Shyoldguy Generations 
 
 
   
 
This is a work of fiction containing gay consensual sex between adults over 
the age of 18 years old.  If it is illegal to view this material, offended 
by the content or underage, please leave this site immediately. This work 
of fiction/fantasy is the product of the author and maybe not be copied 
and/or published in any way without the express consent of this author.  No 
one in this story is real, living or dead.  Any resemblance to a living or 
dead person is purely an accident. 
GENERATIONS 
I had taken a personal day from work to run some errands and had just left the electric company where I had been trying to get my bill straightened out. I had just left their offices, and was crossing the street heading for my car, when a young man approached me. He looked to be in his early 20s, with short dark hair. He was wearing a plaid shirt unbuttoned and showing off his smooth chest, he must have kept it shaved because with his dark complexion and dark hair he should have had chest hair. His tight jeans showed off his nice round butt, and his package. There was a large hole in the left thigh where his blue boxers were exposed as well as some creamy skin. He had on ratty sandals, and his feet had a light coating of dust. “Want a blow job mister?” he asked. I was shocked, no one had ever been that bold with me, usually if I wanted something like that, I would have to go looking for it, and no one that looked like him wanted to blow an old guy like me. “I’m sorry?” I responded, “Do you want me to blow you, twenty bucks.” He said again. Without thinking I said, “No, no thank you.” With a disappointed look on his face, he turned and walked away. I stopped and thought about it for just a split second, and said, “Ok, Where?” He turned back to me and smiled. He had such a winning smile, beautiful full red lips, and showed off just enough of his white straight teeth. “Your car would be ok with me.” He said. I thought about that for a second, and said, “Ok, over here.” And we both headed to the parking lot.  
I had parked my SUV toward the back of the lot all by itself so no one would hit it with their door and leave a mark. I popped the locks, and I got in on the driver side, he in the passenger side. “Do you want to pull it out or do you want me to go after it?” he asked “I’ll do it.” I said as I unfastened my belt and undid my pants and zipper. I lifted my butt and pulled them down past my knees so he would have plenty of room to get at me, and I could also spread my legs. It gave me a rush knowing that someone might come by and see. “Your cock looks great, but let me see the twenty.” He said, flashing his gorgeous smile. I fished my wallet out of my pants, and passed him the bill. He tucked it in his pocked, and then leaned over and shoved his face in my lap. In one swallow, he took my whole six and a half incher in his hot young mouth, and took it down his throat. This kid was good, and he had done this before. He worked those throat muscles and his tongue until I was so ready. I was humping my hips, and holding his head with my hands, and let loose with a huge long orgasm. My cum shot down his throat. I had stopped breathing, and my heart was racing, and my legs shot straight out, pressing down on the break peddle. When I turned loose of his hair, he sat back up, opened the door, and spit my cum out onto the parking lot. He then worked a travel size bottle of Scope mouth wash out of the pocked of his tight jeans, rinsed and spit again. I was working at pulling my pants back up, and asked him why he was sucking guys for money. “I need the money.” He said in a tone of voice that indicated that he thought that was a stupid question. “What for?” I asked. He paused for a minute, and looked me in the eye. “Because I lost my job, and even with my scholarship, I need money to pay my rent and buy food. I can make about $100.00 a day doing this and it fits my class schedule.” 
“Don’t you have someone that can help you?” 
“No, I was in foster care since I was 8 years old. I had to suck off some of the older boys just to stop them from stomping me. Even some of the foster fathers made me do them, and even one of the mothers. Sucking is not the only thing I had to do either. I have had to use my body to survive then, and I need to use it now. What’s the big deal?” As he said this a tear started running down his cheek, and he started to get out of the car. “Get back in,” I said, “I’ll drive you home.” 
“It’s too early; I still need to suck two more guys before I can go home.” 
“I’ll give you the forty bucks, just get in and let me take you home.” 
“And, what do you want for your money big boy?” 
“Nothing just get in.” and he did. I really did plan on just driving him home, giving him a fifty and leaving. He cried on the way to his apartment, and kept apologizing to me for doing it. He said that he was so tired of working so hard, and just not getting anyplace. I found out he was 23, (I was 53) and just a junior in college, it was hard to study, and work, and keep his grades up to keep his scholarship. He was so beat down. I tried to be encouraging, and tell him I knew how hard it was, but it would be worth it in the end. He just laughed. He needed someone to tell him they were proud of him. He may have been 23, but he was still a little boy. When we got to his place, I pulled up front, and put the car in park. He leaned over and kissed me. I was so shocked, but aroused by his lips, that I kissed him back. 
“Are you sure you won’t come up.” 
“No, I can’t, I told you I wouldn’t do that to you.” 
“But, I’m asking you, please, I really want you to.” I was so tempted, he was so cute, and I found his vulnerability intoxicating. I tried to stay strong, but he kissed me again, and put his hand on my cock, and it was all over. We went in the building. It was old, and hot in the hallway, we went up a flight of squeaky stairs that were covered in dirty green carpet. The place smelled of rot, urine, and cooked cabbage. When we reached the second floor we ascended yet another set of wobbly stairs, only these did not have any carpet, and the treads were worn from years of use and little repair. There were two apartments on the third floor, and he opened the one on the right. The apartment was one room and hot, there was a mattress on the floor covered with a ragged sheets, a stand up shower was in the corner next to the kitchen sink beside a table with a small microwave and a two burner hot plate. The toilet was in the closet, and his clothes were scattered around the room. There was a plastic lawn chair at a tv tray in front of a box with a small television on top, there was a coat hanger sticking out of the top of it.  
The ceiling dropped at a fierce angle, and the room’s only window was almost at floor level. “Home crap home.” He said. He turned and took off his shirt, throwing it on the plastic chair; he turned on the window air-conditioner. He saw the look in my eyes as I saw the conditions he lived in, and the tears started again. I took him in my arms, and held him as he cried. “I have tried so hard.” He said between sobs. I started rubbing is back as his salty tears soaked my shirt. He pulled back from me, and took me by my hands and led me to the mattress. We lay down together, the sheets smelled musky, and I held him in my arms. I was so aroused just laying fully dressed next to him, I still had my shoes on. “I like lying here with you like this.” He said as he put his mouth on mine. I could taste the mouthwash he had used in my car. I slowly sucked his tongue into my mouth, and gently played with it. I then used my lips and kissed the tears off his cheeks. He started to unbutton my shirt and exposed my hairy chest and hard nipples. He took my nip in his mouth and played with it with his tongue. He made whimpering sounds as he moved from one to the other. My hands played over the skin on his back, he had fine soft hair there. He moved my shirt off my shoulders, and kissed them too. I lifted my arms so that he could take my shirt off, when it was laying on the floor next to us; he buried his face in my armpit and licked it. I have had sex with men several times, and no one had ever done that. Who knew that it could be that arousing?  
He rolled onto his bask, and I climbed on top of him straddling his chest. His arms were outstretched, and I placed my hands on his shoulders, and slowly slid them down to his wrists, when my face was next to his I kissed him deep, and he took my tongue into his throat. I laid down on top of him my pouch rubbing on his through our pants. I kissed my way down his neck, feeling his heart beat on my tongue. Down his chest, pausing at his nipples my mouth slowly traveled lower. When I reached his belt, I stopped. He started to unfasten his belt, and undo his pants to give me access. I pulled his jeans down his legs. Because they were so tight his boxers slid down with them. I removed his sandals, and pulled his pants off, dropping them on the floor. I was surprised how small his wiener was; fully erect it was only about four inches and only a little bigger around than my thumb. He must have taken a lot of teasing in the locker room. I bet when it was soft you could hardly see it. I climbed back on top of him and started kissing his naked body. I could smell his sweat on his skin. It was not a bad smell, but one that turned me on. His skin felt soft on my tongue, and tasted salty. “Do you have any condoms?” I asked, knowing this ass had been well used. He reached under the edge of the mattress and pulled out a strip of them. I knelt between his legs, and used my teeth to pull open the foil.  
I took out the little rubber disk unzipped my pants letting my swollen cock pop out, and rolled it on,  burping the air out of it for a tight fit.  I then lifted his legs onto my shoulders, feeling the hair tickle my neck. I slowly pressed my rock hard, rubber coated cock in his well used hole. He was open for me, but still tight enough to give me pleasure. I started out slow, and then moved to a faster rhythm. His warm body surrounded my shaft, and he moved his cunt muscles in time to my thrusts. We looked in each others eyes, and he smiled, and I came. I continued to thrust my spent and semi hard cock in his ass, while I opened another condom and rolled it down his diminutive shaft.  I didn’t have to unroll it all the way, and wasn’t sure it would stay on, it wasn’t very tight. I then let my dick slide out of his hole, lowered his legs, took off may pants and positioned my self over his cocklet. It may have been tiny, but it was super hard, and slid easily even in my tight man pussy. “You don’t need to do this.” He whispered in a soft feminine voice. “I know it’s small, and it won’t be good for you.” “It feels just fine.” I said, panting as I bobbed up and down on his little thingy, and my voice coming in short gasps. I felt him tighten, and thrust upwards to meet me, he let out a moan, that was almost in auditable, as he filled the condom with his seed. I proved him wrong, his little boy thing set me off, and I let loose with another load on his face and chest. He laughed. I lay down beside him, and pulled off his rubber and put it on the floor next to the mattress where I had tossed mine.  
I pulled him into my arms, and held him until we both fell into a sexually satisfied sleep. He jerked awake, and sat straight up next to me. “What time is it?” he asked as he leaned over my naked body to see the clock on the floor next to us. “Oh my god, I’m going to be late to class.” as he vaulted out of bed. He grabbed his boxers, and wiped my cum off his face, chest, and ass. He pulled on his jeans, and grabbed a dirty t-shirt from one of the piles on the floor. He shoved his feet in his sandals. He slung his backpack over his shoulder, and opened the door. “If you want to use the shower, help your self; just lock the door when you leave. And . . . Thank you, I hardly ever have sex just for fun, that was nice.” And then he was gone. I could hear his feet hurrying down the wooden stairs, and then there was just the sound of the building settling. I rolled off the mattress, and walked to the shower hoping this dump had hot water. I turned on the tap and was surprised, the water was scalding. I ran his bar of soap over my body thinking of him, and finished off by shooting one more time down the drain. My cock was getting sore, that was my fourth time, and it wasn’t time for lunch yet. I fished a towel out of a pile on the floor, it didn’t smell too bad, and so I dried off. I hoped he wouldn’t mind, as I borrowed some of his deodorant an applied it my underarms. It turned me on just touching them. I had never had anyone lick them before. I rounded up my clothes, dressed and left, making sure his door was locked. I didn’t leave him the fifty dollars, somehow that would have been wrong. 
 I just couldn’t get that kid off my mind; I would catch myself going out of my way to drive down his street. I was hoping that I would just see him walking home from class, just catch a glimpse of his sweet face, or his lithe tight body. I would lay awake at night remembering what his tears tasted like when I kissed them away, and what his boy hole felt like gripping my throbbing cock when we made love. Yes, I thought of it as making love, not just having sex or getting off. I was afraid that I was just having a midlife crisis; after all I was old enough to be his father, hell, possibly his grand father. This kid could not possibly have any feelings for me, yet, I wanted to be with him again. I mean, I don’t even know his name. I know that I could have him for a price, he needed the money. But, I didn’t want to cheapen this relationship I had in my head with him by paying for sex. I mean, you pay for sex, right, not for love, and I wanted his love. I wanted to love him. 
About two weeks after our first meeting I decided on a plan. During the day when I knew he was in class, I drove to his building, and knocked on the manager’s door. A thirty something man came to the door, shirtless, showing off his tattoo of a large bird on his hairy chest, and with a smoldering cigarette dangling from his mouth. He was barefoot with long yellow toenails, and dirty cut off sweat pants. Even though I could tell that he was not wearing underwear, I did not get turned on. There was nothing sexy about him. I explained that I wanted to pay the next months rent on apartment nine on the third floor, and I needed a receipt. I would throw in an extra fifty, if he told the young man that lived there that an old woman paid it for him. “Yeah, dude, whatever. I would tell him the Easter bunny paid it for fifty dollars.” He said around that stinking cigarette. I had to fight the urge to go up the stairs, just to touch the door to the crappy room where he lived. I went back to my car, an empty feeling in my stomach, and drove away. If I really loved him, I could do this. I could help him without expecting anything in return. Oh, but I wanted him so badly. I hurt inside just being away from him. 
I still kept driving by every chance I had. I wanted so bad just to see him, and then, one day, there he was. He was walking down the street with a guy about my age. He had his backpack over his shoulder and was saying something to this guy and pointing toward his building. The old guy was bald, a little more than overweight, but less than fat. He was acting very nervous, kept looking around, and over his shoulder. When they got to the door, they stopped, and the kid said something, and the old guy handed him some money. They turned and went into the building. I drove on. I tried to not think about what was going on up there. The thought of him doing to another man what he had done for me was too hard for me. I knew my plan was stupid. I had to do something that would end this suspense, I had to have him, or I had to get over him. I had to stop thinking there was a possibility that we could have a relationship, or I was going to have a relationship. 
On Saturday morning, I went to his apartment. I knew he didn’t have class, and was hoping I could catch him before he went to “work”. I hiked up the stairs. The building was quiet, and the smell was worse than the last time I was there. I hesitated outside his dirty scarred door. The paint was yellowed and chipped, and rattled in the casing when I knocked on it. I had to knock twice before I heard the lock turning. The door opened a crack, and I saw his eyes peeking out at me. ”Yeah, what do . . ., oh, hi” he said as he recognized me. “Hi.” I said back. I really didn’t know what to say from there. “Can I talk to you, would you like to go out for coffee?” I said improvising. “That sounds good, come on in while I get dressed.” He said while he unhooked the chain lock, and opened the door. He was shirtless, wearing baggy boxers, and white half socks. “It’s ok; I’ll wait downstairs while you dress.” He smiled, his soft red lips turning up at the ends, and his deep dark eyes sparkled. “You’ve seen me in less than this.” He said as he picked up a pair of jeans off the floor, pulled them on, doing a little jump to pull them up. He pulled on a worn white t-shirt, and stuffed his feet into an old pair of grey tennis shoes, ran a brush through his shaggy hair, and announced, “Ready.” I couldn’t help but smile, he was so damn cute. I wanted to kiss him so bad, and my balls started to tingle. We walked to a local coffee shop that was used mostly by college students. We ordered our coffee, and went out on the back deck that overlooked a small parking lot, and a smelly green dumpster. He stared down into his cup blowing softly over the surface of the steaming black liquid. The steam from the cup encircled his cute boy face, and his long dark eyelashes hid his deep dark eyes from me. He looked shy, not something you would expect from a boy that sold sex to pay his bills. He looked up, those eyes looking deep into mine, almost reaching my soul. “You wanted to talk to me?” He said. It was almost a whisper. 
I decided to just tell the truth. “I can’t stop thinking about you, I find myself driving down your street just to catch a glimpse of you. I’m starting to think of myself as a stalker. I just need to know, do you ever think of me?” he took a sip of his coffee, looked back down, giving me that “shy boy” look again. “You know what I do man, alright. I lie to guys for money. I tell them that I love them, that they are a stud. I tell them that their cock is the best I have ever had; I tell them that for the money man. I not only sell my body, I sell lies too. If I told you how I felt about you man, how would you know if it was the truth, or just to get some cash from you?” I knew what he was talking about, I wanted to help him, I wanted him to stop having sex with other men, yet, I wanted him to make love to me. If I helped him pay his bills, was I paying for sex? We would never be sure where we stood with each other. Was he lying when he was with me, and just after the money? He would never know how much I loved him as long as I was paying for “it”. “You know, I think over some time I will be able to show you how I feel about you, and I will know how you feel about me. I will just have to trust you. Now, do you think about me?” He looked at me for a minute and then asked, “You paid my rent for me didn’t you?” “Yeah.” I said. He looked back down and said, “I was going to have to let that skank fuck me for my rent this month. I had midterms, and couldn’t get out and earn enough in time to pay him. I really owe you man. He’s gross.” 
 “The point is, you don’t owe me. I did it because I love you. I didn’t do it so you would have to “do” anything.” 
“You mean that you don’t want to have sex with me?” 
“No, I don’t want to have sex with you. I want to make love to you, and I want you to make love to me, but . . . only if that is what you want, what you feel.  I don’t want sex. I want more, so much more, I want your heart.” 
The tears started then, not just one, but a wash of them down his unshaved cheeks. "Yeah man, I think about you. I can't stop thinking of you. You were the first person I have had sex with just because I wanted to. Not because I had to. I don’t know if I can give you what you want. I mean, love. I’m not sure what that is, no one has ever loved me, and I have never had someone to love. I want it though. I wanted so much to see you again, when I opened the door, and you were there. . .” His voice trailed off, he couldn’t talk through his tears any longer. I placed my hand over his, and said, “Let me walk you home now, ok? You need some time to think about this.” We both got up and headed toward his apartment. I couldn’t help myself; I reached down and took his hand in mine. He leaned in closer and placed his head on my shoulder. When we arrived at the door to his building, I pulled away to leave. “No, please don’t leave me.” he said, his deep wet eyes pleading with me, his hand gripping mine. “I think it would be best. I want you too much right now. It wouldn’t be fair to you if I stayed. We both know what would happen.” I couldn’t believe I said that, because I wanted to go upstairs with him so bad. My cock was hard and leaking in my pants just being close to him. “But I want it to happen, do you understand, I just want to be with you, now.” He said, leaning in to me and pressing his hard little cock into my body. “See, I want you, I want to make love to you, and I want you to make love to me. I need it. I need you.” I wanted to be strong, and insist that he take some time and think this through, but when I felt his need pressing into mine, my resolve broke, and I opened the door. 
When we closed the door to his apartment, I took him in my arms, pressed his lips to mine, our bodies tight together. It was my turn to cry, tears ran from my eyes as I held this boy god, and knew that he wanted it, he wanted me. He pulled his head back and looked at my wet face. At first he just looked puzzled, but then he smiled a knowing smile. He pulled his shirt off over his head and stood bare-chested in front of me. I had been wrong before, he was naturally smooth, he didn’t shave his chest. His nipples were hard, and when I pulled him to me I could feel them through my shirt. My hands traveled over the soft warm skin on his back, down under the waist of his jeans and boxers and over the wonderful tight globes of his young firm ass. I pressed him tighter to me, and felt him start to hump my groin. One of us moaned; it may have been me. He backed off again and started unbuttoning my shirt. He pulled it loose from my pants, and slid it off my shoulders. We held each other again, feeling the warmth of our flesh, our hands rubbing, touching. He pulled away and walked toward the bed, stopping, and facing me, he undid his jeans, pulled them down with his boxers, and stepped out of them. Naked, except for the dirty half socks on his small feet, he climbed onto the mattress. He lay on his back, legs spread, and that cute little cock sticking up toward the ceiling, a drop of pre-cum leaking out of his slit, dripping off the red little head, and down his shaft.  
I walked to the foot of the bed, reached down and took the sock off his right foot, placing my lips in the arch, I kissed it. Slowly, I moved my tongue toward his toes, licking the ball of his foot before taking each toe into my mouth and sucking it. This time he moaned. I ran my hand up his hairy calf, stopping at his soft inner thigh. I then moved to his left foot, kissing my way up his leg until my head touched his balls. His hands came to the back of my head, and guided me to his throbbing boy meat. I licked my way up his little shaft, kissed the pre-cum off his hot ripe head. As bad as I wanted to take him into my mouth, I pulled away, and stood up at the end of the bed. I looked down at his perfect naked body, and into those deep, dark eyes, watched his chest rise and fall as his breath came in short gasps. I undid my belt, unfastened the button on my khaki pants, and slid down the zipper. They fell to my feet with the weight of the stuff in my pockets. I used my toes to pry off my shoes, stepping out of my pants and standing in front of him in my black boxer briefs, and socks. I took off my socks, and slid my briefs down my legs exposing my hard, throbbing, dripping, cock. He held his arms out, reaching for me, his eyes begging for me.  
I crawled up the bed and slid up his body, our hot skin touching, our throbbing meat rubbing together. I took him in my arms, rolled onto our sides, pulled his face to mind and kissed his soft young lips, sucked his hot excited tongue into my mouth, my hands roaming freely wherever they wanted. He pressed tighter into me, our pelvises pressed together. He started humping me, our tongues working feverishly in each others mouth. One of my hands was on the back of his head pressing his mouth to mine; the other was on his smooth, tight ass, pressing our cocks tighter together as I started humping him. My god! It felt so great, I was actually feeling dizzy, and it was almost like having an out of body experience. His hands were on my fuzzy butt, passionately kneading my ass cheeks, and pressing me tight to him as we dry humped like rabbits. I couldn’t believe the feeling; it started deep inside like nothing I had ever felt before, rising, growing, and expanding inside. My cock was harder than I had ever experienced, and it felt like it was going to explode, and in a way it did. A huge load of hot white cum shot out with such force that I thought my slit was going to rip. I yelled out, screamed like a girl, as the overpowering feeling of the most intense orgasm I had ever had. And  . . . it didn’t stop. It wasn’t just more shots of cum spewing from my cock, but separate orgasms as the largest load of my life shot out burning our skin. It was so hot. Lost in my own pleasure, a pleasure I had never felt in my life, it took me a second to notice that he was crying and whimpering as his load mixed with mine. We continued humping our bodies together, the hot thick cum making sucking sounds as it slid between our spent cocks. We pulled our mouths off each other, gasping for breath, a dazed look in our eyes, as our brains registered what had just happened. As my eyes started focusing again, I noticed he was staring at me. Those deep dark pools probing me, he smiled, and said “My name is Jamie, what’s yours?” 
                                           EPILOG 
I looked over at the handsome man next to me in the car. We had the top down, and his hair was blowing freely. We were heading to a B&B for the weekend.  It was hard to believe that we had been together fifteen years. Jamie had graduated, gone on to get a master’s degree in psychology. I helped him open his private practice using my retirement to do it. He worked with boys and young men struggling with their sexual identity and guys trying to escape from a life of prostitution or porn. I worked with him as his business manager. At night we still made passionate love to each other. I am happy to say that I have never had sex once in those fifteen years. I loved him with all my heart, and I knew that he loved me. That is why this trip was so hard. I was going to need to find a way to tell him that the doctors said that pain I was having was cancer, and our time together would be over soon. 
 
 
 Publication Date: November 4th 2011 https://www.bookrix.com/-shyoldguy