Bill aka Storyguy

New Boy In Juvenile Detention

I still can't believe the judge thought I was a major drug dealer… a 'danger to the community' who needed to be locked up here in the Upstate Detention Center for Boys.

Christ! I'm only 14 years old!

It's been a month since I got sent here, and my life has gone through yet another radical change. Until last Fall, I was a shy loner who always got top grades but never really connected with other kids. And when my family moved to a new town in August, I didn't know a single student when I entered the freshman class at the local high school. And it certainly didn't help that I look so much younger than my age. I mean, sometimes I got mistaken for 11 or 12 years old!

At first I didn't think I'd make any friends at all at my new school, but one of the 'stoner' kids went out of his way to be nice to me. That's how I fell in with the pot-smoking kids at school. I'd never smoked weed before, but when I started getting high I felt much more confident. It seemed like I was finally fitting in at school.

Sitting here in Juvy (that's what everyone here calls the Detention Center), I sometimes wonder whether they were just taking advantage of me, using me to make the purchases and sales of weed. I had a lot of money saved up from birthdays and allowance and stuff, and all the buys were from this one guy who seemed totally cool and honest. I'd buy an ounce or two of primo grass, and then my friends would buy dime bags from me. I didn't even make much of a profit… practically sold the stuff at cost. It was so easy that before long I was buying larger amounts and selling to kids I didn't even know.

Even though people started being friendly to me, I was always really shy around girls. Some of my friends bragged about doing sex stuff with girls, but I couldn't bring myself to ask a girl on a date. Besides, even if I had a chance to have sex with a girl, I'd be way too embarrassed for her to see the small size of my cock, and the lack of any hair down there. (Christ! I didn't even know how to jack off until I got here in Juvy last month!) I wasn't completely naive… I'd seen some Penthouse magazines that one of the guys at school had, showing pussies and blow-jobs and fucking and stuff, but I couldn't seriously imagine doing anything like that. And just so you know, I'd never done anything with another boy either, and I'm almost positive that none of my high school friends did any queer stuff.

The last time I made a buy… the time I got busted… I bought a half pound. I was arrested right after I traded a fat wad of $20 bills for the weed. It was like a bad dream… them putting handcuffs on my wrists, taking me to the station… having to call my parents. There was even a newspaper article the next day about a 'high school drug ring' being broken up by the cops. Thank God they don't use the names of arrested juveniles in the paper.

Dad got me a lawyer right away, and I got bailed out after the police tried to interrogate me. (The lawyer told me not to say anything.) We were all confident that I'd walk, getting probation or something. The lawyer said that was the usual thing if you'd never been in trouble before, did well in school, and came from a good family. None of us expected the judge to send me to jail… 18 months in a juvenile detention facility! But that's how it came down. The judge gave me a long lecture about how evil I was because I sold dope to school kids. And right after the trial, the police took me away. I barely had time to say good-bye to Mom and Dad before I was in a sheriff's car for the long drive to Juvy.

The first thing that happened when I got there was that I was led by a guard to the intake room where there was a step-stool in the middle of the small room and a table with a pile of clothing, towels, and bedding.

"Take off all your clothes and put them in that big plastic bag," said the guard… a middle-aged black guy. "You'll get them back when you're released. Until then, you'll wear standard-issue clothes." He pointed to the pile on the counter.

I slowly took off my shoes, socks, shirt, and pants. I stalled when I was down to my boxers. I was embarrassed about how immature I looked down there.

"Come on, boy. I said ALL your clothes. Now MOVE IT!"

I turned my back to him as I pulled off my shorts, and then shielded my under-sized penis and balls with my hands.

"Now stand on that stool, and put your hands up atop your head," he ordered. "I need to do a full body search." He was slipping rubber gloves onto his hands.

I got on the step-stool, but my hands still cupped my crotch.

"I said HANDS ON TOP YOUR HEAD," he barked angrily.

I hastily complied, feeling my face glow red as he stood in front of me and began feeling me up, carefully examining my penis and balls with his gloved fingers.

"Need to make sure you ain't got nothin' taped to your privates. You'd be amazed how often boys try to sneak contraband in here… pills, razor blades…" Then he looked in my eyes and leered. "You kinda sensitive, ain't you, boy?"

I glanced down and saw that my penis was standing up totally rigid… a slender boner that measured just under of 4 inches [10 cm].

"If you liked that so much, boy, you gonna LOVE this next part." He was squeezing some clear gel stuff onto his middle finger. "Bend your knees a bit and grab hold of your ankles."

I felt his hand spread my cheeks, and then… Yow! I almost fell off the platform as his finger slid all the way up my asshole and twisted around inside me, probing the walls of my rectum. Even though it felt REALLY strange, it made my boner throb like I'd never felt it do before.

"You're clean. Now get dressed in those Juvy clothes and follow me to your barracks. I gotta tell you… you gonna make LOTS of friends around here, boy," he said. In my flustered condition, I didn't even realize he was being sarcastic. I thought he was trying to comfort me!

There were two complete sets of clothing… khaki pants, blue button-down shirt, white jockey briefs (which I hadn't worn since I was, like, 8 years old), white socks, and blue canvass sneakers without laces… pull-ons, almost like slippers.

After dressing, I was led down a long corridor with locked doors labeled 'Barracks A', 'Barracks B', etc. Each door had a small window through which a guard could check the inmates As I went through the door of Barracks F, everyone inside turned to stare at me.

"Listen up, you clowns," said the guard. who accompanied me. This here's Billy Worthington. Make him feel at home." And then he left. The key turned in the lock of the door, and there I was… alone with group of ACTUAL CRIMINALS.

As I looked around the room, I saw that it was both a dormitory with rows of beds, and a lounging area with chairs, two sofas, and a TV set. One of the bunks had a bare mattress, with nothing on the small shelf on the wall above it. That would be my bed, I figured. There were 13 other boys… some black, some white, some hispanic. Although they ranged in age from 13 to 17, they all seemed so much older than me, even though a few were actually younger. And they definitely looked stronger and meaner. Each of them had an expression of sneering hostility… projecting a tough "street" attitude. My suburban preppy lifestyle was about as foreign in here as if I were in some third-world country.

The only one to get up to greet me was an older white kid. A big guy, who looked like some of the football linemen at my high school… 6 feet [1.80 m] tall and very muscular.

"Welcome to the crew, Billy. My name's Jake," he said, with a pleasant smile. But he also was looking into my eyes with an intensity that seemed to probe my brain. "Let me help you with that," he said as he took the bedding and clothes that I held and tucked the bundle under one of this strong arms.

"You might say I'm the leader in here, so I figured I should help you get adjusted. Here… have Snickers bar," he said, pulling the candy from his shirt pocket. "You look hungry."

"Thanks, Jake!" I said, my pre-adolescent voice cracking (to my embarrassment). I WAS hungry. It was late-afternoon, and I hadn't eaten since breakfast. I wolfed down the Snickers as I listened to Jake naming all the boys in the room as he pointed them out… Pete, Juan, Tony, LaMarr, Styx, Maurice….

Then his voice lowered to a near-whisper. "Let me tell you something, Billy. Juvy isn't a safe place for a kid your size… especially a young white kid who ain't street-wise. What you need is someone to look out for you and be your protector. How 'bout if I be your protector 'til you get settled in? OK? We can be buddies, and I won't let any of the guys mess with you."

I looked around at all the dangerous-looking boys in the room, and then up at Jake's smiling face… and then at his powerful chest and arms. Nobody was going to cross him. I felt relieved that I'd found a friend like him so quickly. "Sure Jake. I'd like that a lot!" I said.

"Excellent!" he said. He wrapped his big arm around my shoulder and led me back to his cot, putting my stuff on his bed. Then he spoke to the young hispanic boy sitting on the bed next to his. "Paco… get your stuff together and move to the empty bunk. This is gonna be Billy's bunk now. Come on; hurry it up."

"But Jake… I thought we was…" said the slender weasel-faced kid in a high-pitched whiney voice. Then he looked at the expression on Jake's face and immediately shut up. He pulled his sheets and blanket off the bed and gathered the rest of his stuff together quickly. I didn't know what to say…. I certainly didn't want to kick someone out of his own bed. But I set about making up the bed, like Jake instructed.

Jake must have noticed my uneasiness. "Don't worry, Billy. I've been Paco's protector for two months now, but he'll find another. In fact… look over there. I think he's found a man already." On the other side of the room, a husky black youth was running his fingers gently through Paco's shoulder-length black hair as they spoke softly. And the young hispanic boy was acting just like a flirtatious girl!

"Paco was a good pussy-boy, but he sure wasn't much to look at," continued Jake. "But you… you're downright pretty." His eyes scanned up and down my body, and he added "So, Billy Boy… you ever been fucked by a guy before?"

I sat there stunned as my brain tried to comprehend all that I was hearing and seeing. All I could do was shake my head 'no'.

"You ever give a blow-job?"

Again my head wagged quickly from side to side as my heart pounded in my chest.

"A virgin, huh? Excellent! Tell you what… how 'bout you strip down and let me see what my new bitch looks like naked."

I couldn't breathe. I felt paralyzed by panic. Finally I croaked out: "Uh… Jake…. You don't understand… I'm not… I didn't…."

"Like hell you didn't," he roared. His smile had been replaced by a glare of half-crazed anger. "You signed on as my pussy-boy just as sure as if you signed a contract. Ain't that right boys?" All around the room were murmurs of agreement, and heads bobbed in affirmation. "So stop bullshitting me and strip nude. I own your ass now, so let me see what I'll be fucking tonight."

I looked around the room for support, but saw that there would be none. In panic, I started calling out for help, hoping a guard would come save me. I only got out a few syllables before Jake's hand clamped over my mouth and his other arm held me from behind with a vicelike grip around my chest. Then, in a quick movement, he stuffed a sock into my mouth before I could call out again.

"You blew it, boy. If you'd just submitted to being my bitch, I would have kept all the other guys away from you. Now it looks like I'll have to share you with my buddies to get you broke in." Jeff snapped his fingers like an customer summoning the waiter at a fancy restaurant . "Rocky… Carlos… Stony… DeWan… take his clothes off and hold him down."

Four older teenagers pounced on me in a flash, as the rest of the boys swarmed around for the show. They lifted my whole body up off the ground… two at my legs, removing my socks and shoes, and pulling off my khakis and underpants. Two more held my arms and unbuttoned my shirt, working it off my arms. Then they set me down on the bed, on my back, spread-eagled and arms pulled to the sides. The sock was still stuffed in my mouth, and my muffled shouts of protest were inaudible. I was helpless and soon stopped struggling, resigned to the embarrassment of my nudity being so blatantly displayed.

"Oh yeah! Nice!" said Jake, running his hands all over my slender hairless body. As he fondled my little penis and balls, I was horrified to see my boner rising up in response.

"Sweet!!" he exclaimed. "A little-boy cock… same size as Paco's… and a cut one for a change. And not a single pube hair. Perfect!"

Paco spoke up indignantly from the crowd. "Hey Jake…. I got BIGGER cock that him. I not the smallest in the barracks no more."

"Hmmm… why don't we just compare," said Jake in reply. "Pull down your pants and lie on top of him… hold your dick next to his so we can see."

"OK, Jake!" chirped the young hispanic kid joyfully, as he unzipped his khakis and pulled them completely off. As he did, I saw that he was wearing girl's panties… skimpy pink bikinis that clung to his boyish genitals and slender round ass, with a lacy trim around the waist. When the panties slid down his thighs, I saw his small, uncut penis, with a very few strands of black pubic hair. His fingers went to work on his soft dick, sliding the foreskin back and forth and causing it to rise to an erection that was similar to my own. Then he mounted me, lying between my spread legs, brought his crotch to mine, and humped our two boners together… almost like he was fucking me! His hands moved over my chest and shoulders seductively. Bringing his mouth to my ear, he whispered "You a sexy one, gringo. You gonna be a hot bitch 'round here… just like me. Maybe Jake he want us to do a three-way sometime, eh?" Then he lifted himself off my chest so everyone could see our erections together, shaft against shaft.

"Wha'chu think, amigos? I got bigger cock than the new muchacho, eh?" he said, addressing the question to the whole room.

"Yeah; I believe you do, Paco," said Jake with a chuckle. "Now you're only the second-smallest. Tell you what… how about I let you into Little Billy's blow-job line? You can even be first, as a reward for being such a good bitch for me over the last two months. It'll be you, then me, then Stony, Carlos, Rocky, and DeWan. The rest of you guys can have him too if he doesn't do a good enough job and needs some more practice. Oh, and Paco… take off those panties and leave them for Billy-Boy. He'll be wearing them now. I had them smuggled in, so they go to whoever's my pussy-boy."

My eyes widened in shock and disbelief… at again hearing myself called a pussy-boy… at the idea that I'd be wearing girl's panties. And, especially, that I'd have to give blow jobs to six of these boys… and maybe all thirteen! I hardly even knew what was involved in a blow-job, but I definitely knew that only a slutty girl or faggot boy would do it willingly.

I weighed the options and decided it would be better to resist than submit. Maybe they'd respect me for that and leave me alone. As soon as the sock was pulled from my mouth, I began to shout and thrash around again.

"Billy, Billy, Billy," sighed Jake, after he quickly stuck the gag back in my mouth. "Why are you making this more difficult than it needs to be?" He picked up one of my light-weight sneakers, slapping its sole into his other hand, and said "I guess it's time for a spanking. Get him in position, guys."

In an instant, my legs were pulled back over my head and my body was bent in half, held securely by four pairs of strong arms. Jake's hand caressed my up-raised butt for a few moments, and his finger stroked along my totally exposed anus. And then he stood back and began administering a steady series of swats with the sole of my own shoe… slamming it into my tender buttocks with an incredibly painful impact. Without the sock in my mouth, I would have been screaming and crying at maximum volume. And then I would have been begging my tormenter to stop and promising total submission. But my muffled pleas were totally drowned in the sound of the other boys laughing and joking. My tears, however, were dripping steadily down the sides of my face… evidence of the agony radiating from the red-hot flesh of my butt.

After about 25 wicked swats, Jake paused and said "Are you ready to do what you're told, bitch?"

I nodded my head vigorously, making urgent grunting noises of agreement.

"When I take this sock out, I better not hear any more shouting for the guard, or you'll get 50 more wacks. You're gonna do whatever I tell you. In fact, you're gonna be my obedient little slave-boy slut from now on… understand?"

Again I wordlessly signaled my surrender. And when the sock was removed and my limbs released, I was blubbering like the pathetic little wimp that I was. "Please! I'll do anything you want! Just don't spank me anymore!" My voice was choking and tears continued to stream down my face.

"That's what I like to hear, bitch. And since you're my little slave-boy, I want you to start calling me 'master' from now on. Understand?"

"Yes… m-master," I murmured, feeling total humiliation and helpless submission.

"Good. Time for you to learn how to suck cock. And you'll learn it in a hurry… right?"

I nodded to show my understanding, but Jake's hand raised up and delivered a hard spank to my ass. "Say it, slave. You gonna learn real quick to be a good cocksucker?"

"Yes, master," I quickly blubbered out. "I'll be really good, master. I promise!"

"OK; let's get going. Hey DeWan; stand by the door and give a yell if a guard's coming. Billy-Boy, you put those panties on and get on your knees on the floor. Paco, you're first; feed him your cock." The young hispanic kid was grinning like an imp.

Jake was the leader of this group alright. He was orchestrating the whole thing. I stood up from my bunk, totally nude and painfully aware of the heat radiating from my ass. As I pulled the slinky nylon panties on, several of the boys gave lusty whistles of approval, and I blushed with embarrassment. I sank to my knees, and Paco moved in close to stand above me.

"After all the blowjobs I give here in Juvy," said the young Puerto Rican, "this the first time I get my own cock sucked by a Juvy boy." Then he giggled. "But back home in the city I sometimes get blowjobs from the anglo men who cruise the park in their expensive cars, paying $10 to suck a little boy's pinga. Maybe you papa he give me blowjob one time, eh chico?"

I didn't say a word, trying to avoid the mental image of my conservative, dignified father on his knees sucking a boy's cock. But that's exactly the position I was about to be in. Paco was still nude from the waist down, and I stared at his slender, tan 4-inch [10 cm] boner, inches from my face. My hand reached up to cradle the soft pouch that held his hairless ball-sack, then moved to his rigid boy-cock and aimed it forward. I took a deep breath, knowing I had no choice, and opened my mouth. The throbbing little erection slid between my lips, and I let my tongue slide over the partially exposed glans and the warm smooth shaft. To my surprise, it wasn't so bad! As my lips began to move along the finger of warm cock-flesh, Paco started moving his hips.

All of a sudden, Paco pulled my hair back, causing his cock to pop out of my mouth, and I looked up at him in shock. "Don't let you teeth scrape me, you estupido puto [stupid faggot]. Keep you lips pulled back around you teeth. And use you tongue more while you sucking. Madre-de-dios! Do I gotta teach you everything 'bout cocksucking, gringo?"

He gave me a few more instructions as I tried my best to do it right, remembering Jake's threat to make me suck every boy in the barracks if I didn't perform well enough. Paco's erect penis was small enough that I could effortlessly take all of it into my mouth. My hands wrapped around the soft little globes of Paco's ass as his moving hips and my sucking mouth merged in a smooth rhythm. The approving comments of the boys who stood around watching, and the pleasure noises Paco was making, assured me that I was doing a pretty good job. And my fear and humiliation were gradually being transformed into a curious pride. Incredibly, I was finding the experience arousing, and my own penis was stiffening inside the smooth panties I wore.

The rhythm of sucking and the movements of my lips and tongue seemed completely natural… like something I already knew how to do, even though I'd never had a penis in my mouth before. And the scent of Paco's nearly hairless crotch – the soap smell of his morning shower mixed with an intriguing youthful musk -- was an aphrodisiac to my senses.

When the boy's hips started thrusting faster, and the muscles in his butt tensed beneath my fingers, I held my mouth still and let Paco fuck my face. His breathy vocalizations in Spanish were incomprehensible to me, but I could tell he liked it… a lot! Then his little boner was spasming against my lapping tongue, and he was squealing with delight. I held my lips down at the base of his throbbing cock, sucking his rod like a baby sucking his thumb. I had no idea what an orgasm was (much less a dry orgasm), but I knew that Paco was in the throes of extreme pleasure, and that exited me too. My own stiff penis pressed urgently against the tight, silky panties and my fingers rubbed against it.

At last, Paco backed away from me, a big smile on his face.

"Muy bien, Billy!" he chirped. "You can suck me anytime… OK?"

I didn't have time to exchange pleasantries with Paco, though, because there was a line of boys waiting for the services of my mouth, the order having been determined by Jake. And the next in line was Jake himself, unzipping his trousers and letting them drop. The front of his white briefs bulged as my fingers went to the waistband and slid them down his thighs.

"Work on this for a while, slave-boy" said the muscular youth, fingering his half-hard dick and slapping it across my face a couple of times. "You're gonna get VERY familiar with it."

To my naive eyes, his dick was enormous… almost 7 inches [18 cm] and thick… sticking straight out. His dangling balls were full, and a mat of dark pubic hair gave further evidence of his manliness.

"Blow me, cocksucker."

"Yes, master," I murmured, as I took the shaft of his circumcised penis in my hand and brought my mouth down onto it, sliding my lips around the prominent head. As my tongue slathered around the piss-slit, and then all over the glans, the cock pulsed to full erection in my mouth. It didn't get much longer, but it seemed to get thicker… the helmet on top even more prominent. I needed to stretch my mouth wide to take its width, being careful to cover my teeth.

Jake's hand caressed my hair as my mouth started to move up and down, and his voice was gentle as he vocalized his satisfaction. As I worked, his fingers entwined through my hair, setting the pace of my mouth's movement along the thick shaft. And as I tried hard to please him, I felt like I was totally under his control. The pressure of his hands and the thrusting of his hips instructed me, and it was clear from the beginning that I was supposed to take his cock deeper… take it all the way into my throat. I couldn't do it at first, gagging as his fat cock-head pushed at the entrance of my throat. He would back off for a few seconds, but then he'd be back… insistent that I try again.

Through sheer force of will, I succeeded in conquering my gag reflex. And once accomplished, I was able to do it again and again… gliding along the full length of his pole, swallowing it into my throat, and pressing my lips and nose into the forest of pubic hair. It certainly wasn't comfortable, but I was succeeding and felt a sense of excited pride.

"Yeah! That's it, bitch… take that cock! Ahhh… shit… that's good! Now squeeze my balls…. Yeah; just like that."

Jake's hips began to thrust powerfully into my face as his hands clamped down on my head. It should have been a frightening and humiliating experience, but instead I was thrilled. Sucking cock had unlocked a part of my senses that I didn't even know existed, exhilarating me completely. My own stiff little boner throbbed with pleasure, and I rubbed it through my panties with one hand while my other hand massaged Jake's full balls.

"Uhhh!… Keep going, bitch… I'm gettin' close!" Jake grunted. Recalling Paco's build-up to orgasm, I could tell that Jake's pleasure was peaking. And sure enough, after a few more quick thrusts, he kept his cock deep in my throat as it exploded. Unlike Paco's pre-adolescent dry orgasm, however, Jake's fat boner unleashed a torrent of hot cum… directly into gullet. I was swallowing time after time as my throat muscles clenched around the shaft, and spurts of fluid kept spraying out.

When Jake – my master… my owner – finally released my head and withdrew his cock, I gasped for breath and swallowed some more.

"You did OK, punk…. I'm gonna take good care of you as long as you keep doing what I like." He looked down at me with a friendly grin on his face, and I looked back up at him with a smile of my own. "But first, you need to do the rest of my guys…. Stony; you're up next."

The lanky white teenager leered at me as he came over, pulling open his pants and masturbating himself as he walked, getting fully hard in a few quick strokes.

"Suck it, kid," he said as he thrust his boner toward my mouth.

My jaw and throat were sore from servicing Jake, but I knew what I had to do. And there were three more in line after Stony. I slurped his 6-inch [15 cm] cock into my mouth and began to pleasure him with a determination to make him cum quickly. Glancing to the side, I saw Jake sitting on his bunk, watching attentively, a look of approval on his face.

I was totally exhausted by the time I finished my sixth blow-job, swallowing the last spurt of cum from DeWan's musky, uncut 7-inch [18 cm] cock. DeWan was the big black teenager who was now Paco's "protector". Rising unsteadily from my knees, I threw on my clothes, lay down on my bunk, and closed my eyes. The next thing I knew, Jake was nudging me awake and saying it was time for dinner.

For the next few hours, I hovered around Jake like an obedient dog, trying my best to avoid doing anything that would get him mad at me. And he seemed pleased with me, draping his arm over my shoulder as we walked down the corridor to the dining hall, caressing my thigh as we sat together at dinner and bringing my hand to his crotch to stroke him as he ate.

Later that evening, as Jake and some other boys were busy playing cards, Paco took me aside and asked if I wanted some advice about how to keep Jake happy. I gratefully accepted his offer and let him lead me to the empty shower room where we could talk privately. He gave me a nutshell description of how to be a first-class prison bitch… what a dominant stud like Jake wanted… and how to deal with getting fucked in my ass by a big cock. He even gave me a little jar of vaseline and told me how to prepare myself.

Around 9:55 a guard came by the barracks to do a head-count, 5 minutes before lights-out. After the guard left, I was amazed to watch all of the boys pair up for the night… every single one of them. It was clear that the usual teenage taboo about queer sex didn't apply here in Juvy. All around the room, teenage boys were stripping naked. I was to learn quickly that the four biggest boys each had a regular partner – a bitch – from among the smallest kids like me and Paco. The other six guys in Barracks F paired off with each other more or less as equals. Some pairs were just sitting on a bed waiting for the lights to dim before starting their sexual encounter, but others (the older/younger pairings) were already engaging in sexual preliminaries.

As for me and Jake, I was ordered to strip down to my panties and stand beside my bed. Jake stripped naked and stood behind me, running his hands over my chest, belly, crotch, and thighs as his stiffening cock pressed against my ass. His fingers slipped under the waistband of the panties and slowly lowered them down my hips, allowing my erection to spring back against my belly. I could see faces around the room starring at me, but I didn't dare to resist Jake's actions.

Then the lights went out, activated at some central location for the entire facility, and the room was plunged into darkness. As my eyes adjusted, I noticed it wasn't pitch black, and I could see the shapes moving on the other beds as the sexual activity began to intensify.

"Suck me, slave," Jake whispered in my ear. "Get my cock nice and slippery before I fuck you."

"Yes, master," I replied, as I turned around and sank to my knees before him. My mouth sought his cock and enveloped it. My heart was pounding, anxious about what was coming next. All around the room the sounds of boy-sex were beginning… slurping sounds that may have been blow-jobs or kissing, squeaking bed frames, grunts, and low moans and sighs. Paco's words of advice ran through my head, and I hoped to God he was right about how it would be.

With Jake's penis at full erection and well-coated with my saliva, he pulled my head away and hissed "On the bed, bitch; on your hands and knees."

I positioned myself on my bunk, head down and ass up, resting on my elbows, my knees splayed. I could see Jake's outline standing beside me, his man-size cock standing straight up… and I could smell his masculine scent. I felt his hand running along my back, sliding across to my skinny little-boy butt. And then his fingers went to my hole.

"Mmmm… your cunt is already lubed! That's smart of you," he murmured. And then, without another word, he positioned himself at my upraised ass, eager to mount me. I thought about dogs I'd seen mating… how the male was driven by lust and the female submitted passively. I was Jake's "bitch". The metaphor was perfect.

I had just remembered what Paco had said about flexing open my ass when I felt Jake's ramrod being positioned at the entrance of my body… and then pushing forward into me.

Arghhhh!! The pain was awful, stabbing, burning. I bit down on the bed-covers as hard as I could and desperately tried to keep my anal muscle dilated as the thick phallus was forced into my virgin pussy. Everything faded from my consciousness except the intense discomfort of my ass being violated.

"That's it bitch," said a soft, deep voice in my ear. "I'm all the way in; you're doing good."

My mind cleared and I realized he was right! The forward motion of his cock had stopped. I was totally filled by his hot thickness, but the initial blinding pain was starting to subside. Jake's arms wrapped around my body, and he began to hump into me, sliding his cock back and forth inside my vaseline-lubed hole. I was still biting down on the covers, as Paco had suggested, but the burning was slowly moderating into a warm sensation that was almost tolerable.

I tried to occupy my mind with other thoughts as Jake got into a fuck-rhythm behind me. My brain settled on a scene I remembered from a Penthouse magazine… a beautiful slutty naked woman with a wanton look on her face, being fucked from behind by a macho cowboy. They were in a barn, and she was face-down on a bale of hay. The woman's facial expression had broadcast how wonderfully pleasurable it was to be fucked. And strangely, as I imagined myself being that slut, pretending to enjoy the deep cock-thrusts into my "pussy", the pain ebbed away.

I realized my penis was stiff again, and as I raised my ass up to receive Jake's thrusts, his fingers reached down to fondle my erection. My stretched anus now felt a numb pulsing sensation as other sensations began coursing through my body… feelings that were quite the opposite of pain. Every time Jake's thick cock glided across a certain place inside me, it set off bursts of electricity. Jake's hot breath on my neck, the sound of his panting exertion in my ear, and the feel of his naked sweating skin sliding against my back all combined to increase my excitement.

And the feelings building up in my loins were totally new to me. I had never learned to masturbate, so the throbbing pressure inside of me was quite unlike anything I had ever experienced. As Jake began to moan with pleasure and thrust with increasing passion, I found myself automatically vocalizing as well.

"Fuck me! Yes… do it!" I murmured.

I lost all awareness of where I was… of the other boys around me… of the trial I had gone through that morning. My entire consciousness was focused on the hot cock sliding inside my body, and the strangely wonderful pressure in my cock that felt like it was going to explode.

And explode it did, amid a shower of explosions behind my closed eyelids, a rush of electric jolts racing throughout my body, and a powerful euphoria that flooded my brain. The sensations coming from my penis, which Jake's hand was now stroking vigorously, were unreal in their intensity. And as my anus spasmed around Jake's driving cock, I felt like I never wanted it to end. I wanted him to fuck me forever. But in just a few more seconds he exploded as well, spewing hot cum into my core, shivers running thorough his body as he thrust into me a few more times.

Jake rolled us over onto our sides, his cock still buried in me. My ass clenched and unclenched around his cock, which throbbed in reply. And when Jake's hand released my cock I realized it was wet and sticky… bearing the fruit of my first orgasm. His fingers came up to my mouth.

"Lick it off," he commanded.

"Yes, master," I replied obediently.

My tongue lapped against his hand, and I tasted my own semen… mild, sweet, and salty. I sucked on each of Jake's fingers as he continued to spoon against my back. Finally, his softening cock slipped out of me and he pulled his hand away from my mouth.

"You did alright, Billy-Boy. I made a good decision in switching from Paco to you." He turned me around to face him and wrapped his arms around me in an embrace. "I think we're gonna get along just fine."

I didn't know what to say or do. And then, through some impulse that bypassed my consciousness, my lips came to his mouth. I kissed him, even though I had never before kissed any other person on the lips. And he returned the kiss, his lips parting and his tongue sliding against my mouth. Going entirely on instinct, I extended my own tongue, and our bodies clung together desperately as we began to make out.

Later, after Jake had returned to his own bunk to sleep, I tried to sort out my thoughts about the events of the day… the most eventful day of my life, by far. Was I scared? Damn right I was! Was I homesick? Of course! But my mind and body kept floating back to the magic of discovered sexuality… and the thrill I got from being fucked by the toughest convict in the barracks. I knew then and there that my destiny was set. And now, a month later, I've become a living stereotype: the sissy jailhouse bitch. But Jake protects me, and nobody wants to cross him. And he wants me to act girlish and swishy, so I do everything to keep him happy. Who knows what I'll be like when I finally get out of here!

The End