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?"
