Prison Stories

One Night with Alanis by Robert Rosso

From the moment I cracked my crusty eyes open I knew that it was going to be a good day; the smell of freshly cooked moonshine pouring into my cell pretty-much guaranteed it. And sure enough, before I could even get my morning woody to stand down, I heard a quick knock on the door and in walked my black friend, Samir.

“As-salaam-u-alaikum,” said the former crack dealer-turned-student of Islam-turned-moonshine/manufacturer, pornography dealer, and all around penitentiary hustler. “I got that bomb-ass firewater (moonshine). What’chu need?”

I sat up in my bunk. “I’ll take both of those,” I told him, pointing to the two pints he had in his hand. “And I’m starving. What do you have to eat?”

“Let me see what I got.” He sat the booze down on my locker and reached into his kitchen smock. “I got two cheeseburgers and one chicken, egg, and cheese. I’ll give you all three for eight stamps.”

“Bet. Just put it all on my tab,” I said. I mean, why not. I already owed him four-hundred bucks. Another eighty-two wasn’t going to make much of a difference. (Eighty for the two pints; two for the sandwiches).

“What about girls?” he asked, “I got three new Buttmans with some fine-ass white girls. You wanna check’em out?”

“I’m good.” Call me bias, but I only got my porn from one source, Cockbook Brian.

Samir turned and pushed the door open. “Have a fine day, my friend. Drink responsibly.”

I rolled out of bed, grabbed a pint, and guzzled half of it down, just like I do every time that I drink moonshine. I then fixed myself a healthy shot of dope, slammed it in my arm, and ate a cold cheeseburger. I was standing in front of the mirror brushing my teeth when Tommy Rutledge walked in.

“Hey, Tree Top just moved out of cell 263,” he said. “If you’re trying to move, now’s the time to do it.”

I was trying to move; I had to get away from my celly, Troy, a weirdo who was hooked on heroin and Jesus. “I’m on it,” I said. “Thanks for letting me know.”

After guzzling down another half-pint, I lit a smoke, popped a mint in my mouth and headed on over to see Counselor Howard. When I told him that I wanted cell 263, he said, “I’ll let you move in right now on one condition, you get that place painted ASAP.” I agreed.
Shortly after lunch, I cruised on out to CMS (Construction Maintenance Service) to pick up some supplies. No, I didn’t have a pass, and technically I was “out of Bounds,” but I didn’t care – I’ve never been big on following rules.

As I neared the plumbing shop, a friend of mine named Timmy Holloway motioned for me to come up the stairs. When I got to the top of the loft, he reached into his shirt pocket and pulled out a loaded syringe. “You tryin’ to do a shot?” he asked.

“I’m cool,” I said. “I just bought a gram yesterday.”

“Not of this shit, you didn’t,” he assured me. “This ain’t heroin, it’s meth – some real good meth.”

I must admit, I was very curious about trying a shot of methamphetamine. I’d smoked it, snorted it, preferred to drink it in my coffee, but I had never injected it before. But still, to just take a loaded syringe right from somebody’s hand and stick it in my arm seemed a little junky-ish. Reluctantly, I said no.

Timmy picked up on my vibe. “I ain’t got no disease, Robert. And You know how I am when it come to my needles – I bleach the piss out of ’em after every shot.” So here” – he handed me the outfit. “Go on and get’cha some, son.”

If you knew Timmy, you’d know that he’s not some slime ball. Yeah, he looks like a rough character, with sleeved-out tattoos on his arms, bulging green eyes, and long, brown, stringy hair. And yeah, there was that one little incident in Tennessee when he snuck into his girlfriend’s house while she was under police protection and stabbed her to death so that she couldn’t testify against him in an up-and-coming drug case. But setting aside his appearance and that one little mishap, he really was a good guy. I trusted him.

“Alright,” I said. “Let’s do it.” I took the syringe, aimed for the fresh puncture wound on my arm “that I made earlier, and jabbed the thing into my vein. When the blood registered, I slowly released the stuff into my body…and went on one helluva ride.

A bolt of energy shot through me like none that I had ever experienced my eyes twitched, my knees wobbled, and my heart began to gallop; my mind spun like a slot machine -spinning out of control. And right before I was able to fully regain my composure, a bubble of gas snaked through my colon and came screaming out of my ass.

“Wow!” I said, still feeling the intense rush. “That was fucking awesome!” I felt like I wanted to tear my clothes off and run right through the window butt-naked; stand on top of the prison and howl at the moon even though it was dead smack in the middle of the day. I wanted to fuck women – lots of women, just line some whores up and bang my way right through them. I wanted to fight – every last C.O. in the joint, then grab a toothbrush and scrub every crack and crevasse in the chow hall. I was spun-ducky woo- woo.

“I gotta roll, man,” I said, eager to get busy. “I got work to do.”

“Work? What work?”

I told Timmy about painting the cell.

“Hell, don’t just paint the bitch. You gotta hook her up, son,” he said. “Come on. Follow me.”

We went downstairs, grabbed a push-cart, and went zooming around CMS. We stole boxes of linoleum tiles, glue, and three different kinds of paint, along with enough brushes, rollers, pans, and tape to paint a whole cell block. As soon as I got back to the unit, I wasted no time getting started on the floor; never mind that linoleum was prohibited in cells.

Sometime after 9 pm, all the tiles were laid. Now, I had to paint the place.

After 10 pm Lockdown

Alone in cell 263, I had my entire night planned accordingly- paint, paint, and paint, some more. Oh, yeah. And use plenty of drugs and alcohol.

I snorted a line of meth off the top of my locker, took a swig of ‘shine, and cranked up my baby boom box. In the mood for some good ol’ fashioned Rock’n Roll, I tuned in to Kansas City’s leading classic rock station, 101.1 “The Fox.” Immediately, I started singing along.

“Busted flat in Baton Rouge, waiting for a train/and I’s feeling nearly as faded as my jeans/Bobby thumbed a diesel down just before it rained/it rode us all the way to New Orleans…”

I climbed up on the top bunk and grabbed a roller. With the pan already full of paint, I dipped the thing in and started painting the ceiling, still singing away as I did.

“Freedom’s just another word for nothing left to lose/nothing don’t mean nothing honey if it ain’t free, now now/and feeling good was easy, Lord, when he sang the blues/you know feeling good was good enough for me/good enough for me and my Bobby McGee…”

I was really jamming now; the whole painting experience was all that I dreamed it would be, and then some. I was especially proud of myself for thinking ahead- I took all of my property out of the cell and put it on the tier so that it wouldn’t get covered with paint. And it most definitely would have; there was paint flying everywhere.

When I finished with the ceiling, I next hit the walls. Then right before I started on the bed frame, lockers and desk I decided to take a little break – a drink, a snort, a shot in my arm. I was feeling great. It’s not too often that a guy in prison gets to hang out by himself and enjoy the moment, and I most certainly was loving every minute of it. I even took off dancing across the cell as soon as I heard Rod start to sing-

“Who’s that knocking on my door/it’s gotta be a quarter to four/is it you again, comin’ round for more…”

That’s right, “Hot Legs.” And I was really getting in to it. I even started bouncing around on one leg – kicking the other leg in and out as I did, like I had some hot legs. Never mind that my legs (like the rest of my body) are hairy, or that I was dancing around in nothing but a pair of boxers like some big ol’ fag, I was having a blast.

“Hot legs/you can scream and shout…”

Talk about scream and shout. I wanted to shout at the top of my lungs: “Fuck you, Warden Booker! You and Judge Hendron can both take this life sentence and stick it up your pussy’s – bitch!” I went from bouncing around, to shaking my ass, to playing the air guitar. In my mind I wasn’t in a prison cell, I was live in concert, up on stage with Rod and the boys watching a sea of women go ape-shit over us. Sing it, Rod!

“Hot legs/you can scratch my back/Hot legs…”

Out of breath, when the song came to an end I picked up a paint brush and went back to work. I did the locker, the desk, and last but not least, the bed. All I had left to do were the borders, but because I was going to paint them a different color, I had to wait until the base paint dried. So I lit a cigarette and sat down on the toilet.

As I sat there puffing away, it occurred to me that the night was young and I had absolutely nothing to do. The cell was wet with paint, all of my property (including my mattress and chair) was just outside the door on the tier, and I didn’t have any alcohol left. All I had was some heroin, some meth, paint and paint supplies, and a radio.

If only I would have stopped by Cookbook Brian’s, I thought. I could have had myself a nice, private, love fest.

When I’m high on meth, like most meth users, I have a tendency to get very horny. And I most certainly was under the influence of meth. When I’m on heroin, such as I was as well, getting off is next to impossible. Hard-core porn could have helped.

Fuck it, I thought. I’ll just conjure up some memories of those dirty meth whores I use to bang.

I got up, turned down the radio, then washed my hands. As I scanned the room looking for something to dry my hands on, I noticed a magazine peaking out from beneath the bed. I took a few steps, bent down and picked it up.

People Magazine? I must have dropped it when I was moving my property out of the cell, I told myself. For what ever reason, I opened it up and turned to the celebrity photo section, also known as “Startracks.” An array of female stars made my penis perk up.

Hmmm, I thought. I guess fully dressed celebrity sluts beats a blank. Magazine in hand, I sat back down on the commode pulled down my underwear, and searched for an imaginary lover.

Madonna was the first photo up.

Well, well, well, I thought. If it isn’t the Queen of Dirty Whores herself, in the 80s you were ALL THAT, and I even give you kudo’s for turning an entire generation of young girls into a bunch of bi-curious little sluts. But I saw that photography book of yours; you, with your legs gapped and that dog’s nose all up in your crotch. You’re even too skanky for me, M. Next –

The nerve of People Magazine. How dare they put a picture of Gwyneth Paltrow next to Madonna? Gwen, I love you. I want to marry you and pump babies into your guts. I just don’t have it in me to disrespect you – and trust me, if I mentally hose you down while I’m all perverted out on meth, I will disrespect you.

Mandy Moore. Why, look at you, blossoming into a tasty little treat and stuff. You are a Goddess in the making, hon. Please do hurry and grow up.

Brittney Spears, you ugly, trollish, overrated tramp you. I don’t know why so many guys in here have posters of you hanging on their walls. I mean, your moms a dog, which means that one day you’ll grow up to be a dog as well, and there’s nothing even remotely pretty about you now. Pass –

Well, looky here, looky here; Angelina Jolie. Now we’re talking.

I reached down between my legs, took hold of the General, and closed my eyes. Instantly, me and Angelina popped up in a crowded parking lot – she, bent over the hood of a car, me, right behind her plowing away. She tells me to smack her ass; I oblige. She tells me to pull her hair – I’m on it! Some dude walks up to me and says, “Right on, bro!” and gives me a high-five. Angelina looks back at me, snarls, and tells me to go faster; I speed it up. She cries out, “Don’t stop!” I tell her “never.” Someone pours a beer over my head, shouts, “You’re the Man!” I throw up my arms and agree: “Yes! I am the man!”

And then, without warning, my mind went haywire and Billy Bob Thorton appeared right next to us, a vial of his wife’s blood dangling around his neck. My fantasy was ruined; I’m just not the type of guy who could fuck another man’s wife in front of him.

My eyes snapped open. “Fuck!” I said, achingly frustrated. “This is bullshit.” Hand still working it, I look once again look at the photo of Angelina and try again. “Come on, I pleaded with her. “Help me.” But Billy Bob Thorton’s wife just wasn’t good enough.

“Fuck this.” I tossed the magazine on the floor, kicked the underwear off of my ankles, stood up, and put my right foot on the toilet seat, so I could yank away on myself with maximum leverage. I still had enough meth-whores living in my head to last two life sentences, so I decided to put them to use. But just as I was about to close my eyes and take a trip back to 1997, a strange thing happened. I noticed that laying on the floor, captured in between the pages of People Magazine, was Alanis Morissette, who was staring up at me.

Wow! Alanis. What happened to you? You’re looking kind of smokin’ hot, in a strange-little Canadian kind of way. I’ve never thought of you in this manner. But hey, you must be a freak, right? I mean, you do sing about “going down” on your ex-lover in a theater, not to mention scratching your hails down someone’s back. Let’s see what kind of girl you can be for me. Concentrating on the photo of Alanis, I easily slip into a sexual fantasy with her…

We’re on a bed – not just an ordinary bed, but a real big bed, complete with turned down satin-sheets and lots and lots of rose pedals.

“Rose pedals?” I say to Alanis in my fantasy. “This is all wrong. Making love is cool and all, and maybe someday we’ll get around to it, but I’m all hopped up on drugs right now and I’m trying to fuck – you know, some good old fashioned face-slappin’, nail-scratchin’, ass-smackin’, hair-pullin’, teeth-bittin’, genitals-chappin’, methamphetamine-induced sex.” But she acts like she doesn’t hear me, just giggles and kisses my neck.

I’d been rubbing myself for so long, I was starting to chafe. Sweat was pouring out of my body, I was feeling a little dizzy, and I was possibly on the verge of an asthma attack. I had to flip Alanis into the appropriate position and pick-up the pace.

“Now we’re talking,” I tell her in my fantasy. “Keep going just like that.” She was on top of me hunched forward, doing justice to a position commonly referred to as the “reverse cowboy.” The view from were I laid was awesome, Alanis’s wet’n fury hole sliding up and down my pole; her starfish winking at me. But still, the war being wagged between the drugs in my system was very real, and the heroin was kicking ass – I couldn’t cum for nothing.

“Come on, Alanis” I screamed in my head. “Do something! Turn around and suck it – no, bend sideways and -”

And that’s when I heard her voice – not an imaginary voice, but a real female’s voice. She said, “Are you enjoying yourself, Mr. Rosso?”

My eyes flew open in horror.

Let me stop right here to give you a precise image of what took place. There I was, a 30-year-old man approximately 30 pounds over weight, butt-naked, standing over a toilet. I had one foot on the ground, the other on the toilet seat, and I was looking down at a picture of Alanis. From my neck-line to the tip of my toes I was covered with body hair, not to mention all of the specks of white paint clinging to my fuzz. My skin color had to have been beet-red, with big droplets of sweat raining off of my bald head. And of course, in my hand was a pulsating penis from hell, which, I’m sure from an outsider looking in, would appear that I was very angry at. Then without warning, that’s exactly what happened- A female correctional officer named Ms. Keilione suddenly appeared in my cell-door window and caught me sexually assaulting myself. The only thing I could do was scramble for my boxers, which I did and in the process slammed my head against the steel bunk-bed and in front of me and nearly knocked myself out.

Ms. Keilione laughed, “You having lots of troubles, huh?” she said, next. She was a Pacific Islander, probably in her late 30’s, and she was known to be cool. But this was anything but cool to me.

I covered up my privates with both hands.

“You go ahead and finish,” -she told me. “I no come back for two hours.” And as she walked away, I heard her laughing.
From that day forward, every time that I hear Alanis on the radio, see her on TV, or especially, when I see her in a magazine, I can’t help but recall that summer night in cell 263. Yes, it was a very embarrassing experience, yet strangely, I somehow feel connected to her.
Alanis Morissette did what Angelina Jolie failed to do.

Authors note: This was one of many such prison stories that are in my yet-to-be-published memoir, a book based on my experiences in USP Leavenworth. As I’m slowly making my way through the final draft of the manuscript, I keep coming across chapters that I believe make good short stories, such as the one you just read. There will be more to come.


  • PRISON GUARD says:


    • Jason says:

      Great story! I have truly enjoyed reading the stories you have written. Keep up the great work!

    • Charlie Olson says:

      Why would a guy need suicide watch just cuz he’s totally loaded and jerking off. If anything he is trying to live albeit in fantasy land but living just the same. those sound like the words of an angry female guard who takes everything personal……

    • Ben Daves says:

      You must be one of those bulldog big butt female Co’s that nobody even the African American males want so you turn into being a butch only to discover that even a desperate lesbian doesn’t find you remotely attractive

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