A Cheek Job a Day Turns the Doc Gay

I volunteered my services as a doctor at a medical ward for the poor. I'd come from a family of great wealth and therefore never had to set up my own practice or accept payment in exchange for medical care. I'd studied under the greatest doctors in America and London before taking my current position.

I paid the people I worked with little attention except for one. He was a floor sweep named Chapa. A big, fat native that must have weighed over three hundred pounds. It was his ass that was especially big and fat. And either they didn't make or he couldn't afford clothes that were big enough to hide that humongous thing. The material of his pants always rode up deep into the huge crack of his ass.

I was a respected doctor, with plenty of eligible young ladies in town just waiting for me to ask them to social functions, I didn't understand why I couldn't stop looking at Chapa's big, fat ass. Or why it fascinated me so.

My secret, puzzling attraction to Chapa's junk led me to treat him much better than my colleagues did. One night after all the patients were bedded down I allowed him into my office to have a drink. I kept my liquor under lock and key in my desk and he told me that it was probably the best drink he'd ever tried.

We got to drinking and talking more. I asked Chapa rather innocently what he did before he got his job in the ward. Chapa took another drink and confessed that before now he couldn't find reputable work. He said he stole to support himself until he got caught doing it. After that he knew he needed a new line of work. Chapa told me then of how he began to work out of a bar giving dime cheek jobs in a backroom and splitting the earnings with the barkeep. He smiled a little sheepishly and admitted the barkeep had gotten his fair share of cheek jobs along the way as well.

I had never heard the term 'cheek job' before. I pleaded my ignorance and asked him what it meant. Chapa seemed a little uncomfortable at first explaining what the foreign-to-me term meant. He replied to me in less polished speech that a 'cheek job' referred to a sex act where ass cheeks are wrapped around a penis, rubbed and bounced together until ejaculation of the penis.

I was floored by Chapa's admission that giving cheek jobs was how he used to earn money. The skin under my collar got hot imagining it. I worried suddenly that I was seeming a little too interested in his past line of work. I responded in a way that made it appear I doubted anyone would pay for such a thing, especially from him.

What I said must have come off meaner than I intended. Chapa became very defensive. He said he'd been paid thousands of times for the service. Often dozens of times in one day. He said in the town where he'd worked that pretty much every man had gone through his cheeks at some point.

My face had a healthy redness to it by then. Chapa turned that into a full blush by suggesting that if I still didn't believe him he would give me a cheek job right then and there. He promised I wouldn't doubt him that he'd done this for a living after that. After having so much to drink I agreed without thinking. He told me to disrobe as much as I felt comfortable and he'd go down to his underwear for it.

Chapa stripped his pants off in front of me. The brown underwear he wore underneath wrapped tightly around his huge, wobbling ass. Between the two colossal cheeks was a damp patch of sweat where the material of the underwear rode up into his crack. I pulled my pants and underwear down in one swing. My cock twitched.

Chapa walked back and hovered his fat ass over my lap. He lowered it slowly until his hot cheeks engulfed my cock like a hot dog in a bun. The soft, damp heat that greeted my dick made it twitch again. Chapa squeezed his soft cheeks down with incredible strength around my shaft. I gulped. It sure felt like he'd done this before.

Chapa's sweaty crack was so large and deep that it easily engulfed me. The enormity of his ass was intimidating. He squeezed the big, flabby cheeks tightly around my length and then bent his knees up and down, masturbating my cock with them.

I groaned. I didn't know what I was expecting, but I didn't expect for it to feel this good. The way his massive cheeks bulged out of his underwear was obscene. I should have been disgusted by this dirty act playing out before me, instead I was enthralled. The humongous cheeks of Chapa's ass started to bounce up, down and around on my cock. He expertly shook and shimmied in such a way to create the most pleasure and friction between our bodies.

If I hadn't been convinced that Chapa had done this before, I certainly was now. He was a pro. An expert at the craft of giving what he called 'cheek jobs.' His big, fat, vibrating ass was very close to bringing another satisfied customer to climax. I don't think my cock had ever been harder as it disappeared in and out from between his stretched underwear.

I found Chapa's enormous ass to be hideous in one sense, darkly erotic and alluring in another. He manipulated the cheeks of his ass around my dick with all the dexterity of fingers. Chapa stroked my cock between his cheeks right to the brink of ejaculation.

I groaned again, my eyes shut and my toes curled. Chapa must have known my orgasm was imminent because he stopped his lurid gyrations and clamped those enormous cheeks down hard around my dick. The heat and strength of his grip sent me over the edge. My cock throbbed and exploded in his crack. He massaged his cheeks back up and down my manhood as I emptied my balls on him.

I felt completely drained. Still between his cheeks, my cock began to shrink back to size. Chapa released his crack hold on my penis and stood up. His underwear and lower back were covered in my cum. Feeling very embarrassed now, I jumped out of my seat and hurriedly pulled my pants up. Chapa took a small hand cloth off my desk and dabbed at the back of his underwear before putting his pants back on. His ass was so large and fat that it took a few attempts to pull them up all the way.

I couldn't shake my shame and embarrassment at what we'd done. I realized I'd probably put my whole career and reputation in danger by engaging in such lewd behavior with this miscreant. I nervously reached into my overcoat and pulled out the money that I knew were there. I quickly offloaded the cash into Chapa's hands.

"Take this and please go. I have a lot of work to do." I didn't wish to share the room with him for one more second after what had transpired between us.

It was a decent sum of money I'd given him. Enough for good food and drink. He looked at cash and mercifully left without another word having to be said.

I was preparing for my rounds the next morning when Chapa entered my office unannounced. No one was allowed to do that before now. The big fellow strolled confidently over to my desk and slapped the money I'd given him yesterday down onto it. I would have bet that he'd already spent it all on booze.

"I'm busy right now. What's this?" I asked.

"I don't want it. I don't whore my butt for money no more."

"Okay, good to know. Thank you," I said, picking the money up and quickly shoving it into the desk of my drawer.

"There is something I want."

"What is it?" I inquired. "I told you I'm busy."

"In exchange for my silence."

"Your... silence?"

"What'd happen to your reputation if everyone knew bout the cheek job I gave you?"

I gulped. "It would do the same thing to your reputation."

"I sweep floors. I'm nothing. A man like you..." he turned his hip in and grabbed the fleshy meat of his ass, "isn't supposed to stick his cock between cheeks like these."

"What do you want?"

"I want you to train me. I don't want to sweep no more. Teach me a skill, how to be your assistant. Whatever I got to do where I don't have to sweep floors."

"There are schools for that. I can't just teach you. It doesn't work like that."

"You didn't think cumming up my butt cheeks was gonna work til you done it."

I sat down in the chair behind me and rubbed my head. "Why are you doing this to me?" I asked him. "Fine, I'll do what I can. Just keep that between us."

Chapa approached where I was sitting. He began to rub my forehead with one of his big hands and said, "This don't have to be miserable. Since you're helping me I'll give you more cheek jobs." I pulled away from his hand. It was a ridiculous offer. I'd never let my penis anywhere near his fat, ugly ass again.

I tried to explain some medical basics and professional conduct to Chapa throughout the day. It was slow going and tedious. Trying to boil things down to the kind of small nuggets of information that this big neanderthal would have any chance of understanding had me very frustrated.

The worst part was having to see his enormous ass trailing me everywhere, bumping into things, swaying and bulging. I cursed myself again and again for being drawn to that hideous thing. I imagined it probably smelled terrible. It was grotesque, but it was beautiful. It was just about driving me crazy.

Attempting to get any facts through his thick skull was exasperating. I came away with the opinion by the end of the day that Chapa really was only good for one thing. Shaking that big ass on a dick. I yearned for that release again. When we got back to my office I swallowed my pride and asked him for another cheek job.

He stripped his ass naked and I left my underwear on this time. I could see and feel his bare skin against me. Chapa's big, dark cheeks swallowed my manhood whole and clenched it like in a strong muscle. It was glorious. The hot, firm grip of his fat butt melted all my frustrations away.

"That's good," I could hear myself saying. "Just like that, slut. Fuck this cock with that big, ugly ass." I never talked like this before. It would have been unthinkable to use such language. Something about Chapa and his gigantic, jiggling ass just seemed to bring it out of me.

I used my hands on it this time. I squeezed and kneaded the meaty dough of his magnificent ass. I spread the cheeks wide and then squashed them tight around my shaft. Chapa's asshole, small and alluring, caught my attention. I pressed the side of my hard dick against it and groaned. Chapa immediately got the picture and squeezed down hard, pinching my cock and keeping it trapped there, lodged between his enormous cheeks, sitting snugly against his hole.

"Has anybody ever put it inside?" I asked. The little brown opening should have disgusted me, but in reality I don't think anything could have turned me on more than Chapa's hot, winking pucker.

"Sometimes," he replied, clearly concentrating hard to produce the iron grip he used to hold and pleasure my cock within his crack. "If the money's too good or I'm in trouble and it's the only thing that'll get me out of it."

It was sobering for a second to consider someone like Chapa who hadn't grown up with my advantages and had only his massive ass and the pleasures that it provided to rely on. If I got in trouble, I could always bargain my way out of it with a big, fat check. When Chapa got in trouble, all he had to bargain with was his big, fat ass.

It was a brief moment of mental clarity before my brain returned to indulging in the pleasures of the flesh laid out before me. I dug my fingers hard into his huge, flabby cheeks. Chapa relaxed his crack and then tensed quickly, smacking his cheeks together with my cock sandwiched in between. He bounced them open and clenched again, forcing his hot, quivering butt flesh into another jiggling shockwave on my dick.

"Shake it. Shake that ass for me, whore!" I smacked his ass and moaned. The cum boiled in my balls. "Fuck!" I cried. My hips bucked upward and I began to cum. My dick spurted hot globs all over the inside of my underwear.

Chapa bounced and shook on my dick until he'd coaxed all the sperm out. I realized after the euphoric high was over that I'd just let him give me another cheek job. I had the overwhelming urge to extricate myself from this embarrassing, painfully familiar situation. Only this time, Chapa didn't let that happen.

Right after I'd spent my load he sat his whole weight down on my lap. His ass seized my shrinking manhood in its powerful grasp, and he pressed his back hard against my face and chest, sure to make his entire, colossal body felt by me all at once.

"What are you doing? Get off me!" I protested.

"I don't whore no more. Take what you said back. I ain't your whore."

I felt like I was hyperventilating under the heavy, sweating cover of his body over me. "I take it back! I'm sorry. I don't think you're a whore!"

Chapa rubbed his soft ass in a circular motion around my crotch. "Tell me you like the way I make you cum. Say I make your cock hard."

"I do. I like it! You make my dick so hard!"

Chapa stood up and got off me, but he didn't get out of the way, keeping his enormous rump right in front of my face. "You're the slut," he said. "Kiss the ass."

I bent forward and pressed my lips to his bulbous right cheek. I kissed the smooth skin without hesitation. I kissed again, turned my face and rubbed my cheek against his soft derriere. Chapa seemed to like this. I twisted my neck and kissed right at the crack of his ass.

Instead of getting rid of him quickly like last time, we shared a drink and an enlightening conversation. Chapa told me of how he'd been caught stealing. He was locked up for it, waiting to be hanged. He only survived by giving one of the guards a cheek job and getting smuggled out in exchange. Chapa realized after that he was better off using his booty skills to get by over being a thief and perhaps getting caught again.

He revealed after a couple more drinks that he'd offered cheek jobs to a few patients over the years. If their illness was terminal and he felt badly for them. He extended the invitation to comfort them with his ass in the hopes that it might ease their suffering.

I asked him how those proposals went over and he responded after gulping down another drink. Chapa said the reaction to his kind offer was mixed. Some gratefully accepted, some spitefully declined. It sounded like a lot of abuse to take for nothing in return. I didn't understand why he bothered. Chapa told me it was worth it for the patients who did accept and were grateful. He was able to feel like his butt had brightened their day.

A notion crept up on me slowly enough to not be startling, that was there was more to Chapa than met the eye, more than just his eye-popping ass. I began to count the ways I enjoyed his company more than the stuffy companionship I shared with those closer to me on the educational and economic scale. There were many.

I discovered a new development the next day. I wasn't afraid of getting caught anymore, nor embarrassed or remorseful about what Chapa and I were doing. We achieved some success on the training front when I switched gears away from teaching him erudite facts of medicine, instead focusing in practical work like cleaning and sterilizing equipment and environment. I hadn't given Chapa's willingness to work hard and take direction the proper credit. He got his job done.

I did something that I think caught both of us by surprise when during the middle of the day, I palmed his ass, with patients and nurses dangerously close by. My cock grew as I kneaded his meaty cheeks. Chapa gave me a curious look before bending his butt back to give me better access. I gave a look around us, confirming we probably wouldn't be caught, and then lined my crotch up with his ass.

We pressed against each other, grinding my cock against his massive rear end. His hot cheeks squeezed my shaft, making me moan and almost revealing what we were doing to others. We quickly decoupled. My face turned red, but my cock still ached for release. Chapa and I made plans quietly to resume what we were doing after work when we'd have the privacy we needed. The rest of the day seemed to stretch on forever.

Back in my office after all my rounds were done, Chapa bent his huge ass over my desk. We'd both stripped our lower bodies down to the nude this time. I came up behind him and inserted my cock between the fleshy globes of his ass. Chapa's impressive crack tightened around my manhood, then he reached back around himself and manually pressed his cheeks even tighter around me.

I thrust my cock in and out of the narrow, sweaty ass groove he created, while manhandling the big cheeks in my hands. I grunted out my enjoyment, Chapa's ass supplying me with all the comfort I could ask for. This was the first time that the bare skin of my cock was able to feel the bare skin of his crack. The heat was intense with my cock fully buried, thrusting through the sweaty friction of his clamped ass.

I spread the gigantic cheeks around my manhood and became enamored by the small hole within. It looked scared and cornered, being pursued by my swollen cock head. I felt like the one in the position of power now. His little chocolate hole was vulnerably close to the tip of my cock and I could make a move on it at any time. I imagined Chapa grunting and squirming around on the desk if I were to bury my cock into his smothering anus.

"What if I put my dick up you right now?" I'd abandoned my thrusting between his cheeks and was now strumming the head of my cock against the ridge of his asshole.

"I ain't letting you fuck me on your desk like some dirty whore. You won't get me like that."

My cock was doing the thinking for me and his pucker was calling it. "What if I just stuck it in right now?" I smeared the pre-cum dripping from my tip onto his twitching entrance.

Chapa's lower body flexed, his gigantic cheeks seized my rod tightly. He reached behind and grabbed my small wrist in his large hand and squeezed it equally hard. "You want to stop now?" he asked.

"Okay, let's forget it. Just let me use your cheeks to cum."

Chapa rolled off the desk and pushed me away. Then he steered my body over to my desk chair and pushed me into it. Chapa sat down on my lap, facing me, and began to dance and shake his massive ass on my cock. I was really getting into it again as his big, hot cheeks clenched my shaft when he stopped again.

"Come on, Chapa. Please. What are you doing?" I complained.

"Tell me you love it," he said, pressing his face to mine.

"Ugh, Chapa, what are you doing to me?" I reached around and grasped his fat, doughy cheeks.

"Tell me you love it and I'll finish you off."

I groaned. "I love it. Okay, I love your big, monstrous ass. I need it."

"That's all you had to say," he told me. Then he kissed me forcefully on the lips, his fat tongue propelling deep into my mouth.

I was taken aback. This was the first time we'd done anything like this. In my head I wanted to protest. I didn't want to be kissed by him, but my body didn't seem to mind. My cock pressed stiffly into the soft, warm dough of his dark cheeks.

Chapa eventually broke the kiss and chuckled nervously. "Let me finish you off," he said, his ass clutching and massaging my cock with more vigor.

I knew I was already close before the savage grabbed my shaft and aimed the tip right at his chocolate hole. "This what you want?" Chapa asked. He rubbed the head against the raised skin of his hot opening.

"Oh god, Chapa. I can't take it anymore, don't stop!" I moaned and groaned as the cum boiled in my balls. My face contorted and I bit down hard on my lip as my cock exploded against his asshole. I covered it in nasty, sticky strands of semen. Chapa held my shaft in his large hand and rubbed the cum in right on his little brown pucker.

I sighed gratefully as his hand finally released me and he sat down fully on my lap, my thankful cock wedging snugly between his big, sweaty butt cheeks.

"So you want to fuck me?" he asked, finally cutting through the silence.