Prison Stories

- - - - - - - - - - - - - - - - - - - - - -

All characters are over 18 years of age. All players are consenting adults.

- - - - - - - - - - - - - - - - - - - - - -

Note from Howard Crunk

Billy Domański and me met in prison. We both got five years. In here they they call that a 'nickle'. We were two-out together the whole time... that means we shared a cell. He and me got to be real good buddies. We had lots of stuff in common, family, business associates, like that, and we came to rely on each other... an important thing in a shithole like this. I counted myself lucky to be bunking in with him.

I was in for burglary. I don't know what Billy did. It's not polite to ask.

He's a good-looking guy, tall and dark with tight curly blond hair - too attractive for this hell hole. In here, a guy who looked like him would normally get used pretty hard but Billy didn't take shit so he was pretty much left alone. He had to prove himself a few times but after that it was sweet.

In prison stuff goes on after lights out.

If you're young you're pretty much fucked... literally fucked. You're kidding yourself if you think you can avoid some sort of sexual assault. If you don't want to discover your feminine side stay out of jail or there's gonna be some monster who wants to make you his bitch.

Billy and me sure weren't as 'friendly' as some. We were straight but, as Tony Soprano so succinctly put it, "Prison don't count." Neither of us wanted anything up the arse but other than that we were 'gay for the stay.'

It's not a big part of the story but I thought I'd mention it. It sets the scene, so to speak. Two horny guys locked up together in a cage. Some weird shit is bound to go down.

Billy was a born storyteller. He'd tell me these amazing sexy stories full of drama and passion and really good laughs. I'd lay awake for hours in the dark, slowly jerking my big hard cock and listening to his deep Illinois accent, letting my imagination take me away until I felt I was a part of the scene he was describing... rather than in that cold hard cell. His stories kept me sane and I reckon telling them to me was good for Billy too.

So this is stories about Billy's grandma. He told me all of it was true, real stuff that happened to him, and while his tales were extraordinary, I have to say they rang true. It was all just too detailed to be faked.

I was what they call a receptive audience. The things he told me about him and her were so hot, and he'd tell it so well, that I'd sometimes loose control and blow my load early... before he got to the good part. Billy always found that hilariously funny.

Anyway, here's just some of the stories Billy told me, all wrapped up in one neat package - late-night jerk-off tales, told after lights out.

- - - - - - - - - - - - - - - - - - - - - -

1977

We was real poor where I growed up. Our little rental flat in Chicago was on the fifth floor, second from the top, five flights up, and five flights down. No lifts in them days.

Old Mrs Bently on the sixth hardly ever left her apartment 'cause it was too tricky for her. Bobby and me'd bring groceries up to 'er every week and if she needed a doctor or anthin', and had to get downstairs, he and me'd link arms and carry her down between us like firemen do.

Our flat was stupid crowded - Ma and Pa, my big brother Bobby, and me was all living there in that tiny place. Two bedrooms, a bathroom, and a kitchen-dining-lounge room. You couldn't swing a cat... but the rent was cheap!

My folks had the biggest bedroom at the back with the view of the alley. Me and Bobby had the other smaller one over the street, not too much bigger than this cell, Howard. It had bare gappy floorboards that needed staining and pale green walls that needed painting. It wasn't much but Bobby and me got on good so it was no big deal.

Wish I was there now Howie, 'stead of this shithole.

Our bedroom was like this.

Next to the door, we had a big old-fashioned wardrobe with a mirror on the door. That took up the far wall. On the other wall was our two single beds that stuck out side by side with an old timber packing case between sitting up on its end like a bedside table. I remember it had INTERNATIONAL DAIRY burnt in it in black letters on the top. We used to stack comics in the front.

Above the box was a storm window with ratty curtains that looked out over the 'L' rail line. At night Bobby and me'd listen to the clickety clack of the train going past.

And that was it, 'sept for the old steam radiator that hissed and clunked all through winter and a table lamp we sat on the box that we'd lifted from somewhere. It was pretty nice. I remember the glass was all psychedelic colours... limy green and orange. At night with it on it was like a nightclub or a strip joint or something.

Our beds were close together and we couldn't move 'em further apart 'cause there was no room. Whether we liked it or not, there was only a few feet between Bobby and me. Way too close for comfort if you wanted to jerk off in private.

As we growed up we stopped worrying about it. We was both doin' it so much we just stopped pretending we wasn't. If one of us accidentally walked in on the other with a big boner in hand, well, it wasn't no big deal. Bobby and me was just two normal horny kids.

It didn't take long to work out it was more fun doin' it together. We used to share the lingerie section of the Macy's catalogue for jerk-off material. By the time a new edition came out all the pages was stuck together. We also had this old Playboy Bobby found at a building site. It had Dolly fuckin' Parton in it Howard! Dolly fuckin' Parton... all dressed up like a fuckin' playboy bunny! Fuck me, we'd cum so hard for her... but not on that glossy paper. We kept that Playboy pristine.

Dolly was so fuckin' hot... still is right? What is she now 80? 90?...and still so fuckin' doable, am I right Howard? Damb straight I'm right. Our ma's a lot like her. Mom's tits are just like Dolly's... before Dolly got that breast reduction that is. What a fuckin' crime that was.

Gotta tell ya, Howie, I miss jerkin' off with Bobby, an' suckin' the jizz out of each other's big knobs. But those sort'a shenanigans can't go on forever... nothing real good ever does.

Bobby couldn't wait to get away and ended up joinin' the navy.

He'd always say how he'd miss me and Ma but he hated the old man's guts. We both did. My father was a big fuckin' loser who drank like a fish. When he was pissed he was loud and agro and when he was sober, he was all tears and 'so sorry's'.

Marrying such a fuckin douche was the worst mistake my beautiful mother ever made. She wasn't stupid or nothin'. She could'a done anything she put her mind to and had any bloke she wanted... if she even wanted one. She was so seriously hot and super sexy, men just stared at her when she walked down the street.

But she married our fuckwit father cause he had a big cock.

My old man gave Bobby and me exactly two things in our lives, our big wangs, and our stupid fuckin redneck names... Billy and Bobby. What a fuckin' joke.

Anyway, once Bobby left, I had a bedroom to myself for the first time.

- - - - - - - - - - - - - - - - - - - - - -

THEN GRAN COMES TO STAY

Granny Rosemary had lived alone in her little house in Joliet for as long as I could remember. I don't remember Granddad at all. He died in the Battle of the Bulge back in '44 and she'd been alone ever since.

All my life Gran seemed like a super-woman. Nothin' seemed to throw her and it was fucked that she got too old to live by herself and had to rely on us. She said she was gettin' forgetful but I never noticed nothin' like that. She didn't forget who we were or how to wipe her arse, so she can't have been too bad. I reckon she might just have been a bit lonely.

Before, when she visited us, or we went to her place, she was always super nice to me. She was nice to Bobby as well but 'specially nice to me.

She'd ask after how things was at school, how the neighbourhood people were goin' and 'specially how my father was behaving. She'd always known what a lazy fuck he was!

I'd also get the biggest bit 'o cake or the extra big portions at dinner time. Now I'm older I realise she was making sure I had enough to eat. When I was a little kid I was thin and small. Gran saw that Ma didn't always seem to have the money to keep my belly full, so she'd feed me.

"Your skin and bones William... you eat all that up," she'd say in her croaky old lady voice.

Nanna gave me lots of affection too - another area where I guess she thought I might be missin' out.

If I stayed over at her place, she read me a bedtime story and kiss me goodnight.

Some of my best childhood memories are of her big lovin' arms wrapped 'round me, my head buried in her big creamy boobs, and her readin' some old adventure story... Robin Hood or Snow White and them little dwarves... like that.

When I was a little bloke I loved my gran like little boys do, but as I got older and hornier I started noticing her sexy big ol' body. She had that same sexiness that my ma had but her tits and arse were huge... gigantic big saggy tits that sagged and an a massive big fat arse.

My first wet dream was of my grandma climbin' up over me and her big ruddy face leanin' down for a kiss. I blew cum everywhere and from then on I was hooked.

'Cause I knew how much she loved me, I started to take liberties. Nothing too serious at first... but like, when she hugged me, I'd bury my face right down deep into her cleavage, smellin' that Pears Soap and Lilly of the Valley perfume she loved.

As I got older my hands'd go walkin' and I'd get to hold a big boob. Through her cashmere sweater was best, but a T-shirt or one of her nightgowns was just as good. She'd pretend I wasn't doin' nothin' but I remember how hard I could make her nipples... like little bullets.

It was the same for her big ol' arse. Her gorgeous big butt stuck out behind her like two big balloons attached around her waist. If I happened to be standing close, like if she was doin' something, like peeling potatoes or standing by the washing machine, I'd accidentally (on purpose) manage to get my hand into the big deep cleft between her butt cheeks. It'd nestle my hand in there real sweet...

...and I could get in pretty deep, especially if she was wearing a dress or them baggy old lady pants. It was warm as toast in there and she didn't mind me doin' that neither Howie.

One thing she really liked, if there was no one else about, was me rubbin' her big belly. She just loved that, sighing happily as I rubbed her through her clothes... in front of the telly maybe... or lyin' on her big old bed.

"It's very relaxing dear", she'd say as I rubbed the big round pot.

Later on, when Ma decided Gran needed more care, she came to live with us.

My dickhead father whinged and carried on but my mom loved her mom more than anything so there was never any question about what would happen. Gran moved into my little bedroom with me and slept in Bobby's old bed.

There was no discussion with me about it and I didn't expect none. This was back in the seventies, right?...before kids were asked how they felt about this or that. And anyway, if I was asked, I'd've said yes. I loved my grandma heaps and I was happy to be able to help her.

She ended up living with us for years and years and most of the time she was just fine. Maybe not always the sharp old lady she used to be but still smarter than any of the dickheads in this place [prison].

When she came to stay, and to sleep next to me in my bedroom, all them sexy fantasies I had about her were runnin' through my mind. I was a real horny young fucker. But even so the best I dared hope for was to catch a glimpse of her tits.

I had no idea it'd pan out like it did.

- - - - - - - - - - - - - - - - - - - - - -

BILLY AND GRAN'S BEDROOM

Right from the start we was real good together, Gran and me. We got along just fine. Every night we'd take turns in the bathroom, shower, brush our teeth, get ready for bed... like that...

When Bobby was around he and me used to sleep naked but I couldn't walk around like that with my gran. I'd jump into bed wearing my underpants and then drag 'em off under the covers.

Of course, Gran was different.

Whether it was stinkin' hot or freezin' cold Gran wore nightgowns. She had a bunch of em, covered in faded roses or little bluebells or some other pretty flower...there was one with little pink hearts. Some were long... down to her ankles, but heaps of 'em were pretty short... mid-thigh or just over her knees.

When she wore those ones, which was often, she showed off lots o' leg. Real nice legs too for an old bird, slim ankles, shapely calves, up to her big round feminine thighs...

I remember, on the very first night we shared a room, Gran bent down to get something out of one of the low drawers in the wardrobe, and I got a good look at her big luscious arse... like the sun risin' in all its glory. That short nightdress rode right up over those marvellous big globes and I saw everything... her pretty puckered asshole and her big gappin' cunt... that tantalising dark hairy cavern... just made for my big cock.

Apart from me sometimes catchin' glimpses of her body, nothin' happened straight away. It was little by little, day by day and week by week. We got into a routine, she and me, sleepin' side-by-side in them little single beds just like Bobby and me used to... 'sept no jerkin' off together or cocksuckin'. I had to jerk off under the covers.

We'd read a little before we went to sleep. Gran was a big reader, always readin' some big book. She's the one got me into it.

"Books let you travel without going anywhere, Billy," she'd say.

So I gave it a go. I figured I sure wasn't gonna see the world any other way.

At the time I only had comics. I was partial to The Flash and The Phantom. Pretty soon though she had me readin' Treasure Island... what a fuckin great story. Then Tom Sawyer... T' Kill a Mockin'bird... Lord o' the Flies... all them great stories. I tell you this Howard, I got more from them books than any teacher could ever teach me.

When we heard Ma and Pa fuckin' we'd just keep reading, pretending we couldn't hear the headboard bangin' against the wall or the two of 'em screamin' and yellin'.

I remember glancing over at Gran wonderin' what she was thinkin'. But she just settled back against her pillows with her slim little bifocal glasses on the end of 'er nose, looking down at the book she cradled on her belly like nothin' was going on in the next room... as if fuckin' like that was just as normal as normal could be.

Just havin' 'er there, lying beside me, made me hard. I thought she was so fuckin' sexy Howard - and with ma and pa carryin' on in the other room - I'd be reading (and re-reading) as I fondled my hardon. Gran'd sit her beautiful big tits out over the top of the blankets. I used to think her gigantic cleavage always looked as though it was about to bust out of her nightdress at any second... big nipples outlined through the soft material... mmmm... so suckable...

When Mom and Dad finished fucking for the night, that was our cue to turn our bed lights off but we'd chat a little before we went to sleep. I loved listening to Gran talk. Her raspy old voice was like honey and molasses.

The street lights outside glowed soft through the window between us, bathing us both in a pale yellow light. I could see the silhouette of her big booby body beside me, no more than three feet away.

With the clack, clack, clack of the 'L' going past, I'd listen to my nan tell stories of her past - jobs, adventures, old friends, all the time jerkin' my big cock to the sound of her husky old voice.

Her yarns were great and she had 'em down real good. That dear old lady taught me how to read, tell stories, and then how to fuck.

- - - - - - - - - - - - - - - - - - - - - -

CHICAGO WINTER

Nothin' happened between us till the winter of '77 when it got bitter cold and our little bedroom was freezin'.

There was an old cast-iron radiator under the window but it was an iffy kind of heat at the best of times. My ma complained to the landlord but nothing ever got fixed. All we could do was pile on the blankets.

One night I woke up to the sound of my gran whimpering.

It was so fuckin' cold I started shivering straight away. The fuckin' radiator had completely crapped itself - no heat at all. There was ice coverin' the glass on the window between us and my breath fogged like I was smokin' a cigarette.

"Are... are y... you okay n... nan?"

"C... cold... Billy. Soo... c...cold."

The sweet old lady was standing over my bed, the street lights reflecting off her lush curvaceous body. She was huggin' herself and shiverin', looking down at me real pathetic.

Without thinking I pulled my blankets back, for the moment forgetting I was naked. Nan didn't hesitate. She climbed into that little single bed with me and, laying on her side, pushed her big butt up against me. She was like ice, shivering like crazy...

"I'm... so c... c... cold B...B... Billy..."

My right arm was already under her big soft bulk and I put the other over her belly, cuddlin' her close. After 'bout ten minutes, she was warming up. Still shakin' a bit but not as bad.

"You're like a hot water bottle Billy," she whispered. Her voice was soft and husky like... sexy soundin'...

Gran's big soft bottom was pushed up against me.

When she'd got into my her nightdress had ridden up 'round 'er waist. We was skin on skin. The warm flesh of her big fat ass enveloped me...

...I'm tellin' yu straight Howie, it wasn't intentional but my big hard cock was resting into the cleft of her butt and I was immediately hard as fuck.

"It is better, isn't it Gran?" I mumbled half apologetically. "Our... you know... body heat... and all that..."

"It's so much better Billy dear," she sighed, sleepily wigglin' her big bare bottom back against me. "Thank you for looking after me so well."

"I'd do... I'd do anything for you Nan," I gasped as my erection explored deeper and deeper between the big warm butt cheeks.

"I love you, Billy," she murmured.

I didn't know what to do. I was squeezing her tight. There was nowhere for my prick to go but between her legs...

"I love you too Gran..."

...my whole big thick ten inches was proddin' up against her like it had a mind of its own. My face was pressed into her her short curly grey hair...

... I was so fuckin horny I couldn't think straight. I remember that Lilly of the Valley old lady perfume she always wore. That smell makes me bar-up to this day...

...her big old body slowly stopped shiverin' and her breathin' calmed and before I knew what was happenin' I figured she was asleep...

"You awake Nan?" I whispered.

...but she was snorin' gentle and calm. Not like a chainsaw or nothin' gross... just like an old lady'd snore...

I reckon I prayed then... for the first time... thankin' god for this wonderful turn of events. It was fuckin' heaven Howard. My cock was buried up to the hilt between my nan's big soft butt cheeks. My grandmother's pussy was right there...

...I ran my hand down her side and felt the hem of her nightie bunched up high up on her hip...

...and a bit further down 'er leg... 'er bare flesh...

...she didn't react at all.

"Gran?" I whispered. Nuthin'.

"Gran!" I go a bit louder...

...and still nuthin'...

...I arched my back away a little, changing the angle so my cock was aimed more upwards...

She don't seem to notice Howie. If anything she snuggled back harder against me...

...I started pushin' up into her...

...more and slowly more... deeper and deeper between her immense fat butt cheeks...

...I couldn't help myself Howie! I was shaking with excitement. I wasn't even sure where my cock was headin' but her lovely big bum was so soft 'n' round. It was like I was already fucking her...