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A sissy is shown how to really dress, by his aunt and his dominant lady boss.
Chapter One: The Office Boy
“I really think your nephew William has terrific possibilities, Irene. Are you sure you would loan me Tanya, until Billie Boy’s transformation is complete?” asked Penelope Chambers, of her good friend, Irene Lane. They were seated in Irene’s living room, discussing William Lane, while Irene’s sissy maid Tanya, minced and sashayed, gaily about, serving tea and cleaning up.
“Oh yes! Definitely! William has never met my little Miss Petite here. With him moving back in, meeting Tanya may make him suspicious. After all, he’s worn his share of petticoats, which is the reason he moved out, in the first place,” Irene stated, quite frankly.
“When I have my secretary call, I’ll make sure she tells him that Beth Danvers, the headmistress at Elite, gave us his name,” Penelope stated with a smile.
“Correct! He must never suspect we know each other,” Irene added.
Irene, in her mid-forties, was a writer for a magazine called Ms. CEO, a ladies business publication. Penelope, stunning and brilliant at 32, was a senior editor for Ultra-Chic, a fashion publication. William was Irene’s errant nephew.
Irene had raised him utilizing petticoat discipline. In addition he had been sent to both beauty school and to Elite Secretarial Academy. Though he held a hair stylist license, and a two-year degree from Elite, in secretarial studies, he refused to work at either job. He had rebelled and moved out. Now, however, he was at his wits end. Going to college and delivering pizza’s, unable to make ends meet and saddled with college loans he couldn’t pay on.
He wasn’t even close to a four-year degree. At least a good year of school was needed to complete that. He had begged Irene to let him move back in so he could work full time and pay off the loans. She had allowed it only if he would pay room and board. He agreed and moved in.
Prior to that, Irene’s sissy maid, Tanya Petite, had moved to Penelope Chamber’s home. Tanya, a graduate of Ms. Stephanie’s Institute of Domestic Training, was an exquisitely trained sissy servant. She had graduated from Ms. Stephanie’s New York campus. As Stephanie Strong now had ten such facilities, Penelope wondered which one, if any, she should send William to. The Virginia facility was the closest. She had been told the Atlanta campus was the best.
She decided to cross that bridge when she came to it. Calling her current private secretary into her office she had her place the call to the unsuspecting William Lane. Priscilla, Penelope’s current secretary would be leaving the magazine soon. William would be her replacement, and a very suitable one.
After getting off the phone with Priscilla, William got out a calculator and began doing some math. “Goodness!” he thought. With the salary and perks he’d have the loans paid off and be out from underneath his aunt’s dominance in about a year! Then he could finish college, going part time. He’d take the job, even if it was a secretary’s position.
He sat in Penelope Chamber’s office mesmerized by her beauty and charm. He was only slightly put off by her remark that she intended to utilize his beautician skills as well as his secretarial talents.
“You won’t mind that, will you William? On occasion being called upon to do my hair, nails and make up? Of course I’ll also expect you to prepare my coffee and tea and also serve it,” she added smiling prettily, and holding up the serving tray.
“No Ms. Chambers, not at all, I’ll be more then happy to perform those duties,” he added, trying to sound excited.
“Excellent! Now there’s just one more thing. I had a very hard time convincing the board of directors to permit me to hire a male secretary. You see, William, we are on a expenditure cut back program. Even a senior editor like myself has to cooperate. Travel expenses especially. Follow me so far?” she asked.
William nodded and Penelope continued. “You will be traveling with me on business trips. When Priscilla and I traveled we were able to share the same suite and cut back on the hotel expense. You being a male, well, the board was a little shaky about that. We’d have to have separate suites. Couldn’t stay in the same suite now could we?” she asked, as William looked on puzzled.
“I really wanted you for the job, so I told them you were a homosexual. That took care of the traveling accommodations problem as well as any sexual discrimination hassle. Pretty clever, don’t you think?” she asked sweetly.
“You told them I was gay?!” William asked incredulously.
“Yes dear. I hope you don’t mind. Don’t worry, they believed me. After all, you’re single, 25, live with your aunt, have a hairdresser’s license and graduated from a school that has a 95% female student body. Add that to the fact that you’ve applied for a job at a women’s fashion magazine, and well, what else would they think? Penelope added, shrugging her shoulders.
“You mean they don’t care? I won’t be ostracized? Wait though, I’m not gay. What if they find out?” William asked, still very confused.
“Don’t worry, they won’t find out. Of course you being gay is considered kind of en vogue . After all, this company is 90 per cent women, with very few straight men. As long as you do everything I say, no one will be any the wiser as to your sexual or lifestyle preferences.
We’re going to change your wardrobe, change the way you walk, talk and act. We’ll have you interact with all the girls in the office. We might even have you get friendly with the gay men here but you’ll have to be careful. We’ll even change your hair style, the scent you wear and probably your eyebrows!” she added, just a bit excitedly.
William sat puzzled, and then the age-old trap of money took over. “All right, I’ll go along with it Ms. Chambers. I’ll do anything you say. It sounds like such a great job, as far as the pay, perks, travel and working with you,” he added quite innocently.
“Why William, that’s so sweet of you to say,” Penelope blushed coyly. “Well then, let’s take care of all the paper work, I’ll introduce you around, and then you can start this coming Monday. That will give us five days to get you started into your new appearance and manner of acting,” she reminded him, much to his chagrin.
As he would say, quite frequently in the weeks to come, William answered, “Yes Ms. Chambers. As you wish, ma’am.”
“Come along dear, there’s lots for us to do,” Penelope smiled as she crooked her finger in a come hither fashion. William, her soon to be play toy, followed, very meekly.
Chapter Two: The Taming of the Swish
Although William Lane was not completely thrilled with his new appearance, job, and social status, both in public, at home and at the office, his Aunt Irene was. It never dawned on William, that he would have to appear to be a sissy swish 24 hours a day.
“It’s quite necessary dear,” Penelope stated. “In order for the charade to be successful you have to stay in character,” she explained. His aunt, so as not to show her collusion in the matter, acted disinterested. Today, while William and Penelope shopped, and went to the hairdressers together, Irene would visit her darling slave, Tanya Petite.
As William had been at the office for three weeks, it would be his second salon and boutique excursion with Penelope. The first had taken place the Saturday before he started, and had been only slightly embarrassing. He’d even begun shaving his legs, and now had a completely hairless body from the neck down. Depilatories had done that.
Meanwhile Irene had made it a point to visit Tanya each Saturday and had really looked forward to the visits. As she drove towards Penelope’s Arlington, Virginia home she recalled the weekend she had met Tanya.
Irene had been writing an article for her businesswomen’s publication, on the Sissy Maid Phenomena. She had done interviews all over the country, with women who had sissy maids. The common denominator she had found concerning the most feminine and well-trained maids was obvious. Each had attended academies run by Stephanie Strong. Irene decided a visit to one of these academies was needed to complete the article.
At the time, five and a half years ago, Ms. Strong, had five such facilities, one each in the states of California, Illinois, Texas, Florida, and her flagship school where she resided at that time, in New York. She had since opened academies in Georgia, Massachusetts, Arizona, Washington State, and Virginia. She now resided at the Atlanta facility, enjoying the milder climate. She had plans to open two more schools, one in Colorado and the other in Pennsylvania.
Irene’s article would really be a great help to the schools. She had decided to go to the campus in upstate New York to complete the piece. She had arrived on a cool morning in late October, two months into the 9-month term. Gloria, Ms. Strong’s, private sissy secretary, had showed her into Ms. Strong’s office. Right away Irene Lane could see the same polish and finesse in Gloria that she had seen in all the exquisitely trained sissies she had interviewed previously at the homes where they worked. Each one had attended one of Ms. Strong’s academies.
Gloria, or “Glory” as she was known to her friends, had honey blonde hair, just below her chin, done in a really cute spiral perm. She wore a tight, white silk blouse and a short black mini dress. Along with her four-inch spike heels and mesh hose, she was the stereotype of the little “hot body” secretary. Ms. Stephanie loved having her sissy employees and grads fit the everyday society stereotypes of the positions they were filling.
She welcomed Irene with a smile and a handshake. Ms. Strong was “30 something”, of medium height, with a lovely shape. She wore her hair in a long bob, slightly frosted, in a light blonde shade. Wearing a businesswomen’s pin stripe suite and 3-inch heels she was the picture of the confident head mistress.
She sent “Glory” for some tea and after it was served, dismissed her, then asked Irene what portion of the campus she’d like to see. “Well, I believe I’d enjoy seeing a class in session, possibly a meal in progress, maybe the beauty salon and a dorm and a room would be nice,” Ms. Lane requested.
“That won’t be any problem at all. Of course I insist you be my guest at a party this evening. After all it’s Friday and I expect you stay the evening. In fact I’d enjoy your staying the entire weekend. Trust me, I won’t take no for an answer,” smiled Ms. Strong.
The tour of the campus was excellent. Ms. Strong gave it with Gloria in tow. The class in session was a sewing class. She found the student quarters and cafeteria excellent. She enjoyed lunch in the instructors dining hall served by sissies attired in sun suits with ruffled seats. Somewhat interesting were the instructor’s quarters where sissies were hard at work cleaning and waiting on their teachers. It was the beauty parlor she found the most fascinating.
There were about a half a dozen sissies having their hair done and none seemed too happy with it. The headmistress told her that these were the last “holdouts” from the beginning of the term. “All the students have 2 months to voluntarily make an appointment and have something done to their hair. Either their future employer picks out what’s to be done or the salon manager decides. At the end of the two months, anyone who hasn’t had an appointment is given one,” Ms. Strong smiled.
She then added, “Actually few students enjoy their first salon visit here. The cute thing is that by spring break they can’t wait to make an appointment. By graduation the salon is so booked up we have to make appointments for the little dolls at salons in the nearby towns.”
“I believe it’s a combination of peer pressure from the sissy employees, the atmosphere here, along with the curriculum, and of course, a steady diet of discipline and hormones. I believe hormones are the key to everything, being cute, compliant, and pretty. Hormones are very important,” Ms. Strong said as she looked at Glory with a smile.
While at the salon, Ms. Irene noticed a very demure looking sissy in dark brown “Shirley Temple” type curls. She was helping an instructor put a perm in a sissy’s hair. She seemed relaxed and very well adjusted, dressed in a gray skirt and pink smock, and walking perfectly on 4-inch heels. Actually only the monogrammed S (worn by all sissies at the school) on her blouse gave away the fact she wasn’t a real woman.
“Goodness, all of your sissy employees are so perfectly girlish and feminine, Stephanie. They must be wonderful role models for the students. That sissy handing the wave rods to the stylist is a perfect example” Irene remarked.
“Actually Tanya is a student here. Of course she’s slightly advanced because she did take in the summer session. She’s also available for employment upon graduation. The woman that was going to hire her had to renege, although she did pay Tanya’s full tuition. The woman’s fiancee is from a very conservative family and abhorred the thought of a feminine male maid in the household,” Ms. Strong stated with a shrug of her shoulders.
“She’s certainly as lovely as your Gloria here,” Irene added.
“Yes she is. Tanya will be at the party this evening. I like to showcase my available students. Excuse me a moment. I want to remind the salon manager to make sure Tanya is dressed and done up to the nines,” said the efficient headmistress, as she walked into the salon office.
That evening Tanya was certainly lovely, assisting Ms. Strong’s personal sissy maid, Claire, with the serving of the main course, and later refreshments. She performed personal services for Irene that evening, bathing her, massaging her and dressing her for bed. At lunch Saturday, Irene inquired as to the possibility of hiring Tanya.
Stephanie smiled, “I knew she would be spoken for quickly. She’s a real jewel. Actually she’s yours for the asking. I told her previous employer I would attempt to recoup the tuition, but in your case, I’ll let you name your fee. I’d say the article you’re writing is worth at least half of the tuition involved.”
They agreed on half of the usual tuition to be paid by Ms. Lane to the previous lady. Irene would always say that Tanya “Was a steal.”
At present, William Lane was doing none to well as he sat timidly in the front seat of Penelope’s BMW, on the way to the second, of what he believed would be many, boutique and salon visits. The past three weeks has been a truly sissified experience, beginning with the Friday prior to his starting at the office.
Early in the afternoon of that day, Penelope had picked him up at Irene’s house and taken him to her own lovely home. There he had been met by Tanya, who had shown him to his room.
Penelope had told him to wear slacks, a shirt, underwear, socks and shoes. He was not to pack anything. “I’ll provide all your clothing from here on out William. Everything. Outerwear, under things, shoes and sleep wear. Your aunt has agreed to pack away all your other clothing for charity. She’ll include the tax write off towards your rent,” she stated.
That evening, after supper, he was dressed in his first unisex apparel and given his first lessons in “sissy mannerisms”. To help him get a little more “in character” both Penelope and Tanya put make up and perfume on him to get him “in the right mood.” Before they began his walking lessons, they “posed” him before a mirror, so he could see the dramatic effect the unisex apparel had on his appearance.
“We’ll be buying you clothing just like this at Amanda’s tomorrow. Of course you won’t be wearing as much make-up, unless you want to. Once we have your hair done, you’ll have no problem convincing the board of directors that you’re a sissy. Your interview with them is on Thursday morning of next week,” Penelope stated, as a matter of fact.
“I have to appear in front of the board like this?” William asked, looking at himself dressed in a ruffled mauve blouse, and a pair of gray flared slacks with matching waistcoat. His shiny patent leather flats were as feminine as his lipstick. His hair was in a topknot and with his hand on his hip he felt like Oscar Wilde.
“Don’t worry you’ll do fine” Penelope said and she had Tanya begin teaching William what she called the “sissy sashay”. Never in his life had he ever felt so humiliated! He followed Tanya around the room, left hand on hip, right arm bent at the elbow, wrist limp, the biceps tucked against the side of his chest.
As they walked, disco music played. Both William and Tanya wiggled their hips as Ms. Penelope said, “That’s it ladies. One, two, three, four, swing those hips, we look good, that’s the way, we girls sashay! Oh yes! Do it again! Very nice darlings!”
After an exhausting 30 minutes, William was permitted a short break and allowed a glass of wine, before beginning to learn to talk with a slight lisp and to use hand gestures, exaggerated eye movements, and words and expressions such as “so cute”, “just darling,” “to die for”, “fabu”, and “oh please!”
As it got late, Tanya drew him a bath, laid out gold satin pajamas with black ballet slippers and told him, “Mistress requests your presence at the fireplace in the den for a nightcap.”
William got there first, but the ten-minute wait for Penelope was worth it. Her light auburn hair shone in the candlelight, cascading to her shoulders, full and tousled from the recent shampoo and toweling. She wore a pale blue negligee and matching high-heeled sandals. No make-up except for a nice coating of creamy coral pink lipstick. Her heavy application of Opium left nothing to Sissy William’s imagination.
William was highly inexperienced with women, for his age. He’d been petticoat disciplined throughout his teen years. At secretarial school, his few sexual encounters had been with girls whose hair and nails he had done. Many of these girls he had known from slumber parties his aunt had put on, or sent him to, during his periods of feminization. Penelope knew this and went right for the jugular.
Before he knew what was happening William was silently placed on his back as Penelope took the lead. She sucked the breath from him with her kisses. She played with and nibbled his breasts once she’d undressed him. While the fire flickered on the hearth, this slightly cool evening in early April, she took her submissive sissy lover while riding them both to orgasm atop him, his arms pinned to the floor as she squeezed his dainty wrists.
During this she extracted both a confession and a promise from him. “You know darling, I could tell this evening, that you had worn girls clothes and make-up before,” she said smiling. “Now don’t lie to me dear! Did Aunt Irene dress her Billy up as her little niece? Tell me! Don’t you dare lie!” she said squeezing his wrists all the tighter.
“Yes Ms. Chambers, she did. Mostly when I was bad, but sometimes she’d make me dress as her Prissy, just for fun,” the sissy boy simpered.
“Prissy? Short for Priscilla?” she asked as he nodded his assent. “That’s perfect. We won’t even have to change name plates on your desk.” He looked at her puzzled as she continued, “Priscilla has her name plate permanently glued to her desk. I guess we’ll have to get you a new desk and plate unless you let us call you Priscilla,” she said with a chuckle.
“I’ll tell you what Prissy. I like my boy toys sweet and real femme. Doll up for me once in a while and I won’t tell anyone you ever wore petticoats. Okay?” said Penelope as William neared orgasm.
Just as he came, tears flooding from his eyes he actually said, “Yes Ms. Penelope, I’ll be your girl, I’ll be your Prissy.” She had her orgasm, shortly after.
Chapter Three: Office Sissy
As bad as the first shopping trip had been, life at the office was really tough. William wore nothing but ladies slacks, blouses and shoes, sometimes spandex Capri slacks, with a crop top, a linen jacket and 2-inch sandal high heels. His hair was now in a ducktail cut, with a tight perm, frosted in an ash blond shade. His eyebrows were two thin penciled-in arches that gave his face a look of mock surprise. He wore waxy white lip-gloss and clear nail polish with a hint of pink.
Whenever he served Penelope coffee, he used a small wooden tray and wore a full, ruffled apron, with bow tied in the back. Naturally, his new desk had not come in, and Priscilla’s nameplate was still glued to the old one. The women in the office, with the exception of Penelope would call him Prissy or Priscilla, then excuse themselves, and act as if they had made a mistake.
He did his boss’s nails whenever she asked and took no lack of kidding from the girls in the secretarial pool. More then once Penelope would have him give her a manicure or pedicure while she had another women or two in the office with her.
Even worse, after the board of directors (6 women, 1 gay man) had interviewed him, with great amusement, Duane, the gay male member of the board had begun to hit on him. Now, three weeks later Penelope had relented and agreed to let William have the ash blond frost shade, colored over with something darker. He of course had to agree to go to the boutique and purchase some kilts and jumpers to wear away from the office.
The first stop was Amanda’s, the same women’s boutique he’d gotten his first unisex apparel at. “Kilts and Jumpers? Well, they certainly can’t be worn with flat shoes and ankle socks,” said Amanda, asserting her professional opinion. When Penelope gave her a questioning glance, the owner continued, “Professionally, I’d recommend knee highs and slip ups for stockings and either clogs or 2-inch medium width heel pumps for foot wear.” It was settled that quickly.
Within ten minutes William was posing on a pedestal. Under the amused gazes and remarks of every woman and girl in the store, he modeled what amounted to skirts and dresses, while wearing heels and hose. Much to his surprise Penelope insisted he wear a red plaid jumper, white blouse with Peter Pan collar, black pantyhose and two-inch strap sandals to the salon.
When he objected in the dressing room saying, “My chest is flat, they’ll know!” Penelope returned with Amanda, some padding and a bra. Amanda feigned disgust, but was part of the whole scheme, just as the salon owner, Bridgett was. It took a light touch of make up, a set of clip on earrings, some jell to lift his perm, and a bow for his hair and William entered Bridgett’s Day Spa and Salon as Miss Priscilla Lane.
Luckily Penelope led the nervous Priscilla to the private treatment room. Penelope relaxed for a while reading Business Week. Bridgett, and her cross-dressed boyfriend, sissy slave and salon assistant, Tammy, took over and gave Priscilla a deluxe makeover. First of course they started with Tammy doing a shampoo, while the real ladies discussed color, style and make-up.
As Sissy Tammy used a strawberry shampoo to wash Prissy’s locks, the ladies came up with the scope of the beauty makeover. “Our new friend here is getting the works Tammy,” said Bridgett. I’m going to give her a very light trim, then color it all over with a dark brunette shade. Then some burgundy highlights,” she added.
Priscilla’s hair grew quite quickly and in the three weeks since her perm the duck tail cut had filled in quite a bit. In addition to coloring, she was also getting her ears pierced, a manicure and a facial cleansing followed by a coat of early evening make up.
While under the dryer, with her freshly colored hair tightly wound on large sized rollers, she protested to Tammy that the shade of polish she was giving her was “hideous”. Penelope overheard this. She shut off the dryer, lifted the hood, had Tammy continue and asked bluntly, “Since when are you an expert on nail polish, Missy Priscilla? I happened to have chosen that shade along with Ms. Bridgett. We both happen to think terra cotta is a lovely shade,” she said as she walked away.
She turned at the door and said, “You’ve insulted me and my friend as well as been rude to Tammy. I’ll deal with you at home.”
Priscilla’s comb out and final spraying left her with a smooth, very puffy and stylish flip, that framed her face to the chin. Her terra cotta lipstick matched her polish and the rest of her make-up was obvious but very tasteful. The black bow in her hair set things off perfectly. In the car on the way to Arlington, Penelope stated, “I simply adore what the girls did to you Priss! You’ll remain this way the entire weekend as per our agreement. It’s such a shame you’ve earned a punishment session.”
Arriving home Priscilla was told to go to the living room to wait, as Penelope explained things to Tanya. Penelope went quickly to the settee and said, “Over my lap Prissy. I haven’t forgotten your rudeness. If need be Tanya can help. As it is, she will be watching.”
Totally mortified the effeminate sissy boy went right to his mistress. The women lifted the hem of the sissy’s jumper and began paddling his bottom vigorously. As the sissy squealed, Tanya became aroused and wished Irene were there. Soon the mistress sent the maid from the room, completed the paddling and began hugging her sissy boy.
“Is mummy’s little girl all sorry for being bad? Will she be a good girl at the beauty parlor from now on? Tell mummy. Does sissy want to go lie down with mummy for a while?” Penelope asked as if she were talking to a ten year old.
Surprisingly enough, the sissy slave responded in kind, using the sweetest, most girlish voice he had used since aunt Irene had paddled and perfumed him as a teen. “Yes Miss Penelope, Prissy will be good and would love to be taken to bed by you,” said the pantywaist.
Soon Prissy was in a powder pink, fairy princess, baby doll set and Penelope in red satin pajamas. Penelope also had a strap on penis attached to her hips and in a remarkably short time had it inside Prissy’s well-oiled rectum. While she plunged it deeply inside, and as her love slave squealed with delight, Tanya was on the phone to Irene giving a report and begging Irene to come over during the week.
Throughout the weekend Prissy remained a demurely dressed teen, and curtsied and simpered to both Miss Penelope and Miss Tanya. “Did you have a nice weekend William?” Aunt Irene asked. “Yes ma’am. It was really lovely,” he answered.
Chapter Four: “Let’s Have a Party!”
“William. I really think it’s about time I met your aunt. After all, you and I are lovers. I want you to invite her to my home for the three day weekend at the end of May,” Penelope said as William gave her a pedicure one Thursday afternoon in her private office.
“Yes Mistress, of course I’ll invite her. I’ll do anything you say. Could I possibly discuss a problem I’m having, dear miss?” asked the simpering sissy.
“Of course you can my dear sissy boy. Is it about the office girls teasing you so much and Mr. Duane coming on to you dear princess?” she asked quizzically.
“Yes. How did you know?” he asked surprised.
“Don’t worry. I just knew. Don’t worry about Duane. I’ll take care of him. I’ll tell him you’re not interested. Besides I’m about to end this whole charade of you being gay anyway,” she smiled as he looked up at her as one does to a true heroine.
“As for the girls, well, you could interact with them more. We’ll talk to your aunt about it when I meet her. Possibly you could have a slumber party with them at your aunt’s house,” she added, knowing she had struck a nerve.
He now looked up at her, his mouth agape, as she said, “Don’t tell me that a sissy mummy’s boy like you never had a slumber party? Tell the truth now Prissy girl.”
He nodded as she continued, “Then I’m sure Aunt Irene will agree with me when I mention it to her.”
Indeed Irene did. She acted so thrilled that she had been invited to Ms. Chambers house and even more thrilled to be there. During dinner she made a fuss over the lovely maid and when the slumber party was brought up she was ecstatic.
“My goodness, what a lovely idea! Such a clever way for my Billy to make friends with the girls at the office!” she said with a huge smile. “Oh Billie dear this is wonderful! You can dress as the hostess, set hair and do nails. Just like when you used to dress as my little Princess Prissy! Oh my! I’ve let the cat out of the bag, haven’t I?” she said, covering her mouth with her hand and acting upset.
“No Irene. You haven’t. William, or should I say Priscilla has begun to fill me in on the dressing sessions,” Ms. Chambers remarked. I think this is just what we need to do to make Prissy a big hit at the office,” she added.
“Do you mind at all that my nephew has sissy cross dresser tendencies?” Irene asked.
“Absolutely not! In fact I find it interesting and quite appealing. I believe that a women like myself and a boy such as William can have a very rewarding relationship,” she said with much candor.
This put chills up William’s spine and did much for both Tanya and Irene.
The two ladies briefly made a few plans for the party before Irene excused herself to take a nap, suggesting to her nephew the assist the maid with the lunch cleanup.
Once things had been cleaned and straightened, Penelope excused Tanya and told her to check in on Irene before taking a nap herself. This left Penelope and William alone. Penelope took her sissy’s hand, walked him to the couch and after she sat, had the pantywaist sit on her lap. She began to cuddle and arouse him.
“This weekend you and I will still be playing dress-up in private honey. In fact I find your aunt so nice I’d like to surprise her with you in full feminine attire, hairdo and makeup,” she said as she kissed him.
“Please darling,” the sissy begged, don’t have me dress in front of Aunt Irene.”
“Sorry dear. I think it’s a must. It would please your aunt and me immensely and it’s about time we stopped hiding this from her. To my room my sweet! I had a lacing bar installed this week and we’ll not waste it,” said Mistress Penelope as she drug her swish boyfriend by the hand to her room.
Once our “Prissy” had been stripped naked, she was bathed and shaved. Her mistress had her cover her body with a honeysuckle-scented lotion. Then Penelope powdered and perfumed her quite heavily with Shalimar. Taking her sissy to the lacing bar, Penelope cinched her waist in until the pantywaist begged her to stop. Prissy was near fainting.
Prissy wondered why mistress didn’t gaff her but would soon find out. A padded bra, garterbelt then hose and 3-inch heels and Priscilla was given a dark, floral print peasant skirt with pink blouse to wear. “Look in the mirror my sweet, you look darling,” said Penelope. “Let’s set your hair and do your makeup. Then we’ll put some jewelry on you,” she added.
Prissy was surprised that Penelope would bother to set her slave’s hair for her, as she sat down at the vanity. Normally it was Prissy doing her mentor’s locks. Penelope used a cherry bark scented lotion, and medium sized curlers, which she rolled extremely tight. When Prissy whined and complained, Penelope made her hold her hand out, palm up and slapped it with a hairbrush saying, “Stop that sissified whining this instant you little swish. You need the rollers tight for the set to hold. You know that as well as anyone.”
Once the set was complete Penelope very carefully pulled a pink satin stretch turban over Prissy’s roller set hair. She made sure the fringe rollers were visible and that the turban was pulled tight enough to shown the outline of all the rollers. She then used a large white ribbon to fashion a bow around the turban, which she positioned right on top of Prissy’s head in a real display of sissy fashion.
Prissy’s makeup was next. A nice foundation, followed by blusher and powder, set off by white cream eye shadow and deep rich dark mascara and eyeliner. A heavy, double coat of dark red lipstick and Prissy was ready for the next stage of her humiliation.
Her mistress had her pull her panties to her knees while mistress pinned her sissy’s skirts up all the way around. She marched the lipstick faced, hair curler wearing, sissy boy to the full-length mirror, saying, “Hold your hands up shoulder high, spread your fingers and limp your wrists dear. I’m going to condition your penis. Look at yourself and realize what a sweet sissy you are. Take in the whole picture darling. When you come, squeal like a pansy and call yourself a little prissy, sissy, missy.”
Penelope began to masturbate the humiliated sissy, occasionally stopping to slap his ass with a hairbrush. When he got really hard she let him use his right hand to play with himself, making him hold the other hand even higher in the air “sissy style.” She then said, “Wiggle those hips while you play with your sissy clitoris, wave that free hand and do a little sissy dance honey buns. That’s it, swish and sway, but stay in place.”
All the humiliation, feminine appearance, spanking and stimulation finally reached a crescendo and Prissy spurted her sissy cream all over the full length mirror, screeching out her sissy mantra. She nearly collapsed, and had to be seated at the vanity and made to clean herself up before being led to her aunt’s room. Tanya had left to clean up herself and Aunt Irene acted pleasantly surprised.
“Tanya and I will be going out shopping Ms. Lane. We’ll leave you and Prissy alone for the rest of the afternoon. Your niece wants to reminisce about old times” said Penelope as she closed the bedroom door leaving Aunt Irene and her sissy niece alone. The two had a wonderful time, taking a walk around the neighborhood holding hands, then returning to the house to do each other’s nails.
“You should prepare dinner this evening my child. I’ll call Penelope on her cell phone and see when she and Tanya plan on returning,” said Irene. After a brief conversation with Prissy’s new boss she put an apron on her sissy nephew and supervised the food preparation and the setting of the table. Finally Prissy was taken to the vanity in Irene’s room and her hair was taken out of the rollers and styled into the same modified bouffant flip that Madonna wore on the cover of Good Housekeeping.
The final touch was the red bow pinned to the side of the sissy’s hair and the dangling, bone white ear rings placed in our heroine’s pierced ears. Both Tanya and Prissy’s mistress loved the sissy’s new appearance. Everyone praised the meal and after coffee, the final plans for the slumber party were made. Monday at the office would be a real surprise for everyone.
Chapter Five: Prissy, Mincing, and Nice
“Put on that apron and you can polish the furniture here in my office Prissy. I’ll be back in 30 minutes or less. I’ll explain things to the board, and pass out the invitations to the girls in the secretarial pool,” said mistress Penelope. Prissy put on his apron and curtseyed as mistress left her private office.
Prissy was still dressed pretty much unisex, although his frequently styled and set hair had taken a more or less feminine set. Beginning with the previous Friday he now set it every evening. He was happy and relaxed. Penelope was going to tell both the board and the office girls that he wasn’t gay. He polished the furniture, humming some tunes, occasionally answering the phone and taking messages.
Penelope returned smiling and seated herself in the large chair behind her desk. She motioned for Prissy to take the chair opposite hers, and she said, “I have told the board and all the girls that you’re not gay. I explained that your appearance and effeminate background stemmed from your aunt using petticoat discipline with you as a teen.”
William began to protest but before he could, Penelope raised her hand in a stop sign and continued. “I went on to explain that you were actually a heterosexual, submissive, sissy, transvestite, coming out of the closet,” she explained, obviously pleased with herself. “It’s really wonderful Priscilla. Everyone here wants to help you come out at the office.”
Prissy felt trapped. She knew better then to complain. She’d spent her share of time over both her aunt’s lap and mistresses’ lap for complaining. Still she didn’t want to dress as a female 24/7, but knew that was where this was all heading. She’d just grin and bear it, and when financially able, she would strike out as a male on her own. “Thank you Penelope, I really appreciate you doing this for me.”
“You’re welcome sweetheart. Now go sit at your desk. I’m sure all the girls will be by to thank you for the invite, as well as to pledge their support. The board members may also call you in to let you know they’re with you,” said Penelope beaming.
Prissy took off her apron and went to her desk and soon the girls in the pool came by, one by one, to assure her they would be at the slumber party. In addition, they let her know that if she needed anything like makeup tips, fashion consultations, or would like to shop or do lunch that they were all available. “From now on Priscilla, you are one of the girls,” said Toni Sands, the head of the secretarial pool.
After lunch she was called into the boardroom, where each member of the board pledge their full support. After each member had spoken, Tamara Cameron, the board president added, “We all expect you to keep up a convincing feminine appearance Priscilla. You are not to come to work looking like some clownish, garish, drag queen. You may avail yourself of my personal hair stylist and I know of a modeling school and beauty pageant charm instructor who can make certain you’re very passable where posture, speech, gestures, mannerisms and comportment are concerned.”
Priscilla thanked her and Ms. Cameron closed by saying, “I think that next Monday would be a good day for you to come dressed as Priscilla. I understand there is a slumber party being held. That will be perfect for the girls to get to know you as a female. You may go dear. Congratulations.”
Friday after work Prissy went home and her aunt helped her get ready for the party. When the girls began arriving at eight in the evening, Priscilla greeted them in a cute leather mini, with white silk blouse and 3-inch heels. Her breasts were padded to a B cup, and her waist was scrunched in, nearly to fainting, with a “plus” five corset. She was playing the “hot chick”, wearing mesh hose, because Penelope had said she may stop by.
Her hair had been pin curled and was ultra curly, pinned off to one side, shiny with jell and smelling beautifully, with a sweet scented hair spray. Her make-up, slightly overdone, with glistening red lips, made her appear the little tart who was hoping her lover would stop by.
Penelope did come and was quite pleased, but Prissy became quite disappointed when both her aunt and Penelope told her she would have to join the other girls in having her hair set and green facial clay put on. “But Penelope, I got all dolled up for you,” she whined.
She was overheard by Toni who told the rest of the girls who began teasing Prissy. Finally Toni spoke up. “Prissy. If you will do the hair and nails of myself, the other five girls from the office, your aunt and Tanya the maid, we’ll let you stay pretty for Ms. Chambers.” Prissy agreed and got started. Of course she had some help, in doing 8 sets of hair and nails. Tanya, in full serving maid's regalia, not only helped Prissy serve the food, but also assisted with the beauty services.
By two in the morning, Prissy was exhausted. Everyone was asleep as she tiptoed to the guest room where Penelope was sleeping. “Oh princess, get in something pretty and come to Mistress,” Penelope said. Little did Prissy know that in spite of the rollers in their hair her aunt and Tanya were now making love. Also the six girls from the office had paired off in loving, lady-to-lady sex.
Penelope dominated her like never before, using handcuffs to restrain her and a ball gag to silence her screams. The screams came because mistress used a belt on Prissy’s butt for the first time.
It was the following afternoon that Prissy finally discovered what was going on. She and Tanya had combed everyone’s hair out after breakfast and saw the guests off. After cleanup, Irene decided to nap, as did Penelope, Prissy and Tanya. Everyone was tired from the week’s work, the excitement of the party, and staying up so late. Prissy awoke about a half hour into her nap, thinking she had heard a squeal. Penelope was still sound asleep.
Priscilla went down the hall. Another squeal sounded. It came from her aunt’s room! She entered without knocking saying, “Aunt Irene, are you all right?” The sight that greeted Priscilla, made her gasp. Tanya, in corset, leather bra and spike heels was bent over the bedroom dresser, her hands clutching the sides. Aunt Irene wearing a black satin pajama top was behind Tanya, wearing a strap on faux penis.
The penis was deeply buried in Tanya’s well-oiled, plump butt, and Aunt Irene thrust it in and out expertly. The excitement, the lack of sleep, the hormones she had been started on secretly a month ago, and the tightness of the corset, all added up. Priscilla put her hands to her gaping mouth, and squeaked out a sissified, “Oh my land?!” She then swooned like a antebellum, southern belle, fainting onto the bed.
The excitement was too much for Tanya also. An exhibitionist, she screeched and came all over the antique dresser. Once Tanya had calmed down, Mistress Irene sat her in a lounge chair just as Penelope entered the room, saying, “I was afraid of this, but we had to tell our little milquetoast sooner or later.” She went to the bed saying, “Well she fainted like a dizzy chorus girl. I seriously doubt at this point she’ll put up much resistance.
Irene and Tanya nodded as Penelope really took command. “I’ll keep her at my house for the next couple of weeks. I’ll have the company doctor put her on tranquilizers. I’ll use an office temp until she comes to grips with this. Tanya, get me some smelling salts, some water and a bottle of Librium. Then we’ll get her in the car. She’s coming around right now,” Penelope said in a commanding tone.
As it was, Priscilla was able to take things in stride. She was really quite compliant. For most of the rest of the day she relaxed and was given the entire story. She returned to Penelope’s house with her that evening, and over the next week moved in, as Tanya and she traded places.
Monday she wore full female attire to work and was welcomed by everyone. Her time card now read Priscilla Diane Lane. She enjoyed riding in with Penelope and changing her hairstyle and “look’s”, every week or so to please her mistress. For the time being the two lovers decided to stay unmarried though they were as devoted to each other as any mistress and sissy could be.
Tanya loved the way the Atlanta campus of Miss Stephanie’s new school looked. It was so modern. She enjoyed seeing her old headmistress again and some of the staff Ms. Stephanie had taken along with her. She also enjoyed eating as a guest in the instructors dining hall. Getting to give a sissy, dressed in hot pants, tube top and four-inch heels, her lunch order was fun. Especially when the sissy curtseyed and said “Yes ma’am.”
After lunch, she, Irene and Prissy took a tour of the school, while Ms. Stephanie and Penelope went to the private office of the headmistress. The tour took some time, which was good, as the conference between the two dominant business ladies was quite long.
“Penelope, I am really proud of my chain of academies. However, I don’t think this is the right place for your Priscilla. You have to ask yourself if you really want a maid. Think about it. Prissy has housekeeping and hostess talents. She is also a fine secretary and hairdresser. From what I can pick up on, I believe both of you have a satisfactory sex life. What I believe you want is a polished concubine and trophy sissy. Here’s what I suggest you do,” the well-known headmistress said, as she developed a custom made plan for her new friend...
The heading atop the stationary read, Madame Dupree’s Boarding School for the Feminine Arts; Boston, Massachusetts. The room was very feminine in design. The young lady, possibly 25 or so was also the picture of demure femininity and very polished.
Her dark auburn hair was in an attractive French roll, her makeup perfect. She wore a white linen Chanel suit with matching heels. Her ginger matte lipstick and nail polish matched. Her pink shell earrings were expensive and fashionable. She was slim and dainty, with pert breasts she was very proud of.
She began her letter:
My dear Penelope,
I’m so thrilled that you and Aunt Irene are coming to my graduation next month. It was wonderful seeing both of you at spring break but I miss you terribly my dear. At least during my nine months here I got to see you then, and at the holidays. I’m sorry Tanya can’t make it, but it think it’s wonderful she would stay at our house and look after and assist our new sissy maid.
That is so sweet of you to hire a maid for me from Ms. Stephanie’s school, as a graduation present! From the Atlanta campus even! I’ll bet she’s the most darling little southern belle! I’ll bet the two of us will have such fun planning meals and parties for you and your friends! Such a pretty name also, Nicole. Having her around will also let me keep working for you at the office. It will be different being your receptionist. How are you and your new secretary, Gregory, getting along? You did say he was gay didn’t you? I remember you saying that all those tall, handsome, single, men in their early 20’s always seemed to be homosexual.
We’ll darling. I’ll be going. Have to wash and set my hair for tomorrow. By the way, I’m going to have some light auburn tints put in my hair for the ceremony as well as a body wave. I’ll wear it up with little curls on top. Won’t that look cute? Good night my love. Please call and write. I hope you and Greg have a nice time in Bermuda on your business trip. One month!? That sounds like such a long, boring, time to be on a business trip!? Especially in a lovely place like Bermuda.
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