Being a short man in a tall man’s world had been one long, 27-year string of disappointments for poor Michael. From being bullied at school to being passed over for promotion after promotion at his modest job in the accounting firm, it seemed the only attention Mike ever got was the kind he didn’t want. The worst of it all, though, was being all the ladies’ “best friend” but never their lover. No, Mike’s only contact with females throughout the adult portion of his life was when they were sobbing on his shoulder the morning after a much taller, more handsome man would treat them wrong the night before. Well, that and his occasional thrill on Pervert’s Row at the local strip club, tucking dollars into the girls’ G-strings or, even better, the ankle straps on their spike heels. Sometimes they even let him put the bill in his teeth and let them take it with their voluptuous breasts, then give him a face full of said breasts. It seemed to be his destiny, to be that lonely, slightly awkward loser with the decent apartment and decent job, wasting most of his nights trying to get noticed on Fetbook, and the rest emptying his wallet at the strip bar, going home with sticky messes in his boxers after those oh-so-beautiful women let him touch them.

Well, that was his life before he met Sally. That’s when absolutely everything changed. When she popped in with a private message on his Fetbook page, Mike’s entire world turned upside down. This wealthy, tall, dark-haired, athletically built vixen swooped into his life and systematically fulfilled every little fantasy he’d ever had in the whirlwind that was their first few months as a couple, and he willingly let her push him beyond his outer limits into fantasies he never even knew he had. In short, she was perfect.

Of course, there was a reason Sally was perfect. Unbeknownst to hapless little mikey, as she called him, Sally had been watching him for a long time. Owner of said strip club, she knew all her regulars, and little mikey was an object of interest from the first day he awkwardly sat at the bar and watched those girls from a distance. The longing in his eyes was as obvious as the nose on his face. When she found his profile on Fetbook, it was almost hysterical to her how predictable he was; lonely pathetic little wimp looking for a Mistress to abuse and humiliate him, to let him worship her feet, to make him into a pet for her amusement. They were everywhere on that site, and the few that worked up the nerve to approach her got flat rejected with a referral to a professional Domme she knew. Because most of them just wanted one night of wild beatings and humiliation and then go back to their stupid little lives until they felt that itch again. Little mikey was different, though. Watching him in the club all that time, she knew he was different. He would follow her to the ends of the earth just for the chance to lick her heel.

And in reality, all his little shortcomings fit perfectly into her desires. His “problem” with premature ejaculation was perfect. He never begged to put his little winky inside her, and in return she taught him well how to service her with his mouth, his fingers, the many toys in her collection. And he absolutely loved it when she shamed him over the messes he made; his full-body shudders as he groveled for forgiveness for being so pathetic were like candy for both her sweet tooth and his own. But even after she convinced him to give up his job and his apartment to move in with her and be her house slave, there were places Sally wanted to take him that he wasn’t going to go without a little help. Fantasies she had that she was determined to make him fulfill. But that was just a matter of timing. Patience. And Sally had plenty of that.

They’d been living together four months, and Sally had “little mikey” trained into a nice little routine. He abandoned his job at the accounting firm happily as part and parcel of moving in with her. They slept in until noon, and he’d get up, fix her breakfast in bed (he was quite a good little cook, to her surprise), and sit dutifully at her feet while she ate, massaging her ankles and calves. She’d get up to shower and do her makeup, and he’d stand at the ready in the master suite, holding her towel while she teased him with seductive poses and noises behind the steamed-up sliding glass door, turning his head when she was finished. (He wasn’t allowed to look at her naked body unless she explicitly gave him permission; his backside had taken many welts for that transgression.) Once she was dressed and ready for work, she’d give him a list of rooms to clean top to bottom while she was gone, with the promise of her strap on his backside if they failed to pass inspection. And they rarely passed inspection. She was pretty sure that was deliberate on his part, though. There was always something obvious, something a complete idiot would have noticed, left untouched while the rest was immaculate. So, when she arrived home from work, there would be the inspection, then his beating, and then he would, sans clothes, serve her supper at the table while he whimpered and groveled and kissed and massaged her tired feet in between fetching her wine. And later, depending on what mood struck her, she would take him down to the dungeon and abuse him until he cried out the little safe word she gave him (No more, Mommy!) and make him clean up his little messes on the floor under her St. Andrew’s Cross. Or she’d lie on the bed and make him please her long into the wee hours of the morning, until he collapsed from exhaustion. On her off days, she’d dress the both of them up in properly coordinated leather and take him to the BDSM club to parade him around on all fours, beat him, and humiliate him in a more public forum. She knew he loved that more than anything else; she had to put a cock ring on him to keep him from ruining his leather shorts, a fact she made sure everyone there knew.

And she pushed him farther and farther toward what she wanted out of him; he went under the laser to get rid of his pathetic little beard because she didn’t like being tickled by hair when he went down on her. He agreed to undergo bi-weekly Brazilians when the alternative was sleeping in a cage at the bottom of the bed “like the hairy little animal you are”. And he hadn’t cut his hair since he moved in. By September, he was as androgynous as could be, a just over five foot tall little boy-girl, his wispy blond locks in a little cascade on his shoulders. He was ready, and it was time for her to make a little magic happen. After all, what better time for a little magic than Halloween, for a witch of Miss Cassandra “Sally” Divone Nenet’s caliber?
~~2“Can you believe it? We’re gonna have our first Halloween together!” Sally asked coyly, as she cuddled Mike’s shivering form, stroking his naked back as she brought him out of his sub-space. Aftercare was paramount when taking care of a pain slave, and Sally was every bit the expert caretaker as she was the sadist when it was time to discipline him.

“Mmmm,” Mike replied absently, just barely becoming aware of her words again, the adrenaline subsiding, replaced by her tender touch.

“We have invitations to an absolutely enormous party, you know,” she continued. “So many of our friends will be there!”

Mike flinched a bit when she said that; that phrase was all but code for “Mike’s going to get flogged in front of a crowd.” Terrifying, yet incredibly stimulating. He hadn’t realized how much of a turn-on humiliation was until Sally introduced him to it. “Fun,” he managed weakly.

“You know what would be extra fun?” Sally cooed. “How would you like the chance to switch for the night?”

That got his attention. “Wait… what do you mean?” he said, popping his head up from her bosom.

“I’m sure you’d just love to pick out my costume for me, and be in charge the whole night, in front of all those people, wouldn’t you? No safe words, no nothing, just little mikey playing Big Man Michael, and Miss Sally being just little sally?”

His eyes widened as she spelled it out, and visions danced in his head. He knew exactly what he’d want to see her in; he’d fantasized about it since the first time he laid eyes on her. No leather that night, no, not at all. He gathered his thoughts… she wanted an answer, no doubt. “How… I mean… what… do I have to do?”

“Well,” she chuckled. “First you have to prove that you’re capable of being a Master. How about going a whole week without any discipline?”

“But that’s not fair!” he protested. “All you have to do is make up a reason!”

Her face darkened noticeably. “When have I ever disciplined you and you didn’t deserve it?”

“I… uh… never…” he replied weakly. Truth be told, the rules were all laid out. All he had to do was follow them. Except he wanted her strap on his backside. NEEDED it. He felt unwanted, unloved when Sally didn’t discipline him.

“So what makes you think I would be so unjust as to do it just to win a bet?”

“I… you wouldn’t, Miss Sally.”

“Of course I wouldn’t. Now apologize for making such a slanderous accusation!”

Mike slunk, trembling, down off her lap and onto his knees in front of her. “Forgive me, Miss Sally. I’m a horrible, ungrateful boy, undeserving of your love and care and affection. Forgive your unworthy slave of his transgressions.” It was a well-rehearsed line, and the words came easily.

“You are unworthy, ungrateful, and pathetic. But I will forgive you once again, little mikey, even though you deserve nothing less than to be cast from my sight!”

“Please, Miss Sally!” he begged. “Punish me however you see fit, but don’t send me away!”

Now would usually be a time he would be disciplined, but he’d just spent two hours on the rack; he was in no shape to take another thrashing. “No no, little mikey,” she said, grasping his head and pulling him gently. “Come back to Miss Sally’s bosom. All is forgiven.”

He climbed back up and buried his face in her chest as she stroked him. “So does little mikey want to try to be Master for a night?” she whispered.

“I… I would like that,” he whimpered back, his breathing starting to even back out.

“Then we’ll start tomorrow,” she purred.

“What… happens if I don’t make it?” he asked, almost as an afterthought.

“Well of course, if I win the bet, I get to pick your outfit, you get to be the slave, no safe words, no limits. It’s only fair, don’t you think?”

“Of course,” he replied sheepishly.

Sally had every intention of keeping her little promise, to only discipline him when he actually earned it. But she knew just as well as Mike did how needy he was, how desperate he was for her attention and affection. She wouldn’t need to break that promise. To Mike’s credit, he definitely went the extra mile that day. But the harder Mike tried to please, the less interest she showed. She barely acknowledged the elaborate breakfast of Belgian waffles with fresh-squeezed orange juice alongside her coffee. She caught a bite to eat at work, and coldly announced she wasn’t hungry for the admittedly gorgeous-looking Quiche Lorraine he prepared for her. Her inspection of the rooms on his list was quick and silent; not even offering the slightest compliment for the touches he added, like fresh flowers in her office, and she didn’t even bother inspecting the on-suite, which wasn’t even on that list, but that he’d meticulously scrubbed top to bottom. And to top it all off, she retreated to the bedroom and shooed him away, declaring she was tired and wished to be left alone.

Mike was devastated. What had he done so wrong that she would shut him out like this. He choked back tears as he stared blankly at the laptop screen, at the special Halloween costume he’d picked out for her that day as he waited for her to come home. She didn’t even want him to pleasure her, or even massage her back while she slept! And he dare not ask, no, that in and of itself was an infraction of the rules! Mike’s purpose was to pleasure Sally; it was for Sally to decide what Mike needed and deserved. He had to try harder, do more, because clearly his mistress was displeased with him.

And try he did. The next day he was tireless, cleaning the entire house top to bottom, fixing Eggs Benedict for her breakfast and a thick, juicy ribeye steak with creamed spinach and roasted fingerlings for supper. But she showed no interest whatsoever. She spent the evening in her office, and when she came to bed, she banished him to the dreaded cage.

The next day, it was more of the same. He worked relentlessly all day, cleaning, cooking, doing laundry, and once again she devastated him by coming home late, ignoring the elaborate dinner, isolating herself from him. Few words, no physical contact at all. Mike was bewildered as he lay in the cage again, trying his best to keep his tears silent. At this point, Halloween was an afterthought, the promise of being Master for the night pie in the sky. He wasn’t even sure if she still cared for him at this moment, and that terror trumped all other thoughts, desires, needs. Trembling, weeping, and panic-stricken, he accidentally bumped the cage door as he shifted his weight.

“Be quiet down there!” she shouted. “How dare you wake me?!” Of course, she wasn’t sleeping, she was just silently relishing the mental anguish she was inflicting on him. Physical punishment wasn’t the only path for the sadist. And for sure, he was near his breaking point already.

“I… I’m sorry Miss Sally,” he whimpered, trying to stifle an outbreak of sniffles.

No answer. Mike couldn’t take it anymore. “Please, Miss Sally, what did I do wrong?! Why can’t I sleep in your bed?!”

“Come out of that cage!” she snapped, flipping the light on. He knew what was coming now, but it didn’t matter. He needed it. Damn the costume party, he needed it. He crawled out and knelt on the floor beside her. “What is the rule about Mistress’ instructions?” she asked, more calmly, but still very stern.

“Miss Sally knows what is best for us. We are never to question her judgment,” he nearly whispered, his head down.

“What do you suppose Miss Sally should do about this, little mikey?”

“I need… to be disciplined, Miss Sally.”

“Yes, yes you do,” she said, feigning a solemn tone. “Get Miss Sally her strap.”

He cringed a bit, but at the same time his heart warmed at having her undivided attention again, something he’d been starved of these last few days. He went to her closet and retrieved the pink-handled, heavy leather implement from among her various implements of discipline, laid it on the bed at her feet, and got back down on his knees. “Up here,” she scolded. “Assume the position.” Quickly he stripped naked and laid down on the bed next to her, face down. As he braced for the coming physical pain, he found himself very suddenly erect.

Of course, Sally anticipated that outcome. “Where is your towel, little mikey?” she demanded.

“I… I’m sorry Miss Sally,” he fumbled, scrambling off the bed, embarrassed as his erection stood out in front of him like a flagpole as he walked by her toward the on-suite. He returned with a dirty towel he retrieved from her laundry basket and was most dismayed when he saw what was in Sally’s hand.

She smiled as she held up the little ring. “Stand right here, little boy,” she commanded. He complied, and she grasped the tip of his penis and squeezed. It wasn’t painful, but it was definitely humiliating for Mike as he watched it quickly sag and shrink back to its normal, pathetic self. She lifted it up and cinched the cock ring snugly just above its base. “This is not fun time, this is discipline time,” she said calmly, taking on a motherly tone. “Little mikey doesn’t deserve fun time right now, does he?”

“No Miss Sally,” he mumbled. That little ring, he hated and loved it so, stealing away his manhood, his sexuality, but at the same time exciting him with the humiliation of her taking total control of every aspect of him.

“Now, assume the position.”

He spread the towel out on the bed, lay across it, and braced himself, this time decidedly less comfortable with the blood flow futilely straining against the cock ring, the base of his penis swelling painfully while the rest remained flaccid. There would be an orgasm in his near future, but it would be a painful one, like when she milked him, not at all pleasurable like when he was strapped to the St. Andrew’s cross.

A loud crack and searing pain across his bottom snapped him out of the thought, and he whimpered in spite of himself. Then came another, and another. The blows continued as he gritted his teeth and struggled against the inevitable tears.