The Four Encouragers of Freshman Year: Glenn

My favorite type of guy is a chunky twink. Unfortunately, or perhaps fortunately, I am constantly encountering such full figured boys as a college professor. I first encountered Damien while I was performing a guest lecture for a colleague’s class. Damien sat in the back wearing a stained white tee with a cardigan that surely couldn’t be buttoned even if he sucked in and tried. He had a pile of McDonald’s on his desk that elicited disapproving stares from his peers and piqued the curiosity of yours truly.

When he finished his food he belched quite loudly and I actually lost my train of thought. A silence briefly befell the room as he stretched his arms back so that his white shirt rode up against his happy trail as he leaned back with his hands behind his head. He looked at me rather smugly and I couldn’t discern whether he intended the air of eroticism around the gesture or if I was reading into things. Thankfully, I quickly found my footing again and continued on with the lecture.

At the end of the class I watched as Damien stood up and scratched his belly then gave it a good squeeze. He seemed to enjoy himself. Then he walked out of the room with an exaggerated waddle that was obviously unnecessary for a man of his size. Sure, he was chubby, but he wasn’t in waddling territory. Yet…

I asked my colleague about him and he sighed and apologized to me. Apparently Damien was known for making such displays of gluttony and all you could do was ignore the kid. There was no other recourse. If anyone commented on Damien’s behavior, especially a professor, they would be labeled fatphobic, canceled online, and possibly even fired. My colleague lamented this fact for apparently Damien’s behavior was quite disruptive at times. I nodded along.

I saw Damien a few more times around campus. He always had food in his hand, his clothes were always too tight, and he clearly wanted everyone to notice. So I hatched a plan. I found a reason to guest lecture Damien’s class once more and at the conclusion of the course I asked if he could stop by for office hours sometime. I was rather vague as to why, but sure enough he showed up at my door a few days later.

He wore that same stained white tee but with no cardigan and the bottom hem needlessly riding up. Surely, it would’ve covered him if he just yanked it down. I invited him to have a seat. On my desk I had a stack of cupcakes. They were from a faculty member, I lied, and offered him one. He gobbled it in two bites. I told him to have more, as many as he liked. He proceeded to consume one after another as I drolled on spouting meaningless academic drivel.

I don’t even know what I was saying, I was so captivated by the young man. His soft pink lips swallowing down cupcakes and his glittering, almost provoking, eyes had me mesmerized. His cherubic body and angelic face could have been torn from a Renaissance painting. Eventually, he finished the entire tray of cupcakes and then licked the icing from his fingers one by one. I stared in silence, aroused and speechless.

“Why don’t you take me to dinner and I’ll show you what I can really do,” Damien proclaimed.

I was taken aback, but I agreed and we exchanged numbers. A week later I sat across from him at an Italian restaurant, my wallet quivering in fear as he ordered half the menu with gusto. When the food arrived he wasted no time stuffing his face. Although I was well aware of the community of men who identified as feeders and gainers, I didn’t consider myself one of them. I liked chubby boys, that was all. However, watching Damien stuff himself with such a highly sexual fervor did cause a shiver in my loins.

I couldn’t help but wonder: How much bigger would he grow? Had he always been plump? What was his current height and weight? Was I interested in helping him grow even larger? I suppose the answer to the last question was “yes” considering the circumstances. Still, I was unsure of the ethics let alone my own interest. What I did want, I knew with certainty, was to fuck that plush bubble butt of his.

Unfortunately, when he came back to my place that evening, he rejected the idea of anal penetration. Instead he wanted to guzzle the milk in my fridge. I let him, of course, but I needed sexual gratification. He seemed hesitant of pleasuring me so I went ahead and sucked him off. After he came in my mouth, he promptly found an excuse to leave. I was frustrated, to say the least.

A week later, he was texting me asking me to take him out to dinner again. The subtext was clear: he did not want to pay. That was fine, but I told him I needed some level of gratification from this exchange as well. He told me that after this next dinner he would consider it. Well, he did and the answer was no. I was upset and dismissed him from my apartment coldly. Once again, a week later he was texting me. This time, he promised that if I fed him six thousand calories of food from the Cheesecake Factory in one sitting he would allow me to fuck him. This kid was unbelievable. I accepted.

He arrived at my apartment wearing clothes fit for someone half his size. The food was delivered shortly after and we got down to business. I spread out the sprawling order of food across the dining table and set a comfortable armchair nearby. He sat down and stared at me expectantly. I had never done this before, but it seemed easy enough. I forked up a wad of pasta and held it to his mouth. He chomped down more expeditiously than I anticipated. Mere moments later I had more pasta in his mouth and as we continued I marveled at the veracity of his appetite.

As we progressed through the meal he began to moan and shift his belly in discomfort. Finally, I realized he was signaling for me to unbutton his pants. I did so and his belly spilled forward from his shirt. I rubbed the freed chub a bit, admiring the softness of his skin and the small stretch marks around his navel. I could tell he liked the belly rubs and so I kept this up, eventually removing his shirt altogether before rubbing each other’s cocks through our pants in between bites.

Once the food was gone I had him properly worked up and removed his jeans. He had a decently sized rod, with foreskin, and quite proportional, and although I desired to suck him off I refrained from doing so in case the night ended there once again. Instead, I undid my own pants to reveal my own slightly larger erection. I had an impressive cock yet Damien didn’t react like most boys do when it’s unveiled. Instead, his eyes lingered on my modest paunch. He was a true fat fetishist, this much was obvious.

I began touching his rear and I sensed hesitation. I decided to whisper sweet fat nothings in his ear about how plump he was becoming. This seemed to do the trick. I continued down this path, constructing the most verbose descriptions of his corpulent form that I could conjure in the moment. I only stopped talking once I had him on all four and was parting his cheeks.

He really had a magnificent behind. It was engorged with fat and soft as a pillow. White stretch marks striated the expansive cheeks and a soft trail of hair decorated the crack. I dove in face first and worked on his hole for quite some time until I could tell he was fully relaxed. I then inserted a couple fingers which he responded to as long as I kept describing how fat he was. At some point I called him a “piggy” and this seemed to be the magic word. His hole opened right up.

I got onto my feet and began to insert my manhood. He moaned and whimpered. I encouraged him while rubbing his belly from the side and massaging his love handles. I took it slow, pumping in and out whilst admiring the jiggle of his husky body. As I quickened I could hear all that Cheesecake Factory sloshing around in that swollen gut of his. From behind he was a true sight to behold. It was rare to see a twink so freshly doughy at his young age. Typically the overweight young guys were either ex jocks, skinny fat, or had been obese their whole life. Damien was something special. It didn’t take long for me to come.

Throughout the months of March, April, and May we repeated this routine several times. I started to feel an affinity for the boy, especially as I noticed signs of his growth that I was contributing to. His tits softened considerably over the course of those two months, developing a delightful crease where they met his belly. I also oversaw the emergence of a new fat roll between his love handles and upper back, along with a burgeoning baby fat pad. It was quite erotic and I began to develop an interest in encouraging.

Unfortunately, Damien began to drift away from me. I wasn’t entirely sure why, but I suspected he found someone closer to his own age to grow fat with. It was heartbreaking at first and I had to avoid behaving like a creepy old man. At the very least, I was grateful for this new side of my sexuality he had unlocked as I began meeting guys on gaining websites. Still, Damien was never far from my mind.

Over the course of that school year I saw Damien from a distance a few times and each time he was fatter than before. It was incredible his steadfast investment in this kink. Finally, over the summer I saw him at a Mexican restaurant with another guy; someone his own age as I suspected. His counterpart was quite fat as well yet not as beautiful as Damien in the face. I could hardly look away. Oh, how I would have loved to see that sex tape.