On Monday morning, I woke exhausted and sore. Sore, obviously, because of the big cock that had used my hole and exhausted, well, really for the same reason. I needed more sleep for my body to recover, but I couldn't lay around all day, the bank had sent me to this conference so I felt obligated to go to each session. I hadn't requested a wake-up call and the alarm on my phone hadn't gone off, it was the sun rising over Lake Michigan that had woken me since I hadn't closed the curtains before I'd fallen asleep. Since it was early and I had a couple of hours before the first session at 8 am, I decided to go for a run along the lake. I put on my running shorts, a t-shirt and my running shoes and went down to the lobby. When I stepped outside, I was hit with, what felt like, a wall of water. I knew Chicago got humid but it hadn't been as humid the day before. After just a short distance, I was sweating, so I took off my t-shirt and stuck it in the back of my running shorts.
The path along the lake was full of other runners and people on bicycles and skates. At this hour it was almost completely people who ran, biked or skated as part of their regular routine. There were men and women who were lean from long distance running all the way to muscle heads who used the path for their cardio. The sights were worth the early morning run. As men came toward me, I would be checking out was swinging in the front of their shorts. Almost every man was shirtless and the women were in sports bras. Hard, defined pecs weren't escaping my eyes either. I'm glad the shorts I had chosen had good support or my cock would be sticking out.
Just as I was checking out the guys who were running toward me, some of them were obviously checking me out as well. Some of the guys that were passing me would glance back over their shoulders. I was enjoying the attention as well as enjoying what I was seeing.
After 20 minutes, I turned to return to the hotel. I usually run for at least an hour but I needed to get ready and get something to eat before going to my first session. I started to notice runners going into, or coming out, of bushes that were occasionally along the path. One runner who passed me, looked back at me several times before stopping a ways ahead of me. He kept his eyes on me as I got closer while he stretched. Just as I was getting close, he grabbed the bulge in his shorts and started to walk into the overgrowth. When I passed and looked back, he was still watching me with a look of disappointment on his face. As much as I wanted to stop and play, the combination of my sense of obligation to make the first session, plus my sore ass, held me back even though I did take it as a compliment.
I was covered in sweat when I entered the lobby which caused me to shivere from the air conditioning. Several hot men were in the lobby. Some were in business attire while others looked like they were getting ready to go sightseeing.
As I got on the elevator, another man got in. He looked to be about my age. He had wavy black hair that he had sculpted to have just a little upward point at the front while the rest had the same kind of messy look that I like to do. He was maybe 3 inches taller than my 5'10" and I guessed about 190 pounds. He was wearing a blue suit but had the jacket over his arm. His dress shirt was bright white. Since I had gotten on first I was more toward the back so I could tell that the shirt had been taken in so that it fit his broad shoulders and narrow waist. It was one of those suits that were becoming fashionable, very slim, tight fitting pants that ended just above, what looked like, a very expensive pair of shoes that matched his belt. I could see in the reflection from the mirrored doors that he was wearing a skinny tie that just accentuated the size of his pecs.
I don't know if he caught me checking him out in the mirror but he said, still facing the mirror, "Did you have a good run?" His voice was deep.
"It's really muggy but the scenery along the lake was great."
"I bet, I would have liked to get in a run but I told a client I'd meet him for breakfast. Maybe I'll get one in tonight or tomorrow after my conference is over." The door to the elevator opened and he got off turning toward me, "Have a good one."
The way the suit pants fit him both front and back, how his torso narrowed, his voice and the cologne he had been wearing got me even hornier than the run had made me. When I got back to my room, I showered, shaved, fixed my hair and got dressed in the black suit I had brought. I paired it with a royal blue shirt with French cuffs and a tie that was the same shade of blue with black and some thin lines of pink. It was my first expensive suit and I liked the way I looked and felt when I wore it. I grabbed my stuff, put the lanyard with my name tag around my neck, and headed back to the lobby where I grabbed some juice and a bagel. While walking through the many hallways to get to the part of the convention center where the programs were, I finished eating and drinking. Luckily when I got to the right section of the convention center, the organizers had coffee set out, which I needed badly.
The first two sessions I went to were really good. I stayed focused on the topic and not on some of the men that were around me. After the sessions, there was a break in the exhibition area where, luckily, there was more coffee. I walked around checking out what the vendors had to offer. I wasn't really in a position to make a decision about any of the stuff, but I thought it would be good to learn what was out on the market. I was so engrossed in seeing as much as I could that I ran into what felt like a brick wall. I stepped back, realizing I had bumped in to someone, someone hard. "I'm so sorry."
"No harm, no foul. You clean up pretty well." I looked up to the man's face and realized it was the guy from the elevator but he had his suit jacket on now. "So, we must be attending the same conference." He looked at my name tag, "Chad."
The smell of the man's cologne got me hard again, I should have beat off in the shower. "Yeah, I guess." I looked at his name tag, "Matt."
Matt took my name tag into his hand, "I've never done business with your bank, but now that I've seen you it might be worth a visit." Was the man flirting with me?
"I'm just one of the worker bees. I don't make decisions about.....what is it you sell?" The name of the company on his nametag didn't ring a bell.
"A software platform for all things HR, from worker bees to CEOs. Everything is stored in a secure cloud, so there is no reason for a server farm." I sort of understood what he was talking about, the fact that he was so close didn't help matters. "Stop by my booth and I'll tell you more about it. You may not be making the decision now but you could be in a few years. Might as well start building the relationship now. Who knows, you might actually find something else you might like, Chad." Then he was gone, lost in the crowd of people moving by the booths.
The next session I went to was good and was followed by a light lunch in the exhibit hall. As I walked the aisles of vendors I looked for the one that Matt would be working. Just as lunch was ending and it was almost time for the next session, I found the booth. Matt was talking to a woman that seemed more interested in him than in the software. Matt held up a finger, the universal sign of 'give me a minute'. After a moment, Matt told the woman that he needed to speak with me, that I'd been waiting, and how he hoped to hear from her about a demonstration, and with much emphasis, 'of the software'. The woman seemed a little put off but she finally left, telling Matt she would email him soon.
"Thank God you showed up, she was making me crazy. She wasn't interested in the software, she was interested in my hardware. It's a hazard of this business, I have to make nice if I want to make a sale. Now you, on the other hand, I would love to have take a look at my hardware." He pulled the side of his suit jacket to the side so that I could see that his hardware, did in fact, need some attention.
Looking at my watch, "Uhhhh, I have to get to a session."
"You sure? I thought for sure that the way you were checking me out in the elevator that you were ready to get on your knees right there. If I didn't have to be at the booth when the conference started this morning, I would have dragged you to my room and don't tell me you wouldn't have come." The aisles were emptying out as the other attendees left for sessions. "It's pretty boring here when the sessions are going on, I could use the diversion." A small, very small, part of me couldn't believe that this conversation was taking place at a business conference. "You know that you want to find out what I have under these suit pants and I'm positive you are going to like it." I did find his confidence appealing. He went behind the table that was part of his booth and sat down. He slapped his hand on the second chair, "Come on and join me for a little while."
The wheels in my head were going round and round: he's hot; the bank is paying for me to go to sessions; he's really hot; could there be a conflict of interest; no, my bank doesn't do business with his company; what if the bank finds out I skipped a session; what does his cock look like; I really should leave. Cock won.
I went behind the table, which was covered with a table cloth that went to the floor that had Matt's company's logo, and sat down. He must have been busy while I was debating with myself, because as soon as I sat down, he grabbed my hand and brought it to his cock, which was sticking out of his suit pants. He held his hand over mine and started making small stroking movements on his cock. Matt's dick was thick and had a lot of veins with a large one running along the underside. As soon as he thought my rhythm was good enough, he pulled his hand away. The more I moved my hand the farther apart the tips of my fingers got. The crown of his head felt huge as well, I didn't even try to move my fingers higher.
Occasionally someone would stop at the table, someone else who was also ditching a session. Matt would raise his ass from his chair, but not fully stand so his waist was below the top of the table. He'd shake their hand and make small talk while I continued to stroke his cock. Sometimes the person would stick out their hand to introduce themselves to me, and since I was to the left of Matt, I would have to let go of his cock, stand and shake the person's hand with the one that had just been caressing Matt's dick. I would sort of bend a little at the waist so that the person couldn't see the bulge in my suit trousers. If the person wanted to know more about the software, Matt would suggest they come back at a certain time so that they could have a longer conversation. While most seemed fine with the idea, I got that sense that some thought he was blowing them off, which he was.
Matt was a slow grower but it wasn't too long before the head of his dick was brushing against the underside of the table. I got the sense that he enjoyed the texture against the tip of his cock. I turned my head to Matt and asked, "Are we really doing this?"
"Oh yeah, and you'll be doing more in a few minutes." I think the guy at the booth next to Matt's had an idea what was going on. He kept looking over and I had the sense that he was rubbing what was growing in his pants. When the traffic had completely come to a halt, Matt moved my hand away from his cock and struggled to get it back in his pants. I was sure that the man in the next booth was watching because he kept looking at us. Finally, Matt gave up because he just couldn't get it back in his pants. He took off his suit jacket and put it over his arm, covering his crotch as he stood up. "Follow me."
Behind all of the booths were black curtains. Matt pushed the curtain aside and we were in a space with curtains on either side. The aisles were set up in such a way that booths backed up to other booths but were separated not only by the curtain but by a narrow space between the curtains. It looked like the vendors kept their extra boxes of marketing materials back there, keeping them out of sight. Matt threw his suit jacket on a box of marketing materials and I finally got a look at his dick. It was still sticking out of his slacks at an upward angle. "It's all yours."
I took off my suit jacket as well, looked around, and then lowered myself to my knees. I looked up into Matt's face, "What if someone sees us?"
"My guess is that they are either going to be jealous of me or jealous of you. If they're not and they call my company, fuck 'em, I won't get in any trouble. All I have to say is 'anything to land a client' and I will probably get a pat on the back." With my fingers now once again wrapped around the shaft of Matt's dick, I leaned in. His cock smelled of the cologne he was wearing. I guess he proved the theory that dabbing some cologne by a major pulse point works.
While Matt's dick wasn't anywhere near as large as the man from last night, it was well above average lengthwise and was exceptionally thick. Even though my jaws still hurt, I opened my mouth and but my lips around the head of Matt's cock. While his shaft was steel hard, his head was sort of spongy and I had fun exploring it with my tongue. Unlike other men who wanted to blow their nut quickly when being semi-public, Matt didn't seem to mind. He seemed to enjoy watching me work. After thoroughly exploring the head, I began to take more and more of Matt into my mouth causing him to purr.
Unlike other men, Matt didn't thrust his hips or pull my head, he just let me do my thing. I think he was so confident, he expected me to do all the work, which at the moment was fine with me. When I was moving my lips completely down his shaft and back up, Matt said, "Wish it was you, don't you?" I tried pulling off of Matt's cock, but he put his hand on the back of my head, "Don't stop." I craned my neck to the side and saw that the man at the next booth was standing behind me, with his cock out and stroking it. "Sorry man, he's all mine, unless you want to work on me." The man must have communicated something without saying a word because Matt said, "Cool man, after the booths shut down today, I'll be glad to let you have a taste."
The sessions must have just finished because I could hear more talking from the other side of the curtains. I picked up the pace. Matt murmured, "Yeah, bring it home." I felt Matt start to rock his hips so I knew not only was time up but he that was ready. I clamped my lips and pulled back so only his head was in my mouth and he let loose. As quietly as possible, Matt said, "Fuck!" After feeding me a good sized load, Matt pulled out of my mouth and took a handkerchief from his back pocket and wiped off his cock. He was still somewhat hard so he struggled to get his meat back into his slacks but this time he was successful. He put his suit jacket back on and put his hand on my cheek, "Thanks man, how about I join you tomorrow morning for a run and have some more fun?" Still on my knees I nodded, "Cool, meet you in the lobby at 6:30." He went back out to his booth.
I stood up, rubbed off the knees of my slacks and put my jacket back on. The guy from the other booth was still there, "You lucky son of a bitch, I've been trying to get his attention since yesterday." He then went back out to his booth.
After I composed myself, I went through the curtains and was standing behind Matt. He was talking to one of the conference attendees. As I passed by him to get out to the aisle, he looked at me and made a swiping motion with his index finger on the corner of his mouth. I did the same and found a glob of his sperm, I wiped it onto my finger and sucked it off. Matt gave me a smile as I walked away.
For the next couple of sessions, I tried to stay focused but it was hard, I could still taste Matt on my tongue. There was another cocktail reception in the exhibit hall at the end of the day. While drinking some generic white wine again, I walked by Matt's booth hoping he might want to grab some dinner and have some more fun, but he was surrounded by a group of both men and women who I was sure had the same idea I did.
After another glass of wine, I went back to my room and decided to order room service. While I was waiting, I got out of my suit and took a nice, hot shower. A fantasy was running through my head that the room service attendant would be some hot guy who would throw me down on the bed and have his way with me. In anticipation, I wrapped my waist with a towel when there was a knock on the door and opened it. The fantasy flew from my brain, the room service attendant was a middle aged man who could not have been any more of a queen if he tried, now don't get me wrong, I don't have any problem with that, but he was not going to meet my need for more cock. From the way he was acting, I could tell that he was disappointed that I wasn't the kind of guest that wanted some additional service from him. I did, however, take advantage of the situation. After he had laid out the food on the small table in my room, I asked him if he had any suggestions on where I might go that evening. I told him I was from out of town and didn't know Chicago that well.
"Well, there's always Boystown, there are a lot of bars there. It's on Halsted Street a couple miles North of here."
I had heard about Boystown, I actually had done some research when I knew I was coming to Chicago, but the impression I got was that it was pretty much a bunch of bars that while nice; with lots of music, videos, drag shows and expensive drinks; and would be fun to go to with a group of friends, wasn't quite what I was looking for and I told him that.
"Well, there is a place called 'Big Jim's', it's sort of cruisy but an older crowd."
"Any other suggestions?"
Throwing a bit of shade, "Honey, if you're looking to get laid for sure, I have two options. If you want to have a cocktail and then get laid, try Manhandlers, it's on Halsted but not as far North as Boystown. If you're just looking to have some cock up your ass, and you don't want a cocktail, go to the Bijou on Wells, with your face and body, you'll be the belle of the ball."
I gave the man a good tip and thanked him for the information. Both options sounded interesting and since I had two nights left before I flew back to Phoenix, I decided to try both. A place called Manhandlers sounded fun, so I decided to go there first. Since it was still early, I ate the dinner I ordered, set the alarm on my phone and took a 2 hour nap. When I woke up a 9 PM, I felt a lot more refreshed. I did some primping and personal hygiene before putting on the sluttier pair of jeans I had brought with me. They were actually my favorite pair, I had gotten them while I was in high school and they were well worn. They were frayed and had been worn out, not only on the knees, but on my thighs as well. The area over where my cock laid was worn down to just threads. Just under the back pocket, on the right, was a rip that was big enough to show the curve of my ass.
Along with my jeans, I had brought several tank tops, one can never be too prepared. Unlike the one I had worn when I did my run in the morning, the one I chose was cropped a couple inches above my waist and the fabric below the arm holes was ripped almost to the bottom. I wasn't sure what Chicago was like, but I hoped it wasn't too early to be going out.
I grabbed my room key card, my driver's license and a couple of the $100 bills that the man from last night had left me. I got a lot of stares as I walked through the lobby and while I was waiting in the cab line, but I didn't care. While I didn't know where Manhandlers was, except that it was on Halsted Street, the cabby knew exactly where it was. Traffic wasn't bad, so we got there relatively quickly. When I handed the cabby a $100 bill for the fare, he said he didn't have change for anything larger than a $20. While I was deciding if I was going to let him keep the $100, he offered another option, he told me if I gave him a blow job we'd be good. Well, the man was definitely not my type, on many levels, but the only other option was to take me back to the hotel and not lose as much money, so blow job it was. He pushed the shit he had on the passenger seat onto the car floor, I moved up front and....you can take it from there. Definitely not satisfying on my part but he seemed happy.
Once I had 'paid' for the ride, I went into Manhandlers. Since it was a Monday night, I assumed that it wasn't as crowded as it would be on the weekend, but there were still a lot of men. Not only a lot of men, but a lot of the kind of men I like. While the age range was wide, there were hot men of all those ages. My eyes kept wandering around the bar, landing again and again on men whose cocks I'd like to get to know. I wormed my way up to the bar and ordered a Skinny Bitch instead of a Cosmo. I thought that vodka and Diet Coke was the better choice under the circumstances. I felt a few hands graze my ass as I waited for my drink. Luckily, the bartender, who was cute by the way, was able to break a $100. I was amazed at how inexpensive the drink was.
Once I had my drink, I started to wander the bar. When I saw a man that attracted me, I made sure he noticed me. The place was really a dive, it sort of had the vibe of Cheers but with a raunchy factor. There was an area behind the bar that was an outdoor patio that was full of smokers. I kept wandering, and since I was horny as hell, was brazen enough to feel men's chests and bulges as I walked by with a smile.
After getting a second drink, I went back outside and went toward the back of the patio. There was another area that was covered but still open air. I continued showing my interest in some of the men by touching them as I passed by but now I felt hands touching me. As my eyes adjusted to the low level of light, I saw that more was going on than I had originally thought. While there were a lot of shirtless men, there were also men that were wearing nothing. This was much different than any of the bars in Phoenix. I walked by men on their knees feeding off of a cock, sometimes more than one, while other men watched.
Off to the side I saw a man that was standing alone. He was tall, maybe 6'4" or 6'5", with a body that was chiseled by hard work, not some machines or free weights at the gym. He was shirtless with a pair of jeans that looked like they would slide off his body, they were so low. He had a pair of chunky boots on his feet. While I couldn't be sure, his skin made me think he was Latino, Mediterranean or multiracial. While he was smooth, his face had a day or two of growth. His hair was short, not a crew cut, but something close. Men would stop as they passed him but he acted as if they weren't there. I stood off to the side just watching him. Every once in a while he would bring a bottle of beer to his lips and take a swig. As I watched, one guy stopped in front of him and obviously was ready to do anything. The tall man handed him the bottle of beer he had been drinking and the other man scurried away. While a couple of men stopped and tried to start a conversation with me, I couldn't stop watching the tall man. The man who had taken the empty beer bottle from the tall man returned with another bottle. The tall man took it, took a swig, and acted like the other man wasn't even there. Finally the man who had brought the beer left. It was at that point that the tall man looked directly at me. His eyes locked with mine. He didn't do anything to indicate that he wanted me to come over but I was drawn to him.
I don't know why, but as I moved toward the tall man, I pulled the front of my shirt up and behind my head. As I got closer, another man stepped up to him, the tall man never took his eyes off of me. When the other man got to close, the tall man put a hand on his shoulder and pushed him to the side. It was like the tall man was a magnet and was drawing me to him. When I was just a few feet from the tall man, his eyes finally left mine and looked me up and down. As I stepped even closer, he reached out and pinched one of my nipples. I stepped back and he grabbed me with his long arms and pulled me close, close enough that I could smell him. He put a hand behind my head, pulled me closer, lowered his head and put his lips against mine. His tongue forced its way between my lips. I'm not a kisser, so I tried to pull away but he wouldn't let me. I felt his tongue spar with mine while one of his hands went down the back of my jeans, squeezing my ass.
I felt like I had no control. One of my hands went to his pecs while my other hand caressed one of his biceps. The hand that was down my jeans pulled me forward so that I could feel the bulge in his jeans against my abs. He held me so tight I couldn't move. He finally broke the kiss and moved my head so that my mouth was at his pecs. I had no choice, I started to lick, tasting the salt from his sweat on this humid night. When my tongue ran over his nipples he held my head even tighter, I sucked each of them.
The tall man took one of my hands and forced it down the front of his jeans until my fingers were against his cock. At the same time his fingers had found my asshole and one of them was pushing in. He pulled my head from his pecs and brought it to the bicep of his right arm. I licked it, I nibbled it, and I rubbed my cheek against it.
With my free hand, I opened the top of his low-rising jeans and pushed them down. I didn't care who was watching, I needed to free his cock. When I had, he brought my lips back to his, as I did he pushed my jeans down so that my ass was exposed which was fine with me.
I tried to lower myself to that I could taste his cock but that wasn't his plan. He spun me around and rubbed his cock against my ass. He pushed on my back until I was bent forward. He used one of his hands to rub the head of his cock along my ass crack until I felt his head against my head. I couldn't think of anything other than feeling his cock in me.
Several men who were watching what was happening stepped toward me and took their cocks out. The tall man pushed them away. He didn't want another cock in my mouth. With one hard push his cock entered me. He didn't care how it felt, he was going to drive his cock in as far as he could. Even though I groaned, it didn't make a difference, my ass was his. Since it was his, he used it. His thrusts were hard. If it was causing me pain, he didn't care, he had one goal and one goal only. I think he fucked me for almost 30 minutes while we were watched by a bunch of men who were either beating their cocks or had them down the throats of other men. All I could smell was sex.
When the tall man came, I think it went farther than any man who had filled my ass before and I ended up shooting my own load on the floor. His still hard cock stayed in my ass and he continued to fuck me. He kept it up until he came a second time and I did as well.
After the tall man came the second time, he pulled his dick from his ass and spun me around. His cum slick cock rubbed against my abs as he pulled my lips to his again. His tongue was as aggressive as it was before. If his tongue could have cum, I think my throat would have also gotten a load.
When his tongue retracted from my mouth, I stepped back. He pulled up his jeans and stuffed his dripping cock back into the denim. He acted like I wasn't there. His eyes were above my head scanning the crowd of men. I pulled up my jeans and pulled the front of my tank top from behind my head. I walked away from the tall man, noticing the glances of the men I passed, and walked out of the bar and luckily found a cab right away.
With cum seeping out of my ass, I walked into the Hyatt, my only thought being was that I loved Chicago.
TO BE CONTINUED......