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Road Trip to Cupcake Ranch, Chapter 5: Chicago Bar Pick Up
The next day I played tourist. Sears Tower, Museum of Science and Industry, park along Lakeshore Drive, Zoo, a full day. Left my truck in the parking garage and took the public transportation. Saved Boys Town for the evening. Knew I could go to Steamworks, the gay bathhouse, if all else failed, or, maybe I would have better luck at the Y. But I wanted to roam one of the biggest gay neighborhoods in the country.
I ate supper at an obviously gay restaurant, at the counter, but did not talk to anyone, everyone appeared to be paired up, or with a group of friends. I roamed the street, went into the gay bookstores, and clothing stores, even there, nobody was looking for a guy like me. Finally went into the "Back Story Bar", it was nicely crowded, and not too noisy, and there was a seat at the bar.
There were a couple on one side of me, who clearly were into each other, and an older guy, dressed in all white, with pink sparkly glasses frames, roon the other. He looked the epitome of a faggot, and he talked like one, too.
"What have we here?" he asked as he put his hand on my leg. "New in town? I bet you have a big cock and know how to use it."
I tried to order a beer, but the bartender looked at my ID and said, "Sorry, but you can stay and have anything nonalcoholic."
"Tomato juice with lemon," I said.
"Well, yes," I said to the man in white, "I do have a big cock, but you are not my type." I had learned from the night before to look out for myself, for a change.
(Now, Mr. Editor, I know, "faggot", is like "Nigger", a word that should not be used, but, for the reader, it describes this guy, and you all know what I mean. And this is fiction.)
"I can get you some beer, or anything else your little heart desires," he continued. "Come home with me, I have some blow, and some stronger stuff if you like."
"Thanks," I said, having been raised to be polite, "but no thanks. I have other plans." Which I of course did not, at that point, only hopes.
Just then a decent looking guy came between me and the guy in white, his back to the guy in white, and got the attention of the bar tender, and ordered four Black and Tans. "This guy bothering you?" he asked me.
"Well, to be honest, he is not my idea of a good time," I replied.
"'Come over to our table," he said, "I have a guy I think you might like to meet." So, I picked up my tomato juice, with lemon, and followed him over to a table for 4 by the wall. "This is my husband, Tony," he said, introducing me to a 30 something well built guy, "and this is my cousin, Sam," he said, motioning at a 20 something guy who could have been my brother. "He is from Iowa, a farm kid, he wants to explore what Boys Town has to offer, he is not out at home, and you are the first thing that has caught his eye." This bore out my theory that gay guys are attracted to gay guys who look like themselves.
We sat, I had one of the Black and Tans, and my tomato juice, and chatted. The married couple were true to each other, and did not play with others, but Sam was available, and pretty innocent at actually doing things, although with the internet, he had seen it all. And, the farm animals had taught him about sex at a much earlier age than I found out that my cock was for more than pissing.
Sam did not say much, he was shy, but the other two guys made up for it, asked if I was local, where I was staying, how much experience I had had, was I clean, HIV neg, tested, etc. etc. All the questions Sam would ask, if he knew enough to do it.
It being established that I was staying at the YMCA, they offered to take me home, and let Sam and I occupy the spare room, and do whatever we wanted to do. "Condoms and lube in the nightstand, use towels under you, easier to wash then than the sheets, otherwise, have a good time. See you later, or in the morning. If you stay, there are spare toothbrushes in the medicine cabinet."
Sam was largely silent, until we were in the room, door shut. "Is this OK with you?" he asked. "The guys are pretty pushy and think I need to get laid or at least a blow job."
"Sure," I said, "you are a very good-looking kid, even if you do look sort of like me. Better looking than me, my nose is a little crooked."
"My dick is crooked," Sam noted.
"Well, let's see what we have," I said. And we slowly took off our clothes, Sam turned off the overhead light leaving only a dim bedside reading light. He was bulkier than me, and less defined, but had really big pecs, big nips, smooth and hairless, big shoulders and arms, and a farmer tan -- just his face, neck and biceps down were tan, the rest white as the outfit on the guy who wanted to pick me up.
And his cock, erect, pointed right and down, unlike my straight one, that was perpendicular to my pubes and pointed up at 45 degrees. We played with each other, he explored my body, like he had never been able to explore a man's body before, which, it turned out, was true. He actually asked if he could suck my cock. His first attempt was not good. "Let me teach you," I said, and I put him in 69 position and said, "Do what I do. Most important, keep teeth away from cock."
I licked his dick, base to tip, top and bottom, licked his balls, sucked on them one by one, and then, both at once, and finally took his cock head in my mouth and went down on it as far as I could, to the back of my throat, and he came! I was nowhere near that point, and so we stopped. I spit it out on his belly.
"Let's take a shower," he suggested. "Maybe I will be ready to go again, and I can take care of your boner," which was still standing firm.
We did, the shower was big enough for 2, provided they were friendly. Neither of us had ever been fucked, and neither of us was ready to try anything bigger than a finger, so we did not go there. But I played with his nips and pecs which turned me on as much as it did him.
"Did you ever kiss a guy?" he asked.
"Sure," I said, "but I have fucked more guys than I have ever kissed."
"Can we try?" he asked.
"Sure," I responded, "I only kiss guys with whom I have some chemistry, I can fuck almost anyone, but you turn me on, there is some chemistry here," I pulled him to me and kissed gently at first, "Like sucking cock, follow my lead, do what I do," I said, and taught him how to kiss, at least the way I like it. Gentle, closed lips at first, then open a little, then some tongue play back and forth, then some sucking on the lower lip, meanwhile caressing with the hands, anywhere and everywhere on the body and we were both hard, precum just dripping from our cocks which were rubbing between our bellies, more from his than mine, since I never have a lot of it.
Back to bed, he went down on me, I stayed away from his cock until I was ready to cum, then clamped down on his cock, that put me over the edge, a nice hard cock in my mouth will do it every time, and he came again as I did, both in each other's mouths, and both spit it out on the towel.
He invited me to visit him at his family farm in Wisconsin, and since I was headed that way, I agreed.
We exchanged text and email addresses, and I went back to the Y for a sound sleep, and visions of meeting him on the farm two days from then, as I continued my trip west.