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Message-ID: <57374asstr$1204463404@assm.asstr-mirror.org>
From: "Leo Wulf" <leowulf@gmail.com>
Subject: {ASSM} Sitter (FM, femdom, rom, lac, mast, inf)
Lines: 472
Date: Sun, 02 Mar 2008 08:10:04 -0500
Path: assm.asstr-mirror.org!not-for-mail
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Newsgroups: alt.sex.stories.moderated,alt.sex.stories
Followup-To: alt.sex.stories.d


Sitter (FM, femdom, rom, lac, mast, inf)

by Leowulf

In which a man hires a sitter for an evening's child care.

1.  Warning:  the first three rows may get wet
2.  As usual, no reposts except to ASSTR or Usenet
3.  Send Feedback!  Leowulf "at" gmail "dot" com.  Let me know what you like
(or dislike) about my stories.  :)

--

Nanny

"Thanks alot, Jake,"  Trixie smiled at the limo driver.  "I'll give you a
call when it's time to come pick me up."

Trixie Tata hated her name.  If there was anything that shouted "hooker"
louder than the ridiculous outfit the company dressed her in, it had to be
that name.  She was born Elizabeth Chastity Chandler, but the company didn't
like any of those names.  Especially the middle one.  They told her in no
uncertain terms that she'd go by an pseudonym that they would choose for
her, based on her physical attributes.  And apparently they'd chosen an
outfit to show them off as suggestively as possible.

"I'm from HTE Services," Trixie spoke into the intercom at the door of the
modest house. "Here for Robert Wells."

She'd been with Hot Times Escort Services for 3 weeks, and had served as
many clients.  None of them was pleasant.  The first was a drunken sot who
attempted to force himself upon her.  Girls with the company could choose to
have sex or not to, but the company strongly advised them to do whatever the
client wanted.  It didn't happen that night.  Her next client ordered her to
writhe about in front of him and express milk through her shirt.  He ordered
her to have sex with him too, but he was too arrogant for her tastes.

"Mr Wells?"  Trixie was irritated at the delay; a freezing rain made the
night unbearable.  "HTE Services, sir."

Her third assignment was a New Year's Party.  As with the other two, she was
chosen for her large breasts.  She did a strip-tease for the businessmen and
thrilled them with the fact that she was lactating.  It always surprised her
that men were so captivated by girls with big breasts, and how that
increased so much when the girl in question could produce milk.  'Men are
boys' was an accurate saying.  These men had left their sweet boyishness
several martinis ago.  She ran when they mobbed her.

'Oh my; he's been crying.'  Trixie felt an inexplicable worry for him.  "Mr
Wells, are you okay?"

"I'm sorry for keeping you waiting, ma'am."  The man blushed.  "I was still
debating whether or not to do this."

'Okay,' thought Trixie.  'So is he still debating, or do I move things along
and collect my pay?'

"Why not invite me in."  The thought of her pay decided the issue for
Trixie, if not for her client.  "We can talk about what you were thinking
about, and decide together if we should do it."

"Oh!  Of course."  Mr Wells nodded and stood aside for her to enter.  "Would
you please come in?"

Trixie stepped in out of the cold, rainy evening.  Looking around, she had
the same opinion of the house as the man.  Each was small, so tidy that they
seemed uncomfortable.  Like Mr Wells' crisp business suit, the house looked
professional to the point were neither would tolerate comfort or ease,
tonight or ever.

The woman unbelted and removed her heavy raincoat, enjoying the expression
on the man's face when she revealed her charms.  The look of wonder in his
eyes was actually worth the hooker outfit.  His ogling seemed less predatory
than the others.  She gave him a second, then said, "Would you please take
my raincoat?"

He gingerly hung up the raincoat on a hook outside the closet door - of
course he wouldn't get the things inside wet.  Now was as good a time as any
to get the payment out of the way.

"You contracted for 4 hours, Mr Wells."  Trixie had learned over the past
three jobs that short and direct was best.  "That's 400, and it's paid up
front, and regardless what happens.

She added that last part just in case the man's indecision had a monetary
component.  But the man had already provided his credit card, and he signed
the invoice without hesitation.

"Now that that's taken care of," Trixie said, placing the carefully folded
invoice into the inner pocket in her belt.  "Let's sit down together, Mr
Wells.  You can tell me about what you've been considering, what it is
you're debating about us doing.  And we can decide together if it's
something we would like to do.

She settled herself in the overstuffed sofa.  Like the matching loveseat and
chair, it was a neutral color and looked as stiff as a board.  But sitting
on it was comfortable, and settling back in it was so nice; it was like
resting on a feather bed.  It had a warm, womb-like quality.  'I could get
use to this,' she thought.

Mr Wells chose the stiff, high-backed chair opposite the sofa.  He looked
alert and professional.  Ready to talk business.

'Oh my; doesn't he ever relax?'  The slight worry she felt earlier came back
in force.  'Does he even know how to relax?'

"Mr Wells," Trixie picked her words carefully.  She had the feeling he was a
bird who would fly away if threatened.  "I would feel much better talking
with you if we sat together."  She petted the sofa cushion next to her,
saying softly, "would you please sit with me, sir?"

The man hesitated a few seconds.  It felt like an eternity to Trixie, and
she was sure he'd turn her down and turn down the whole evening.
Technically, it didn't matter; he'd paid and the company didn't care about
anything else.  Therefore nor should she.  But she did care.

Finally, he got up and slowly moved around the big coffee table toward her.
His eyes looked wary, nervous.  A shy deer, a rabbit perhaps.  He sat on the
sofa next to Trixie.  She exhaled, only then aware that she'd been holding
her breath.

"I'm afraid I don't know how to say this."  The man blushed again.  He
looked so conflicted.  Trixie wanted to hold him, but it was obvious he'd be
frightened and run away.  "And I'm not sure you'll be impressed if I did
talk about it."

Trixie reached out slowly, carefully, keeping eye contact.  Still, he
flinched when she took his hand.  She felt bad to frighten him, even a
little, but she was certain physical contact would help him absorb her
words.  "Mr Wells, this is very important."  She kept her voice soft,
soothing.  "I will never think of you as a bad person, no matter what you've
been thinking.  You can tell me anything, and I will still ... respect you."

Trixie frightened herself a little with that speech.  Not from what she
said, but from what she avoided saying.  'You can tell me anything, and I'll
still love you.'  What the hell was wrong with her?  She was getting too
attached to this fussy little man.  This shrimp was too uptight to lose his
business suit even for a date.  She didn't know shorty; he might even be
crazy.  Still, she was glad to notice he left his hand in hers.

"Well," he began.  He broke eye contact, but still let her hold his hand.
"I've always had this dream where I'm being cared for."  The blushing,
bashful man was so endearing.  "By someone, um ... well, like you.  So
gentle and so pretty."

Trixie smiled.  The small man's simple praise made her feel far more
desirable than the wolf whistles and cat calls that other men she'd met had
bestowed on her.

"Cared for."  Mr Wells had a faraway look as he continued.  "Fed and held
and ... well, just cared for.  Like I'm her own."

"What a wonderful dream."  Trixie said, gently giving him her affirmation.
Giving him permission to tell the whole story.

"So last week I retired."  His joyful reverie seemed to be shattered by his
statement.  "'Was bought out' is more accurate.  A hefty severance package
and goodbye."

Trixie sat next to Mr Wells, feeling so sad to see tears rolling down the
man's cheeks.  How she wanted to hold him, to comfort him.  But she could
feel that he was not yet ready for that.  She settled for squeezing his
hand, ever so gently.

"The loss of what I'd worked for," his voice was quavery, but the brave
little thing continued.  "It really hurt.  A lot.  And now I don't know what
to do, where to go."  Mr Wells stopped, tears trickling down his cheeks.
Now Trixie put her arms around the small, overdressed man.  She held him to
her bosom.  Her shirt was moist; the little dear's crying had made her milk
let down in response.  A thought occurred, but she set it aside for now.

When her warm embrace and gentle, maternal cooing had calmed him enough, Mr
wells said the rest.  "I had nothing left but my dream.  I thought if
someone would care for me, just for one night, maybe I could go on.  One of
the guys at work used HTE Services.  I'd overheard him say they employed
ladies who could meet anyone's needs."  The man's embarrassment won out over
his grief.  Blushing he said, "though he phrased it much less politely."

Rocking the man gently in her arms seemed to calm him.  No longer upset, he
was deeply despondent.  "So there you have it."  His voice was so small,
Trixie strained to hear him.  "Your date isn't a big, rich man; he won't
sweep you off your feet.  He doesn't even want sex, only to be taken care
of.  I know how that sounds, and what you must think.  You can go now."

'He just dismissed me.'  Trixie was irritated - more than irritated.
Hormonal or not, she would not let this little boy in a man's suit send her
away just because he didn't feel he deserved her.  She let go of him, moved
around him to sit on the coffee table, her legs on either side of his,
squeezing them gently.  Her hands took his in a firm, if gentle, grasp.

"No!"  She said, forcefully enough to surprise both of them.  "In the first
place, I will come and go here whenever I want, little boy.  That's not your
decision to make."  She kept squeezing his with her own, gently, hugging him
peripherally with hands and legs while she scolded him.

"In the second place," she leaned close, made herself speak more slowly.
"You never tell me what I must think.  Ever.  In fact, little boy, you never
tell me what to do.  Ever.  That's not your decision either."  Trixie's
heart broke to see the shocked man weeping again at her words.

She let him cry a second, an eternity, then pulled him forward, onto his
knees in front of her.  she held his head to her breasts, wrapped her arms
around him, murmured soft comforts to him and let him cry.  When he was
done, she took a tissue from the plain, serviceable holder on the table.
Putting it to his nose, she said, "blow," and he did.

"Now."  Trixie pushed the man away, far enough for their eyes to meet.  She
still hugged his sides with her legs, kept one hands on his shoulder, the
other drying his tears and smoothing his messy hair.  She wanted to hug the
meek little man, snuggle him in her bosom.  But first he had to understand
something, the basis for their relationship.

"Just so you know, I could have a big, rich man.  I had a room full of them
last week, and all of them wanted to fuck me."  The profanity was a
calculated risk, carrying shock value while hopefully not moving him from
the delicate emotional place she'd put him in.  "I could have become wealthy
as a sex object."

"But I don't want to be some rich man's sex object."  Elizabeth Chastity
Chandler realized she was speaking to herself as much as to the little boy
in the big man's suit.  "And really I don't want a big, rich man; I'm sick
of them."  Keeping eye contact she said, "I want a little boy to care for.
I want you."

"Now, Mr Robert Wells," Beth said, smiling again.  She'd subjected her small
boy to some intense communication, not all of it pleasant.  She'd had a
small epiphany herself and was not sure what to do about that.  For now, she
wanted to play, and her small boy had probably needed to play for years now.

"We have to talk about only two things and then we'll get to play."  Beth
took her boy's little hands in her own.  "First, you are not Mr Wells; Mr
Wells worked for some big company.  You are not Robert; Robert is some big
man's name.  You're not a big man."  She kissed one small hand.  "You're my
little boy, and I'm naming you Bobby."

"Second, my name is Elizabeth Chandler.  I go by 'Beth.'  People will call
me by my name so you need to know who they mean."  She smiled; her child had
a good attention span.  "To your friends I'm 'Ms Beth.'  And to you I'm
'Mommy.'"  She kissed his other little hand.  "Remember, little boy:  I'm
your Mommy.  You call me Mommy."

The lady let go of her Bobby and stood.  The sudden motion surprised the boy
and he stayed there on his knees, between her feet.  "Do you understand,
Bobby?"

Beth's little boy looked up at her.  For the first time since she saw him,
Bobby didn't look stiff or uncomfortable; he looked happy.  "I Understand,
Mommy!"

"Good boy!"  Beth knelt down and pushed her child back onto his back on the
soft carpet.  "Now we can play!"  With swift hands, and swifter fingers, the
new mom tickled her new little boy under his arms and on his tummy and on
his knees.  She laughed at his delighted squeals, and they both laughed
together for sheer joy.

"Okay, now hold still, honey."  Still straddling Bobby, Beth stroked his
small chest and his ruddy cheeks, helping him calm down from her tickling.
When he was down to an occasional spontaneous giggle, she lifted one of his
short legs and started untying his hard, dress shoe.

"Um, um." the small man put his hands on hers, to stop her from untying his
shoe.  "Beth, please no."

Beth put her hands gently atop the man's smaller hands, letting him hold his
shoe tied.  With an enticing smile, she asked, "what's my name, Bobby?"

"Mommy," the man blushed, smiling despite himself.  Beth knew she'd never
tire of her child's smile.

"But you don't want to take off my shoes; I'm nervous and sweaty."  Beth
gently pulled his other leg up and held it with his first one.  She'd
expected this battle; the big man her small child had tried to be wouldn't
just vanish.  They'd have to work together to be rid of him.

"Bobby," Beth asked, her face very serious.  "You said you wanted to be
cared for.  Is that what you still want?"

The man just nodded, his inner conflict clearly evident in his worried
expression.

"I want to care for you too."  She held the man's feet up, his knees bent,
as though she were changing his diaper.

"For that to happen, I have to be in charge of you."  Beth stared into his
eyes.  "Would you please trust me, Bobby?  Would you trust me to be in
charge, so I can care for you?"

He nodded again.  Beth was so proud; Bobby's bravery - and maybe trust in
her - was stronger than his embarrassment.

On an impulse, the young lady sang to her boy, distracting him, keeping his
attention on her, and not on what her hands were doing.  In short order,
socks and shoes were off.

Beth wanted to just work up from there, but the man inside the boy was still
there, waiting to shut this whole thing down.  Exposing Bobby's private
parts before he was ready would be just the excuse he needed. She'd have to
work around him.

"Come on, Bobby," Beth's soothing voice was making her little boy so happy,
and that gave her a sense of satisfaction.  She lifted him up to a sitting
position.  Still murmuring softly, kneeling with her legs on either side of
his, she loosened and removed his tie and helped him out of his suit
jacket.  "That's Mommy's good little boy."

"Now, this little piggy went to the market."  She made a game of unfastening
the buttons on Bobby's shirt.  By the time she got to the fifth and last
button, her boy was giggling.  "And this little piggy went 'wee-wee-wee all
the way home!"  She punctuated her nursery rhyme with tickles on his tummy.
The dressy shirt fell off unnoticed.

"There, there," Beth cooed.  She hadn't even started on his undershirt yet,
but she wanted to keep her little boy a little boy, not alert the man of her
plan until it was too late.  "What a good Bobby.  Mommy's good Bobby."  She
gently lifted the shirt, while still talking to him, and in a smooth motion
held him to her, his bare skin against her shirt, his head snuggled between
her milk-full breasts.

She knelt there with him, holding him to her breasts, snuggling him, keeping
him feeling safe and warm.  And loved, she briefly thought, but she didn't
dwell on that.  She was fascinated at how her big huge tits had made her a
desirable sex object for her clients, but for her baby, those soft breasts
made her a comforting mom.  She climbed up onto the sofa, gently guiding her
child onto her lap.

"Oh, what a good boy."  Beth snuggled him once more to her breasts, meeting
eyes that held only trust and love.  "Mommy loves her little Bobby."
Ignoring the warning bells that went off inside when she said that, she
unfastened her boy's belt and pants.  Her hands were gentle, her movements
slow.  She kept her eyes on his and murmured reassurances.  She lifted him
and slid his pants off his short legs.

"Mmmm," Beth cooed.  "What a wonderful baby."  She looked down into his eyes
still, as she opened her blouse - well, the racy top that served a purpose
similar to a blouse.  The singular advantage of the not-quite-clothes she'd
been made to wear was that she didn't have a bra to she'd need to unfasten.

"Um, Beth."  The man's eyes widened at the sight of her breasts so close to
him.  They widened comically when he noticed his private parts exposed to
both their view.  He quickly put his hand over himself, not quite hiding his
erection from both of them.  The man repeated  his objection.  "Beth, no!"

'Oh my!'  Beth was inwardly irritated.  'That ... that man is so
persistent!'  She allowed herself a sigh; anything more might frighten the
child inside the man.  'At least he isn't as strong as he wants to be.'

The young lady wrapped her arms around his shoulders, pinning his arms in
place.  Also keeping his face inches from hers.  She hooked a leg over his
own, keeping him from leaving. She ignored his irritated struggling, ignored
his sharp protests.  In fact, she ignored the man completely, just kept him
still and let him exhaust himself.

"Bobby."  Beth soothed.  "Bobby.  There, there."  She moved from words to
just soft maternal sounds.  Beth felt an inner satisfaction as the man's
struggles finally began to abate, his strongly worded protests dying down.
When the distraught boy at last responded to his plight with tears, she was
ready.

"Mommy's here, Bobby."  she kissed the top of her small boy's head.  "It's
frightening to give up control."  She rocked him in her arms.  "And it's
always okay for Bobby to cry when he's afraid."  Beth held her child to her
breasts, and whispered more comfort and encouragement.  "It's hard to give
up control, but you're doing so good."

"Mommy's here for you," Beth told her quiet little boy.  "Mommy loves you,
precious."  She kissed him again, on the forehead, and when she said it
again, she was admitting it to herself.  "Mommy loves her Bobby."

Nursing her baby was the most natural thing to do then.  His mouth was
already against her stiff, crinkly nipple.  Beth pushed her whole aureole
into his mouth.  His mouth was full of her breast, and her breastmilk.  When
Bobby swallowed, the suction drew more of her milk into his mouth for him to
swallow.  The nursing baby held her breast in small hands and looked up into
Mommy's eyes.

Beth sighed at the delicious pleasure of her baby suckling her, squeezing
her nipple and aureole, holding onto her breast.  Bobby's eyes were wide,
drinking her in.  They sat like that, staring into each other's eyes, while
Beth told her dear little baby how much she loved him, while she fed him her
breast.  When she felt him stirring, she broke the suction with a finger and
switched sides.

Bobby didn't need any encouragement.  Her baby's mouth found her breast and
he stuffed as much as he could into his mouth.  Beth shuddered at the
wonderful feeling of her baby's mouth kneading her aureole, massaging her
nipple.  Sucking her breast.  Filling his tummy with her breastmilk.  With
her.

Looking down at her baby, Beth was not surprised to find his penis sticking
straight up.  She was a little sad to see he was circumcised; she didn't
like the thought that he'd been in pain, even for a few moments as a
newborn.  But that was long ago.  Now Bobby had Beth to care for him.

Smiling beneficently at her baby, she licked her fingers.  Spilled her
saliva into her hand.  Wrapped her wet, slippery fingers around the child's
erect penis.  Smiling wider, when his eyes widened.

Beth was doing more than just expressing her love to her child; she hoped
she was making peace with the man also.  Her fingers promised real and
immediate reward whenever he gave up control to her.

Her baby wriggled happily in her arms as Beth lovingly massaged his erect
penis.  He kept nursing.  His expression held such joy that Beth almost wept
for joy herself to see him.  The new baby stiffened and arched his back as
the new mother brought him to orgasm.  Then she wiped him and herself clean
with the suit pants her boy used to wear, before he met Beth.

Bobby wasn't paying attention to Beth making him clean and dry, nor what she
used to do so.  He was full, sated.  Beth stroked his distended tummy and
her baby giggled happily.  Then she sat the boy up, rubbed his back gently,
and praised Bobby when he finally burped.

The man looked up at her.  He said, his voice rapturous, "You're so
wonderful."  Blushing he added, "Mommy!"  Beth held him close to her. She
couldn't help weeping for joy.

Beth lay her child on the sofa.  The once-fussy man didn't complaint.  He
curled up next to her, his head pillowed on her thigh.  He put an arm around
her leg and kissed her hip.  That reminded her of her fish-net stockings.
She was glad she wouldn't need them next time.

The young mother stroked her child's hair, murmured her love to him, rested
her hand on his small shoulder.  When she was satisfied he was asleep, she
moved slightly.  Keeping her little love still snuggling one leg, she lay
another across the wide, cushiony arm of the sofa.  She licked her fingers,
though there was no need for that, and played with herself.  She was so hot,
so wet.

Beth thought about the small man, the small boy, the small baby curled up to
her thigh.  She was so turned on by him.  She slipped her fingers in and out
of her vagina, rubbed her clitoris, sighed with pleasure.  She didn't mind
the man; as long as he surrendered control to her, she knew he could be very
sweet and considerate.  They'd become the best of friends.

Beth kept her thick fingers dancing over and insider her yoni.  She panted,
rather than keened, wanting to let her Bobby sleep.  She absolutely loved
the boy.  Yes, damn it, loved him.  Ever since she saw him under the man's
facade when he opened the door to her.  She wanted to care for him, not just
to fulfill his fantasy.  She wanted to become his mother.

Beth came like an earthquake.  Waves upon waves of ecstasy washed over her.
She shuddered with the intensity of her orgasm.  Smiled a little guiltily
when her Bobby stirred.  She kissed her fingers and lay them against his
cheek.  "It's okay, precious," she murmured contentedly.  "Mommy's here."

Beth carefully got up, leaving her Bobby sleeping on the womb-soft sofa.
She cleaned herself with the jacket of the suit he used to wear, before he
met her.  She'd have to be careful when she changed his wardrobe.  Be extra
sweet to the man, but remind him who was in charge around here.

Later, with her Bobby covered by a plain, serviceable blanket - she'd need
to get him fuzzy ones to suit his new childhood - and with his spare keys
safely on a chain around her neck, she called her driver.  The modest Wells
estate was a bit far from HTE's offices, so he'd take a while.

While she waited, Beth made herself a cup of tea.  Using her Bobby's plain,
serviceable stationery, wrote two letters, both to be read in the morning.
One was to her Bobby; she loved him and she'd be back the day after
tomorrow, at noon sharp.  She and her wonderful boy had a lot to talk
about.  The other was to HTE; Trixie's letter of resignation.  She had
nothing more to say to them.
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