Mistress Psyche's Feminization Fantasies


Sissy Girl Stories


Teased and Tamed

 by Priscilla Gay Bouffant

 (A feminist probation officer is convinced that “sissy girls just want to have fun”.)

                                                Chapter One: Naughty Nancy Boys!

Danny Pierce, not quite twenty-two years old, sat in the office of Rita Carson, with his Aunt Cheryl who smiling smugly. It had taken Cheryl Danvers two full months to get her nephew’s case transferred over to Ms. Carson’s office. Rita Carson was a probation officer who applied her special “Male Makeover Method” to most all of her unruly youth’s problems. 

Danny was an ideal candidate and knew full well what was in store for him. Rita began her usual lecture. “Well Danny I think you know the options involved. Two years at the detention center or the same amount of time being sissified and feminized by my special Triple M curriculum. If I recall, when I took you on a tour of the women’s center, you were terrified. I can’t imagine your holding out too long at the men’s facility,” she said smiling and then winking at Cheryl Danvers. 

Danny shivered. It was true. A week ago his aunt had dropped him off at Rita’s office. First he had been taken to a dressing and shower room by two female officers. They had roughly stripped him, shaved his body with cream and a razor. Then they had coated him with depilatory and threw him in a shower. Coming out of the shower, he had been toweled, perfumed and powdered, and then he’d been made to coat his own body with scented lotion, before being told to dress. 

The clothing he wore included a girl’s flowered cotton panties, pink knee-highs, a white shell top, pink hot pants and red sneakers with pom poms on the laces. A hair stylist had set and styled his hair into a cute page and put peach nail polish and lipstick on him. He’d tearfully been paraded through the women’s detention center to the hoots and catcalls of the women.

 “Hey sweetheart, who set your hair? I’ll trade you some curlers for some smokes! Hey sissy fag, be my girlfriend?” The shouts got worse and Danny hysterically begged to be taken home. His thoughts of the horrid event were broken by Rita asking, “Danny, do you have any idea what would happen to a cute, slightly built young man like yourself at the male facility?” Danny didn’t answer.

“I’ll tell you dear. You’d be considered Fresh Meat. You, with your pretty, long hair, would become the girlfriend of the biggest, toughest hood in the place. They would fight over you. Probably call you Dani, or Danielle,” she laughed slightly and let things set in. Looking at the young man, she thought with his dark hair and smoldering eyes, he resembled Denise Sands, that gorgeous, new, teen rock star. 

Rita had already mentioned this to Cheryl, and they both considered it a cute girls name for whenever Danny begged to be dressed as a girl and not as a sissy boy. All of Ms. Carson’s sissy boys eventually wanted to be dressed as girls. They soon tired of the public humiliations they suffered as sissies.  

It was much less stressful learning to pass as a pretty girl and have people perceive and accept them as such. Rita’s own nephew, Christopher, was already breaking. He had recently asked his mother, Helene, about what dress size he was. 

“Besides this dressing thing, what else do you expect me to do?” Danny asked. 

“Ms. Danvers. Why don’t you fill him in?” asked Ms. Carson. 

Danny’s aunt began, “Well dear, for the first few weeks you’ll stay home and keep house. You’ll practice hair and nail care on yourself, your two cousins, Ronda and Sharon and me. Once you’ve adjusted, the four of us can split the housekeeping and you can start working at my main salon. You’ll also help out next door at my partner’s boutique.” 

Danny’s aunt owned a small but profitable salon/boutique chain called Tresses and Dresses, along with her partner Tina Goodman. Tina was the mother of Danny’s girl friend Barbara. Danny cringed as he realized Barbara knew of the plan of discipline being enforced upon him. In fact she was all for it. She had even picked out Danny’s new sissy name. Pansy. Pansy Pierce. 

Until such a time as Denise, the girl, emerged, Pansy would be the sissy’s new name. 

“Well, that just about covers everything. Cheryl, if you have nothing to add, why don’t you take Pansy here to Dr. Cane’s office so she can give Pansy an exam, a booster shot and some pretty pills,” Ms. Carson said laughingly.

Pansy cringed at the new name and also at going to Dr. Cane’s office. His cousin Sharon worked as the head nurse there and was exited about helping with the hormone therapy. Although an obstetrician/gynecologist, Dr. Cane had several sissy patients in various stages of transformation. Pansy knew the doctor enjoyed her work and was good at it. 

As Pansy and Aunt Cheryl drove towards the doctor’s office, Ms. Carson’s nephew, “Chrissy the Prissy Sissy Missy” (Chrissy, for short) was being prepped for his first meeting with his new boyfriend Percy. His mother, Helene pulled into the parking lot of the local strip mall and walked with her sissy son to the Cosmetic Center

Chrissy, just past his twent-third birthday, had on tight, red, Capri slacks, a white halter top, black, three-inch spike heeled sandals, and jangling charm bracelets. Underneath his pink hair net he wore his coppery red, shoulder length hair in large, baby blue curlers. His flame red nail polish was the only concession to make-up, as he would be having it applied at the Cosmetic Center, by his girlfriend Sadie. Actually, Sadie had a new boyfriend for the time being, Billy King, a college baseball player. 

As Chrissy sashayed to Sadie’s workstation, he dreaded the whole week in front of him. A makeover by Sadie, public humiliation as a sissy, housekeeping, sissy lessons in walking and talking, all capped off with a “getting to know you” date with a homosexual boy from the college ballet troupe, Percy. The sight of the sissy boy entering the store sent many ladies into hysterical laughter. 

“What can I do for you today Chrissy,” Sadie asked with a big grin. 

“Mother says that I should get a makeover. I need a new look for my date with this new boy who’s coming to the house this weekend. Whatever appearance you give me I have to practice all week,” the humiliated sissy answered. 

“A very wise choice, sugar. Here let me help you up on the high makeup stool honey. There we go. Ups a daisy! Good girl!” said the very amused Sadie. The dominant girl lavished cosmetics all over the sissy boy’s face, and soon he had a garish, overdone, almost hideous masque of makeup, covering his sad little face. 

Sadie stepped back so the boy could see, and she and his mother had a good chuckle. Sadie especially liked the Magic Mocha lipstick her ex-boyfriend now wore. The young man took on a look of shock and dismay. Sadie decided to “tone things down a bit.” 

By the time Chrissy was at the register paying for the makeover, and all the cosmetics his mother had made him purchase, he was presentable. He looked at all the feminine items in his basket, including the Burnt Crimson hair color, by Loreal, and wanted to burst into tears. 

Unfortunately, his flat chest, and his overdone sissy walk and mannerisms, told everyone he wasn’t a girl. The woman in front of him at the register asked Helene, “Is there some sort of fraternity initiation going on? I just came from Dr. Cane’s office and a young man was there dressed similar to your son. Oh excuse me. How rude. I only assumed he was your son,” the women said apologetically. 

“Oh, that’s quite all right. Yes, this is my son. No, there is no initiation. Possibly the boy at the office has the same probation officer as Chrissy. You see, Ms. Carson, the officer, disciplines her male charges by dressing them as sissy boys, or as girls. It’s quite effective,” Helene Porter answered. 

“You mean he’s being punished? She makes them all dress this garishly and ridiculous?” the woman began laughing as did the lady cashier, Ms. Helene, and Sadie, who had come to the front of the store, to spray Chrissy with perfume. Chrissy could only limp his wrist and giggle at his sorry plight. 

Pansy was actually faring slightly better at the doctor’s office. His cousin Sharon had been discreet when she came for him and had left the exam room while he changed into the smock he was given. The very, “politically correct” Lydia Cane swept into the room smiling, with Sharon in tow.  

Dr. Cane had the gift of making all her sissy clients feel comfortable and normal. She had this effect on Pansy. During the exam she used phrases such as “We girls know, don’t we Pansy?” We don’t want to be taken for a sissy, too long, do we dear?” We’ll have you out of training bras in no time. Isn’t that true Sharon?” 

Pansy left feeling very at ease, the hormone booster she’d been given already coursing through her system. She held a six-month supply of “pretty pills” in a bag in her lap all the way home. As soon as she was in the door, her cousin Ronda took Pansy in tow to the converted garage, attached to the Danver’s residence. Cheryl had used this as her first salon, before beginning her chain. 

Tina Goodman, his girlfriend’s mother, and his aunt’s business partner, was there also. Both she and Ronda had spent much of the morning getting rid of his male clothes. They had redecorated his now feminine room, stocking that room with sissy and girl clothing, accessories, cosmetics, etc. Tina would now have her hair done by Aunt Cheryl and Pansy would get a wash, cut and set by cousin Ronda. He hoped Barbara Goodman, his girl friend didn’t show up. 

Ronda put the salon cape on him and as she shampooed his hair he relaxed as the three women engaged in “girl talk.” Once Ronda began cutting his hair, he joined in the conversation. She left his hair just to his shoulders, blunt cut, with a cute fringe of bangs across the top of his plucked eyebrows. She then used a pink jell and big plastic rollers to set his hair. Covering his rolled hair with a hair net she helped him out of the chair. 

She patted his butt saying, “Let’s leave mom and Tina alone. I’m going to begin showing you the housekeeping and meal routine. By the way, expect to set your hair frequently, here, and at the salon. Also expect to do housework, perform your salon duties, and run errands with your hair up in rollers,” she added as she took his hand and led him to the living room. 

There was one thing Pansy was wondering about, not that it was any of his business. While he was having his shampoo, he had glanced over at Aunt Cheryl who was washing Tina’s hair. At the same moment, Cheryl was planting a sexy kiss on Tina’s pink lips. Tina was quite receptive, giggled and tongued Aunt Cheryl back. The two had smiled at each other as only lovers do. 

                                                Chapter Two: Makeover Magic

 Life for the “soon to be” Denise (Pansy), and for Chrissy “The Prissy Sissy Missy” differed somewhat. On the one hand Cheryl wanted Pansy to dislike being a sissy so much she would beg to become a girl. Denise would then be “born.” Of course, some humiliation as a sissy was in order. Denise would more appreciate being a girl, and Cheryl would have her revenge for the trouble her nephew had caused her. 

However, Chrissy’s mother and aunt were using the delinquent young man as a sort of experiment. How far could a rowdy youth resist and remain a sissy? How long after a punished young man gave in, could one keep the delinquent a sissy, before letting him become a girl? 

Barbara Goodman, Pansy’s girlfriend had finally dropped by the house on a Saturday while Pansy was doing housework. Pansy looked so cute. He had a baby blue romper with a navy blue leotard. His hair was up in small, pink rollers and matching hair net. White nail polish and hot pink lipstick, with a honeysuckle perfume, was really making him feel sweet and girlish.

 The Mary Jane’s with two-inch block heels aided his mincing walk. The white anklets, turned down to show the lacy tops, really set things off. He’d begin working at the salon and boutique Monday because of his “excellent progress” his aunt had said. She had also told him his apparel for the salon would be “more sophisticated.” 

Barbara, (whom was often called Barb, or Babs, and never, ever, Barbie) was like a member of the family. As such, she had knocked, and getting no answer had then come in. She hadn’t seen any cars but had been told by Ronda, Sharon and Cheryl, that Pansy would be home. Part of her job was to convince Pansy to “let go” and begin experimenting with dresses. 

She came upon her sissified boyfriend, and surprised him while he was primping in the hall mirror, touching up his lipstick. “Oh goodness Barbara! You frightened me!” Pansy cried as he fluttered his eyebrows and held the lip liner brush in his limp right hand and the holder in his left. 

Putting things away in his purse, he then became embarrassed at being seen by his girlfriend in such a state. He self-consciously patted his rolled up hair and blushed. His girlfriend attempted to put him at ease. “You look really sweet Pansy. I knew you would. Ever since your aunt decided to make you over I have though you’d make a really stunning young woman,” Barb said emphatically. 

Pansy wasn’t sure how to react, but very sweetly said, “Thank you Barbara.” Not wanting Pansy to feel silly, Barb then reached out and hugged the sissy boy as well as gave him a kiss on his blushed cheek. Pansy appreciated it. 

Babs knew how she wanted to proceed. First, while she relaxed and read a magazine, she would let her sissy boyfriend complete his housekeeping. She would occasionally interrupt him to have him get her a glass of iced tea, or water. She was tempted to have him do her nails, but that would take too long. She would save that for another time and have him do her hair also. 

She giggled to herself. A boyfriend who did hair, nails and windows! Cute! Once housework was complete she knew where to go from there. “Done already sweetheart? Wow, you’re good! Look, sooner or later you’ll want to pass as Denise,” Babs said. Pansy looked at his girlfriend quizzically. “Oh, I’m sorry. Denise is the name we picked for you whenever you decide to go femme,” she answered. 

“Anyway, why don’t we have lunch, chat and then I can help you pick out a few things to wear. Girlish stuff. Just around the house. Just you and I. You can comb out your hair, fix your face and I can give you a charm lesson or two,” she said as she touched the sissy’s face and gave him a very friendly kiss on his pink lips. 

Pansy was sold and said, “Okay. What would you like for lunch Barb? By the way, my hair is set in these small rollers because Aunt Cheryl wanted to see what my locks would look like with a sort of perm look,” the young man said, blushing, and waving his hand in a really overdone feminine way. 

Lunch was tuna sandwiches with iced tea and the happy couple went into Pansy’s room after the sissy had cleaned the lunch mess. Babs quickly noted the pedestal and lacing bar in the corner of the room. “I think we’ll try that out Pansy. We want to give you a realistic figure. By the way honey, for this exercise I believe we should call you Denise,” the young woman said firmly. 

“Denise honey, did you bathe this morning?” Babs asked, as the young man nodded. “Good then strip down to your panties and get on the pedestal,” she added. 

Soon the sissy was having his waist pulled in with a cinch, to very girlish proportions. Barbara had decided to put Denise into a summer dress and had to forego the use of a full line corset. When Denise began to complain about the tightness, Barb let her know how lucky she was. Denise of course was near fainting by now but it didn’t matter to her new mistress. 

“Denise sweetheart, this is nothing. It’s just a simple waist cinch. Wait until we attend our first formal together and I put an ankle length, hobble style gown on you. Believe me honey, we are talking about a full-bodied, slim line corset for that one dear. A real figure former,” the dominant young woman admonished her slave.

Once properly cinched, Denise was given a garter belt and sheer hose, then a really cute, floral print sundress. The dress was sleeveless, came to the sissy girl’s knees, and had a scalloped collar. Once at the vanity, Babs decided to slightly dampen the sissy’s tightly rolled locks and after removing the rollers she finger styled Denise’s hair into a sort of wet, baby doll, fresh, perm look. 

Her makeup was equally devastating. Deep cherry red lipstick and blush, along with curled lashes gave Denise the look of a young “hot body,” her lips so pouted and her eyes so open and innocent. Posed in front of the mirror Denise saw how pretty and sexy she could be. For the time being Barbara would keep her hands off her. 

Strap sandal high heels completed the ensemble and Denise was propelled toward the living room, tottering slightly on the heels. The charm lesson began with some gestures such as getting hair out of one’s eyes daintily. Proper sitting, getting up, and walking exercises followed this. 

Once Barb was satisfied, she began with some elocution and phrasing lessons, adding in dainty hand gestures. Then she decided to add a little wiggle to Denise’s walk. Finally she had Denise try and put it all together. As Denise began trying very gamely, Babs would correct her and show her the mistakes she was making. 

Soon enough Denise stopped and began to sob, “Please Barb? This is so stressful. Have pity on me? Oh no!” the sissy cried and fell on the couch whining hysterically. Barb, full well knowing that this was the result of the hormones, began to hug her and kiss her. Soon the couple became aroused. Babs took the sissy into his femme bedroom and placed him on the bed. 

Reaching underneath his sundress she pulled down his panties and began to massage his clitty. Then she took off her own slacks and panties and had the feminine young man begin to massage her clitoris. Barbara cautioned the sissy never to come until Mistress Barb did. 

As Barb became very close to climax, she stopped touching the sissy and told him to rub her harder and faster. Barb soon reached an orgasm. Once she had relaxed she lubricated her sissy’s shaft and had the sissy stand up in front of the bed and do a dance, thrusting and wiggling his hips, and waving his arms overhead. 

“Dance sissy girl dance!” Babs implored as Denise did a real disco imitation, as they both laughed. Soon Denise was pumping her sissy cream into Barb’s hand. She mewled and simpered like a little fairy girl and tears came to her pretty eyes. She collapsed with her mistress, full well knowing she would dress and play again if told to. 

That evening Barbara helped Denise prepare dinner and both Denise’s aunt and cousins were quite pleased to be served dinner by the very girlish Denise. At bedtime, Barb was encouraged to stay, and around one in the morning she went from the guest room to her sissy slave’s room, where she introduced her sissy to having his mistress on top. 

Denise learned very fast that her mistress knew best and was always right. Barb’s next session with Denise would include a vibrator and faux penis. 

                                    Chapter Three: Sweet Little Swish 

Percy was always so excited to see his Prissy Chrissy! From their very first get together at Chrissy’s house, he had been really in love! Now Chrissy’s mom was going to let Chrissy go the college sophomore formal with him, with Chrissy as a woman. He always knew Chrissy would make a lovely female and couldn’t wait to see. 

Actually Percy loved Chrissy as the sweet, overdone sissy he’d known these past few months. The first time together had been so special! 

On that occasion, Chrissy’s mom had had her sissy son to roll his hair that morning after a scented bath. While under the dryer she had painted his nails a soft coral pink. Once out from under the dryer she had slimmed his waist with a cinch, then put panties and a training bra on him. She then made Chrissy dress in a pink, sleeveless, knit ribbed top, with a turtleneck collar. Then she’d added matching shell earrings. White anklet socks, black, three-inch high heeled pumps and silver lame stretch slacks that gave Chrissy a really sexy appearance. The hairdo Ms. Helene planned would be the kicker. Sharon, Denise’s hairdresser cousin, dropped by to tease, comb and spray the sissies shoulder length, coppery crimson hair into a really dated, bouffant beehive, complete with bangs, and a big pink bow in back! 

Chrissy wanted to cry and faint, but Percy was in love! No real girl would dress like this! Only an over sexed sissy would. Percy was so thrilled as he and Chrissy held hands and took a walk around the neighborhood. It was then that Chrissy noticed how strong Percy was. As a dancer he was in great shape.  He exercised, and did strength conditioning. 

Chrissy’s mother noted the same thing as she left the two alone to go shopping for about “Five hours,” she said as she closed the door and winked at Percy. Percy had a slender waist, wiry muscled arms, and decent sized shoulders and was lithe and agile. Chrissy on the other hand did his exercises to lose weight, flatten his tummy, and plump up his boobs. 

The most weight he lifted was a laundry basket full of wet clothes, and was as weak as a kitten compared to even an average man. Percy took no time in smooching with Chrissy. 

“Oh my dear but you are so sweet! You smell so very pretty! I just adore the mixture of honeysuckle and sandalwood, Chrissy!” said the obviously smitten man. Finally Chrissy wore down, tiring of talking about, “Not on the first date,” and “I’m not really a sissy,” and the two new lovers were in the bedroom. 

Chrissy now had only questions not objections. “You brought condoms, didn’t you Percy?” and “You’ll be gentle with me, won’t you darling? This is my first time,” the sissy said pleading. Indeed Percy did have a rubber and was very gentle. He even fondled Chrissy’s penis, while Percy’s own genitalia was impaling Chrissy’s hot, baby oiled, tight, little rectum. 

The lovers had nearly simultaneous orgasms, Chrissy nearly gluing himself to the bed with the sissy cream he ejaculated, and Percy filling his prophylactic, to nearly bursting. It took Chrissy quite some time to repair the damage done to his makeup and from here on, he took quite a bit of teasing from his mother, aunt and Sadie about his adoration of his new beau. 

Actually Chrissy and Percy were going to attend the prom as a gay couple with Chrissy in a sissy outfit, but plans changed. It appears that Chrissy had a really heavy duty, hysterical sissy fit one day that took on nearly a nervous breakdown proportion. She had thrown herself all over the floor of the house and kicked and screamed, “I want to be a girl, mother!” 

Aunt Rita had been called in and agreed it was time to let Christina begin to bloom. The occasion that had caused it had been a house-cleaning venture on Chrissy’s part to Sadie’s house. Chrissy had been dressed in a real fruity outfit that left nothing to anyone’s imagination. The clothes, make-up and hair screamed, “Look at me, I’m a real sissy!” 

The sissy had arrived at Sadie’s off campus house that she rented along with her new boyfriend Billy. He was a college ballplayer on a scholarship. The house was a cute two-bedroom cottage. When Chrissy arrived Billy was off with some friends. Sadie nearly burst into laughter at the sissy's attire and appearance. As Chrissy sashayed up the walk to the house, his mother remained parked in front to insure he gave the proper wiggle to his sissified strut. 

His mother had outdone herself! Chrissy wore his heavily jelled hair in a five-inch high French twist! Pinned at the base of the shiny twist was a pert red bow. He had cute curled tendrils at his ears and his bangs were sleek and shiny. 

He wore a bright red, off the shoulder, midriff top, that was heavily ruffled. His white, leather, over the shoulder bag held all his cosmetics, hair spray, body lotion, a hairbrush, and perfume. His jet black, spandex stirrup slacks looked as if they were sprayed on. Sadie could see the effect of the hormones. His butt was cute and plump and his breasts were now past the pubescent point.

The cosmetics he wore were quite heavy and he bore the garish look of a 1940’s silver screen ingenue. His vivid red lipstick matched the polish on his two-inch nail extenders. He was literally hobbled by the 4-inch spike heeled pumps he wore. No housekeeper in her right mind would attempt to clean in that get up!

With the jewelry he really could be heard for some distance away. In addition to the dog-like leather collar with bells all around, “Chrissy the Prissy Sissy Missy” wore jangling charm and slave bracelets all over his wrists, arms and ankles. In addition his triple pierced ears sported one set of two-inch hoops, another set of hot pink triangular shaped, “fashion” ear rings, and a third set of long, faux crystal jewels.

Upon opening the door, Sadie’s breath was nearly taken away by the amount of perfume Chrissy was wearing! Entering the house Chrissy took the heavily ruffled apron Sadie gave him, put it on and curtseyed dramatically, saying, “Ma’amselle Sadie, mother says if I displease you at all, both you and Master Billy should spank me. I have a hairbrush in my purse you may use.” 

“There will be time for that later Prissy Chrissy. For right now, get to work!” Sadie said with firmness.

Chrissy worked his swish butt off. When Billy got home around two in the afternoon, Chrissy was required to curtsey to him and make his lunch. Before serving lunch, Sadie had pinned a lacy maid’s headpiece behind the upswept twist. Billy was quite amused by the swish boy mincing around, flapping his wrists like a little birds wings and looking and smelling so sweetly. 

“So tell me sweet thing are those real boobs?” Billy asked with a chuckle. When Chrissy curtseyed and answered, “Yes sir. They are.” Billy asked, “Well how did you get them, Little Miss Thing?” The sissy gave another curtsey and announced, “ I took pretty pills, and sissy medication sir. Hormone tablets and hormone booster shots.” 

This was about all that Billy could take, but he asked candidly, looking at the sissy’s crotch, “From the looks of things you’ve had your penis removed also. Goodness Sadie, how could you have ever dated this twit?” 

Before Sadie could answer, Chrissy responded, “No sir, I still have my genitals. They are just very tiny from the hormones I take and the gaff mummy makes me wear.” 

Once Billy finished eating, he called Sadie and Chrissy into the living room. Billy began, “Look Sadie, I know you need help with the housekeeping and sweet thing here comes free of charge. All I ask is that you have It, come over here looking less like a drag queen hooker, and a little more like a conventional housekeeper,” Billy said emphatically. 

He continued, “I mean look for yourself. Chrissy could pass for a girl if she tried. I don’t want the neighbors or our friends thinking we have a pansy princess for a housekeeper. I don’t care if pussycat here wears a maid’s uniform; I want anyone who cares to think she’s a girl. Got it?” the young man asked as more of a challenge. 

Both Sadie and Chrissy said they understood. Chrissy remarked that he would have to “Ask mummy.” Then Sadie decided to drive Chrissy home. It was on the way there that Chrissy asked the questions that finally put her over the edge into girlhood. “Sadie, would you ever consider dating me again? Both Ms. Carson and Dr. Cane say that some girls, keep their boyfriends in dresses and date them,” the panty boy asked with a smile. 

“I don’t think so Chrissy. Understand that it has nothing to do with the way you dress or look. You’ll make a really great looking girl. To tell you the truth, I’m sort of bisexual, and have a real weakness for cute, submissive femme girls,” the dominant Sadie smiled. 

“Then why wouldn’t you go back with me?” the sissy quizzed. “Is it because I went out behind your back with that underage girl,” he questioned. 

“No Chrissy, that’s not it. What makes you unattractive to me is that I know you have sex with Percy, and according to him, you love it! I couldn’t possibly date someone who enjoyed having a gay boy put his penis in his mouth and rectum. I’m sorry Chrissy. As a male or female, you are not my type!” the girl said with emphasis. 

Luckily they were very near the Porter residence, because Chrissy began to whimper. By the time they had walked to the door, the sissy was sobbing openly and when Helene Porter asked Chrissy what the problem was, he freaked out, screeching, “Leave me alone! I want to be a girl! I hate being a sissy!” 

Tripping to his room, trying to run in high heels, he threw himself on his canopied bed, and moaned and sobbed as he kicked his legs frantically. After a consultation with Sadie, Helene called her sister, Rita Carson. Rita arrived with nurse Ronda, who gave Chrissy a mild sedative by injection, then placed an ice pack on her head. 

Moving into the living room the four females candidly discussed Christina’s future, Rita Carson summing things up and leading the way. "We should begin giving her girl lessons. Sadie for the time being you should stay out of the picture. Besides ourselves, we’ll enlist Barbara Goodman. She’s done a fantastic job with Pansy, I mean Denise Pierce,” Rita said joyfully. She continued, “Christina should still attend the prom with Percy as her date. However she should be attired as a glamorous female. She should enjoy the entire prom experience; being fitted for her gown, a salon pampering, and of course a tryst with her lover afterwards,” Rita insisted. 

Helene then asked Ronda, “Could you stay here this evening. Possibly comfort her and let her know we will honor her wishes to become a female?” Ronda agreed gladly and at bedtime, Christina, in pink baby doll dress, her hair in pigtails tied with ribbons, was given a dolly called Gigi, and was tucked into bed with Miss Ronda. Ronda turned the sissy on her side and put the sissy’s back to her, making Christina curl up in the fetal position and suck her thumb. 

Miss Ronda snuggled up to Christina and began to cuddle her and rub her back, butt and legs. Christina wriggled, mewled, and sucked on her thumb as Miss Ronda fondled her little sissy stick for her. The orgasm Chrissy had was one of the best she had had in a while, her sissy cream oozing out into Miss Ronda’s handkerchief.

Christina slept like a baby, thinking of her future as a pretty girl. 

                                             Chapter Four: Perms for the Prom 

Denise was doing so well! When she had begun at the salon as Pansy, everyone seemed to predict that she would make a “natural girl.” She wore the sophisticated sissy apparel Aunt Cheryl bought for her with poise, and an air of coolness and assurance. Not too many young men could wear cosmetics in public. 

In Pansy’s case the clothing was equally femme. Bright pastel blouses with lace ruffles at the cuffs, collar and down the front. The fashionably tailored ladies suits were snug at the waistline and in slightly darker colors then the tops. The zip up, high-heeled boots matched the sissy’s suits and his hair was always in a pseudo feminine style such as a French braid or a braided ponytail. 

Often his hair would be rolled up and netted. It was nothing for his aunt to have him escort a boutique customer to the dress shop next door, or send him on an errand dressed this way. It hadn’t taken long for Pansy to realize that he’d get a lot less weird stares as a girl named Denise.

Soon enough Denise was voluntarily getting into dresses around the house and asking her aunt and cousins to call her Denise. She really got dolled up whenever Barb was coming by. She then requested to be allowed to wear dresses outside the house from time to time. “I want to be taken for a girl Aunt Cheryl. I feel I’ll be more accepted as such,” Denise said proudly. 

She was right. Now, the only stares Denise got were the admiring glances one gives a beautifully dressed, immaculately groomed young female. 

With her perfect coiffure and makeup, Denise was a joy to her aunt’s heart. Cheryl was so proud of her she insisted that she become friends with Christina, so that the “new” girl would have a role model that had been where she had been. With the prom, a formal, a few days away, the salon was quite busy. 

Christina had a Saturday morning appointment the day of the formal. Denise was going to help and have her own hair done somewhat simultaneously. The salon was not only that busy, but the ladies felt this type of really girlish interaction would help the two transformed young men bond.

Chrissy entered the salon with her mother, moments after it had opened. Denise had already had her own locks shampooed and conditioned and was waiting patiently for Chrissy, with a towel wrapped turban style around her head. Barbara had been chosen as the one to introduce them as she had helped immeasurably with both girls’ charm lessons. 

“Okay ladies,” she said after the introductions, “I want both of you to be really chatty and girlish. By the time you’re both fully beautified you should be the best of friends. Just like sisters,” she kidded. The girls agreed to do their best as Denise put a salon cape on Christina and took her to the shampoo sink. 

Both sissy girls wore casual loose blouses and skirts. Both had worn very little makeup and had worn their hair down in casual styles that morning. It would be their only concession to comfort for the rest of the day and long into the evening. 

Soon they would both be trussed up in corsets, form fitting formal gowns and elevated to tiptoes by ultra tall spike heels. Their hair would be tightly rolled, permed, teased, sprayed, and put up in elegant hard to hold styles. More then likely they would be twirled around the dance floor by their lovers and shown off. Finally they expected to be taken to some discreet hideaway, dressed in exotic lingerie and are ravaged sexually. 

Possibly the sex act would be spiced up by bondage, discipline or both. Denise shampooed Christina’s hair and chatted about her job and Barbara. Soon Christina loosened up and was raving about her Percy. After her relaxing shampoo and condition, both Chrissy and Denise were seated for their cuttings. 

Aunt Cheryl did Denise’s hair while Lulu Fabu, a cross-dressed sissy stylist, trimmed Chrissy’s. Neither girl got much taken off their shoulder length hair. It was just trimmed, thinned slightly and the split ends removed. Lulu wrapped Denise’s perm and then instructed Denise on rolling up Chrissy. 

“Tightly my dear, very tightly. The best perms are from nice tight wraps and roll ups. Both your hair and Chrissy’s should feel as if it’s ready to come out by the roots” she joked. Both girls were seated at shampoo sinks for the perfunctory application of the highly smelly perm solution. Lulu would apply Chrissy’s perm lotion, and Cheryl would do her niece. 

Pointing to Christina, Lulu said, “Miss Cheryl, I think we should give this one a little mask to wear. Her mother said she’s very dainty and prone to fainting. She just might not be able to handle the smell of the chemicals.” Indeed Chrissy did tear up a little at the eyes but in no time she and Cheryl were underneath whirring dryers reading romance magazines. 

After the sissy girls were termed “done” they had rinses and the neutralizer was added. Then they were taken to the lobby and posed while their female superiors, (mother, aunts, cousins, girlfriend, etc.) took photos. 

Rita Carson especially wanted photos for her office to show new clients what was in store for them. Naturally ladies coming in the salon wanted to know why the girls were being posed like sexy models but had their hair rolled up with rods, papers and smelly neutralizers. 

When told that these were not girls, but sissies getting “punishment perms” the ladies all had a good laugh. However once the perms were combed out and sprayed, the makeup applied, the girls knew it was worth it. Taken next door to the boutique they were fitted for corsets, gowns, and heels. Before being sent home to nap the girls were given hairnets so as not to muss their dos.

At the prom, Denise and Chrissy stood together. Neither could move around very well, and had to be helped around the dance floor by their dates. In addition to the restrictive clothing, shoes, and figure training garments, the dominated sissies had been butt plugged by Mistress Barb and Master Percy so they would be ready for the night’s festivities. 

Chrissy’s mother had even donated her beach cottage and packed lingerie, condoms, and petroleum jelly for her new daughter. Percy had brought the “toys.” Both Chrissy and Denise looked stunning in their ankle length gowns, 5-inch spikes and with their spiral permed hair, done up in very elaborate and elegant, high fashion, curly, up do’s. 

Their makeup was very suitable for eveningwear and may have bordered a touch on the “trollop” side. They danced well for two little trussed up slaves, and by evenings end their dates were quite horny. Percy took Christina to the love nest provided by Helene for the entire weekend and Barbara drove her lover to a condo owned by the surprisingly kinky Dr. Lydia Cane.

Lydia had a multitude of sissy clients, and had on occasion taken one or two to her out of the way condo, for a retreat of sorts. One of the bedrooms was specially designed for the entertainment of sissies and their dominant lovers. Denise was in for a real treat.

                                            Chapter Five: Disciplined Beauties

“Oh Percy, I’ve had such a wonderful evening! Let’s sit out on the porch and watch the waves. Then we’ll snuggle in bed and fall off to sleep in each other’s arms, darling,” Christina said, hoping her lover was a bit tired from the dancing and driving.

“Not a chance dear. We will be here the entire weekend, plenty of time to watch the waves. Tonight I have plans for you, and though they include being in bed, I’m afraid sleeping isn’t in the cards my sweet!” said Percy, taking his girl by the arm and propelling her towards the door.

He sat her suitcase down and let her in the house, returning to the car for his “toys.” As soon as the pair was in the bedroom he began to kiss Christina with a passion. Christina gave in, slithering out of her tight gown, and then lay, face down across her lovers lap, dressed in white lingerie (panties, bra, corset, hose) and matching heels.

Percy enjoyed spanking his sissy girl before lovemaking and Christina was so pumped full of hormones she was compliant to a fault. The boy enjoyed using a paddle he’d had Chrissy buy at a specialty shop. It was fur covered and Chrissy had picked it out herself.

Chrissy’s mother had made sure that Percy knew her daughter was his for the entire weekend. The closets were full of specialty apparel for the sissy, maids’ uniforms, and swimsuits being in good supply. Percy would make good use of his sissy girl’s submissive talents. To begin the weekend with a good paddling would certainly set the tone!

The swat’s fell rhythmically upon Christina’s well-rounded bottom. She shrieked and sobbed, frantically kicking her slender, tanned legs. She counted them, as required, saying after each number, “Thank you so much, Sir Percy!”

Soon though, her hysterical sobs prevented her from doing any counting or thanking, and she begged submissively, “Please Percy darling! Take me! Take your dear Christina? Please darling! Make me your whore?”

Percy was more then glad to acquiesce, picking up the helpless sissy in his arms and depositing her on the bed. Once he had stripped naked, he stood by the bed, his hard on raging. “Kneel my dear. The bed is quite soft. You can be very comfortable while I stand here and you suck me,” the gay young man smiled.

“Oh yes darling! Let your Chrissy-Poops suck her lollipop,” the femme sissy lisped, using baby talk. Of course, by now Christina was an expert at sucking her Percy-Poops off. She licked his balls and slurped and slobbered all over his huge, purple-ended cock. Percy was in ecstasy and decided he needed a little more.

“Take out your plug my sweet sissy girl. Daddy Percy wants to enter his baby girl’s poop shoot,” Percy giggled. Christina did as she was told. Always! Now on her knees again, facing the headboard she gasped as Percy lubricated her love hole with petroleum jelly, applied with a gloved hand. Percy then oiled up his condom-covered shaft. Slowly and gently as he always did, he began to enter his sissy love’s rear end, as she thrust back towards him, her eyes filling with tears of passion.

“Oh my! Oh Percy! You seem so big tonight!” the sissy said as she began to thrust harder and pant, as the heavily sprayed spiral curls atop her head began to come loose and bounce about her face due to all the action. “Percy play with my sissy plums and sissy stick dear!” she begged, as her boyfriend’s well greased hands surrounded her hormonally shrunken pubes.

As Percy plowed into his sissy love she bucked like a hot little filly being pounded by a stallion. The orgasm they both had culminated in Percy exploding into his sturdy condom and Christina screeching and twisting herself into the bed.

The rest of the weekend was spent with Christina in either full maid’s apparel, or swimsuit and heels waiting on her lover hand and foot. At night she’d put on her most sexy lingerie. Then, standing in front of Percy, her legs tightly together, her index finger in her pouted lips, her eye’s downcast, and she’d demurely say in a childlike voice, “Prissy Chrissy was such a naughty sissy poops today. Should she get her hairbrush and get over daddy’s knee?”

Of course Percy would frown and say, “Yes darling. That would be a good idea. Run along and find your brush. That’s a good girl!

For Denise, the evening was shaping up just fine. She was very impressed with Dr. Lydia’s condo. However when she found Dr. Lydia there with Fifi, Dr. Lydia’s sissy maid, she knew that something interesting was up. After modeling for them, Denise was told by Mistress Barbara to undress down to her pink satin lingerie and heels.

“Proceed to the large bedroom to your left and stand in front of the mirror sweetheart,” Barbara said condescendingly. As always the submissive Denise did as she was told. Lydia, Fifi, and Barbara entered the room behind her and Barbara had the blushing Fifi remove Denise’s bra. Then Denise was made to hold her arms and hands high overhead while Lydia and Barb fastened her wrists to a set of manacles attached to the ceiling.

“Come along Fifi. Our work here is complete. As much as I’d love to watch, I will respect Mistress Barbara’s privacy. We’ll leave these lovebirds alone now,” said Lydia Cane, to her sissy maid, as Lydia smacked Denise on the butt and winked at Barb.

The smack got a squeal from Denise so Lydia added, “Goodness Babs, she enjoyed it! You’re not even getting started yet!” Indeed they had hardly begun as Babs, riding crop in hand began to casually circle around her helpless, bound slave, tapping the crop in the palm of her hand and saying, to no one in particular, “Now let’s see. Where do we want to start?”

“I imagine I should begin by undressing,” Barbara said as she began to remove her elegant, fashionably tailored tuxedo. Once down to her red satin lingerie, she put on a white kimono and took down her wavy, jet-black hair, which had been up in a chignon. She shook it loose, so that it fell to her shoulders. Opening the kimono and tying it back, she took off he panties to show off her shaven pubic region.

 She made a few trips to the bathroom, and returned with scissors, razor, battery powered clippers, shaving soap, tweezers, a bowl of water, powder, lotion, perfume, and a towel. Placing everything on the bed stand and dresser, she began to tell her slave about an English Mistress named Mrs. Silk.

“She really is amazing dear! I just ordered quite a bit from her latest catalogue. Mrs. Silk is a premier authority on sissies worldwide!” Barb added as she examined her slave’s pubes. “I just love her manuals. By the by dear, you will read and memorize the sissy manual. I purchased some lovely apparel for you and some interesting accessories. We’ll be trying out the accessories this evening,” Babs added as she went to the dresser to get her “good scissors.”

“One thing she recommends is that a sissy have a shaved powdered and perfumed pussy area. We’ll take care of that now and follow it up with some interesting entertainment. You will also keep your sissy pussy area the way I leave it this evening, or else!” Mistress Babs informed her sissy as she began to trim the hair off in clumps.

Once the hair had been snipped, she gave her sissy a buzz cut with clippers before using a pink, girl’s razor to shave the sissy’s genital area smooth.  Before scenting the now smooth region, she plucked a few “stray hairs”, using the tweezers, and elicited amusing squeals from her helpless sissy girl.  She followed this with a lotion conditioning, a heavy application of powder and a scenting with perfume. The sissy became quite erect and Barb began to enjoy herself.

Sucking on the sissy’s swollen nipples she began to rub her vagina on Denise’s pole. When Barb felt lubricated enough, she picked up a hairbrush and pulled her sissy to her, impaling herself on Denise’s swollen sissy clitoris. With her left arm around the restrained sissy’s back, she used her free right hand to swat Denise’s butt with a hairbrush, exhorting her, “Pump, bump and grind baby! Don’t dare come! I plan on a Mrs. Silk style milking for you tonight honey.”

Denise did as told and Barbara had her way. As Barbara neared fulfillment, she dropped the brush and lifted her dainty swish up by her well-shaped legs, placing the legs around her own lovely waist. “Wrap those gams around mummy, sweetheart! Squeeze tight! Let’s ride baby!!” she encouraged the frightened sissy. Denise was still fastened to the ceiling manacles and had no idea Babs was strong enough to lift her helpless body up like that!

Babs came in waves and rocked her sissy very hard. While Denise stayed rock hard and hanging motionless, Babs sucked all over her body before resting for a while on the bed. “Come along sissy! To the living room!” Babs shouted as she fashioned a collar and leash on Denise and untied her hands.

To Denise’s surprise, upon entering the living room, she saw that Lydia Cane and Fifi were still present! They had been joined by Aunt Cheryl, Ms. Carson, Cousins Ronda and Sharon, as well as future mother-in-law Tina Goodman! They all clapped as Denise was led to the center of the room for a modified version of a “Silky Milking Ceremony.” The first order of business was to dress Denise in a pink, plastic “Milking Pinafore” and matching “Milking Bracelet” complete with obligatory bells, sent by Mrs. Silk’s mail order service.

Once that was completed Fifi assisted her to a stage-like, pedestal area. Fifi put on her own milking bracelet, with glove, and then set a table with, lotion, a champagne glass, and a seven bottles of perfume with bulb atomizers. Candles and fragrant incense were lit, music started, and the lights turned down as Fifi began to serve wine to all the ladies.

Denise was quite scared, so her Mistress calmed her by saying, “Close your eyes angel, let down your hair and touch yourself. Sway gently with the music. We all know you need to be milked honey and we are going to let you do it yourself.” Just then a spotlight lit over Denise and she was enveloped in a beam of pink light!

As she began to milk herself, eyes closed, the ladies chatted. Denise could barely hear them over the ritualistic music playing on the stereo system. Barb had chosen it and the group was called, “Valerie Van Isis and the Lady Slippers.” They were an all female group, predominantly lesbian with a couple of bisexuals.

They used a mixture of kettledrums, bells, chimes, and various stringed instruments, (dulcimer, mandolin, harp) to create a lovely blend of rhythmic minstrelsy. Along with their harmonious vocals, this produced some really wonderful melodies. Dulcet tunes such as “I Love You Girlfriend,” “Woman to Woman Passion,” “Sexy Sisters,” and “Feminine Peace” floated through the air.

As the songs played, the ladies got up, one at a time and approached the very aroused sissy. Each woman, in turn, picked up a different perfume atomizer and sprayed the now dancing and swaying sissy from head to toe. The scents used were lavender, arnica, patchouli, sandalwood, honeysuckle, and lilac. Mistress Barb used her favorite perfume, Shalimar, to put her own touch on her personal sissy.

Each lady announced, “I anoint this sissy with this lovely scent and implore the Goddess Isis to put this sissy at peace with her new found girlishness!” Everything seemed to add up to get Denise very close to climax! The cloud of perfume surrounding her! The music. The utter helplessness of her plight! She whined slightly as she was having a little trouble coming.

At a pre-arranged signal from Barbara, Fifi, moved a chair to the right of Denise, and then knelt on the pedestal to Denise’s left. Holding a pink tinted crystal champagne glass in one hand, Fifi used the fingertips of her gloved hand to begin applying a creamy lotion to the head of Denise’s penis. Denise gasped, then looked down and smiled and winked at her new sissy sister.

Denise mouthed the words, “Thank You,” as Fifi puckered her lips and blew Denise a kiss. Just then a smiling Lydia leaned over and whispered to Barb, “This is perfect. We’ll get all the emotion drained from her this weekend. Sunday night she’ll be as limp as a dishrag and demure as a daisy for her ladies club debut. The girls will adore her,” she said to the proud Mistress Barbara.

Denise could take no more. Gasping and panting, the bells on her bracelet and Fife’s tinkling rapidly, she took a huge breath and screeched, “Mistress Babs! Mistress Babs! Oh my! I’m coming Mistress Babs!! Oh no! I’m coming!! Come she did, as Fifi caught every last drop in the champagne glass!

Good thing too. Lydia hated sissy cream being spurted on her tiled floor, though it was easy for the sissy to lick up. No rug hairs in the teeth either! Lydia was thoughtful that way. Of course Denise had to be helped into a chair and Fifi used a warm washcloth to clean her sissy clitoris off.

Then a toast was drunk to Isis, and Mrs. Silk. It wasn’t until all the ladies had kissed Denise on the forehead, that she realized the glass she had drank her “Shirley Temple” from, (the ladies drank champagne) had been the same one she had spurted into. The ginger ale had masked the salty taste.

Denise spent the entire weekend in the same way Christina did, waiting on her Mistress and wearing whatever outfit she was told to wear. Monday afternoon, her hair was shampooed, set and then dried. After drying it was done in little girlish banana curls.

After a corset was put on her, she wore a training bra for the last time. Adding a full slip and bouffant crinoline petticoats, “Little Denise” was given a lovely confection of yellow chiffon, a party dress that would make any mummy of a ten year old really proud! A lovely white sun hat was placed on her ribbon tied curls. Some ankle socks and white patent leather Mary Jane’s with adult, two-inch heels and she was ready for her debut.

The makeup was a little heavy, but then again everyone at the “Silky Ladies Club” (named in honor of Mrs. Silk) knew she wasn’t really a little girl. Denise was taken backstage, put on yet another pedestal and told to lower her eyes demurely and fold her little hands in front of her, placing her white patent leather purse over her right wrist.

The curtain opened to the strains of “Thank Heaven for Little Girls” and the ladies in the audience cooed and clapped at the sight of Rita Carson’s latest conquest. A yellow tinted spotlight highlighted the newest little star! Mistress Barb went to the stage and along with all the other ladies involved in the transformation, gave a narrated slide show, which everyone including Denise got to watch.

Every detail of her transformation beginning with her trip to the girl’s center as Pansy, to her “Milking Ceremony” at the condo, were shown. At the end of the show, Barbara led her sissy around the club to the applause of the members and she introduced her to each lady present. Then a nice dinner was served by well-groomed sissy maids, with Denise in a high chair, being fed, in turn, by each of her mentors. The event had begun at four P.M. and at the babyish hour of seven-thirty “Mummy Babs” and “Little Christine” left.

The party went on until ten P.M., and the sissy staff of the club performed the cleaning up. Denise snuggled up to Babs that evening and fell off to a peaceful secure sleep. She awoke in the morning wondering when Mistress Babs would take her in marriage. She’d have to wait a few years but the day did come.


Her conditioned hair up in a towel, Denise answered the door. Wonderful! It was Christina with her Mistress, Sadie! Denise let them in and Sadie hung Christina’s uniform in the closet, kissed her sissy goodbye and told both the girls to, “Have things ready by seven P.M.” Off she went to meet Barbara for some shopping.

The girls would be serving at a dinner party for ten, that their Mistresses were throwing for some lady friends. Both girls were quite excited. Denise had recently been wed to Barbara, an investment banker. After Percy had dumped Chrissy ("You’re too much like a girl,” Percy had said) Chrissy had started classes at a secretarial school, where Sadie, who worked with Barb, had recruited her.

Then Billy King had dumped Sadie, when he got a big contract with a Japanese baseball team. Sadie and Chrissy had begun to do everything together, even getting their hair done at the salon where Denise worked. One afternoon Christina went brassy blonde and Sadie was in love. All she needed to know was whether Percy and Chrissy had been “safe” and that Chrissy was being tested out negative.

“Yes to both dear,” said the new blonde, “Give me another chance and I’ll be your slave for life, Mistress,” added the kneeling sissy.

“You can bet your sore little ass on that!” said the aptly named Sadie, pulling the little sissy to the bedroom, holding her by the wrist. “I think we should cement this with a spanking, don’t you Christina?” asked the quizzical Sadie.

Christina didn’t hesitate! Putting her finger to her lips and bowing her head she said, “Yes mummy Sadie. I’ve been such a bad little girl lately!”

                                                              The End? * 

* Authors Note:

I would really be interested in doing a sequel to one or more of my stories. To any readers who have read any of them: If you have a favorite story of mine, which you’d like to see a sequel to, please email me at: prissy87@hotmail.com  I have an idea for my next story “Stable Girls” but I’m looking down the road. I’ll wait a few months to see what the response is to this request. Thanks, Prissy Bouffant.


Sissy Girl Stories