Prissy's Sissies
A New Drawing by Prissy with storyette by Prim

Highheels for Boys

  "Get in here with me. I'm going to make sure your legs are as feminine as Carmel's... and stop sniffeling!"
  "Mother-In-Law, please don't take me into the store."
  Carmel, Johnny's wife, had exceptionally shapely legs, which he did not want replicated on himself. But his life was becoming so miserable with Janice in charge of him, anything was possible.
 "All the women will l-l-laugh at me."
  "Hah! Will they now? How terribly, terribly different from any other place I take you, you effeminate little sissy." She tightened her hold on his wrist as if screwing a vice, and pulled the lightweight young husband behind her.
  Janice Hardsheet led the way through the brightly lit pink entrance. Whimpers of dismay wheedled in his throat as his anxious gaze fell on rows and rows of women's shoes, all of them with extremely high heels and all gleaming in every colour of the rainbow. The pungent fragrance of shoe leather clogged his nostrils and had an aching effect on his penis as it tightened into the doubled satin gusset of his silk panties. Assistants in little black dresses and women with their own sissies watched his approach with grins of dark lipstick, looking him up and down and giving his mother-in-law grins of sisterly approval.
  "There's room here," said a tall, young looking woman who moved her beaver fur coat from the seat beside her. "My, you've got him looking pathetic for his trip to the sales. He must be your son-in-law?"
  "That's right, my daughter Carmel's husband. She's handed him over to me to 'bring him up'. Janice Hardsheet", and she held out her gloved hand. "I've brought him here today to make sure he has truly effeminate shoes to add to his girlie shame. And is this your son-in-law in the gorgeous little pink frock?"
  "Yes it is. My daughter Catherine has given him as a present for me to play with. His name is Arnold, but we're going to re-christen him with a pretty name in a few days' time, so he needs some attractive shoes for the big occasion. I'm Vanessa Murdiston."
  The women were admiring each others' handywork when Miss Prudence came up, the proprietress of High Heels for Boys.
  "Ladies, welcome. You have brought us a delightful pair of pinkies this morning. I do like to see sissies in pretty white collars. So girlish. How can I help?" Her bust was so ample it should have made her tip forward on her towering heels, but she was an elegant picture of poise and fashion with her blond perm and figure-fitting black dress with silver jewellery.
  The two women told her why they wanted the new footwear, and asked to have their sons-in-law fitted with some of the boutique's most high-heeled shoes.
  "Of course. What I would recommend first, though, is that we put the sissies into our new girls' nylon stockings. They're called 'Seamy Slims' and come in a shorter length and are softer and silkier. They have a most feminising effect."
  Vanessa clapped her hands. "Yes please. Can you dress him in them for me?"
  Miss Prudence was more than happy to oblige; dressing sissy boys was her greatest pleasure. Each husband had to take it in turns to stand and have his panties taken down and his stockings removed, along with his garter belt since Seamy Slims required longer, prettier suspenders. Next each husband was fastened into a startlingly girlish garter belt in sparkling satin, with ruched satin suspenders that dangled on his thighs. Then they were clipped into their short, very tight girls' stockings and their pink panties were restored over their shamefully excited erections.
  "The motto of High Heels for Boys," explained the proprietress, "is 'Shape their legs and you shape the contents of their panties'. I think you will find those clitties showing extreme girlishness as we try your sissies in some very highheels."
  Johnny and Arnold were mortified. Not only were they being sissified in front of a shop full of women, but their mothers-in-law were planning to feminize them even more in their legs and penises.
  With the store being so packed with sissies and their mistresses on account of the sales, Miss Prudence gave her personal attention to Janice and Vanessa. She brought half a dozen boxes for each of the sissies, and they were soon standing upright, getting used to shoes with heels that were higher than they had ever worn before.
  "Hah, you're going to have a very feminine stiffnes in your panties, aren't you?" announced Janice loudly as Johnny stepped carefully across a space on the floor. Women nearby watched him with smiles on their faces, looking at his shoes, then up at the crimson face of the sissy in the pink silk dress. "I want to see nicely pointed panties," cried out Janice for everyone to hear, "so walk nicely in your lovely pink high heels, and really believe you're a sweet little girl."
  Vanessa, in the meantime, supervised her son-in-law having his feet fastened into a pair of white patent heels with ankle straps. The pretty white bows fastened across the ankle with a snap fastener, and he was ordered to his feet for a display of 'feminine walkies'.
 "You couldn't wait to feel your feet inside those shiny white high heels, could you?" she cried. "So off you go then, Miss Highhels... let's see you sashay and simper like I've taught you."
  Arnold set out from his mother-in-law's side, holding onto his petticoat frills and even his stocking tops to keep his balance.
  "Hands out in the sissy-wimp position," ordered Vanessa. "We want to see your lovely legs."
  "Oh yes, Vanessa," observed Janice, "his legs look so sweet in his shortie nylons, and those white heels look so feminine on him. You must take them."
  Minutes later, with both the boys in pink heels, their mothers-in-law wanted to see the effect of their Seamy Slims while the two husbands were walking hand in hand in their heels.
  "Hold out your petticoats with your other hand, Arnold," he was told. "Place your heels across each other, Johnny," ordered Janice. "That's better mincing, now show us your best girly smiles and do some nice girly sissy giggling."
  The whole boutique was watching as the de-sexed young men descended into tears as they walked across the shop floor and back again, swaying their pantied bottoms and swishing their petticoats so that the satin of their gussets roused their emotions uncontrollably towards a climax. There was nowhere to hide, nothing they could say that would save them. They squeezed hands as each looked at the others panties and almost together the dark stain on their panty points grew wider and wetter. Bobbing from side to side as they minced in front of everyone they gave themselves up to spurting pleasure and shame. To their mother-in-laws' great satisfaction, the sissy cream appeared in white dribbles, dropping from their panties onto their nylons and high heels amid rapturous applause from every woman in the heels department.
  Half an hour later, after more mincing displays from their sissies Janice and Vanessa bought a lovely selection of shoes, as well as a generous quantity of Seamy Slim girls' nylons.
  "I'll have him in a pair right now," said Janice, choosing one of Johnny's new pairs of shoes for him to wear at once. "He's got a busy shopping schedule ahead: Pantie-Petticoats, Girly Boy and that new place,Ribbons'n'Bows, and I want his legs to be shaped very prettily in each of them while we try on some very frilly lingerie and short flouncey dresses."
  Johnny's head drooped in misery. His next stop was bound to be a lingerie place, so that his wet panties could be replaced, then resoaked as a result of his humiliations and replaced again.
  And his heels? They were so lovely, they were making him stiff again. And he knew what would happen when mother-in-law got him home. She would insert the heel of one of her own spiky heels into his mouth for him to suck on, and then line the toe of his lovely new shoes with a pair of her silkiest panties, and then ease it over his stiff peeny so that he could push it deep inside and make sissy love to pretty highheels. Johnny could hardly wait.