The Great Gay Uncle Lenny

I have one brother; Victor is 5 years older than I am. He and I were never really close, so growing up; I always felt alone. He usually ignored me, or treated me like I was a pest, so I usually tried to stay out of his way. We never really did very many things together, unless it was a family event. Nevertheless, I always wanted to be like him because he was very adventurous, funny and did lots of freaky things and I had to sneak around him to see what he was to do next and he never seemed to be happy with my spying steps.

I still remember the first time I saw him masturbating; I’d seen him naked before, and even with a hard on a couple times, but I’d never seen him playing with his dick before. One afternoon, when I saw him heading out to the small shed we had behind the garage; I knew he was going to do something fun and I snuck off after him, quietly into the garage and up to the door in back that connected to the shed. When I finally peered around the corner of the workbench and through the door, there was Vicky standing facing a table to the left with his jeans and briefs down around his ankles. He was jacking off, rapidly stroking up and down his hard dick. There was a rag laying on the table in front of him. I was stunned because I’d never seen anyone do anything like that before, and had no clue what he was doing.

I felt my dick beginning to get hard and it felt very good when I fondled my stiffy. Just instinctively, I reached down and began squeezing my bulge and kept watching my bro pumping his cock, gradually going faster and faster. Now he was sweating and his face was red as a beet as he was now truly ravaging his cock. Suddenly, he exclaimed “Fuck!” and gasping, he leaned a little closer to the rag on the table, and then some white looking thick liquid squirted out of his penis, splattering all over the rag on the table. Mike groaned a lot a he squirted again and again, before finishing it all and eventually stopped, as a dribble of the white slush oozed out, running over his fingers and dripping onto the cloth. Vicky stroked himself a few more times, then with a big smile, he folded the rag and wiped his dick and hand with it. I ducked quickly under the work bench, as he pulled up his pants, and walked past me out of the garage whistling to himself.

After he was gone, I snuck into the shed and found the rag laying twisted up under the table. I pulled it out and opened to examine the white stuff Vicky had squirted. I was not able to figure out what it was, or why he squirted it, but I figured if he could do it, so could I. So I looked around, and seeing no one, pulled my pants down and assumed the same position and began to imitate the moves. It felt good and I kept on going. Suddenly, I felt as if I was going to pee and then suddenly the feeling stopped and nothing came out. Although it felt awesome but I was upset that I hadn’t squirted like Vicky did. I put the rag back, pulled up my pants and left. After this watching him closely I found out that he jerked off a lot in the shed, in the cellar, bathroom and even in his room. Truly I did not see him masturbating in the bathroom but the moaning, wheezing and gasping noise; I could hear outside, were the clues for me to believe it. Of course, I continued playing with myself and enjoyed the wonderful but dry feeling for another a few weeks before I also began squirting like the tremendous force of a fire hose enjoying my orgasms.

Soon, I made friends with a blond boy named Daric, who lived a couple blocks away. He had a brother who was about 2 years older than him. There were woods behind their house, and Daric and I built a kind of fort back there with some old boards his father had. One day we went to play in the fort and found a couple of Hustler magazines hidden in it behind a wall board. As we were looking through them, Daric said, about a week ago he had seen his brother Daniel coming out of here and probably these magazines belonged to him. He told me the details of seeing Dan; jerking off while he was hiding exactly behind the little old sofa pushed in there. I was hard as a rock, and noticed Daric also adjusting his crotch. I told him; how I’d seen Vicky doing the same thing many times. Daric asked if I had done it and I blushed but admitted it. Daric also admitted and asked me if I felt like jerking off with him right there. I hesitated, but then agreed and he immediately started pulling his pants down and I pulled mine too. We were both looking at the tents our very young hard erections were making in the briefs, and giggling. Then Daric pulled his briefs down and showed me his and I pulled mine exhibiting mine.

It felt great having someone else touch me when he came close and held mine in his fist making me do the same for him. After a few seconds he released my cock, and I let go of his, and we began masturbating ourselves. Watching each other was a tremendous fun but it took us hardly 2 minutes to spill our juices. Coming back from the intensity of our orgasms, we both agreed that it was awesome fun, and that we should do it again soon. That was the start of a mutually satisfying sexual relationship between the two of us that lasted almost 6 years until Daric’s dad got transferred faraway and they moved but during this long time we had experimented with every imaginable sexual activity together and supported each other being gays. We were in love but of course not romantically but sexually only.

It was painful that I lost quite a few years of my studies trying different endeavors and Vicky not only finished his studies but also married and became a father to a beautiful little boy Shawn. He was living hardly a few block away and so Shawn became very much attached to me other than his parents. In fact, we two were always very happy playing and doing things together so much so that I would feed him, change him and even bathe him very often when he was little, Of course it was a very special and unique uncle and nephew relationship between us and though my brother never said anything, but I could feel that he was surely jealous that his son preferred me to him.

Good that Vicky and his wife had another son few years later and I kept my due distance allowing father and son to develop the bond and everyone was happy. For all the growing years of Shawn, I got to see him very often, took him to his little league games and even did much stuff like going out; just two of us at least once a week. Grown up as young adult he was also welcome to visit me in my apartment even for sleepovers on weekends if he desired. It got so that Shawn wanted to do it every weekend and I smelled Vicky being upset again. To avoid any problems, I backed off a little but just a little. Being gay, I realized this was probably my only shot at having a child in my life and I did not want to lose him. It was great that Shawn’s younger brother was growing up fast too taking more and more of Vicky’s time, making all things even out allowing I and Shawn to spend even more time together without any concerns.

One of the most difficult and painful time I remember when Shawn had his first wet dream and he was extremely scared because nobody had spoken to him and told him until I noticed him being uptight and I explained everything to him with very caring and loving words. Of course he felt much better and thanked me for talking with him about it. From then on, whenever he had any questions, of any kind, he would come directly to me. Perhaps the worst was the time when my employer told me they were closing the office at this location and offered me a very nice package of salary and benefits if I moved about 3 hours away. It was a great offer and I just could not refuse but when I spoke with Shawn, he begged me not to move and stay with him.

After many long discussions, I was able to convince my nephew Shawn that I had no choice and shall visit him at least once a month and we finally came to terms. Initially my move was very hard but one day at a time and thankfully most things settled fine. I visited Shawn and my brother every month plus there were a lot of phone contacts. Time flies and 3 years had passed; Shawn was allowed now to visit me and stay over the weekend but only every other month in addition to my visiting Shawn every month.

Once Shawn came visiting me and I could tell; he had something on his mind. Since I was all alone here so far away, I had rented a one-bedroom apartment only and whenever he came we slept together on the only one queen size bed I had and we snuggled up rubbing against each other just like we always did since he was a little boy. This particular night we were laying together with lights switched off and I had heard him sigh loud enough for more than a few times. This is when I asked him, what bothered him and he was extremely reluctant to talk but then he told me that his father, my brother told him that to his belief I was Gay, Shawn had his eyes almost wet when he told me, ‘Uncle Lenny it is not important but even if you are Gay, our relation would not be spoiled’. I did not understand what he meant and Shawn said all loudly that our relationship would not be spoiled because he was Gay too. A dim moon light from the street was coming into our bedroom and I saw his face with wide open eyes when I pulled him over me in a tight hug and repeated his words, nothing will ever change, even if you are gay. He buried his face in my chest and wrapped his arm around me as I heard him, uncle Lenny I love you very much and asked me if it was true and I was gay? I had no way to refuse and I reiterated to love him no matter what while kissing his forehead.

As we lay there quite for a minute, my curiosity was killing me and I asked him, why his dad say this about me and did he know about Shawn being gay. Shawn told me that his dad had asked him to go for fishing with him which Shawn refused making his dad angry and asked why I never played any sports or did anything manly but acting like a gay. I also got upset and answered him right there that yes I was gay; to which he added, no wonder you are so close to Lenny. He has never played any sports as well, never had a girlfriend, never been seen to do manly activities, just like you. I could not do much but did ask Shawn, if my brother really did say all that and Shawn told me of course his dad did say all but added, uncle Lenny; it does not matter at all. I do not have much relations with him already and I do not care. All I need is you because you are far better than my dad, honestly.

We were quiet for the next almost half an hour and perhaps he dozed off breathing very rhythmic but I was still wide awake. His body was almost half draped on me when I was harshly pricked in my thigh by his erect solid cock. I am sure he must have been dreaming of something very good to achieve such large hard on. Of course I also did not take much long and was erect like a phone pole. Suddenly Shawn slipped off me as I took my arms off him, gave a deep sigh and started breathing steady again but I was wide awake and surely was not going to fall asleep anytime soon. The utter hard erection was rudely compelling and I sure needed to jerk off. As quietly as possible to not wake up Shawn, I moved very little to reach for the tube of lube I had put in the drawer next to the bed, pushed my boxers down to the ankles, poured the lube into my fist and wrapped my slimy hand around my wand and began stroking myself up and down. Hardly a minute passed and I saw Shawn move making me freeze in action hoping he will continue to sleep but I heard him whisper instead; asking for the lube. Without waiting for me to bring the lube to him, his hands pushed his boxers completely off him chucking it to the floor and an audible Please. I was not sure what to do but then I looked at him already fondling his hard cock. I gave him the tube and next second he had put some on his serpent head and began gliding his hand on his length spreading a thin layer all over his marvelous length.

I could not resist and pushed my boxer off my ankles and now we were stroking ourselves as if a competition was on. Not even a minute into it I realized one of Shawn’s leg pressed against mine increasing the excitement of the moment by hundred folds. We were both matching each other’s rhythm but Shawn was breathing stronger and steady than I; uncle and nephew next to each other pleasuring ourselves. There could be no doubt when a very clear voice was heard offering to do it to each other and without the lapse of a moment, my hand was pushed off and Shawn had grabbed my stiff as steel shaft. A groan dissolved in the air as he started stroking me. My beloved nephew was doing me so grandiose making me lose all dithering and soon I was reciprocating him stroking his cock as sensuously as I knew and could, our tempo exceeding and dropping, both trying to impress the other with all the skills and techniques polishing the rods; making me realize that I was getting close and Shawn was also breathing heavier. Soon I felt Shawn’s leg that was pressing into me became very tense and tremendous heat radiating from it.

I felt my orgasm boil in my balls as quickly too but right then his hard muscle in my hand flexed huge with an uncontrolled gasping coming out of his throat and without a doubt I could see a large glob of his manly brew fly out of the cock hole, making some high flying moves and fell back on his torso splattering and sending a drop to hit my hand and back of the palm. That proved to be the straw that broke the camel’s back and with a very loud groaning my dam broke. We both knew what and how, continuing the jerking off applying variant pressure on the areas of the shaft, finger scrapping under the balls and milking the balls also to the best possible level. Our bodies tensed together producing the pleasures of mutual orgasms and the euphoria extended a little longer as I felt but then the rush was over and we both came back to earth.

We were both still holding each other’s manhood as the last bit of our nectar drooled out of our pee slits; when Shawn declared to have enjoyed the best orgasm of his life and I also endorsed his thought. I reached for the disposable moist towels box and we both cleaned ourselves. Soon, totally naked; Shawn rolled into me again and I wrapped my arms around him before falling deep sleep soon after repeating, I love you, words.

When I woke in the morning, we were both still in pretty much the same position. Shawn was still sleeping, snuggled up to me. His cock was hard again, and pressed against my thigh. Mine was hard as well. Shortly, he woke up, and rolled off of me, onto his back and began stretching. He said, he was glad that things worked out fine and to my asking he explained that we knew about each other’s sexual orientation and I assured him that I was glad that he came out to me and he will never feel to hide anything from me. I was amazed to hear when Shawn said, he was not hiding from me anything ever and was ready to be my boy toy and learn all and everything from me and shed off being virgin. Shawn told me of having seen some gay videos making him savvy and know a bit about boy / boy sex and had often masturbated and now he was almost begging me to take him under my wings and train him to serve the men out there who need young boys for their extra- curricular sexual activities.

It was a true feeling when I reminded Shawn that I was his uncle and we must not cross certain limits but I was stunned when he said,” oh fuck that, we have crossed plenty limits already. Hell; you are also being more like my father. So far you are the only one who has taught me all I know about life and I tell you; you will be the only person who will teach me about the best sexual pleasures of Gay life”. I felt so proud that Shawn was showing such a level of confidence in me, knowing full well that I shall never hurt him; but other men might. I was almost sure; I was blushing but had a big smile when I agreed to do the needful and Shawn nailed the deal saying that he knew: I wanted to do it as much and as best as he did because I had the mother fucking huge dick hanging in front of me and I only chuckled, what another choice I had!!

Shawn was laying with his head on his arms, he looked beautiful. Nice thick eyebrows, blue eyes, soft facial hair getting ready to grow out, big trusses of hair in his arm pits and very hairy legs that are always nice to hold by the ankles to raise them up making the tight boy holes to show clearly for breaching the security barriers and enter in full force. I could not resist anymore and reached over to stroke the long thick hair on the inner side of his satin soft upper thighs; making him giggle as my fingertips brushed his silky skin. Slowly my hand touched his hard erect dick. In the day light I could clearly see he sure had the family genes showing in his size of no less than 7” at least and throbbing as a result of high blood pressure running in his shaft. The thick base of his man piston was firmly nestled in his pubic bush. His weight balls hung loosely in the nut sack, dangling towards his well curved ass. I made sure to tell him that he had the awesome family genes giving him the pretty big size everywhere it was needed making him chuckle and feel confident.

My cock was getting horribly stiff that was almost hurting and I needed time to think over about my next course of action with Shawn and making an excuse I got off the bed and went to the bathroom. Sitting on the commode, shaving and brushing my teeth; I was constantly thinking about the strategy of how to get the horny boy under me and enjoy him without hurting his tight puckered virgin ass and not damaging or destroying it with my Weapon of Ass Destruction. Entering the shower stall the water was cascading over my horny body but I was still in deep thoughts; my hands began soaping up my body and then like in the movies, I felt a pair of extra hands fondling my balls and running on my ass. I was about to spin around when I felt Shawn’s fingers delve deep in my ass crack and reach my anal lips sending shivers all over my body. Truly I had been a top only, in my gay life so far and honestly I had never allowed any of my fuck buddies to sneak in on the anal orifice of mine like this but this was a special case but I knew, I was not going to allow the young nephew of mine to have concocted a naughty plan in his brain to fuck me and this be the starting point for all the following activity.

I heard him wanting to help me wash and took the soap from me, while the index finger of his other hand began massaging my asshole. With gentle pressure he turned me around and make me bend slightly at the waist; attempting to spread my ass cheeks, rubbing the soap bar in it. Making decent amount of lather he switched back to finger massage my ass orifice with one hand while reaching with the other to masturbate me with soapy lather. It was nothing new but Shawn doing it to me, Oh my God. It took me hardly a minute and it was impossible for me to withhold the rising tides of the orgasmic onslaught. Shawn continued pleasuring my cock and anal opening; making me growl and roar like an animal, while I painted the shower walls with my semen. He kept massaging my dick and ass until he was sure that every last drop of my juices had cum out and then he rinsed me well. As my breathing became normal, I looked at him saying; and you wanted to be trained and learn about the pleasures of gay sex?

He snickered but sounded very serious and asked me do him now. Looking in his eyes and seeing such deep request; I had no nerve to refuse and turned the shower head onto him till he was all wet. Then I shampooed him and later took the soap bar, paying a very special attention to his erected extension and the little ass with tiny hole. Soon his orgasm was raging out of control but I stopped and started rinsing him with his face being red in an awe and a hurt look but I force turned him around facing the wall pushing him gently against it. Then I squatted behind him and pulled his hips to me bringing his ass to my face. Without allowing him to resist or say a word, I slowly began licking between his bubbles as I heard him sigh loud. I kept licking around his hole for a while and then directly over his hole. Now he was moaning constantly and I was rimming his anal eye with a gusto. My warm breath and the saliva was dilating his balloon tight ass puckering allowing the tip of my tongue to literally enter into his knot like a spear.

Shawn’s body trembling in my hands and a slur of ‘Fuck meeee Godddd’ flowing out of his beautiful lips. I showed no dereliction and kept tongue fucking him for another a minute or so before gently removing my tongue and slowly turned him around with his throbbing cock exactly at my lips. Aahhh!! Uncle Lenny, that was simply awesome, he complemented me and I smiled back in acknowledgement. Next second his low hung balls were sitting on my one palm while his shaft was wrapped in the other hand and quickly sucked in my wet mouth. Pressure sucking like a vacuum, soon he was completely lodged into the back of my throat like a wedge while I moved my head and neck, up and down and even sideways to bob and send sucking sensation all the way deep into his balls. With the increase of my enthusiasm on Shawn Junior, now I had extended one of my finger to poke, scratch and even enter his well relaxed ass hole to finger fucking him. As I continued working on him front and back Shawn moaned louder and louder, soon whimpering with deep ecstasy ripping his insides surely leading to orgasm very soon. It was less than a minute of my finger deep dipping his hole hitting his prostate and my sucking ability working his cock that he shuddered with a forceful bucking of his hips and I felt his anal clamp tight on my finger, his body tensing and my mouth filled with the warm youthful cum of his.

With repeated cries of uncle Lenny, Shawn kept filling my mouth with his cream almost as fast as I could swallow over and again. As I noticed his legs trembling, he was holding my ears very tight making sure his weakening knees don’t suddenly collapse making him fall over me. Finally, he announced the end of the roller coaster ride when he uttered that it could not be any better and I stood up reaching around him with my arms and jamming my lips on his and my tongue laced with his tasty juice transferring onto his taste buds.
Once again he smiled and announced that this was the most awesome he ever felt and whispered quietly in my ear asking me if I was going to fuck him now and added a long please to increase the pressure on me. I whispered back confirming that he did want to learn all and that too this soon and feeling him hug me even tighter; which I took as a yes answer and I think I saw a thankful wetness in his eye when I very carefully picked him up, his still semi solid man meat poking into me as we walked out of the bathroom back to the bed for the finally as asked by my very dear nephew Shawn.

On the bed I laid on my back and Shawn quickly took a kneeling position besides me such that I gave him a good head and also licked his soon to be fucked ass all around while he gave a nice service to my cock, stoking, sucking; worshipping my balls too. What an irony he called me a cocksucker and I gave a consenting smile in return. Next second I had him pulled by the hair and pushed down while I gagged him a bit attempting deep throat while he guided my groin but still talking dirty to me, even calling me faggot and a slut. Putting him on his fours, I got behind him holding the lube tube and pushed my hard cock between his lower cheeks, just a little to tease only asking if he needed it all the way inside him and he kept saying yes like all the bottom faggots do, pushing his legs apart; allowing me to rub the lube on and in his anal opening while he looked over his shoulder giving me the lusty looks. I gave a confident smile, splayed out the rapidly flowing pre-cum on the brutally stiff cock shaft while kept slapping his ass globes with my hand as well as my fucking bamboo. Suddenly pushing down hard between those almost fully grown shoulder blades forcing him face down onto the pillow; I had Shawn’s ass up in the air, all vulnerable to my fucking dong, open and ready for my burly fucking machine between my thighs.

Stretching my body all over him, roughly I held his head down into the pillow, used the other hand to spread his ass to get inside him telling him to remember he was my bitch boy, ordering him to relax and push his hole out offering it to my fucking muscle. Pushing my hips was building pressure at his virgin, very scared opening and his face being shoved into the pillow was making him hard to breathe raising the panic level, I slapped his white ass buns as rough as I could, yelling at him to push his ass out for my fucking pleasure. I could feel him doing his best and his tight tiny ass hole huffing to jolt open the entrance from inside out. I removed my hand that was pushing his head and now with both hands pulled his cheeks apart while maintaining the hip pressure for the fuck pole to push inside. WOW!!! My cock broke through his ass ring. I could see bitch boy shivering and quivering with pain; his whole body had suddenly been flooded with sweat oozing out of each pore on his skin, but I knew it was even brutal, not to gain full entry and just keep stressing, stretching his ass ring with my monster cock head. Shawn, my love child kept crying, appealing for mercy but grabbing his hips I pushed my waist forward and the boy shouted, feeling his ass getting slaughtered and mounted on my rod for being roasted inside out. He was in pain, real cruel pain but now my hard meat had established its place and I was sliding in him at will, though feeling the chute extremely tight. Constant cries of pain and ass being distorted, reshaped to an adult size was rather exciting me to increase the pressure and not make the crucial mistake of pulling out because the misery of an empty ass is far more hurting than the agony of feeling stretched and full.

I stopped for a moment and told Shawn to quit being so tense and just take it like a man, relax and enjoy being fucked for our mutual pleasure. I could feel the boy unwind a bit and I pushed in even harder to satisfy my personal pleasure. My hard grip on his shoulders was not letting him even try to detach from the love joint and then I felt my cockhead reach the deepest end of boy ass. I made sure reaching home by grinding my groin on his ass to make sure I was in to the hilt and then stopped. Having fucked plenty virgin and used ass, I knew the drill and had to give his ass breathing space to get used to this opening and insertion stage before starting the fucking mechanism. I could feel Shawn making some odd moves on my shaft; adjusting himself and then calmed down reasonably, sending me a signal that I could start the next level. Lightly grabbing his hips to keep him steady at his place, slowly I started wrenching in reverse and pulling back; sending Shawn in the panic mode with the brutality he felt in his rectum, thinking that I was upset and pulling out of him being angry. I tapped lightly on his ass cheeks and also briefly patted with the other hand on his awesome round rump and leisurely; very slowly kept withdrawing till well over half of my shaft was out of him and before he stopped protesting; I switched the gear already, pile driving hard and rough all the way in his ass once again.

Don’t panic now and stay calm; I am going to fuck you hard now, I announced with a delay of about a second after jamming my piston in his warm cylinder, to which he nodded as an acceptance and I started the jet engine to propel the missile forward and back, north and south, steadily increasing the tempo and range of motion. Shawn made all the noise, he could make but like it is supposed to; soon all the hurting and aching he felt in his anal canal had converted to pure ecstasy and Shawn was trying to match my fucking efforts in his ass but I held him in place, still and immobile giving me the benefit to ram slam into him as hard and rough as I needed to satisfy my selfish sex. Shawn’s head was tilted a little to the side, like any honorable bottom would be in his position allowing me in complete faith and accord to fuck him the best to my cock’s desire. What a welcome and lovely change in as little time as possible; Shawn was asking me to fuck him harder and faster, faster and deeper, deeper and harder, being a proud bottom trainee.

The constant raw friction was almost making his ass tunnel burning hot and my cock was being roasted in it but surely sending all the best feelings too that anal sex could generate. Shawn was making it a very memorable event as he kept constantly asking me to take his ass, fuck him and use him all I wanted. Almost inadvertently my one hand slipped down to his thigh and it seemed as if I had touched the helicopter fan in reverse. His rock hard cock was going round and round as I fucked him nonstop and he kept impaling and circling his ass back on my cock. Soon I had brought my other hand down too and was masturbating him while grabbing his balls immobilized in my other palm. What a Kodak moment!! The scene was no less than any extreme hard core gay fucking in gay videos. We were both honestly attempting to satisfy each other but as all good things must come to an end, it was decently long but could have been a bit longer, if at all possible and Shawn gasped suddenly and I felt his solid cock meat push against my palm as it expanded in width size and I felt a flow of liquid fire engulfing my hand completely in as short a moment as ever possible. He ejaculated his sperm like a cannon shoot marking all over the bed sheets. His tight squeezing ass meanwhile did a brutal number on my cock stalled inside him and of course in a jiffy my orgasm peaked as well and before I could decide or ask him if I could pull out and shoot in his mouth, I squirted my seed so hard in his ass to reach the deepest ends to breed him. After I had cum completely coaxed with the efforts of Shawn’s fuck torn ass, I stayed in him and just kept laying on him as he collapsed onto the bed.

Slowly as my cock softened and dropped out of Shawn’s ass, we had caught our breath and then he turned facing me. We kissed very passionately and he thanked but also was complaining and grateful at the same time to introduce him to this awesome side of sex which men play as much as they wanted without the fear of any unwanted results and also hoping that he would not feel this much torture in his ass, every time he got fucked. Being a good nephew he asked for permission to offer his ass to other men in need if I had no objection and sure I happily consented to his desire knowing well that I could not survive much longer, only fucking my dear nephew for the rest of my life. We fucked for couple more sessions during the day and next day; Sunday, before he was ready to go back home but we had made plan to continue our rendezvous even if it was not approved by our elders and the stupid society around us.

The End