Oz Beach Boy Prison Anal Letter

AUTHOR'S NOTES:

This is an entry in the CRIME AND PUNISHMENT 2024 AUTHOR ORGANIZED CHALLENGE, so I'd really appreciate it if you could take the time to leave a score.

This story takes the form of a letter received by my recurring character Matt (a muscular, well-hung, sex addicted Aussie male exhibitionist in his twenties) from his father Jack "Bull" Tyson (a former American porn actor and bank robber serving several life sentences for multiple murder in California's Pelican Bay State Prison). This relationship was established in my previous story "Oz Beach Boy Looks For His Father."

In this letter, Jack recounts his abusive relationship with a female prison guard, and his eventual act of revenge via anal sex.

This is a very gritty prison story, and features CFNM, stripping, humiliation, femdom, reluctant consent, fellatio, cunnilingus, female-on-male anal pegging and male-on-female anal sex. This is a work of complete fiction, and includes strong violence, much coarse, potentially offensive language, and plenty of rough prison talk. All characters are over eighteen.

I am endeavouring to write a CFNM "Oz Beach Boy" story in every Literotica category. This entry: "Anal".

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Hi Matt,

Hey, kid. Thanks for your last letter. Man, I can't believe some of the shit you get yourself into. One minute you're walking along a beach in Melbourne, and the next minute you're spit roasting a hot old bitch with her husband! You're a goddamn sex magnet! If there was ever any chance of me getting out of here -- which there ain't; it's back door parole for your old man, make no mistake -- I'd be on a plane to Australia and setting myself up as your fucken wing man! We'd pull in so much pussy, Matt!

Well, kid, I wanted to send you another letter, which got me to thinking about what in the high hell I had to say. Right now, I'm pretty cool in here. I'm pretty much an OG, and almost a sucker ducker too...that keeps me right out of trouble. So, as usual, that got me thinking about my dark, sordid past, which got me thinking about Captain Ramona Ramirez. There's some pretty heavy shit in this letter, and again, thanks to the duck CO I've got on a string, it's been snuck out to you unredacted and un-fucked with. The straight fucken dope.

I've told you a little about that fat-assed Mexican bitch Captain Ramona Ramirez in some of my other letters, so you know her a bit already. My feelings about her have always fucken confused me. I did the crime and I've got no problem doing the time -- them's the rules, kid -- but Captain Ramona Ramirez's brand of punishment was fucked up. She's long gone out of Pelican Bay now, but she was a pretty sick sex fiend back in the day, and she really made me pay for what I did.

Sure, having ol' Ramona around meant that I got plenty of pussy, even inside, but I think her brand of punishment might have fucked me up somewhat in the head, even more than I was already fucked up. The bitch nearly sent me to the ding wing.

As soon as I got sent down, Captain Ramona Ramirez was on my ass. I told you about that first Christmas when ol' Ramona and her pals pulled a train on me, and then when she made my boy Toby Dallas suck my cock while all the other COs watched. You know about that shit, but that wasn't the all of it, kid. Captain Ramona Ramirez fucked with me right up until she retired. Like I said, the pussy was great, but the sick shit fucked with my self-esteem some, you know?

After that first Christmas, Ramona basically made me her bitch. She'd swagger into my house and tell my cellie Richie Ravenhawk to beat it. He'd fuck off to the yard and probably terrify some fish just by eyeballing him for nothing more than the fun of it, and I'd be alone with ol' Ramona.

When I first hit Pelican Bay, she was in her early forties and I was in my twenties, so there was an age gap between us. She had some serious Mexican MILF shit going on. Ramona would make me eat her pussy, and then treat me like a human dildo, riding me till she blew and screamed like a stuck pig.

As you know, I'm still rock hard now, kid, and I spend hours on the weight pile, but back when I first got in, I was in incredible fucken shape. I was handsome too, before all the years of prison fights roughed up my face some. You've seen some of my fuck flicks -- you know I was hot fucken shit...a real handsome fella, if I do say so myself. I did win a couple of porn industry awards back in the day...Best Cock and Best Face, not a bad double.

Ramona Ramirez had seen my fuck flicks too, and she liked to imagine she was Catalina Cruz, a hot Mexican porn actress and anal specialist who I made the movie South Of The Border, Right In The Butt with. Catalina was a real beauty, but even though Ramona admired her, the tough CO never let me tap her in the ass. She guarded her plughole like it was a national treasure, the bitch. Me and Ramona fucked like we were on camera though, that's for damn sure. It got pretty hot and heavy when she occasionally just let me fuck her the way I wanted to.

As well as fucking me in my house, Ramona would jerk me off in the shower block, and summon me to her office for some sweeter, longer loving, the kind where she'd let me get all of her clothes off. Ramona Ramirez had big titties, a big, curvy, pock-marked ass, and a bush so thick she would have needed a chainsaw to trim it. She was fat, but no dump truck, and she was seriously hot...especially to a motherfucker in the joint not getting any.

On top of our one-on-ones, Ramona also began to use me as an initiation ritual. Whenever a new kitty started work at Pelican Bay, Ramona would have a party in the shower block. Just like that first Christmas, I'd have all my clothes ripped off by a bunch of kitties, then get hosed down, and then get gang-banged. Some of the new kitties refused, but others got into it, and either way, Ramona and her older kitty pals all fucked me until they were as happy as pigs in shit.

Even though I'd robbed banks, given so many beat downs I'd lost count, and killed all those cops and rent-a-cops, being gang-banged on repeat by women initially made me doubt my manhood. I liked fucking Ramona and some of the other kitties too, but I felt like a punk, and I dreamed about getting payback on that fat-ass Mexican bitch. To keep me on the hook, Ramona got me contraband shit too -- wham whams, bats, jack books, toochie -- so sometimes it felt like it was worth it.

Ramona eventually got heavier with me. Word got around amongst the COs about what Ramona was doing to me, and she'd occasionally shop me out to hinky male COs too. As you know, I did some gay fuck flicks too, so I was no stranger to gay shit. Even though most of these COs made out like they were just fucking with me and busting my balls, I could tell that they was queer. I ended up sucking a few cocks, but none of them ever fucked me in the ass.

As the years went on, the same ol' strip, hose and fuck routine obviously got a bit tired for Captain Ramona Ramirez. She had such free reign with me, it was like she had to get nastier to get herself off...and that's when she introduced the fucken nightstick.

Though I've never taken it in the ass involuntarily from another convict, Ramona got me to give up my permanent pocket, and it fucked me up...not like I'd net out or shit, but it did fuck me up. The bitch had the power, you know? That shit hurt. It made me feel weak, and I don't like that feeling...I don't fucken like it at all.

Sorry for laying this on you, kid...it will get better, I promise, but I've just got nobody else to talk to about this shit. It helps me to get it all out, you know? If there's ever any heavy shit you wanna hit your old man with, you fucken lay it out, kid, don't think twice about it. We're tight, Matt...not like the usual father and son, of course, but we're still fucken tight. I don't know how much I can help, but you can talk to me, kid.

I'll never forget that first time when ol' Ramona went for me with her nightstick. She'd been fucking with me for about five years, letting her fellow kitties use me as a plaything, and fucking me whenever she felt like it. I got the call to go to Captain Ramirez's office, so I straightened my shit, and booked it out of my house.

"Lick that pussy good, hoss," Richie Ravenhawk said and winked at me. "Lick it till that bump is gone, stud."

"Thanks, Richie...don't kill anyone while I'm gone," I said to my bank robbing, tough-as-fuck Apache cellie, and lit out of there.

When I walked into Captain Ramona Ramirez's office, I got a shock. The tough Mexican bitch wasn't alone. This wasn't gonna be a sweet and long fuck like I thought. Standing next to Ramona laughing was Officer Brooke Heinrich, that fat, fucken dump truck CO I had to eat out that first Christmas. Remember her, kid? She was a fat, ugly, mean-spirited bitch, and I did not like fucking her, not one bit.

Also in the office was Officer Lou Maretti, an Italian CO who had even bigger titties than Ramona, but a smaller and cuter ass. She was likely in her forties too, and she was hot, like a Mafia wife or some shit. There were no new kitties. It looked like I was gonna be partying with some older bitches. I was horny, so I hoped it would just be the standard strip and fuck deal. I was wrong.

"Well, roll out the red carpet, it's Jack 'Bull' Tyson, the star of Operation: Asshole and No Pants, No Pity," Ramona said with a laugh, dropping the titles of two of my gay fuck flicks. "Here he is, ladies. The biggest cock in Pelican Bay!"

"Ooh, he's a hot one, ain't he?" Officer Lou Maretti asked with a wink, and then started to unbutton her uniform shirt. "I've been eyeballing this hunk's ass since he got sent down. I'd like to break him out so all my sisters back in Jersey could fuck him. He's a hot young thing."

"You won't be disappointed, Lou," Brooke Heinrich said with a sneer, and ripped open her shirt, showing off her big, sloppy tits in their hard-working bra. "He looks even better with all his clothes ripped off."

"Speaking of which, why does this bitch still have his drawers on?" Ramona asked with a big laugh. "Let's strip this punk, ladies."

Officer Brooke Heinrich pulled her shirt right off, and Lou Maretti opened hers right up and untucked it, giving me a nice view of her red lacy bra, which showed off a lot of sexy cleavage. Her stomach was flat, and she had beautiful olive skin. Officer Lou Maretti was a righteous fucken babe.

Captain Ramona Ramirez gave me a cruel smile, and then the three older bitches were on me, their long-nailed fingers ripping at my blues. I put up a half-assed fight to make them feel tougher, but I basically let the three old kitties have me. I'd be getting some pussy, so I just let it roll.

While Captain Ramona Ramirez laughed her fat ass off, Brooke Heinrich and Lou Maretti ripped my t-shirt up and then over my head, my ponytail catching for a few moments but not stopping it. Brooke flung my ripped off t-shirt over her shoulder, and while I was getting my balance, Ramona quickly slid her right hand between my legs. I felt that all too familiar rush of pain as the fat-assed Mexican bitch grabbed my cock and balls and then gave them an almighty squeeze.

"It's still there," Ramona cackled, and then clamped down tighter. "I can feel that johnson! I've got a hold of his nuts!"

I groaned in pain, and then Brooke Heinrich and Lou Maretti, both now wearing just their bras and uniform pants and boots, threw a double on me, driving their shoulders into me and dropping me with their combined weight. Still in pain from Ramona's ball grab, I went down easy, grabbing at my nuts.

Brooke and Lou grabbed my kung fu joes and ripped them right off with my socks too. My shoes went flying and then the three kitties went for my pants like wild dogs on heat. I felt fingers clawing at my cock and balls as three sets of female hands wrenched my pants down my hips and then right off my legs altogether.

I watched like a bitch as my pants went flying into the air and then landed on the other side of the office, leaving me in nothing but my white boxers. As my pants were ripped off, my huge johnson slid out of the side of my shorts, which prompted wild, raucous laughter from the three kitties.

"We just got a preview," Ramona hooted, and then unbuttoned her shirt, her big titties coming into view, held up by a black, lacy bra. "Look at that anaconda! The bitch can't keep it in his panties! Bull can't control his hose!"

"Fuck it, they've gotta go...let's get those panties off," Lou Maretti laughed, and then the three kitties were at my boxers, ripping them off and sending them flying.

"That's the way all these convicts should be...bare ass naked," Brooke Heinrich whooped, "with their dicks and balls hanging out for everyone to see! And for easy access!"

Brooke then dropped to her knees and grabbed my cock. Laughing and cackling, the dump truck CO then started jerking me off, pulling on my joint hard with her fist. Just the feel of a woman's hand on my cock was enough, and I started to get up, even though Officer Brooke Heinrich was a fucken mess and no turn-on.

"Whoa, whoa!" Ramona shouted. "Let go of his johnson, Brooke! I've got other plans for Bull today. Get him up, ladies...bend him over my desk."

"What the fuck?" I muttered, and Ramona slowly slid her nightstick out of the loop on her belt, and then held it up in front of my face.

"Bend him over," Ramona said with a snarl, and her two kitty bitches grabbed me by the arms and then pulled me up off the floor naked.

"Captain Ramirez...what are you doing?" I asked hopelessly. "What the fuck?"

"I'm really gonna fuck you today, Bull," Ramona replied, and pulled a tube of lube out of her desk drawer. "You fucken cop killer!"

"Oh, fuck," I muttered, and Ramona squirted lube all over her nightstick.

"Bend him over," Ramona said again, "and spread his legs...wide."

Brooke slapped me across the back of the head, and then Lou kneed me hard in the balls. I crumpled at the knees and then the two kitties pushed me down onto the desk, my face hitting the hard wood while my balls screamed in pain. Lou then kicked hard at my ankles until my legs were open wide.

I knew I could have fucked these bitches over in seconds, but then I'd be looking at LOC, LOR, LOV, LOM and likely moved or dumped in the hole. Plus, kid, I've never been into hitting women. That just ain't my bag, you know? So, I basically took it like a bitch, just like I usually did with Captain Ramona Ramirez.

"Oh, we are gonna fuck you good," Ramona said, and Brooke and Lou grabbed my arms to hold me in place.

I then felt Ramona's lubed up nightstick pushing up against my ass cheeks, which got pulled apart seconds later as it went in. Ramona grunted with the effort, and then her nightstick was right up my ass. I groaned with pain, and Ramona started to slide it back and forth, in and out like a gentle jack-hammer. I was being fucked in the ass.

Maybe I deserved it, you know? For all the shit I've done? Though I sometimes think of cops as soldiers to be dropped in a street war, I also sometimes feel guilt for killing all those pigs during the bank robbery. They were trying to take me down, but did they deserve to die? I don't know, kid. Maybe Captain Ramona Ramirez was exactly the punishment I goddamn deserved. I'd fucked a lot of people in the ass in my life, and maybe now it was my turn. Who the fuck knows, huh?

The more Ramona slid the nightstick back and forth in my ass, the more I got into it. I liked all the kitties being around, and though it hurt, it was kinda sweet too. While Ramona ass-fucked me, Brooke and Lou kissed me on the neck and rubbed their big titties all over me. They both unhooked their bras too, and I could feel the bare flesh of their titties and nipples, which got me even hotter. It was a sick scene, but a hot one too.

"You like taking it in the ass, Bull," Ramona taunted me. "I've seen your movies...I knew you'd like it in the ass... you're a bitch. A cop killing, punk-ass bitch. Give me a little moan... ask for more...and then Lou might reach under the desk and jerk you off."

"Oooooh," I moaned, embarrassed as all hell. "Fuck me, Captain Ramirez...fuck me in the ass."

"Am I the boss?" Ramona asked, and pushed the nightstick right up my ass.

"Yes, you're the boss, Captain Ramirez," I replied. "You're in charge...this is your show."

"Milk him, Lou," Ramona said with a laugh. "Jerk him off."

As Ramona pounded me from behind with her nightstick, Officer Lou Maretti slipped her hand under the desk and then groped around until she found my cock, which had gotten good and stiff. Lou wrapped her long-nailed fingers around it, and then stroked it back and forth while cooing into my ear.

"Big Jack...no clothes...fucked in the ass...robbed of his dignity...just what you fucken deserve, bitch," Lou said coldly as she pulled my cock. "My brother's a cop...you fucken cop killer! Fuck you, bitch."

Lou jerked me off until I came all over the floor of the office. Ramona made me clean up my jizz with a paper towel, and while I was on all fours bare-ass naked, the three kitties unbuckled their belts, popped the buttons on their uniform pants, and then unzipped.

"It's pussy eatin' time!" Ramona hollered.

The three old kitties all got naked, and then took turns lying on the desk while I went down on them. I had no trouble getting Ramona and Lou off because I was so into it, but it was tough with Brooke. Her pussy was like a fucken bomb site, and she was such a dump truck that I got soft by the time I had my head between her fat thighs. Anyway, my jaw nearly broke, but I finally got the fat bitch off.

Once I'd eaten out Ramona, Lou and Brooke, the three old kitties rolled on top of me, licking my body, feeling me up everywhere, sticking their fingers up my ass, squeezing my balls, and playing with my cock. Once I was up again, they all took turns riding me. I eventually came inside Ramona, and after that it was done. The three bitches ignored me while I got dressed, standing around laughing and talking about me like I wasn't there...like I was nothing.

"Rolled by three women," Ramona laughed. "What a bitch."

"But he's a hot bitch," Brooke added. "Fuck, I'd like to put him out to stud and let all my friends fuck him."

"You don't have any friends," Lou shot back.

"That's true," Brooke said. "I'd just chain him up in my bedroom and keep him there naked. I'd take him whenever I wanted, which would be a lot."

Once I was dressed, I walked over to the door, and began to open it. Ramona told me to stop and turn around. I felt rage building inside me, but I got a handle on it. I tamped that shit down. I controlled it.

"Your ass and my nightstick might have another date soon," Ramona said with a sneer. "You'd like that, wouldn't you, bitch?"

"Yes, Captain Ramirez, I'd like that," I replied, feeling like a wild dog on a chain.

"I own your cock, I own your balls, and I own your ass," Ramona said with a smile. "You're mine. Get used to it, Bull...now fuck off."

I walked back to my house, jacked like crazy. When a j-cat small-timer called Bughouse Bill shoulder bumped me and called me a gump for no good reason, I took my shit out on him, and gave the motherfucker a solid two-minute beat-down. I molly whopped his ass. I felt better after working out some of my anger on this j-cat motherfucker who picked the wrong day to get up in my shit.

For the next bunch of years, Captain Ramona Ramirez fucked with me on and off. She'd strip me for the kitties and then ask them if they wanted to fuck my ass with her nightstick. Most of them said no, like my girl Officer Jordan Laskie, you remember her? She was a sweet one, I told you about her last time. Jordan refused to ass-fuck me, and so did a lot of the other kitties. They weren't all sick sex fiends like Ramona.