How Shall We Humiliate Him?
by Prim

Rupert heard the posh voice of Veronica Sade and the hyena laughter of her friend Phoebe Pantswell flooding into Sandra's bedroom from her sitting room. They were in high spirits, as always on Monday and Friday mornings. And no wonder. They were going to spend the hours before lunch enjoying end-to-end orgasms, which Rupert would provide them with as part of his de-sexing training. They were disgusting in the way they forced him into their juiciest places, as did the Fortescue sisters on Tuesdays and Thursdays, while on Wednesdays it was the turn of the ladies of the local council. Sandra opened the door and thrust him through in sizzles of satin and silk crepe.
"Ohhh, here he is, the little pouffie!"
"Oh my god, Sandra, you've got him really feminized in your frilled blouse and silk pleats. I hope his clitoris is tied round in your sani-pads."
Rupert Whitling's cock was already stiff in his mother-in-law's satin panties, but the sight of her friends on the settee added a further inch to his erect organ. Veronica was in a cream silk dress with a frill over her breasts, its skirt absolutely swollen with layers of silk petticoats. She wore it with a red Chanel jacket, while her immaculate hair was held in a red straw panama. She was putting her kid gloves on again, the better to masturbate his defenceless manhood.
But it was the shameless lust of Phoebe Pantswell that stiffened him even further. Ohhh, how he wanted her breasts to smother his cheeks to right and left in the blue silk of her erotic sundress. But what he feared most, or longed for, was the power and the width of her pantyhosed thighs. With or without her panty silk in his face, he would surrender his sex to the depths of her juicing labia. He was sure he could smell her wet vagina already as he was forced to his knees in front of them by his mother-in-law.
"Good morning Miss Veronica. G-G-Good morning Miss Phoebe," he whimpered, bowing his hair-do to each of them in turn and holding his pleats out sideways as if in a curtsey.
"Is our little nephew-in-law feeling deeply ashamed, for us seeing him in his Mommy's blouse and skirt?" pouted Veronica, her lipstick curled with contempt.
"God, what a sexless blouseboy!" snarled Phoebe, her legs parted for her fingers to enjoy their first gusset rubs of the morning. "I can't wait to feel that tongue of yours, panty-boy. I'm going to cover it in a stream of juice, I can tell you."
"Thank you for coming to visit Mummy-In-Law," mumbled the 24-year-old, feeling faint at the prospect of hours of humiliation. He had his wrists secured by Sandra, sitting behind him, her legs astride his nylons. "P-Please allow me the p-p-privilege of spending sissy time un-n-nder your skirts, ladies."
Veronica arranged herself well back on the settee and lifted her skirt and its petticoats up to reveal her silk stockinged knees, then the lace of her pink full cut panties. "You will start by kissing every inch of my panties, little sissy boy," she said. "And if you satisfy me, I might allow your tongue inside them."
"And if he doesn't satisfy," he heard, with a dig in the back of his ribs, "he can go over your skirt for the mother and father of a good hiding, before he tries again."
Rupert's head was pushed from behind and pulled from in front, then held in place as his lips worked feverishly to shape and press kiss after kiss after kiss over the panels of satin and lace as the good lady carried on her conversation with her friends, occasionally opening her legs wider to admit him deeper into her sanctum. The time came for her panties to be removed, which her admirer did with the greatest of care and respect, before being dragged and pushed into the heart of Miss Sade's petticoats, between her suspenders, to find the source of all those juices, hot and steaming. He buried his tongue into the soft, wet flesh for the start of his morning tonguing exercise.
The women were quite used to growling their climaxes without interruption to what they were talking about, which happened three times before Phoebe insisted it was her turn to be satisfied.
"I'll have him laid flat, Sandra, on his service table, if you don't mind," she said, on her feet faster than her 180 pounds should have allowed.
"Come here, my little panty-pouffe, and get yourself down there for us to fasten you in true helplessness suitable for such a cunt-sucker in silky pleats." Her bee-stung lips grinned from ear to ear as she secured his feet together at the foot of his service table, while the others fastened his wrists out of the way to give her free access to the bloused and skirted son-in-law.
I can't wait any longer, Phoebe darling," declared Sandra, standing over him as she faced his feet, and hoisting her skirt and petticoat. "You can have him after I've enjoyed sitting my clitty on him for a quickie, then he's yours for an hour darling."
Phoebe snorted her chagrin and planted herself back on the settee as Rupert looked up into the circle of descending skirts, until his mother-in-law's white directoires lowered their silk gusset onto his helpless face. They were already moist as they settled and went to work, sliding, lifting and dropping, winding, gripping and squeezing. By the time they rose again ten minutes later, her son-in-law's cheeks were running wet. His eyes had only a moment to adjust to the light before the shadow of Phoebe Panstwell glowered over him, her bare flesh edged all round with the wide but short pleats of her mini-skirted dress. She had thrown off her panties, leaving her wet thighs clad only in the panty of her hose.

Rupert Whitling whimpered with despair before she landed, but as her large, wet labia touched his nose and spread themselves over his face, settling all her weight, he felt the kid gloved hands of Veronica Sade grasping pleats, petticoat and panties round his penis and pulling him into sizzles of feminine imprisonment.
His moans became hums beneath the mounds of female flesh, heard only as he gasped for each breath he was allowed, as the women resumed their conversation, which revolved around how they were going to drag the sissy along to the mall that afternoon, and take him for a bit of lingerie shopping in Dulcet Modes, where they would meet some of the women of the Housewives Institute and maybe arrange for him to amuse some of them during an afternoon of pleasure.