Another Baby Sitters Tail
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This story's been around for a long time, in many versions. Here's mine:
ANOTHER BABY SITTER TAIL
"The baby sitter will be here soon," called Leroy's mom from the
other room. House bound and frustrated, he scowled. Although the
babysitter was for his 1 year old sister, he knew he'd be told, "Treat
her as a guest." He couldn't leave, and he had to be NICE! YUK! It
The doorbell rang as Leroy's mother stuffed her grape-fruit size
boobs into a sheer bra. Leroy liked to watch his mom dress. At 35
years old, she still had a bod that guys his age dreamed of porking.
It made his peter twitch. He looked away to get a good look at the
duchess as the door opened. "Hello, Debby," he heard his mother say.
The 20 year old girl was quite slender, with long dark brown pigtails
caressing her chest. She wore a short skirt, which emphasized her
narrow hips and meaty buns, and oversized sweater which did little to
conceal an abundance of sweater meat.
"Hello, Barbara," said Debby. "Leroy," summoned his mother.
Leroy approached the women. "This is Debby and I want you to be
especially nice to her while she is taking care of your sister."
Yup, Leroy had seen this coming. He was to be "nice." Almost as
though she was in charge... bitch. But it might not be too bad.
Debby was more than attractive, she was downright sexy.
"Hi, Leroy," intoned Debby.
"Yo," chirped back Leroy.
After his mother headed out the door, Debby took off her sweater.
"I'm going to check on the baby," Debby announced to Leroy. "You want
to play Monopoly? Do you want to? Huh?"
Leroy shrugged and headed for the closet.
"C'mon, Leroy, let's make the best of it," smiled Debby as she
left the room. She can read minds, too, Leroy said to himself as he
dug through Scattergories, Yahtzee, and Life.
Debby and Leroy squatted in the living room, moving the pieces
around the board, buying property. Debby would occasionally give him
an acknowledging smile or nod. Leroy's mind was elsewhere. Would she
put out? She was pretty, and her tits were really provocative. They
looked swollen, maybe too large for her small frame. Wondering what
they looked like, he searched her chest to locate a nipple but only
found large wide swells, a little more on top than right in front.
His mother's nipples were large. He'd seen them from time to time as
she nursed his sister. He wondered if Debby's were puffy and big and
if she let her boyfriend play with them. Probably not, he mused; she
was probably content to drive all the guys crazy.
Debby asked if he had a girlfriend. Plenty, he lied. She asked
what he thought of having a baby sister in the house. What kind of a
dumb question was that? Fine, he replied facetiously, trying to
maintain a cool air. Debby laughed. As she did, a crying emitted
from down the hall -- the baby.
"Oops, feeding time," announced Debby.
"Great" Leroy responded with more sarcasm.
"Want to watch?"
"Oh joy! Sounds like fun."
"Don't be such a shithead. Keep me company. It'll be fun, I
promise" Debby said with a wink, then started down the hall. "Grab a
towel on the way, OK?" Leroy obliged, and found Debby picking up the
infant when he got to the baby room. She cuddled the child in her
arms; she knew just how to hold it. Instead of getting a bottle,
Debby lifted her cutoff tee-shirt revealing a pure white swollen
breast. It was a perfectly round orb not unlike a ripe Florida
grapefruit. The nipple was covered by a band-aide, or so he thought.
With startled expression, Leroy asked "What the hell is that?"
Peeling it off, she said "This? It's a MaxiMinimizer. Girls who
don't like wearing a bra but don't want to look braless use these to
keep their nipples from poking through their clothes. They're great
for nursing, too. It minimizes stimulation between feedings, keeping
your clothes dry."
Leroy was far more interested in what she was exposing. A huge
chocolate nipple, much bigger than even his mom's! Debby raised the
baby to her big left breast, and guided her mouth toward the bloated
nipple. She tickled the infant's mouth with the wet, inflamed end.
When the baby opened its mouth, Debby plunged the thick nipple into
its mouth. The baby almost gagged.
"Can you hand me the towel, Leroy?" dripped her sweet sandy voice.
She put the towel under her big breast, so the milk wouldn't spill on
the floor. Leroy was in a state of shock. "Um, wh-what are you
doing?" he stammered. "I'm nursing her," Debby replied, matter-of-
factly. "You do understand what nursing is, don't you?"
Leroy nodded faintly. "But I thought you had to have a baby to do
that." "No, not really," she said, looking down at her suckled breast.
"Any girl can do it if she wants to. All she needs is regular nipple
stimulation. Mom started me years ago after my first period, when she
remarried and had twins. She didn't have enough milk for both of
them, so she started me nursing too. Now she babysits a bunch of
neighborhood kids, so, it's like, she needs me. All it takes is for
one of them to fall down and cry, and then you've got a whole roomful
of two- and three-year-olds crying at once. It's a mess! But
usually, I'm laying out in the backyard or something, and she calls
me. I just take off my bikini top and take one kid at each boob and,
between us, we've got the whole room quiet again."
Debby looked down at Leroy's infant sister, who had fallen asleep.
Debby lowered her voice as she gently extracted her nipple from the
baby's mouth. "Besides, it's kinda fun and it feels reeeeally good,
too. And seven years of nursing has made my nippers kinda big, don't
you think?" She threw back her shoulders and thrust out her chest
Nodding for sure, his eyes were glued to the jumbo nipples almost
popping off the pointy titties.
"Anyway, nursing makes my boobs bigger and heavier, and I know
guys get turned on by big firm boobs." She smiled, gently caressing
the boobs with her hands.
Returning to the living, Debby sat on the couch cross legged,
opposite Leroy. Leroy quickly noticed that she wore no panties.
Leroy's mouth was dry and his pulse racing. Was she oblivious to what
affect she was having on him or just teasing? He glanced to his lap
to see if it was obvious. It was.
"Leroy," she said kind of shyly. He looked up with a start. "Hey,
um, I've never nursed anyone who isn't a baby, you know? And so I was
wondering if you might like to try it and we can see what it's like.
Me nursing you, I mean." She was smiling, a little awkwardly.
Leroy felt hot and light-headed. But something wouldn't even let
him stop to think about it. As he moved towards Debby, she gently
raised her tee-shirt and pealed both MaxiMinimizers from her tits.
"Hey" she whispered, "take your pick, or take both, they're both OK."
He leaned down to Debby's chest, feeling his heart pounding in his
neck. He surrounded the warmth of her ripe breasts with both hands.
They were so white against his hands. He gently squeezed and the
nipples swelled even more. Kind of like squeezing a balloon, he
thought. He traced his finger around a nipple and marveled at the
size of the dark areola. It was easily 2 inches across. Nervously,
taking in just the tip, he sucked. Nothing! He kept sucking. He was
"Leroy," she said gently, "take all of it in your mouth, even the
areola, you know, the dark puffy patch at the base of my nipple right
here. Suck hard and nibble on my nipple with your teeth and tongue.
You won't hurt me."
He sucked her areola, and sucked hard. Streams of warm, sweetly
sour milk squirted into his mouth. Debby purred softly and put her
hand behind his head, holding him to her.
"It's not that I really wanted to do anything with you," she said,
gasping slightly. "I just wanted to try this." As he nursed Debby's
tit, Debby's hips beginning to rock and grind, releasing a heady
aroma. While Leroy contemplated making a move to explore her crotch,
Debby lowered her hand to his crotch. It strained against his jeans,
too confined to reach full length. "Sorry, I didn't mean to..." She
lied, but made no attempt to remove her hand. She was quite impressed
with what she felt. "Good god, Leroy, is that all you? I've never
felt anything so big!"
Just shrugging his shoulders, Leroy said "What else would it be?"
She took his hand and placed it up her skirt, onto her warm
uncovered crotch. This wasn't the first time he ever touched a girl's
privates, but he really had little experience and most of that was
accidental and awkward. But he clearly knew what he was touching
without even seeing it. The vision of it was imprinted in his brain
from countless girlie magazines. He found her clit and gently pulled
and rubbed between his fingers. It felt much bigger than he imagined
it would. Locating the eager mouth to Debby's moist passion pit, he
parted the swollen lips and worked his middle and ring fingers deep
into the heated cavern. Amazed at the copious wettness, he could
actually hear the gurgling and sloshing of her juices as he wiggled
In spite of his awkward manipulation of her ripe womanhood, it was
having a devastating affect on Debby. "Oh Leroy... yes, that's it...
it... feels sooo nice." A few minutes later, totally on fire, Debby
suddenly broke it off to remove all her cloths. Standing before him
in her flushed nakedness, Leroy choked. Debby's petite body was
awesome, real centerfold material. "Leroy," she gushed, "don't make
me beg. Let me see what's in your pants."
His hands were shaking, but he got his zipper down. His dick
wasn't fully hard because it was too confined, but it was still too
big to come out on its own through the small opening. Leroy wrestled
his pants down freeing his cock and balls to the cool air and Debby's
Leroy's cock was pretty big, even when soft, at 8 inches long and
almost 2 inches thick, it was bigger than most of the older guys he'd
seen in his gym showers. With each nut the size of a goose egg, his
cock and balls filled a swim suit to overflowing, often embarrassing
him by the stares it attracted. He often mused how it looked when soft
like a heavy blackjack, the glans peeking from the thick foreskin, and
when hard, like a big black zucchini. But until now, he really didn't
know just how big his boner was compared to others.
Her eyes told him... they bulged. "Gawd! I never ...gawd... it's
so fucking big!" She gasped. "It's as big as my forearm." Grabbing a
testicle in each hand she tongued the hole at the end of his penis and
slowly sucked the monster glans in her mouth. Her mouth strained at the
incredible thickness. She drooled, "you've got to give it to me NOW!"
In a blink, Debby was lying on her back, spreading her legs around
his trunk. Holding his cock, she guided it to the gash between her
legs. As he looked down, Leroy was overwhelmed. She guided his dick
to the pink gash that divided her brown pubic hair. She had less hair
than him! The heady wetness was dripping from the opening.
Both watched in amazement as the tiny pink gash stretched with
ease to engulf the plumb-sized end of his black cock, then snap closed
around the knob. She was tight but sloshy wet. He pushed gently and
she pulled on his asscheeks, but it went no where. Debby was groaning
and he was afraid that he was really hurting her. Debby whispered "Oh
God... it hurts, it's so fucking thick. Stretch me... make it fit.
Pull it out an inch then push in 2 inches. It'll go... trust me... go
He wasn't familiar with the movement, but he tried it. It felt
awkward, but it worked. Out an inch then in two. Again and again, he
saw his cock pull out a bit shiny wet, and slippery slide back into
her cunt. She was awed at the rigidity of the massive manhood and the
roughness of the thick veins. He couldn't believe the tiny hole in
her little body could expand so easily to accommodate his 2 1/2 inch
thick black trouser meat.
"This is beautiful. I feel so full... so completely stuffed," she
cried. Leroy looked down and said "I don't think so." "What do you
mean" she said, moving to look for herself. Her eyes rolled up and
closed realizing they were still 3 inches apart. "Fuck you... fuck
Not about to let up, she swung her legs to her chest, completely
exposing her inflamed sex volcano to help ease the last few inches in.
Pumping slowly and with instinctively longer strokes, his massive
manhood forcefully inched deeper. With each pounding stroke of his
thick meat, Debby let out a deep moan. "Yes," she wailed. "Do it
just like that. I want to feel your balls smack my asshole!"
It didn't take this long to wack off, he thought. Leroy was sure
he would have cum before now but was glad he didn't. This was great!
He started pumping even harder and faster, keeping pace with Debby's
breathing. Perspiration ran down his ass, over his anus and dripped
off his heavy swaying balls.
When their loins finally met, entwining short hairs, Debby's moans
took on a tone of thrill and surprise. They quickened. Suddenly
Debby's body stiffened and started shaking, her vagina alternately
tightened and relaxed around him as he pumped in and out. Her mouth
was wide open, but nothing was coming out. This lasted a couple of
minutes, before she came out of it. "What's wrong," he asked, worried
she was convulsing. "Did I hurt you?"
"Good gosh no, silly," she smiled breathlessly, "you made me cum,
reeeally hard." Then whispered, "Don't believe it when they say size
doesn't matter. Take it from me. The bigger they are, the longer they
last and the bigger the orgasm. Now, keep pumping while the pump's
primed. Let's do the doggy. Get up."
Puzzled, Leroy begrudgingly eased his yet unsatisfied member out.
The sucking sound of withdrawal and the smack as it slapped against
his chest made them chuckle. Debby rolled over, got on her elbows and
knees, thrusting her petite bottom toward Leroy. He knew now what to
do. Slowly, ever so slowly, his black fuck stalk slid between her lily
white cheeks, over her puckered pink anus, and parted her blossoming
cunt lips. He leaned forward and grasped a long nipple in each fist,
gently twisting and pulling. Debby reached back and, firmly massaging
his balls, yanked him into her forcibly until their loins smacked and
Leroy bounced on her hard and fast again and again. Soon, her
nipples flushed even larger and her velvet cunt tightened. Debby
whimpered each time he slowly eased almost all the way out, leaving
just the tip of the massive 2 1/2 inch knob submerged, then
ferociously lunged down, their loins slapping loudly, filling her
belly with his incredible love log. She rocked hard, matching his
thrusts with her own, showing no sign of letting up. After several
minutes, Debby stopped, convulsed orgasmically for a minute, then
resumed, rocking even harder. She had several orgasms, minutes
apart, each lasting a minute or more.
Both looked like they just stepped out of the shower. Sweat was
beaded up all over their bodies. Leroy was too tired to continue
and pulled out to Debby's surprise. "You can't stop now, I need more
and you haven't cum yet" she squealed. "Lie down on your back and
I'll do you."
Debby squatted over him like a deep knee bend. With one hand on
his chest for support, she reached around her ass and guided Leroy's
throbbing thickness into her yearning quim. Placing both hands on
Leroy's chest, with eyes closed and head back, she slowly slithered
down the 11 inches of his shiny black mastiff. With long squats, she
rocked vigorously, pounding forcibly against his groin as his meat
packed her fully. Debby's heavy milk bloated breasts bounced wildly.
Her ecstasy exploded in a scream as she cummed convulsively. As
Leroy's body slapped up against Debby, his own climax started boiling
deep within his massive testicles. It rose quickly to a plateau
seemingly without end, causing his balls to heave ounce after ounce of
cum into the deepest recesses of Debby's womb. Filled to overflowing,
the cum squirted out of her gored gash as he continued cuming.
As her body wracking orgasms subsided, she arched her back,
grinding her clit against his jumbo joy stick and offering Leroy a
ripe breast. Leroy eagerly sucked her bloated throbbing nipple deep
into his mouth. As the milk shake squirted from her swollen breast,
Debby rolled her eyes and orgasmed for the sixth time.
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