Young Winston

YOUNG WINSTON

Part 1: House Boy

Cocoa Beach Florida 1966. Eighteen year old Winston Smith has women problems. He is at the mercy of his overbearing foster mother and her dyke girlfriend at home, and at school has to deal with corporal punishment enthusiast, Principal Harden and her sexy, air-headed secretary.

Authors Note

Although not present in every chapter, the story includes: incest (emotional if not actually biological), female domination of males and females, male domination of females, corporal punishment, submission, humiliation, lesbian seduction and sex, all manner of "straight" sex, anal sex, foot and lingerie fetish, group sex...and maybe some other stuff. None of it is extreme or harsh.

I am not sure if this should be considered a "celebrity" story or simply a novella. All of the female characters are very loosely based on characters from movies and TV, some of them no doubt unknown to a younger generation.

Gloria -- Gloria Wondrous "Butterfield 8" (Elizabeth Taylor)

Christina -- Maggie Ryan "PAN AM" (Christina Ricci),

Principal Harden -- Principal Dearden "Detachment" (Marcia Gay Harden)

Miss Daily -- Dollye Daly "Courtship of Eddie's Father" (Stella Stevens)

Margret MacAfee -- Kim McAfee "Bye Bye Birdie" (Ann Margret)

This multiple first person POV story builds slowly, so if you like your sex with little context, you should jump to ahead a few chapters.

All characters are over eighteen years of age.

Chapter One: Gloria's House

Gloria:

"Where's my drink?" I finally had to shout, that damn boy had been gone so long.

"Thomas! You'd better not be studying in there while I'm thirsty out here," I warned him. It was getting so that I couldn't let the little bastard out of my sight for five minutes.

"Getting too big for your britches, eh?" I growled when he finally appeared with my drink properly arranged on its silver tray.

"Not so big I can't still put you over my knee!" I watched him jump as I gave his little bum a swat with the eighteen inch, flexible wooden ruler I kept handy.

"No ma'am," he replied in a firm voice as I'd taught him. He stood up straight waiting for me to taste my drink.

Slowly swirling the ice cubes around with my finger I looked up at him; he

was

getting bigger, he must be five foot eight by now which put him four inches taller than me in stocking feet, about level in my usual heels. He was broad in the shoulders, but he was slender at the waist and hips; not that size is all that important compared to a commanding presence. Still, it was time to remind him of his place.

I sipped the drink, it was reasonably well made. Thursday night was whiskey sour night, although I would probably switch to gin and tonic when Christina got home.

"Crouch down," I snapped; "how many times have I told you not to loom over me."

"Yes ma'am," he replied and crouched down beside my extended calf.

I'd been sitting back on the couch with my bare feet up on my leather ottoman, my tight, black shift riding half way up my thighs. Now I sat up straight so that I was a couple of inches above his thick blonde mop.

"You need a haircut," I said as an excuse to get a handful of his sandy blonde hair and give it a tug.

"Yes ma'am," he replied with only a hint of discomfort in his voice.

He was no sissy; he shouldn't be after all the trouble I'd taken to train and toughen him up these past four years. Hell, he'd been so scrawny and underfed when I picked him up from the orphanage that they had incorrectly listed him as twelve years old when in fact he was fourteen.

That little bureaucratic bit of shit had only recently been cleared up. I would never have fostered a fourteen year old.

Now

I was stuck with an eighteen year old, an adult really. He could leave any time he wanted to, and what a cheat that would be on

me

, the bastards.

I let go and gave him a little slap on the cheek; "What were you doing in there Tommy, reading some damn history book?" I asked.

"No ma'am I was just making sure the snacks are prepared in case Miss Kelly wanted something when she gets in," he replied.

She wasn't always hungry after an international flight, but she was always bitchy, so he was right to be prepared.

"Just make sure you can produce a tall gin and tonic without delay," I said.

I jammed my foot between his legs and rubbed it up and down roughly; he was well endowed, although I'd never let him know it. He was doing his best not to look up my shift at my naked pussy. He

knew

I was naked under there because he' had, as he did every night, reached up my shift, undid my stockings one by one, and then pulled down my panties so that he could take them to the laundry room and rinse them out.

He was rock hard and I allowed him a little purr even as I probed and dug in hard with my toes.

I smiled; eighteen or not, I still owned him. I'd been his foster mother for four years now, during which time he'd had plenty of opportunities to complain to child services, but he'd never made a peep.

His proper name was Winston Thomas Smith. I thought Winston too grand for him and called him Tommy instead, or Thomas if I was really pissed off at him. I'd fed him and clothed him, given him order and stability, and just enough affection to keep him in line. And now he wanted to fuck me. The poor boy would never have a chance against me no matter how big he might grow.

I could take him out in public without embarrassment; there were no marks on him, he was fit, his skin was clear, his teeth were in excellent shape, and he had a head of thick healthy hair. He behaved himself like a dutiful son and I responded as a strict, but loving mother. In public he called me "mother" instead of the more appropriate "ma'am".

"Were you playing with yourself in there? Sitting rubbing your cock underneath the table while you read some story about slave traders. Those shorts are so easy to get into, you can just reach up the leg eh?"

I pushed my foot up the wide pant leg and hooked him below the balls. He'd been looking me straight in the eye like I'd taught him. I was delighted by the way his eyes fluttered as he let out an involuntary sigh.

"Only when my work is done ma'am, or if I'm waiting for something to cook," he replied.

He stated his facts, he didn't plead or simper. I smiled at him and rubbed more gently. I had to admit I was proud, proud of my handiwork at least. I didn't love him, but I was not ashamed to claim ownership of him either.

"Well you have work to do right here where I can keep an eye on you, so get to it," I gave a final push and then settled back in the couch.

"Yes ma'am," he said and stood up straight, not trying to hide the big boner sticking straight up his shorts, and went over to his place beside the couch where the newspapers were spread to resume his nightly chore of caring for the footwear of the ladies of the house.

Television was horrid on Thursday nights, even worse than usual, so I'd put Sinatra "Live at the Sands," on the Hi Fi and dimmed the lights.

Winston sat down cross-legged and picked up one of my favorite pairs; five inch gold colored heels on a black woven leather body with gold soles, closed toes, and a wicked arch. He tended to it lovingly, polishing and treating the leather with care. He was diligent, but I had to keep an eye on him to make sure that he didn't just work on his favorites.

He'd started to work on a pair of Christina's black, five inchers with a wide ankle strap and a bow over the open toe, nice shoes; the boy had good taste, but I had made him work on mine instead.

The sight of his strong back and arms working away bothered me. As he grew physically stronger and his lust became more demanding I was going to have to stay on top of him, watching for any signs that he was questioning my authority. Standing up, I let my full breasts sway as I wriggled my shift back down into place. He was watching me of course, as soon as I stood up he'd looked up to see if there was something I wanted.

"Let me see that one," I said holding out my hand for the gold heeled Louis Vuitton.

He stood up in one fluid motion with the left shoe in his hand, and offered it to me confidently from a respectable distance. He'd done a good job. I looked it over, the leather was treated so it was soft and supple, and the gold was spotless and polished to a glittering sheen.

I looked up at him, my head tilted slightly back and slightly to the side, and then passed the shoe in front of my nose and inhaled deeply.

"Do you think it smells right, Tommy?" I asked him handing it back.

He sniffed it like I had, "Yes, the leather smells good," he said looking at me quizzically.

"No, really smell it," I said stepping closer to him.

I put a hand on his shoulder, pressed my boobs up against his arm, and shoved the shoe right up against his nose.

"Smell the inside. Come on, get your nose right in there; how does it smell?"

I grabbed the back of his head and pushed his nose right down into the toe. "Well, how does it smell?"

"It smells good, ma'am," he replied in a muffled voice.

"What does it smell like?"

"Like good leather ma'am."

I let go of his hair, reached down and grabbed his hard little ass, digging in my nails; "What else?" I demanded. He hesitated and I dug in harder.

"Your feet, ma'am," he said.

"Ahhh, my feet. So you think my feet smell good?"

"Yes ma'am," he replied without hesitation.

I let go of him, stood back and looked at him sternly; "Do you like to smell my shoes?"

"Not particularly ma'am, just when I'm working on them, they smell nice with the leather and all," he replied.

"Did I give you permission to smell my shoes?" I demanded.

"No ma'am," he replied.

I put my hands on my hips and nodded angrily; "Such liberties! You really do need to be put in your place, Thomas. Put down that shoe, get down on your knees."

He did as he was told and I hiked my shift back up and sat on the edge of the couch with one leg crossed over at the knee.

"I am going to show you that you are not too old to have over my knee, but first let's explore this foot thing of yours. Come here, lick the bottom of my foot!" I ordered.

He crawled the few feet over to where I sat, and still on all fours, stretched out his tongue and ran it along the bottom of my bare foot giving me a quite unexpected shiver of delight; funny, no one had ever done that to me before.

"And the top," I said to cover my unease.

This was no better, in fact it felt very nice as he ran his tongue along the top of my foot to my ankle; he put a hand on my knee to steady himself.

I gave my foot a vicious little flick to push him off, then grinding my thighs together roughly against the restless feeling in my pussy, I crossed my legs putting the other foot over. I did it more slowly than I'd intended, giving him a longer look up my shift than I'd planned. Without prompting he licked the bottom of my other foot and then swirled around to the top.

I could feel my nipples pop and press hard against the lacy bodice of my shift, so I bent forward and clouted him hard on the ear.

"Get up!" I growled.

He stood up straight, hands at his sides, looking down at me, his mussed hair hanging partly down into his eyes making them hard to read. His face was impassive, but I sensed a bit of a smile. His big cock was standing straight up again, up past the waistband of his shorts.

"What are you waiting for, you know the drill, get those shorts down. I want to see your bare bum you insolent little boy," I snapped.

His eyes never left my face as he pulled his shorts and underwear down and let them drop to the floor. I regarded his exposed manhood with disdain although he possessed a good seven inches of clean well shaped cock with a fine head. Pretty impressive for a growing boy; I approved, but could never let him know that.

I gave it a hard, dismissive slap and snorted; "You think you're going to scare me with

that

little thing? Do you think that makes you the boss around here, Tommy boy?"

"No ma'am," he replied.

He should have been squirming, but he wasn't, I was the one who couldn't keep her ass still.

I slapped my knee, "You know the position," I said.

He lay across my lap at an angle so that his upper body rested on the couch, his legs stuck straight out behind him and his hot, throbbing, cock pressed against the satin of my shift high on my left thigh. I gave him one as hard as I could with the palm of my hand.

"Don't you

dare

come on me, do your hear?" I smacked him again.

"Yes, ma'am," he replied, and finally there was a tremble in his voice.

I gave him a good going over, as hard as I could, until my hand was sore from slapping his rock-hard butt. Every few strokes I would trail my fingers around the curves of his ass - to tease him, I told myself.

His cock was like a marble pillar pressing against my leg, and as I spanked him he started to slide it forward towards my crotch. He was shaking now, not from the beating, but from the effort to keep from exploding all over me. He was breathing hard, almost whimpering, and I knew I had my victory.

I took the ruler and gave him a medium tap; "Don't you dare!" I warned him, "or you'll get the wood for an hour."

I went back to using my hand, but only for a few more slaps, I didn't want him enjoying it too much. I grabbed him by the hair again and pulled.

"Up!" I commanded.

He stood up, his face was red, and the hint of the smile was gone. He was practically vibrating with the effort to contain himself as his youthful seed leaked out the head of his straining cock and dribbled down it's shaft. I ignored it; he'd kept it off of me and that was what counted.

His ass was red and just a little purple in a couple of spots, nothing that wouldn't disappear in a few hours. Very rarely had I lost my temper enough to leave a mark on him that lasted more than a day. I had no desire to injure him or mar his pristine beauty.

At any rate the pain was of secondary importance; it was the submission that mattered.

"Are we clear on who runs this house?" I demanded.

"Yes ma'am." He replied. His butt must have been smarting, but he didn't try to rub it.

"That little prick of yours is of no significance to me. You can play with it all you like, so long as you wash your hands afterwards, and not when you should be working. Do you understand?"

"Yes ma'am."

"Now go clean yourself up, and no jerking off! Put on some clean underwear and then hustle your little ass back out here with a fresh drink. March!"

"Yes ma'am," he replied pulling up his pants.

I sighed and lay back on the couch as he hurried out of the room. Raising a child could be

such

a trial.

Straightening my shift I took the opportunity to rub my wanton pussy, that insistent beast that was always trying to get me into trouble. I needed a good fucking, but all the men I knew were nasty, greedy little creatures, either arrogant or clingy, and none of them had a clue how to please a woman. I needed relief, but I would have to get it from myself as usual.

Sinatra was crooning "It's a quarter to two," which it was not. I looked up at the clock; almost nine, and still no Christina.

Winston was back quickly, his promptness demonstrating that he had no inclination towards defiance. My drink was well made and properly served. Frank finished his last tune.

"Play it again from the beginning," I said.

With a deft and careful touch, he flipped the LP, set the needle, and then returned to his place. Without a word he began working on a pair of Christina's blue suede, knee length boots.

Quite appropriately, Sinatra was just wrapping up 'Come fly with me' when I saw headlights play on our curtain as a car pulled into the driveway.