The Lovable Curmudgeon
Copyright 2026 by The Lovable Curmudgeon, all rights reserved
[1,991 words]
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This
story is intended for adults only. It contains depictions of forced
nudity,
spanking, and sexual activity of preteen and young teen children for
the
purpose of punishment. None of the behaviors in this story should be
attempted
in real life, as that would be harmful and/or illegal. If you are not
of legal age in your community to read or
view
such material, please leave now.
Chapter 1
Bobby and his sister, Susan had always been close. Bobby would be turning 4 in two days when his mom and dad first
brought Susan home from the hospital. His father joked that Susan was an early birthday present for him. Bobby
laughed, but he adored his new sister as if she actually was and endeavored to take care of her.
On one such occasion, following a long exhausting day at the amusement park, Bobby was all too happy to do just that.
The siblings were 12 and 16 at the time and Susan had fallen asleep during the long car ride home. She was a very
sound sleeper and once she was out there was simply no waking her. When they arrived back home, she had to be carried
from the car into the house and Bobby, who was quite strong for his age, was tasked with her transport.
Bobby’s mom just shook her head and laughed as he carried his sleeping sister through the front door slumped over his
shoulder, behind in the air, arms and long brown hair dangling down his back.
“Oh you might as well just take her on up to bed. She’ll be dead to this world until morning. Just don’t put her in
bed with her shoes on. I just changed those sheets.”
Bobby nodded, shifted his load slightly and headed upstairs while his mother and father remained downstairs for a
nightcap.
Once in Susan’s room, Bobby leaned forward and plopped her onto her bed. She made a soft sigh and her eyes flickered
briefly, then closed again. Bobby couldn’t help but smile looking down at her. She looked so sweet and innocent lying
there in the cute blouse and culottes set she had worn to the amusement park that day. Like a living doll, he thought
as he knelt down to untie his sister’s shoes. He gently pulled them from her small feet along with the cute ruffled
top socks she had worn to complete her ensemble.
Bobby couldn’t resist giving his sister’s bare feet a little tickle, which brought a smile to her lips, but failed to
wake her. Bobby blushed briefly as he was getting up, accidentally catching a glimpse of Susan’s underwear through the
wide leg openings of her culottes. Though she was only 12 at the time, it was plain to see her body was changing and
had begun to blossom. To Bobby though, Susan was and had always been just his little sis.
He chuckled to himself as he struggled to maneuver the covers out from under Susan’s limp body, so that he could get
her the rest of the way into bed and tucked in. In doing so, he noticed Susan’s flannel pajamas neatly folded under
her pillow. They were her favorite. The ones she always slept in. Bobby stood there for a moment looking at his
sister’s pj’s then back to Susan and back to the pajamas again.
“Should I put these on her?” Bobby wondered out loud. “Mom did say not to put her in bed with her shoes on. She
probably wouldn’t want her to sleep in her clothes either.” Bobby further mused.
Bobby brandished a boyish grin as he suddenly realized, in order to get Susan into her pajamas, he’d have to undress
her first, removing the top and culottes she had on now. He wasn’t apposed to the idea. The thought of doing so
actually amused him. It’s just that he wasn’t altogether sure it would be appropriate.
It was about that time he heard his parents coming up the stairs. Bobby’s mom ducked her head in, while his father
continued on down the hall to their room.
“Did you get that sleepyhead into bed okay?”
The moment Bobby’s mom saw Susan lying there so innocent and peaceful, she couldn’t help but smile warmly.
“Aw… Just look at her. Isn’t she just a little sweetheart?”
Bobby let out a sigh of relief as he stood there holding Susan’s 2 piece flannel pajamas in his hands. He was off the
hook or so he thought, figuring his mom would takeover the task of getting Susan ready for bed. Bobby’s mom looked
down at the pajamas and gave him a sweet smile.
“Aw… Aren’t you the thoughtful young man, taking care of your little sister like that?”
Bobby was about to hand his mother Susan’s pajamas, when she continued.
“That’s a good idea too. Putting Susan’s pj’s on her. You know how particular your sister is about her things. Heaven
forbid her new culottes set should get all wrinkled by letting her sleep in them. We’d never hear the end of it. Just
be careful getting them off of her. She’d be even more upset if they got torn. Well, goodnight dear.”
Bobby’s mom went on down the hall to her and his father’s room as Bobby stood there dumbstruck. Not only was his
mother not upset that he was contemplating undressing his own sister as she slept, she said it was thoughtful of him!
Bobby let out a little snicker and shrugged, speaking aloud to his still sleeping sister.
“Oh well, I already got your shoes and socks off. Might as well finish the job I suppose. Not like we haven’t seen
each other in our underwear before.”
That was true, but this somehow felt different to him. Nevertheless, Bobby leaned down and began unfastening Susan’s
belt, slipping it from the loops sewn into the waistband of her culottes. His hands began to tremble as he undid the
catch at the side and got them unzipped. He gently tugged them down little by little, over Susan’s hips, thighs and
legs, until they were completely off of her. He then folded them neatly just the way Susan would have liked and draped
them over the back of her vanity chair.
Bobby displayed a bashful grin as he looked back at his sister. Her legs slightly parted, with her snug white cotton
panties peeking out from under the hem of her frilly blouse. Bobby took a deep breath and began untying the bow at the
blouse's collar. The buttons would follow, with the lace adorned cups of Susan’s cute white bra coming more and more
into view as each button left it’s slot. Bobby was somewhat taken aback once he got the blouse fully unbuttoned
though. He knew that Susan had started wearing a bra, but he was surprised to learn that it wasn’t a trainer and that
at the tender age of 12, she had actual cleavage. Albeit largely due to the style of bra she had on.
“Damn...” He found himself muttering under his breath as he ogled Susan’s chest.
Bobby carefully maneuvered Susan’s blouse out from under her limp body. It too was neatly folded and placed with her
culottes over the back of the vanity chair.
Bobby couldn’t help blush as he looked back at Susan lying there in just her underwear. A lace cup white cotton bra
with matching lace waistband panties. Despite his shame, as he got nearer, he found himself lightly touching the cute
little pink flower sewn between the cups of his sister’s bra and lightly tracing the lace waistband of her snug white
cotton panties. There was no denying the desire he felt at that precise moment, but Susan was his sister and Bobby did
his level best not to lose sight of that.
Still, here before him was not only his sister, but a beautiful young girl on the verge of womanhood and her current
state of undress was not helping matters. Try as he might, Bobby was finding it increasingly difficult to fight the
urge to take a peek at what lie beneath his sister’s conservative, yet decidedly feminine underthings. It would become
a battle of conscience as he prepared to get Susan into her pajamas.
Bobby picked up Susan’s flannel pajamas and examined them to see how they went on. It seemed both the top and bottoms
were pull on, with no fasteners at all. That simplified things a bit, but at the same time made getting them on
someone who was sound asleep, more difficult. It seemed like getting the bottoms on her would be the most challenging,
so Bobby decided to do that first. He started by rolling up the legs of the pajama bottoms and slipping them over his
sister’s bare feet. That was easy enough and he was even able to pull them up midway of her thighs with little
difficulty. The hard part was going to be getting them up over her rump and hips with her lying flat.
Bobby chuckled at the ridiculousness of the situation as he looked down at Susan, her pajama bottoms only halfway up,
her snug white panties and bra still in full view. He decided to try and roll her over onto her side. This
unfortunately, gave him an excellent view of Susan’s backside and proved quite distracting. The soft cotton fabric of
her full back white panties hugged her curves like a second skin, the elastic leg openings gently pressing into the
flesh of her supple upper thighs.
Bobby found himself lightly tracing the curve of Susan’s heart shaped rear end with his fingertips.
“C’mon dumb ass, she’s your sister for goodness sake!” Bobby scolded himself, quickly drawing back his hand.
He hastily maneuvered Susan’s pajama bottoms up one hip, gently guiding her over on her back, then rolling her onto
her other side to pull them all the way up. Bobby smiled as he gently lowered her onto her back once more. Susan’s
snug white panties were now hidden from view, but her cute white bra was still fully exposed. As was her cute tummy
and navel, which Bobby couldn’t resist giving a little tickle to. Once again Susan smiled in her sleep without opening
her eyes. Bobby smiled as well and shifted his focus to his sister’s lace cup bra.
“Hmm… do girl’s sleep with those on, I wonder?” Bobby contemplated aloud.
Convincing himself that it was more about Susan’s comfort than his desire to see her nipples, Bobby carefully slid his
hand under his sister’s back to unhook her bra. The moment the clasp was released, Susan’s cleavage disappeared,
making Bobby chuckle.
“Oh my. All is not as it seems!”
With a bashful grin and trembling hands, Bobby slowly slipped Susan’s bra straps from her shoulders, allowing her
perfectly formed young breasts to jiggle free. The sight of her dark nipples made Bobby pause. Never had he seen such
beauty. He couldn’t help but want to touch them and did so lightly with the tip of his finger, causing yet again a
smile to form on Susan’s lips as well as a reddening face for Bobby.
Bobby looked down and sighed as he reached for Susan’s pajama top. “If you weren’t my sister….”
He took the top and gathered up the fabric, spreading the neck opening and carefully slipping it over Susan’s head. He
did the same with the sleeves, gently guiding her arms through. He smiled as her bare breasts jiggled about as he
cradle her shoulders, in order to maneuver her pajama top into position. Susan was finally in her flannel pj’s and
back to being just Bobby’s little sister. Bobby pulled the covers up and tucked her in, giving her an endearing smile
and a kiss on the forehead. He then turned to leave, placing Susan’s bra with her other clothes draped over the back
of her vanity chair.
“Goodnight, kiddo.” Bobby whispered to which Susan replied, “Thanks, mom.”
Bobby chuckled as he stepped into the hall, quite amused to be called mom, but relieved his sister had assumed it was
their mother who had put her to bed. Before going to bed himself, Bobby headed for the bathroom to take a much needed
cold shower.