Rob is on parole, which means obeying the legendary Mr. Gerald. He’s a stern, no-nonsense man who doesn’t mind cracking skulls and kicking ass… and he goes even further than that. But when Rob asks to receive one of Mr. Gerald’s harshest of punishments, they’re both in for a wild ride they didn’t expect!
Can Rob handle what Mr. Gerald is ready to dish out?
Read the whole thing here
Rob had six months of parole, and he was looking forward to it. He had been assigned to “Mr. Gerald”, an ex-drill sergeant. Rob had had to pull a few strings to make sure he was assigned to Mr. Gerald’s caseload. He sought that out because, according to street rumors, Mr. Gerald was known to force his parolees to jerk him off.
That was something Rob was down for indeed. Mr. Gerald was buff like a soldier but just craggy enough, like a stately butte. His nose was splatted like it had been broken many times or maybe just once but really badly. His skin was dark like new cast-iron, and his eyes were old like a wise turtle. He had a simmering grandness to him, like he thought he was more muscular than he was, he was actually kind of lanky.
He had a great mustache too. Rob was a sucker for a black guy with a mustache. He wanted to suck the hairs right off his upper lip. And he had big broad shoulders that shook as he filled out a form with Rob’s personal information on it.
“So you work as a writer? A freelance writer?”
“Yep.”
“That don’t sound like a real job. I want you to get a real job,” Mr. Gerald said.
“Yes, sir,” Rob said. He wasn’t going to do that, but he wanted to be agreeable. Rob’s family was very wealthy. He didn’t have to report that on his intake documents, so he didn’t mention that he was in no need of a job.
If he was going to get punished by Mr. Gerald, after all, he was going to need to fail at something.
“Do you have any skills?”
“Just-“
“Don’t say writin’, man.”
“Then no. Sir.”
“Alright, I can hook you up with a job at Taco Dell. I know the manager there. I like the way you called me sir without me…” He looked Rob up and down and sucked on his lower lip. The mustache on his upper lip quivered. “Without me makin’ a big deal out of it.”
Damn it. That was it, Rob thought. If Rob hadn’t called him sir, Mr. Gerald would have throated him down, he was sure of it. That was what the look on his face said. Damn it! He was looking for a reason to do it.
Black guys don’t call him sir, probably. That was why they said on the street that Mr. Gerald only or especially goes after black guys. He’ll nut on a nigga face, nine times outta ten. He don’t even wanchu to swallow. He wanna see you walk outta there with nut on yo’ face, telling him thank you the whole time. He like that. That’s what one of the hobos Rob jerked off last week told him. His name was Greenbelly, and Mr. Gerald was looking for him.
Rob wasn’t gonna snitch though, and anyway, he didn’t know where Greenbelly was. Or his real name for that matter.
“Oh, uh…” Rob blushed. He quaked. Had he gone through all this for nothing? He was entranced by Mr. Gerald’s big muscles, his biceps bulging from the rolled-up sleeve of his stained and faded button-down shirt. He wasn’t married, that was obvious. He didn’t wear cologne. His mustche was neat but his scruffy beard hairs were not thoroughly shaved, like he had done it without a mirror. His shirt had an old mustard stain on it. No wife would let him outta the house in that shirt.
Mr. Gerald wordlessly filled out his paperwork. “You do drugs?”
“No, sir.”
“You’re gonna do a piss test next time,” he said. He glanced up and made eye contact with Rob. “What? You look mad. What?”
“It’s just…” Rob took a deep breath. He decided to be blunt with him. “I heard a rumor about you, Mr. Gerald.”
“What? I don’t like rumormongering. I don’t condone it. A man should stand behind the shit he says,” Mr. Gerald said.
“I heard… you sometimes make guys jerk you off.”
Mr. Gerald glowered at him. His dark eyes were expressionless. “What? You insinuatin’ I force my parolees into somethin’?” He watched Rob pop one of his fingers into his mouth and sucked on it. “Mothahfuckah, you think I can’t get a woman? That is fucked up. That ain’t no kinda thing I would ever do,” Mr. Gerald said with a raspy frown and a wag of one callused finger. “And I resent you for bringin’ up that kinda scurrilous accusation.”
“Oh, I’m sorry-“
“That kind of b’avior would violate the Department of Corrections’s Pillars of Respect, and any nigga who know me knows that I am all about the Pillars of Respect. I know you haven’t yet watched the video about the Pillars of Respect, but when you do, you will unduhstand that they is at the heart of… you know, all the bullshit.” He sniffled as he lost his train of thought. “If you act propuh, I will let you skip the video.”
“I will do literally anything to skip that video,” Rob said.
“Shut yo’ lie-hole, Mistuh Winthrop. Ain’t not a soul make no kinda accusation of that sort. Sometimes motherfuckahs be beggin’ for a way to prove how much respect they got for me. Y’know… sometimes, motherfuckahs be thinkin’ callin’ me sir is the worst thing I could force ‘em to do… only the trick is, I can’t force ‘em to do that. I can’t pull no words outta someone’s mouth. So I gotta focus on gettin’ respect out of ‘em through some other means. Ya feel me?” He stood up and came closer to Rob. He grabbed him by the chin and played with his lower lip. “You wanna jerk me off?”
“Yes!” Rob immediately moved to grab for his crotch, but Mr. Gerald slapped his hand away.
“I ain’t say you could. I was just doin’ a survey, like for gauging general interest among the populace,” Mr. Gerald said. He pointed to a spot on the floor. “Get on yo’ knees.”
Rob did as he was told. His heart thumped. He was going to get to do this after all.
“You know our meetin’ is done, right? I ain’t keepin’ you here no more? I’d rather you leave, to be honest,” Mr. Gerald said. He unzipped his slacks and pulled out a massive cock with a big veiny shaft. When Rob went for it, Mr. Gerald slapped him. “I ain’t consent to you touchin’ it. I’m still makin’ sure you know I don’t like you, and I don’t want you touchin’ my dick. This ain’t how I get off. I ain’t like that. Strikes me as unbiblical,” he said. “That ain’t the parole department’s opinion, mind you, that’s a personal thought, and I gots a right to it.”
“Yes, sir.”
“I think this is a tool,” he said. He flopped his limp dick onto Rob’s face. Rob opened his mouth to lick, but Mr. Gerald slapped him again. “Get that tongue back in yo’ mouth, boy. This here is my tool, not yo’ lollipop. It’s a tool I use to insert respect back into mouthy motherfuckahs who lost they respect in some tragic accident. Ya feel me?”
“Yes, sir.”
“Now, I am gonna ram you in the throat cuz you asked me nice and I like the way yo’ lips is all soft and shit,” he said. He rubbed Rob’s lips with one callused finger. “Don’t you dare be spreadin’ none of them falsities ‘bout how I make men jerk me off. I don’t do that. That’s contrary to Pillars Two, Four and arguably Five of the Pillars of Respect.”
“Yes, sir.”
“You seducin’ me right now. You turnin’ this office into a hostile work environment ‘gainst me, boy. I oughta cite you for that,” he said. He chuckled throatily as he spread Rob’s lips with his fingers and rubbed his limp dick over Rob’s gums and teeth.
He still wasn’t trying to get hard. His dick was just slightly firm, one stage up from jiggly. It flopped like a lively snake over Rob’s face, He chuckled. “Hmm-hmm…” He licked his teeth. He left his dick on Rob’s nose. “Lotta my men would be buckin’ right now. You submittin’ just right.”
“Thank you, sir.”
“You ramrod men?” He battered Rob’s face with his spongy dick. “You ever do it, you know, stick ya dick in a nigga? Or a Arab or whatever?”
Rob nodded. He straightened his posture. “Yeah, I-“
He slapped Rob across the face. “Not me, if that’s what you thinkin’. I was — how much is you into it? I was not asking ’bout me. You wanna ramrod a morbidly obese Arab man? He hairy as shit. Too fat to shower. Five hundred pounds. He bathes with a rag on a stick, sometimes, when I tell him to. I woulda done ramrod the ever-mighty fuck outta him cuz he bin breaking the rules, but I don’t wanna put my dick in him.”
“No, I don’t… I don’t wanna do that,” Rob said.
“Hmm-hmm.” He wrinkled his nose. “Can’t say I blame ya.”
“He sounds like he has a mental health problem-“
He slapped Rob again. “Don’chu think I know that? Mothahfuckah, you got a solution for it-?”
“No, I just-“
“Then shut the fuck up, don’t point out problems you don’t got a solution for,” Mr. Gerald said. He mollywopped Rob with his dick, which had grown even limper now, it was jiggly all the way. He snarled at Rob. “Pissy shithead.”
“Sorry, sir,” Rob said. He shrugged. “What’d he do?”
“Raped his aunt. She got that Down syndrome.”
“Oh. That’s bad. Shouldn’t do that.”
He slapped Rob again. “What’d I say ’bout pointin’ out problems you don’t got a solution for?”
“Sorry, sir,” Rob said again. He stuck his tongue out, and it got the underside of Mr. Gerald’s dick.
“Anyway, Mistuh Winthrop, you doin’ good. When one my men is actin’ insolent, suckin’ on his teeth like a nigga do, I make him sit here wit’ my dick on his face during my spiel. You wanna keep it there durin’ my spiel?”
“Yes, please.”
“A’ight.” He cleared his throat, which made his dick jiggle atop Rob’s face. “Well, first of all, you got any street names? I gotsta ask.”
“No, sir.”
“You gotsta report to me any nickname you evuh used.”
“Ever?” Rob chuckled, making the dickfat resting atop his fce jiggle. “Well, some friends used to call me Winclap, cuz… well, it’s a long story-“
“Do not tell me a long story, mothahfuckah.”
“Okay, uh… Some other friends used to call me Jaxwing, which was my D&D character, uh, R-Queen, Throat Queen, Neck, Other Rob — that was when I was in rehab, we weren’t allowed to use last names, for confidentiality. I think that’s it,” he said. “Oh! My brothers call me Babywrist.”
“Any those got gang connotations?” He looked down at Rob, then slapped him again with his dickmeat.
“No, sir.”
“Okay, well if I catch you usin’ any unapproved nicknames, I’m sendin’ you to the big house! For…” He looked at Rob’s file. “Six weeks.”
“Yes, sir.”
“If I catch you watchin’ any video pornography, I’m sendin’ you to the big house. That’s pervert shit, I don’t like that, that’s disrespectin’ women, I-“
“Yes, sir.”
“Shut up,” he said. He slapped Rob. “Don’t interrupt me.” He cleared his throat. “Stick out ya tongue.”
Rob did so. Mr. Gerald grunted, grabbed his tongue with two fingers and pulled it out so far it hurt. He rested his piss-slit on it. He waited to see if Rob would object or pull away or gag. He did not.
“Next. No catcallin’ at females, no gettin’ fresh wit’ a woman, and it’s up to the woman or me to decide what’s fresh. I don’t need yo’ input on freshness,” Mr. Gerald said. He wagged his finger at Rob, which made his dick jiggle clear off Rob’s face. Mr. Gerald put it back. “Next. You can’t be homeless. If you homeless, you stayin’ wit’ me, and I am ramroddin’ you e’ery chance I get.” He bristled. “Scratch that, you’d prolly enjoy it.”
Rob nodded without remove his tongue from Mr. Gerald’s dicktip.
“If you homeless, I’ll make you spend the night somewhere you don’t like. Where there’s no musical theater and no club music,” he said. He chuckled. “You is required to go to the religious institution of yo’ choosin’, and yes I is allowed to do that, if you atheist, you go to the humanist group at the university, okay, and just like hell it’s full of atheists and feminists, so it’ll be a preview of yo’ future,” he said. “This town gots churches, mosques, synagogues and some Hindu things and things that ain’t quite Hindu but I don’t get the difference. And a Buddhist thing. You pagan?”
Rob shook his head.
“Good. Which church you go to?”
“I don’t have a regular one, I, uh…”
“You go to First Grace from now on,” he said. “I know the pastor. I’ll be checkin’.”
“Yes, sir.”
“Hmm-hmmm…” He paused. “You Communist?”
“No, sir.”
“Good. You one them Satanists?”
“No, sir.”
“Good.” He slapped Rob. “I won’t be respectin’ no Satanism as a religion, and the Supreme Court can say that to my face!”
Rob chuckled cuz his words didn’t quite make sense, but he got the gist, and he settled down when Mr. Gerald glared at him like he better not point that out. Rob stuck his tongue back out onto Mr. Gerald’s piss-slit. His tongue was getting dry though. He chased the tip of Mr. Gerald’s dick til he saw that glare again, then he settled still.
“You may open yo’ mouth.”
Rob did so, as wide as he could, and he waited for Mr. Gerald to signal he could proceed. Rob then swallowed his dick down to the root. It was starting to get hard, that must be why he decided to move on, and in Rob’s mouth, it rapidly firmed up. He looked up at Mr. Gerald’s surprised face — he probably didn’t normally get dome from guys who could deep-throat like Rob.
Mr. Gerald held onto the back of Rob’s head and plowed into him, treating his mouth like it was a pussy. His balls slapped against Rob’s chin. He held onto Rob’s ears.
“You doin’ it good, boy, no gaggin’ at all. They comin’ out wit’ good white boys these days. It’s been awhile since I had a white boy who could take my dick this good. Try to swallow the whole thing, you feel me?”
He nodded, and Rob relaxed his throat. Mr. Gerald pinched his nose shut, which helped his throat open even wider, and he got more, more than half of his shaft, to squeeze down Rob’s throat. Rob choked. Mr. Gerald clucked his tongue.
“Nah. Stay like that.” He lightly slapped Rob’s cheek. Rob again bucked as his throat rebelled, and his eyes bugged out. Then at last Mr. Gerald pulled his dick out and let him take a breath.
“Thank you for lettin’ me breathe, sir,” Rob said, panting between words.
“Hmm-hmm…” Mr. Gerald said. “You wanna swallow my nut, or you want me to paint you white?”
“Swallow.”
“Good. I don’t like nuttin’ on a white man, cuz you can’t see it. If you was darkskin, I’d paint you white as pigeon shit,” he said, and he let out a bellowing cackle. He clapped his hands. His balls jiggled on Rob’s chin. “I’mma fuck yo’ mouf a little, like a pussy.”
Rob nodded.
“T’weren’t a question, and I don’t need feedback on it,” he said. He held onto Rob’s ears and rammed at his mouth, firm but not hard, more humping his tongue than “fucking” his throat. Rob grabbed his muscular thighs, but Mr. Gerald slapped his hands away. “Don’t touch me, freak.” He chuckled. “Oh, yeah, no beard. Don’t grow a beard. I won’t wanna use yo’ mouf if you got a beard.”
He reached behind himself on the desk, and he picked up his phone. He unlocked it, then scrutinized something he seemed to find annoying. He wrinkled his nose at it. Then he swiped to something else, and he showed Rob the screen.
“See? This is a website about female rugby,” he asid. “It’s not pornography.”
Rob nodded.
“Good. I ain’t bein’ hippocritical. Some niggas is makin’ ‘ccusations ’bout that,” he said. He seemed about to say something else, but he saw a rugby player he liked and his words melted into a low hum. His dick pulsated against Rob’s tongue. “Hmm-hmm… Lookit them thighs, nigga…”
Finally a burst of salty precum exploded in Rob’s sense. That must be one sexy female rugby player, Rob thought, because Mr. Gerald’s meat raced from mostly hard to spewing precum and throbbing mightily in about two seconds. He wondered what race the rugby player was. He wished he could ask without taking his mouth off Mr. Gerald’s cock.
“How nasty you get, boy?” he asked.
“Very.” Rob’s voice was muffled by a mouthful of prenut, which he neither swallowed nor spat out.
“Good. That was the right answer,” he said. He pulled his dick away, then he stood up off. He motioned to the desk. “You. Bend ovuh that.”
Rob raced to comply. He was about to drop his pants, then he realized Mr. Gerald didn’t tell him to do so, he so he stopped. Then he realized he’d enjoy the punishment for doing it anyway, so he did it anyway. His jeans plopped to the floor around his ankles, and he shimmied down his underwear. That bared his pale ass, which Mr. Gerald grumbled at.
“Hmm-hmmmm, I don’t appreciate too much eagerness, boy,” he said. “I ain’t say to take yo’ ass out.”
“Sorry, sir. You wanna spank me-?”
“What? No, I ain’t toleratin’ no kinda BDSM nonsense, boy, and that’s another thing that ain’t allowed, don’t go aftuh me with none that free association shit neither, I will wallop you, straight up wallop! No kinky shit. No leather, no whips, no chains, I don’t care how consentin’ it is, no way,” he said. “No feet!”
“No feet?”
“In sex. You can keep yo’ feet for walkin’ on,” he said.
“Okay then,” Rob said. He looked behind himself, but he couldn’t see Mr. Gerald.
“Don’t worry ’bout me, you keep lookin’ that way,” he said. “You see that clipboard on the desk?”
“Yes, sir.”
“Grab it. Fill it out. That’s yo’ form 10G, you best respect it.”
“Oh, I do.”
“The state mandates you fill that you e’ery week. Actually it mandates I fill it out, but I am not fillin’ it out, you bitch-ass punk, you is doin’ it,” he said. He punched Rob in the meat of his asscheek. It hurt much worse than Rob was expecting, and he yelped. Mr. Gerald barked. “I said fill it out!”
Rob raced to do so. At the bottom was where Mr. Gerald was supposed to fill in the answers to the standard parole questions. There were two additional pages of follow-ups. It included everything from “how many lawfully registered firearms are in the place where you live?” to “do you know of the whereabouts of any of the Missing or Endangered Indigenous Women of the Dangerously Ignored Serial Killer Murder Epidemic of the Western States?”.
“What’s with this murdered indigenous women thing?”
“You murder any indigenous women?”
“No.”
“Then just write down no.”
“You have to ask me that every week?”
“Yep. So, y’know, keep track.”
“Also, I haven’t asked any of my acquaintances if they’ve violated the Somali Warlords Act of 2003,” Rob said. “It’s entirely possible I know lots of Somali warlords.”
“You know any Somalis?”
“I don’t judge people by the color of their skin. Anybody can be a Somali warlord.”
“Just put no!” Mr. Gerald said with a snarl. He was deeply engrossed in the rugby women on his phone, and it sounded to Rob like he had gotten distracted watching video clips from an actual women’s rugby game. “Them Polynesian girls is hefty. You know ’bout them?”
“Yeah,” Rob said. “I’ve been to Samoa. It’s nice, the women are huge.”
“Really? You know any Samoan women in the US?” Mr. Gerald asked. He stabbed his hardon between Rob’s asscheeks, and he leaned in, pushing it at his butthole. “Don’t lie to me.”
“I do not, sorry,” Rob said.
“Lookit them thighs, damn…” Mr. Gerald showed Rob the phone but the glare made it impossible to see. “She could squeeze the nigga outta me. Make me white as you, shit!” Rob didn’t care. He opened his asshole the best he could, practically sucking Mr. Gerald’s dick in.
A surge of both pain and pleasure hit Rob, and Mr. Gerald grunted. He dropped his phone, which landed on the small of Rob’s back. Mr. Gerald grunted again. Rob put down the clipboard.
“You finished that form 10G?”
“No.”
“Boy, if you don’t finish it, I will slap the senseless outta you,” Mr. Gerald said. He thrust his hips, forcing more of his dick into Rob. He began gently sliding his cock out but firmly ramming it back in, each time upping the pleasure like a ratchet where it boiled within Rob. Rob clutched the desk underneath him, and he knocked the pen he had been using onto the floor.
He grabbed another pen. He groaned. The sensations emanating from his ass were enormous, and Mr. Gerald’s pounding was relentless. He looked at the last question. “What are my aspirations for the week?”
“That’s right.” Mr. Gerald said. His voice wavered with each thrust of his hips. “Hmmm… hmm…” He tried to play it cool, but his voice broke and he let out a little moan, which he stifled. “Aspiration means goal.”
“Yes, I get it, I just… My aspiration is to take your nut in whatever hole you want it,” Rob said, panting, writhing, wanting to be for more.
“Hmm-hmmm… That’s a very good answer. It’s a wrong answer, but it’s the best wrong answer,” Mr. Gerald said. “The right answer is to stay outta trouble, worship Christ and obey yo’ boss, landlord, pastor and officers of the law. Spelling does not count.”
Rob struggled to write all that while Mr. Gerald pounded at his sensitive ass. Bliss exploded with each pump of his hips, and the entire hugeness of his shaft went in each time. Rob suspected few of Mr. Gerald’s parolees took the whole dick up their ass. It was actually quite difficult to force a man to take a big dick in a hole that both doesn’t want it and is too small for it, and probably it was more effective as a deterrent than a punishment. Rob, however, was eager to be punished, not deterred.
All at once, Mr. Gerald stopped. “Oh, you goin’ to First Grace from now on. In the basement of that church, boy, there’s a man, his name is Cassius, he’s an old retired boxer. He kinda retarded. If you tell him you’s me, he’ll believe you and bend ovuh, you can ram him all night long if you want. I did. Trained him good too,” he said. “He’s kinda old, but his ass is still tight. You’ll like him. He’s bettuh than that fatass Arab fellah.” He clucked his tongue. “I dunno what to do about him.”
“I’ll check out Cassius,” Rob said through his gasps of pleasure.
“You gonna do ass-to-mouth?”
“Yes, sir, please!”
“That wasn’t a question.” He grunted.
It sure sounded like a question, but Rob didn’t say so, as a burst of relief made him moan out loud. Mr. Gerald pulled his dick out. It felt so good Rob’s knees went weak. Then Mr. Gerald shoved him to the ground.
He rammed his cocktip back into Rob’s mouth, and the grimy flavor of Rob’s own ass filled his senses. Rob cried out around the dick in his mouth. He couldn’t help but grab his own cock and stroked it, instantly triggering his own orgasm.
Jizz spurted onto Rob’s chest and some onto Mr. Gerald’s legs. He didn’t notice because he closed his eyes as he humped his giant ass-coated cock on every inch of Rob’s tongue, then plowed down his throat like before. He again pinched Rob’s nostrils shut so he could go all the way down.
“Alright boy, no spillin’ my nut, that ain’t respectful,” he said. “Violates Pillar Two.” Then he chuckled. “What am I sayin’? I ain’t gotta tell you not to spill. I bet you love swallowin’ nut.” His chuckling broke as he orgasmed. “Hnnnn-hmmmmm….” His whole body undulated, and he closed his eyes.
He slammed his dick all the way in. Rob could feel him orgasm in the throbbing of the vein on his dick, which pulsated against Rob’s tongue. But Mr. Gerald’s dick was so deep in his throat that Rob didn’t taste the actual cum at first, just the precum that already coated his shaft.
“Hmmm… boy, you drainin’ me, that’s good…” His voice was low and rumbly like velvet sandpaper, and he bucked his hips, making sweet love to Rob’s throat. He gripped his hair tightly, rubbing his crotch and balls all over Rob’s face.
Finally, he pulled out, and the taste of salty-sweet cum assaulted Rob’s senses. He moaned and swallowed every drop, even as his belly contorted and his lungs cried out for oxygen. He slathered Mr. Gerald’s dick with spit and cum as he let it slowly plop out.
“Goddamn, boy.” Mr. Gerald said with a chuckle.
Rob gasped for air. “Hmmm… You taste so good… I love your dick, Mr. Gerald, I-“
“Hush. I don’t need you to talk,” Mr. Gerald said. The mustache on his upper lip quivered. He sighed and leaned back. “Shit…”
“Hmmm…” Rob smacked his lips and wiped his face off. the smell of jizz and ass coated his mug. “I didn’t spill any, I promise.” He quickly put his own clothes back on. It was always best, he thought, to leave them wanting more, so he intended to leave right away.
Mr. Gerald nodded. “Hey, boy.”
“Yes, sir?” Rob headed for the door.
“I take back what I said about my dick not bein’ your personal lollipop. You can come back and mouth me off whenever you want,” he said. He handed his business card over, with his home address written on it. “Okay?”
“Yes, sir!”
