Disclaimer/Warning: The following story contains material of an explicit sexual nature. It is completely a work of fiction and is not meant to depict any actual persons or events. It is also pure fantasy and is not intended to condone or encourage the events depicted, nor anything remotely similar, in real life. Do not read or download if you are offended by such material or if you are not a legal adult. Do not make it available to anyone who is not a legal adult.
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The next morning after breakfast, Jesse and I are lying down in our cell before we go back to sleep (breakfast is at 5:00 AM... virtually everyone goes back to sleep afterward) when he says to me,
"Ey.. today I want you to make sure you're like.. good and clean down there for me."
"Oh yeah.. I mean.. sure... Was I.. did I smell bad last time or somethin'?"
"Nah... it's just I want you just to make sure you're ready for me today... Ima split that fuckin' ass in two later..."
Needless to say, later that day I did just as I was told! I even douched myself, using our sink and toilet, with a modified soda bottle I had saved from when I bought it off the commissary. And later on, while he was working out hard, pumping up his beautiful body, I was taking a long, hot shower, making sure to clean myself good for him. The difference between the two of us was very clear at that moment, I thought to myself; a real man, getting his big muscles pumped up, keeping himself in shape... and a sissy fag, showering and grooming, getting prepped to be fucked up the ass... Not that I felt any shame on that account. I truly love being a sissy fag...
I'm sitting in our cell with him, waiting for the guard to come and lock the door. When he does so, Jesse says to me,
"Take you're mat and put it on the floor."
I obediently follow his instructions and place my mat on the floor of our cell. He quickly takes his clothes off, walks in front of me and presses the head of his hard, thick, sweaty boner up to my pussyhole mouth. My lips part as his flat and wide, big piss-slit, dickhead slides in. I'm looking him in the eyes and he says to me,
"Get it wet."
I envelop his shaft between my lips and slowly take all of his hot, beefy inches into my throat till my nose is buried in his moist, brown bush and his plump low-hangers are resting on my chin. I deepthroat him a few times, making sure to get it as wet as I can and he says,
"Take your clothes off."
I do as he says and quickly undress.
"Face down, ass up bitch."
I place my face down to my mat, spreading my legs some, arching my back, and propping my ass up for him. He kneels down behind me, spreads my cheeks and spits on my asshole. He grabs me by the waist with his strong hands and I feel his big, broad dickhead press up to my tight hole. I'm nervous with the sudden realization of how very thick his shaft is, especially in comparison with how tight my little, sissy hole is. I should have known, of course, but was just too excited with the prospect of this straight, white, jailhouse thug "splitting my ass in two."
"Bite down on your pillow," he tells me.
I bite down on it and I feel him try and press into my ass but my timid, little sphincter won't comply, too afraid of the big, scary monster trying to rip it the fuck open.
"Let me in," he orders me with a commanding voice.
I try desperately to make my bashful boy-pussy comply with his demand but still it foolishly resists him.
"LET ME IN!!!"
I bite down even harder on my pillow and whimper and whine pathetically as he aggressively shoves his thick, hairy club up my tight, sissy ass till every inch of his swollen manhood is buried deep inside my faggot fuckin' cunt! My defeated asshole frantically quivers around his meaty shaft and he proudly gloats over me, like a warlord that just conquered and occupied enemy territory. I can feel his pubes pressed up against my buttcheeks. He waits just a short moment till my whimpering is not quite so loud and asks,
"Yeah... Where I'm at?!"
"Ya... You... You're... You're in my ass!"
"Yeah..." he punches me hard in the back, "WHERE I'M AT?!!"
"YOU'RE IN MY A-" before I could finish he starts to pound my ass mercilessly! Fast, deep and hard!
I quickly turn my pillow over to the other side, revealing Jt's skidmarks and bite back down on it. The smell of Jt's dirty shithole provides me with some comfort and I once again am thankful for his present. I concentrate on Jt's sweet, stinky buttstink and the repeated "PAP! PAP! PAP!" sound of Jesse ramming into me in an attempt to dull the excruciating pain. Maybe ten minutes into his savage fuck my tiny hole finally accepts it's fate and doesn't hurt quite as bad, but the pain of his hammer-headed cock punching fast and hard into my guts has not yet subsided so still I whimper pitifully and concentrate on the rhythmic sound and the slapping of his nuts against me as I sniff Jt's rank skids. He slaps me hard on the ass and yells,
"Take that DICK you sissy ass fuckin' bitch!"
He reaches his hands up to my face and puts both of his middle fingers in my mouth and fish-hooks me, pulling my mouth wide open from side to side. After maybe another ten minutes, the pain, which had gone from nearly unbearable to acceptable, has transformed altogether into a rapturous pleasure which feels all the better for the suffering that I had to endure. I reach around with my hands and place them on his firm, sweaty asscheeks, encouraging his hard, brutal ass fuck. I then take one hand and move it to massage his ample, ox nuts. He slaps me hard on the ass again.
"Take that FUCKIN' DICK!!!"
He moves his hands back to my waist and puts one of his feet on top of my head, pressing it to the side, my ear to the floor and his big foot on my face. With the weight of his body pressing into my head I can smell his hot foot-stink through his sweaty sock. He slams into me hard for the rest of In and Out. I know that I will have black and blue bruises from where he has punched me in the back and gripped me so hard by the waist but I don't mind. They would be a testament to the hard fuck he gave me and I would be very proud of them... I gently massage his balls, eager to receive the generous gift they have for me. In my ecstasy, I even dare to slip a finger up his sweaty, hairy asscrack and to my pleasant surprise he allows me to gently massage his slick, dirty shithole.
"Ima fill this fuckin' asshole up!" he says as he fucks me down. "Gonna fill this FUCKIN' ASSHOLE UP!!!"
He then slams into me hard as fuck, his sweaty bush grinds against my buttcheeks and he grunts loudly and punches me hard in the back again! I can feel his thick, manly pipe expand at the base, stretching my boy-pussy even more open! It twitches and pulsates as he starts to shoot his burning hot, heavy load of ball spunk into me. The pleasure of feeling his rock-solid manhood shooting gobs upon gobs of jizz into my quivering cunt is too much for me and without even touching myself I start to orgasm as well! Although, naturally, mine is not nearly as long as his... I can still feel him unload rope after gooey rope of his thick, thug nut into my greedy pussyhole long after my own has subsided. I know, without a doubt, that if my ass were a real pussy, I would be pregnant for sure and that I would be more than happy to have his baby... My asshole grips onto his cock, desperate to keep it inside as he slowly pulls out and just as his dickhead leaves my cunt with a plop he slaps me hard on the ass.
"Damn bitch! That ass was tight!"
"It's yours whenever you want it Jesse, it completely belongs to you," I reply back to him with his hot, stinky foot still on my head.
"Yeah.. I know," he says nonchalantly, grinding his foot on my head, gripping my nose with his toes.
I moan softly into his big, smelly foot.
"Yeah.. You like that?" he asks.
"Mmm Hmm.." I've rubbed his feet and sucked on his toes plenty, he knows I like it...
"I was gonna knock the shit out ya when you messed with my ass... It felt aight though..."
"I couldn't help myself."
"I bet you couldn't..."
"You might have to let me lick it.."
"Hahaha.. I might have to take a SHIT first!"
"If that's what you want.."
"Hahahaa! You NASTY ASS bitch! That what you thinkin' 'bout when I'm takin' a shit in here huh??"
"...Maybe..."
"Yeah.. well.. I mean.. MAYBE I'll let you wipe my ass for me then.."
"Ok."
"Hehe.. you gotta brush ya teeth after though you know what I'm sayin'? I don't wanna smell my shit on ya breath bitch."
After the doors have unlocked and he leaves I grab one of the Styrofoam cups that they give us with our meals from my tote. I place it on the floor and pull my pants down and squat over it. I squirt his tremendous load into it and it fills up half of the little cup. I take it up to my bunk and I pour his entire, sticky wad of thug jizz into my mouth, scarcely able to fit it all in. I didn't want my ass to have ALL the fun after all... and I certainly couldn't just waste it by squirting it in the toilet... So I taste and savor the raw, wild essence of a REAL man while I sniff the stinky finger that had been blessed with the funky, sweet and sour, sweat and shit smell of his grimy, grungy, hairy asscrack and I bring myself to another orgasm while I greedily gulp his slimy spunk down my sissy throat.
Jesse informed me later that night that Jeremiah was gonna stop by and pay me a visit. Jeremiah was a mean, temperamental redhead who could predictably be found around the poker table when he wasn't working out. He never talked to me and I got the impression that he had a "better-than-thou" attitude and surely thought I wasn't worthy of his presence.
To be fair though, he had been in here for going on a year and a half. He had long ago waived his right to a speedy trial in an attempt to fight the case against him, which from what I understood, was pretty bad. Multiple drug trafficking charges for various narcotics plus a lot of prior convictions meant he was looking at some pretty serious prison time. He had been in a higher security dorm for a long while but was moved here months ago to make room for more violent offenders there.
While I was a little nervous around him, I also felt sorry for him... and I also found him to be very stunning. He had an ever-present, angry, "don't fuck with me" look on his face that combined with his short, high-and-tight haircut to give him a very militant appearance which contrasted sharply with his pouty, pink, kissable lips. He was 23 and was around Jesse's height and weight, with pale, ice-blue eyes. Very fair skin like Solja, but with a ruddier complexion and no tattoos (that typical ginger complexion that sunburned within minutes). He had teeny tiny, pale-pink nipples and a small, fire-red, triangular patch of hair on his chest that trailed down his six-pack abs and ended in his pubes. He also had a fat, uncut piece of meat and big, hairy nuts as well...
I was sitting in my cell waiting for him when I heard the guard walking down the cells in the process of pushing the doors closed, thereby locking them. I had started to wonder whether he changed his mind when he suddenly walk in. The guard shut the door just a few moments afterward.
"Go over to the side of the toilet and get down on your fuckin' knees faggot," he says to me.
I quickly walk over to the toilet and drop right down onto my knee-pad pillow. Butterflies flutter in my stomach as he starts to undress. The heady aroma of his sweaty, onion/garlic smelling pits and his dank, musky crotch wafts into my nose and I catch a pleasant buzz from it. My eyes are drawn to his semi-hard, uncut cock as he walks over to me and stands on the other side of the toilet. His foreskin completely covers his dickhead but you can clearly see it's prominent outline through the smooth skin.
"Put my dickhead in you're fuckin' mouth."
I lean over the toilet and softly pull his foreskin back from his glistening, wet cockhead. It's pale-pink, like his nipples and very fat and very helmet shaped. I wrap my lips around it, savoring the cheesy flavor of his previously foreskin covered head.
I look up at him wondering what to do next and just as I feel the burst of his piping, hot piss blast into my mouth he yells at me,
"SWALLOW IT!!"
He rips a piss-fart as I swallow my first gulp of his steaming, salty piss while he looks down at me menacingly. Not only does he plan on using me as his cum-dump, I think to myself, but as his fuckin' toilet too!
"DRINK that piss you faggot fuck!"
I swallow gulp after gulp of hot, salty piss down my throat before his stream finally trickles off. He pulls his dickhead out of my mouth, holding his cock up and says,
"Now put your nose in my balls and SNIFF."
The symbolism of being told to drink his piss and sniff his nuts is not lost on me. I understand that it's probably extremely important for him to quickly establish his dominance. Both over me and the situation. I put my nose up to his sweaty, fuzzy nutsack and and take a deep whiff. They have a strong, cheesy, vinegary odor too them that makes my mouth water.
"Yeah... Good little faggot... Now lick the sweat off of 'em," he says in a deep and husky voice.
I stick my tongue out and lick the sweat off of his nuts as he demanded, enjoying the taste and the feeling of his nut hairs tickling my tongue. I make sure to lick all over his ballsack and in his groin and underneath them as well. I'm taking big, long licks of his dank, hairy taint when he says to me,
"Suck on 'em."
I struggle for a moment to get both of his plump, furry nads in my mouth and when I do he let's go of his cock so that now I can feel the weight of it resting on my forehead, in between my eyes. As I suck on his ballbag I can fell his shaft quickly harden. He flexes it and it lifts up and then smacks back down on my face. He pulls his nuts out of my mouth, grabs a fistful of my hair and points down to the toilet and says,
"THAT.. is your puke spot. DON'T puke on me. Puke in the toilet. UNDERSTAND?"
I nod my head. He grabs another fistful of my hair with his other hand. I stare hungrily for just a moment at his fat fuck-stick pointed right at my lips. Around eight solid inches of stiff, sinewy manhood protrudes from a dense, fire-red bush. Little, blue, delicate veins straddle around his beefy shaft all the way up to his big, swollen, pale-pink dickhead. I know he has a lot of foreskin because even when he was semi-hard it completely covered his cockhead and even now at full-mast it still covers the bottom of it.
"Look at me," he says.
I look him in the eyes as he holds my head firmly in place and presses the head to my lips and slowly shoves his meat down my throat. Inch by veiny inch he crams it in until I stop about one inch short of the base. That bulky, broad head of his is having too much trouble getting down my throat. I was afraid this might happen! Only a few times before did I have a cock that I was not able to deepthroat through some odd combination of length, width and shape. A feeling of dread overcomes me at the prospect of not being able to deliver the full pleasure he deserves. I had thought Jesse's fat tool had beat my throat open sufficiently to handle any cock. I guess I was fuckin' wrong! He pulls it out some, keeping his fat, helmet head in my mouth and then slams it in hard, still stopping an inch short. The back of my throat feels like it's been smashed hard with a mallet! My eyes tear up. He starts to fuck my face some, that swollen head beating hard against the resistance in the back of my throat. I'm gonna have another bad bruise and trouble swallowing again, I think to myself, but I don't mind... He beats it up for a minute or so until the next thing I know...
I'M SEEING FUCKIN' STARS!!!
After a moment...
I regain some awareness...
And I realize my nose is smashed right into his sweaty, fire-red bush! He slammed it in so deep and hard I didn't even know it happened! The next thing I realize, as my eyes dart from his proud expression to his pubes and back again, is that I'm unable to breathe! I instinctively make a choking, gagging sound and grab his muscular thighs and try to push him off of me but his iron grip keeps my disobedient head right in place.
"Is it a big cock??" he asks me mockingly.
My choking subsides and I struggle to hold my breath. He leans towards me slightly and spits a big wad of spit in my face that hits me right between the eyes. I try to breathe again and instead start to choke uncontrollably once more.
"Yeah... Is it a BIG cock?! Is it a big FUCKIN' COCK?!!"
And he just holds me down on it!
I struggle to breathe, choking and gagging, until I think I can't take it anymore!
Finally, he lets me off of it... I wheeze in a big breath and start coughing and whimpering.
"DO SOMETHIN' WITH IT!"
He slaps the shit out of me and forces it back in my mouth, fucking my head and just as before batters that helmet head through the back of my throat! He makes a throat clearing sound and then hocks up a loogie that he spits in my face, hitting me right between the eyes again.
"That's right CHOKE! Choke on it you FUCKIN ' FAGGOT!!!"
I choke on it desperately and feel my stomach churn reflexively and just as I start to throw up he pulls his cock out, aiming my head to the toilet and I puke out my lunch and all of the hot, salty piss he made me drink.
"There you go..." he says softly and approvingly as I look into the slop filled toilet bowl.
He wastes no time and quickly puts his hefty hard-on back in my mouth and slams in balls deep again. I gag but manage not to puke like before. ("Ares," I decide absentmindedly...) He spits in my face again, this one a splatter spray that goes all over. I gag loudly on his cock and then he just starts to hammer deep into my sloppy, pussyhole head! He beats the shit out of it for a while, covering my face with more spit and a couple more loogies. I think to myself how sad and pitiful I must look with all of his spit and snot on my face and my own drool coming out of the corners of my mouth around his big, brawny boner... He smashes in balls deep and holds me down on it again...
And then...
An immense feeling of joy overwhelms me! For not only do I not gag, but I manage for the first time to inhale through my nose, absorbing his strong, stinky pheromones through his sweaty, ruddy pubes! He's stretched my throat out enough that I'm finally able to breathe! High on the sweet, funky musk emanating from his thick bush, I suddenly realize that this was a teaching moment. He the teacher.. and I the student. He was teaching me to be a better cocksucker! I look up at him lovingly as I take another deep whiff of his wet, fragrant bush. He has a knowing, self-satisfied look on his face. He then drags me away from the toilet and puts my head up against the wall.
"Put your palms on the floor," he instructs me.
He then stands on my hands with his big, socked feet, puts his burly pipe back in my mouth and hammers in hard and deep! He bores a hole into my sissy ass fuckin' head as he repeatedly plows his rock-solid, thick thug dick into my bruised but stretched out throat! His big, furry nuts slap loudly into my chin and his musky, sweaty, fire-red bush smashes into fuckin' nose! I feel his heels lift up and I anxiously grip his toes with my hands as he rocks wildly into my sloppy throat and yells,
"YOU FAIRY ASS FAGGOT FUCKIN' QUEER!!!" and once again spits into my face.
He continues to ride hard into my beat-down, wrecked, pussyhole head for about fifteen more minutes until I feel his rock-hard meat expand. Then, to my surprise, he pulls it out and quickly and aggressively pulls my clothes off till I'm just in my white boxer shorts. He forces me on my back on the cold, concrete floor, grabs my boxers with both hands and shreds them in two. He uses the two pieces to quickly wipe the spit off my face and then throws the soiled, tattered remains across the room. He puts my legs over his shoulders, one hand around my neck and the other clamped over my mouth. I can feel him place the stout helmet of his rock-hard boner against my tight, tiny hole. I move my hands to his big, firm pecs and he sinks the head inside slowly and then rams his hard, veiny inches into me till he's balls deep in my sissy-boy cunt! scream
He grunts as I squeal into his his large, strong hand! He stares into my beet-red face as his hairy, husky rod completely dominates my little, fairy buttonhole! A moment passes as I slowly accept his hot, hard, macho manhood inside of my snug, little cunt and my squealing subsides. He moves the hand he has clamped over my mouth to join with his other one around my throat and gets a firm grip. His forehead and nose are pressed up against my own and his snow-globe eyes stare right into mine. I can smell his hot, cinnamon scented breath coming from his mouth, which is close enough to kiss if I had suicidal tendencies.
He slowly starts to pump my girly ass, working up speed until his sweaty nuts are slapping against my cheeks. I move one of my hands to the back of his neck and his lips ever so slightly brush against my own. He lets go of my neck and moves his hands to my buttcheeks, spreading them apart with his strong fingers, his athletic body is now firmly pressed against mine. I feel beads of his sweat drop onto me as he strikes violently into my pussyhole. He pants into my face like a wild animal for a few minutes until I feel his cock once again expand. I move my hands to grip his muscular, sweaty asscheeks, urging him inside of me and he slams in, down to the balls! He then bites down hard onto my bottom lip and grunts loudly,
"URRRRRRRRRRRRGGGGGGGGGGGGGGGHHHHHHHHHHHHHHHHHH!!!!!!!!!!!!"
The base of his cock jerks and contracts as his hairy nuts bust their huge, baking hot wad of creamy, thug balljuice deep inside my faggot fuckin' pussyhole! He grunts and groans as he bites down on my lip, shooting up inside my sissy cunt! I begin to orgasm as I feel his coarse, red bush grinding against my cheeks and his dickhead grinding into my guts. He continues to unload and unload rope after rope until he's put all of his thick, white, slimy seed deep inside of me and his hot, sweaty, powerful body fully collapses onto me.
He slowly takes his teeth from my bruised lip, placing his head to the side of mine and puts his hands to the back of my neck, cradling me. I move one hand from his slick asscheek to the back of his head and gently caress his scalp, neck, and the delicate spots behind his ears. He bites down and chews slightly on my neck. I softly kiss his strong collar, licking the sharp, saline sweat from my lips. I can still feel his dick occasionally spasm as his powerful orgasm tapers off and I know that even now his virile sperm are trying with insane determination to get me pregnant.
He lays on top of me for the far-too-short remainder of In and Out, chewing on my neck and the lobe of my ear. He props himself up, still inside of me and looks down at me with a strange, blank expression. I put my hand to his chest and fondle the little, upside-down triangle of red hair. He smiles slightly and takes his thumb and index finger and tugs gently on my bottom lip. He leans back down, putting his face to mine again, still playing with my lip and then, to my surprise, gives me a little, tiny peck...
He allows me to dress him, which I do so very tenderly while he watches me with a little smile. The ones with the toughest crusts always have the gooiest centers... When the doors open he pecks me on the lips one more time and then leaves without a word...
I once again retrieve my little Styrofoam cup from my tote, thankful I decided to continue douching myself regularly, just in case... Squatting over it I carefully squirt all of his nut into it and am very impressed with his large deposit. Another half cup full... I felt truly blessed. Hopping up on my bunk, I pour his creamy cum into my mouth. It's slightly briny and has a nutty, cashew like flavor. Simply exquisite... I swirl it around with my tongue, running it over the stinging bite-mark he left on my bottom lip and while I feel it coursing it's way down my throat I bring myself to an intense orgasm...
/// Thanks again for reading! Sorry this chapter took so long but I had been in the middle of a move. Many thanks to those who have emailed their support and helpfulness and kindness as well. I always try to respond but if I miss anyone I do apologize. Comments are always welcome! ///