Saturday night I met up with Janey and one of her old work friends (Julie) that moved, but happened to be in town. We put on dresses, got a bit glammed up and decided to head to this wine bar, that was new to us, as we had not been there before. We left about 10pm and one of Jane’s friends was planning to meet us there later.
OK, rarely do I say where I am at, or what bars I frequent. I mostly do this because I go to the same ten or so spots in my neighborhood over and over again. In addition, I do not want my friends, or more importantly my co-workers, to catch on. Though, I figure every now and then it’s OK for me to say where I am/have been, especially if it is a place where we (Jane and I) are not regulars and it was just us out, not our other friends, too (i.e. if any of my “real” friends happen to read this, they will not catch on.) Oh, and Janey knows about my blog now, my drunk ass could not keep it a secret. That’s OK, she is sworn to secrecy.
So, having said that, we were at Rootstock Wine & Beer Bar. It was pretty busy but two guys were leaving the bar. There was also an open seat on the left of this man that was also sitting at the bar. I was immediately excited because he was very good looking, and dark – my favorite. I asked him if he would mind moving down so the three of us could sit together, of course who says no to that?
He was alone and I sensed he was not from here. I was correct. It turns out his name is Shaun and he comes here quite a bit for work, as his company is based here. He was staying at his company’s corporate housing which was somewhere up by O’Hare, so I have no clue why he was in Humbolt Park. We probably talked about it when he was drinking, but I don’t recall.
I ended up kind of talking to him quite a bit because Janey and her friend had chatted up some other random dudes. He was pretty funny because within the first ten minutes he made it clear he was divorced and he dates white women. I replied with, um, of course you do.
Shaun was super good looking though. He’s about 6’1 or 6’2, light skin, nice build, nice smile, and just had a very cute face. No, hot, he was hot. I could tell he was a bit shy because I was kind of carrying the conversation more than he was, but the more he had to drink the more he was coming out of his shell.
We were talking for about an hour, and then it got to the point where he bought a bottle of wine, asked for an extra glass for me. Janey & Julie’s two guys left and they joined our conversation, in which the main topic was at what point is it too early to introduce anal sex into a relationship. Wow, these girls do not hold back. Julie also was tipsy and started talking about how hot it looks when chocolate skin held against milky white skin. Yeah, I was a bit embarrassed.
At some point he was playing with my hair? That’s when I knew he was going to come out with us for the rest of the evening.
After staying at Rootstock for about two hours, Jane’s friends finally showed up. They had one drink then we all moved on to the Clipper, another place I had never been, and had a few more drinks. Of course I convinced Shaun to come with us for the rest of the evening. He was very happy to accompany me, especially since Julie told him I was a wild woman in bed. Yeah, so embarrassing.
We managed to get a booth at the Clipper and I scooted in and Shaun got right next to me. He put his hand on my leg and it kind of excited me. Janey’s friends got a bunch of these grape soda drinks, as they said we must try them, I guess it’s the specialty drink at the Clipper. Oh my, so good. It’s a bit sweet, so I could not drink more than one but it was really good. After that Shaun made sure my drinks were full, Jane’s and Julie’s, too. It’s all pretty much a haze from here. There was a jazz band, Julie was making out with some older (like 50 +) guy, Shaun was rubbing my leg, holding my hand? Jane started ordering shots?
It was approaching closing time, but none of us were ready to call it a night. Someone mentioned we were right by the Continental and maybe some dancing was in order? As we were walking there I kind of remember Julie & Jane telling me that Shaun was a good person, they liked him, etc. I am not sure where he was at this point, for all I know he heard them talking. I also remember saying to them I was not taking him home with me, or if he did end up at my place, I was not having sex with him. I said something like I really liked him and I wanted to see if it would go further or something? Who knows, I was pretty plastered. I also remember telling Shaun that I would not be sleeping with him. He said something about how he did not expect me to, but he would like to sleep over and rub my back or something, then take me to breakfast tomorrow? Oh my.
We head to the Continental (Hey, Continental, get a real website, I refuse to link to a Myspace site!) It had been awhile since I had been there, and come to think of it, I’ve never been to the Continental sober. I decided no more drinks for me. Janey & Julie were still going strong and I think Shaun might have had a drink, too.
Shaun and I decided to dance a bit. Oh I LOVE dancing with black men. We were getting a little dirty, too, his hands were grabbing my ass, I started kissing his neck and eventually he kissed me. Then there we were, making out on the dance floor, which I usually loathe, but funny how drinks can change one’s mind.
We stayed at Continental for about an hour and then decided it was time for late night food? Julie, Jane, Shaun and I piled in a cab and headed back to my neighborhood. I guess it was a given he was sleeping over at this point. We went to this all night Mexican place kind of by my house and ordered so much food. Janey does that when she gets wasted, just orders a shitload of food for the table. Julie was sitting next to Shaun and he was giving her guy advice, I think. Janey and I were talking to these two guys were kind of know from the neighborhood.
Janey and Julie took a cab home (um, it was 5 blocks, are you kidding!) because it was “too cold.” I told Shaun I wanted to walk the 5 blocks, as the Mexican food was bubbling in my stomach. We got home and literally went right to bed. I did my night time stuff, wash my face, brush my teeth (gave him a toothbrush to use), put on a cute (but not revealing) night gown and crawled into bed. He was wearing just his boxers. I kind of wanted to play with Shaun a bit, but was so tired. We made out a bit, we wrestled in the sheets, I got on top of him but that is about it. I could feel his cock rub against me and I could feel it was so hard, but I could not stay awake. So, we passed out and set the alarm for 10am and planned to go to brunch.
Little did I know, I was going to have a hard time getting rid of Shaun. Ah, more to come.
Oh, and I want to apologize to @TankBoy, who sometimes DJ’s at the Continental. One of these days… 
