Billy from Behind

Billy and I met after I sold him a desk on Craigslist one summer. He was new in town, merely 20, having just moved to the big city for school. He hailed from Colorado with a charming authenticity that immediately caught my attention. Not to mention his dirty blonde curls, tight ass, and glittering smile that would have sent any man swooning. However, my interest waned throughout the duration of our first date at a small cafe in town.

I was nearly 30 years old and the age gap was larger than I felt comfortable with, especially as I observed his general nervousness, naive enthusiasm, and interest in partying. The nail in the coffin was when he mentioned losing weight during the move and always “forgetting to eat.” This wasn’t compatible with my own little kink.

Billy texted me occasionally, but eventually I ghosted. A bony boy, even one as beautiful as he, was not worth my time. Eventually, I completely forgot about him.

That is, until one day in March. It was the first warm day of spring and myself and half the faggots in the city were sprawled in the sun at the local nude beach. I was with a couple friends, feeling my oats after a winter of relentlessly working out and getting several new tattoos. I felt hot and ready to show off.

In the distance I saw a guy just my type, someone who could be summed up as a “well fed twink.” He was disappointingly not nude, but the fullness of his ass was still visibly bouncing beneath a teal Speedo as he pranced into the water. From several yards away I could spot thickened thighs that looked freshly plumped with fat and surmised a small belly was attached to the front. Blonde curls caught the salty ocean spray.

I sipped my White Claw and kept an eye on the young man. When he finally turned around and headed back to the beach I was startled to recognize his face. The sharp blue eyes, soft pink lips, and high rosy cheek bones could belong to none other than Billy. My heart accelerated. I watched obsessively as his small stomach, maybe two inches of soft dough above his waistline, came into clearer view. He sat down with friends not too far away.

It took several minutes and strong glances before we made eye contact from across the beach and I waved. He looked drunk and excitable. I stood up and sauntered over.

“Billy, so wild to see you here,” I said with a grin.

“Likewise!” He burped and chuckled, then took another swig of some brightly colored liquid in a jar. “My boyfriend brought us down here. It’s so cool! I’ve never been!”

“Boyfriend?”

“Yeah,” Billy said, clueless to my wounded ego, and pointed at a man about my age walking down to the water.

To add insult to injury this guy was in far better shape than myself, with shoulders wider than I could ever dream of and chiseled muscles that glimmered in the sunlight. I immediately felt foolish for giving up on Billy so easily. He was a catch by any normative standard, plus he had the capacity to put on weight as well.

I turned my attention back to Billy. He looked ravishing. His stomach was bloated from drinking and pushing at his waistband. Sitting down, his pink sun kissed thighs spread out beneath him. His ass was incredibly bulbous and round, puffing out in all directions. Surrounded by smaller twinks, Billy’s weight was especially obvious. He offered me some of the dayglow liquid he was consuming, but I refused and retreated to my blanket.

For several weeks Billy remained on my mind. I jerked off to fantasies of him growing fatter under my care, of his weight jiggling beneath the impact of my cock as his perfect face cried out in pleasure. I wanted to text him, but instead I worked out, striving for physical perfection so that maybe one day I could steal him away from his adonis boyfriend.

By the time summer came I was more fit than ever, prancing around in the skimpiest clothes I could find. I had an appointment one day in the university district and of course arrived in the hopes of running into Billy. After an embarrassing amount of prowling I gave up and stopped in for a patio drink at a nearby bar. To my delight, I spotted Billy in the corner. Unfortunately, he was with his hot boyfriend.

I sat down as inconspicuously as possible, put on my shades, and spied on them to the fullest capacity. The first thing I noticed: Billy had gained weight. He wore a T-shirt and khaki shorts, both of which were pretty snug. His butt looked unbelievably juicy and hung off the back of the chair ever so slightly. The waistband cut into him dramatically so that his love handles appeared curvier than they actually were. Same for his stomach that was muffin topping beneath a gray shirt from more youthful days.

It had been about one year since I first met Billy and I was confident he’d surpassed the freshman fifteen. By the looks of it he’d been partying a bit more than his body could handle. Still, his face remained slim and those boyish good looks were as radiant as ever. He was eating nachos with a fruity drink and every time his licorice lips wrapped around the straw or a heaping bite of food my cock got a little harder.

His boyfriend looked the same: buff, hot, overconfident. Only something was off. It appeared they were in the midst of an argument. The boyfriend was motionless but speaking sternly whilst Billy rolled his eyes between bites, sometimes shrugging or shaking his head. Finally, I heard him raise his voice indignantly, “what do you want me to do?!” With that the boyfriend shook his head, threw down some cash and walked out.

Barely thinking, I swooped in for the kill. Sitting down at the table with no introduction, I startled Billy whose crystal features turned from irritated to shocked to bemused.

“Oh, it’s you,” he said with a devilish grin.

“That it is,” I replied.

We chatted for a bit, me trying to seduce him, him playing a long but not fully giving in. Finally, I invited him to another bar but he turned me down. He blamed it on his boyfriend. Accepting defeat, I went home.

A few days later I sent Billy an innocent text. It sparked a conversation with an underlying sexual current that ultimately didn’t go anywhere. As the weeks passed I couldn’t get him off my mind and had to fight every impulse to demand he go out with me. I fucked a variety of thick college twinks but none were as beautiful as Billy. When fall rolled around my prayers were answered. I received a text from the object of my desire that simply read, “wyd.”

Before I knew it we were grabbing drinks at a bar. I arrived first to get the tab going and waited. Billy walked through the front door looking positively thick. He wore a vintage sweater that draped softly over the curve of a healthy paunch and blue jeans that were supposed to be a loose fit but clung tightly to the girth of his legs. From the way he walked I could tell his pants were uncomfortably stuffed full of freshly grown college aged surplus dough.

He grinned and struggled to bend in half to mount the bar stool. We exchanged pleasantries before I fetched him a drink. As I returned to the table I got a full vision of Billy from behind. His sweater road up as his pants were pulled low, revealing a succulent ass crack rosy with exertion from the walk over. His ass was fuller than ever, practically begging for my cock. Higher up I could see that he’d finally developed real love handles, the kind that didn’t go away when you stood up or stretched. Bona fide chub clung to his midsection.

Delivering the drink, Billy asked, “Do they have food here? I’m starving, I don’t know why.”

I replied in the affirmative a bit too eagerly. Billy put chili fries on the tab and guzzled drink after drink. The boy was a bottomless pit and I had no problem feeding him until he was ready to burst. An hour later we were both pretty tipsy and en route back to my apartment.

As soon as the door was shut I had him pinned against the wall, his soft belly pressed against my hard abdomen. He tasted like chili fries as our tongues wrestled and my hands slipped beneath his sweater to grip his abundant flesh. He let out a boyish grunt under the force of my passion and I could feel his cock straining against his denim.

Pinning him against the wall, I patted his hearty thighs, gesturing him to hop into my arms. He seemed surprised and nervous as to whether I could support his weight. What he didn’t know is I had been training for this for months. I hoisted his heavy body into my arms, both arms supporting his girthy legs as my hands finally made contact with his ass.

He was heavier than I expected as I carried him to my room and plopped him onto my bed. His body jiggled from the impact and lust overcame me. I pounced atop him, pawing off our clothes, and devouring every part of him. I was so flush with desire that I hardly remember anything until I had him flipped over with his full moon facing me. Billy from behind was as much a sight to behold as from the front.

His ass was perfectly pert and round, pounds of fatty flesh somehow defying gravity before me. I Ilicked up every curve and crevice until his hole was practically begging me to enter. At long last I was finally inside of Billy. My hands gripped his love handles as I pumped my cock into him. I took great joy in every yelp that escaped his perfect lips, sometimes smacking his meaty rump as encouragement.

Within minutes he yelled that he was on the verge of orgasm and begged to sit on my cock. I flipped onto my back as he straddled me with his plush inner thighs and sat on my dick. He bounced to and fro, losing himself in a prostate orgasm. His stomach sloshed heavily before my eyes and I gripped it with one hand, my other on his ass fat, ramming him down until he began shooting come across my face, chest, and bedroom wall. Seeing his explosion spurred my own orgasm as I shot a massive load inside of him.

Billy stayed over that night and left in the morning. That was the last time I’d see him for almost nine months. He was to study abroad in Italy for two semesters and I had to extinguish him from my mind lest I go crazy with desire.

I was fairly successful. In fact, I fell into a fairly serious relationship with a guy about my age. He was slender, but a former fatty, and was happy to let go of his diet with my subtle encouragement. I was pretty content, though Billy was never far from my mind. I hoped he was overseas indulging his appetite, having fun, and getting that bubble butt pleasured with regularity.

By the time summer rolled around my relationship was too serious for me to sneak around and hit up Billy. Still, I caught a glimpse of him on the sidewalk one day while I rode the bus. To my delight, he’d probably stacked on about thirty more pounds in the last year. Most of it clung to his belly which jutted out dramatically from beneath that same gray T-shirt. The weight lent him an older appearance, yet his face was still as chiseled and boyish as ever. My heart skipped a beat as I froze that image in my mind.

Two years went by without a peep from Billy. And then, one June I received a message: “hey, this is billy. I’m about to graduate and move back to colorado soon and would love to get a coffee or something. I saw on ig you have a bf so I get it if you can’t.”

I couldn’t resist the temptation.

I devilishly scheduled our coffee date at a time I knew Keaton, my boyfriend, wouldn’t be home. I was dressed as sharp as I knew how and arrived at the cafe with butterflies in my stomach. Billy was already there looking, not surprisingly, overweight.

He stood up and gave me a big hug, his prodigious belly keeping several inches between us. Sitting down I was in awe. In the last four years, I witnessed this guy transform from an emaciated twink into the chubby cub sitting before me. I wagered he was probably around 250 pounds at this point.

The weight had finally crept up to his face, softening his jawline. Perhaps he had been working out now too, as he looked and felt a bit harder and more mature. The innocence in his face had vanished and was replaced with a dashing worldliness. His movements seemed more confident and his desire towards myself more assured.

He had purchased food which was shortly brought to the table: an egg white wrap, a chocolate croissant, and a large caramel frappuccino. My black coffee looked conservative in comparison. I spied strength in his chest and arms, despite their softness, as he dug into his food with delight. We caught up on each other’s lives over the past two years, while a latent horniness was fully present within both our hungry gazes.

Billy’s stomach had expanded by the time he finished his meal. It was clad in a green polo shirt that fit well. He was certainly too large to even attempt hiding the pot belly that rested in his lap and had opted for the sensible choice: displaying his girth with pride. Indeed, the belly in front of Billy was that of a man’s. Grown over the course of several years and hundreds of beers, fed lovingly, and supported by strong shoulders and a love for food.

Once he even leaned back and patted his stomach with the contentment of a guy that’s not afraid of indulgence. When he got up to use the restroom, I got an eyeful of his lower half. Surprisingly, it had not grown in accordance with Billy’s upper body. His ass was certainly still a handful and thick as ever, but it balanced out the heft of his upper body. Nevertheless, his jeans were completely stuffed. It probably was difficult for him to find any pants that fit well. Or, perhaps, he chose a snugger pair to catch my attention…

When Billy sat back down he grinned and leaned forward atop the table. The top half of his gut, bloated with food and sugar, oozed forward as the table cut into it. With his elbows close together and resting on the table, Billy’s arms and chest looked fluffy and big. The grin simmering across his face accentuated the slight chub on his cheeks.

“I know we’re both partnered and all, but what do you say we head back to my place?” he purred.

“I can’t say no to that smile.”

We stood up and with a wave of passion overcoming me, I stepped forward and grabbed him by the waist, pulling him in for a kiss so that his soft stomach pressed into mine. In the middle of the cafe, I slipped my hand under the fabric of his shirt so that my fingers could squeeze his warm overfed belly. Giving it a slight jiggle, I let loose and left his belly slightly exposed. My lips still upon his, I gave that gut a loud slap in the middle of the restaurant. Multiple people looked over as we giggled and escaped out the door.

What transpired was some of the best sex of my life.