My Best Friend's Brother

I would be lying if I said I had never fantasized about fucking Milo Carr before. The kid was an ideal piece of ass. I didn’t usually go for younger guys but Milo was an exception. I was best friends with his older brother, Dimitri, and first met Milo about five years ago when he was twenty. Dimitri and I became friends through an old job, eventually becoming gym buds who would grab a beer occasionally. Dimitri was straight and didn’t seem to care that I was bi. In fact, I think he was kind of envious about how easy it was for two men to get casual sex.

Dimitri introduced me to Milo a couple years ago at the gym. The kid claimed he wanted to bulk up now that he was in his twenties. At the time, Milo was pretty twinky and obviously gay. He had nice features and a charming smile, but like I said I’ve never been into younger guys, especially twinks. I actually prefer my men to be older and thicker, especially in the belly and ass. Still, I could admire the youthful beauty Milo possessed. 

Ultimately, Milo only stuck to a gym routine for about ten months. We taught him about protein intake and macros and he gained a little muscle. But soon as he got into grad school he stopped going altogether. I actually forgot about the guy completely until I ran into him again at Dimitri’s. A couple months prior my apartment was getting fumigated for mold and Dimitri offered me his spare room. Milo was also staying with him at the time but would be sleeping on the couch. I didn’t ask any questions and was just happy not to go to a hotel. 

When I arrived at Dimitri’s house I was pretty shocked to see Milo. I think it had been about two years since I had last seen him, but he had gained a considerable amount of weight. Like we’re talking forty to fifty pounds. He wasn’t fat per se, more like thick. Seriously thick. It looked like he was still hitting the gym at least intermittently but also was eating heavy. Mind you, this was a serious shift from the twink he used to be, and his clothes showed it. 

Everything he wore dug into him and needed to be replaced. This accentuated his heft and made him look plumper than he really was. At the time I was in the midst of a winter bulk and probably had a good fifty pounds on him, yet he still looked puffier than me by virtue of his clothes. Come to find out he was occasionally hitting the university gym, but mostly partying it up. He confessed he never had really partied in undergrad and so he was letting loose more than he should have been. The consequences of which were reflected in his grades as well as his waistline. 

I only stayed a couple nights with Dimitri but boy did I develop an infatuation with the young Milo. I made sure the three of us guys went hard on take-out both those nights and encouraged Milo to keep pace with me since it was winter and we were bulking. It was hard to keep my eyes off the love handles peaking out over his sweats or the way his ass bulged outward in profile. Both nights I shot fat loads into a pair of dirty underwear as I fantasized about bouncing those fat cheeks against my cock. 

I ended up following Milo on social media after my stay but unfortunately he didn’t post much. Occasionally I would ask Dimitri how Milo was doing but I didn’t want to seem too creepy. Finally, after one such query, I got the answer I had been dying to hear. 

“The guy is getting kind of fat. I’ve been wondering if I should say something.” 

“Best not to,” I warned. “He’ll probably lose the weight when he’s done with school.” 

That was a lie, or at least I hoped it was. In fact, I kind of hoped Milo’s weight would snowball from here on out. 

I think it was about six weeks after that comment that I finally got to see Milo in the flesh again. It was summer and he had come to stay with Dimitri for a couple months. Needless to say, I was entertaining some ridiculous fantasies and couldn’t help but get my hopes up. Part of me felt guilty for being so horny for my close friend’s little brother, but what was I supposed to do? That’s just how men are programmed, right? 

Finally, I got to see Milo briefly in passing. The kid didn’t have a car so Dimitri was dropping him at a friend’s after picking me up on the way to the gym. I hopped into the passenger seat eagerly and turned around to say hello to the young grad student. I tried to suppress my enthusiasm which was especially difficult once I laid eyes on the lad. 

Milo was indeed getting fat. He probably had gained another thirty pounds or so, which pushed him out of slim thick or twunk territory and firmly into “chubby.” And while he maintained a sort of thick-all-over physique, a prominent belly was beginning to emerge. It sat comfortably in his lap with enough curvature that Milo was able to rest his hand on it while he held his phone and scrolled. I gathered all of this from a brief but focused four second scan from the front seat. 

When he got out of the car, it was doubly confirmed. Milo was wearing Dickie’s that gloriously hugged his plump bubble butt and hoisted up his love handles as he walked away with a slight jiggle to his step. I devoured every second of watching him walk away. My dick was already half chubbed so I resisted commenting on Milo’s weight to his brother out of fear I would fully pitch a tent in my gym shorts. 

For the next few weeks I only saw Milo a couple times in passing. Each time he was wearing a tank top that hugged his curves and displayed his surprisingly hairy chest. I had never realized he was such an otter, but it did add to his allure. He was also slurping down a massive drink on both occasions. First, a big creamy looking boba and second a Dunkin frapp drowning in whipped cream and syrup. 

Finally, my big break came when Dimitri asked if I could do him a favor and pick Milo up after a job interview. I was eager to accept but tried to play it cool. Immediately, my mind swirled with fantasies of buying the kid celebratory fast food and then fucking him silly. By the time I actually had to pick him I had created so much expectation in my head that I was nervous. 

I watched Milo emerge from the office park. He wore a button up shirt that fit appropriately except for the bottom button which was straining from his weight. His slacks needed to be sized up as they clung noticeably to his thighs and ass. When he got in my car the shirt strained further and I could glimpse the outline of his cock through those cheap H&M pants. 

I made small talk. The interview had gone well. He didn’t really want the job anyway. One of the upsides of the position was that they had a robust healthcare package including discounted gym memberships. My heart skipped a beat and I wasted no time in going down that road. I discovered he basically had stopped going to the gym and had picked up bad eating habits from his roommates at school. He confessed he was smoking too much weed and for the first time in his life realized how much he loved food. I told him he looked great and carried the weight well. 

“Easy for you to say,” Milo said and looked me up and down. For the first time I suspected chemistry between us. “I mean look at your arms.” Milo squeezed my exposed bicep. 

My heart skipped a beat and frankly I don’t even know what I said, but what followed next really surprised me. 

“Dimitri says your bi.” 

At that moment I pulled into Dimitri’s driveway and began to panic. This was my opportunity but I didn’t know how to exploit it. 

“Yeah,” I laughed. “Are you?” 

“No,” Milo said, “I like men, only men,” and got out of the car. 

I could’ve burst. Was he coming on to me? He definitely was. What should I have done? What should I do next? I am a decade older than him after all. Would Dimitri be upset if we fucked? Would I have to tell Dimitri if it happened? My cock was leaking with excitement. 

The next five days I sort of spiraled. I didn’t know what to do about my desire for Milo and so I went on a food and alcohol bender. I think part of me wanted to get fat too, but I was afraid to confront that fact so I drowned it out with alcohol. And if I was too hungover to hit the gym then I wouldn’t have to confront Dimitri and my inappropriate infatuation with his younger brother. I snapped back to reality when Dimitri texted me one day once again asking if I could pick up Milo from a job interview. Obviously the answer was “yes.” 

I pulled up to the dour office building and took a deep breath. I had a plan of action but my nerves were still on fire. Milo emerged from the building noticeably in good spirits. He wore a navy blue polo shirt tucked into those same snug slacks. A belt cinched his waist with a silver buckle that subtly pressed against the lower part of his belly. The polo shirt didn’t strain as much as the button up he wore last time, but it did hug his love handles in a manner that was hard to ignore. 

Milo plopped into the car with a jiggle and a smile. The interview clearly went well and he told me as much. I congratulated him and squeezed his shoulder. It was a long drive back to Dimitri’s so I casually suggested we stop and eat at my favorite Mexican restaurant. Of course the little pud eagerly agreed. He even said he was “starving.” 

I intentionally parked on a side street by the restaurant in a particularly desolate part of town. It was a short walk to the front door but thankfully no suspicions were aroused. Inside the taqueria we each ordered wet burritos, chips and guac, and two horchatas. Milo scarfed the food down like there was a famine. It kind of shocked me honestly. Most gay guys I knew were rather fastidious and concerned with public appearance especially around food. Not Milo, he dug in with gusto. It was obvious why the kid was thickening up so quickly and I had zero complaints.

“Should we try the ice cream?” Milo suggested. 

I was surprised that ice cream was even on the menu, but obviously I agreed. I was actually pretty stuffed already but there was no way in hell I was gonna slow this greedy little pig down. We got our cups of ice cream and sat back down at the table, an odd silence between us. 

“I wanna get back in the gym with you,” Milo broke the silence. “You’ve got the ideal physique honestly. Muscley but still kinda chunky, beefcake vibes.” 

I couldn’t help but laugh. “Yeah, let’s get you in there,” I replied coolly. “I’d love to help thicken you up.” 

Back in the car we buckled up and looked at each other with equally mischievous grins. I noticed that Milo had some ice cream on his chin and I knew that this was my moment. I steadied myself and reached over to wipe it off with my thumb. With the smudge gone, I remained leaned over, my belly pressing into the console between us. Milo grinned and leaned forward into a kiss. 

He tasted salty and sweet from the food. I was instantly hard as I reached over and gave his bloated belly a rub. He was warm and soft to the touch. Our tongues intertwined and my hand slid under his shirt to grasp that gelatinous roll of pudge above his belt. He reached over and grabbed my pec, giving it a squeeze and thumbing my nipple through my T-shirt. My cock tensed from the sensation. I wanted inside of him so bad. 

I pulled back and looked Milo Carr in the eyes. He had a dreamy look about him. I nodded to the back seat and he smiled. We got out of the car and moved to the back where we removed our shirts. I was surprised to see that our bellies were close to the same size, meaning I had porked up more than I realized recently. However, Milo’s fat was softer, more plush. It spilled forward luxuriously into his lap whereas mine stood pert atop my physique. I undid his belt buckle and pants so the fat could rest comfortably for my taking. 

I squeezed a handful and gave it a vigorous shake. Milo whimpered from the gesture and pawed at the hard on straining against my jeans. We each tried to pull down our pants but it was a struggle for two big boys in the back of a car. So much so that there was a moment of mutual recognition where we laughed at ourselves before finally freeing our erections from the confines of any pants or underwear. 

His cock was bigger than I anticipated for a guy his height, and it pressed against the lower reef of furry belly fat. I wanted to suck him, but he promptly straddled my lap. This was even better. His fuzzy warm ass cheeks plopped atop my thighs, my cock tapping against the entrance the girthy cheeks protected. We made out as I massaged the gooey bubble butt in my palms. Our stomachs pressed together tightly and we began to sweat. Our surplus weight created a further sense of intimacy. We took up so much space in the small back seat, our bodies’ thick bulges and folds melting into one another. 

As the windows fogged up I slipped a finger in his hole, and then two. He grinded himself on top of me and it was clear he was hungry for cock. The little piglet knew how to bottom. We each contributed as much saliva as possible to his opening so that I could slide inside. He moaned as I entered. We were now sweating profusely. His chubby little tits that sagged with fat were pressed against my face. Our body hair was matted with sweat and intertwined as he rode my cock deliriously.

Milo was beginning to lose himself in the moment and I was loving every minute of it. We kept it slow and sensuous for a good several minutes, relishing the friction between the density of our overfed bodies. Milo stroked himself as he rode me but as our pace quickened he couldn’t sustain the motion. He had to steady himself on the seat as I clapped his cheeks, so I reached between our precious mounds of belly fat and gripped his cock. He writhed in pleasure and fully leaned his entire weight against me. I struggled for air as he began convulsing in orgasm. 

I hammered his hole persistently until I was on the verge. Feeling the orgasm swell in my balls, I slammed his fat as fully down onto my erection and buried my face in his chest fat. A guttural moan escaped my body that actually startled me a bit. As I filled his ass with my come he whimpered approvingly. Once I was finished Milo simply collapsed on top of me. 

I could barely breathe and had to move him into the seat next to me. We looked at each other, both of us drenched in sweat, our hair wild, our eyes blissed out, and chuckled. As much as I had premeditated fucking Milo, I hadn’t considered how messy our sex would be. The seat was wet with sweat and come was oozing out of Milo. Our underwear was simply not enough to scrub it all clean, so I found an old park blanket in my trunk that would suffice. 

We were too fat and exhausted to put our clothes back on in the confines of the backseat, so I wiped the window clean and ensured the coast was clear. We piled out of the car and stood naked on the side of the road like two animals shamelessly trying to compose ourselves once again. It felt absurd and we both grinned wildly. When we got back in the car it smelled undeniably like butt sex. All we could do was laugh. 

“I have an idea,” I said. “Why don’t we go to the gym? We can shower off there and maybe get a head start on your bulk. And then we have an excuse for Dimitri about why you’re late.”

Milo leaned across the console, placed a hand on my belly and kissed my cheek. 

“Sounds perfect.”