"I'm Ms Draper. How can I help?" she says with a scornful grin on her thick, rubied lips. Her blouse is a mass of ruffles bursting over her bust between the sides of a black leather waistcoat to match her pencil skirt to the knees. It bulges round all her curves as if it's acting as a corset.
"Hello Ms Draper. Cassandra Sharpe. I'd like you to help us satisfy the sissy-boy infatuations of my stepson here. His name is Dale, Dale Pinkerton, and as you can see from the pointed front of his blouse, he loves being dressed in my things."
The shop-owner purses her lips in contempt as she looks as the bottom of Cassandra's blouse, because it's her blouse she has dressed me in to bring me on this miserable trip. Her fingers trace the rounded prong that is sticking upward beneath the peaches and cream silk of my blouse, then she lifts one of my hands to examine the tubular blouse cuff with its three silk buttons, looking into my eyes between times through those horrendous, blue-tinted glasses.
"I've caught him in my clothes four times in as many weeks," Cassandra reveals, and I shrink with even more shame as Ms Draper draws herself erect and leers down at me with her eyebrows pulled together, "and each time he was wearing either my dress with a large collar or this blouse I've got him wearing now. He evidently has a thing about my clothes which have a big collar: I found him with it turned up round his face, and he was VERY excited."
he shopkeeper's fingers zero in on my collar: it's so deep round the back of my neck, up onto my hair, and its wings are long and pointed, mostly cream but with peachy shapes here and there. It makes Cassandra so heavenly when she wears it. I can't tell her that of course. I find my collar being lifted up the back of my hair and over my cheeks - so silky and cool.
"What you say, about him obviously liking big collars on your clothes, doesn't surprise me at all. They're all the same these sissy-bois. They have their little fads and fancies which they just have to satisfy, even if it means they run the risk of getting caught. It may be that he actually wanted to be caught. He may even have hoped that you would dress him in it yourself, which you have, so you are playing his game, Ms Sharpe." She spoke to Cassandra over my shoulder with my face enclosed inside its silk envelope. "But the rewarding thing for you and me is that they need to be pampered and indulged with their faves, because that binds them to the fetish clothing and feminine behaviours that make them more effeminate and sissy. You did the right thing to bring him to me."
She produces a pair of full cut panties in pale blue nylon and slips them over my head, then threads the collar through one of the legs so that the panties hold the blouse collar up all round my face. I can't free my arms to try and stop her. She separates the collar at my eyes so that I can see them both while they're talking.
"Let me see now," she says, taking me off my stepmother and leading me along the rails of silks and frills, "blouses with big collars. Let's look along here." We reach a rail of terribly girly blouses, all in richest satin and silk, with Cassandra right behind me, probably gloating at how this woman had me closed up in her blouse collar with a pair of women's panties.
"Ahh," says Ms Draper, "what about this one, my little sissy? Nice isn't it? Pink satin with a wide sissy collar to cover your shoulders and lace edging all round it. You'll be so girly wearing it for your stepmother."
A pang of humiliation shoots through me, but at the same time I know I would love to wear this blouse. Cassandra takes it and holds it against my front, then lifts the collar to show me how large it is. "Hmm," she says, "let's see how high up your hair it would come if I fix it up around your face with a pair of my panties."
"Or what about this pretty girl's blouse?" says Ms Draper.
Oh my God, I nearly slump to the floor in a fit of weakness, which both women realise because they reach out and catch my arms.
"I can see this blouse is very appealing to you, my boy," says Ms Draper. "I think we're going to have to try it on for you."
"The other thing he likes," says Cassandra, "is my panties: my French knickers with lace round the wide legs. He covered them in sissy goo just yesterday."
I squirm with embarrassment as Ms Draper parts the front of my blouse and reveals the pink satin French knickers underneath, pushed out by my furiously thickened cock.
"I presume you punished him for that?"
"Yes, I caned him across the panties, then on his bare bottom." As she says it, I can still feel the smarting tightness across my ass. But I've got other things in the forefront of my mind, because Ms Draper takes the panties off my head and begins to undo my blouse. In no time she strips me in front of Cassandra, then gets everything she will need to dress me for my birthday.
I find I am to be put into stockings. "They will need suspenders," she says. "I suggest in your own style but for today I'll put him in standard white foundation wear."
She dresses me in a white brassiere with satin cups and zips me up in a girdle to match. She attaches my stockings to them, tightly. Then comes the pair of white satin panties she has selected. As she slides them up my stockings I feel my flesh goose-bump and my cock stiffen and swell to meet them. It isn't missed by either woman.
"Look at him. For God's sake, you're a disgrace, Dale Pinkerton: determined to embarrass me in front of Ms Draper."
The proprietress shapes my erection in her fingers through the satin, making me moan with emotion. "Typical of sissies," she says to me, glaring at me through her glasses: "unable to control your prick: likely to soil your panties because of your perverted desire to wear them: probably the prettier the better. Isn't that right?"
I can only confess. "Y-Yes, ma'am."
"I suppose you want panties with feminine frills?"
"With a smooth silky gusset designed to be kind and gentle to women's sensitive genitals?"
Cassandra interrupts. "My dress that he's so fond of is a rose printed dress."
Ms Draper nods. "Then we'll put him into the rose printed blouse." She slips its crisply puffed sleeves up my arms and gathers the sides round me over my bra, the collar sliding round my face in its pink and white prettiness. "Unlike your blouse, Ms Sharpe," she says as she fastens the small, white plastic blouse buttons over my bra, "this is a sissy blouse. It's designed to envelope the buffoon's face inside its feminine wings, so it buttons together up the front of his face, like this!"
Ohhh, I can't believe it. My pleasure soars. It makes me want to ejaculate, but also to wee with the humiliation. My cock aches with both needs as they are both almost irresistible.
I am still bursting for a wee as we leave the store a few minutes later, with me wearing this pretty, rose printed silk blouse so that I have to look upwards to see out of it. I feel so ridiculous in it, showing a pair of panties under it but no pants, not even a skirt, as if every woman on the planet will be looking at me and laughing, while there is nothing I can do to avoid them. I walk in little clickety-click steps in a pair of high heels, until a voice I know reaches my ears and fills me with dread. "My goodness, if it isn't Dale Pinkerton, looking very angelic in his pretty collar!"
To my horror it's Miss Prowse, one of my teachers from Farways High. She has always been my dream teacher, my goddess, but I would much rather the ground opened and swallowed me away from here.
"Dale, my dear boy, you must introduce me to your companion."
"Ohhh, Miss Prowse, er - th-th-this is my s-s-stepmother. C-Cassandra, Miss Prowse was my teacher in tenth grade." I can just make out that they shake hands.
"This costume is because he keeps trying on my clothes," explains my stepmother. "He likes blouses with very large collars and silky pairs of panties, so this is his 18th birthday present: I'll be starting a sissy collection for him."
"Well, well, Master Pinkerton. Congratulations on your18th. You must be very pleased to be wearing such a pretty blouse and silk panties." I feel her hands smoothing against the sides of my blouse collar, pressing the floral silk against my cheeks. She fondles it round and round so that the silk hisses and sizzles round my hair. Then she slips her fingers underneath so that she can shape my face in its silk, with the collar riding higher and fluttering around and above me. I hold onto my panties for dear life to stop my urine from exploding, and my cum. I can't tell which feeling is stronger - which one will win out first.
"I can see you are loving my attention to your blouse, darling," she says, smiling to Cassandra, "but I won't stroke you panties, if you don't mind."
"No," says Cassandra, "but I'll be doing that: it seems the thing for dominant parents is to make sure he learns to love his new sissy clothes and wants to wear them all day and every day."
"Oh yes, Dale," says Miss Prowse, "then you'll become a very girly sissy." Her hands and her words become too much for me to control myself. The pressure in my cock is unbearable and I simply have to let go of a little control, then a bit more as I feel warm wetness on my legs, until I have to surrender to it - and I wet myself in torrents and squirt a splurge of cum at the same time.
They stand next to each other, their hands on their hips as they watch me trying in vain to hold everything back with my hands as wee and cum splutter from my legs onto the pavement. "Never mind," says Cassandra, and Miss Prowse agrees with her. "It will all make sure you are ensnared in sissy dressing, just like I want you to be."
"I'll tell you what," adds Miss Prowse. "I have a couple of dresses with oversize collars, very pretty, and as for pretty full-cut panties, I can bring them over for you to see if they help to ensnare your sissy stepson."
I burst out crying - but I know that wearing a dress and panties belonging to Miss Prowse will make me want to remain a deeply dressed sissy for ever and ever. I almost want her to come over this evening, and try out their experiment in blouses, dresses and panties that I will definitely love to wear.
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