Chicago Lust

By Woodrow Harrison

Published on Mar 10, 2023

Bisexual

This is a work of pure fiction. It describes homosexual and bisexual acts in detail. It is not meant to be seen by those not of legal age. If you are not of age or offended by homosexuality, please don't read further. Comments and criticism may be addressed to Woodrow_h@hotmail.com.

Perverts

The sleek long black hair covered my bared crotch and muffled the sucking sound of the full sensuous lips that were pressed around my cock in the almost empty theatre. Gloria was sucking me with great enthusiasm as I fondled the full breasts and the firm nipples of them. She suddenly rose from her knees and began to climb into my lap..... At that point I awoke, hard dick in hand and dripping with sweat. Saturday night was going to be it! I had to have her, and I was going to take her to the dumbest movie we could find. If I had to blow the whole allowance on her it would be worth it. I was going to lose my cherry no matter what. The room across the way was as dark as mine, and not knowing the hour, I figured his friend had either left or they were sleeping off a real hot session. I lay there in the dark thinking that I was going to feel the same thing he had felt come Saturday night. My hand instinctively kept fondling my dick and then began rubbing with a greater intensity until the stream of white goo spurted into the bed sheet above it. I dropped off to sleep again and was dreamless the rest of the night. In the morning, I got up early, before mom went to work. We sat at the kitchen table and drank coffee together as she outlined the days chores. She didn't lean on me very hard, though she worked a full time job and spent lots of time picking up after the average teenaged slob. She was as much a friend as a mom. When I was younger, I used to resent these guys who would come and spend the night, the grunting and moaning that came from the closed door to her room ( a door that had never been closed to me when dad was around), and the quick kisses off in the morning when they went flying out to their cars to disappear and never be seen again, but with the advent of "Uncle Dave," who came back almost every night, I had learned to accept it. No longer did I creep down to open the door a crack and see my mom covered by one of these guys, legs straight up in the air and crying like a tigress as he slapped his belly to hers. I guess I had resigned myself to her doing what she wanted to and she to accepting the cum stains on my bed sheets without comment. I think she might have drawn the line at what I'd done the past two days, but ignorance is bliss, and I'd never tell. Discretion is a necessary element of the rites of passage, and I was going to be damned discrete about this. Before she left, Mom handed me a 5 and two singles. "Get yourself a TV dinner for tonight, and here's your allowance. I'm going out after work and may not be home until quite late." I took the money and put it in the pocket of my cut-off jeans. Whenever she'd done this before, it had meant she'd be out all night, come home in the morning and go right to bed, staying there the entire day with a "headache". One of the chores she had left me to to wash all the windows in the house, inside and out. I rounded up buckets, sponges, and rags, set the ladder to the side of the house and climbed up to do my own bedroom window first. I had just finished the top pane when I heard the window across the way being opened. "Good morning." The voice behind me was deep and masculine. "Trying to improve our view I see." I chuckled, but did not turn around. "Yeah, seems I slopped something on it yesterday afternoon." "As long as you've got the ladder out, how about doing this one? I seem to have slopped something on mine as well. I'll buy you a coke." Now our refrigerator is always stocked with plenty of coke, but something made me say O.K., and finishing the bottom pane, I transferred the ladder to his wall and washed the window. Just as I was finishing up my neighbor walked into the room carrying 3 cokes. He was naked, and behind him coming from the bathroom was another man, equally naked. It hit me at once that this was my neighbor's visitor, the one I'd seen going down on him the night before! They must be gay! I had been jacking off "with" a gay man! The neighbor opened the window and invited me in. I had some misgivings about entering a house through a bedroom window when the room was occupied by two naked gay men, but the next thing I knew, I was sitting in a chair next to a full length mirror next to the window. "By the way, my name is Jim, and this is my cousin, Jack, from Milwaukee." Jim handed me the coke and sat down on the bed next to his cousin. "I'm Chip, nice to meet you." "Well," said Jim, "now that that we've all been introduced, why don't we get to know each other a little better? Come on over and join us." I hesitated and then rose. A look from Jim told me I was expected to strip, and I nervously pulled off my tee shirt and took off my shorts and jockeys, leaving them on the chair. Jim and Jack were busy pulling each other's meat as I undressed. As I sat down on the bed, Jim reached over with his free hand and began rubbing my now stiff cock. It was the first time any hand had touched me there other than my own, and it felt mighty good. Jim turned and started working in earnest on Jack, and in a few seconds, with a deep grunt, the latter spewed a wad of cum into the air. It landed on his chest. I watched fascinated as the rod in Jim's hand continued to ooze like a volcano erupting. When Jack's climax was over, he got up and walked into the bathroom. Jim turned to me and took my hand, placing it on his cock, and resumed rubbing mine with his cum soaked hand. We sat there playing with each other for a few minutes, and I knew I was about to cum from the tight feeling in the pit of my stomach. Jim's breath was coming hard as well. We lay back on the bed and rolled on our sides facing each other, neither of us missing a stroke. Jim took both our cocks in his hand and gripped them tightly moving his hips in a fucking motion. I grew faintly dizzy and began spurting my load right into his bush and balls. That set him off and I felt the warm liquid hit me as he spewed his load onto mine. Jim rubbed my cock all over with his cum and I did the same to him with mine. We let go of each other and rolled onto our backs, giggling. For the first time in my life I had jerked off another guy and had it done to me. It felt fantastic! Jack walked back into the room and regarded us solemnly: "What a mess we seem to have here," he said, "I'll have to clean you up." He went to his knees and took Jim's flaccid dick into his mouth, licking it clean of my cum, then moved to me. I felt squeamish about this, but to be honest, it felt good to have the warm mouth working on me down there. When Jack had finished I felt an almost panicky need to get out of there. I got up and mumbled something about needing to finish my windows. I threw on my underpants and pulled up my shorts. "You didn't finish your coke," said Jim, "but I'll keep it on ice for you." I climbed out the window and went down the ladder. As I was working on the front of the house, I saw Jack leave, carrying his overnight bag. He waved at me as he passed by on his way to the bus stop at the end of the street. I finished the windows and the other chores and grabbed a coke from the 'fridge. As I opened the bottle, the whole scene flashed before me again, and I found myself going up to my room to see if Jim's curtains were drawn. I was disappointed to see that they were indeed. I hadn't seen him go out, and would have, so he must still be there. I had a crazy notion to go ask for the rest of my coke, but put that down. I put a video in the VCR and was just settling down to watch when the doorbell rang. It was too early for the mailman, and I wondered who it could be. It was Jim! I stood there in the doorway speechless. He held out a Tee shirt. "You forgot this," he said. In my haste to get out of there, I had forgotten it completely, and never realized I had left it behind. "Look," he said, "I never figured things would go so far this morning. Jack and I have been..well..intimate since we were kids. It's always been just jacking each other off until now, you know, like you and I did." I blushed. As if he didn't notice, Jim continued "last night he actually asked if he could give me a blow job. At first it felt great, but I felt a little funny about it afterward, and seeing him go down on you this morning....well... anyway, he's gone back to Milwaukee. Here's your Tee shirt, and thanks for doing the window." He handed me the shirt and turned to leave. As he walked down the sidewalk he turned and winked at me. "See you later." I stood in the doorway and watched him go into his house. For a brief moment I wanted to call back to him, but he was already in the house. So it was Jack that was gay! Jim was just a regular guy who fooled around a little. Somehow I felt relief at this thought. I figured he was right about just having a little fun now and then, but letting another guy blow you was going further than I really felt "regular" guys went. After the video was over, I walked up to the store to buy my TV dinner. As I walked into the frozen food aisle, I saw Jim at one of the cases. I picked out my meal and he noticed me as I closed the door of the freezer case. "Dining alone tonight?" He pointed to the single box. "Yeah, mom's going out partying after work." "I hate eating alone, though I have to most of the time. Does she leave you alone often?" "Oh, maybe once a month or so. It's been more often lately. Maybe she figures I'm a big boy and can take care of myself." Jim shot a knowing look at my crotch. "I wouldn't argue with that idea, I've seen you take care of yourself." I grinned at the double entendre. He was good with them, and I felt myself liking the man for his sense of humor. In other circumstances we might even become friends. We paid for our purchases and walked home together. Jim told me he had just bought the house and moved here from Wisconsin to take on a new job at a nearby bottle cap manufacturing plant. They worked seven days three shifts, and his days off were Friday and Saturday. As I turned to walk up to my door, Jim said "see you later." and walked into his own house. I put the TV dinner in the freezer and popped a bag of popcorn in the microwave. While the corn was popping, I went upstairs to take a leak. When I was done, I stepped into my bedroom and peeked out the window. Sure enough, Jim's drapes were open. I glanced at my watch. 4:00 on the money. Is this going to be a daily event, like a soap opera? I stepped over to the window and looked into Jim's room. He wasn't there, but perched on the sill was a half full bottle of Coca Cola! That was no coincidence I thought. That's what he meant by "seeing me later". It was a prelude to an invitation. After a moment, Jim appeared, fully clothed. He walked up to the window and opened it, signaling me to open mine. "I was thinking", he said, "why should both of us eat by ourselves? Why don't you bring your TV dinner over and we can have supper together?" That seemed logical enough. "What time? I just made some popcorn." "Bring it over now. We can munch and watch a video before supper." "Be right there" I said. I fetched the popcorn and my dinner and walked over to Jim's house. It was pretty much the same layout as ours, but he only had one couch in the living room, opposite the largest entertainment center I had ever seen. The TV must have been a 35", and the speaker towers reached almost to the ceiling! "Wow! That's some outfit!" I gasped in envious admiration. "Living alone has its benefits too," He handed me a full coke and motioned for me to sit on the couch. His library of videos must have had at least 50 titles. He selected one and popped it into the machine. He moved over to the couch and sat down next to me. Using the remote he turned on the TV and started the VCR. My mouth dropped open as the opening scene showed two voluptuous blondes undressing each other. It was a slow sensual process, and by time they were both completely naked, I was feeling the familiar resistance at my fly. "Hot stuff eh?" Jim reached over to grab a handful of popcorn from the bag in my lap. "I'll say!" I said as the two beauties got into a 69 position and began lapping each other. The camera showed them from every possible angle. The closeups were so sharp you could have counted every hair on their pussies. I was plenty hot watching this action, and when Jim put his hand on my knee, I jumped. He drew his hand back, a surprised look on his face. I smiled at him and put his hand over my straining pecker. "Sorry man, I'm so hot I almost came in my pants." "Wouldn't want that," he replied, "why don't we get more comfortable?" With that he stood up and peeled off his shirt, then his pants, folding them neatly by the side of the couch. I could see that he was as hot as I from the right angle his cock made from his body. I stripped also and sat down next to him, my thigh resting against his. He reached over and gripped my dick. "This is more like it." he said. On the screen, two guys had entered the picture, both with huge cocks at full attention. One of the blondes was sucking while the other was getting fucked. My hand stole over and began rubbing Jim's meat. Now the scene changed and the blondes had resumed their 69 position. The guys knelt behind each of them and began fucking the girls in the ass. This was getting to be too much for me, and I knew I'd be shooting my load in a few seconds. "Oh! I'm going to come!" I rasped. Jim dropped my cock and said "try to hold it. There's plenty of time before supper." The urgency was relieved, but what I saw next on the screen almost blew my mind. Each of the girls had strapped on a two-ended dildo, the guys had gotten into a 69 position and were sucking each other off while the girls rammed the dildoes into their asses! "I don't believe this," I said. "That has to hurt like hell." "Yeah, I'll bet, but they seem to be enjoying themselves, maybe they're used to it." "Just the thought of a thermometer in my ass used to make me blanch when I was a kid, and mom always took my temperature that way." "So did mine. I hated it." Jim moved my hand from his cock."I'm getting pretty close too. Better take it easy." One of the girls had removed her dildo, and the other was screwing her while the guys continued their 69. "What do you suppose they pay these guys? I'd screw either of those blondes for free." "I'd have to get paid a lot to do what they're doing right now. I don't understand what your cousin sees in it." "Me neither," said Jim, "but then I've never tried it." The scene had changed again. One guy was cornholing his buddy while one of the blondes sucked on him and beneath her the other blonde was eating pussy. The guy being fucked and sucked looked very much like he was enjoying it. The picture showed a few more variations and then ended. No plot, just raw sex. I still had a big hard on, as did Jim, but I didn't feel on the verge of cumming any more. I reached over and gave his prick a playful grip. "Got any more?" (two could play this double speak game) "My cousin left a few for me, but I haven't had a chance to watch them yet." "Put one on," I said, "let's see how the other half lives." Jim changed the tapes and started the VCR. The scene showed a couch very much like the one we were sitting on. Two guys, one white and the other black sat side by side watching TV. The camera didn't show what they were watching, but you could guess it was pretty hot as the two got up and stripped just as Jim and I had a few minutes ago. They played with each other for a few minutes, then the black guy knelt in front of the other and went down on him. He sucked him for a few minutes then they changed places. I couldn't get over the size of the black guy's dick. It was huge, yet the white guy was taking it all the way to the hair. "That must be going halfway down his throat!" Jim was staring open mouthed at the action. "How can he do that without choking?" I looked down at my pole. Fully hard it was about eight inches long, and I couldn't close my hand all around it. There must be some trick to it I thought. Now the white guy was poking his finger into the black guy's asshole. He'd shove it slowly in and slowly pull it out. "That's not as painful looking as the other flick," said Jim, "and the guy looks like he's enjoying it." "Oh yeah? I suppose you'd like to try it?" I was joking, of course, but Jim turned and looked at me real serious. "Would you be gentle and stop if I asked you?" I thought he was joking too, but he got up and left for a moment, returning with a jar of vaseline. "You're actually serious? You want me to put my finger in your ass?" "Come on, I just want to see what it feels like." I rubbed my index finger with a generous dab of the jelly. Jim bent over the coffee table with his ass in the air. His cock dangled down in front of him. Slowly I put the tip of my finger to the tight pink hole. With my other hand I grabbed his cock from between his legs. I pushed the tip of my finger in and stopped. "OK?" I asked. "Yeah, keep going, but slowly." I inched my finger in until it touched a resistance with the whole length of it in him. I wiggled it. "Oh yes! Do that again!" His cock grew stiffer in my hand. I rubbed the resistant area slowly, and Jim began to moan with pleasure. A drop of pre-cum oozed from his cock. "Does it really feel that good?" I asked, incredulous. "It's fantastic, but take it out or I'll cum all over the table." I pulled my finger out and looked at it, expecting it to be covered with shit or even blood. It wasn't, but it did have a slight odor. "You really liked it?" I looked at him searchingly. "Yes I did. I was afraid it would hurt, but when you got all the way in there and started massaging, it was the greatest feeling I ever had." I was curious but skeptical. "You're not kidding?" Now it had never crossed my mind until Tuesday that I would enjoy watching another guy jack off, let him see me doing the same, jack another guy off and having him do me and finally having his cousin lick off the mess, but so far except for the last I had enjoyed it, so I figured what the heck. I crouched over the coffee table while Jim oiled up his finger. His hand closed over my cock and that felt good, but I jumped a little as the fingertip touched my anus. It was tight, but felt surprisingly pleasant as the insistent finger probed deeper into me. Finally he touched something inside there, and I felt my cock swell in his hand. Oh! Did that cause a sensational feeling! He rubbed me inside there and I moaned aloud with the pleasure of it. "Oh! I'm right on the verge!" Jim slowly withdrew his finger, and somehow I held back the flow. He dropped my cock and we resumed watching the video. The Black guy was now on his hands and knees and I gasped as the white guy began to lick at the puckered anus! When he had his man dripping with saliva, he brandished his massive pecker and aimed it at the black guy's ass! "He's going to fuck him!" Jim was breathless. The long white snake paused as the head approached its target, then slowly disappeared into the hole, till it was buried to the balls. Now he pulled it back, almost all the way out. They developed a cadence and we watched fascinated as the two men struggled. Suddenly, the white guy pulled his cock out and began to spurt huge wads of cum onto the black man's back. Almost instantly, he knelt down and the black guy started fucking him. I couldn't believe the he could take that massive tool so easily, remembering the tightness I had felt when Jim had his finger in me. I also remembered how good that finger had felt, and found myself wondering what it must feel like to have a dick inside there doing the rubbing. The video ended with the black guy shooting his load all over the white guy's back. Jim reached over and began pulling my pecker and I returned the favor. We were both brick hard, and soon I felt like I was going to cum. My breath came hard and Jim let go of my dick. Again I was able to hold back. He got up and suggested we have our dinner. It felt funny, sitting there stark naked eating dinner, but it had been a day of many weird feelings and I hoped it wouldn't end with the meal. Jim and I were exploring new concepts of our sexuality, and although I did not consider myself homosexual, I was certainly interested in learning the pleasures that men could enjoy together. The disgust I had felt that morning when Jack had gone down on each of us was dispelled, and if Jim suggested it, I might be willing to try a 69. Dinner over, we washed and dried the dishes. "Want to watch some more videos or TV?" The question made it clear that Jim expected me to stay. "Sure, got any more hot one's?" "I think we can find something interesting." He popped a cassette into the machine and sat next to me on the couch, close enough to be touching me. I was feeling more comfortable with this all the time, and as far as I was concerned, he had carte blanche with my cock. The film featured a black haired girl with enormous tits going down on a black deliveryman. To my surprise, it looked as though he was the same actor as we had seen in the gay video before dinner! The girl was taking the whole of that monstrous cock, and again I wondered how that was possible. The thing must have been almost a foot long. "How can she do that without choking?" "I don't know, but she's doing all right. If it was too much for her I'd be happy take his place though." "You could take sloppy seconds behind me," I replied. "Well, that guy is getting the head and we're getting the tail." There was another double entendre which was not lost on me as Jim put his hand on my half hard cock. "Of course....." Jim's voice tailed off. "Of course what?" I asked guessing what was in his mind. "Well, you know....neither of us have ever tried it, but...." "You mean go down on each other?" I pressed the point. "Well, I guess....do you want to try it?" I was shocked at my own boldness as much as my willingness. "Might as well, why should he have all the fun?" Awkwardly, we lay down on the floor heads to each other's crotch. Looking at it up close, Jim's cock seemed much larger than it did in my hand, and I wondered if my mouth was big enough to get it in there at all. I put my fingers around the base of it and lifted it to see the underside. Blue veins bulged like ropes along the length of it, and the head formed a vee shape that looked like a pair of eagle's wings. The hole in the end of it was squeezed shut like a sleeping eye. I licked my lips and placed the head between them. It was very warm and surprisingly smooth. I let a bit more in and instinctively began to lick around the rim of the circumcised head. At this point I felt my own cock entering Jim's mouth, and the warm wetness of it was fantastic. I let more of Jim's cock into my mouth until it touched the back of my throat. I gagged slightly and Jim moved as if to pull it out. I grabbed his asscheeks and pulled his body to me. If I was going to do this I was going to learn to do it right, and I didn't want him to quit sucking me. He was slurping merrily on the end of my cock, and I was thoroughly enjoying it. After a few minutes of this, I discovered that, by breathing through my nose I could take the end of it into my throat, and finally got it all the way into me, my nose pressed into his bush of hair. Jim, for his part, caught on and I felt the entire length of me inside his mouth and throat. Despite the fact that I had been turned off at this this morning, I was in ecstacy now, and hoped that we could go on with this for hours. I knew that this intense activity was going to culminate in a few moments, and I wondered if either of us was going to swallow the semen. I felt Jim's body stiffen. He stopped sucking me but held my dick tightly between his lips. I knew he was trying to hold back, and on a crazy whim, I reached my hand around his backside and rammed my middle finger up his rectum. The result was a bucking motion and a stream of chalky tasting fluid that filled my mouth, flooded it, running out my nose and the sides of my mouth. Now I really gagged! I took a deep breath and put it back in me as I felt a rush to my head and an intense tightening in my stomach. I was going to run my load! "Put your finger in there," I gasped. Jim did as I asked and I spurted a mighty load into his mouth. He followed the first jet, and let go of my cock. The second spurt caught him on the cheek, and the third dripped onto his chin. The euphoria we were feeling was indescribable. It was his second ever blow job received and the first given, the first time for me for both. We just lay there savoring the experience, tasting the strangeness of each other's cum in our mouths. "Where's Jack when you really need him?" Jim broke the silence with an attempt at humor." "Who needs Jack?" I growled, moving up to face Jim. Surprising myself, I began to lick my own cum from his face and he did the same to me. He looked into my eyes, our lips parted at the same moment and pushed together. We held each other tightly as our jousting tongues prolonged the ecstacy of our first union.

Next: Chapter 3: Discovery


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