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Second night in Chicago

After the first night in Chicago I wasn’t sure I was going find much more excitement. But I was on Scruff chatting with some guys. There was a particularly hunky guy that I was chatting with. I was telling him about my trip so far and he thought it was really hot. He sent me some xxx pics and asked if I wanted to come over and jerk off for him. He was really sexy and I thought what the hell. I was leaving town the next day and I would never see him again.

I took an Uber to his place in Andersonville. He told me the address and gate code. He told me to buzz myself in and come up to his condo. I knocked on the door and my nerves hit me all at once. He opened the door and was super sexy just like his pictures. He was still dressed from work. He had on slacks and a white dress shirt. He told me to come in and asked if I would like a drink. I told him no thanks and he led me into his den. He poured himself a scotch and then took a seat in a big leather chair. He loosed his tie, undid the top button on his shirt and leaned back. He told me to take off my shirt. I did as he said and then he told me to drop it on the floor. He told me to unzip my pants and pull my dick out. I was already getting hard and did what he told me. He told me to look at him while I got my dick nice and hard. I stroked my dick will his sipped his drink and smiled.

Once my dick was really hard he told me to drop my pants around my ankles. I pushed my pants and underwear down to my ankles and kept stroking my cock. He told me to take off the rest of my clothes and I followed his orders until I was totally naked. He watched me stand in front of him and jerk off for quite a while. I could see his boner in his dress slacks. He told me to come over to the chair and get his dick out. Without even thinking about it I did what he asked. I had seen a pic of his cock but know I wanted to see the real thing. I got down on my knees in front of him and unbuckled his belt, unzipped his pants and then pulled his cock and balls out of his boxers. It was a good fat 7 or 8 inches. He told me to jerk him off. I stroked his dick while he stared at me.

Once he was really hard he stood up and slid his cock into my mouth. He told me to relax my neck and then he grabbed either side of my face and started to slow fuck my mouth. I wasn’t sure if he was just gonna dump a load in my mouth and send me on my way or what. He fucked my face for a while and then pulled out. He told me to follow him and walked toward the dining room. I follow him in and he walked to the end of the table and motioned for me to come to him. He turned me to face him and then lifted me up and sat me on the table facing him with my legs swinging off the end. I noticed that he had already set a bottle of lube on the table. This must mean he had this more thought out than I thought.

He sat down in the chair facing me and told me to jerk off for him with the lube. I grabbed the bottle and squirted some in my hand and started stroking my dick. He leaned back and watch me put on a show. I was getting really horny and he was enjoying the show. He told me to play with my balls while I jerked and I did what he asked. He told me to scoot back a little and put one foot up on the table. I did what he asked and when I lifted my foot up and put it on the table I could feel my asshole become a little exposed. I was hard to have my foot up and keep jerking and playing with my balls. I could tell that he was looking right at my asshole and he leaned forward in his chair. He picked up the bottle of lube and squirted some on his finger . He reached up and started making little circles on the outside of my hole. It felt amazing.

He played this game for a while until I was moaning. Then he told me to take over playing with my butt. He leaned back and watched for a while and then told me not to stop. He then got up and walked out of the room. I was super horny and kept doing what he had instructed.

When he came back in the room he was completely naked. He had a solid fury body and that big dick was bobbing in front of him. He asked me if I wanted him to fuck my ass or mouth. I had just met this guy and was not about to let him fuck me. But the slutty side just answered mouth. He told me to get off the table and led me into his bed room. His bed was really tall and he told me to climb up and lay on my back with my head towards him. He stood at the edge of the bed and helped me scoot back until my head was hanging off the bed and I was looking at him upside down. He told me to keep jerking off but not to cum until he told me to. He stepped closer and opened my mouth and slid his cock in and down my throat. He started the same slow throat fuck that he was doing in the den. He started talking dirty and told me to keep jerking my cock for him. He talked about using my mouth as a fuck hole. And that I was like real life porn for him to get off to. He said my mouth was his sex toy.

I’m not really into the dirty talk but something about tonight was really hot. He kept up his rhythmic fucking. Holding either side of my head and just using my mouth like a hole. He wasn’t rough – but he was making long deep strokes. When he started to pick up the pace and fuck faster I knew he was getting close. I started jerking faster too and he reached up and grabbed ahold of my nipples. He was moaning louder and I felt him tense up and the next second I felt his cum hit the back of my throat. He kept fucking in and out and the cum spilled out of my mouth and ran down the sides of my face and into my hair. He kept fucking and telling me to cum for him and suck him dry. I started sucking and beating my dick harder. I finally shot my load and he just kept slow fucking my face until I was done. His dick had started to soften and then it started getting hard again. He picked up his pace a little more and said he had one more load to drop in my mouth. My dick was getting soft and I just laid there as he worked his second load out into my mouth. When he was done he helped me get down off the bed and led me by the hand back to the den where my clothes were. He scooped them up off the floor and kept leading me down the hallway to his front door. As he opened the front door he pushed my clothes into my arms as he shuffled me out into the hallway. He said thanks and then shut the door. I was left standing there naked with cum running down my face and chest. I was a stunned. That was not at all what I thought the night was going to be. Surprisingly, as I started to get dressed I realized my dick was hard again. I wiped the cum off my face with my underwear and then shoved them in my pocket and let myself out of the building. I don’t know if I would ever do that again…but I have to say that Chicago knows how to leave an impression.