Turning Out Pretty Boy - chapter seven - Friday Night's All Right for Fucking
* This story is fiction. Any resemblance to actual events or living persons is coincidental.
Personal experiences – images, events, memories, and words – flavor my writing, and while elements of this story may be (and often are) based on facts, the characters are entirely fictional.
* Unprotected sex is depicted. In real life, be safe! Don't gamble.
* If it is illegal for you to read this story because of your age, location, or any other reason, don't read it.
* This work is copyright by the author. Commercial use without permission is prohibited. Please do not republish any part of this story without consent of the author.
- Please consider a contribution to Nifty to keep this forum healthy. Look for the `donate' button on the home page. http://donate.nifty.org/donate.html
Author's Note: I appreciate feedback, from story suggestions to comments. Hearing from readers is the main reason I post on Nifty. It may take me a while, but I try to respond to all. Email: ColtonAalto@gmail.com.
Special kudos to one of my readers, mike, for his help with the prison life depicted in the story. Thanks much!
TURNING OUT PRETTY BOY
BY COLTON AALTO
CHAPTER SEVEN – FRIDAY NIGHT'S ALL RIGHT FOR FUCKING
From my first day in gen pop, I was Jaxx's bitch boi. My embarrassing introduction to the inmate population – when he grabbed my ass in the dining room and I meekly volunteered that he owned it – left no doubt in anyone's mind, guards, or inmates. That role defined me during my entire time inside. The inmates knew me only as Sunshine, the pretty boy with the long blond hair and teen-model looks who was a possession of the Black God.
Jaxx didn't want me befriending other inmates, and they were afraid to talk with me anyway for fear he'd accuse them of moving in on his property. That rule didn't apply to the other prison wives and jail bitches who took it up the ass – Ramon, Aidan, and the others I'd met the first night. They weren't a threat to Jaxx for the simple reason that they were at the bottom of the prison pecking order, above only sex offenders. They were my social circle and we hung out and ate meals together.
I got to know several of them pretty well. Jarret was a skinny white kid with curly red hair who was a prison bitch like Ramon was, but if you saw him or talked to him, you'd never think he was queer. In the prison he and Ramon played the opposite roles. Dudes who liked Ramon's queeny, campy act fucked him, while dudes who wanted to bone a masculine-acting guy fucked Jarret. He was matter of fact about his situation, just saying that he liked having sex with guys and it was a helluva lot better than beating off or getting beat up. He liked me and it quickly became apparent that he sorta had a crush on me. He reminded me of some of the kids I'd fucked before I got sent away; in fact, if I'd met him on the outside I would have made it a point to get into his pants. Ironically, that wasn't an option now. As much as Jarret might want to get it on, that wasn't going to happen while I was owned by Jaxx.
Another prison wife, Steven, was a light skinned Black kid who was attractive and got labelled a pretty boy almost as much as I did. He claimed to be straight – I was pretty sure he was – but he was resigned to being gay for the stay and stoic about surrendering his ass in the joint, counting down the days until he got out. For whatever reason one of the Black Godz had decided Steven would be his bitch boi and that was that. At first I felt sorry for him because he was straight, but it soon became apparent that his Black God treated him better than any of the other wives. The scuttlebutt was that the God picked him because they were half-brothers and he'd been using Steven's ass for years before they got jailed. Steven admitted as much to me one night, saying matter-of-factly that incest ran in his family. When I questioned him, he rolled his eyes and said, "It runs deep and wide. I gotta lotta older half-brothers and cousins, and once one of my half-brothers broke me when I was like 12 and the word got out that I wouldn't tell, they figured my ass was the solution to every bone they got. I grew up thinking that every kid with older brothers was expected to surrender his ass whenever and wherever. I was like 16 before I figured out that it didn't work that way in other families."
The Asian twins were strange. They were quiet and meek mannered, and I had a hard time seeing them doing anything that would have landed them in the prison. However, there were rumors of a ritual murder, perhaps even during a sex act. A single Black God owned both of them and apparently only used them together. Four holes for one cock seemed overkill, but I guess the dude liked the attention of two boys at the same time. He was into kink and they apparently weren't bothered by incest.
I got a lesson about mingling with the other inmates not long after I was put in gen pop. I went into a room where guys watched TV and quietly found a chair toward the back. One of the other inmates glared at me and nudged his buddy in the side. Looking directly at me, he said to his friend, "You smell somethin? Stinks in here alla sudden. Smells like a fucking cum bucket." His friend nodded and said, "Yeah, better make sure nobody sits in that chair. Cum is probably leaking out of the faggot's fuck chute." They got up and left, staring angrily at me, and I felt my face flush. A couple of other dudes gave me dirty looks and soon I slipped out, knowing better than to try again.
Prison was tedious, but tolerable, as I spent my time reading and studying – something I never did much in school – working out and killing time in my job in the prison infirmary. Of course during a good chunk of that time my holes were filled with a dick. At first it was only Jaxx's big black cock, but over time that changed, starting with the first Friday night I spent in gen pop.
Aidan and I and the other outcasts were waiting for the rest of the inmates to clear out of the dining room when he slipped his hand onto my thigh and whispered, "It's time Sunshine. Jaxx and Jamar have the basketball court every Friday night, and I'm stupid horny to get into your tight ass." He put an exclamation point on his comment by guiding my hand to his crotch. He was boned already. I briefly worried whether Jaxx would be okay me giving it up to him, but Aidan claimed he had permission and the dude was prison savvy enough not to do anything stupid.
He leaned close to me and whispered, "First time I saw you, face down and ass up on the floor of the cell, I knew instantly why Jaxx picked you. When he told me about you, I was skeptical, but when I saw that pretty face, long blond hair, and bubble butt, I knew he was on to something. At the very beginning I didn't think you'd be easy to turn out. But you are one hot piece of ass."
"Actually, I was scoping out your pale ass pretty hard the first couple of days."
"Yeah, well as you know, that's off limits. But unless I'm badly mistaken, you spent even more time perving on my dick. That's when I began to think it might not be as hard to turn you out as I thought. But I never in a million years imagined Jaxx would nail you before you were even in gen pop. I hope your ass ain't too sore from getting boned by the stud."
I was adjusting to it.
Aidan knew a place we could use, in the small library near the school classrooms where he worked. As we walked there, he said, "Damn did I ever want to shove it up your ass when we were in the holding tank. I've had fucking blue balls ever since. I haven't gotten a load out since I fucked Jennifer the night before they picked me up."
"Only Jennifer?"
He laughed. "Hell, no. Jensen was waiting for me in the hallway after I left her room. He'd listened while I dicked her and stroked his hard on the whole time. Dude was pre-cumming so much that I thought he'd already shot his wad. He pulled my cock out and went down on me right in the hallway. Shit, if she'd gotten up to go to the restroom she'd have seen us, and as it was I was surprised she didn't hear us. If she'd found me face fucking her brother, I dunno who she would have been madder at. He sucked me off right there. I guess he didn't mind tasting his sister's cunt juice. The dude always was a better cocksucker than she was and she won't swallow, either.
"He knew that after I spermed his mouth I was gonna fuck his twat. Once I get started I don't wanna stop. His parents were gone and he said he'd always wanted to get fucked in their bed. Weird but whatever. He licked every inch of my body and got me hard again, and then sat on my cock. He was wearing a butt plug to open up his ass, and he just pulled it out and guided my cock into his hole instead. I let him ride me the first time and then I did him once doggy style and once on his back. Fucker shot on his face the last time and slurped it all down. If I'd known I was gonna be thrown in jail the next day, I'd have juiced his butt a couple more times."
The library was occupied by a handful of inmates, but Aidan guided me into a storage room in the back, filled with books. The place oddly reminded me of the cell we'd shared in intake, and that memory became more real when he pulled off his shirt, revealing the same farmer's tan, freckled shoulders, fleshy pecs, and hard abs I remembered. As he looked at me like a hungry wolf, I suddenly knew what I wanted.
"Back in intake when I threatened to give you a black eye. Do you remember what you said? You said, `You're damn lucky that I'm straight and don't like shoving my cock into other guys' shitters, because otherwise I'd have already turned you into a sniveling pussy.'"
He laughed. "Okay, you got me. I like shoving my cock into guys' shitters."
"Do what you wanted to do then but didn't `cuz you were worried about Jaxx. The part about turning me into a sniveling pussy."
"Fuck, dude, that was a couple of nights after I'd boned Jennifer once and Jensen three times and I was still hornier than hell. You were a little shit, your ass was fricking awesome, and I wanted to fuck it until you were crying your eyes out and beggin me to stop, and then fuck it some more. I knew once you were in gen pop that you'd take it up the ass so many times that your butt would be a cock expressway, and I wanted to get the first ride."
"So you didn't get the first ride, but you're gonna get the second. Pretend we're back there."
"Whoa, dude. When you made me mad that time, I was ready to take it out on you. Seriously. I was prepared to fuck your attitude right out of your asshole."
The longer Aidan talked, the longer my dick got, and the more I longed for it. "I'm serious. Imagine we're in that cell together and you have an hour to do whatever you wanted to do me then. You knew the guards wouldn't interfere and they'd laugh at me if I complained. Take a free shot at an ass that looked damn good to you. Turn me into a sniveling pussy like you said."
Aidan seemed to contemplate what I was offering, but he shook his head. "Dude, you have no idea what you'd be opening yourself up for. There's a reason I'm in here."
Although I didn't admit it at the time, in intake I'd felt a thrill when his face turned harsh and he threatened to do me, and I wanted the same sensation. Of course, it wasn't quite the same, because now I knew him and understood he wouldn't do anything like maim me for life, but I sensed inside the box of freckles was a wild man, and I wanted to see him in action. His story about gathering a gang to do Jennifer's uncle and aunt suggested he was more complicated that I'd assumed at first glance. "C'mon, dude. You wanted to do it then and you're even hornier now. You said yourself you haven't gotten off in a week. Gonna be a long, long time before you can bone Jennifer or Jensen, and maybe by the time you're out, they'll have someone else."
I could tell he was wavering, so I pulled out my ace. "Jennifer."
"Jennifer?"
"Yeah. That's my – what do you call it – safe word. If I say Jennifer then back off. But otherwise I want you to do to me exactly what went through your mind that day. I know you wanna do it. You wanted to then and you still do. Teach me a lesson that I'll never forget."
He was silent for a second, but his eyes showed excitement. I couldn't resist one more thought. "You said Jensen likes it rough. So maybe I do too. He doesn't mind what you do to him, and I won't either. You taught him a lesson by ripping his asshole with your dick after he threatened to tell his parents you were fucking Jennifer. I threatened to give you a black eye. You never made me pay for being a shithead. Now's your chance."
He clenched his jaws and the same hard look and dark scowl appeared on his face that I'd seen before. The transformation was complete. He was the Aidan who'd tied up Jennifer's uncle and made him watch while he fucked his wife. He was the Aidan who taught Jensen a lesson by destroying his boi hole. He was the Aidan who fucked up on the outside enough to get thrown in the slammer with me.
What happened next stunned me. I never saw his arm swing until the moment before he slapped me in the face, hard. It was a classic bitch slap. Not as hard as the one Jaxx delivered to me the first night I'd been in the cell with him, but hard enough to stun me. I blinked as he growled, "Clothes off, on your knees, mouth on my cock. And if you don't do it in seconds, I'm gonna beat the shit out of you, rape your faggot pussy and enjoy doing it."
I numbly followed his orders. I'd asked for it, but the reality was jarring. Fearing I'd take another blow at any time, I immediately stripped and got on my knees, pulling Aiden's long dong from his pants, and beginning to lick. The dude was uncut like Jaxx and I loved the silky-smooth feel of his foreskin as I slipped it up and down on his hard shaft. I massaged his huge, hairless ball sac with my other hand, burying my nose in his freshly shaved crotch. I got the impression he shaved his pubes as often as a face, all because Jamar wanted him smooth all over.
The first two men I'd sucked were both uncut. What were the odds that? I loved both dicks. It was inevitable that the time would come when I'd go down on a dude with a cut cock, but I couldn't imagine liking it better than the Black-white duo of Jaxx and Aidan. While Aidan's dick was long, it wasn't the size of Jaxx's huge python, and that was good because it was easier to deep throat. I got some more insights on how to handle the Black stud's massive tool by going down on the white boy's pale pole.
I recoiled as Aidan suddenly ground his boot into my junk, playing with my boner with his foot. "Looks like Little Miss Sunshine likes sucking that big dick. Isn't that right, bitch?" I sorta nodded, my eyes fixed on his rock-hard abs and built chest.
I sucked him for a few minutes before he grabbed my head and began delivering a face bashing with his prod that was every bit as brutal as Jaxx's. Well, maybe not quite as brutal but close. His dick wasn't as fat, so it didn't force my throat open as much, but it was enough of a mouthful to make me gag more than once. Unlike Jaxx, who relished my struggles to deep throat his tool, after the third or fourth time Aidan delivered another bitch slap and got in my face. "No more gagging on my big rod, you fucking little whore. You're gonna make love to it, bitch!" He slammed his shaft back down my throat and I focused completely on suppressing my gag reflex and looking for signals as to what he wanted from me. Mostly, he wanted a wet hole to fuck.
He kept digging into my crotch with his boot, finally slipping it beneath my taint and hissing, "Sit on my boot and work your junk while you're working my dick, cocksucker." My rod was already hard and pre-cumming, but I guess Aidan liked watching it jump as I pressed my taint onto the top of his shoe. Soon I was bobbing up and down on his long dong and his boot as well, my bone bouncing with each movement.
I had no warning – zero – before Aidan's nut flooded my mouth. He started to announce he was cumming but all he got out was, "I'm cuu," before his first spurt of ball juice rocketed from his cock. The stuff was so thick I practically choked getting it down. What felt like a gallon of pent-up goo slithered down my throat and into my stomach.
He looked dazed as he stared down at me. I continued to nurse his cock until it softened, at least somewhat, and then started in on his balls. From there I made my way to his milky thighs. They were as smooth as his chest and abs. I loved licking the inside of his legs and apparently Aidan loved it too, because in no time his cock was back at full mask. He'd barely caught his breath from sperming my mouth when he grabbed my hair and pulled my head back.
"I see Jaxx has taught you a couple of things about cocksucking, bitch. That was a good little appetizer, but I'm not done with you. Been thinking about your ass for a week."
He pulled me to my feet, shoved some books off a table and bent me over it. He roughly pulled my crack apart and spit on my hole several times, then aimed his pale rod toward it. I steeled myself for his assault, holding my breath. When it came I grimaced, but his dick didn't hurt as much as Jaxx's and he forced himself inside me in only three or four thrusts.
"Damn, bitch. I was afraid Jaxx had already ruined your ass, but your asscunt is tight as a vice. You're a lot tighter than Jens, but ever since I took his cherry the little slut has been whoring his ass around like a nympho."
He started to pound my butt and in almost no time it stopped hurting and began to feel awesome. It wasn't quite the rush I got when Jaxx's hard chest was against my bare back as he buttboned me – I didn't get the same euphoric sensation of dominance and superiority that seemed to seep from Jaxx – but my own dick was rock hard and once again I was wishing I'd figured out how great it felt to get fucked a long time ago. I should have let those photographers who wanted to do me have their way. I could have made some fricking great money selling my ass, enjoyed every minute of it, and maybe even gotten into modeling too.
Aidan reached down to my knees and picked them up, leaving me balanced precariously with only my chest on the table. He pulled me backwards, continuing to sink into fuck hole. "Yeah, this is good. I can get farther inside your tight boi pussy this way." He ramped up his already rapid pace until he was fucking me frantically. Between panting, growling, and slamming into my butt, he was making enough noise that I wondered if the inmates in the library would hear us.
"You like my big cock in your twink twat?"
"Yeah. Fuck that ass!"
"You're a fucking whore for cock. What else did Jaxx turn you into?"
He continued to rail on my hole. The dude fucked like a madman. He was the Energizer Bunny with a steel hard-on, with only one speed, full throttle. Three or four times he paused for a long spell, and at first I figured he was just edging, prolonging the fuck. But my ass got sloppier and sloppier and I began to think he'd shot a couple of loads into my fuck chute. Sure enough, when he finally pulled out and shoved his cum-coated fuck stick into my mouth, he confessed he'd cum four times. I'd stumbled on a fuck machine with amazing stamina, able to climax back-to-back-to-back-to-back and start a new fuck after only a few minutes without ever pulling out. He flooded my mouth with a load that had to have built up over a week and then seeded my butt with four more nuts.
As we dressed, Aidan got an evil look on his face and grabbed my neck, slapping my face and sneering at me. "Better get used to servicing my fuck stick, slut. Every Friday night I have the use of your holes. But it looks like your leaky rod got some dick slime on my boots when you were bouncing up and down on them. Lick `em clean." I did it, thoroughly licking his boots, although I liked the taste of his spunk better. I liked kissing Jaxx's long feet better, too.
As we left, it was obvious every inmate in the library figured out what we were doing. I got plenty of hungry stares. Now that I understood how great it felt to get dicked in the ass, I would have tricked with several of them, but it wasn't going to happen anytime soon. None would chance touching the property of a Black God.
Aidan was back to being my friend as we head out of the library, totally different than the dude who'd slapped me minutes earlier. "Um, I didn't go too far did I?"
"I never said Jennifer."
"Nah, you didn't. You're all right, Sunshine."
Later that night, after the guards killed the lights in the cell block, Jaxx put me on my back and pushed my knees up to my head. He barely used any spit on his big monster before aiming it at my abused hole and slamming into me. I gasped in surprise, realizing how much more my ass was forced to stretch to accommodate him. But his big black cock hurt less than it had before, and in only a few minutes my boi pussy felt great as he powered into it. My dick responded by quickly hardening into a stiff erection that was inches away from my face. The longer Jaxx pounded me, the closer it got to my mouth. I'd never tried to suck my own cock before, but I was pretty sure I could if I positioned it just right. It didn't matter because I wouldn't be doing myself for a long time.
If Jaxx was bothered by getting sloppy seconds – okay, technically very sloppy fifths – he didn't let on. I think he liked having Aidan's cum as lube and not having to work so hard to get his dick all the way up my asscunt. He had to know I'd been fucked earlier, because sloshy sounds filled the cell as the he pummeled my boi pussy. He ramped the fuck up, reaching a frantic pace, and it crossed my mind that he was making sure I realized that nobody could fuck me as thoroughly as he was. My ass felt like it was on fire.
Predictably, my cock didn't hold out long. It had been hard for much of the night, first as Aidan collected his reward for helping to turn me out and dumped boatloads of cum in me, and now as Jaxx delivered a brutal buttfucking. I tried to steer away from a climax but it was no use. Egged on by the big snake drilling my hole, my cock shot, coating my face with ribbons of slime. Jaxx nutted not long afterwards, adding his black ball jizz to the cum cesspool in my ass.
As I drifted off to sleep with my own spunk crusted on my face and my ass leaking sphlooge, I realized getting buttfucked by Aidan had one big plus. He'd opened up my boi pussy enough that Jaxx's big black cock hardly hurt. From then on, I loved Friday nights, not only because I liked working Aidan's white pole but because when the lights went out and Jaxx's dick went inside my hole, it felt better than usual.
* * *
As Aidan suggested, he apparently had permanent use of my ass every Friday night while Jaxx and Jamar were playing ball. The dude was sorta like Jekyll and Hyde. When we hung out or ate together, he was my best friend, happy, laughing and helping me out. It was almost like he was my big brother. But once we got into the room behind the library on Friday night, he turned into a sadistic, dominant stud, intent on fucking me into tomorrow. It was like he was channeling Jamar. I liked the combination.
After several of our weekly fucks, Jarret, the white gay boi who liked me, showed up at the library room one night. I was puzzled as to why he was there, but he was smiling big and knew exactly what was going down. "Damn, am I ever going to like fucking your tight butt." He pulled out his cock and Aidan gave me a look that suggested I'd better chow down on it or else.
I'd never seen red pubes before, but I quickly went to work on Jarret's dick. It was normal sized, certainly not as big as Jaxx's or even Aidan's and maybe a little smaller than mine. It got rock hard, however, and once the skinny twink got his bone up my ass he bonked my butt like he was getting his last piece of ass ever. He and Aidan spit roasted me, passing me back and forth until my jaws threatened to cramp and my ass was leaking nut. The last time Jarret did me, I was on my back with my legs on his bony shoulders when he bent down and started kissing me. I was startled at first. I'd never kissed a guy before, so it was a first for me, but I kinda got into having his tongue in my mouth while his dick was in my ass. He did too, because he came fast despite having already dumped a couple of loads in my holes. Afterward, whenever we'd be someplace where only the wives and prison bitches were around, he begged me to kiss him. Sucking face with him was okay. He always sprouted a bone and wanted to feel me up and I pretty much let him do what he wanted.
After the night Aidan and Jarret had their way with me, I couldn't walk without boi jizz sliding down the backs of my legs, leaking from my hole like a persist drip from a faucet. I'd come full circle. Jarret was the type of kid I would have coaxed into sucking me off and bottoming for me on the outside. Now I'd swallowed his spunk and let him shoot days of pent up jizz into my butt. I was totally at the bottom of the prison pecking order. Even the prison wives and hos fucked me.
Afterward, I asked Aidan why Jarret had been there. He was noncommittal, only giving me a bland smile and offering, "I invited him." I didn't press him as to why, but two things were soon apparent. In exchange for the chance at my ass, Jarret accommodated Aidan by giving it up to him during the week. Only getting off once a week in my ass apparently wasn't enough for the horny hayseed.
The week after Jarret buttboned me, Steven showed up with Aidan. The Black kid was all business, merely wanting to dip his sleek black stick into my fuck hole and nut – which he did three times. The fucks convinced me he was straight. He was merely getting off and wasn't turned on in the least by doing it with another guy. He kept his eyes closed and I don't think he said a single thing while he banged me, other than maybe a couple of, "Fuck yeahs!"
Aidan continued to cash in on his good fortune of having free use of my holes on Friday nights. The week after Steven, another inmate appeared, a tatted Latino boy ready to shove it up my ass and fuck my brains out. After that, a series of dudes lined up to sperm me. A different inmate or two met us every Friday, eager to empty their balls in my holes.
Aidan was totally pimping me out. I don't know if Jaxx knew. Maybe the Black God didn't give a shit, or maybe my buddy was taking a big risk. Regardless, I kept my mouth shut, knowing that Jaxx would take it out on me if Aidan was operating without permission.
I knew Aidan was getting something in return because that's the way prison worked, but other than with Jarret, I never knew what. He was my best friend so at first I was a little miffed that he was using me, but I finally accepted it as just a consequence of prison life. He totally channeled the Black Godz during those nights, proud, dominant and in charge, brutalizing my butt and slapping me around like I was a cheap whore he owned. It was completely unlike the goofy hayseed he was at other times. I liked the Friday night fucks and didn't mind getting two or three cocks up my fuck chute, because that ensured Jaxx's big python hurt less when he bred me. Worshipping the God's muscular body and feeling his monster cock inside me was still the highlight of my day.
TO BE CONTINUED...
Author's Note: My plan is to post the next chapter in a week or two, luck willing. Hope you enjoy it!
Reactions or feedback? Please send them along! Coltonaalto@gmail.com
My other Nifty stories can be found in the author index (listed as Colton) using this link: https://www.nifty.org/nifty/authors.html#colton. You can also locate them by searching for "Colton Aalto" using the Nifty Archive Search button, or by following this link: https://search.niftyarchives.org/?keywords=colton+aalto&sort=Relevance (I like this link better). I jump around in different Nifty categories, so you'll find a bit of everything. Enjoy!
I've also recently published a book, "Lance & Leo", a fictional account of 1980s gay porn with some sci fi thrown in. https://www.amazon.com/dp/1590217314/
© Copyright Colton Aalto 2020