Growing Sissy's on Granny's Farm Ch. 02

Story Info
The teenager's mentor shows Ronald exactly what is expected of him.
12.7k words
4.6
57.7k
45

Part 2 of the 3 part series

Updated 06/09/2023
Created 01/26/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
peteh57
peteh57
767 Followers

In this continuing story, the hero descends (or ascends depending on your point of view) into the world of highly sexualized cross dressing with strong incest themes. If this doesn't appeal this story will not be for you. All the characters are over the age of 18 years old. All players are consenting adults.

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

THE SPIN-CYCLE

At about the same time as Mortimer Blackmore was filling Ronald's ass with cum, his grandmother, Carolline Woodgrove, was down in the laundry doing a load of washing, waiting patiently for the spin-cycle to start.

Her sex life had been revitalized since she's started fucking Ronald. Her normally neglected pussy was always tingling these days.

Every night he would steal into her bedroom for a goodnight kiss that would lead to more. They fucked each other like animals, unable to get enough of each other.

Whenever she stopped for a second she could relive an episode in detail - her handsome young grandson plowing into her cunt. Carolline's big meaty pussy would get wet and she would often catch herself absently rubbing her hypersensitive twat.

Right now he was particularly vivid in her mind's eye.

The laundry was the perfect place to relieve herself, and still get some work done. Separate from the rest of the house it was a cool retreat that nobody but her ever went to. Nobody but her ever did the washing.

It was a little room with a smooth concrete floor, rough brick walls and a small window that looked out at the clothesline. The only furniture was a low timber stool, a concrete sink, and the big old Whirlpool washing machine.

The old plump woman rested her hand on the rusty steel lid feeling the slow tingling pulse of the 'prewash'.

'Nearly ready', she thought happily.

Carolline loved the old washing machine. She had thrown in a big load of dirty workwear, putting the machine on the longest cycle. When she pressed 'start' she knew just how long she had before the 'spin-cycle' started.

There was no need to take her leggings off. She wasn't wearing any underwear and the old blue cotton tights she wore hugged her like a second skin. She simply pulled them up higher on her waist. The faded pale blue material rode up even further into ass and spit her prominent meaty pussy in two.

She may as well have been naked. Even her big hard clitoris was outlined in relief. She brushed her fingers back and forth over the sensitive nub, teasing herself, shuddering in anticipation.

A wet stain began to spread out along the crack made by the lips of her vulva.

With her hand on the lid of the washer, she gauged the rhythms of the clunky old machine, looking out the window and letting her thoughts relive the wonderful times she'd been having with Ronald's mammoth dong.

'Lord I do love that boys cock', she thought to herself.

Carolline's fingers probed the dampening cleft between her legs, rubbing the thin pilled material over and into her cunt. Her receptive pussy tingled as she ministered to herself, daydreaming of Ronald's cock. Her little round spectacles started to fog up.

She was three-quarters of the way there and when the machine started to 'wash'.

"Mmmm... good... yesss..." she sighed aloud over the 'chunka', 'chunka', 'chunka' churning sound. Now was the time.

With legs apart on either side of the washing machine's rounded corners, she spread herself over the top of the big old machine, holding her hot meaty cunt up against the smooth vibrating metal; chunka, chunka, chunka...

This old rustbucket washer was definitely on its last legs, noisily bouncing and shaking as it did its job. It was perfect for Carolline. She used it like a familiar lover who knew what to do to get her off.

With one leg on the floor the other on the little stool she lay down over the white tin top and held onto the raised control button display at the back.

In this position, she could tease herself to the end and cum when the spin-cycle made the machine jump around like some sort of mad robot...

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

Meanwhile, Ronald was looking for his granny.

The young man had been in a daze since the morning's episode with Mortimer Blackmore. The degenerate man had used him like a cheap whore. Ronald's violated ass was still tingling and sore from where his 'master' had reamed him, fucking his virgin ass and cumming inside him. Every now and again a dollop of Mortimer's cum would dribble out.

The poor conflicted teen was so unsure of himself. Not only had he enjoyed having Mortimer's big cock in his ass, but he also couldn't wait for the next time. 'Am I gay or straight or what?', he wondered.

His granny would make him feel better. 'I'm going to tell her all about it' he thought to himself.

He looked for her in all the normal places in the house and then around the grounds. He was about to give up when he heard the washing machine as he was walking past the laundry.

His gran would have never thought to lock the door - nobody but her ever did washing after all - so that was how Ronald found her, holding on to the big white washer like it was her lover. She was spread eagle over the madly whirring machine, her huge fat ass swaying provocatively back and forth as she humped her cunt against the intense vibrations.

The crazed old woman was too far gone to notice the object of her fantasies quietly sneaking up behind her. She was holding on for dear life as the broken old machine was jumped about, banging against the wall.

He stood silently behind his grandmother's huge ass that was spread wide and rearing up in front of him. He could hear her mumbling as she fantasized about him, "Oh yes Ronnie... fuck your granny... fuck me with your lovely big cock..."

Her leggings were so tight they outlined the valleys between her prominent mons and the cleft in between were the elastic fabric had disappeared completely up inside her cunt. Her juices were saturating the cotton and a large wet patch was spreading out over the fabric that was wedged up inside her pussy.

It was too much for the conflicted boy. Pulling his pants down around his knees, Ronald's cock sprang out in front of him like a big thick spear.

The shock when she felt someone on top of her made Carolline scream...

"WHAT... STOP... STOP..."

Whoever it was holding her down painfully. She could feel frenzied hands forcing their way into her tights and groping her ass.

'It's one of the workers', she thought desperately.

The farm was so far from civilization that the cowboys and farmhands often stayed on the property for months at a time. It was too far to go into the little town and there was nothing to do there when they arrived. Most of the men figured it was better to save your money and splurge big on your leave.

Unfortunately, after a while, their repressed libidos spilled over. When jerking off no longer worked the horny cowpokes started fighting. After that, they either gave notice and left or they resorted to each other, handjobs, cocksucking and then buggery, in that order.

And then there was rape. Rare but it happened. Several of the maids had been assaulted over the years.

"P... please... there's n... no need for this," she begged. "If you leave now I won't turn around... I... I... won't see who you are..."

Psychologists and police detectives call Ronald's behavior, 'temporary insanity', the moment when the perpetrator loses all sense of right and wrong. All the boy wanted was to fuck her ass like his master had done to him.

As his beloved grandmother begged, he leaned all his weight on her back and roughly reefed her stretchy cotton tights down around her thighs. Her huge ass glowed white in the dim light ...her asshole winking at him as his nan squeezed and released her pelvic floor...

Shaking with lust the teenager groped her sopping wet cunt. He played his fingers over the damp pubic hair and delved roughly inside her.

"AAHHH... NO NO, NO STOP STOP... AHHHH HELP ME AHHHH..."

The old whore's pussy was sodden and his hand slid easily up inside, his fingers, his knuckles and then his whole hand. He started to fuck her, fisting her huge inflamed cunt.

"PLEASE AHHHH... NO... no... no... ... ...nooo... oooo... ooo..."

If he'd let her know it was him she would have stopped struggling immediately but he didn't want to. Her fear was driving the young man crazy with lust.

His hand came out glistening, literally dripping with her juices. The crazy teenager spread the syrupy liquid up over her puckering asshole, lubricating her...

"OOOOHH NOOOooo..." she moaned. "What are you doooing...? even though she knew all too well what was coming.

Ignoring his grandmother's terror, Ronald put his huge cock up against her sphincter and roughly pushed his mammoth cockhead into her asshole...

"Stoppp... mmm... Oh nooo..." she sobbed.

Inch by grinding inch he pushed deeper and deeper inside her until his gigantic cock was balls deep in her bum.

Slowly ...all the way out. And all the way in. All the way out... and all the way in...

Despite her revulsion at being attacked her cries of distress quietened down. She stopped struggling and lay quietly as the rapist pushed his huge cock inside her anus. 'No need to fight now', she thought pragmatically. 'The monster is going to do it anyway...'

To her surprise and disgust with herself, she began to find herself fascinated by the ordeal, especially as the invasion into her asshole was tempered by the grinding pulse of the old washing machine. Like a considerate lover, it was tickling her clit perfectly, balancing out the invasion of her anus with insistent pleasurable vibrations.

As boys magic knob did its work she began to feel desperately excited.

Biting her lip hard she tried to muffle a groan of pleasure. The last thing she wanted was to encourage him.

"MMfff..."

Faster now. All the way out... all the way in... all out... all in ...out... in... out... in.. out... in...

The rapist grabbed the fat around Carolline's wide hips and started pounding into her ass as the 'spin-cycle' started.

To Ronald's immense surprise the old woman cried out in unbridled passion.

"Mmmffff...mmmm... mmmMMMM, MMM OOOOOOH YESSS, YESSS YESSS

Like her grandson earlier in the day she gave herself over to the feeling - the crazy spinning machine vibrating madly against her hypersensitive clit and the rapist's huge tool hammering her ass.

"OH MY GOD... OH MY GOD... " she screamed.

She felt her attacker tense and silently cum, shaking as his seed poured into her. Even as he was shooting a huge load into her bowel, a massive orgasm racked her body.

"OH MY GOD... AAAAHHHHHH, AAAAAAHHHHHH... AHHHHH... oooooo..."

The rapist bucked in and out of her bum like a rodeo rider and she felt his jitze running out and down onto her hot spasming cunt like a cool river.

As he withdrew his spent cock, the spin-cycle ended. Carolline lay where she was... panting and dizzy. Spots played before her eyes like a crazy interpretive dance.

She was afraid to turn.

Then there were hands on her, suddenly gentle.

"You liked that gran, didn't ya?" asked the boy apprehensively, stroking his granny's bottom. "Did yu know it was me?"

To exhausted and post-orgasmic to be angry she just sighed. Panting for breath the old woman could barely put words together.

'Goodness Ronald I was so frightened," she gasped, trying to sound cranky. "I'm old for goodness sake... if I'd realized it was you..."

"I'm sorry nan..."

"You'll be the death of me you know..." she said as her poor old heart began to beat in a more normal rhythm.

"I'm sorry nan, I'm really, really sorry. I don't know what came over me... seeing you like this, spread out... I just lost my mind..."

The fat old woman slowly slid down off the now silent washing machine. Pulling her tights back up over her abused ass and plump belly, Carolline turned to her handsome grandson. She did love the way he enjoyed her body. 'He's such a good lover', she thought proudly. Ronald looked so terribly contrite and forlorn that a smile came unbidden to her lips.

Taking him in her arms, she kissed him deeply. "You may be the death of me young man," she said when she caught her breath. "But what a way to go..."

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

A PRETTY PINK DRESS

Always on the horizon was his next meetup with Mr. Blackmore. Ronald was seriously frightened but excited as well, feeling like he'd dodged a bullet last time and was tempting fate by going back again.

Scared as he was he knew he had to go. His master had pictures of Ronald doing ... stuff. The idea that his gran, his mom, and his sisters would see him like that made him feel sick.

On Thursday morning he made his way to the special locked room. The window was still unlocked and he hoisted himself up and in.

It was as they'd left it. The canvas sheets on the ground, the big bare mattress on the romantic canopy bed, the chair Mr. Blackmore had sat on.

Ronald knew he would need to call his master to let him know he'd arrived.

He opened the wardrobe door where the beaten tin cover covered the peephole into his gran's bedroom. Below it, splattered all over the dark timber panels, he noticed ribbons of dried cum, some yellow with age, some more recent, all evidence of Mortimer Blackmore's visits.

'He probably watches nan and me fucking every night' he thought, 'jerking off his big cock as I fuck her...'

Imagining the depraved man watching him made Ronald shiver and his cock twitched involuntarily.

He slid the peephole cover-up and looked into his grannies bedroom and the bed where they fucked...

Down on the dusty floor, the old Bakelite phone was still sitting in the shadows waiting for him. 'There's no point putting it off', he sighed.

Kneeling down he put his shaking finger in the 1 hole and dialed.

Like before, it rang and rang and rang.

Mr. Blackmore wasn't there but Ronald knew he would soon hear the key in the lock. He was about to hang up when, to his surprise, someone picked up.

"Hello there Ronald," crackled Mortimer's voice on the old phone. " I've been a little delayed I'm afraid my boy... but I will be there...soon... very soon."

"Yes, si...master"

"Ha... very good," chortled Mortimer. "You are a good boy... yes... very good. I have a present for you. Under the bed... in a big box with a bow..."

He hung up.

The boy was young enough to still get excited by the idea of gifts. He scrambled to the bed and looked under. There in the dust and mouse droppings was a large flat lavender colored box tied with a huge pink bow. Excited despite his situation Ronald pulled it out and put it up on the bed.

There was a card tucked under the pink ribbon with a picture on the front of a couple walking on the beach at dusk, their hands around each other's waist, silhouetted against the sunset.

It simply said:

I hope you like it, dear boy.

Mortimer

Ronald untied the bow, lifted the lid, and unfolded the tissue paper that covered...

"Oh god," he whispered as he carefully picked up the party dress.

It was pretty and pink and looked like something his sisters would have worn when they were twelve, or Sailor Moon maybe.

"He has got to be kidding..."

There were short puff sleeves and a white lacy brocade around the flared hem. The pattern was pale pink and white candy stripes with red strawberries and little greenish-blue birds scattered about.

"I'm not wearin' that," he said dismissively and threw it aside.

In the bottom of the box, there were lacy white knickers as well, a pink garter belt with black fishnet stockings... and a bra, lacy and white like the panties but thickly padded. He found silicone implants had been stitched into the cups.

'He wants me to look like I've got boobs', he thought, shaking his head, fingering the beautiful delicate lace. 'I'd look ridiculous...'

The last thing in the box was a pair of soft black leather slippers, like moccasins.

Ronald contemplated the beautiful costume, his misgivings fading. His cock was hard and he found he was breathing heavily.

"What the hell," he said aloud as he stripped out of his clothes.

The bra and panties were easy, though getting his erect cock to stay tucked inside the frilly little panties was tricky. It stretched them out to breaking point and then poked out over the top of the waist elastic.

'Nor meant for cock', he thought with a smile.

The pretty little lollipop dress simply slipped over his head.

The stockings were a bit more tricky. First, he had to figure them out. He'd seen enough pictures to have a reasonable idea. He slipped the stockings over his feet like socks... long socks that kept rolling up his legs.

The garters went around each thigh easily enough but when it came to attaching the straps to the hose... he was beaten. It took ages - taking them off, putting them back on...

Finally, he had it. The sheer black satin looked good and felt terrific and the little black slippers fitted like a glove.

Turning to the wardrobe mirror he surveyed the result and gasped out loud at the beautiful feminine boy reflected in the mirror. Even his thick brown hair didn't detract. 'Lots of girls have hair like this', he thought to himself.

He tried a few 'Vogue' poses - lifting his skirt up to show his thigh, pursing and pouting his lips, or bending over to flash his 'cleavage', blowing a kiss like Marilyn Munroe.

His legs looked fantastic in the black fishnets. The black thigh garters made the innocent little girl dress look quite the opposite.

Ronald slowly lifted the hem of the pink and white candy strip skirt up further and further to look at how his mammoth cock looked in the ridiculous little white knickers.

Thankfully they stretched. They seemed to hold their own. His gigantic cock was putting stresses on the elastic that their specifications had not allowed for. He had dressed his huge dick to the left across his stomach, the big purple head looking over the top of the frilly panties as if to say 'get me out of here!'

He tried to put it back in but found himself rubbing it instead and that was how Mortimer found him.

As soon as he heard the key in the lock he dropped his dress over his manhood and turned to the door. Despite his misgivings, Ronald was excited to see his masters reaction.

Mortimer Blackmore stepped inside, closing the door behind him.

He looked just the same to Ronald, a handsome decadent villain. He wore the same sensual robe, with its big hip pockets where he kept his pipe and other secrets.

He was also holding a large brown paper bag.

Ronald stood quietly, standing demurely in front of him, his hands clasped together behind his back, waiting pensively for his master's verdict.

Mortimer inspected him. His big twirly mustache twitched up and down as he studied the boy.

"Don't you look lovely," he said huskily. "Almost perfect... but not quite... not your fault boy...

Mortimer fished around in his bottomless pocket and came up with a lipstick. Stepping in close he held Ronald's chin carefully as he applied it. "Good... yes... very good. Maybe a little blush..." Again he dug around and a little compact appeared. 'Just like gran's', Ronald thought.

Mortimer took his time applying the rouge to the boy's cheekbones. "Almost perfect... almost..." he muttered in Ronald's ear. "One last touch I think..."

Mr. Blackmore retrieved the large brown paper bag.

"I believe you should close your eyes... for this last bit boy," he said, obviously enjoying the theatrics. "Closed?... yes? ...good..."

He did as instructed as Mortimer rustled about. Ronald felt him close in front of him and then something on his head...

"Keep em closed boy... yes, yes... lovely."

peteh57
peteh57
767 Followers