Boy Story

I was going through some hard times recently. My job was cut during the recession and I was trying to get by on the meager unemployment check I received. It didn't help that I had a bit of a gambling problem. I was badly in debt but pretty much judgment proof so I didn't worry too much about it. Sometimes I would take my weekly check to the casino on the edge of town and more often than not, it would be gone in a few hours. Recently, I have been going over to my neighbor Gary's apartment and making bets with him and some of the other people who live in my building. Gary was more flexible when it came to things like letting me pay him back later. We played for small amounts of money so it was never too big of a deal.

Most people would not expect Gary and I to be hang out together. Gary was significantly older than me. He was a tall, overweight man whose balding head contrasted with the fuzzy chest hair that stuck out from the top of his shirt. Compared to him, I was much younger with a slim and smooth body. While I was shy and quiet, Gary was loud and boisterous. If it had not been for the gambling, I don't see why we would spend any time together.

Things got weird one day when I was over at Gary's apartment. We had been playing pool and making bets all afternoon. Gary was experiencing a bad luck streak, having lost several games where it initially seemed like he was ahead and likely to win. This pissed Gary off as he is a very competitive person. I could tell he was getting worked up as he kept cursing under his breath.

It is my experience that when playing a game requiring precision like pool, it can only improve your odds to play against an opponent who is frustrated and potentially distracted. So I decided to take advantage of the situation and bet everything I had won that day on the next game.

"Of course," Gary muttered after I had placed my bet. "Fucking cocksucker," he spoke in a voice that was barely audible. True to my prediction, Gary played the game sloppily and had a hard time sinking his balls.

I quickly pulled ahead in the game. While Gary had several of his balls left on the table, I only had to sink the eight ball and I would walk away with a fistful of cash. I felt I had bet smart on this one; my prediction about Gary's performance was absolutely accurate. Unfortunately, this made me a little bit cocky. When I took my shot, I easily sunk the eight ball. Disappointingly, I also sunk the cue ball causing me to scratch and lose the game. All the money I had won that day was gone including my unemployment check.

"Hahaha, are you fucking kidding me?" Gary gloated. "Fucking finally, I have been getting screwed all day."

"Fuck," I muttered under my breath. "There's no way... Come on Gary, give me one more game, give me a chance to at least win back what I came here with."

Gary shook his head vigorously, "You don't have anything left to bet. You shouldn't have bet everything you won on that last game. You've got no sense with money, kid."

"Come on Gary, you know if I lose I will pay you back," I argued. "I always have before. I got an electric bill that I got to pay and I really need the money. I am good for it."

"That's not my problem," Gary said as he rolled his eyes at me. "You gotta put something up other than an IOU. How about you suck my dick if I win the next game?"

"Come on Gary," I pleaded. "I am being serious here. I get another check in a week from now."

"Yeah, one more game, if I win, you suck my dick." Gary responded matter-of-factly. The look he was giving me creeped me out..

"Are you kidding me?" I looked at Gary incredulously. "Are you trying to make fun of me by calling me gay? I do not suck cock. Look, if I win, I get my initial pot back. If you win, I will pay you double that next week when I get my check," I explained.

"Relax, relax," Gary chuckled. "You win, you beat my cock off with your hand. That's a fair deal; I am not trying to call you gay. It would just be nice to get a good old fashioned handy."

"Whatever," I said angrily. "Stop giving me shit and let's play one more game." I racked the balls and Gary and I ended up playing another game. I couldn't help feel oft-put by what Gary said and the creepy way he looked at me. I assumed he was joking but the entire thing made me feel uncomfortable. Unfortunately, my preoccupation distracted me from the game. The bad luck streak Gary had been experiencing earlier seemed to have subsided and for the second time that day I found myself losing a game to Gary.

"Haha, I win again," Gary gloated. He placed his cue gently against the wall and sauntered over to a large leather couch that was nearby in the room.

"You win Gary," I said sullenly. "I will pay you back next week; I promise."

"Now wait a minute," Gary interjected. "You can forget about the money. The deal was that you would give me a handy. Now get your prissy ass over here and start beating my dick."

"Seriously? I asked. "That was a joke, you can't expect me to do that... that's disgusting."

"A deal's a deal," Gary interjected. "If you had won, you would have taken the money. Does it sound like I am joking? Get over here right now and start rubbing, boy!"

"This has got to be some sort of prank or something," I said in disbelief. "Why would you even want me to do this? It makes no sense." My voice grew softer and my steps shorter as I approached Gary on the couch.

"Well, what are you waiting for?" Gary said angrily. "Sit down!" he demanded, patting the portion of the leather couch next to him.

I responded submissively to Gary's commanding voice and sat down next to him. As I stood there dumbfounded, my eyes glanced around nervously.

Gary did not waste any time. He unzipped his jeans and pulled them down along with a pair of checkered boxers in one fell swoop. Gary's large, thick cock and wrinkly, buoyant ball sack came tumbling out right next to me. A large thud could be heard as the thick balls banged down against the leather. "Mmm," Garry moaned. "This is going to be good."

I couldn't believe it. I thought for sure he was going to call me a faggot at any moment and call this off but here I was sitting next to his completely exposed, bulky package. "G-Gary..." I said in tone that radiated hesitancy. "We don't have to do this."

"No, you do have to do this," Gary said aggressively. He yanked on his large dick a few times causing the shaft to quickly harden and grow even larger. "Come on and touch it boy." Gary gyrated his hips which caused his thick meatpole to swing back and forth towards me. He scooted his butt closer to me on the couch, moving the swinging, veiny spectacle closer and closer to me. "Touch it."

I blushed a bright color of red as I watched the swinging cock move toward me. Feeling as if I had no choice, I hesitantly reached towards the throbbing pole. I extended three fingers forward and brushed the tips up against the fleshy sides of the cock. I felt the cock spasm which sent a chill up my spine. I quickly pulled my fingers away. "Uhh..." I stammered.

"Oh yeah," Gary moaned. "Come on, don't stop... rub it. I am so horny right now. I'm gonna have a huge load."

"Ugh.." I didn't want to go any further but no words were coming to my mind. I re-extended my hand and fully gripped his cock. It was thick enough that my hand did not reach all the way around. "This is so... nasty," I said through nervous breaths. "It's so warm..." I ran my hand slowly and gently up and down the throbbing shaft. "There are so many veins on it..."

"Mmm... yeah," Gary moaned approvingly. "Rub that cock bitch. Your hands look so delicate touching it. It's so dirty."

I looked down at Gary's cock and was shocked to realize he was correct. My smooth, dainty hands rubbing up and down his pulsing thick cock which was pressed up against his protruding gut looked like an eighteen year old girl was giving her dad's horny friend a rub down. "Oh god..." I gasped as I rubbed the throbbing flesh.

"Those hands of yours are certainly better at working a cock than a pool cue," Garry chuckled. "Keep going, I've got a huge load coming. That reminds me, rub my balls while your down there. I really want to jizz big."

"That's so nasty..." I gasped as I reached my other hand over and began squeezing Garry's balls. They were thick and heavy and I could smell their musky odor even from where I was sitting. As my hand gripped one of Garry's large testicles, I ran my fingers through the wrinkly folds and squeezed gently and then harder. I then moved to Gary's other testicle and did the same. "They're so big," I remarked as I did so.

"Unh.. unh..unh" Gary grunted repeatedly. He closed his eyes in blissful pleasure as my hand bobbed up and down his throbbing shaft. "That's what a real man's balls are supposed to be like."

I couldn't believe that I went from having a fistful of cash a half hour ago to having a fistful of Gary's cockmeat. I couldn't help but admire how large and masculine his package was. He may have been an older, overweight man but he had the cock of a young bull. As my hand bobbed up and down the flesh, I could see sticky precum forming on the tip of its fat mushroom head.

"Unh, unh" Gary moaned louder and louder. "Ohhh shitt..." he yelled. "It's gonna happen... I am gonna explode!" His body began shivering and his cock started throbbing even more heavily than before.

"Oh my gawd!" I said in a panicked voice. I angled Gary's large cock so it pointed upward and slightly away from me but I did not let up rubbing it. I then watched as huge streams of cum began shooting out the tip several feet in the air. One of the large thick streams landed on my arm while most landed on the ground or Gary's chest or stomach. After the spurting was over, large amounts of sticky cum began erupting from the tip and flowing downward like a volcano. I felt this sticky mass of cum as it flowed down the head of the cock and thoroughly soaked my hand. As Gary had instructed me earlier, I continued to squeeze his balls and milk him of all the cum.

"Mmmm..." Gary moaned in-between hushed breathing. After what seemed like an endless flow of cum from his cock, his emissions finally subsided. Gary quickly stood up on to the couch causing his cock to be level with my face. He pushed it straight towards my mouth which caused me to quickly turn my head away. As a result, the fat mushroom head of the cock ended up pressing up against the side of my cheek, leaving a sticky cum mushroom stamp on my face. When Gary pulled back, a thick gooey strand stretched from my cheek to his drenched pole.

I turned my head in the hopes of breaking the cum stand. I was successful but it caused some of the cum to ricochet into my mouth resulting in me gagging. I tried to cough it up but it seemed stuck in my mouth so I ended up swallowing the salty mass, gulping loudly. "Eww, gross!" I complained as I closed my eyes tightly.

"I think you've got a little something on your face!" Gary laughed boisterously as he gently patted his fat cock. "Thanks for the handy, I really appreciate it. I could use someone to do that for me on the regular so if you ever feel like betting, come over here."

"I'm never touching that filthy thing again!" I insisted. My hand, arm, and cheek felt so sticky from Gary's cum. "I can't believe I did that." I shook my head in shock and quietly walked out of Gary's apartment. I couldn't wait to wash this stuff off. On the way up the stairs I realized my own cock was hard as a rock. By the time I got into my apartment, I was so horny that I didn't both washing the dried semen off of me. I beat my cock for a very long time, achieving multiple orgasms. The whole time I kept thinking of Gary's fat, disgusting cock and how it had erupted.

Over the next day or so, my mind kept going back to the handjob I gave Gary. I kept thinking about how horny he had been and how dirty I felt just servicing his fat dick. Despite my best efforts, I could not suppress the thoughts. I still did not have the money to pay my electricity bill so I called the power company and tried to get an extension for payment until my next check arrived. The customer service person kept insisting there was nothing they could do and it would be shut off if I did not pay by the end of the next day and if I wanted to turn it back on again then it would cost an extra fee. I tried various forms of pleading but nothing worked. I became concerned that my power would be shut off and I would have nothing to do but sit around and jerk off thinking about Gary's cock. I determined I had to make another attempt to get the money and to put this business with Gary behind me so I decided to return to his apartment.

When I arrived, once again Gary was the only one there. He opened the door and seemed happy to see me. "Well if it isn't the boy with the magic hands, come on in," he cheerfully spoke as he opened up the door so I could enter. "I have another warm one in the oven if you feel like making bets today."

"Gary," I said tersely. "I am going to be upfront with you, I need money. But I am not gay and I am not touching your dick again. What you had me do last time was disgusting and should be something that you do on your own free time when I am not around. If you are interested in betting for real, let me know or otherwise I am out of here."

"Sheesh," Gary said in an agitated tone of voice. "You seemed like you enjoyed yourself last time but obviously not as much I did. I don't feel much like gambling for money that doesn't currently exist. How about this, if I win, you have to serve me drinks all evening dressed in this." Gary chucked a piece of clothing at me.

I caught the piece of clothing. Holding it up, it looked like it was an orange, speedo style swimsuit. "I don't think I could even fit in this," I said perplexed. "I guess it would be pretty tight. I don't know Gary, this seems like some sort of weird sexual thing..."

Gary shook his head in the negative. "No, no, no. I promise, I will keep my dick in my pants. I just want to be waited on like I am vacationing at a resort. You will not be obligated to do anything sexual, no handjobs required. Hell, I will agree to pay you even if you lose, with payment following your services. But there is no backing out."

"Hmm," I pondered aloud. "Something seems odd about this but it sounds like a guaranteed win. Well, if you promise that I don't have to do anything sexual... I guess I agree."

"Wonderful," Gary said, his voice showing hints of surprise that I had agreed so easily. He handed me a pool cue and began to rack the balls.

I played very well and quickly sunk several balls in quick succession. It looked like I wasn't going to even have to put up with Gary's bullshit. I focused in on the eight ball and sunk it... this time without scratching. "Yes!" I celebrated.

Gary laughed. "I don't see why you're so happy. You just lost!"

"What?" I said aloud. I looked down on the table and sure enough I had forgotten to sink one of my balls. "Goddamnit..." I stammered."

"I will see you here at 8, make sure you are wearing that swimsuit when you arrive over here!" Gary said gleefully.

"Shit," I muttered. At least I would still get paid either way. The rest of the afternoon I dreaded the prospect of going back to Gary's apartment. When it got close to 8, I put on the flimsy excuse for a swimsuit that Gary had provided me. The suit tightly fit my junk. If I were to get a boner for some reason, it would be very noticeable. The backside was even worse. The material left my ass cheeks hanging out the back. I already had unusually large ass cheeks for a slender guy and this suit made my ass look like it belonged on a female porn star. Worst of all, the material was loose enough that there was a noticeable jiggle when I moved which I am sure would bring even more attention to my ass.

When I left my apartment, I was so nervous I felt a cold sweat form around my body. In an incredibly embarrassing moment, I ended up walking past Linda, a girl who I had a crush on in the building, as she was entering her apartment. She saw my jiggling ass in the orange swimsuit and gave me a very bizarre look. I couldn't think of anything to say so I just blushed and passed her by. "Ugh," I muttered as I made my way down to Gary's apartment. She must have thought I was some sort of weird pervert.

I knocked on Gary's door and heard him yelling to come in. I walked into the apartment and Gary was stretched out on the same couch where we had been sitting before. I immediately flashed back to me pumping his cock and rubbing his big balls. The thought made me shudder.

"The suit looks good on you," Gary commented. "But you have to let me see the backside."

"It's kind of revealing," I admitted. I slowly turned around and gave Gary a view of the back of the swimsuit with my curvy ass cheeks hanging out the sides. "Something bigger might be better..."

"No, that's perfect," Gary commented quickly. "I like the people who serve me to show off some skin. Now go and get me a beer."

I walked across the room to Gary's kitchen and noticed Gary staring intently at my jiggling ass cheeks as I walked. I could tell from the look on his face that he was sexually intrigued by my ass. The attention made me blush red.

"There is some white wine in there as well if you want to grab something to drink for yourself," Gary offered while he remained seated on the couch.

I figured I would be better able to cope with Gary's bullshit if I had a few drinks in me so I gladly poured myself a glass of white wine and grabbed Gary a beer from the fridge. I walked over to Gary and handed him the beer and then walked over and sat down on a dining room chair. I crossed my legs to cover up the swimsuit that I was embarrassed I was wearing and took a sip of wine.

There was a knock coming from the door and Gary yelled, "Come in!"

Another man walked in who I recognized immediately as Paul. Paul would also sometimes come over and gamble at pool or poker at Gary's apartment. Unlike me, Paul was very similar to Gary. There were both older, large men who were slightly overweight.

"Hello Gary, hey Danny," Paul greeted us as he took a seat down next to Gary. Paul turned his attention to me and spoke, "I heard from Gary that you're serving us drinks tonight. You can get me a beer, boy."

"You didn't say I would be getting Paul drinks too!" I objected. "Ugh... fine," I spoke, taking another sip from my wine glass. I set the wine glass on the table and uncrossed my legs and stood up. I walked towards the kitchen with my ass cheeks once again jiggling in front of Paul and Gary.

"Phew!" Paul whistled at me as I walked to the kitchen. "Hot damn, your ass can jiggle, boy."

I blushed red. My mind tried to grasp for some sort of sarcastic response but it just ended up drawing a blank so I remained silent. I continuing walking to the fridge and obtained another beer. I walked back out into the family room and handed Paul the beer.

"Thanks for the beer... and the show," Paul snickered. He reached over and grabbed the back of my right butt cheek and gave it a firm squeeze.

"Hey!" I objected as I pulled away from Paul. "Don't touch me!" I walked back over to the dinner table and sat down in my chair. I crossed my legs and grabbed my glass of wine and took another sip.

"Come on, relax, Danny," Gary said as he took a large swig from the beer he was holding. "We're just joking around here. You don't need to be so sensitive. Also, why are you sitting all the way there? There's plenty of room on the sofa. Come over her."

I picked up my glass of wine and walked over to the sofa where Paul and Gary were sitting. Contrary to what Gary had said, there was not plenty of room. I had to scoot in between the two large men and pull my legs tight crossed over each other. Paul's arm stretched out above my shoulder and I could feel the weight of both men pressing against my sides. Somewhat nervously, I took another sip from my wine glass.