Sandy Jo

We were all initially thrilled when our folks told us Sandy would be watching us Friday night.  She was smoking hot, long red hair, slender legs and hips, and tits that popped off of her chest like full water balloons.   No one in our group was her age so she seemed like a major adult to us.  She always wore low-cut jean shorts and a t-shirt with no bra.  She’d cover her puppies with a sweater if the pastor or the wives were near but otherwise she let them roam, to the delight of every nearby male.  Rumor was she had gone all the way more than once, and had given numerous blowjobs at the local make-out spot near the river. 

Our parents were all going to a party and had pitched in to hire a babysitter.  We were just excited to be in the same house with such a sexy, mature young woman.  We knew she’d gone to real, grown-up parties with alcohol and more, and it was exciting to us.

Sandy’s mom was a slight, cringing woman with long blonde hair down to the middle of her back, who rarely spoke when her husband was around, a terrifying large bearded man who was usually out hunting or fishing.  We didn’t know it then but the petite blonde received regular, sound thrashings from her husband’s thick belt, howling into her pillow to avoid embarrassing herself to the neighbors.  To us she was always just “Mrs. Carmody,” and none of us ever dared talk to Sandy’s scowling, cigar-smoking dad.  I have no doubt Sandy herself also received a good belting on a regular basis, as did her sisters.  Later I learned she also got the brush from her mom, but usually only when her dad was too drunk or tired to do for her himself. I guess she got tired of only being on the receiving end of the deal.

Sandy Jo was all smiles and sugar till our parents pulled away, then her smile turned mean and she lined us up facing the wall in the family room, telling us in a rough voice to stay like that.  She took a scrunchy and tied her long hair back out of the way, then informed us our parents said we needed an “attitude adjustment” and to our surprise began spanking us!  It was just a few smacks each with her hand but they were hard, and we were afraid.   I felt her squeeze my cheeks roughly as she smacked them, and she grinned at me mockingly, her red hair bouncing behind her.   She stood looking at us for a minute, and we hoped that was it.   But then she grabbed Toby, the youngest at 12, by the ear and pulled him into the studio, which was a small, mostly sound-proofed room that our dad used for making training videos at work.  The door closed behind them with an ominous click.

For a few minutes there was silence except for some scraping noises. After a little while we could hear, just barely, some whacking sounds and Toby crying out and pleading.  It went on for some time, the noises stopping for a bit then starting up again, each time louder than before.  We guessed she was spanking him harder and harder, and as the sounds changed we winced at what sounded like the percussion of implements on bare skin.  Each series seemed to get longer and longer, and his reactions louder.  What was she doing to him?  Not knowing what was happening made it worse.  Finally after about 20 minutes of this the spanking ended in a climax of fast impacts and we could hear Toby howling.  A minute late she came out looking quite smug and exhilarated, and Toby followed, red-faced and weeping, still buckling his pants. 

“No rubbing that bottom!” she told him merrily, and gave his butt a hard slap, which made him cry a little harder.  We all flinched and pressed ourselves against the wall as she looked us over, smiling.

Pursing her lush lips, she ordered him against the wall and took a terrified Bill, who was a year or so older, by the arm and led him back into the room.

Of course we asked Toby what it was like, whispering desperately, but he wouldn’t answer, just faced the wall and cried, not even daring to rub his butt though he clearly wanted to.  We got more and more scared about our own turns.

I was next.  Sandy came out and considered us contemptuously, tapping a slender foot. I glanced up and saw her flushed cheeks, and she crooked her finger at me with a grin. She didn’t even bother physically restraining me, she just smiled and beckoned, knowing I was totally cowed by her beauty and ferocity.

Obediently I followed, pulse racing as a tearful Bill took his place next to Toby.  

She had pulled the studio’s large stuffed leather easy chair in the middle of the room.  Her excitement obvious, she bounced across the room, hard nipples poking at her t-shirt, eyes flashing.  She plopped down and gestured for me to get over her lap.  I didn’t dare disobey.  She spent a few minutes adjusting my position so her target was elevated, my hands and feet supporting me on the white linoleum floor tiles. 

She licked her lips and rubbed her hands all over my butt, clearly savoring the moment.  “Well, Davy, time to teach you your lesson.”  She gave my ass a good slap, watching my face, then another, then settled into a steady fusillade that echoed around the studio. Slap! Slap! Slap! Slap!

I remember the first part wasn’t too bad, she used her hand and it was more humiliating than painful.  Being spanked like a little boy was bad enough, but it was even more embarrassing after several minutes when she paused, reached underneath my waist, unsnapped my trousers, and began to pull them down to my knees!   Naturally I protested but to no avail.   “Naughty boys get their pants taken down!” she told me, narrowing her eyes at me.  “Complaining will only get you extra!”  She laughed as she tugged, exposing my threadbare tighty-whities while I fervently wished I was anywhere else.  And her sarcastic commentary a bit later when my underwear was yanked down to join my pants had me blushing to my roots and questioning my manhood. 

But the fact I was now wriggling my naked midsection against Sandy Jo’s soft bare thighs almost made up for the increasing sting in my boyish buttocks as well as the humiliation.  I’d probably have been erect if I wasn’t so scared.

She slapped my exposed bottom as hard as she could for another few minutes, laughing haughtily from her position of dominance and crowing over the color she’d added to my cheeks.  Then she sighed reluctantly, gave me a squeeze, and said “Red enough, for now, I suppose!” and lectured me for a minute about how I should obey her, running her hands over my red butt and squeezing it hard.   Despite hearing the earlier two boys get it, I was really hoping that was it and she would let me go.  Maybe she liked me better than the others?

Then she grabbed a cheek hard, with her other arm turned my head to look her in the eye, and told me it was nearly time for my real spanking to start.  I was quaking with fear as she chuckled and told me to stand up, releasing my buttock and slapping it hard. 

She looked me in the eye really mean then, and told me to strip completely naked.  Hoping to stay on her good side I nodded and meekly obeyed, reluctantly slipping everything to the floor in a pile with shaking hands.  Then I had to grab my ankles while she inspected her handiwork, after which she made some adjustments to the chair while I waited in my humiliating position. 

When I turned around I could hardly believe what I was seeing.  Sandy Jo sat in the chair beckoning.  I’d known the arms of the chair had padded metal bars underneath, which allowed them to be lifted a couple feet, but she’d found a new purpose for them and I didn’t like it at all.  She gestured imperiously and I quailed, shaking my head and getting ready to run away.  Sandy Jo rolled her eyes, leaned forward and grasped me firmly by the balls and penis, and pulled me over her knee.

Whimpering, I positioned my nude self as she dictated.  As the arms were released to ratchet down I was firmly pinned over her lap at the knees and armpits, with my naked ass in the air.  I gasped as she released my crotch and rubbed her hands in glee, seeing how well her plan had worked.

It was like a bad dream.  I could not move forward, because of the bars above my shoulders.  I could not move back, because of the bars spreading my legs.  And the padding restricted how much I could move my arms and legs.  I broke into a cold sweat as I realized my naked ass was now totally at Sandy Jo’s mercy.

She smiled and took a plastic hairbrush from her purse, humming and taking her time.  She had to lean really far and I could feel her tits press against me, hard nipples poking into my back. Under other circumstances it would have been quite erotic feeling them drag across my back as she searched her purse, but I was terrified.  The implement emerged, blue and pink with flowers.  I still have nightmares about it. SMACK!

She giggled.  SMACK!

“Owwww!” Our introduction was not kind.  SMACK!

“Aww, did you feel that, little boy?”  Sandy sounded quite pleased with herself.  SMACK!

“OWWW! Yes Miss Sandy!” SMACK!

She laughed.  “I bet you did!” SMACK!  “And on the bare, too!” SMACK!

SMACK!  It really hurt! I tried to put my hands in the way to interfere, but I couldn’t reach that far given how I was pinned.  SMACK!  Sandy saw my futile efforts and tsked, waving her finger.  SMACK!

Sandy Jo was diabolical in her application of the hairbrush.  She started slow, asking me sweetly to describe how each one felt, drinking in my pained reactions and halting responses.  Then she started giving me multiple swats.  SMACK! SMACK! I begged her to take it easy, which only made her giggle more.  SMACK! SMACK!

The series of swats grew longer and my pleas more urgent, each ending with a satisfied wriggle of her hips and a lecture about how I deserved this, that it was good for me, and besides it was fun!  For her anyway, for me not so much.

During each series of smacks I forgot about her soft thighs, but with each wriggle after she reminded me.  She was impossibly sexy, hair tossing behind her, and in between throbs I would forget I was being spanked as she leaned over, mashing her tits into my back so she could see my face as she lectured and questioned me.  Her rose scent filled my nostrils and underneath it, when she shifted, I caught whiffs of feminine musk, betraying her excitement.  SMACK! SMACK! SMACK!I knew it was wrong for her to use us this way but I couldn’t help being a little proud that punishing me was making this beautiful creature a little horny, even though it really hurt.  SMACK! SMACK! SMACK! SMACK!

Finally, eyes sparkling, she told me to “take your medicine like a good boy” and she began giving me long series of swats on the same throbbing cheek, until I was sobbing and howling, promising to be good.  Stiff medicine indeed! Now we both wriggled against each other continuously, her in sensual delight at taming a boy’s bottom, me desperately seeking surcease from her painful assault.

Satisfied with the state of my distress, she wriggled her way out from under me and out of the chair.  She wedged a large pillow beneath my waist to replace herself.  Then, to my surprise, she pumped out some cold cream from a nearby table and began massaging it into my tortured asscheeks.  I winced at her first touch, but was soon sighing in relief as her fingers spread the balm around. 

“Is that better?” she cooed in my ear.  I could smell the mints in her breath.  I nodded and she smiled smugly.  “I bet it is, you little perv.”  I gasped as she squeezed my sore right cheek hard, then resumed her caresses, commenting wryly on how red my butt was.  Occasionally her fingers would brush somewhere sensitive and I would feel the reaction like electricity under my skin.  Despite the circumstances, I probably would have gotten hard if she’d gone on much longer.

Her voice was soothing as my sobs fell to sniffles.  I tried to wipe my face with my hand but found I could not reach that either.

“Almost done, Davy.  Just… one more thing.”  I felt a flood of relief.  It had been a terrible spanking!  Doubtless everyone outside had heard me crying like a baby.  I wished I didn’t have to go out there where I was sure they would all be staring at my red, flushed face just like they had the other two.

She made an adjustment and I tried to get up, thinking she was letting me out.  But instead the chair clamped me more tightly.  She lowered the back of the easy chair all the way so my bottom was now the highest point.  She gave my now-gleaming bottom a squeeze, then flounced back in front of me, eyes glittering, and my relief fled as I realized her “one more thing” was going to be another painful spanking.

Sandy Jo looked me in the eye and trickles of dread went down my spine as she slowly, flirtatiously removed her leather belt, waving her delectable, unattainable hips at me as she gradually pulled it free.  I whined as the realization sunk in, loop by loop. 

SWISH! SWISH! I winced as she took some practice swings just above my upturned ass. Suddenly my sore butt felt even more vulnerable after her comforting application of cream.  Her loosened shorts began to slip without the belt, displaying the tops of her red panties.

She raised her long arm and leaned in close, pursing those sexy lips.  I could smell the sweat she’d raised punishing us, and her rose perfume beneath.  She took a deep breath, almost panting, and I realized her rippling tits were fully visible down her shirt from this angle.  She caught me looking and jiggled them a little, and I groaned as my head swam.  The combination of terror and horniness was intoxicating.

“Now I’m going to make you my bitch, Davey-boy.”  I whimpered in fear. 

THWACK!  And she did.  I was already promising to do anything, if she’d just stop.  THWACK! I struggled helplessly.  THWACK! I wasn’t going anywhere. THWACK!  Tears poured down my cheeks.

Then she began the series.  THWACK! THWACK!  I howled and pulled at my restraints.  THWACK! THWACK! THWACK!  The pain was unbelievable.  TWHACK! THWACK!  I made incoherent noises, trying to promise her anything, desperate to submit completely to this fierce sex goddess.

Sandy Jo laughed and really let me have it.  I’d probably still have nightmares about that belt, except that I wake up in a cold sweat the instant I remember it swishing through the air.

*******

The rest of our time together went about how you’d expect.  Sandy Jo loved baiting us into spankings.  We often played Twister and if she caught you looking at her boobs falling out of her shirt, or her pussy peeking out of her cutoffs in a thong, or her perfect ass stuck up in the air, it was butt-beating time.  Or we’d play Monopoly and she’d lean out over the board counting money so you could see her nipples if you dared to look, then sit back with her knees up in those shorts so you could tell from the stubble on her pubic mound when she’d last shaved the kitty. She didn’t even get angry, she just got a certain lazy smile and you knew you’d been caught. 

“You need to learn to respect women!” she’d tell us, dragging us into the studio to be disciplined, and boy did she give us reasons to respect her brush and belt.  The same went for any “accidental” physical contact, or any too-obvious male reaction.  She’d grab the suspect organ through your clothes and squeeze it for proof, then use it to pull you over a couch and spank you hard till it went soft in her hand.  Then she’d pretend to be sad and ask if we didn’t find her sexy anymore, laughing and laughing as we cried.  Her luscious body, always inches away but untouchable, was a source of constant torment nearly on par with the spankings.  We all longed to feel those curves and she knew it, lording her feminine charms over us, daring us to glimpse the forbidden and pay the price.

Other times she didn’t even pretend to have an excuse.  She’d just saunter in with a gleam in her eye, say we needed another attitude adjustment, and line us up along the wall, cowering and begging her to take it easy.  She’d tell us we deserved it, that we were dirty boys, that she knew we were all jacking off to her at night after she left.  And we couldn’t really respond, because it was true.  But of course we didn’t stop, and her lingering scent in the places she sat still got us hard.  Sometimes I’d even think about spanking and humiliating her as I touched myself.

On the other hand, sometimes after spankings she’d spend 10-20 minutes alone in the studio.  We’d hear some humming and a little moaning but none of dared comment on it.  She never gave a reason for her absences but now I’m pretty sure she was masturbating with a vibrator, slaking her illicit excitement over spanking us.

She never stripped us in front of each other, always taking her victim behind a closed door, rubbing her hands in anticipation as she disappeared from view.  Probably afraid it might turn us gay, seeing each other’s red throbbing bottoms.  At the time that was taken pretty seriously.

In retrospect it’s pretty clear that Sandy Jo mainly took the babysitting job in order to spank us, and getting paid $50 to do it was just icing.  Naturally our parents thought it was great how well-behaved we were after her visits.  And I’m sure she was letting the dads all have a good look at her assets when she picked up or dropped off the boys.  Keeping them straight was important too, and if they thought about her later that night with their wives, it was the latter who benefited.

Even worse was when she’d bring her skinny friend Heidi, who was quite thrilled with Sandy Jo’s hold over us.  She was a constantly-grinning, gum-chewing bottle blonde who loved seeing us get it and made no attempt to hide it.  She wasn’t a huge looker like Sandy Jo, but she had a lean sexy body, and a mean, thin-lipped smile.  She would cheer her friend on as she spanked us, and when we began to cry she’d kneel in front of our faces and rub her eyes mockingly.  “Boo hoo! Does it hurt?” would come her high, sing-song voice as the brush or belt drove more tears from our eyes, and she’d giggle.  She never spanked us herself but was always eager to take us in back and help strip us naked, fondling and teasing as our faces bloomed scarlet.  She was bolder than Sandy in that regard, spreading our cheeks and poking everywhere with her long white lacquered nails, telling us how disgusting we were, and how much we deserved it.  She was always urging Sandy to make us kiss the implement and thank it for teaching us a lesson.  Once she brought a ping-pong paddle and watched in fascinated delight as Sandy “tested it out” on each of us until we howled.

The girls both loved finding new ways to shame us, especially if we were in our own homes and not just visiting.  A few of us kept journals and diaries in our rooms, and if they were found under a mattress or tucked away in a closet during “cleaning inspection,” they’d merrily read aloud our most personal thoughts in mocking high-pitched voices, giggling and slapping each other on the back, even falling down if they were especially overcome by the hilarity of an entry.  Our faces burned as we knelt, hands behind our heads, in “cleaning inspection posture” as they called it, often having already absorbed multiple punishment for real or imagined shortcomings in our cleaning duties, bun-beatings delivered to us by hand over our clothes as we rectified our chores.  However, if anything was read they considered “naughty” (a broad category) we’d then have to lie down on our beds, a pillow under our waists, and expose our bare bottoms for their editorial opinions, which invariably left us in tears from their ridicule as much as from Sandy Jo’s hand (if it was naughty) and brush (if it was also about girls) and belt on top (if it was also about her or Heidi).  When our sobs were under control again, Heidi would then make us record the spankings in our journals, forcing us to write how we deserved it and that we were thankful to be punished by our beautiful and amazing and totally fair babysitters, who were reluctantly but admirably dedicated to maintaining our discipline.  They promised to check that we hadn’t removed the entries or written anything negative about them.

And if Sandy and Heidi were bored, everyone, visiting or not, would be pulled into a bathroom one by one for a “hygiene check” which we knew was really just an excuse to strip us naked and humiliate us.  But we were terrified of them so of course we went along.  The older girls would make us stand in the tub, swabbing our privates with wet wipes to “check” us. Heidi especially seemed to enjoy this part, grinding her wipe into us until we groaned.  Naturally if you failed the brush was applied to correct you as the girls nonchalantly discussed what a dirty boy you were, and how you clearly weren’t being spanked enough, your tears barely adding to the flow into the drain.   Next we’d be handed a bar of soap and have to lather everywhere, and I do mean everywhere.  They made us spread our (usually red) cheeks to show them the suds between. They’d blast cold water from the massage head setting into our balls and penis, which stung, but even worse was when they directed the freezing stream against your anus.  But at the end they’d turn the heat up, putting it on normal shower, and it was delightful.  The warm water felt glorious running down our shivering backs, and in soft tones barely hiding their amusement the girls would reassure us it was all over now, then their soft hands would begin toweling you off everywhere, their sexy bodies inches away.  At this point sometimes Sandy Jo’s perfect bra-less tits would be clearly visible through her wet shirt, round and alluring with the nipples poking out, so keeping your eyes away was a terrible struggle. But it was a trap, because if you showed the slightest sign of male reaction above or below, Sandy would smile and start loosening her belt, eager to teach your naked wet body a lesson in proper respect, Heidi trying to suppress her giggles at your waning manhood. 

Now and then on weekend afternoons our parents had a picnic and Sandy took us “camping,” which really just meant she set up a tent in a local park, in an isolated area away from people, where she could take off our clothes and spank us in private.  At first we were excited, especially when she’d pack her sleeping bag.  We all dreamed about sharing it with her. 

Sometimes she gave a reason but mostly she just told us all to go and gather the willow vines she’d use on us, trickles of dread shooting through us as anticipated their imminent application.  Then we had to lean over the logs and present our butts while she decided whose was first.  We had clothes on at that point but was it was still embarrassing as she walked back and forth, squeezing and comparing.  Finally she’d slap one and tell them to head to the tent... and bring his willow vines.  Sitting around the unlit “campfire” of vines which was only going to burn our bottoms, we’d hear each the sounds of each other getting it, then the tent would unzip and a grinning Heidi or Sandy would emerge with their crying victim, often still dressing, and then tell you it was your turn now.  Then you’d be stripped of your clothes and she’d look you over contemptuously.  Her sleeping bag (which she only brought for this purpose) would be packed into a roll and she’d made you bend over it.  She’d smack your butt till it was bright red, then her lips would curve and she’d pick up your willow vines.  If Heidi was there you’d have to kiss them and thank Mother Nature for her assistance in disciplining you as she tried to suppress her grin. 

Sandy Jo would  tell you if you moved, she’d tie you to the roll and start over, and as several of us found out, she meant it.  She’d start slow and soft and build up your whipping.  THWICK! THWICK! THWICK! After a couple minutes you’d be gripping the roll and sweating, yelping as the willow bit you again, hard and harder, until you were crying and begging Sandy Jo’s smug face for mercy on your poor butt as Heidi giggled.  If you lost control and reached back they tied your wrist to your ankles and started all over as you sobbed.  A few of the older boys probably made it through without being tied but some of us never did. After your turn, you’d be kneeling instead of sitting, listening to someone else get it and being glad your turn was done as you rubbed your throbbing behind.

Some Friday nights Sandy had dates with some local hunk or other, but sooner or later the prospect of tanning boy butts was too much to resist.   Our parents would give us the dreaded “we’re going out, be on your best behavior or else, the babysitter has our full authority” routine, and then she would appear, grinning and using that brush in her long red hair, and our stomachs would fall into our shoes.  If we were especially unlucky, a blonde head with bobbing jaw would appear behind her.  Sandy always liked showing off for Heidi, so we knew we’d really get it, and in front of a smirking, giggling audience!  Years later, the sound of smacking gum still gives me a moment of terror.

Sometimes she’d bring the other boys, other times the parents arrived with them and everyone chatted before they headed out.  In either case we would immediately rush to pay fealty, with our “Hello Miss Sandy” and averted eyes amidst fervent promises to be really good, cleaning our hands and faces and neatening our rooms in a futile effort to appease her lust for our bare bottoms.  If our parents knew how we were being treated, they certainly didn’t mind the results. 

But one day we turned the tables.