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Originally I was not going to go out on Friday night.  I was looking forward to a nice night home, alone.  Well, that all changed when Jim called me.

I met Jim a few months ago, he is a new kid in town.  He just graduated from school in NYC and moved to Chicago for a job as his company is based here.  We’ve been in touch through texts and email, but had only hung out when we were both at happy hour at our fav bar.

So, Friday I meet him around 6:30pm at our fav bar and we have a few happy hour drinks and some apps.  It probably would have been smarter to plan a dinner in there so we didn’t get so wasted, but of course we did not.  We finish up happy hour there and were thinking of the next place to go and drink some more.  Jim suggested this bar that overlooks the lake, which while I love this place, we’d never get a table at 8pm on a Friday night.  I had a better solution though, my balcony overlooks the lake (well, with a building kind of blocking 1/4 of the view) and we could pick up a six pack, drink there for a bit and then meet out friends out later on.

We did just that and we actually talked quite a bit.  It was fun getting to know him and learning about his stories.  I found out he was only 22, oh my.  He looks and acts so much older and he is a mechanical engineer and has a job at a very prestigious company and I seriously thought he was maybe 24 or 25.  Jim is also kind of a cutie, in a not my traditional type kind of way.  He is about 6’2, is Irish looking with light hair, blue/green eyes and freckles but he is cute.  He is kind of a bigger guy, too, not fat just bigger, husky.  Totally not my usual type.

Jim is am amateur photographer and took a lot of really cool shots on the balcony and also a lot of portraits of me.  That was kind of fun.

After we drank the beers he said he wanted to see live music somewhere and did I know a place.  I texted a few of my friends, one that works for a record label, to see what was going on.  There is always live music in Chicago.  My friend Will got back to me and put Jim and I on the guest list to see this local band and some national band, too.  Jim took a lot of pictures and we both drank more beer.  We danced and had a really good time.

All of a sudden I get tapped on my shoulder and turn around and there is an ex-boyfriend of mine from… 2003, maybe?  I have not seen him or heard from him in years.  Apparently, he now lives in the Bay Area.  It was nice to see him but somehow what happened next, I have no clue.  Jim was chatting up one of the guys from the opening band, and I told him I was going with Greg, my ex, to meet his friend (my old friends).  Well, Greg and I really found a corner and started making out? What?  Why do I get drunk and do stupid shit?  I mean, he did look hot but in no way, shape or form do I want to do it with him, be with him, miss him, etc, etc.

I figured I was away too long so I went back to where the band was and hung out with Jim some more.  He ran into some people he knew so it was fine that I would leave and what not.  I went to the bathroom and Greg followed me in.  It was a smaller club with 4 single unisex bathrooms so we went it and we started making out heavily.  He pulled down my tank top and started sucking and biting on my nipples as I was kissing his neck, biting on his ear.  I admit, I was getting very excited and very wet.  All of this is going on as I am being pushed against the bathroom wall, which was kind of exciting, actually.

I decide we are being rude to people in line, but I also did have to pee, so I peed in front of him, um and he started making out with me, while I was peeing?  I know it sounds weird, but it was more about being drunk than anything else?  We left the bathroom and went separate ways.

At this point I was so drunk (I actually started drinking water) and it was about 1:00am and I just wanted to go home.  I got Jim and said it was time to go, he agreed.  He only lives a few blocks from me so we got into a cab together and went to my place.  We decided to hit a late night happy hour to help us sober up a little bit.  Thank goodness, I needed it.

We get ready to leave and he asks if he can sleep at my house.  I am so turned on from my dirty bathroom make out session with Greg that I think, yeah, I might be into that.  Then he whispers into my ear – don’t think I am looking to fuck you, I just want to lick your pussy.  OK, yes, you can definitely come home with me now!

We walk in the door and Jim went in to pee & use mouthwash and what not.  I had to pee so I went in next and while  I was there I washed my face and brushed my teeth in there – and took off all my clothes.  Why did I do that, not sure, but it seemed to go over well.  By the time I walked out of the bathroom Jim was in my bed.  He seemed very excited that I was not wearing any clothing.

Immediately I got on top of him, he was still wearing boxers and we started making out.  He is kind of bossy in bed, it was kind of hot.  While we were making out he put my hand down towards my pussy and told me to rub my clit while he started licking my nipples.  Then he slowly moved down my belly and started giving me kisses around my belly, my thighs… all the while telling me to keep rubbing my clit.  After about 5 or so minutes he started licking my clit.  He was pretty good at it, he kept his concentration on rubbing the tip of his tongue on my clit.  I came pretty quickly and I pulled his head away and he kept on licking, long strokes with his tongue.

So, after that happened he basically was like, OK, I am going to bed now.  I was ready to let him fuck me, and I offered but he was like, no, maybe next time we see each other.  Whatever, I had awesome oral sex, I was good.

Here is a weird thing though, he spooned me all night long.  I mean, all night.  I would wake up because he was pulling me back toward him.  I hope he is just a cuddlier and this doesn’t mean something more.

I did wake up Saturday morning, naked, and it took me a minute to remember who I was with… I thought did I take Greg home?  Yeah, that’s bad, I know.

One Response to “Friday Night”

  1. […] again. I say again because this is not the first time I’ve recycled with this particular ex before. This time it was a bit more planned out and less random. See, Greg moved out to San Francisco a […]

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