Monday, August 2, 2010

Day 3 windy city...

Sorry took me a while to post the last day in the windy city.... So as promised my last hook up on day 2 kept his promise and got in touch on day 3. Before we get there though..... worked out in the hotel gym in the afternoon and there was only one other guy in there. He was an older guy, very good looking and kept making eye contact. Hmmm.... OK. I figured I needed to work out though so I kept lifting. He stayed working out as long as I did though. Funny thing.... Ha, not! So when I finally go to leave I walked by and smiled and he smiled and decided he was done and so...he left too. He caught up with me at the elevator and started talking to me. He asked what I was doing there and I said I was on business. Him too. Where are you from, blah blah blah. Then he smiled again so I figured I should cut the crap. Did you want to come back to my room for a bit? He smiled and said sure but should he shower first? I said do you think it's a waste if you just get sweaty again? He laughed and said 'wow you're direct.' I said sometimes and so we both went back to my room. As soon as we walked in I grabbed at his shorts and we started making out. He said he was paranoid about sex because he didn't have rubbers with him. He was married and asked if I had rubbers. I said no but it was OK. I asked if he just wanted to get sucked off instead. He said sure so I got on my knees and started polishing his knob. He moaned as soon as I took it all the way down. Average size and average thickness so real nice to suck deep. He asked if I liked it and I said yeah and I asked if he liked it and he said oh yeah. You know that great feeling when you blow a guy and you can feel it swell and harden in your mouth and you know what is coming next? Man I love that feeling.... So sure enough he shot a load in my thick and so tasty. Oh man it was good. Then it got weird for him and he said thank you thank you very quickly and pulled up his shorts and said he had to go. Um ok. I asked if he wanted something to drink or anything and he said no no, he was good. OK then, I got what I wanted and so did he so buh bye....

Then I washed up and sent a text to Day 2 guy. He said he couldn't come to me that night and asked if I wanted to drive to Boystown. Give me 5 minutes to get my car ;) I was there in 20 minutes and got parking right in front of his building. Unheard of!! Meant to be.. He buzzed me in and met me at the bottom of the stairs. We walked up and went to his apartment and sat down. He asked if I wanted a beer. Sure. Then he put on a movie (not porn) just a movie so we could hang out. We watched about 20 minutes and then started making out. Then he pulled his shirt off and then pulled mine off. Then the shorts (his then mine) and we thought maybe head to the bedroom. We got on his bed and started making out. He rubbed my crotch and then we started to blow each other. First one after the other, then we got into a nice 69. After a few minutes he wanted to fuck. He also said he wanted to flip. NO worries. He slipped it in and started fucking me. It was almost a repeat of the night before but without the photos. He didn't take more than 5 minutes doing it doggy all the time before he came in me. He decided he wasn't sure if he was clean and maybe we shouldn't fuck (me fuck him). I think it's because I wasn't 100% clean. So we showered and then he asked if I wanted to spend the night and just cuddle. Sure... so we get in bed and start cuddling, spooning, etc. We kiss some more and drift off.

It got soooooo hot in the bedroom, he had a fan on but the AC was off so I started to sweat. Then I was awake and his butt against my front made me start getting hard. I am thinking well since I am up and now he's showered and he went to the bathroom and everything, let's give it a whirl.... So I grab a little grease by the bed and lube my dick and his hole and slowly push in. He's asleep but quickly wakes up and starts getting into it. He starts the 'yeah, fuck my ass' chant a couple of minutes into it. Now I don't top that often anymore since I LOVE getting fucked but I used to do it all the time. Just out of practice. So sometimes I get performance anxiety but I keep it together long enough to tell him my load is coming and I manage to squirt a nice respectable load up his hole and then we collapse in our own sweat and fall back asleep making out. It could not have been more than an hour later his alarm starts going off and he asks if he can fuck me again. Hell yeah! So his wake up exercise is to do me a second time. His first load is still in my hole and it is still slippery so he needs no lube and slides right in. Again, it takes him just a couple of minutes and he drops another load in me. We kiss some more and he thanks me for spending the night. Then I tell him I will get out of his way so he can go to work. I head back to my hotel about 5 AM and sleep for 3 more hours before getting up and doing my last meetings and heading home. I made a new friend and I hope we fuck next time I come out again!

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