Sitting With the Sitter
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The Sitter free porn video
The Sitter
By Cal Y. Pygia
Dinner and a movie. Nothing special. Just the typical date. However,
the night out had seemed special to Jerry and Diane Spencer because, as a
married couple with a hyperactive twelve-year-old son with an attention-
deficit disorder on their hands, a night out, doing anything together,
was a treat, made all the rarer by their difficulty in finding a sitter
for Dennis.
He wasn't a bad kid, really. He was just all boy, rambunctious and
wired. He had trouble doing anything that required him to sit still for
more than fifteen minutes. Consequently, he was a handful. After
sitting with him once, most teenage girls never returned. The Spencers
hadn't named their son after the Hank Ketchum character, Dennis the
Menace, of course, but they may as well have. Their son was every bit as
difficult as the famous cartoon boy.
They'd gone through the half dozen teenage girls in their neighborhood
who babysat, and every one of them refused to have anything more to do
with Dennis. Consequently, Jerry and Diane had become pretty much
recluses. Jerry worked all day as a consultant, and Diane kept hearth
and home together, as best she could, with Dennis underfoot before and
after school and all weekend. They'd tried, for their own, as much as
their son's sake, to interest Dennis in joining the Boy Scouts or the 4-H
or to get him to join a sports team. He'd refused. He wouldn't even
agree to take up a hobby. Since Diane was around Dennis far more than
Jerry was, her nerves were worn to a frazzle, and the couple found that
they were beginning to argue with one another more than they were
cuddling or having sex.
They'd each about reached the end of their ropes, losing hope that anyone
would ever again agree to baby sit their son. Then, as if in answer to
an unspoken prayer, Becky Lewis moved in across the street. Before any
of her peers could warn her against accepting their offer to baby sit
Dennis, the Spencers had asked her to do so, and she'd agreed. As a
result, for the first time in over a year, the Spencers had enjoyed a
night out on the town together. Unbelievably, neither of their cell
phones had rung even once. As impossible as it seemed, Becky appeared to
have things under control, and, more importantly, to have Dennis under
control.
"Maybe I should give the sitter a call," Diane had suggested to her
husband, after their plates had been cleared away and they were awaiting
the waitress' delivery of their desserts.
"You shouldn't," Jerry replied.
"What if she needs help?"
"She's sixteen."
"I'm twice that age, I'm the kid's mother, and, sometimes, I need help
with him."
She had a point, Jerry thought, but he ignored it. "She's babysat many
times before," he said.
"She's never babysat a kid like Dennis."
"You don't know that."
"Yes, I do. There are no other kids like our son."
"How about Dennis the Menace?"
"Not funny."
Their desserts arrived--pudding for Jerry, ice cream for Diane.
"Let's just enjoy our night out, all right? Please?"
Diane dipped her spoon into her ice cream. "All right," she agreed. The
vanilla tasted wonderful.
At their house things were not going well, not at all.
Dennis had barricaded himself in his bedroom, refusing to come out, and
he was tossing paint-filled balloons onto the front sidewalk. Already
he'd dropped both pink and yellow bombs, and the concrete was looking
more garish by the moment. The Spencers definitely weren't going to be
happy.
"Dennis, you open this door, and you open it now," Becky demanded.
"No!"
"Come out of there, this minute, young man!"
"Go away!"
"I'm going to call your mom and dad."
"I don't care. Leave me alone!"
Becky's mind raced. She had to get the brat out of there before he
tossed balloons into the neighbors' yards. It was bad enough that he'd
bombed his parents' sidewalk, but, if he tossed the paint-filled balloons
against a neighbor's house, roof, or garage, Mr. and Mrs. Spencer were
going to be in scalding hot water, and they were going to be furious.
Maybe they'd even make her and her parents pay for the damages or have
her arrested for child neglect.
She decided to try a different tactic. "Come out, and we'll play a
game."
After a moment's hesitation, Dennis called to her through his door.
"What kind of game?"
"Something fun."
"Like what?"
She said the first thing that popped into her head, something that she
and her little brother had done when he was younger. "Dress up."
"Dress up? What's that?"
"We dress you up like a girl." The inanity of her suggestion hit her.
She shook her head, not believing how stupid her suggestion must have
appeared to Dennis.
She was astonished when she heard a piece of heavy furniture being moved
inside her charge's bedroom, and the door opened. Dennis had moved aside
his dresser, and he stood in his doorway, grinning. "That sounds fun!"
On their way home Diane looked worried. She'd tried to refrain from
sharing her anxieties with Jerry, but, she found, she just had to say
something or she'd burst. "I really think we should call home," she
said.
"We've been all through this," her husband reminded her. "Becky must
have things well in hand. Otherwise we'd have heard from her--or the
neighbors--or the police--by now. Relax, honey. Enjoy the remaining few
minutes we have to ourselves. You've earned it. I've earned it. We
haven't been out of the house, or away from Dennis, for months."
"You're right, dear, I know. It's just that--well, I'd feel better if we
could just call and talk to him or to the sitter, and just--"
"No."
"For a minute, that's all, and--"
"No."
She started to become angry, but she knew that Jerry was right. They did
deserve a night out, and, had anything happened, anything extreme, that
is, they'd certainly have heard of it by now. "I guess she does have
things in hand," she said.
"Yes."
"I just wonder what her secret is, how she accomplished such a miracle as
keeping Dennis under control."
"When we get home, we'll ask her."
Becky took Dennis by the hand, leading him from his bedroom, down the
hall, to his parents' bedroom. As he sat on his parents' bed, watching
his sitter, Becky went through Diane's dresser drawers. Although Diane
was in her mid-thirties, she'd managed to keep the girlish figure of her
high school years, and she had several outfits that would look really
cute on her son.
First, though, since Dennis had expressed an interest in dressing up, or,
in his case, Becky supposed, in cross dressing, they might as well do it
right, starting from the foundation up. She chose a pair of frilly
lavender thong panties, silk with lace at the waistband, and a matching
bra. He could wear these underclothes under one of his mom's tank tops
and mini-skirts. A pair of pumps and maybe a clutch purse would complete
Dennis' new look.
She stacked the items, handing them to her charge. "Here. Go into the
bathroom, and put these things on."
As he reached for the articles, Becky remembered the paint balloons. She
didn't want him locked in the bathroom, where, unsupervised, he could do
untold mischief. "On second thought," she instructed him, "just change
here."
His eyes widened and his mouth gaped. "In front of you?"
Becky, looking nonchalant, shrugged. "Sure. Why not?"
"You're a girl!"
"I have a brother just about your age, Dennis," she told him. "We used
to play dress up all the time. You don't have anything I haven't seen
before."
"You haven't seen mine before!"
Again she shrugged. "If you don't want to play--" she started toward
the dresser, the clothing and underclothing items in her hands.
"Wait!"
She turned.
He was looking down, obviously embarrassed. She saw that he was
blushing. "Okay," he surrendered.
Becky handed him the things.
"Aren't you going to turn around?" Dennis asked as he extracted the bra
and panty set from the other items of apparel.
"Should I?"
"Of course."
"Why?"
"I'm a boy; you're a girl."
"We've already been through this, Dennis. You don't have anything I
haven't seen before, remember?"
He wanted to argue, but he was afraid that, if he did, she'd just refuse
to play the game, and, for whatever reason, or, perhaps, for no reason,
he found the idea of dressing up in a woman's clothing sexy, even if the
woman in whose clothes he was about to dress--or cross dress--were those
of his mother. He didn't want the baby sitter to leave. However, he had
a bit of a problem. His penis, which seemed to have no problem letting
him or anyone else know that he was aroused by the idea of wearing
feminine apparel, was stiff and swollen. If he removed his clothes to
don his mom's underwear and outerwear, he'd expose his erect member to
his baby sitter. The thought that she'd see not only his dick, but his
dick in a semi-erect state, was sexy, but it was also mortifying.
"We don't have to play this game," Becky told him, "if you don't want
to."
Dennis blushed. "I do," he stammered, "want to."
"Well, then? What are you waiting for?"
Blushing even more, he set the neat stack of his mother's garments aside,
except for her bra and panties. While seated, he removed his shoes,
socks, and shirt. Then he stood, unbuckling his belt, unzipping his
fly, and removing his jeans. All they while, as he stripped naked in
front of his sitter, he felt the teenage girl's eyes upon him, on his
chest, his groin, his stiff and swollen penis, his thighs. He glanced at
her, and she grinned at him, a lascivious look in her sparkling eyes.
"Turn around, and let me see your butt," she ordered.
Shyly, blushing fiercely, he obeyed her command, offering her a view of
the firm compact globes of his smooth ass cheeks.
"Nice," she said. "Your booty will look very pretty in your mommy's
thong undies."
Dennis' blush deepened as he struggled to fasten the bra's clasp.
Becky pushed his hands away, hooking the fastener for him. "In time
you'll learn how to dress yourself, but tonight, since this is your
first time as a sissy, I'll help you with your bra."
She'd called him a "sissy"! Dennis wasn't sure he liked being called
such a name. He wasn't a sissy. Was he? Sissies were fags; anybody
knew that. Weren't they?
"You're already quite the fetching little girly boy in your lavender bra
and panties set. Silk and lace look good on you, Denise."
Dennis resented her having referred to him as a "girly boy" and her
calling him "Denise" instead of "Dennis," as if he were gay or something.
"I'm not queer," he told her.
"Of course you're not, dear," she said, but her tone suggested that she
really meant the exact opposite of what she'd said.
"I'm not a faggot," he reiterated.
"I said you aren't, didn't I?" Becky asked.
"I'm no homo."
"I know," Becky said. "You're a cross dresser."
Standing before her, in his mother's bra and panties, it was impossible
for him to deny the truth of her last statement, but that didn't mean he
had to like her calling him such a thing.
"A transvestite," she said, "to use the clinically correct term."
"Would you stop calling me that!" Dennis snapped. "Can't you just call
me by my name?"
She patted his fanny. "I'm sorry, Denise."
"I'm Dennis," he shouted, "not Denise."
"Oh? You've decided not to play our little game after all?"
"No. I mean, yes. I do want to play."
"Then you're a cross dresser, a transvestite, a girly boy, and I am going
to call you Denise."
He glowered at her, but the sitter's own face remained passive and
unperturbed. His shoulder sagged. "All right."
"What's your name, Dennis or Denise?"
"Denise," he whispered.
"What's that? I didn't hear you, honey?"
"Denise!"
"That's better."
"But only when we're playing dress up."
"Of course, dear," Becky agreed, but her tone sounded just the way it had
when, in answer to earlier his declaration that he was "not a faggot,"
she'd said "Of course you're not, dear,"--which is to say, ironic, as if
she'd actually meant, by her tone, to suggest the opposite of what she'd
said, namely, that he was a faggot and that he was always Denise, whether
he was wearing his mother's clothes or not.
As he picked up his mother's blouse, Becky said, "Wait!"
He stopped.
"Put that back where you got it," the sitter directed him.
Looking puzzled, Dennis--or Denise--returned the blouse to the stack of
clothing upon the bed.
Becky sat down, her knees folding at the edge of the mattress. She took
Denise by the hand and swung "her" down and across her lap. "You've been
a very naughty girl, missy, barricading yourself in your bedroom,
refusing to come out, and throwing balloons full of paint on your
parents' sidewalk!"
She'd thrown the startled cross dresser across her lap so quickly and
unexpectedly that Denise hadn't had a chance to resist, but, now, he
squirmed, trying to get away from the sitter. He'd had quite enough, he
decided, of this silly game.
But Becky, at sixteen, was bigger and stronger than he, and the teen held
him in place, across her knee. Her hand rose high in the air, slammed
down, hard, against Denise's bottom, which, in the thong panties, was
bare except for the strap running between "her" girly-boy ass cheeks, and
the transvestite gasped, crying out with astonishment and pain.
"How dare you defy me!" the pretty blonde baby sitter castigated her
charge. "How dare you disobey me!" As she rebuked the boy, she spanked
his bare ass harder and harder with each swat. "How dare you flout my
authority!" Slap! Slap! Slap! Her hand fell more rapidly, and a lot
harder, than Dennis would have thought a girl could hit. Becky was
willowy and cute, and it didn't seem possible that such a soft and curvy
girl could pack such a wallop. "How dare you destroy the property your
parents have worked long and hard to acquire!" She must be referring to
the paint balloons he'd tossed onto the front sidewalk, Dennis thought.
"Ouch!" he cried as each slap landed on his reddening behind. "Ouch!
Ouch! Ouch!" He writhed on the sitter's lap, his prick stiff and
swollen, both enjoying the friction and pressure of her sleek, soft
thighs against his burgeoning erection and dreading the next smack of her
hand against his bottom. He also felt humiliated to be lying across a
girl's lap and having his ass spanked by her, especially since he was
dressed like a girl himself, wearing his mother's bra and panties. It
was mortifying--whack!--and painful!
"Stop!" Dennis--or Denise--cried. "I've had enough!"
Becky swatted his buttocks three more times, rapidly, one slap following
another, without a break. "I'll decide when you've had enough, missy!"
The palm of her hand flashed down again and again, filling his bottom
with a fiery agony, and a few small bruises appeared in the cherry-red
flesh. She smiled, upon seeing the contusions, her zeal renewed, and
smacked the wayward boy another five blows that sounded both loud and
sharp. Over her knees, the youngster began to kick and thrash, to writhe
and wiggle, desperate to get away from the punishing slaps the sitter
continued to administer to his bottom. Not until he heard him bawling
like a baby did she stop.
"Get up," she ordered, "and finish dressing!"
He rolled off her, onto the floor, and she saw his hard cock pointed
between his smooth thighs, an incongruous sight, indeed, given the
lavender panties with the frilly waistband and the matching bra festooned
with lace. "Finish dressing?" he repeated her command.
"You don't suppose I'm going to let you run around the house with your
bottom showing, half dressed in a bra and panties, do you?"
He didn't know what to say, so he figured it was safest to say nothing.
However, he did pick himself up off the floor, aware that his sitter's
eyes were studying his erect cock. Hurriedly, he donned the rest of his
mother's clothing. "Next time you'll wear stockings too, Denise, but,
since tonight is the equivalent of your coming out party, we'll forego
that part of your attire. However, you are going to wear a pair of your
mother's pumps."
"Pumps?"
"The low heels."
"Oh."
"Don't just stand there mincing like a fairy!" Becky thundered.
He grabbed the shoes, sat in his mini-skirt, and slipped the pumps onto
his feet. They were a perfect fit, as if they'd been custom made for
him.
Becky picked up a thin volume of love poetry that was stacked with a few
other tomes on the wall shelf above the bed's headboard. She tossed it
across the room. "Fetch that book. You need to practice walking in
heels."
Denise rose, looking none too sure of "herself," and stumbled across the
room, nearly falling twice on the way to the book and three times on the
way back. It was sheer hell, just bending over to retrieve the volume,
he thought.
Becky giggled. "You have a lot to learn, missy, but that's okay. We'll
work on your walk, just as we'll work on your makeup, hair, gestures,
speech, and everything else. When I'm through with you, you'll be as
much a girl as if you'd been born with a cunt and tits instead of a cock
and balls."
Such talk! Denise wouldn't have believed that the wholesome-looking
sitter knew such words.
"Now that you're decently dressed," Becky said, "we're going outside, and
you're going to--"
"No way! I'm not going anywhere dressed like this, and especially not
outside."
"It's your choice, Denise: outside, or back over my knee, and, this time,
I won't stop until your ass is a bloody pulp."
They were outside, with Denise using a wire brush and paint thinner to
scour the paint off the sidewalk, a bag of rags nearby, when the Spencers
drove up.
The couple hastened across the lawn.
"What's going on here?" Jerry demanded.
"Why is our son wearing my clothes?" Diane enquired.
Becky explained that Denise had been a very naughty girl, tossing paint-
filled balloons from her bedroom window. She'd barricaded herself in her
room, Becky reported, and had refused to come out when the sitter had
ordered her to do so. "I'm sorry about the sidewalk, Mr. and Mrs.
Spencer," she apologized.
"But why is Dennis dressed like this, in my blouse, mini-skirt, and
pumps?"
"Not 'Dennis,' Mrs. Spencer. 'Denise.' She's also wearing your lavender
bra and panties set."
The couple's mouths dropped open, but neither said a word.
"Denise is being punished," the sitter told them, "the same way my mother
used to punish my little brother, Drake. It's an old-fashioned method,
but, as you can see, it's highly effective."
Neither parent contradicted her statement.
"It's known as petticoating, or petticoat punishment. Sometimes, it's
accompanied by a spanking, as it was this evening."
"You spanked my boy?" Jerry asked.
"Yes, sir. In this case, I thought a spanking was in order as well as
the petticoating. Denise was insubordinate. She was destructive of your
property. She was disobedient. I had to assert myself. I had to take
control of the situation--and of Denise."
The Spencers exchanged uncertain glances.
"I hope you'll have me back," Becky said, "as your sitter. You're a nice
couple and good parents. I'd like you to be able to get away once in a
while and enjoy a little time alone, just the two of you. Besides, I'd
like to continue training Denise. I think you'd be very pleasantly
surprised at how effective petticoat discipline can be in curbing the
rude behavior of impudent boys."
"Well," Jerry ventured, "I've certainly never seen any other sitter
control our son."
"I'd appreciate it if you'd refer to Denise as your 'daughter,' sir, at
least while she's dressed as a girl."
"Sorry, I meant my 'daughter.'"
Denise rose onto her knees, staring at her father in disbelief. "Dad!
I'm a boy, not a girl! I'm your son, not your daughter!"
"Ignore her," Becky said.
"I don't know about this," Diane said. "I mean, isn't treating our son
like a girl likely to have an effect on his--I don't know--self-image,
identity, sexual identification?"
"Denise wanted to play dress up, Mrs. Spencer," Becky reported. "Your
'son' is a cross dresser."
"Dennis! Is that true?" Diane cried, aghast.
"'Denise,' dear," Jerry corrected her.
"Is it?" Diane demanded.
"Yes." It was a one-word confession, said with such utter simplicity
that Diane and Jerry knew, the instant they'd heard it, that their "son"
was, indeed, a transvestite.
"You don't have anything else to, uh, share with us, do you, Denise?"
Jerry asked.
"Like what?" Denise asked.
"You're not, uh, gay, are you?"
Denise blushed. "No, Dad!"
"Most transvestites aren't, Mr. Spencer. It's possible Denise is not."
"I'm not!" Denise insisted.
The sitter sighed. "Of course, it's possible that she is, too."
"I am not gay!" Denise cried.
"We'll just have to wait and see," Becky suggested. "One thing I can
tell you for sure, though, is that cross dressing won't, in and of
itself, make her homosexual."
"I'm not homosexual!" Denise screamed.
Afraid what the neighbors might think, should they hear her son's
protests, Diane shushed Denise. "For God's sake, lower your voice! Do
you want the whole neighborhood to know?"
"Know what?" Denise cried. "There's nothing to know. I AM NOT GAY!"
"It's okay if you are, dear," Jerry consoled his "daughter."
Denise sobbed. "I'm not, I'm not."
"It's okay, sweetie," Diane assured her child. "We love you no matter
what."
Becky's tone, when she spoke to Denise, was equally kind. "You just
finish your chore, and then you can go inside with your mom and dad and
watch a little TV, if you want, or shave your legs and take a long, hot
bubble bath. You've had a long day."
"Here's your pay," Jerry said, handing the sitter twenty dollars.
"Thank you, Mr. Spencer."
"And a bonus," he said, handing her another twenty.
"Oh, I couldn't--" she protested.
"Please, dear," Diane said, "take it. It's little enough after all
you've done."
Becky smiled. "All right. Thank you." She tucked the money into her
cleavage. To Denise she said, "You go along with your parents now,
dear. Take the brush and the paint thinner and the bag of rags with you,
and freshen up. I'm sure you and your mom and dad have lots to discuss."
Denise did as she was told, sniffing and sniveling as she hastened into
the house.
"Actually, she looks pretty good in my things," Jenny observed.
Jerry chuckled.
Becky looked at her house, across the street. The lights were out,
except the one on the porch, which had been left on for her. "I guess
I'd better be going," she said. "My parents worry if I'm out too late."
"We can't think you enough," Diane said, squeezing the sitter's hand.
"I'm glad I could help," Becky said.
"Do you think you could baby sit for us again next Friday?" Jerry asked.
"I'd be happy to," the sitter said. "I'm dying to see what Denise looks
like in Mrs. Spencer's apron, wearing a pair of real heels."
Diane and Jerry laughed.
"Call me anytime," Becky said, "anytime at all."
"Thanks. We'll take you up on that--often."
The sitter walked down the sidewalk, crossed the street, and disappeared
inside her house. The porch light went out, and her front yard went dark
beneath the moonless, starless nighttime sky.
Jerry took Diane's hand in his, and they walked together, side by side,
feeling like a young couple on a date instead of the parents of an
adolescent who loved dressing up like a woman and who may or may not be
gay.
Liesl
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