate waiting for him alone in a dark park, we walked around and found a relatively secluded spot.  There was groping, his pants came down a little bit, my top got pulled down...this was as close as he was gonna get to his fuck-you-in-the-woods fantasy, without the fucking.

We ended up on the swings where we talked for quite a while.  Nice kid, actually, but he was too busy trying to live up to some playa image he had of himself. 

When it was time to go, I called a cab but they would not pick me up at an intersection; I needed to be at an actual address.  The Gansta walked me to a nearby store where he waited with me for a few minutes and then walked off to meet his friends, leaving me there!  1:00am in a store parking lot!  By myself!

Since that night, he has texted me on and off, usually in the wee morning hours, but other times too.  Recently he texted me late one night saying he was super drunk and would I call him?  Well I was drunk too so I did call and we talked for quite a while.  

He still has not found the time to make it to my house, but I feel like it'll happen eventually.  I have no idea how good it'll be, but at this point I don't care; I just want it to happen.