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Author Topic: Timmy - A good little sissy  (Read 31743 times)

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Harrietmarwood

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Timmy - A good little sissy
« on: March 13, 2016, 11:14:50 AM »
It was a regular Tuesday morning and Timmy Lovell awoke to the sound of
Harriet readying things in the bathroom while humming to herself.  He felt
a shiver travelling down through his spine at the thought of the morning
proceedings he would have to endure, and yet his small pen-is was rapidly
engorging, pressing firmly against the soft fabric of his cloth nappy.

   Although Timmy was almost thirteen now, his foster mother still kept him
on a strict hygienic regimen with very little consideration for the poor
boy's modesty.  This had been the way ever since Timmy came to stay with
Harriet about two years ago.  As most boys of that age, Timmy was very self
conscious about his body - especially his backside which unfortunately
always seemed to be at the center of attention in this household.  But no
matter how much the boy pleaded, Harriet would always reply in the same
fashion:

   "Little sissy boys can't be trusted with cleaning themselves properly"

   It certainly didn't improve Timmy's case that he had begun wetting his bed every night, like an incontinent toddler.

Harriet would often remind him how much labor his childish
constitution made her go through, although in truth it seemed that she was
taking an inappropriate amount of pleasure from her many administrations of
him.

   Timmy was a very handsome boy, having inherited the beauty of his
long-lost mother, with soft, boyishly feminine features,
complemented by a deep hazelnut warmth protruding from his eyes and the
fine locks atop his head. He was small for his age, with a frail built that often lead people to mistake him for a younger boy.

   Harriet herself was an attractive middle-aged woman with
voluptuous feminine curves.  Her features were beautiful, but her face, framed by wavy chestnut hair, carried a majestic look that spoke of domination and a
no-nonsense manner.  Her piercing green eyes and full red lips added the
hint of sex appeal, even with several decades behind her.

   She had always been kind to Timmy, in her own way.  Although stern and
unbending in regards to her many principles, she had a heart as large as
her bosom, and those deserving of it were never in dire need of care in her
presence.  She was a tall and well-built woman, and Timmy always felt
powerless and insignificant when she towered over him, the great twin
globes of her chest symbolizing her maternal authority over him.

   He loved her; that she knew.  She couldn't mistake the look of utter
devotion and supplication in his eyes - even when sheltered in a grimace of
scarlet coyness and embarrassment.  No matter what her wicked mind decided
to do with his body, his protests were never more than a timid whimper.
Not that he was in a position to resist her anyway, as she would simply
drag his lithe body across her firm lap and punish him until he was sobbing and his poor bottom was glowing bright red.

   Timmy pretended to be asleep as Harriet entered the room, dressed in a
soft cashmere sweater and attractive patterned skirt, and crouched down
beside his bed.

   "Good morning sweetie.  Did you sleep well?" She whispered while running
her fingers soothingly through his hair.

   "Yes mommy," he answered sleepily.  She insisted that he call her mommy,
even though it made him feel rather silly.

   Harriet slid her hand underneath the covers and trailed her digits
across the soft flesh of his stomach, cupping his modest package on the outside
of his nappy.

   "Did my little prince have an accident?" She asked smiling warmly down at
him.

   "Yes mommy," he whispered with blush.

   "Be a polite little sissy and ask mommy to change your nappy." She reprimanded him while tightening her grip.

   Timmy closed his eyes at the slight pain, gasping,

   "Please mommy."

   She let go and softly padded his small bulge.  "Good boy," She cooed while
bending down and kissing him tenderly on the lips.  She drew back the
covers and positioned herself on the bed between his smooth pale legs.

Slowly, almost methodically, she started to unpin the large safety pins on
either side of the nappy.

   Timmy knew what was expected of him.  He drew back his knees as far as
he could, and laid out his arms flat above his head.  He closed his eyes
and gasped slightly as the cool air of the room came into contact with his
most private parts.  No matter how many times his foster mother would see
him naked it was always like the first time.  Embarrassing and degrading.
Even so he couldn't help his little member from getting painfully erect every time she bared him, thus adding further to his shame.

   Harriet felt almost dizzy with excitement at the sight before her.
Every crevice and surface was completely hairless.  His small pecker
lay pulsating on the flat of his stomach with a single pearl of pre-c-um dropping from the shiny pink glans. Underneath it hung the tiny pink pouch of his testes.

"Tiny and hairless, just like a little sissy" Harriet said sofly, making Timmy whimper pathetically.   

   Harriet opened the top draw of the nightstand which stood beside the
bed. In it lay several different medical articles which were all apart of
Timmy's daily treatment.  She picked up a jar of Vaseline, wet wipes and an
old fashioned rectal thermometer.

   Taking both his slender ankles into the palm of her left hand, she bend
Timmy backwards, raising his bottom from the bed.

Timmy felt utterly degraded, as she spread him open like a small child.

Removing the damp diaper from underneath him, Harriet continued to wipe him down. "Let's get you nice and clean".

The boy stared helplessly up at the cartoon prints on the ceiling, trying to escape the reality of the situation.

   "What an adorable little bottom," Harriet remarked while tracing a long finger down the cleft of his cheeks, stopping right at the edge of his tiny pink
rosebud.  She then dipped her finger into the Vaseline and carefully rubbed
the sticky substance around his puckered opening.

   "Uhhhhhhhhhhh" Timmy whimpered quietly.

   Harriet would often marvel at just how sensitive the boy's anus was.  He
was the perfect play-toy in every possible way.

   Slowly she dipped the rather large thermometer into the jar, making sure to
collect as much Vaseline onto the tip as possible.  Looking into his
innocent face, eyes closed, mouth agape, she lined up the thermometer and
proceeded to insert it in one smooth motion.  The whimpers of the boy
fluctuated in accordance with the twirling motion of the thermometer as Harriet rotated it expertly.  She withdrew the thermometer right to the tip, before reinserting it all the way.  She kept
a tight grip on both his ankles, making sure the boy was bend all the way
back.

   Letting go of the thermometer with her one free hand, Harriet patted his smooth genitals, cooing; "Good boy". She could easily fit his entire package inside her palm.

   After a few minutes of patting and twirling, Harriet slowly withdrew the
thermometer and read it closely.

   The boy felt the cool air of the room tickling his glistering sphincter.

   Without commenting further on the reading, Harriet picked up a few wet
wipes from the box.

   "Ohh uhhhhh" the boy moaned as the soft tissue came into contact with
his opening.  Enjoying herself immensely, Harriet attentively wiped the
Vaseline from his bottom.

   The tiny rosebud of flesh recoiled as she teased it mercilessly.  It was
all she could muster not to start playing with his young body right there
and then, but there was work to be done.

   She got up from the bed and helped him to his feet.  Standing unsteadily
before her, blushing, eyes at level with her bosom, she drew him in for a
big hug, pressing the boys face firmly against her cleavage while her hands
roamed freely across his naked back and cheeks, cooing in a soft tone;

   "Are you ready to take your punishment like a good little boy?"

   Timmy looked up at her with pleading puppy-eyes.

   "Please mommy.  I won't forget again"

   "You know better than that Timmy" Harriet said as she sat down on a
straight-backed wooden chair and drew the boy across her lap,
 positioning him to her liking.

   "Such a cute little behind," Harriet repeated in a loving tone as her
hands traveled over his young bum.  She spread his cheeks wide apart with
both hands, enjoying the soft whimpers of embarrassment it caused from the
boy.  Harriet smiled at the thought that his bottom would soon match the
color of his blushing face.  The fact that Timmy was so self-conscious
about his bum made the thrill all for the greater.  The poor boy wanted
nothing more than to cover his pale little fanny, yet he sought so
desperately to please his mommy, that he only mustered a weak whimper as
she exposed and fondled his soft globes.

   Timmy even pushed out his bottom for her, while keeping his eyes tightly
shut in anticipation.

   Harriet took hold of his wrists and held them on the small of his back,
rendering the boy completely helpless while she stroked and squeezed his
naked backside.

   She enjoyed the silence before the storm.  Once in a while she would
stop her fondling and lightly pat his upturned rump, feeling the boy
stiffen in fear.

   Then suddenly, as if like thunder from a clear sky, her hand descended
sharply on the upturned cheeks of his bottom, causing Timmy to yelp out in
pain.

   "Smack!  smack!  smack!" It sounded, as hard slaps rained down upon the
woundable target before her.

   "Please mommy!" Timmy wailed in desperation.

   "Smack!  Smack!  Smack!  Smack!"

   The poor boy wriggled his bottom pathetically in an attempt to lessen
the impact of her flat palm against his skin.

   "Smack!  Smack!  Smack!"

   For the next five minutes, all that could be heard in the large house
was the sound of flesh against flesh as her hand unrelentingly roasted his
poor backside.

   When Harriet was satisfied with the rosy-red color upon his burning
cheeks, she suddenly stopped and ran her hands soothingly over his inflamed
skin.

   "Shhhhh all done now sweetie," she said reassuringly, feeling a rush of
sympathy as she saw the tears streaming down his blushing face.

   She stood the boy up and, placing her hands on his burning cheeks, she
gave him tender kiss on the lips.

   "Do you promise to be obedient now Timmy?" She said, looking into his
tearstained face.

   Timmy tried to speak, but was prevented by the sobs which kept rising to
his throat.  Instead he nodded his head eagerly.

   "Good boy..."

   Timmy was then led by hand towards the large bright bathroom at the end
of the hall, where a steaming brass tub awaited him.  His hard member
bobbed shamefully before him with each step.

   The cool porcelain tiles send shivers up through Timmy's spine as he
stepped into the bathroom.  He was met by a feminine perfumed scent that
for some reason made him feel even more vulnerable, subjugated as he was at
the mercy of the female sex.  The sound of Harriet's footsteps echoed in
the large room as her high heels trod across the shiny white tiled floor.

   She marched Timmy into the middle of the bathroom.

   "Hands on your head now Timmy" Harriet said sternly, watching the boy
obey immediately.

   Scoring her nails gently across his back, she stepped around him towards
the tub and felt the water.

   Turning back to look at him, Harriet found herself once again deeply
stirred by the beauty of his slim body.  Her eyes passed appreciatively
from point to point, dwelling with the art of a connoisseur, first upon his
slender torso and then down onto the straight smooth legs.  His skin was so
delicate, his frame so fragile.

   Timmy could not bring himself to meet her gaze as he stood naked with
his hands placed upon his head.  Harriet stepped towards him slowly, her
hips moving sensually.  Taking hold of the boy's chin she tilted his head
backwards, noting his visibly blushing cheeks.  Harriet looked down into
his innocent eyes, savouring the moment.  Timmy felt so docile and feeble
in her hands, like a puppet on a string.  As she let go of him, his gaze
immediately returned to his feet.

   Taking hold of a fluffy towel Harriet spread it down on the tiled floor.


   "On your back young man," Harriet told him nonchalantly as she busied
herself at the sink.  With a timid whimper Timmy reluctantly lay down on
the towel, feeling the soft fabric against his naked skin.  The boy pressed
his legs tightly together as he watched Harriet turn towards the sink and begin filling up a large, bright red enema bag.  She ran her fingers over a variety of syringes, contemplating,while glancing over at the boy.  She made sure the enema was very soapy and decided on using a rather large syringe.

Harriet kneeled down and took hold of his slender ankles.

   "Arms over your head Sweetie" Harriet said with a faint smile, her eyes
glowing with lust.

   As Timmy complied he felt his legs being lifted up into the air,
elevating his bottom from the soft towel.  Harriet gave a small sigh of
pleasure as she exposed his body so rudely, spreading the milky thighs wide
apart.  With her eyes fixed on the firm and trembling roundness of the
boy's buttocks, she forced his knees down to his chest.

   "Now hug your knees tightly sweetie, and don't let go unless I tell you
so," Harriet said in her clear voice, not for a moment betraying the thrill
she felt as he was made to assume the ultimate of degrading positions for a
young boy.

   "Please mommy" he pleaded, but the look on Harriet's face was that of an
unrelenting and implacable queen as she towered over him.

   Timmy felt absolutely ridiculous as he hugged his knees.  With his
erected pen-is resting on the soft flesh of his stomach and his bottom
pointing straight up towards the gaze of his foster mother, he could not
think of a more humiliating position.  Neither could Harriet.  How
wonderfully exposed and vulnerable - she thought to herself, thrilling to
the idea of his helplessness and her own power; already her own sensuality
was aroused, her cleft had begun to grow deliciously moist.

  Harriet relished in the sight of this beautiful boy so submissively on display.  With his handsome face
blushing deeply and his eyes closed tightly, he looked absolutely adorable.
Timmy was hugging his knees as if his life depended on it, elevating the
cheeks of his bottom, which were a nice shade of pink from the spanking she
had just administered. 

    Timmy's face was a true picture of horror as he saw Harriet
smearing lubricant down the length of a huge nozzle as if it was
a phallus.

   "Please mommy, I don't want an enema" Timmy said barely audible, almost
a whisper.

   In his 'knee to chest' position with his feet dangling in the air,
Timmy's rosebud sphincter seemed to be cringing as it peered up at Harriet.

   Licking her lips, she eased the middle finger of her right hand into the
deep crevice of his plump buttocks and smeared the cold lubricant over his
hot little anus.

   "Oooh!" Timmy moaned.  He began squirming his rear end around.

   "What's wrong, sweetie?" Harriet asked with a slight grin, and although
she had already applied a liberal coating of the lubricant, she didn't stop
rubbing his vulnerable orifice.

   "Just relax your little bottom" Harriet whispered as she began
insinuating the end of her middle finger into the exposed aperture of the
boy's buttonhole.  She felt the tightness of his greased anus engulfing the
first knuckle of her probing finger.  A perverted thrill tingled up her
spine.  She smiled reassuringly at Timmy, as she deftly sank the full
length of her long and slender finger up into the boy's quivering hole.
The inside of his bottom felt hot as his reflex action caused the velvety
anal canal to clamp down around her embedded finger.

   "Uhhhhhh" the boy whimpered, his mouth agape, almost beside himself from
the intense sensation.

   "Just relax, relaaaaaaax," she breathed, "The syringe is much bigger
than my finger and I need your bottom loose and fully open for the nozzle."
She illustrated her point by slipping her finger deep into his quivering
bottom.

   "So don't complain," she said, her voice rich and fruity with excitement
as she gently stroked her cold-creamed finger in and out of the tight ring
of his sphincter.  She felt a shiver of delight between her legs as she
deftly pulled her finger out of the young boy's bottom.  Her action caused
a loud popping sound, as she examined his liberally greased rectum.

   She knelt down alongside the boy and brought the nozzle tip up to his
quivering sphincter.  Timmy flinched and pulled back for a second.  Harriet
giggled and placed a hand on his shoulder.

   "Where do you think you're going?" Harriet said with a wicked smile.
Then she pressed the nozzle against his greased hole and pushed it in.
Timmy whimpered as he felt it enter him.  She slowly penetrated him as far
as she could, his little anus being reluctantly forced to dilate around the
shaft.

   As Harriet released the water, Timmy felt the hot soapy liquid gushing
up inside him, invading his very core.  Harriet laid the palm of her hand
flat on his tummy and began to stroke in a circular motion.  She made sure
that her wrist smoothed over the tip of his pen-is as she caressed his
flesh.

   Pleasure fused through the boy's body, blending with the discomfort in
his guts.  Harriet could feel the hot fluid gathering in his stomach as she
worked the nozzle stem to stimulate his prostate.  A large drop of clear
viscous liquid formed in the eye of his urethra.  It descended in a gooey
silver strand as it dropped onto his stomach.  Harriet noted that half the
content of the enema bag was already inside the boy.

   "Please mommy!" he exclaimed.

   "Shhh...  just a little while longer....  be a good boy, you can take it
all," she comforted him.  Her fingers kneaded his stomach.  His pen-is
throbbed against the back of her hand.  His balls were drawn up tightly
against the root of his pen-is.  The muscles around his anus were
contracting frantically as he fought to stop his body from disgracing him.

   As the bag finally emptied, she slipped the nozzle out and pressed
Timmy's cheeks tightly together to avoid any leakage.

   "You have to wait while it cleanses you.  Just 5 minutes.  Then you can
let it out."

   The minutes passed very slowly.  Timmy squirmed uncomfortably on the
floor.  It was like having to go in the worst way and not being able to.
After what seemed an eternity, Harriet finally spoke.

   "Timmy, I'm going to help you up now but you must try and squeeze your
bottom cheeks together so that you won't dribble."

   Tottering to his feet Timmy stood up with his belly visually distended.
Opening the toilet lid carefully, Harriet positioned Timmy's bottom on the
cool seat.

   "Let it out Timmy," she demanded as she stood over him.

   He didn't have to be told.  The pressure was so overwhelming that Timmy
immediately expelled the contents of his tummy, feeling a great flood of
liquid gush out underneath him.

   Embarrassing farting noises echoed into the toilet as he helplessly
evacuated his bowels.  Timmy shivered involuntarily and hung his head in
shame.  Harriet had him sit a few minutes, waiting for further spurts or
dribbles.  The boy sat there hunched forward on his knees, a pure picture
of shame.  Harriet was enjoying herself immensely as she towered over the
blushing boy.  Placing her hand gently on his cheek, she bent over slightly
and looked into his blushing face.

   "Now turn around and sit backwards on the toilet so I can wipe your
little bottom" Harriet said in a gentle voice as she caressed his cheek.

   Blushing a deep shade a red, Timmy slowly got into position, barely able
to believe how utterly humiliating this was.  Harriet pressed down on his
back making him lean forward, resting his head on the toilet and arching
his back.  Harriet smiled wickedly at her invention as she picked up some
sheets of soft toilet paper and folded it in her hands.  All the soap and
water had left everything clean but she loved how it embarrassed the poor
boy to have his bottom wiped like a small child.  She brought her hand down
between his cheeks and slowly pressed the soft material against his cleft,
splitting his buttocks as she wiped it over his sensitive anus, leaving
only water on the tissue.  Harriet lovingly stroked his back as she
repeated the procedure several times, each time making Timmy whimper as the
tissue touched his opening.

   "Such a naughty little boy.  Getting your bottom wiped by mommy" she
whispered into his ear "Only two more enemas to go now sweetie."

   Timmy looked back at her in disbelief and horror, his lower lip
trembling slightly.

   "Please mommy."

   But nothing could bend the will of this iron lady.  It was a mere ten
minutes later that he stood naked in the bathtub, feeling completely
exhausted and literally drained after receiving three large enemas.

   Harriet placed a stool next to the bathtub and sat down, uttering a
satisfied sigh.

   "Now doesn't it feel nice to know that you are sparkling clean inside
your little bottom?"

   The boy gave a weary, reluctant nod.  Harriet took hold of his hips and
spun him around, able to admire his body at her leisure.  Timmy was like a
rag doll in her hands, too tired to protest as she proceeded to lather up
his body with soap.

   She worked over his arms, back and stomach before skipping down along
his slender calves and up the inside of his thighs, occasionally scraping
the sensitive flesh with her long manicured nails.

   When she reached his mid-region, she pretended to only then notice the
violent erection standing proudly a few inches from her face.

   "Little boys never seem able to control themselves," she said while
shaking her head in disbelief.

   Resting her left hand on his buttock for stabilization, she gently
touched her index finger to the receptive slit of his helmet, making the
boy's knees buckle slightly in response.  Timmy moaned softly as Harriet
moved her foamy palm over the corona, sliding back his foreskin.

   "No fuss now Timmy,"

   She scolded him with a sharp slap on his behind.  Harriet felt her
panties soak in the moisture of her inner folds.  The complete control she
was exerting over the young boy had her mind racing deliriously.

   Taking a soft grip on his rigid little rod, she brought her other hand around
and cupped his delicate jewels.  She began gently soaping up his shaft,
while the fingers of her left hand casually played around with his tight
sack, now and then encircling the base and squeezing together the smooth
grapes within.  With her thumb she began rubbing the underside of his glans
in a small circular motion.

   "Uhhhhhhhhhhhh..." the boy moaned while his knees began to shake beneath
him.

   Sensing that the boy was close, Harriet let go and firmly patted his
scrotum, making Timmy raise to his tiptoes.

   "Uhhhhhhhh"

   Harriet spun him around in the tub.

   "Such a silly boy you are today Timmy.  I Haven't even gotten to your
little fanny yet"

   Harriet punctuated her words by clutching one of his soft globes in each
hand, digging in her long nails.

   Soaping up her hands generously, she commenced to deeply fondle every
crack and cranny of his boyishly perky behind, while constantly whispering
into his ear, purring to him how adorable she found his little tush to be.
Her fingers delved shamelessly into the deep crease of his bottom, locating
his tiny spasming orifice.

   Timmy closed his eyes tightly, as he felt the prying lioness behind him
line up a long soapy finger.

   "Now, be a good boy for me Timmy...  I want you to try and relax your
little hiney - ooops there we go!"

   Harriet cooed triumphantly as her index finger slipped up into him with
little resistance.  An asphyxiated gasp escaped Timmy's lips as she buried
her finger to the knuckle, making the boy jump onto his toes.

   "Stand still, Timmy, or you will be going over my knees with that wet
bottom of yours raised in the air...  would you like that, mmm?"

   "No, mommy" he replied, terrified, forcing himself to remain still while
her fingers worked his tight pliant channel.

   Locating the sensitive flesh of his prostate, Harruet quickly withdrew
her finger before adding a second digit, stretching his tight anus.

   "Uhhhaahhhhh ohhhhh!" Timmy moaned besides himself from the adept and
unrelenting stimulation of his young body.

   She suddenly felt his prostate begin to harden, and in one swift motion
her invading touch slipped from his body.

   "Clean as a whistle!" She ascertained with a sharp slap across his
buttocks "Now sit down and soak in the water.  I'll be back to wash your
hair".

   Harriet left the room and Timmy eagerly hid his nakedness in the foamy
water, savoring the feeling as his young body was enveloped into the
temperate chasm.  During the next few minutes in which she let him soak
quietly, Timmy almost forgot the shame of being reduced to a mere child in
the hands of this goddess whom he called mommy.

   Suddenly he head his foster mother chatting with someone on the phone.

   "This afternoon?  That would be wonderful Jane!" She exclaimed in a
cheery voice.  "I've been wanting to take Timmy to the doctor for ages".

   Timmy felt his heartbeat racing as she spoke those word.  Was he going
to get a medical check-up?  No one but Harriet had seen him naked since he
was a small child.

   Harriet soon returned to the bathroom.

   "Don't look so worried sweetheart" She reassured him, while caressing
his cheek "She is one of mommy's close friends.  And she's a real nurse."

   Harriet poured a generous amount of shampoo into Timmy's hair and spend
a considerable amount of time lathering up his scalp with her long slender
fingers.

   Her hands were caring as they traced through his hair, playing havoc
with his feelings.  His eyes were peacefully closed, his lips slightly
parted.  Harriet smiled and gave him a kiss on the cheek as she manipulated
his naive senses.

   "Such a good boy," she whispered as she massaged the back of his head.
She could feel Timmy start to relax in her gentle hands.

   Softly grasping his delicate neck, she placed her lips next to his ear,
whispering: "Okay now, get onto your knees, bend over, and rinse your hair
out in the tub.  Be sure to keep your eyes closed."
Timmy quickly obeyed her command, all too well aware that his bum was

nicely on display as he did so.

   "Get your head down in the water sweetie.  Arch you back," Harriet said
as she gently pushed down on the back of his neck, while admiring his wet
and glistering behind.

   Timmy descended his head fully into the water, giving her a perfect view
of his bare bottom and the stiff member dangling between his thighs.
Harriet had to stifle a giggle at the sight.

   When Timmy's hair had been rinsed properly, she raised the boy to his
feet.

   "Now for the cold shower" Harriet announced while carefully helping
Timmy get out of the tub.

   "Please not today" Timmy pleaded, but there was nothing to be done.  It
was all routine.

   Placing the boy in the shower stall she quickly sprayed him down with
icy water.  The boy whined miserably as the freezing needles broke upon his
skin.  He desperately turned around as instructed, even bending over so
that Harriet could spray directly unto his sensitive anus and the tight
little sack beneath.

   "Please mommy" the boy begged, tears starting to form in his eyes again.


   When she finally turned off the water, Timmy looked like a sad wet puppy
with his teeth chattering heavily.  His erection had subsided and had
curled up, looking even less impressive and yet to Harriet, very cute.

   "Awww you poor thing," Harriet said as she hurriedly got him out of the
stall and wrapped him in a soft fluffy towel.

   Harriet held Timmy close as she rubbed his body through the towel.

   "You have been a very good boy," she said, smiling down at him.  Taking
his head between her hands, she pressed her lips to Timmy's, kissing him
long and leisurely.

   Harriet closed the toilet lid and sat down, pulling the boy in between
her knees.

   "let's get you dried off" she said as she pulled the towel from Timmy's
shoulders, once again exposing his naked body to the cool air of the room.

   Timmy felt utterly embarrassed and helpless as he stood before her like
this, being dried off like a small child.  Harriet carefully worked over
his slender body with the towel, paying special attention to his genitals
and the deep crease between his bubble cheeks.

   When he was sufficiently dry, Harriet walked over to the sink and
returned with a tube of body lotion.  She smiled into his blushing face
while squeezing a good amount of lotion into her hand.

   "Hands on your head" she instructed Timmy before bringing her creamy
palms onto the soft skin of his pubis.  Meticulously she coated his body in
lotion, making sure to spread it evenly - although there was one particular
part of his autonomy which received special attention.  Having the boy turn
around and grasp his ankles, Harriet generously applied the lotion onto his
recently spanked behind which was still fairly pink in color.  She even
slipped a creamy finger inside his vulnerable bottom, making the boy
whimper in response.

   Needless to say, Harriet was enjoying herself immensely.  The sheer
control she was asserting over the boy had her pulse racing with
excitement.

   When she couldn't prolong it any more, she took Timmy by the hand and
led him back into his room.  On the bed she had laid out a thin sleeveless
shirt with pastel prints, and a pair of pink panties.  Timmy looked up pleadingly at her, but didn't dare to protest.

   Harriet sat down on the bed and once again positioned the boy between
her thighs.  Picking up the panties she made Timmy step into them one foot
at a time, and then slid them up his slender legs, making sure to pull them
up tight around his bottom.

   Harriet thought the boy looked absolute adorable, standing there
blushing in his cute little panties.  She gave his panty-clad butt a soft
pat "Now raise your arms so I can get this shirt on you".  As she lowered
the garment down over his head, Timmy was somewhat relieved when the hem
reached to his upper thigh, thus mostly covering the embarrassing
underwear.




 Later, as lunch came to its end, the rat-at-tat of the doorknocker suddenly
pierced the silence of the house, notifying its residents about the
presence of visitors.  Harriet left the kitchen to open the door, and as
she did, Timmy heard an outburst of joyful female chatter; he began getting
uneasy as the lively conversation moved down the hallway.

   His foster mother reentered the kitchen accompanied by a tall woman in
her late thirties.  She was an astonishingly beautiful brunette, with fair
white skin and full red lips.  She was dressed in a plain nurse's uniform
that revealed a superb bust, a slender waist and wide, well-muscled hips.

   "Timmy, this is my good friend Jane."

   Jane stepped closer to the petrified boy and tenderly caressed his
already blushing cheek.

   "My, he's a pretty little boy, isn't he," Jane spoke to Harriet, not
acknowledging the boy's presence.

   "If only his behavior was as graceful as his looks!" Harriet replied,
smiling to her friend in a conspiratorial fashion.

   "Oh my, did you have to smack his naughty little bottom?"

   "Indeed.  In fact I just gave him a spanking this morning."

   Jane spoke in a stern tone as she placed a large medical bag on the
kitchen table "Well, I certainly hope you are going to behave for your
medical examination young man."

   Timmy gave his foster mother a pleading look, but Harriet just ruffled
his hair reassuringly.

   "Should we move into the bathroom?" She asked Jane.

   Jane thought about it for a moment, but decided that the kitchen would
suffice.  Besides she reasoned that the boy would properly feel even more
exposed in the bright and sterile environment of the kitchen.  She smiled
wickedly to herself at the thought.

   Picking up a tongue depressor from the bag, she placed her fingers under
the boy's chin and tilted his head backwards.  She saw that Timmy was
frightened.  This turned her on even more.

   "Open up now" she instructed him in a no-nonsense tone.

   The boy eagerly obeyed, opening his mouth as much as possible.  Jane
pressed down on his tongue with the wooden blade, while noting the perfect
symmetry of his teeth.  She thought the boy to be an excellent specimen,
and could hardly wait to get him undressed.

   Next she sat down with a stethoscope and ordered the boy to stand
between her thighs.  Timmy blushed furiously as she lifted the hem of his
shirt, exposing the pink panties underneath.

   "Cute panties" Jane commented in an amused voice while tracing a finger
along the waistband.  Both women giggled at this while Timmy hung his head
shamefully.

   Jane put the cool stethoscope against his stomach, making the boy
shiver.

   "How old is the boy" Jane asked while looking up at Harriet "Eleven?"

   "He's almost thirteen" Harriet answered while sitting down behind Timmy,
rubbing his back in a comforting manner.

   "Well, you've got some catching up to do tiger" Jane said while moving
the stethoscope up to his chest "But we'll get to that part in a moment."
To illustrate her point she gently patted the small bulge in his panties.

   She then spun the boy around and listened to his lungs for few seconds,
before addressing Harriet once again "Everything seems fine.  Now let me
have a look at that naughty little rump of his"

   Tears were forming in Timmy's pretty eyes as he shook his head
miserably.

   "Please mommy!"

   "Shhhhhh, it's okay sweetie, Jane has seen many naughty bottoms in her
lifetime," Harriet said reassuringly as she tenderly pressed the boy's face
against her chest.  Timmy was sobbing quietly against her soft bosom as he
felt her hands soothingly running down his back.  Her coaxing fingers
traced down his spine towards their final destination, while Harriet purred
in a comforting tone.

   The boy gasped as he felt her gentle touch on the sore flesh of his
buttocks.  As Harriet ran her hands over the swelling globes, Jane could
clearly see the outline of the boy's cute round bum.

   "Timmy, I want you to bend over and grasp your ankles." Harriet ordered
whilst exchanging a smirk with Jane.

   A muffled "Please, mommy..." came from Timmy, his face buried in the
folds of Harriet's sweater.

   "Remember what you promised earlier.  I shall not hesitate to take you
over my knees and thrash your naughty behind." Harriet illustrated her
point by squeezing Timmy's soft bottom-cheeks firmly.

   "Now be a good boy.  Bend over and present your adorable little bottom
to me and Jane"

   Timmy uttered a defeated sob before slowly unclasping his foster mother
and reluctantly bending over.  As he took hold of his ankles, Harriet
placed his head between her knees and pulled his backside slightly towards
herself so that his bum was literally pointing straight towards the
ceiling. She then let her fingers travel teasingly around the hem of his
shirt, before digging them into the waistband of his panties. 

Jane moved her chair so that she was seated right behind the unfortunate boy,
knees on either side of his straight legs.

   Smiling at her friend, Harriet began slowly pulling down the panties.

   Timmy groaned in utter embarrassment as he felt cloth abandon his
behind, rendering his sensitive flesh vulnerable and open to the hungry
lionesses who would undoubtedly devour his youthful, innocent body.

   A sigh of pleasure escaped Jane's lips as the boy's charms were revealed
to her lusting eyes.  The slightly pink cheeks contrasting beautifully with
the paleness of untouched skin between them.  The flawlessness of his
semi-erect member. So deliciously vulnerable.

   Timmy could almost feel their predatory, penetrating gaze upon his
exposed skin, examining every inch of his body.

   Harriet let the panties drop to his ankles and then pulled the shirt
past his upper torso, depriving him of sight as the white cloth came down
over his eyes like a curtain around a birdcage.

   "Oh my, Timmy.  Your naughty behind looks like it received quite a
spanking," Jane said as she reached out and placed her delicate, cool
fingers on the warm cheeks of his bum.  Timmy exhaled loudly in shock, his
trembling body recoiling at her touch.  Jane scored her nails gently down
his thighs, sending shivers through Timmys's body, while Harriet took over
the fondling of his bottom.

   "He doesn't seem to have any hair yet" Jane noted with a pleased
expression on her lips.

   "He's a bit of a late bloomer I'm afraid - still mommy's little boy."
Harriet punctuated her last words by softly patting his raised bum.

   "I better have a little feel inside his bottom" Jane proposed "To make
sure everything is fine"

   Harriet agreed and placed her fingers inside the crease of Timmy's
bottom.

   "Let me just open up his little bottom for you - Timmy, be a good little
boy and relax your buttocks while I spread them apart nice and wide for the
nurse"

   Her words could not have been chosen better for the humiliating effect
they had on the boy, his face now suffused in an almost purple blush
underneath the shirt.

   "Please, mommy" he whimpered, absolutely mortified by the thought of
having his most private part exposed to this beautiful woman whom he had
only just met.  The way in which Jane had practically undressed him with
her eyes at first sight had the boy convinced that she was taking great
pleasure in his nudity; this conviction now only worsened the excruciating
shame he felt as his foster mother slowly began to part the soft globes.

   Both the women uttered a small sigh as the little pink dimple of his
anus was exposed to them.  As Harriet spread his cheeks wide apart, Jane
pouted her lips and blew air onto the appealing orifice, making Timmy
recoil violently.

   "Ohhhhhhh" Timmy whimpered, feeling his tiny rosebud spasm
involuntarily.

   The women giggled as the boy wiggled his bum and his little sphincter
winked at them seductively.

   "This must be the cutest little bum-hole I have ever laid my eyes upon,"
Jane said as she let a finger trace around the edge of the quivering ring
muscle.

   Timmy could have died of embarrassment as they nonchalantly discussed a
part of him so private that he had not even seen it himself.  But worst of
all was that, even though he could not think of a more shaming position to
be in, his pen-is had begun to stiffen again.  Jane was getting increasingly
moist as she brought a long finger up to her voluptuous lips and coated it
with saliva.

   "Shhhhh, Timmy, just relax while I pop my finger up inside you," Jane
soothed as she traced her wet finger around the pink star, smearing it with
spit.  Deftly, her neatly manicured nails traced over the puckered entrance
to the boy's anus, causing the flesh to recoil and constrict violently each
time she touched it.

   "Pl..please don't, miss," Timmy whimpered in anguish.  With the shirt
around his head and these stunning goddesses towering over his behind, he
felt powerless about what would happen with his body.  Even the most
private bodily functions, like what went in and out of his sphincter, were
out of his hands.

   "Young boys always make such fuzz about having their little bottoms
penetrated," Harriet remarked while she squeezed the boy's buttocks firmly
in excitement, keeping them spread wide.

   Suddenly Jane pushed her finger forward, watching her fingertip slip
through the pulsing rosebud.  The little orifice clutched her finger
tightly as she slid it in past the first knuckle.  The boy's velvety
insides felt warm and soft as she dexterously drove her long digit all the
way inside him.  Timmy was trembling all over.  Her finger roamed freely
and mercilessly, arousing his naïve sexual feelings to fever pitch.

   "Uhhhhhh, miss!" Timmy was beside himself with shame as he felt the
nurse's finger explore his insides thoroughly.

   Locating his prostate gland, Jane scored her nail gently across the
responsive surface, making Timmy wriggle his bottom helplessly.  His rectum
was struggling frantically to expel the rude intruder.

   Retracting her finger gently, Jane slowly slid out of his tight intimate
canal.  Timmy gave a small sigh of relief as the cruel teasing of his
bottom came to an end.  But his respite was short lived: he felt Jane once
again forcing his reluctant anus to comply with her probing, this time by
two saliva-coated fingers.  Timmy bit his lip as his sphincter stretched
painfully to accommodate the relentless advance.

   "He's a tight little sissy," Jane noted as she struggled to propel her
voracious and insistant fingers.  Letting her other hand trace down over
his perineum, she cupped his smooth genitals beneath.

   "Give me full and unhindered access Timmy," Jane calmly demanded,
tightening her grip.  Suddenly the little puckered hole
gave in, and Jane watched with satisfaction as her fingers delved into his
smooth pliant channel, impaling him right up to her knuckles.

   "Uhhhhh miss, please" Timmy pleaded as she ran her fingertips over the
his quivering prostate.

   Timmy felt her fingers deep inside of him, stimulating the sensitive
gland.  He could feel an answering throb in the tip of his pen-is and to his
horror he felt Jane casually place the delicate fingers of her other hand
on his engorged member.  Jane deftly pulled the foreskin up the shaft,
deliberately and slowly revealing the sensitive flesh beneath.

   "Argghhh..  oohhhh.."

   Scoring her nails over Timmy's prostate one last time, Jane swiftly
withdrew her fingers, causing a loud popping sound, like cork emerging from
a wine bottle.  The women did not even try to suppress their amusement over
this.

   "It even sounds cute!" Jane giggled while cupping the boy's scrotum on
one hand, and taking hold of his rigidly erect pen-is with the other.

   "Oh my Timmy, your little willy is all hard," She said in pretend
surprise as she patted the underside of his stiff little member "You can't help
yourself, can you?"

   "N...no miss...  I'm sorry," Timmy softly sobbed from between the knees
of his mommy.

   Meanwhile Harriet traced two fingers down the pink crevice of his plump
buttocks.  Timmy felt an odd empty feeling when Janes's slender fingers had
retracted from his behind, but they were soon replaced by Harriet's
delicate touch.  His will to resist had gone as his sphincter stretched
almost readily over the probing fingers of his mommy.  Her deft and
experienced penetration soon imposed her probing fingers deep inside his
moist and velvety canal.

   Harriet squeezed her knees together slightly and whispered softly, "Just
relax now...  it will all be over soon." Her soft voice played havoc with
Timmy's feelings, as did the soft yet imperious fingers that probed deep
inside his bottom, applying a firm pressure and motion to his swollen,
inflamed prostrate.

   Jane was devoted to the task of skillfully and diligently milking the
poor boy, her gentle touch playing with the smooth marbles of his sack as
her other hand moved over his pen-is, pulling his foreskin up and down the
corona of his sensitive flesh.

   "Ohhhhhhhh uhhhhhhh please..."


   It had all become too much for Timmy, who was now shaking visibly from
the intensity of their caresses. A few spurts of c-um erupted from his throbbing pen-is while Timmy groaned in helpless ecstasy. 

   "Arrhhhhhhhhh uuhhhhhhh," Timmy moaned, struggling to keep his legs from
folding as the intense orgasm paralyzed his trembling body.

   When the boy had finally been drained completely, Harriet let go of his
softening pen-is and gently patted the smooth scrotum.

   "Such a naughty little boy.."

Harriet reluctantly withdrew her deeply embedded fingers, watching with
amusement as the tight little hole closed behind them.

   Both women exhaled contentedly while Timmy remained in his degrading
position, panting heavily.  Harriet released the boy from between her knees
and took hold of the shirt around his head, pulling it down over his
extended arms.

   "Right, stand up young man," Harriet said as she gave him a slap on his
upturned buttocks.  Timmy slowly got up with a flushed face, looking down
onto the white globs of c-um splattered on his stomach.

   "My, my, Timmy.  Look at the mess you've made," Harriet said as she
reached up and caressed his blushing cheeks.

   "I'm sorry mommy" the boy muttered, burning with shame.

   "Speak up, boy!  And look up while addressing us," Harriet demanded,
cupping Timmy's chin and forcing his crimson face upward, to meet their
scrutinizing eyes.  Timmy found it almost impossible to focus on the
penetrating stares.

   "I'm sorry" he whimpered, his beautiful brown eyes glistering with
tears.

   Harriet gave him a magnanimous smile and tousled his hair.  "Good boy.
Let's get you cleaned up.

   She had Timmy step out of his panties, and then led him back into his
room naked.  Jane enjoyed the view of the his naked bottom as she followed
them up the stairs.  How she would have loved to have Timmy all to herself.
The things she would do to him..

   Back in the room, Harriet spread a big fluffy towel on the bed.  She
grabbed the boy by his shoulders, and gently pushed him down onto the towel
on his back.

   "You know how mommy likes you..." His foster mother commanded.

   A small sigh escaped Timmy's lips and although weary, the boy promptly
drew back his legs and hugged them to his chest.

   "God he is cute!" Jane thought as she entered the room.  This was how
she liked to see a young boy.  All his charms accessible and exposed to her
every whim.

   "I'm going to get some warm washcloths" Harriet said and disappeared
through the door opening, leaving the boy alone with Jane.

   Timmy couldn't help himself from looking up at Jane through his widely
spread legs.  She had an amused smile on her face as she approached the boy
and placed a cool hand on the inside of his smooth milky-white thigh.
Timmy whimpered at the intimate touch.

   "Are you thinking naughty thoughts Timmy?" Jane asked and gently flicked
the boy's rapidly engorging member.  Timmy shook his head helplessly as he
became erect once again.

   "Are you sure?"

   "Yes miss..." the boy whimpered.

   "Then maybe you're just a naughty little boy who likes being naked in
front of mommy's friends, huh?"

   Timmy was blushing furiously while he continued to shake his head.  He
felt exposed and humiliated beyond belief as he obediently remained in the
degrading position.

   "Maybe you need another spanking?"

   "No please miss" k Jane marveled in the feel of his soft yet firm flesh,
as she alternated between cupping and patting one of his elevated
bum-cheeks.

   "Let's get you cleaned up young man!" Harriet said as she reentered the
room, handing Jane one of the washcloths "Hands above your head now"

   Timmy placed his arms flat above his head and closed his eyes in defeat
as the two women began working the soft washcloths over his smooth young
body.

   Harriet took both his slender ankles into her left hand and bend him
backwards while moving the washcloth up and down between the cheeks of his
bottom.  Meanwhile Jane cleaned his stomach and pubic region, occasionally
touching his erect pen-is with the back of her band.

   Harriet then spread his legs wide apart and encased his entire erection
in the warm cloth.

   "My, my.  Little boys have no self-control it seems" she commented while
smiling at Jane.

   They quickly dried off the boy, before bending him backwards again.
This time Harriet was seated behind Timmy, holding him in the shameful
position by his ankles.

   From between his widely spread thighs, Timmy observed Jane Shaking down
a can of talc-um.  She sprinkled a generous amount of powder onto Timmy's
genitals and bottom, before lifting his delicate eggs and rubbing her
coated fingers all over his sensitive perineum.

   "Uhhhhhhh..." The boy gasped as she handled him expertly, teasing his
naive sexual feelings to fever pitch.

   Meanwhile Harriet bend down and placed a small kiss on his forehead
"Look at you Timmy, fancy a big boy like you having to have your little
bottom and willie powdered"

   Jane smiled broadly at Harriet's words as she soothingly ran her hands
over the boy's skin.  Pouring some more talc-um into the palm of her hand,
she insinuated her slender fingers between the cheeks of his bottom,
working the powder into his crevice.

   With a long stroking motion, she traced her hand from his scrotum down
in-between his bum, repeating this action over and over while his member
throbbed vigorously in response.  Then she proceeded to simply pad down the
entire area with the flat of her hand, reveling in the feel of his flesh
under her palm

   "Doesn't that feel much better?" Jane cooed while working a few traces
of talc-um around his spasming anus.

   "Uhhhhhhh" Timmy whimpered with a scarlet blush as Jane traced her nails
across his puckered anus.

   "I'm going to give him something to help him sleep" Jane said as she
wiped her hands on a towel.  Reaching into her front pocket, she pulled out
a small box of suppositories.

   Timmy's face was a picture of pure dread as Jane unwrapped one of the
white projectiles.

   She smiled down at him as she wiped a dap of Vaseline onto his tiny pink
dimple and then lined up the suppository.

   "Just relax sweetie...  there we go" Jane said, penetrating Timmy's
elevated bottom once again.  As the suppository was pushed in, she followed
it up with a long bony finger, inserting it all the way to her knuckle.

   "Uhhhhhh ohhhhh" Timmy whimpered, pushing the side of his face against
the pillow.

   Jane twisted and turned her embedded finger for what seemed an
unnecessarily long time, before slowly retracting.

   Timmy could feel the anesthetic almost immediately, spreading like a
warm wave from his bowels.

   Harriet let go of his ankles and reached into the nightstand "Do mind
diapering him Jane?  Timmy is a bit of a bed wetter I'm afraid"

   Timmy could have died of shame as his foster mother revealed this most
embarrassing secret.

   Jane smiled wickedly down at the boy while encircling both his slender
ankles in her left hand.  "Ofcourse not Harriet!  I would love to diaper
this cute little bottom of his." Her last words were accompanied by a
series of soft slaps onto Timmy's defenseless fanny.

   Harriet placed several items on the bed, one of which looked like a
large cotton napkin.  Folding it into a triangle, she placed it under
Timmy's upturned rump.

   Jane slowly lowered the boy down onto the bed, and began fastening the
corners of the triangle in front of him, pinning the soft fabric together
over his throbbing erection.

   Harriet stood by his side and traced her fingers down Timmy's pubis,
cupping his rigid member on the outside of the cotton cloth.

   "What a day you've been through, you poor thing.  I want you to take a
nice nap now, Timmy, all right?" Harriet said as she placed a small kiss on
the boy's feverishly blushing cheek.

   Timmy felt relieved when the duvet was finally tucked around his
shameful appearance.

   "Get some sleep; you'll need it," Harriet advised in a soft voice.  Then
she got up and was about the leave with Jane, when suddenly she remembered;
"Oh, we forgot to take his temperature".

   Before Timmy could even utter a whimper, he felt the duvet leave his
body once more.  Promptly the boy was flipped onto his stomach.  He pressed
his face into the pillow in shame as cool fingers pulled down the back of
his diaper past the curve of his buttocks.

   Both women found the boy absolutely adorable with his bubble butt being
pushed up by the cloth material.

   Timmy felt a hand pushing down on the small of his back, and then
fingers prying open the cheeks of his behind.  The familiar sticky feeling
of Vaseline soon followed, along with the merciless teasing of an intruding
digit.  Then the icy tip of the thermometer found his sensitive opening,
sliding easily up inside him.

   Timmy was starting to drift off from the anesthetic, and the voices he
heard seemed far away.

   "I would really love to use one of my strap-ons on the boy" Harriet said
while playing around with the thermometer.

   "Why don't you?" Jane was running her hand up and down Timmy's lower
back.

   "He's got such a tiny bottom" Harriet illustrated by point by cupping
one of his buttocks.

   Jane smiled wickedly at this "Don't worry, just make sure to lube him up
generously - little boy's bottoms were meant to be thoroughly used by their
mommies"

   "That I must agree with" Harriet said with a giggle "By the way.  I'm
going out of town next week.  Would you care to babysit?"

   Jane's face lit up at the question.  She placed a hand on Timmy's pale
bottom, gently digging in her nails "I would love to Harriet.  I'm going to
take very good care of this little sissy".


Harrietmarwood

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Re: Timmy - A good little sissy
« Reply #1 on: March 13, 2016, 11:22:00 AM »
It was evening when Timmy awoke to the sight of his foster mother
standing over him, beside his bed.

   "Did you have a nice nap Timmy?" she purred softly, "Mommy tried to have
a nap too, but I just couldn't stop tossing and turning with thoughts about
what a good boy you were earlier."

   Still slightly numbed from the suppository, the boy felt himself being
raised from the bed, and led into his mommy's bedroom down the hall.  It
was large, cozy room dominated by nuances of brown and beige.  A lit
fireplace stood crackling in one end of the room, sending waves of heat
across Timmy's naked skin.

   Harriet sat down on the king-sized bed and positioned the boy between
her strong thighs.  Then she dug her fingers into the waistband of Timmy's
diaper and swiftly pushed it down to his ankles.  Timmy blushed as he was
once again exposed to the gaze of his foster mother.  After inspecting his
body thoroughly from head to toe, Harriet told the boy to warm up his
little tush for her.

   With the cloth garment around his ankles, Timmy waddled pathetically
over to the fireplace.  Placing his palms upon his knees he stuck out his
pale bottom towards the fire, feeling absolutely ridiculous.

   Harriet stifled a giggle and lovingly ruffled his hair.

   "Good boy."

   She left the room, but returned shortly after, striding leisurely into
the room with a huge pink strap-on protruding from her pelvis.  Harriet had
removed her skirt, but the phallus and harness around her hips kept her
panties hidden from Timmy's gaze.

   He had once wandered past her bedroom door, which had been ajar, and
stopped in awe at the sight of her dressed only in a blouse and panties,
facing away and bending at the waist to pick something up off the floor.
The sight of the thin cotton material of her underwear clinging to the
full, plump curve of her womanhood had caused him to gasp, his young body
springing to attention.  At that Harriet had spun around, standing tall and
glaring down at him.  Moments later Timmy had been lying on his back on his
bed, arms and legs tied to the headboard, genitals and bottom bared and
exposed, howling in pain as Harriet's palm came down on his sensitive flesh
over and over again.  Since that day though the image had haunted his
dreams, he had never again caught even the merest glimpse of his foster
mother undressed.

   Now she stood before him, hands on hips, the soft wool of her cashmere
sweater accentuating her large, firm bosom, her shapely legs bare, leading
his gaze up to the large dil-do that pointed proudly at him.  Timmy felt
helpless as he stood trembling before her, naked and hairless with a diaper
around his ankles.  His buttocks tightened protectively at the sight of the
menacing plastic phallus.

   Timmy had never seen a dil-do before, but he already knew its purpose.

   Without being told, he kneeled on the soft fur beneath him, head down,
and arched his back as much as he could, looking back at her with a nervous
expression on his face.

   "Such a good boy," Harriet purred while gracefully falling to her knees
behind him. 

   She drew a deep breath.  She could almost hear the exhilarated beat of
the boy's heart.

   Raising her hand slowly, she suddenly brought it down hard on the
elevated twin hillocks of his bottom, causing the boy to yelp out in pain.

   "Awwww!  Please mommy!" he whimpered.

   "I think we better make sure you understand your place Timmy.  I won't
tolerate any fuss when I pop this thing up into your little hiney -
understood?"

   "Yes mommy..."

   And so Harriet began her chastisement of his backside, raining down
slaps upon his perky rump.

   "Smack!  Smack!  Smack!  Smack!"

   She alternated between the two globes, a faint blush extending across
the smooth surface.

   "Smack!  Smack!  Smack!  Smack!"

   "Smack!  Smack!  Smack!  Smack!"

  "Awww, please mommy, I'll be good!" the boy begged her with pleading
eyes.

   "Smack!  Smack!  Smack!  Smack!  Smack!"

   "Auuuu!  Awww!  Please!"

   "Smack!  Smack!  SMACK!"

She swung from underneath at his pale thighs.

   "Smack!  Smack!  Smack!  Smack!  Smack!  Smack!"

   The boy had gone quiet as she stoically resumed executing his sentence,
her fiery hand descending between long, uneven intervals of silence.

   "SMACK!.......  SMACK!.......  SMACK!  SMACK!"

   Harriet held her stinging hand midair.  As she listened to the quite
sobs of the boy, she took pity on him and ceased the preemptive punishment.


   "Shhhhhhhh.  It's okay sweetie," she cooed while soothing her hands over
his bright pink flesh.  "Now, be a good little boy and tell me; who does
this adorable little bottom belong to?"

   She scored her nails across his sore buttocks in a possessive manner.

   "You, mommy," the boy whimpered.

   "Such a good sissy boy."

   She grabbed the lubricant can next to her, and proceeded to pour
generous amounts of clear thick liquid down the crease of his bottom.
Timmy gasped as the cool substance trickled down his burning flesh.

   Likewise she thoroughly coated the big pink strap-on, making sure he
would be able to take the entire length.  Spreading his cheeks with one
hand, she started to work in the lubricant around his sphincter, watching
with fascination as the tiny pink star puckered up at her touch.

   "Uhhhhhhh please," the boy gasped as Harriet popped first one, then two
long fingers up inside him, overcoming his sphincter's resistance with
little effort required.

   Fully embedded, she twisted her digits around a couple of times before
retracting abruptly.  Quickly she pressed the tip of the can against his
anus and began squeezing its cool content directly inside the young boy's
bowels.

   "Uhhhhhhh, Ahhhh."

   The boy gasped helplessly at the invasion as Harriet emptied the entire
lubricant can deep inside of him.  Throwing the can aside, she positioned
the dil-do along the crease of his bottom, moving the bulbous head up and
down between his firm young buttocks.  The strap-on looked enormous next to
his twelve year old bum.

   She leant over him and kissed his cheek while sliding her hand
underneath him, patting the underside of his rigid erection.

   "My, my, judging by your little friend here, I'd say you love being my
little play-toy,"

   She whispered teasingly into his ear before getting back into position.
Lining up the dil-do with his quivering virgin rosebud she pressed forward,
watching closely as the little pink opening began to give away to the thick
intrusion.

   "Uhhhhhhhh...  please....  Ohhhh..."

   Timmy moaned, beside himself, as his tight orifice began stretching
around the strap-on.

   Using the palms of her hands to spread his cheeks wide apart, Harriet
lightly dug her nails into the warm soft mounds of his backside and pressed
forward.  The tiny glistering hole began opening up more, almost nearing
the edge of the strap-on helmet.

   "Ohhhhhh...  uhhhhhhh....  please...  mommy..."

   Keeping up a steady pressure, the rosy ring of muscle suddenly gave up,
and with a rush of ecstasy, Harriet watched the head pop up inside his
velvety warm rectum.

   "Ohhhhhh...  uhhhh..."

   Timmy cried out in defeat, as he felt this massive intrusion settle
within his very core.

   Harriet could not deny the delicious thrill she experienced, as she
quickly followed up the phallus tip with a couple of thick greasy inches,
feeding his poor little fanny unrelentingly.

   "Ohhhhhhh ohhhhhhhh ahhhhhhhh!"

   Timmy could do nothing but accept whatever length and size Harriet
advanced on him.  He felt his pen-is throb violently against his stomach,
leaving thick droplets of pre-c-um around his naval.

   Harriet pushed down on him firmly, easing inch after inch inside his
little bottom until the entire length was buried to the hilt in his bowels.
She was quite pleased that she had been able to fit the whole tool inside
his slender frame.

   "That's it, such a good little boy you are for mommy, and how perfect
your sweet little hole looks wrapped around mommy's toy," Harriet purred.

   She spread his cheeks even more widely apart with both hands, crudely
exposing the sight of his young bottom and the pink shaft penetrating its
tight opening, and then began fuc-king him with slow rhythmic thrusts of her
pelvis.

   "Ohhhh uhhhhh."

   Timmy's limbs went into small fits of spasms at the acute stimulation of
his young body.

   Gradually she began increasing the length of her thrusts, until she was
working the entire dil-do through his slippery anus, piling down on him with
long, full plunges.  The sight of his pink rosebud wrapped tightly around
the girth of her shaft had her going mad with lust.

   "Uhhhhh ohhhhh....  Ahhhhh!"

   "Such a good little boy you are" Harriet kept murmuring as she lovingly
violated his round taut bottom.  She withdrew right until the head of the
strap-on, before plummeting back in with a steady push, pressing her pelvis
firmly against his sore behind.

   Back and forth.  Again and again the glistering phallus slid along his
pliant velvety canal.  With each thrust the base of the dil-do pressed to
Harriet's clitoris, the sensitive organ stiff and aching.

   She angled her hips, altering the thrust to make the most of his
delicious rectum, rocking her body to heighten her pleasure.  Beneath the
boy, his own swollen coc-k swung to and from with her thrusts.  Harder, and
deeper Harriet used him, her hands now on his slender hips.

   A few more thrusts later and she felt that familiar feeling building
between her legs, and beginning to spread out through her body.  Harriet
threw her head back, and pushed hard forward, deeply in to her foster son's
submissive body.  She groaned in pure ecstasy, her clit throbbing, body
clenching as she continued to ride the young boy, until her orgas began to
subside.

   Harriet continued though to stroke the dil-do slowly in and out of
Timmy's sweet little opening.  Now her moans had ceased, she could hear the
boy began breathing more rapidly.  Tracing her index finger down the rim of
his dilated anus, she incased his genitals in a firm possessive clutch.

   "Is my little boy about to have another accident?"

   She asked, pulling gently on his tight sack.

   The boy timidly nodded his head.

   "Well, that won't do at all!"

   Placing both hands upon the small of his back she raised herself up in
one smooth motion.

   "PLOP!" it said, as the dil-do left his slippery insides.

   The boy was left with an odd sense of emptiness as his anus stood gaping
up towards her gaze.  She stood silently for a few seconds, admiring the
subservient exquisiteness before her.

   Removing her harness she raised the boy and cradled him in her arms.

   "Such a good boy you were," she purred while looking deep into his eyes.
She could feel his arousal pulsating against her thigh.

   "Mommy is going to give you a nice icy shower to prevent any more
accidents" Harriet announced while cupping both his buttocks in her hands
"And then I'm going to play some more with that saucy little rump of yours"

"But.. My bottom is really sore mommy" Timmy pleaded with her, as he involuntarily squeezed his buttocks together defensively.   

"Things are going to change around here Sweety" Harriet said, ignoring his please "You will soon learn what it means to be a sissy boy".



   TO BE CONTINUED



   Feedback is much appreciated.  Feel free to send me your ideas and
wishes for future stories: harriet-marwood ( " at " ) hotmail.com


sissy marci

  • Mommy's Dearest
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Re: Timmy - A good little sissy
« Reply #2 on: July 29, 2022, 12:18:23 PM »
Lovely story, thank you

 

The more you give, the more I can give back.

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