Prissy's Sissies
Drawing by Prissy and storyette by Prim

Dress Code for the New Sissy Maid


  The doorbell was answered by Miss Agatha Sourness, housekeeper to Mrs De Vane. She held the door back for Fiona Fairface to lead her son inside, then closed it and turned her attention to the boy. She undid the large buttons on his deep collared burgundy jacket and slipped it off his shoulders to take a look at him.
  "I've packed three blouses and three pairs of my slacks for him to wear," said the boy's stepmother, "and just a couple of little dresses I had made for him. I hope that will be enough."
  Brandon Fairface was wearing one of her white blouses and her salmon pink slacks bordered with pink satin, with satin buttons down each hip pocket. It made a nice sissy outfit for an eighteen-year-old boy to wear outside, but Miss Sourness did not think it nearly feminine enough for a sissy maid. She turned him round by the blouse to view his slender waist and pert,girlish bottom.
  "Leave his case with me," she said sharply. "It won't be much use to him: there is a strict dress code for sissy maids at Gracefell Gardens."
  Her expert fingers assessed the boy's bottom curves and felt the rows of satin buttons that ran down each of his hip pockets. "Those half heels will have to go. Madame insists on very high heels for her sissy maids, worn with the sheerest, seamed nylons."
  The housekeeper steered the boy's stepmother to the door, with the assurance that she would be informed of the boy's suitability or not after one month of service. Then she turned her attention to the sad-looking, abandoned soul.
  "Mrs De Vane expects rigorous observance of all rules for her staff," she began, standing him in the middle of her bare looking office to undo his pants and slide them down his legs, "and so do I. You will be dressed as the sissy you are at all times, and your demeanour is to be completely effeminate. I hope I make myself clear."
  Brandon managed a single bleat as his blouse disappeared down his arms, which she took to mean: "Yes, ma'am." The shy, timid youth had never been able to speak up to women. It was a miracle that he hadn't fallen to his knees in front of the housekeeper, who wore her greying hair off her gaunt face and tied in a bun. Her cold authority over males had been honed during her years as warden in the Straightwaist Institute for Penile Reform. Instead he stood, head bowed and submissive, as he was rendered nude in front of her.
  "Your sissy maid duties will include caring for Madames' lingerie, day and night. You will present her with her brassieres, her panties and her slips as she needs them. These are exquisite garments of the finest silks and satins and you will learn how to give them the loving attention, I may say reverence they deserve."
  Brandon's heart fluttered in his smooth, bare breast as Miss Sourness spread a pink satinex corset round his waist, fitted the zip fastener together above his bottom cheeks and zipped him up tight and firm. The long, delicate garters dangled onto his thighs as she prepared his nylons.
  "You will need daily lessons, in front of my desk, in the correct procedure for fitting Madame into her corselets... and in removing them when required." Brandon's heart fluttered again as he was told to lay his hand on Miss Sourness's blouse to steady himself as she fed his stocking over his foot and smoothed it up his knee and smooth, slender thigh, then pulled three ruffled satin garters to press them tautly into each stocking top.
  "But even more importantly, you will learn how to draw Mrs De Vane's panties up her stockings and fit them, inch perfectly, in place around her feminine domain."
  Ohhh, it was so embarrassing, the way his penis was extending itself so firmly as he learnt about his sissy maid duties. At times the purple head was barely an inch from the housekeeper's cheek.
  "You must learn how to kiss Madame's panties when they are in place, to show your adoration of her and her panties, and to express your devotion to her with your sissy lips." She completed putting Brandon into his stockings. "These duties are so important, you will practise their details on me, until I feel you are as devoted as you must be to a real ladies' panties."
  The trembling sissy maid had to rest his hand on the back of her blouse again as she fitted him with his uniform high heeled shoes. In shiny pink patent, these were a mere four inches but would be 5 and 6 inch heels in succeeding weeks. The white nylon of her blouse was so attractive to him, he almost cried out with his desire to be dressed in it.
  "You will complete Madame's dressing in all particulars, fastening her dresses, or her skirts and blouses for her." A white petticoat, rustling with lace-edged flounces, dropped over his head and nestled round his nakedness. Those intoxicating girlish feelings he always felt when he was being petticoated, came rushing through his soft young body and forced his penis to its full extention.
 "Again," went on the housekeeper, fastening his petticoat at the back, "you will practise your duties by dressing and undressing me in my boudoir... with extreme adoration and girlish grace." She turned and reached down a dress hanger from the end of the closet, presenting him with his pink satin maid's dress. Brandon failed to arrest the whimpers of emotion that gurgled from his throat.
  The dress dropped over his head and cascaded onto his petticoat in sizzles of glossy prettiness. Miss Sourness spread its skirt over his petticoat frills and fussed his girlish sleeves evenly into puffs of satin. She fastened his dress buttons up the front of his bodice between dainty trims of lace, and tied his neck ribbons into a bow at his throat. A little wail escaped him at the cool silkiness of his ruffled collar, echoed as it should be on the cuffs at his elbows.
  "And finally," continued the housekeeper, taking a deep breath to calm herself at the stiffened length of his penis, "you will attend to any personal needs Madame might have. She may need her legs soothing, for example, or her large breasts easing out of her brassiere cups for a breath of cool air. Or her panties may need checking for comfort."
  She fitted the sissy maid's cap into his hair, pressing her black satin skirt against that nice erection and feeling its hardness against her. Then she stood back to assess his presentability.
  "You will practise these attentions on me to improve your technique. Now, come with me into the panty-fitting room."
  In the servants' panty-fitting room, the delicate maid saw rows of extremely pretty panties hanging to dry. Four chests of panties stood against the four walls, marked Satin, Ruffled, Silk and Lacy, with panties laid on each of them. He was brought to the dressing table, which was little more than knee high, with lingerie spread across it, three or four panties deep. Behind it, he beheld himself in a huge dressing table mirror, and his stiffness disappearing into the white silk of his frothy petticoat.
  "Stand back while I spread this mat. I am about to put you into your maiding panties." She unrolled a sheet of shiny pink rubber and told him to stand in the middle of it, in front of the dressing table. She undid the cuffs of her blouse on her upper arms, put on a pair of black satin opera gloves, and refastened her blouse over them. Then she took her governess pantying apron, in ice pink rubberized taffeta, and fastened it into a ribbon bow at the back. Then, from the dressing table, she selected a pair of pink panties in slippery silk and crouching in slithers of her apron, presented them to Brandon's high heels.
  The panties were drawn upwards, the waist elastic pulled out to accomodate his erection and then gently let go to smother it. The boy stiffened his whole body, straining not to lose control, which did not escape her notice.
"I am warning you not to squirt boy cream in your sissy maid panties. If you do, you will be caned in the presence of Mrs De Vane, followed by corner time in three pairs of maids' panties."
  Moments of agony followed as the boy fought to resist his aching sissy urges. He was led back into the kitchen, where Miss Sourness laid the mistress's lingerie for the morning over his arm and presented him with the tray holding her breakfast.
  The housekeeper led the way to open and close doors, and finally reached the door of Mrs De Vane's chamber. As he entered the room, surrounded by lavish drapes of chiffon and lace, and saw his Mistress in her gleaming white corset, he came to a stop, shuddered in his dress, and ejaculated into his panties, pressing his legs together with whimpers of feminine surrender.
  Madame watched until the last dribbles of cream had run down his stockings. A faint smile eppeared on the lips of the housekeeper standing at the door.
"Miss Sourness," said Mrs De Vane, crossing one nylon leg over the other, "kindly bring your cane for the new sissy maid, and three pair of girls' panties. Very pretty ones."