tagIncest/TabooGrowing Sissy's on Granny's Farm

Growing Sissy's on Granny's Farm


Thank you loyal followers and welcome new readers. If you like what you read please VOTE and COMMENT. I love to know the stories are appreciated. In this story the hero experiments with his sexual identity and there are also 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.


Growing sissy's on Granny's farm

A horny young man, his lewd grandmother and becoming a girl

Ronald loved the farm. As a city boy, living in a high rise with his mom and sisters, holidays at gran's place in the country were magical. It was like his very own personal theme park.

It was a proper working farm. Hundreds of acres of paddocks with outhouses and machinery, horses and cattle and sheep and workers doing their work including his grandmother. She worked in the big house.

It was more like a mansion then a house, with miles of corridors and dozens and dozens of empty rooms for a young man to explore. It was so big that their pokey little flat in the city would easily have fitted into a small section of the east wing. There were two enormous sprawling levels. It was big enough for a small army.

The Blackmore family had been living there for a hundred of year but there was only one left now. Mortimer Blackmore was a reclusive man. In all the years his family had stayed in that house Ronald had never seen him, not once. Gran didn't talk about him much except to say he had business concerns overseas, so he was often not there.

Elusive he may have been, but he was generous. He allowed Ronald's family to stay whenever they wanted so he couldn't have been all bad. They'd been spending Christmas and New Year with nan for as long as the boy could remember.

Ronald and his family stayed under Mr. Blackmore's roof in the servants' wing. He had his own room and so did his mother. His stupid sisters shared even though they could easily have had rooms of their own. The family had their own kitchen and bathrooms as well. It was like a hotel.

It was just fine with Ronald. The twelve week school holiday was just barely long enough for the boy and he didn't care if his sisters got bored. They just couldn't see how good it was.

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He found the abandoned office in the barn when he was twelve.

Climbing around in the rafters of the historic old building he came across the little room up above the hay bale stack. Back in the day hay must have just about filled the whole barn and would have been stacked up almost to the ceiling but these days there was hardly any need for fodder. The barn was used mostly to park machinery, tractors and trucks and the big combine harvester.

A hundred years ago there had probably been stairs up to it but they had been removed. The only way up to his new hideout now was a rickety old ladder that was nailed to the wall of the barn.

His little hideout was perfect. It was full of pigeon poop and cobwebs so he knew nobody had been there for ages... years... maybe decades. It had a proper door that closed and glass louver windows across the back wall. There was furniture as well - a big old timber desk and an old-fashioned wooden office chair that swiveled.

It immediately became Ronald's base of operations. For the next several years it became the offices of Julius Marlow, Private Eye. They were also the bridge of Captain Blood's pirate ship, a smugglers hideout and a spaceship enroute to Alpha-century.

But boys grow up. By the time he turned eighteen it became the best possible place to jerk off. His big pile of comic books was pushed aside and replaced with back issues of Harpers Bazaar and Cosmopolitan and his most prized possession - a big glossy porn mag called Busty Mature Babes.

So Ronald discovered the joys of masturbation. His adventurous sojourns around the farm turned into hours and hours of edging his magnificent huge cock. He would strip off all his cloths, lay the thick glossy porno on the desk and jerk off with two hands, staring at the pictorial stories and imagining the things he would like to do to those big busty women.

He was always careful to spray his seed well away from the glossy pages. There were already several spreads irretrievably stuck together when he found it in the pump shed where some cowboy had left it. He wasn't going to make that mistake.

One day he was looking at the one with the big breasted, fat assed old woman who was stripping off to have a bath. This has always been a particular favorite.

His hand started moving up and down the shaft of his huge cock, enjoying that wonderful preliminary tingle.

Ronald was not a big boy by any means. That is to say he was not tall. His mom said he still had some serious growing to do, up and out and assured her son that his father had been small and slight at his age as well.

Ronald had appreciated her kindness but his mom didn't know that his cock was disproportionately large. Any feeling of inadequacy the little fellow felt immediately vanished when he considered his massive dong standing up so hard and proud - like a baby's arm... with the hand held in a fist!

He flicked the page to where the old lady was lying in the tub submerged in bubbles. The woman's huge tits floated on top as did her big round belly and thighs.

For the first time he noticed she had big stacked up piles of white hair tied up in a bun just like gran wore it... and it was silver gray just like grandma's...

With a gasp of shock he realized why he liked these pages so much. His grandmother was older but there were so many similarities...

He studied the model's features closely. She had the same round face and rosy cheeks. Her saggy neck and the laugh lines around her eyes and mouth were just like his gran.

And her body as well...

He flicked the page to where the model had stepped out of the bath and was drying herself, wiping the bubbles off her huge balloon shaped boobs with a big fluffy white towel.

"Ohhh gran..." he murmured imagining the voluptuous body superimposed on his grandmother.

Just thinking about it being her almost made him blow his load.

The old plump woman had her back to the camera with one delicate foot up on the edge of the tub. She was wiping bubbles off her shin, bending over so her magnificent big ass was spread and he could see the curly gray pubic hair around her big gaping pussy and her dark mysterious asshole. Her big thick legs and large protruding bum were just like his grandma.

"Oh fuck gran, oh fuck gran..." he groaned pounding his meat. He could feel himself about to cum, fucking his gran...

Flick the page again to the voluptuous old model pinching a big hard nipple and rubbing her pussy...

"OOoo gran... ohhhh fuck gran... I'm F... FUCKING YOUUU...

Cum squirted out of his cock for the fourth time that morning, cum gushing out from that inexhaustible reservoir that young men seem to have. Great big white ropes of the stuff jetted out like a firehouse. For the first time he broke his cardinal rule and directed it all over the women's picture.

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


Even though she was overweight, years of hard work had left Carolline Woodgrove a healthy, vital woman, especially for someone well into her 70's. Her loose tuck-shop lady arms and thick thighs disguised real muscle and she was still pretty flexible for an old girl, bending down to the dishwasher or stretching up to high cupboards without too much trouble.

She needed to be. It was a big house and she had so much to do.

Since the revelation he'd had about his nan, Ronald had started wondering around after her like a lost puppy. He watched the way her big body moved, fantasizing about the things he'd like to do to her.

Her clothing was simple work-ware, perfect for chores she did around the big house but also amazingly revealing to the horny young man with the perpetual boner in his pants.

The simple cotton-Lycra sweatpants she always wore came in lots of different colors - bottle green, burnt orange, lemon yellow - but all were old as the hills, thin and pilling.

They must have fitted her at some time in the past but even then they would have been tight. Now they clung to her like sarin wrap, the soft fabric disappearing inside the deep inviting cleft between her huge protruding bum cheeks.

She wore the simple elastic waisted sweats high up over the bulge of her plump belly. If he followed the curve over her stomach, down her abdomen and between her legs he could see a furrow - a valley where the tight elastic was riding up inside her pussy.

On top she usually wore t-shirts. Some had prints on them like the big yellow smiley face or 'I heart NY' and so on. These were very cute but the ones Ronald really liked were the plain dark colors with the low scoop neck. They showed off her lovely deep cleavage and, as she never ever seemed to wear a bra her huge turgid nipples were outlined in sharp relief.

Unfortunately, his grandmother hardly ever wore her maids' outfit. He figured that Mr. Blackmore was a country man who didn't see the need for uniforms. When he asked about it, she promised she'd put it on sometime so he could see how it looked. "It's a bit tight in places but I can still wiggle in to it," she laughingly told him.

It was obvious to everyone that gran loved him the most. She had lots of grandchildren and she loved them all, but Ronald knew he had a special place in her heart.

The intensely warm hearted old woman had always singled him out for her special attention - to the delight of his two sisters who teased him mercilessly. Never within anyone's earshot of course.

"Granny loves Ronald, granny loves Ronald." "You're going to marry grandma aren't you?"

When he was a very little boy he had hated granny's kisses and hugs though he put up with them. Even then he realized how much he meant to her. He would wait till he was on his own in the bathroom or in bed before he scrubbed her lipstick off his cheeks.

For her part, Carolline had always thought he was so adorable to put up with her over the top attention. It just made her want to squeeze him and kiss him all the more.

It was such a pleasant surprise when he started squeezing back.

'My little boy must be growing up,' she thought happily to herself. 'He finally wants to spend some time with his old granny.'

He was talking more as well, following her around, chatting about all sorts of things as he helped with her chores.

The long days of the school holiday break whisked by with her new companion. He helped her in the vegetable garden, he helped with cooking, washing and drying, folding clothes in the laundry... and dusting. All the blessed dusting.

Every little job she did he was there to help and, because Ronald seemed to really appreciate her big hugs and kisses now, she got into the habit of thanking him and praising his efforts.

The simplest tasks would win him a kiss and a squeeze and because he returned her affection Carolline found herself happily bestowing more and more of her love on him from her endless supply. Only if they were on their own of course. Subconsciously she knew something had changed in her young man's life.

"Thank you for doing that dear," she'd say and clap him to her voluminous chest.

His diminutive height put him right at eye level with her huge tits and, if there was no one else around, she would allow him to bury his face right down inside her cleavage, his hot cheeks pressed between those big soft mountains of flesh.

His desire surprised her at first but it was very pleasant. These special cuddles could go on for minutes. She would feel his hot breath on her chest and his arms around her waist. More and more he was rubbing her back as well, and sometimes his hands seemed to stray down over her big behind. He must have been doing this accidentally but it sure did feel nice...

"What a good boy you are..." she'd say.

As the weeks progressed Carolline found herself accommodating his innocent fumbling more and more. Ronald was becoming as tactile as she was and while some of his groping was a little inappropriate she would never have wanted him to feel embarrassed. If her handsome young grandson wanted to touch her that was just fine with her.

She just made sure that they were alone when he fondled her breast or stroked her big fat ass. It was so very nice.

Their goodnight kiss was the same. She knew he used to endure the quick peck on the lips she stole before bed every night. Now their evening kiss was becoming more and more lingering.

Worrying that Ronald's new affection for her was being noticed by his mother, she carefully kept his nighttime kiss to the bare minimum, pulling away if it lasted too long.

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


One night when Ronald was on his way to the toilet he found his granny standing behind her partially closed bedroom doorway. Putting her pointer finger to her lips she beckoned him closer. When he obliged, she let him in and closed the door behind him.

"I know you like to give me a goodnight kiss Ronnie dear," she said taking the boy in her arms. "I love that you do dear..."

Ronald immediately thought 'I've gone too far. "I'm really sorry gran," he started. "I didn't mean to upset you..."

His granny laughed and squeezed him tightly.

"No, no you silly boy. I was just going to say that the others would not understand."

They held each other very close, the old woman in her ankle length nightly that clung too tightly on her rubenesque frame and the boy in his pajamas.

"And I love it too dear" she said softly.

Ronald looked up at his grandmother's sweet round old face and before he really knew what was happening, she bent down and kissed him long and hard on the lips.

"There," she said huskily. "What could possibly be the problem with that..?"

"N... nothing at all gran," he stammered. "Nothing at all."

"...so if you want a proper kiss goodnight from your nan, you can just sneak in here when they've all gone to bed," she said in her matter-of-fact way. "It can be our little secret."

The lovely old women ignored his hands on her ass. She stroked his hair as he kissed her neck. She pretended not to notice that his huge erect cock had pooped through the fly of his pajama pants and was nuzzling into her pale blue floral nightie - the massive purple head pressing against her crotch.

She just pretended it was all normal affection, convincing herself there was nothing going on that was inappropriate. 'Simple biological impulses' she said to herself.

That night Carolline Woodgrove went to bed with a pleasant tingle, a breathless kind of excitement that made her stomach flutter. 'He really is the most dear boy,' she thought to herself.

When she realized she'd read the same page of her novel three times she set it aside. Unsurprisingly, Carolline found her pussy wet and responsive to her fingers and within a few short minutes she was gasping in the throes of a powerful orgasm. Masturbation was certainly not unusual for the lusty old woman but using her young grandson as the catalyst was.

Ronald's reaction was much more predictable. He closed the door to his room, discarded his cloths in midair and jumped naked onto his bed. With his knees up and spread apart he used both hands on his foot long tool.

The opening of his cock was only inches from his face when the cum squirted out. It went everywhere - over his forehead and through his thick brown hair, into his eyes and nose but mostly into his open mouth. He swallowed it and gagged on it as it dribbled down his chin.

"Ohhh gran," he sighed.

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


On Sunday everyone went to church. Ronald knew how much his gran looked forward to the singing and getting dressed up in... well, her Sunday Best. His mother went because gran went. Ronald and his sisters went because their mom told them to.

This week Ronald didn't go. He had some things he wanted to do.

His claim of a sore stomach drew some skeptical looks but he stuck to his guns and finally his mother approved it. He was to stay in bed and rest.

At 7am that morning all the women clambered into Carolline's old Mercedes and, with his gran at the wheel, headed off for the two-hour drive into town.

Ronald was completely alone in the house.

There was literally nobody for miles. Even the half dozen cowboys who had nowhere else to be were bunked down in the shearer's shed on the other side of the farm.

The young man would be completely free to do anything he wanted till midday at the earliest... make it 11am to be on the safe side.

His heart was pounding as he made his way to his grandmothers' bedroom. Just being in there made him horny. He stood in the doorway and stripped out of his cloths, dropping his shorts and shirt in a pile on the floral carpet.

Her bed was springy and plush. A memory of Goldilocks and the Three Bears came back to him... 'and the bed in the middle was just right'. Her pillows smelt of her, lavender and soap.

From where he lay, he could see his naked body reflected in the big hanging mirror on the wall. A slight young man, flushed and wide eyed with a magnificent erection sprouting out of his lap.

His eyes fell on her white timber dressing table, covered with his gran's beauty products; brushes, combs, creams and cotton buds... He sat his bare ass down on the little white cushioned stool and rifled through her personal belongings.

He found the top drawer had her lingerie in it. Desperately excited he rummaged through the satin slips, chemises, corsets and big bulky bloomers. A silky black petticoat caught his eye and he pulled it out.

The lustrous sheer material was cool and sensual like cold running water. He rubbed it over his face like a towel, breathing deeply and smelling his nan.

Clambering to his feet he held the sexy nightdress up in front of himself, studying his reflection in the long mirror on the wall.

On an impulse he slipped it over his head.

It looked obscene. The frilly black shoulder straps held it up over his skinny frame but the bra cups had never held less. He rectified this in the way that flat chested girls have done for centuries. Granny's box of tissues was empty by the time he had given himself some decent boobs.

Now when he looked in the mirror he really was starting to look good. His youthful features looked almost feminine except...

Gran's lipstick and blush provided the perfect finishing touch. In a few minutes he had applied the makeup. It was rough and ready but Ronald thought he looked beautiful.

He held his colossal cock through the silky fabric and jerked off. The smooth satin felt cool on his big hot knob.

In the corner of his eye, he saw her washing basket.

Shaking with excitement he fell to his knees and dug through her dirty washing until he found a pair of powder blue knickers. He stretched them out to see how big they were, before burying his face in them.

"Oh god grannn..." he moaned.

Her strong pungent scent had him gasping with lust.

He lay back down on her bed, his head on her pillow and jerked his gigantic cock - his granny's soiled underwear draped over his face.

Ronald was so excited it was questionable whether he would have stopped even if he'd known someone was watching him.

Being where he was, wearing what he was wearing, her makeup on his lips and cheeks and smelling her rose scent everywhere, drove him to actions he had not considered before.

A few years ago, the young man had realized he could suck his own cock. At the time he'd been fascinated and repulsed. He had held the gigantic thing up close to his face and saw he could easily put it in his mouth if he chose to. He held it against his cheek but, at the time, that was as far as it went. He'd filed the information away like an interesting factoid. He wasn't gay so why would he want to do that? His hands felt just fine.

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bypeteh57© 12 comments/ 43727 views/ 48 favorites

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