Humiliation Mistress

Humiliation Phonesex is a special kind of fantasy role play which Mistress Alexa uses to handle and train and tease men who need to be humiliated. Humiliation can involve being made to wear panties, to being dressed up like a girl in a public place, to being used like a woman in a sexual way, to being compared physicially to a big man with a huge penis in front of a wife or girlfriend -- small penis humiliation. Mistress Alexa has always loved being a Humiliation Mistress.

Alexa thought Kirk might just be at the breaking point.

And she loved it!

If he took it, great; if he quit, she'd find somebody else.

"Please make him stop, Mistress Alexa!! It hurts so much!" There were tears of humiliation- in the boy's eyes, but she had no intention of ending his humiliation spanking session now.

"Continue," she coldly ordered. Without delay, the large man continued to paddle Kirk's backside. Though Kirk struggled, his punisher was a good foot taller and had a solid muscular frame. He also had the incentive of earning more money in one afternoon than he did in a whole week of outcalls. Even if the action was kinky, he'd gladly play his part for the amount of money the woman had offered him.

Besides, he was enjoying it.

And so, Kirk, dressed in a woman's blouse, skirt and high heels, wriggled helplessly on the man's lap, his bare ass, now bright red with pain, fully exposed by the simple adjustment of flipping up the short skirt. But his face was even redder than his bare ass: he was shamed in front of his boss, he was humiliated by being forced into women's clothes, and he was embarrassed because his tiny penis was getting harder and harder with every paddle of the big muscular man.

Mistress Alexa was revelling in a fantasy she had, until relatively recently, been unaware that she ever wanted to indulge. Stretched out behind her desk, in her large, soundproofed office, she watched the two males in fascination, all the time fondling herself. She was excited by her secretary's humiliation, and the more ashamed he was, the wetter her panties!

Neither of her two slaves - one owned, the other merely rented for the day - were in any position to threaten her. Far from it; it was she who was directing the action.

Ironically enough, she had gotten the idea from a Humiliation Phone Sex session she has done with a houseboy just that morning. She had told the little faggot to take off all his male clothes, go into his wife's closet, and dress himself up as a secretary. Then she teased him mercilessly about his tiny penis. Then she made him pull his wife's panties down around his ankles and spank himself while she laughed on the phone....

He wept, and then he came.

She had loved it...

Particularly when she heard him weeping into the phone and confessing that he had dressed up in his wife's clothes before, and that he wished he could be her sissy bimbo secretary!

Kirk had the psychological profile of a man with a tiny penis, and she knew that he would break with daily lashings of tiny penis humiliation. The spanking was part of the humiliation treatment, part of what would force him to assume his status as her sissy secretary. He had begun dressing in skirts and heels less than a month after she hired him.

Over the last few weeks, she had slowly begun insisting that his wardrobe more faithfully display his secretarial status. Panties were first, then other lingerie she demanded he model for her in the store.

"He's my secretary," she would blithely explain to the shocked female shop clerks as Kirk, red faced, donned some frilly peignoir she asked him to try on. Pretty stockings were next. They were always covered by her male clothing at work, but both she and Kirk were very aware of what lay just underneath. Kirky was taking to his new clothing sullenly, but without any real resistance.

She fantasized about taking it further.

Kirk had finally blown up, threatening to take action.

Alexa had laughed. "You want to sue me over sexual harassment, Kirk? That would be a laugh! Man repeatedly raped by female boss! It would be a joke."

But Kirk hadn't slunk away as she'd expected. "Well, it's true, isn't it, Mistress Alexa? We both know it," he added, pouting like a hurt little boy.

Her stony silence to him for the rest of the day had frightened him more than one of her dressing downs. Inwardly, she was pleased to have the pretext to teach her office boy a lesson - one he'd never forget.

That evening she let him go home - he'd need his rest for the ordeal on the following day, one he couldn't suspect was coming his way. Then, following another day of curt commands, she had made the necessary call.

Summoning him into her office, she explained to him what was going to happen. "Kirk, as you know I've been very displeased with you since your impertinent comment yesterday afternoon. I've given it a lot of thought and it is clear you require an attitude adjustment of major proportions."

Kirk's blue eyes were clouding with fear as she continued.

"Because I'm not sure how you'll handle your next lesson, I've requested some assistance. His name is Arnold. Please come in, Arnold."

A tall, well-muscled man Kirk's age entered the room carrying a bag, which he placed on the table. "Ready when you say, Ma'am."

Kirk's glance darted about from the large man, to the door and than back to Hennessey.

"Good." smiled. "Now Kirk, you indicated that you needed a lesson in sexual harassment. I - with Arnold's assistance - am prepared to give you that lesson. You see, for decades, men have abused women in the workplace - made them dress provocatively, act submissively, put up with exploring hands and have even been blackmailed into performing degrading sexual acts to retain their jobs. This doesn't happen any more because women have put a stop to it.

But you can't begin to appreciate any of this because you're a male. Hence, your ill-considered comments of yesterday. Therefore you must be taught first-hand. Kirk, we're going to try a little role-playing this afternoon. Call it 'sensitivity training'. Take the bag on the table and empty it out."

She and Arnold watched impassively as he did so. He looked up in confusion. "This is all women's clothing, Mistress Alexa."

She shook her head. "Oh, no Kirk. It is sexy secretary's clothing. And this afternoon, you are going to be hunky - and quite gay - Arnold's cute little secretary." She smirked. "You'd better get dressed-your boss is waiting."

Desperately, Kirk turned to the muscled gay hustler, mouth open to plead mercy, but the man just glared. "Do as she says - or else," he warned, pulling out a tazer from behind his back.

A brief attempt at flight was rewarded with a agonizing shock from the tazer across the back. Kirk fell to the floor, gasping for breath.

"Now get dressed," Alexa ordered. "Arnold has some tasks for you to perform."

Choking back tears, Kirk slipped off his clothes and began to dress as a woman.