Drew’s First Day of Prison

Twink inmate Drew gets a taste of what to expect from prison life when he new warden gives him a slow and thorough medical examination.
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Drew's First Day of Prison
by drfantasyguy75

Drew gingerly stepped out of the shower and began drying his lean, muscular body, nervously glancing at the guard who stood watch. He wondered why the guy had such a smirk, and as he slipped his underwear on, the guy started to chuckle.

“Really, asshole? Tighty whities?”

“What’s wrong with ‘em?” Drew asked defensively.

“It’s so white trash,” the guard said. “They’ve even got holes in ‘em. Oh well, not like you’re gonna be wearing those for long.”

“Why, are they gonna issue me some new ones? Are prison undies so much better?” Drew asked, trying to sound tougher than he really was.

“It’s not that,” the guard said passing a hand over his thinning grey hair. “It’s just that you’re going in to the see the warden now, and you’re not going to be wearing anything once you’re in there.”

Drew swallowed hard, and although he was petrified, there was something about the way the guard had said this that stirred something deep inside of him, something he couldn’t define or admit, even to himself. If one of his buddies from the road crew had asked him, he would have called it being pissed off or a rebel. The truth was so much harder to face.

“So….uh, why am I not gonna be wearing anything once I’m in there?” he asked.

“Don’t you know? The warden likes to check out the new guys personally. Likes to give ‘em a ‘once over,’ as he calls it. He used to be a military doctor back in the day, so he gives the new prisoners their entrance physicals.”

“Oh,” Drew said, feeling relieved.

‘Just do whatever he tells you to do, and don’t piss him off,” the guard said, slapping the younger man on the shoulder. “He is one crazy-assed dude. Now, put your arms out, and let me put these cuffs on you. It’s regulation, even though you couldn’t escape this place even if you were Houdini.”

Drew put his arms straight out, and the guard slapped the cuffs on his scrawny wrists. “Hmmmm,” he said, as if studying Drew’s rippling abs and bulging biceps. “Turn around, boy.”

Drew did as he was told. The guard slapped him on the ass, hard.

“Just as Warden likes ‘em,” he said with a laugh. “Now come with me,” he said, leading Drew down the hall by the elbow.

Drew tried to think of old, white-haired Mrs. Sample who used to live across from his trailer as they walked down the dimly-lit hall. Why was his cock suddenly so hard? True, he hadn’t jerked off in almost a week, but still…He felt humiliated as the guard led him past a group of dangerous-looking guys who looked like white supremacists or skinheads or something. One of the guys, a red-faced, huge blond guy in an orange prison suit, stared hungrily at Drew, and the young man felt something stir in his loins.

He had never felt so embarrassed in all his nineteen years, and yet, although he felt scared and nervous, he also felt tingly and more alive than ever.

The guard opened a door with one of the keys on his belt and led Drew down a dark, narrow hallway. At the end of this, he opened another thick door marked “Solitary Confinement.” Drew wondered why the warden would have his office in that part of the building, and started to ask the guard about this, but the guy said, “shut the fuck up, scumbag. Don’t say anything from here on out unless you wanna get the shit beat out of you or your ass thrown in with those rapists back there. Got it?”

Drew just nodded, his heart racing. He suddenly felt very thirsty.

The guard led Drew past a bunch of cells that had only a small window and a slat at the bottom of each door. Drew imagined that this was where the guys were given food and water. He thought he heard someone pounding against the walls somewhere, and wondered if these cells were padded or somehow soundproof.

Finally, at the end of the hallway, the guard stopped Drew in front of a thick wooden door. “This is it, kid, he said. “Good luck. And remember, just be good, and don’t piss the warden off. If he likes you, you’re golden,” he said, reaching down and caressing Drew’s buttocks through his tattered underwear. “Oh yeah,” he said with a grin. “Warden’s gonna like you.”

He knocked on the door, and a moment later, it opened.

The warden wasn’t anything like what Drew had imagined. He had been thinking he might be a stocky, blond guy with a military buzz cut like his own, but instead, the warden was tall and muscular. Italian-looking, almost like a cross between Stalone and George Clooney. He was very tall and tan with a five o’clock shadow. He was so dark that Drew wondered if he did indoor tanning or something. His tan skin contrasted sharply with the white medical coat the man was wearing. Drew wondered how old he was, but couldn’t decide if the man was forty or sixty. His stubble was dark, however, and his hair was salt-and-pepper. Drew once again tried to think of old ladies, as his penis had gotten rock-hard once again. Why did it always do that? It was like that one time during gym class in high school when Mr. Corpioli was checking the boys for spinal problems….or that time with Father O’Malley….

“This must be Drew,” the warden said, obviously noticing the young man’s erection. “Come on in, young man. I’ve been expecting you.”

Without a word, Drew walked into the warden’s office. He wasn’t expecting it to feel so comfortable. His bare feet felt a warm shag rug, and the room was a soft, comforting brown color. Accent lamps gave a friendly glow to the room which was much better than the harsh fluorescent lamps of the prison hallways. The soft sound of classical music wafted in from somewhere.

“Thank you, Edward, you may leave us,” the warden said. “No need to wait outside, just give me Andrew’s key and you can leave him to me,” he said.

The guard handed over the key, and gave Drew a wink.

The warden locked the door, and turned to face Drew.

“So, young Drew Foster. You’ve been a bad, bad boy, haven’t you?” The warden said, and Drew was surprised how relaxed he suddenly felt. The man’s voice, although seeming harsh and commanding, was strangely intoxicating, as if every word were sweet wine.

“Um, I guess so,” Drew said, looking down and hoping his erection wasn’t noticeable.

The warden took a step closer. “Assault and battery. Breaking and entering. Attempted kidnapping. Tisk, tisk, young man. Three strikes and you’re out in this state. Or rather, should I say, you’re in. As in, in my prison. For life.”
Drew just looked down. If only he hadn’t let Anthony talk him into doing that shit. And if only Drew hadn’t been such a good friend, and taken the fall for him. Now the asshole seemed to have forgotten all about him, had probably moved on to other destructive friendships and left Drew to rot in prison, alone.

The warden took a step closer, reached out, and put one finger under Drew’s chin. “While you are here, boy, you will live by my rules, and mine alone. You will obey me, and do whatever I say. Is that understood, boy?”

Drew nodded and said, “Yes.”

“Yes WHAT!” The warden said, stepping closer. His dark drown eyes were fixed on the boy’s blue ones, and Drew could feel the man’s hot breath on his cheek, could smell his aftershave. The warden put his hands on Drew’s shoulders and drew him closer. “Yes WHAT, boy?”

“Um, yes, sir?” Drew stammered.

“That’s better,” the warden said, taking a step back. “You see, I’m really a very reasonable man,” he said. “I think you’ll grow to like it here, under my care. I’ve been able to mold many wayward boys into the kind of men I want them to be.”

Drew only nodded, deciding to say nothing.

“Now, it will be my pleasure to give you your entrance physical. I am, as you may have heard, a very “hands on” kind of warden, and the state gives me a lot of leeway. So, even though I am no longer a practicing doctor, I will be conducting your physical exam today. Is that OK with you, my boy?”

“Yes, sir,” Drew said meekly.

“Good. Then, won’t you take a seat?” The warden said, and drew was glad to be able to sit on the cot behind him, because he was beginning to get hard again. Drew thought that maybe he could explain that he got hard when he was nervous sometimes.

But this time, the warden didn’t seem to notice. He sat behind a large, brown desk and rifled through some papers. The warden opened a manilla folder and began reading a file, which Drew assumed must be his. “Hmmmm,” the warden said, frowning.

“What’s wrong, sir?” Drew asked.

“Don’t speak until spoken to, boy,” the warden said, throwing him an angry stare.

“Sorry, sir,” Drew said, softly.

The warden went back to reading. “Says here you haven’t had a proper physical in many, many years. I find that surprising. Didn’t you play any sports in high school?” He asked, getting up and walking slowly toward the cot where Drew sat, nervously watching him approach like a panther approaching its prey.

“No, sir,” Drew said. “Me and my mom, we were too poor to afford any equipment.”

“By the looks of things, not having nice equipment isn’t a problem for you,” the warden said and he stared hungrily at Drew’s crotch. “Make a muscle for me, boy.”

Drew did as he was told.

“Very nice,” the warden said, sitting next to the young man. “Very nice indeed. Keep flexing. Very nice. How did you get such a nice physique?”

“Working on a farm, mostly,” Drew said. “Then, later on, working on the road crew, after my ma died.”

“Stand up for me, boy,” the warden commanded. “Stretch your arms to the ceiling.”

Once again, Drew did as he was told. Slowly, the warden stood up from the bed, and began running his fingers along Drew’s back muscles, then along his shoulders, and slowly, up along his arms. For what seemed like an eternity, the older man caressed Drew’s muscular arms and shoulders. As his large, powerful hands explored the blond tufts of hair in his armpits, Drew fought to keep from giggling or showing any discomfort, as he had always been ticklish.
“Well this will have to come off immediately,” the warden said, touching a botched tattoo of an eagle on Drew’s right shoulder. “What the hell is this?”

“Oh, that. It’s supposed to be an eagle, but my buddy fucked it up,” Drew said.

Suddenly, the large warden grabbed Drew and spun him around. While clasping the young man to him, the warden wrapped one large hand around his throat. “You watch your fucking language when talking to me, boy. Got that?”

“Yes, sir,” Drew said. His heart was racing so fast that he thought the warden must surely feel the racing pulse in his jugular.

The warden held Drew close and ran his fingers over the blond scruff coming in where a goatee ought to be. He then fingered Drew’s adam’s apple, something that caused Drew’s erection only to grow larger through his tight shorts. He felt mortified that the warden must feel his throbbing cock jutting into his muscular belly.

“Now, listen to me, boy, and listen well,” the warden said, purring every word as if he were a cat playing with a mouse. “You are no longer your own man. You belong to the state. And that means, in here, you belong to me. I own you now. I can very easily make you disappear into the system. You’re a lifer. You’ve got no friends, no family, and no fucking lawyer. I read your file, my boy. I know that your sorry, white-trash ass had to be assigned a public defender. So I know that no one is going to give a shit if you’re never heard from again, if you know what I mean. Do you know what I mean, boy?”

Drew gulped, suddenly very, very thirsty. “Yes sir, I think I do, sir.”

“That’s good. Now, are you going to be a good boy for me?”

“Yes sir,” Drew croaked.

“That’s good, boy. Very good,” the warden said. He released Drew from his grasp, and stood staring at the young man for a long moment. “Now, as I said, I am going to give you a very thorough physical exam, probably more thorough than you’ve ever had in your whole sorry life. But the way things turn out is going to determine how your life under me is going to be. If things go well, I will keep you for myself, my own private boy, my own assistant if you will. You’ll be protected, cared for, nurtured. Would you like that, boy?”

Drew nodded, and felt surprised to feel that, in fact, he thought he might like such an arrangement. What was happening to him? Wasn’t he normal?

“OK, then. Because, if things don’t work out….let’s just say that you won’t be too happy. You know those padded cells you passed by getting here?”

Drew nodded.

“Those were some of the guys who didn’t pass their physicals, or pissed me off,” he said. “The other ones I just throw to the KKK guys.”

“Oh,” Drew said.

The warden walked over to the desk where he kept Drew’s file. He picked up a pad of paper as well as a pen and walked back to where Drew stood awkwardly by the old cot. The warden reached into his lab coat and pulled out a plastic cup. “Here,” he said. “Go in the next room and piss into this, I have to run some tests on your urine. Oh, and while you’re in there, you have permission to drink some water from the faucet,” he added.
“Yes, sir,” Drew said, walking to the other room. The warden seemed to be reading his thoughts when he said, “try thinking of the old lady from Titanic.”

Drew followed his suggestion, and was thus able to pee into the cup, which was not easy to with cuffed hands. Coming back out, he sheepishly handed the urine-filled cup to the warden, who was now holding a strange device with a Velcro cuff. “Here, let me take your blood pressure,” he said, and wrapped the cuff around the boy’s arm. Drew tried to steady his breathing as the warden took his measurements, all the while grunting with disapproval and jotting something down on a piece of paper attached to a clipboard. Drew considered trying to explain that he was nervous and this might be affected the reading, but thought better of it.

The older man took off the cuff and told him to hold his hands out, which Drew did. The warden felt his wrist and took his pulse while timing something on his watch. Drew didn’t want to admit that he couldn’t remember the last time he had been to a doctor, and so had no idea what the man was looking for.

“I’ll take some blood samples later,” the Warden said. “Soon, I’ll be selling your blood to the blood bank. I’ve got connections over there, and they’re always glad to get the blood of my guys. Same thing for the sperm bank. People will pay top dollar for the cum my studs put out.”

Drew thought this was kind of a strange thing for his warden to say, but he decided it best not to ask questions.
Next, the man took out a small light, and inspected Drew’s ears. He knew that Anthony’s beds had been reported to have bedbugs, and hoped that none of them had made it into his ears or anywhere else that the warden might decide to probe.

Then, the warden took out what looked like a popsicle stick and told Drew to open his mouth. The young man did so, and the warden held his tongue down and shined his light, just like in the movies. And then, just when Drew was started to lose his erection, the warden told him once again to raise his arms up toward the ceiling. Drew obeyed, and the warden ordered him to turn around.

Drew hadn’t noticed the hook in the middle of the ceiling, and the warden, who was at least seven inches taller than him, reached up and attached Drew’s handcuffs to this hook. There were the sound of a clasp closing, and the warden pressed a button on the wall that raised the hook, and Drew, several inches, so that the boy had to stand almost on the tips of his toes.

Once again, the warden began exploring Drew’s body from behind, only this time, he began at his feet. He told Drew to flex when he got to his calves, and Drew was glad for all the years he had spent biking back and forth to the farm outside of town where he had worked before dropping out of school in tenth grade. When he got to Drew’s buttocks, the warden slowly reached into Drew’s underwear and gently began massaging.

“You’re a hairy one,” the warden whispered, his breath once again hot on Drew’s neck. “I like my boys hairy. You wanna be my boy, boy?”

“Yes, sir,” Drew said. What choice did he have?

The warden’s hands slowly drifted to the front of Drew’s body, and soon they were exploring the hard ridges of his rock-hard abs. “You’re gonna have to work hard to keep this bod hot for me in here, boy. You got that? I’m only gonna let you out to work out in the gym. I have a private gym for my favorite studs. Nothing but gym time and protein-shakes for you from now on.”

“Yes, sir,” Drew gasped.

The warden ran his fingers along Drew’s washboard belly and ribs, which stuck out more than usual. Drew had always been on the thin-yet-muscular side, but he hadn’t had a good meal, or any privacy to jerk off, in almost a week.
The warden’s hands slowly worked their way upward toward Drew’s chest. Soon, they were massaging the young man’s erect nipples, and Drew became aware of how profusely he was sweating, which he hoped would not anger his warden.

“Are you my boy?” The warden purred once again as he massaged the boy’s moist nipples. The man’s fingernails cut as they squeezed hard, making Drew gasp. Soon, the older man was clasping Drew from behind, and Drew could feel a huge erection poking into his back.

“Yes, sir,” Drew said, moaning slightly.

“Whose nipples are these, boy?” The warden asked, once again squeezing the boy’s erect tits.
“Yours, sir,” Drew said without thinking.

“That’s right, boy. They belong to me now. You belong to me, now.”

To this, Drew just whimpered.

Soon, the man’s large hands were making their way down again, and Drew could feel the ridges of his warden’s fingernails cutting into his skin.

“I like this happy trail here on your belly,” the warden cooed, his tongue on young Drew’s neck. ‘I want to find out where it leads.”

“Oh, yes sir,” Drew gasped.

The warden worked his tongue slowly up Drew’s neck, and Drew wondered if the man enjoyed tasting his sweat. Suddenly, the man’s tongue was in his left ear, and he gasped in pleasure. Never had any girl made him feel this way, and he moaned in pleasure.

Slowly, gently, Drew felt the man caress the treasure trail of blond hair that led to the top of his ancient white briefs. But just before they reached the underwear, the warden began exploring Drew’s navel. Soon, the man’s index finger was poking into his navel so hard that Drew thought he would explode. Just as the felt the tip of his dick starting to protrude from his shorts, the warden pulled away from him slightly, although still holding his back.

“Now, I have to make sure all my slaves are in are proper working order,” the older man whispered after what seemed like a blissful eternity of probing Drew’s ear. Slowly, his hands were once again on Drew’s slick chest, and as they moved toward his crotch, Drew moaned as the man’s hands slid along his hairy, sweaty abdomen. Soon, a large hand was gently fondling his balls, and, as Drew tried to wriggle free, the man held him tight. “Turn your head and cough,” he commanded, as he grabbed Drew’s testicles in a tight and forceful grip.

Drew turned his head to the right and coughed as hard as he could. His balls seemed to be crying out for release from the crushing of the man’s grip, but he couldn’t believe how close pain and pleasure could be.

“Very good, good, good boy,” the man cooed again, clasping Drew closer. Slowly, the man released the vice grip he held on Drew’s testicles, and massaged them for a long, erotic minute. “I have to make sure there’s no cancer, no growths on them,” the warden explained. “Whose balls are these, boy?” He suddenly demanded, squeezing Drew’s balls tight and once again crushing his young body to himself.

“Yours, master,” Drew said, without thinking. Why had he used that term?

“That’s right, call me master from now on, no more just plain old “sir.” I fucking own these balls, got that?”

“Yes sir!” Drew said, the words escaping too fast. "I mean, yes, master!” He corrected himself.

The warden slapped his buttocks hard with his other hand, never removing his grip. “That’s right, call me ‘Master’ from now on, slaveboy.”

“Yes, master,” Drew said.

“Very good,” the warden said. He held Drew close for a long moment, and then said, “and now comes my favorite part.”

“What’s that, master?” Drew asked.

“You’ll see,” his master said with a chuckle. He walked over to the desk and took out a red bandana. “But first, I have to blindfold you.” He walked over and unhooked him, then brought Drew’s cuffed hands down to waist level before tying the blindfold on tight, covering the boy’s eyes and most of his face.

Next, Drew heard the man taking off his belt. The thought crossed his mind that he might be about to get a beating like from his stepfather, but instead, his master wrapped the belt around his neck, making a kind of dog-collar and leash for his prisoner.

“Come with me, slaveboy,” he said, grabbing the improvised leash and dragging Drew along. They went back beyond the bathroom, out into what felt to Drew like another long corridor. He couldn’t see anything of course, and, before long, he had no idea where his new master had taken him, as they had walked for at least five minutes turning down random hallways and through what felt like a wet sauna and private gym. Suddenly, Drew heard the rattling of keys, the creaking of a door, and he felt that he was in a small bedroom.

His master placed him on a bed, and Drew felt his arms being pulled over his head, the handcuffs rattling. He felt the cuffs being attached to something-another chain perhaps-and his arms were now firmly stretched out behind him. With the rattling of a key, his hands were momentarily freed, but then were locked into firm, cylindrical leather cuffs . Soon, his master had done the same thing to his feet, and he was spread-eagle on a soft bed.

It had all happened so fast that Drew had not even thought to struggle or resist. He was embarrassed to realize that his penis was now throbbing harder than ever, and, as his master removed the blindfold from his eyes, he looked down to see a large spot of pre-cum coloring his favorite old white briefs.

“Hmmm, you are a horny young man, aren’t you?” The man said, setting up a tripod and starting a videocamera.
“What’s that?” Drew asked, eyeing the camera.

“Oh, I love filming this part of the physical,” the warden said. “I’ll maybe sell this shit, along with your jizz, on the internet later. Sick fucks out there will buy anything.”

“But…..” Drew started to protest.

“You don’t have a say anymore, handsome!” the warden said, poking his finger once again into Drew’s navel, which was again wet with sweat.

Soon, his master was rubbing his hands over Drew’s hairy chest once again. “My, my, you are a hairy and horny one. And such a perfect specimen, in the prime of your life. The juices are definitely flowing in you. Oh, that reminds me,” he said, taking a grey bottle of a shelf.

“What’s that?” Drew asked.

“A special gel,” the warden replied matter-of-factly as he squirted a large amount of the cool liquid onto Drew’s hairy chest, which he started to massage in. “It’s a topical mild steroid. It boosts your testosterone levels and promotes muscle growth and energy. This will have you cumming at least five times a day for me. You probably don’t need it, and I’ll run some tests later to be sure, but I like my boys to have lots of juices flowing, even more than they need medically. It helps keep things fun.”

“But….I mean, don’t I need a prescription for that kind of thing?” Drew asked.

“Not in here, not any more,” the warden replied. “I am your doctor now. And your daddy. And your master. And as your master, I get to decide what is best for you. And if I decide to keep you at your absolutely horniest, well, then, that’s just how it’s gonna be.” He took off his glasses and slapped Drew’s belly, then, reached into the boy’s underwear and began fondling his testicles again. “Yup, you’re just how I like my boys. Young, dumb, and full of cum.” With this, he removed his hand and gave Drew another squirt of the steroid cream, this time on his sternum. “You are so fuckin’ hot,” he said.

As he said this, the warden once again began massaging, then pinching Drew’s nipples. The boy gasped, and his master took two clothespins out of his white smock.

“Guess where these are going?” he asked, and as he put one on each of Drew’s already-sore nipples, the boy gasped in pain. However, he was surprised at how this pain only made his erection grow larger. He looked down to his tattered briefs, and saw that the stain caused by his pre-cum was even larger than before.

“Now, to remove the last vestige of your freedom,” his master said. He reached down, and began cutting the underwear off of him with a pair of old, rusty scissors.

“NO!!!” Cried Drew, but soon, he was naked and spread –eagle before his new master.

“What’s that, slave-boy? Did I hear you say something? Did you fucking say something, you scumbag?”
“No sir, no master,” Drew quickly stammered.

“I didn’t think so, boy. Because, I think that even though you might protest, I think you actually kind of like this. Is that right, boy?” The warden said, massaging Drew’s throbbing seven-inch cock.

“Yes, master,” Drew said, desperation making his voice catch.

“That’s what I thought,” the older man said. “You know, I was there during your psych evaluation yesterday, slave-boy. I bet you didn’t know I was watching through that mirror, but I was. And I said to myself, man, that’s one hot little faggot. And I bet he’s too stupid to know that he even is a faggot. Is that right boy?”

Instinctively, Drew struggled against the leather cuffs. But the cold fact was beginning to sink in: there was no escape.
Then, his master was standing looking down on him. He took off his medical smock, and then took off his striped blue polo shirt underneath and his light kaki pants and brown loafers. Soon, his huge penis was poking out from loose-fitting black boxers. Just the sight of this powerful, hairy, raging stallion of a man made Drew almost swoon, and he threw his head back against the thin bedspread that smelled of sweat and semen.

“And now for my really favorite part,” his master said. “Now it’s time to collect the sperm sample.”

Once again, Drew strained against the leather, but to no avail. His master just laughed.

“Fight all you want, you little piece of meat. You can’t escape. And even if you could, where would you go? My guards would bring you right back to me, and then I would beat you to within an inch of your life. So, just accept the fact that you belong to me now.”

The man reached over to a shelf beside the bed and squirted something into his right hand. Soon, while one hand was squeezing Drew’s testicles, the other, lubricated hand was slowly, methodically moving up and down Drew’s throbbing shaft. Drew was disappointed to see that his erection had returned, and was betraying what was left of his resolve. He knew that any second, he would be spewing a full week of pent-up man juice for his new master.

“Give in to the temptation, be my slave, boy. It’s not like you have a fucking choice, anyway. I own this cock and I own your balls, and I own your fucking ass. Whose cock is this, boy?”

“It’s yours, master,” Drew said, as a wolfish grin crept over the man’s face. He remembered how the guard had said he was crazy. Was this what he meant?

“Yeah, you fucking belong to me now, you little trashy piece of meat. I’m gonna fuck the shit out of you and use you like you’ve always wanted to get used, you little faggot pervert. I read your file, I know what kind of sick fuck you are.”

It wasn’t true, Drew thought. He had tried to like girls, really he had. He had almost gone all the way that one time with Anthony’s sister. How could he be a faggot? What if it was true?

“A fucking little piece of fagmeat, and now I own your ass, and you’re gonna love it and you’re gonna serve me, boy,” his master said, the rhythmic sucking sound of the man’s huge hand on his meat growing ever stronger. Drew wasn’t sure how much longer he could hold off.

All of a sudden, the man leaned began licking Drew’s armpits. The tickling feel of his master’s day-old growth made Drew giggle at first, but the relentless torture of the man’s huge hands on his swollen cock combined to make Drew gasp. And then, the warden’s mouth was on Drew’s. The feel of the man’s sandpapery scruff on his cheek and then his lips made him wonder how he had never dared to kiss a man before. Drew resisted at first, but the warden forced his tongue all the way down Drew’s throat. The man’s scratchiness felt so abrasively masculine and his tongue so powerful and sweet that Drew felt like he was being kissed by a horse in heat instead of a man. The taste of his master’s tongue as it reached almost to his tonsils made him moan again in ecstasy. His entire body was now dripping in sweat, and he strained to breath under the weight of his master’s body upon his.

“Give me that fucking sperm sample, boy,” his master whispered after pulling his tongue from his mouth, and slowing licking the boy’s lips. “Give me what belongs to me. I have to run some tests to make sure you’re clean before I can fuck you. Because I only am gonna fuck you bareback. And if you are clean, I can start fucking you soon.”
Drew knew he was clean. Hell, he was a virgin, so how could he not be?

His master stopped masturbating Drew, and instead, spent several minutes exploring his slave’s panting, sweaty body with his tongue. He spent quite a while on the young man’s inner thigh, and then, just when Drew didn’t think he could take it any more, he felt his master’s scruffy facial hair on his erect shaft.

“Oh my God,” Drew cried, his head thrown back on the bead. The torturous pain of the scruff on his organ seemed more than he could bear. Then, suddenly, his master’s tongue was exploring the head of his cock, and licking at Drew’s pre-cum.

“Nice and sweet, saltier than most,” the warden said. “I like it. Cum is like a fine wine, and yours in excellent.”
Before Drew knew what was happening, the man was putting a black rubber ring over his cock, through which he squeezed Drew’s balls.

“What’s that?” Drew asked.

“A cock ring,” the warden said. “It will make you cum harder. Man, you really are stupid if you didn’t know that.”
Drew was about to try to say something but then his master was sucking his penis even harder now. He knew he couldn’t resist much longer.

Next, just as he was about to come, his master pulled back and stopped sucking. He went back to slowly masturbating him instead. As Drew moaned in disappointment and pleasure, his master said, “get used to that, fucker. I’m gonna tease you a lot, like the boy-toy you are. So you’d better get used to it. Oh, and here’s something else you should get used to.”

His master reached over and removed from the shelf a rubber glove, which he put on his right hand. Soon, he was applying a lubricant to the middle finger of the glove. “I want you to get a taste of what it’s gonna feel like when I DO fuck you,” his master said.

Drew’s ass exploded into pain as his master slowly forced his large finger into his anus. “God, you’re tight down there,” his master said. “This will be fun, though. I’ll start off by finger-fucking you before moving on to my actual cock.”
The penetration hurt like nothing else had ever hurt Drew. However, as the finger moved deeper and deeper, back and forth in his ass, it started to feel nice, then hot. Maybe he was a faggot after all, Drew thought, and hey, that might be a useful thing in prison. Before long, his erection was back, and he whimpered with pleasure again. He wondered if he could cum simply by having his master penetrate him this way. His master pushed deeper and deeper, and Drew moaned with pain and with pleasure. Slowly, the warden eased his finger out of Drew’s dripping, tender asshole. Drew had never felt so humiliated in his entire life. Still, he lay panting in a pool of his own sweat, his dick a throbbing seven inches once more.

“Who does that ass belong to now, boy?”

“You, master,” Drew replied, almost automatically. Before he knew it, his master’s large hands were once again toying with his balls, fondling them, caressing them. “Please let me come, sir!” Drew cried, and he surprised himself at his own intensity of desire.

“Soon, my boy. Soon,” the warden whispered. “But first, I have to tell you a secret. It’s really kind of funny, actually. Do you want to know it, boy?”

“Yes, master, anything you want, sir,” Drew replied.

“Well, it’s this. Do you remember being hypnotized yesterday during your psych eval?”

“No sir,” Drew replied. “I mean, no master.”

“That’s good. You shouldn’t, after all. Only like three percent of my patients do, you know, and it’s usually the smartest ones. Or the ones who resist the most.”

“OOOHHH,” Drew moaned again. His master was once again caressing his throbbing shaft, and he felt that he come explode at any second.

“Well, it’s a funny thing, you see. Because yesterday, we had you hypnotized toward the end of your psych evaluation. I had studied you from behind the mirror and had determined that you would be the ideal slave for me, a perfect little faggot for me to dominate mind, body, and spirit. You are the perfect candidate, are you not, boy?”

“Yes, master,” Drew said, panting and arching his back slightly.

“Well, there’s only one problem, boy. You see, once I have a perfect candidate chosen, I can dominate him in body. That’s easy. You are my prisoner, no one even cares about you, and there’s no escape. Your body, and its fluids, are essentially mine to do with as I please. Who are people going to believe, you or me?”

Drew was only half-listening. “YOU SIR, YOU MASTER!!!! He moaned.

“That’s right. And I can come to control a man’s spirit. Have you heard of Stockholm Syndrome before? No, of course you haven’t, you dropped out as soon as you turned sixteen. Basically, once you are my prisoner for a while, you identify with your captor, and you become my slave in spirit, if not totally in mind. The fact that you already called me master without thinking proves that you are already dominated in spirit. Soon, you wouldn’t be able to survive without me, and wouldn’t try to escape even if you could.”

Drew threw his head back on the bed. When would this man stroke him hard enough so he could achieve release? When would the sweet torture end?

“So, you see, my boy,” the warden continued, stroking Drew’s cock more slowly than ever, “there’s really only one problem to overcome. You see, I am a greedy man. I am used to always getting what I want. And when I see hot, desperate, horny young men, I simply have to have them. But I must have them completely. I must have them in body, in spirit, and in mind. Do you see what I am getting at?”

Drew stopped moaning and looked at the warden. “I don’t get it,” he said simply, his hard-on shrinking in his master’s hands.

“You stupid boy,” the older man said. “It’s really quite simple. I hypnotized you yesterday. I made it so that, when I make you orgasm for me, you will lose all your free will. You will become, essentially, my physical, emotional, and even mental slave.”

Drew just stared blankly at the warden. “What does that mean?”

“Well, it means that, once you cum all over the place, you have been programmed to obey me completely and do everything I tell you to do forever after that moment. You will be my total slave, and you will lose all memory of your life before.”

“But,” Drew protested. “I mean, come on. I mean, this is fun, but….:”

The man’s hand on his throat was instantaneous. “Do you want me to fucking kill you now, boy?” The man’s hand was fastened like a steel grip just under the leather belt.

‘Uh, no sir, I mean, um….”

“No, master,” Drew stammered. His heart was once again pounding, and he could feel his pulse racing against his master’s grip. He had never been so afraid. This man was truly crazy. And his cock was throbbing harder than ever in the warden’s grip. Could it be true? Could he really want this? Could he really want to be this man’s total slave on some level? Would he be like a zombie? Or was it better to be thrown to the white supremacists, or put in a padded cell like some drugged up animal?

In an instant, Drew made his decision.

“Kill me, sir, please. Kill me now.”
His heard was pounding. He was ready to die. The man could strangle him and it would all be over.
Slowly, lovingly, the warden’s grip on the young man’s throat loosened. The large, strong hand pressed against Drew’s racing heart. And then, slowly, it removed one of the clothespins, and then, the other and began to toy with his nipples. Drew’s erection was back in full force.

“No,” he said. “Please, sir, no. Please, I’ll do anything. Anything you want. I’m innocent, I didn’t do that shit they said I did, please-“

“Shut the fuck up,” the warden whispered. “Shut the fuck up. I’ve already made my decision. You’re gonna be my fucking slave whether you like it or not. In here, I always get what I want.”

“But…..I mean….”

“Shut the fuck up, I said,” the warden said and leaned across the bed to kiss Drew, who tried to shy away. “You can’t escape, boy. Just give in. Give in to your master. Give in to your fate.”

“No, no no!” Drew said. “NO! No! Let me go!”

He strained against the leather cuffs, trying to find some way to wriggle free. But there was no way out, and he knew he was doomed.

“NO!” He shouted. “Let me go, you sick fuck! Let me go! I’m not a faggot!”

“Hmmmm, your dick would indicate otherwise,” the warden said. “See how hard you are now, all ready to shoot? You’re fucking loving this, slave boy. It’s what you’ve always wanted. You know it.”

“No!” Drew tried to shout, his voice cracking. “Not like this.”

“Like how, then, boy? You and your Tony in the big house together? Please. That boy sold you out the first chance he got. You’ve been used your whole life, and now you’re gonna get used some more, just how you like it.”
“No! Let me out! Please!” He said, spitting what felt like the last of his saliva at his captor as he writhed in anger and pleasure on the bed.

“You’re making me do this the hard way,” his captor said, removing his hand from Drew’s throbbing penis. “I tried to be reasonable.”

He reached over to the shelf and took a roll of duct tape. Peeling some off, he secured a piece of it over Drew’s mouth, despite the boy’s muffled screams of protest.

“Now, you’re gonna behave for me, slave boy,” the warden snarled. “Don’t make me taser you. Now that would really get your heart pumping,” he said, laughing at his own joke.

Drew lay back, defeated on the bed. He couldn’t move, or even make a sound. And even if he could, who would come to his defense? His only hope now was that he would die of a heart attack. Maybe his master would decide to taser him. But he didn’t have the energy to fight or stain anymore. He hadn’t even eaten or hardly slept in days.
His master slowly stroked his erect penis. “Good boy,” he said. “Now, I can move on to the next phase. I’m going to play with the toy instead of breaking it,” he said.

But before Drew could wonder what this meant, the warden reached behind him and put the blindfold back over his eyes. Soon, Drew felt what felt like small suction cups and pads being attached to various parts of his body: on his chest, over his heart, on his stomach, his forehead, and at his groin. He heard his master leave and come back with what sounded like a tray on wheels, and he tried to make his penis go back to being soft by thinking of the old lady from the Titanic movie.

The sound of buttons and switches interrupted his thoughts, and he wondered what the warden could be up to now. He assumed that the warden must be about to monitor his heart rate or something, and would maybe taser him afterall. He braced himself for the pain of the upcoming shock.

But what happened next surprised Drew immensely. First, he felt the warden applying more of the slick lubricant to his cock, and stroking his shaft slowly. But this time, as soon as the young man was hard, he felt a small soft plastic tube being placed on his erect penis. Soon, this tube was suctioned to his cock and was slowly moving up and down, contracting and sucking more as it reached the head of his penis. If he could have made a sound, Drew would have once again whimpered in pleasure.

“I’ve got you hooked up to my famous milking machine,” the warden said with a wicked laugh. “It’s one of my favorite inventions. I often use it to squeeze the cum out of my studs so I can sell their jizz. But for you,” he said with a chuckle, “I’ve got it set to monitor your heart rate and keep you just on the edge of cumming. I want to extend your torture for a while before finishing you off myself. Just because you were a bad boy earlier,” he said. “And to make you learn who’s boss.”

Drew tried to struggle free from this horrible machine, but it was no use; the machine moved with him as his struggled.

“And now for the TSD,” the warden said. “Total sensory deprivation. You can’t see, or talk, anymore. That just leaves the ears.”

Drew felt his master insert a foam earplug into first one ear, then the other. Soon, the only thing he could hear were his own muffled screams.

Drew struggled against the sweet torture of the milking machine. For how long? Hours? Days? He couldn’t tell. The only break in his routine was that every once in a while, he felt a straw being inserted through a hole in the duct tape over his mouth, and he was given a bit of water, which he promptly sweated out onto the bed. He felt that he was slowly dying of dehydration. He wondered vaguely if he even had enough extra water in him to cum at all.
For a while, at first, he struggled and tried in vain one last attempt to wriggle free. Then, he actually tried to cum. At first, he wondered if he came on his own, or if he imagined that he came for the machine instead of for the warden, maybe he would be able to keep his free will for himself, just pretending for a while to be a good slave until he could escape or cry for help. Didn’t prisons get inspected? Wouldn’t he be able to cry for help someday to someone who would listen?

But his attempts to orgasm on his own were in vain. The machine he was hooked up to seemed to monitor his every move and every beat of his heart, and just as Drew felt about ready to explode, the machine would slow down and time its jacking motion so slowly that he couldn’t possibly cum, only scream silently and wish for release as tears rolled down his face.

Finally, Drew fell into what felt like an almost sleep-like state.

In his half-dream, he was at his master’s feet, begging for release, begging to be his slave. To his surprise, Drew felt no fear in this dream. He found himself actually wanting to be the warden’s slave, desired to suck his master’s beautiful cock, wanted to be the property of this powerful, hot stallion of a man. He wanted his master to own every part of him. He wanted a tattoo stating that he belonged to master on his shoulder instead of that stupid eagle.
After a while, Drew realized that the milking machine had changed its rhythm. It was pumping him faster and more forcefully, and Drew’s penis matched its rhythm, trying to reach climax. Suddenly, it dawned on Drew that it was no longer the machine at all, but his master’s large hand.

Under the tape, Drew moaned again in pleasure. The tape was ripped off of him, and he gasped.

“Oh yes, master, make me yours, please!” He cried.

One by the one, the pads and suction cups were pulled off the young stud, who moaned in ecstasy.

“Yeah….yeah…..oh yeah, give it to me,” he whispered.

“Yeah, boy? You wanna be my slave? Is that what you want?” The warden whispered, removing one of the earplugs.

“Yes, master, that’s what I want,” Drew cried. His master ripped the bandana off the young stud’s face.

“Look at me in the eyes, boy,” the warden said. “Do you want this?”

“Yes, yes, yes!” Drew cried without a moment’s hesitation.

And as he threw his head back in unbridled joy and release, Drew shot his hot, manly load all over his belly. Some of it even shot over his head and onto the wall behind him, making the warden laugh.

He had forgotten all about Anthony, his friend’s hot father, and even his dominant step-father. All he wanted now was to belong to his master, the one he’d been waiting for his entire life.

The other prisoners never learned the name of the blond boy with the vacant look and slight smile. Some thought he was just shy, but others knew better. The boy didn’t have to wear an orange jumpsuit, but rather an attractive pair of tight grey shorts and a white tank-top. He was never bothered by anyone, always got the best food, and spent long hours in the gym.


1 Comment

  1. Flamingo009 - January 5, 2019, 6:18 am

    Awesome story. Simply awesome!!!

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