Choosing His Penis Dress    by Prim
Ellen Stoker was thrilled. She was at her friend Simone's house, helping her to humiliate her detested son-in-law, and she got to fasten him into this shameful sissy dress. His begging and tears were giving her a glow of pleasure at the tops of her thighs. "He looks like a proper little girl with these sweet buttons fastening up to under his collar petticoats," she said. "I declare, Simone, it's no wonder the fool is so dejected."
Simone Wright sat in front of her son-in-law, Ethan Grainger, in her narrow cocktail dress of apple green taffeta with its 60s style picture collar, curling her lips with triumph and delighting in the childish impression he gave standing on one foot while his other shaddled in its Mary Jane shoe with a pink ribbon bow on the toe. With the frills of six petticoats under his collar and six more petticoats under his dress, plus the ruffles of his frilly panties, he was as feminized as she could have made him. His tearful face attempted to beg for pity again from the middle of its white satin collar.
"B-B-But Momsy-In-Law, please pleeeeeeease don't take me to the women's m-m-meeting in this dress, sob-sob-whimper - it's s-s-so FRILLY!"
She snorted a laugh of contempt, while Ellen laughed too at the side of his face as she fluffed out the sides of his petticoats over his babyish panties. "We couldn't care less what you want," laughed his mother-in-law, "it's what WE want that will happen. Now for the important part, Ellen. We've got to choose which penis dress to put his dick into," and they laughed again as their captive burst out crying with even more despair.
The rack of cache-sexes soon hung in front of him in Simone's fingers as she pondered the pros and cons of this or that confection. "What do you think, Ellen? This one fastens tightly in primrose yellow silk - it's very sweet. Or the dress in hot pink chiffon will give his dick a doll-like appearance. The girls will like fluffing it in their fingers as they inspect him."
Ellen could scarcely stop giggling. "Well what do you think, sissykins?" she asked. "When the ladies come to examine your sexless cock, which dress will make it feel weak and girly in their hands?"
"Oh no! Please!" he mewled, "don't put my dickie into a sissy girly dress. Pleeeeeease!"
His visitor felt more satisfying pangs of pleasure in her wet crotch as this helplessly effeminate male squirmed and begged pathetically in front of them. They selected the peach pink sleeve in silk-chiffon with the acetate silk lining. Simone fastened it at the neck and the root of his shaft with scarlet satin ribbons. His wailing proved to them how deeply he was ashamed to have to wear it. They covered it for the time being in his panties and got the sissy ready for his afternoon out.
The Dorchester Superior Women's Association were waiting for him in their meeting hall, regaled in their spring afternoon finery, resplendent with high coiffures and overpowering perfume. The weeping son-in-law was brought onto the platform, cowering in his petticoated dress collar and pressing his knees together in mortified effeminacy. No wonder the hall dissolved into gales of laughter from more than thirty women of all ages. After they had laughed and laughed to their hearts content at the sissy in his ridiculously girlish dress, they settled down to watch him being humiliated.
"It's nice to see one of our sissies in a deeply frilled pair of panties," declared Simone, talking about what a pleasure it was to keep him in girlish little dresses, "but what I really want you to see today is how his sexless little dick has been dressed for your pleasure, ladies."
There were "Ooohs" of expectation on all sides, until Ellen stood him at the front of the platform, holding his arms out of the way behind him, and his Mother-In-Law caught the waist of his panties and drew them down to his knees. "Behold, Ladies," she announced, "his dick fastened up in his Pollyanna penis-dress."
The reception was deafening. Every female was on her feet, craning to see the upright member in its deliciously delicate encasement. How feminized! How pretty!
"But what if he needs to climax?" enquired Lavinia Railsworth. "Yes," called Iris Samuels: "can his penis dress hold it?"
There was a burst of laughter, shared by Ellen and Simone, but before they could reply, her son-in-law obliged by giving a demonstration, by losing the last ounces of control and surrendering to his shame and impotence by pumping gush after gush of white sissy cream into the delicate garment until it was saturated and dribbled shamefully down his legs and into the air in front of him. It was clear to see how pleasurable it was for the pervert to have his sex smothered inside a doll's dress, in front of a roomful of baying, tormenting, superior women.
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