(Updated) Sorority Sissy: Part 1

Priscilla Bouffant

Priscilla's email:
priscillagaybouffant@gmail.com

Portia Duvall has an unusual request from a client, concerning the client’s Nephew. A Grad student like her could use the extra cash. 

Chapter I: Andrea’s salon

     Andrea Carson looked over at the nervous teen seated in the waiting area of her plush new salon. He’d been led in by her Grad Student friend, Portia Duvall. Portia was tutoring the 17 year old male as a way of making some extra funds as she completed grad school.

    Andrea had recently opened, the “Sophisticated Lady.” With her reputation for hair, wigs and makeup on Broadway, preceding her, she had a ready clientele. As someone who had also worked with Female Impersonators, she had let it be known she was willing to work with women that might have a sissy or two they wanted to transform.

   Andrea motioned to Portia to come to her private office. “We’re did you find Little Miss Sweet Thing? I can’t wait to get him onto a makeup stool,” Andrea chimed.

     “I am tutoring him in Math and English, at the request of his aunt. He’s 17. He’s in his last year in High School. He does well while I’m tutoring. Then he proceeds to become an amazing screw up at school. His aunt is Ariel MacAfee, the commercial real estate broker, so she pays really well,” Portia explained.

     “She asked me if I thought occasional petti-coating, evenings, weekends and holidays from school might help. You know, calm him down and keep him away from bad influences. I told her I knew someone that could likely help,” Portia continued.

    “Seventeen? Aren’t you the cradle robber?” Andrea laughed.

     “Andrea, I’m 22. Barely 5 years older. His aunt is footing the bill for everything and doubling my salary.
Those are her college age daughter’s two inch heels and Capri slacks he’s wearing along with that Peter Pan blouse. Her daughter Jocelyn outgrew them. She’s a little big boned but a real looker,” Phyllis grinned.

     “Cute. He’s more petite than his older cousin? He will make a lovely female you know?” Andrea smiled.

     “He isn’t really a ‘Pixie’ petite. He’s 5’8”. He’s just slender. You know, with the right diet and training,
he could have a sexy, svelte, shape to him,” Portia added.

     “How did you get him into those clothes and into my shop?” Andrea asked.

     “He’s on restriction right now. If he wants to get off sooner, rather than later, this was the consequence his aunt gave him. Plus, I’m taking him to a costume party at my old college sorority. He really didn’t have much choice,” Porsche explained.

     “Can you take him off my hands, Andrea? I have a class. Then I want to get ready for the party. Can I pick him up in a few hours?” Portia asked.

     “Sure. Once I doll him up, I’ll have him play with makeup and introduce him around the salon. Really immerse him in my lovely inner sanctum of femininity,” Andrea teased.

     “Thanks. His name is Nicholas, but his aunt and I have persisted in calling him Nicky,” Portia explained.

       “When you return he will be well on his way to becoming your Nikki/Nicolette,” Andrea laughed.

       As Portia left the salon, Andrea snapped her fingers and called out. “Nicky? Come with me please?
This way dear,” she said as she propelled the spellbound boy into the salon proper.

     Nicky tried to relax as his hair was shampooed and conditioned, but tensed up as Miss Andrea mixed a hair color. He had a dusky blond, lanky hairstyle but it wouldn’t be like that for long. From the start, Andrea had insisted he call her, “Miss Andrea”.

     Once she had brushed on the new hair color Andrea seated him under a dryer. Then she rubbed in a leave on conditioner before she trimmed his hair and set it, tightly on medium sized rollers. Nicky could tell the new hair color had a red tint to it. He just didn’t know how red.

     He had also never worn rollers, and was becoming really embarrassed by his situation. Andrea, had been firm with the boy, throughout the beautification process, though she had been sensual in touching and brushing against him.

     With his hair in rollers and Nicky wearing a pink satiny cape, Andrea had him stand and showed him how to pose erectly, hold his hands out and take smaller steps in heels.

     “You don’t want to look like a boy dressing as a girl. If you minimize the size of the steps you take and use your hands and arms for balance you’ll appear girlish and people won’t stare at you. You modulate your voice well. It’s almost sweet. Smile more when you talk though,” Andrea admonished.

     “We’re going to let your hair dry and set naturally while we do your makeup. Come with me, honey. I’ll help you mount this makeup stool,” Andrea added.

     This was the favorite portion of any sissy makeover for Andrea. Were Nicky a female model, or any real woman, Andrea would have him relax in a reclined salon chair while she worked her magic with his makeup. But never would she do that with a sissy, especially a novice sissy, like Nicky.

     Instead, as she showed “Nikki” how to walk prettily to the makeup stool, she placed her arm around his waist. “That’s it honey. You walk pretty. Okay, let’s help you mount the stool. Up we go baby,” Andrea said, as she assisted him by practically lifting him up on the elevated stool.

     Nikki acted surprised at the stool’s height. His feet were well off the floor. Andrea showed him how to place his heels on the minimal footrest. Then she encouraged him to sit up straight and place the small of his back against the slightly elevated back rest.

     “Hands in your lap doll face. You are a very pretty boy Nikki and I’m going to make you lovely. Look in the mirror at yourself,” Andrea encouraged.

      Nikki felt silly, but when Andrea looked deeply into his eyes and said, “Relax. You will be so lovely when I’m done, no one will know you are a boy being dressed as a female, as a consequence for bad behavior. If I were to put a padded bra on you everyone would believe you were a sexy 18 year old girl,” Andrea announced.

     Andrea worked carefully, blending pinks and reds on his cheeks, lips and eyelids. She thinned his brows and curled his eyelashes. She then lowered the stool slightly and began plucking the rollers from his still slightly damp hair.

    Using hair spray, a brush, teasing comb, curling iron and a dab of sculpting lotion, she fashioned Nikki’s collar length, coppery-red locks into a tonsorial masterpiece. He looked at himself stunned. He had what was close to “big” hair, but not quite.

    But he now sported a definite cloud of sassy, bright, titian, curls and waves, blended in with his softer coral shaded cosmetics. Andrea took his hand and helped him off the stool. “Come with me honey and meet some of the people that work at my salon. Maybe you’d like to work here one day?” Andrea smiled.

     “Please no, Miss Andrea. I look so female!” Nikki gulped, close to tears.

      “Nikki. You stop that! You look great, and you are supposed to look very feminine. It is a costume party. And don’t start crying, please. If you ruin your makeup, well, I would not take kindly to that,” Andrea glared.
        “Well, don’t you look hot Nikki? The girls at the sorority won’t be able to keep their hands off you. And wait until Auntie Ariel gets a look at you,” said Portia, to everyone’s surprise.

Portia looked very dominant and truly gorgeous in full makeup, red leather, skin tight slacks and matching high heeled boots. In the spike heeled boots, with her hair in a dramatic upsweep, she appeared to tower over Nikki with good effect.

        “Allright Nikki. Come along with me. We’re going to visit with Auntie Ariel before we go to the party,” Portia said as she took the boy by the hand and accompanied him to the cashier.

      Portia handed Andrea an envelope. “Ariel hopes this cover everything.”

       “Indeed it will. Here is a nice gift bag of cosmetics and hair care products for my new client, Nikki. Nikki, maybe we can get you back in here for a permanent wave and an ear piercing?” Andrea smiled.

     The new sissy boy shivered with fright as Portia led him to her nicely appointed Acura SUV. It was a graduation gift from her mother, Martine. She held the door for him to get in. “Watch your hair darling. It looks great and we want to keep it that way,” Portia smiled.

    On the ride over to Nikki’s aunt’s home, Portia explained a little about her former college sorority. “We are a group of very assertive women, who believe that the female of the species needs to affirm herself more strongly in the business and financial world as well as the home front,” Portia began.

   “We feel, that if that would mean our male ‘partner’ needs to take a back seat to us in a relationship, and perform the traditional, submissive female role, so to speak, then that is all the better to advance our careers,” she added.

     “Your Aunt Ariel was a member of the same sorority, and my mother was, as well. Don’t worry honey, you won’t stand out this evening. There will be enough young males, dressed like you are, and many will be attired even more effeminately. That is just the way we Cassandra ladies do things,” Portia revealed.
     “Cassandra ladies?” Nikki asked.

     “Yes dear. My college society as well as your Aunt’s, and my mother’s was named the Cassandra Sisterhood. We’re very close and supportive of one another,” Porsche explained.

Chapter II: Ariel and the Sisters

     Ariel MacAfee eagerly awaited the appearance of her errant nephew, now safely in the clutches of her protégée, Portia Duvall. She hoped soon she could interest her own daughter Jocelyn in a more active role in both the Cassandra group as well as Nikki’s feminization.

     Portia knocked lightly and entered Ariel’s home immediately after, with Nikki in tow. Nikki had his new bag of makeup and hair care products in his free hand. Portia took the bag from him and propelled him towards his aunt.

     Nikki stopped a few feet from his aunt. “Stand erect. Arms at your side, wrists extended. Just as Andrea showed you at the salon Nikki,” Portia ordered.

     Ariel smiled and circled her nephew, as a cougar, eyeing her prey. “Lovely, oh so lovely Nikki. Portia, I adore it! Andrea did an excellent job. Nikki, you will sleep in a hairnet this evening. We’ll show you in the morning how to give your stylization a nice ‘lift’ to make it look nice and full after an evening of beauty rest,” his aunt instructed.

      “Portia, I have to ask you a favor. Tomorrow is Saturday and because of a surprise visit by a top buyer, I will have to be at the office much of the day. Would you be able to spend the evening, and stay until tomorrow afternoon, to supervise Nikki and keep him out of trouble? I will make it worth your while,” Ariel promised.

     “Of course, Ariel. I keep a bag packed in the rear of my SUV, just for such overnight stays,” Portia promised.

     “Come along Nikki, time to meet some of my sisters,” Portia added.

     “Nikki. You will behave for Miss Portia. You well know that you’ll taste my paddle or hairbrush if you don’t. In fact, I just might allow Miss Portia to discipline you appropriately,” Ariel warned.

    This was quite humiliating for Nikki. He had tasted his aunt’s paddling on numerous occasions, but for her to announce it in front of Miss Porsche was so distressing. What worried him more though, was that the threat of a spanking from Miss Portia had aroused him.

    Arriving at the Cassandra house, Nikki realized his escort for the evening was quite well liked by her “Sisters”. The ladies of Cassandra surrounded Portia. Though most hugged her, a few, like Michelle, the newly elected Cassandra president, kissed her full on the mouth.

     Portia reciprocated eagerly. “Oh Michelle you minx! You look and smell lovely this evening my gorgeous sister,” Portia smiled.

     “Who, pray tell is this pretty little Miss Thing, Portia?” Michelle asked.

      “This is Nikki. One of my tutoring students. Nikki, greet Miss Michelle appropriately,” Portia ordered.
       Nikki told Miss Michelle how pleased he was to meet her.

      “I see you haven’t taught him to curtsey. Can he serve refreshments yet?” Michele chimed.
     “All in due time my dear, all in due time. I’m certain he could walk around with a tray of hors dourves, without causing too big of an accident,” Portia chimed.

      “Good enough. Nikki, do you see the raven haired beauty, in the maid’s uniform with a curly perm? That’s my boyfriend Annabelle.  Let him know, Ms. Michelle said, to teach you how to hold and present a serving tray of chilled shellfish. Now run along,” Michelle ordered.

       Nikki served for an hour before being excused. He immediately minced his way carefully over to Portia’s side and instantly clasped her hand. Portia turned to him and winked sexily as she squeezed his hand tightly.

       “What a strange party,” thought Nikki.”  All the boys were wearing dresses and the women were wearing the more masculine cut clothing such as slacks and ladies suits. In fact Nikki was one of only two boys not wearing some sort of frilly feminine concoction.

       One other male, standing close by the sorority House Mother, was wearing a pink Chanel, “ladies who lunch” pant suit.

        Just after midnight, Portia leaned over and whispered into Nikki’s ear. “We should be going, love. I need to assist you with dressing for bed and some other things.”

        On the trip home Nikki tried to explain to Porsche that he was well enough equipped to put himself to bed. Portia silenced him immediately, by intoning, “Nikki. Your aunt pays me to both tutor you and supervise you. You will listen to me. Now once again, I will be dressing and preparing you for bed! I want not another word from you child.”

       Ariel was already in her bedroom reading when the couple returned from the sorority party. She had carefully laid out a pair of ruffled panties as well as a multi-tiered, thigh length nightie for Nikki to wear. She had also set out all his cosmetics, face creams and hair care products on a new vanity she’d placed in his bedroom.

     Over the past weeks, his boudoir had become more and more femininely appointed, including the 4 poster, canopied queen bed. He’d already been hairbrush spanked twice for complaining about the new décor, so now he dare not say a word.

     Last but not least, Ariel had laid out on the bed, with the panty and nightie, her birch, Cassandra Society sorority, discipline paddle. As both Nikki and Portia entered the sissy’s bedroom, they both saw the paddle immediately. Portia picked the paddle up.

     She inspected it carefully, smiling at the carefully painted, Black Rose, embedded on the paddle. The Black Rose, being the emblem of the Cassandra Sisterhood. Next to the paddle was a handwritten, signed note.

     “Portia. You may use this, my personal paddle, should Nikki displease you in any way. Ariel,” Portia read aloud. “I don’t think we need to worry about this, do we Nikki?” Portia asked.

      Nikki, shivered, and shook his head. “No ma’am, Miss Portia. I’ll behave for you,” the boy smiled meekly. From there on it was a ‘piece of cake’ for Portia. She had the boy undress, and slip into the panty and nightie set. She did the same, taking a shimmery set, of black sateen pajamas from her overnight case.
 
Then she bade the boy be seated at the vanity with her, while she carefully removed her own makeup, then his, describing every detail, including the nightly application of facial cream. Then she unpinned her elaborate upsweep, before sexily shaking loose her cascade of auburn curls.

    Then she covered Nikki’s hair with a hairnet, before picking up a tube of coral pink lipstick and carefully applying it to her own lips. As she did so, the boy stared, mesmerized by her precise, detailed, actions. Then she turned as she pursed her own lips and stared into the nearly hypnotized sissy’s eyes.

    “Your bed is large enough for both of us to sleep in. Just in case, I decide to kiss you goodnight, I want you to be wearing creamy lipstick like mine. You would like me to kiss you goodnight, wouldn’t you Nikki?” Portia asked.

     The teen aged boy could barely speak. He took a deep breath and gulped. He thought he would faint. “Oh yes please Miss Portia. I would love that,” he whispered, almost girlishly.

      “I thought you would Angel. Hold still while I give you a nice, pretty set, of girlish lips,” Portia said, as she lovingly applied a full coat of pink lipstick to the boy’s mouth.  Portia stood, took the boy by the hand and led him to the bed.

      “Come with me honey. Come to bed with Miss Portia,” she intoned.

      She turned the covers down and helped the feminized boy into bed. Then she gracefully slid under the covers on the other side. She pulled the boy into her body and snuggled, covering his face with kisses and intoning, “Oh my pretty girly boy Nikki. You look and smell so nice tonight. Let me kiss you,” she added.
   
 She kissed the prettified sissy boy full on the mouth and inserted her tongue deeply. When both she and the sissy boy finally came up for air, he gasped. She asked him, “Wasn’t that nice? The taste of our lipsticks mingling? Come here girl. Let me touch your clit,” she laughed.

     She grabbed the excited boy’s penis and squeezed. It had swelled and hardened very nicely. She lubricated his penis, imploring him not to come until he was given permission. When he was fully erect, she stopped manipulating him.

     “Before you get to squirt, you will please me first. Get your head between my legs and I’ll instruct you on what to do girl,” Portia ordered.

      Indeed, she instructed the sissy boy on exactly what to do, whenever he was in a sexual situation with a female. Though a novice, Nikki learned fast and Portia was soon squirming with delight. As her dam burst and she started to shudder to a climax, she held the sissy tightly by the shoulders.

     “Don’t you dare stop, you little whore! Eat me! That’s it!” Portia exclaimed as she dug her feet into the sides of the sissy boy. Nikki, licked, sucked and fingered Portia’s clit for all he was worth and too good results.

     Portia had an exhausting orgasm. She pulled the sissy up close to her and had him rub and kiss her abdomen. Then she flipped the still erect young man onto his back. “My pussy is nice and juicy now. Perfect for mounting your cock,” she laughed.

     For Nikki, this was a new experience. He’d never been with a real woman. Portia moved up and down, expertly on the boy’s swollen penis. She taunted him by teasing, “If you spurt, even a little bit, before I give you permission, you’ll get a public spanking in front of your Aunt Ariel at breakfast.”

     Of course she knew, a possible virgin, like Nikki could never hold out too long. “Okay sweet Nikki,
Mistress gives you permission to orgasm,” she laughed, as the boy spurted and bucked, gasping as he spent his passion.

      Nikki, started sobbing lightly, while Portia covered his face with kisses. “Don’t worry my sweet girly-boy. There will be so much more fun for both of us, as long as you behave,” Portia promised.

Chapter III: A Winthrop Girl

     The Cassandra Sisterhood, had a network of schools where sissies were trained for their appropriate positions in the Sisterhood’s society. Ariel, Portia, and Portia’s mother, Martine, eventually wanted Nikki to attend a branch of the Winthrop Institute within a two hour drive of their residences.

     The school was called “Winthrop at Greenbrier.” All of the Winthrop Girly-Boy academies had similar designations. Of course, the name Winthrop, was taken from Cassandra Winthrop, the founder of the Sisterhood.

     The opportunity to enroll Nikki at Winthrop, came just before the Holiday season. Nikki had been under a strict ritual of dressing effeminately, every day after school, weekend and days where school was closed.
     His mannerisms were now more feminine and he had a difficult time not acting girlish when he was in school. The males at school shunned him, even his former friends. However, he seemed to become more popular with the females.

     Soon enough the boys at school started to bully him verbally. Mostly calling him names. He let his aunt and Portia know about it. “Well, I could go down to the school and report it. Or, as you are 17, I could legally withdraw you from school and home school you,” his aunt replied.

     “Lastly, we could enroll you in a private boarding school to get you away from all of these horrid influences,” his aunt intoned.

       During this discussion, Portia was seated next to Nikki, on a love seat, playing with his hair and leaning against him with her breasts. She whispered in his ear, and kissed his cheek, saying, “I think the boarding school is the best idea lovey.”

      Nikki balked though when he looked at the brochure from the Winthrop Institute. It was a Sissy girl’s school! It took quite a bit of coercion from Portia and Ariel to convince him to try it out for just two terms.

     “One term is 3 months. The entire program, if you do well is only a full year. You will have your diploma and be able to go to any University you want, after graduating from an impressive school such as Winthrop,” Portia bargained.

     “Can the girly dress up games stop then?” Nikki asked.

      “Of course darling. If you want to stop the dressing as a girl by then, that would be up to you,” Portia smiled.
     Nikki agreed. He was about to become a Winthrop Girl. His Mistress, Portia Duvall was quite happy about it. Besides business connections, and loyalty to the Sisterhood, having your own, exquisitely trained, effeminately appointed, Winthrop Sissy, was another way to gain prestige in the Sisterhood.

     Nikki arrived at the gates of “Winthrop at Greenbrier” for the spring term. He wasn’t quite ready for the intensity of the program he was entering. Nor was he well prepared for the strictness of the instructors.

    He realized it the first day, during corset training. At 5’8” and 137 pounds he already had a girlish 26” waist. When he protested, albeit mildly to the Wardrobe Mistress, he received a slap in the face.

    Followed by the admonishment, “Darling, you are a Winthrop Girl, with a waist that can easily be slimmed to 22 inches, but maybe in your case we’ll try for 20? Tie this sissy girl tightly to that lacing bar. Go for about a 3 inch reduction. Then leave her up so I can paddle her” the mistress ordered.

    Nikki was scared, and well should be. The two assistant mistresses pulled tightly on the laces of the corset. One of the two ladies went so far as to put her bare foot in the small of his back to get a little extra into the tightening of the laces.

    “She’s a pert and prim 23 inches, Wardrobe Mistress. Do you want us to plug her butt, before or after you paddle her?” One of the ladies asked.

     “After! I don’t want the plug going too far up her rectum,” the mistress laughed. Nikki was given six of the hardest swats with a paddle he had ever been given. He was squealing girlishly by the time the paddling was over with.

     “Put some cold cream on her pink little butt and get her lubricated and plugged. Sissy! Sissy Nicolette? What’s the highest heel you have worn?” The Mistress asked.
     “Three inches ma’am,” Nicolette blubbered.

     “Put her in a 4 inch heel. I love watching them mince around with the plug up their ass, a nice tight corset squeezing their waist, and super high heels on their feet,” the wardrobe mistress laughed.

     The two assistants came up behind Nicolette and slathered some cold cream over the pinkish area where he’d been paddled. Then, the taller of the two ladies, put on a surgical glove and inserted two lubricated fingers up Nicolette’s rectum.

     “Just go with the flow Nicolette. You can help me out by wiggling a little bit and not being so tense,” the woman teased.

     “What are you doing ma’am? Why are you calling me Nicolette? My name is Nikki?” The sissy begged.
     Nicolette screeched as the women pinched her ass. “Your name is no longer Nikki. It is Nicolette. That is the name your Mistress assigned you when she enrolled you here,” the mistress informed.

    “To answer your other question, sissy, we are inserting the smallest size butt plug we have, so you will walk, very, very prettily, about the school grounds, and entertain us. But, if you persist in complaining we can start with a larger size?” The Mistress said.

     Just then, Nicolette gasped, and the Mistress said, “There! We’re done,” as the butt plug was fully inserted. Both ladies then fitted Nicolette with a pair of silky slip up hose, and 4 inch high heels. The heels did mercifully take Nicolette off her tip toes.

     Lowering the lacing bar took pressure off of Nicolette’s arms and shoulders, but when released from the lacing bar she noted the intense pressure from the corset, butt plug and heels, being centered from her ankles to her breasts.

     Yes, breasts. The corset had helped form a little set of bumps. Nicolette’s first breasts. After being fitted with a padded bra, a pink, preppy, schoolgirl shift was lowered over Nicolette’s curler, covered head.

     The shift had a nice pink bow that draped from her collar to her midsection. She was wearing the uniform of a first term novice sissy. Nicolette was made to sit at a vanity and apply her makeup, remove her curlers and spray and style her own hair.

     “That will do for now. You will be getting plenty of practice in beauty classes. We have other new girls to get ready. Go stand in that line and wait until it is your turn to see your academic counselor,” Nicolette was told.

     Nicolette found it difficult walking with the extra one inch of heel. She noticed her steps were extra tiny and precise. She also noted her butt wiggled back and forth. Several of the instructors checked her out and chuckled.

      When Nicolette was called into her academic counselor’s office, she curtsied as she had been shown to do by Portia and Ariel. Ms. Carlson, the counselor bade her to sit down and began going over her courses.

      The first surprise came, when Ms. Carlson referred to her as “Nicolette Duvall.”

       “Duvall? My name is MacAfee, ma’am,” Nicolette responded.

     “You have been enrolled here, as a ward of Martine and Portia Duvall. That is your name on our records and you will use that name, young lady. As for your courses. You will be enrolled with your Primary courses in the Beauty Arts. Your Secondary courses will be in the Domestic Sciences,” Ms. Carlson instructed.

     “Now, as it is Saturday, you have the weekend to familiarize yourself with the school handbook, unpack your things, which are now in your room, and meet your roommate. You are dismissed. Use the campus map in your handbook, to find building 3. You are now in building 5. Your quarters are in room 202,” Ms. Carlson instructed.

      Nicolette found her way to the second floor of building three. She knocked. She was surprised to see a familiar face answer the door. It was Annabelle, the head sissy maid at the first Sisterhood party Nicolette had attended.

     “Do please come in Nicolette honey. I took the liberty of unpacking your belongings for you. I’ll show you where I put everything. This is your vanity, and your dressers. We of course share the bathroom and this lovely Queen sized bed,” said Annabelle excitedly.

     I’m in my 4th term. Novices, like you, room with 4th termers. Second and third termers room together,” Annabelle smiled.

      Nicolette looked around the room. It was spacious and very femininely appointed. It even had a set down, salon style, hair dryer in one corner. The tub did have a shower head, but students were encouraged to take scented bubble baths.

     “Well thank you Annabelle. It’s good to see a familiar face. I’m going to give this a try for two terms. Portia and I agreed on that,” Nicolette stated.

      Annabelle frowned a little, then smiled and hugged Nicolette excitedly.

     “Of course dear. We’ll have so much fun. You’ll soon melt right in here and just love it,” Annabelle said as she gave Nicolette a peck on her lipstick coated mouth.

     Nicolette was far from thrilled with the sleeping arrangements. Additionally this school was far and away, so much more feminine than she imagined. When her acceptance letter had arrived, she was surprised to see that, “New Sissy-Girl students reporting on Saturday should come to the auditorium.”

     The letter went onto say that, “New students should be attired in at least lady’s slacks, blouse and heels. Bodies should be free of hair. Students should either have the hair on their head, 1) In a roller set, 2) Freshly Permed or Body waved, 3) Or in an elaborate feminine hairdo.

    The day before reporting to Winthrop, Nicolette had been given a full body wax at Andrea’s salon. It had been both uncomfortable and humiliating. That evening he’d been given a full roller set by his Aunt Ariel.

     Very early Saturday morning he’d been awakened by Portia, dressed in a Donna Karan, grey, pinstriped suit and slack set, with Chanel blouse and black 3 inch heels. With her hair in curlers, netted, and covered with a fuchsia head wrap, she believed she would be the most fussily effeminate sissy in the group of 20 new students.

     She would be very wrong about that. On the drive to Winthrop, with much of the driving in the dark of early morning, Portia took numerous back roads with twists and turns to confuse Nicolette about the actual location of the school.

     Arriving at the school, Portia dropped Nicolette at the auditorium. “Kiss me baby. We won’t have any time for me to see you today. I’m taking your luggage to your room and heading back home,” Portia said to Nicolette’s surprise.

     It was in the auditorium that Nicolette found that the vast majority of the new students were dressed and coifed much more effeminately then she could possibly imagine.

      One “girl” had her bright red hair in a very fashionable up-do and was going on about her leg and bikini wax of the day before. Other “girls” had on frilly blouses and ruffled miniskirts. Several had freshly permed locks to display.

      At this point, with Nicolette standing in her new room, looking at her effeminate roommate, who had just kissed her, she realized she might have been tricked. She was certain, that Portia had seen to it that Annabelle was her new roommate and that Annabelle would be reporting directly to Portia’s sorority sister Michelle.

      Saturday evening, Nicolette did not sleep well. She slept a little better Sunday evening. She wasn’t sure what she would do if Annabelle in any way made a pass at her. Monday the first day of her new school, things seemed to go well. At least until 2:00 PM. She did well in her high heel walking class, though she was told her skirt management skills needed improvement.

     “Check with your roommate. She’s a fourth termer. She will be of great help,” the instructor intoned.

     He beauty class went well. She had practiced a lot on herself, Portia and Aunt Ariel. So did her home economics lesson. After lunch though, one of the “Dommes” (security staff) gave her a letter to report to the Nursing office by 2:00 PM. She got there just in time after her 1 O’clock, Speech and Mannerisms class.

     The nurse took her into a private exam room and said, “Strip honey. Right down to your panties and corset. Then get up on the exam table. That’s a good girl. We like our good girls here,” the nurse smiled sardonically.

     The table was designed for a gynecological exam, except Nicolette’s feet were fastened tightly in the stirrups and her arms were strapped tightly to the table. The nurse covered her with a warm sheet and laughingly said, “Just stay here honey. Doctor Sanders will be in shortly.”

      Doctor Elaine Sanders did make her appearance in a short time and introduced herself. Then she removed the sheet to examine Nicolette. She checked her butt plug first and asked, “Any problems removing and replacing the plug after a bowel movement? Does your roommate assist you?”
     “No ma’am, I do it myself. It is uncomfortable though ma’am,” Nicolette replied.

        “First of all dear, I am not called ma’am. I am Doctor, or Doctor Sanders. Secondly, it is supposed to be somewhat uncomfortable. It is designed so as to guarantee you walk gingerly and girlishly. When it gets comfortable, we remove it and insert a larger plug.”

      “What if your Mistress tells her boyfriend he can have a nice little piece of your ass? Do you think he’s going to care if you are uncomfortable? Wake up and smell the roses Sissy Mary. Butt plugs don’t feel good,” the Doctor laughed.

       The Doctor then checked the small boobies shaped by the corset. “These are why you are in my care right now honey. We need to make these bigger without the use of hormone injections. For the time being your Mistress wants to forego hormone therapy for you. Whatever,” the Doctor laughed.

       As Elaine Sanders probed Nicolette’s breasts, she noted a stirring in Nicolette’s panties. “Well something has got you aroused. Was it me touching your boobs? By the way, you are the ward of Portia and Martine Duvall, aren’t you? I’m reading your chart and school record,” the Doctor explained.

      “Were you aware that Martine has a sissy maid, Francine, I think, that she sent here for training?” Doctor Sanders asked.

     “No Doctor, I wasn’t aware of that,” Nicolette said.

      “Doesn’t matter honey. We need to take care of that unsightly boner you have. “Nurse Bancroft? Could you come to my office for a milking, please?” Doctor Sanders called into an intercom.

      It turned out Nurse Bancroft was the same nurse that had so carefully fastened Nicolette to the table. “Oh my, we can’t have this here. She needs a tight panty girdle or at least a panty brief,” the nurse intoned as she pulled down Nicolette’s panties, and rubbed a moist lubricant on her hands.

     She then unceremoniously grabbed the sissy’s cock and began to masturbate it, while discussing things with the doctor. “Is she here for breast plumping and suctioning? You know what’s going to happen? The first time her roommate massages her boobs with the plumping cream, this little slut is going to go, completely Nympho on her,” the nurse laughed.

      The doctor nodded in agreement and began to set up the breast suctioning equipment. About the time she was ready to rub the plumping cream into Nicolette’s breasts, Nicolette spurted wildly to the laughter of both Doctor and nurse.

       Nicolette was very nearly passed out. Both doctor and nurse rubbed some plumping cream into each breast, then they attached the breast suction cups to each boob. Turning the machine on to a medium setting they watched the reaction of the still swooning Nicolette.

       Nicolette soon came to the reality that her boobs were being mechanically suctioned. “Oh my, what is that?” she asked, as she squirmed to no avail against her tightly fastened bonds.

       “We have coated your little orbs with Breast Plumping Cream containing Collagen. The same plumping Collagen women and Sissies alike use to inject into their lips. Now we have attached suction cups to the orbs, so as to work the cream into your pores and suction your breasts, to develop them,” the Doctor spoke.

         “You will undergo this one hour treatment every Monday, Wednesday and Friday, at this same time. Every Tuesday, Thursday, Saturday and Sunday, your roommate will be required to massage your growing breasts with this same plumping cream,” the Doctor smiled.

      “Oh no, please don’t. Oh!” Nicolette wriggled in discomfort.

     “Don’t complain sissy. We either do this or we inject you with hormones that will shrink your penis and testicles. I personally prefer that, but your mistress thinks otherwise. In any event, we will be checking on you every 15 minutes for the next hour, to re-apply the cream,” said the Doctor.

     “If you get noisy we will plug your mouth with a penis gag. So just relax, and enjoy your mammary stimulation. I have been told by a number of sissies they enjoyed being put on the breast growth machine,” said Nurse Bancroft.

     To Nicolette’s embarrassment she had an erection when the nurse came back to finally end her breast enlargement treatment. The nurse gave Nicolette a large jar of plumping cream and a note to give to Annabelle.

      “Annabelle is to sign that note and return it to me. By signing it she confirms that she will apply your breast plumping cream on the four assigned days,” the nurse smiled.

      “You cannot go out in the lobby with that boner, girl. Use this hand cream and jerk off over the toilet,” the nurse ordered. “Now!” The nurse said.

       Nicolette did as she was told. Masturbating until she squirted her sperm into the toilet bowl, before flushing. Humiliating as it was, she wanted to get out of the Nursing office as soon as possible. Exhausted she returned to the room she shared with Annabelle. Thankfully Annabelle wasn’t there, so Nicolette took a nap until dinner time.

       It wasn’t until Tuesday, that Nicolette handed the note to Annabelle. Annabelle smiled and signed it. “It is nothing to be embarrassed about, Nicolette. I will be glad to help you. Take a nice bubble bath. Then I insist you apply powder, perfume and body lotion. While you set your hair, and apply lipstick I will be bathing,” smiled Annabelle.

      When the dark haired Annabelle emerged from her toilette, her skin glowed and her raven hair shone beautifully in the boudoir’s soft lighting. Annabelle then painted her own lips a deep crimson.

Annabelle approached the bed where Nicolette was lying down. Nicolette had covered her curlers with a satiny, floral, bandeau scarf, carefully tied with a bow in back. Her lips were painted a glossy, coral pink. Annabelle unscrewed the lid from the jar of plumping cream.

       She then lowered the straps on Nicolette’s nightgown so she could reveal her breasts. “I’ll lie down here darling. Okay? Now I’ll massage your breasts. Lie flat dear and relax. You look so sexy and pretty tonight honey,” Annabelle cooed.

        Nicolette did her best to relax, by closing her eyes as Annabelle massaged the plumping cream into her tiny breasts. “Your breasts will be so lovely one day Nicolette. Your mistress will love them so much,” Annabelle continued to coo.

       She noted the slight swelling in Nicolette’s panty. Nicolette had already told her she would be wearing a restrictive panty girdle around the campus from now on. Annabelle was glad she wasn’t wearing it this evening.

       “Nicolette? If you would like, I could stop briefly. You are becoming aroused. I don’t want your balls to ache tonight, honey. Let me relieve the tension in your penis? Please?” Annabelle smiled.

         Nicolette was fearful this would occur. “Not just yet. I actually enjoy the feeling I’m getting from you massaging my breast area, Annabelle, dear,” Nicolette sighed.

     Annabelle continued with her ministrations. Nicolette showed her pleasure by giggling softly and wiggling her butt. “Annabelle, come lie down beside me and rub my breasts, please? Come closer, will you, love,” Nicolette whispered, throatily.

     Annabelle lay next to Nicolette and surprisingly, Nikki, kissed her softly. Annabelle could not control herself any longer and kissed Nicolette all over her smooth face, and sexy eyes.

     Nicolette increased the passion by hugging and squeezing Annabelle around her torso, and grinding her erect penis into Annabelle’s crotch. “I think we need to get you nice and rock hard too, girl,” Nikki, growled raspingly.

     She grabbed Annabelle’s penis, inside her nighty, and French kissed Annabelle as their crimson and coral lipsticks mingled.

     Annabelle grew harder with Nicolette touching her, than she had been with her mistress touching her, the last time they’d been together. It didn’t bother her. She could shrug it off. If she liked sissies and boys more than women, that would be okay.

     When Annabelle had reached the peak of her hardness, Nikki went down between her girl-friend’s legs and started licking her penis. “Annabelle, what would you like me to do with this? I can suck you off, or I can remove my butt plug and sit on your penis?” Nicolette said.

     “No offense, but you cock isn’t very big Annabelle. So if I was going to have something in my rear end, this might be the time to do it?” Nicolette inquired.

     “Would you really want to sit on my penis Nikki, dear? That would be lovely! Annabelle gasped. “Here darling. Let me help. We could use some of this plumping cream for lubricant,” said the excited sissy.

     Nicolette removed her butt plug slowly. Then she used her fingers to coat the inside of her rectum. She’d only been wearing the plug for a few days but it had certainly expanded her sissy pussy.

     An excited Annabelle sat on the end of the bed, her feet firmly planted on the floor. Nicolette sashayed over to her, and slowly lowered herself onto Annabelle’s penis.

     “Oh, Anna darling, please be gentle. I’m a virgin you know? Let’s take it nice and slow. Please?” Nikki implored.
      “Why of course, Princess Nicolette. I want your first experience to be memorable for its tenderness, my darling,” Annabelle promised.

       Nikki moved slowly up and down, upon the stiff penis. Annabelle only gave very mild prods. As Nicolette loosened up she began to move her tight ass in circles around Annabelle’s penis. “Anna honey, please touch my cock?” Nikki asked.

      Both sissies were highly aroused. Something had to give and Annabelle began squirting first. As her sperm filled Nikki’s sissy pussy Annabelle shrieked and panted. Nikki moved her ass faster, up and down and squeezed the last drop of spent sperm from Annabelle.

     Annabelle laid back exhausted, as Nikki smothered Anna’s face with kisses. “Oh that was so good, Princess Anna. You know what though? I still have an orgasm coming, and I think you’re going to suck my cock,” Nikki leered.

     “Oh I will Nikki. On your back honey. Yum!” Annabelle said as she took Nikki’s swollen penis in her mouth. Nikki did not last long. Annabelle sucked every last drop of sperm from Nikki’s cock. The two exhausted sissies, slept the evening away in each other’s arms.

       All throughout the next month, even though Nikki dreaded the three hours a week on the breast suction equipment, she could not wait for Annabelle’s evening ministrations with the plumping cream.

Chapter IV: Mother (Mater) Martine

     Nicolette did quite well during her first month at Winthrop. Well enough, to her surprise, that she was given permission to spend an extended holiday weekend away from the school.

     She and Annabelle were seated together having lunch, when a Domme approached their table. “Nicolette Duvall? Here, you are to report to your academic counselor at the end of the school day,” said the Domme, handing her an envelope.

     Nikki was quite nervous in the waiting area. She was certainly happy when she entered Ms. Carlson’s office and the usually serious counselor was smiling.

      “Well Nicolette, I am quite happy with your performance thus far. We all are. The instructors love the beauty treatments you give the other girls in your salon classes. You have a terrific fashion sense. You walk with a lovely mince and have a nice little butt wiggle,” Ms. Carlson stated.

       “I look at you and I see the foundation for a charming, young, Winthrop Girl. Your breasts seem to be coming along nicely, from the plumping cream and the suction treatments. So, here is a permission slip for you to have a complete girly makeover,” Ms. Carlson congratulated.

       “You have the morning off from classes tomorrow for the makeover. You should pack this evening. You Mistress will be picking you up, for an extended 3 day weekend at 2 PM tomorrow. Your makeover will also include a full wardrobe outfitting, so dress casually when you go to the salon,” Ms. Carlson explained.

       “Pack one cosmetic carry all and one travel bag this evening. We will see you next Tuesday for classes. Enjoy your weekend with your Mistress. I’m sure it will be exceptional,” smiled Ms. Carlson.

        Nicolette was superbly excited when she arrived at the school salon in the A.M. Friday. “So, we’re having a weekend with Mistress, are we? Do you want me to make you beautiful Nicolette? I mean really stunning for your Mistress?” Serena, the salon manager asked.

       Nikki shivered with delight at the thought. She wanted Portia to ravage her. “Yes, please ma’am. Make me as gorgeous as you possibly can. I want Mistress Portia to love how I look,” pleaded Nikki.

       Indeed when Nicolette Duvall stepped from the salon, to mince to the assembly hall, where sissies awaited their Mistresses, she was indeed a new young lady. Before she seated herself, next to where her two pieces of luggage had been placed, she spun to take another look at herself in a full length mirror.

     She could not believe the transformation she’d undergone. She posed in the mirror, looking this way, and that. Her shiny, new Strawberry locks, glimmered with the added, golden blonde highlights. Her hair was done in a long bob or “Lob”.

     After coloring Nikki’s hair, the stylist had taken her nearly shoulder length hair and using a curling iron, had given Nicolette, long “Sausage” curls. Her face was heavily but tastefully made up. It was the first time she’d worn really Red Lipstick and it made her feel really grown up.

     Her, white, four inch heels and smoky grey hose, set off her black and white, triangular, patterned mini-dress. Her butt looked nice and firm in her panty brief. Her cinched waist was set off by a wide white belt.
     Her piercing studs were removed, and replaced with white, gemstone earrings, embedded with an ebony, Black Rose, of the Sisterhood.

     It was her breasts, though, that took her breathe away. At the salon, when she was put in a “push-up” brassiere, they had been able to achieve a 34A cup, without any padding. She hoped, Portia would appreciate all she’d been through, with the suction equipment and breast massage.

     Her fingernails had been lengthened by extensions and painted a cherry red. She was just being seated when one of the sissies, looking out the large Bay Window in front of the hall gasped, “Goodness me. Who belongs to this Mistress? She is an absolute stunner!”

    Nikki looked. It was Portia! Looking resplendent in a fashionable, ladies, skirted business suit, her chin length, auburn bob, shining in the sun. “Oh my, it’s Mistress Portia. Please Mika, open the door, so I can go out and meet her?” Nicolette begged as she picked up her makeup bag and suitcase.

     “Oh, lucky you, Nicolette. No doubt you’ll have a long lovely weekend,” squealed Mika.

    Nicolette minced ever so carefully, stopping a few feet in front of Portia. Portia had already stopped walking. Why not? Better to let the sissy come to her. Nicolette, curtseyed deeply, holding it an extra second or two, as she exclaimed, “I am both honored and thrilled to see you my Mistress!”

    Nikki struck the acceptable model’s pose for proper inspection by a Mistress. Portia took in her sissy’s appearance before nodding her acceptance. “Very, very nice, Nicolette. You have been beautifully turned out. I’m pleased.”

     “I’ll take your large bag. You carry your cosmetics. I will assist you into the front seat and buckle you in also,” Portia insisted.

      As Portia buckled Nikki into the passenger seat, she held her firmly by the chin, and kissed her full on the lips, letting her tongue linger in Nikki’s mouth. “I don’t know if I can wait to get you home to get you into my bed? I might have to stop and get a room for the evening,” Portia laughed.

     On the ride out to the main highway, Portia complemented Nicolette on her new décolletage. “You have grown quite well in the booby department, kitten. I’m impressed. I’ll need to take a closer look see this evening,” she smiled.

     Once on the main highway, Portia described the new order of things as far as living arrangements went. “My mother has renovated the entire 3rd story loft of her home. You and I will be staying there for the foreseeable future. This was discussed and agreed upon among us. Including your aunt,” Portia informed her sissy.

     “I must tell you that mother has a rather high position within the Sisterhood. She has a financial interest in the school you attend and is on the board of directors. She has a long record of involvement and success within Casandra,” said Portia.

      “Just as the Headmistress at Winthrop was called Mater Directress, my mother, Martine has also rose to the eminence of Mater. So, you will act accordingly around her. She is Mater Martine to you. You will also hold your dip, when your curtsey to her, until she tells you that you may rise,” said Portia.

      “Do you fully understand me Nicolette? Even this evening, you will acknowledge my mother, before your aunt. Only after mother has spoken to you, may you acknowledge anyone else in the room. You have all that?” Portia asked.

       “Yes Portia darling. I fully understand. I only want to please you, Mater Martine and my Aunt Ariel. I want to please all of you fully,” said Nicolette, sincerely.

       Arriving at the Duvall residence, Portia and Nikki took the stairway in the rear of the home to their private entrance to the loft. Shortly after there was a knock on their door. It was Francine, the personal sissy maid of Martine Duvall.

       “Ms. Portia. Madame requires your presence at 5:30 for refreshments in the anteroom, with Ms. Ariel MacAfee. Dinner will be at 6:15, in the main dining area. Will you be needing anything from me presently, Madam?” Francine asked.

     “No Francie, I won’t be needing anything. You may tell mother we will be either on time or early,” Portia spoke.

      Portia gave Nikki a tour of their new “Love Nest” as Portia called it. Nikki noted he had his own, very fussy, girl’s room.

      “You will sleep in your room unless I require you for sexual duties,” informed Portia.

       Portia then, worked on her own hair and makeup as well as Nicolette’s. When she was satisfied, she checked their attire. Satisfied again, they took an inside staircase to the anteroom. Portia made Nicolette wait outside the doorway, while she exchanged pleasantries with her mother and Ariel.
      “Then she called out, “Nicolette, you may enter!”

     Nicolette entered with some trepidations, obviously concerned she may falter on the necessary protocol. She also hoped she looked good to everyone. She wondered how her aunt would react to her transformation and her growing bust size.

     She stopped an accepted distance from Martine Duvall, performed a perfectly girlish curtsey dip, and remained dipped in subservience. As she dipped, she announced, “I am so honored to meet you and be in your presence, Mater Martine.”

  Martine stood up, circled her, and then clapped her hands together twice.

 “You may rise my child, and assume a proper model’s pose,” Martine ordered.

     The “Proper model’s pose” meant for the sissy to stand erect, with their bust, thrust out prominently, staring off into space. Their feet should be slightly apart, with the left foot slightly ahead of the right. Arms were to be held languidly at their sides, with their wrists, limped and their fingers daintily spread.

      Often, a number of Cassandra Sisters would sardonically refer to it as, “The Air-Head Bimbo Pose.”  Martine inspected Nicolette carefully, before saying, “You Aunt Ariel is here child. I think you should acknowledge her, should you not?”

      “Yes Mater Martine. Thank you so much. Aunt Ariel. I am excited to see you. I have missed you so much this past month,” Nikki prattled as he curtsied obsequiously to his aunt.

        “I must say, dear Nicolette, if this is any indication of your new behavior and appearance, I will miss you much after this weekend,” said Ariel as she arose from her chair and hugged her sissy nephew.
       “You look lovely my Angel, and I look forward to cultivating you as my loving niece,” said Ariel as she gave Nikki a sweet peck on his dainty lips.

         Francine entered the room as Portia called for the sissy maid.

      “Miss Ariel and I will have our favorite top shelf Kentucky Bourbon. My daughter will have our best Scotch. All three on the rocks. Will you allow your paramour an alcoholic beverage, dear daughter?” Martine inquired.

      “Hmm. Good question mother. I think a glass of our best Pink Chablis would be in order,” smiled Portia. Portia was thinking ahead, about having her little slut, tipsy, and “well-oiled” at bedtime.

      Dinner was elegant. Nicolette was permitted another glass of Chablis during dinner. When dinner was nearly over, Portia, leaned over to her mother. Nikki and his aunt were chatting nicely.

     “Please excuse my intrusion mother. I wanted to know if you are planning on partaking of our sweet Nicolette at bedtime,” Portia whispered.

     “Of course I would love that darling. I can always wait until you are finished with her, of course,” smiled Martine.

     “That’s wonderful mother. I placed her room closest to the entrance door to the loft. You will not have any trouble entering the room unnoticed. Once I have ravaged her I’ll send her there,” smiled Portia.
       “Ariel, are you going to spend the evening here. If so we can all have a small Benedictine and Brandy,” exclaimed Martine.

      “Only if I can have Francine for the evening Martine,” laughed Ariel.

      “Of course you can have Francie for the evening darling. Let’s have that drink of B&B,” laughed Martine.

       Francine, Martine Duvall’s sissy maid, had been an office manager for Duvall Financials, a family owned business belonging to the Duvall family. He had also been a predatory sexual harasser, preying on single, female employees.

      It reached the point where several women came forward, and Martine agreed to file charges. A few of the women gave evidence of date rape. Martine pulled a lot of strings to have the date rape charges heard in front of a judge that was a member of the Cassandra Sisterhood.

      After the guilty verdict came in, the judge held a private sentencing hearing. She gave the office manager a choice of seven years in the state penitentiary, or two years of temporary feminization. One year would be spent at the school known as “Winthrop at Greenbrier.” The second year would be spent as Martine’s sissy maid.

      At the end of the two years, Francine was so thoroughly sissified, she begged Martine to allow her to stay. Martine allowed it. The only sexual contact the two had was when Martine had the sissy provide oral sex.

      The fact that Ariel wanted the sissy maid for the evening made little difference to Martine. Especially when she was planning to have a sexual liaison with her daughter’s, very own, sissy boy.

    Everyone was poured a B&B by Francine. Soon, the tipsy couple of Portia and Nicolette went upstairs to their loft. Portia pulled Nicolette into Portia’s boudoir, and pushed Nikki to the bed.

     Portia pulled off Nikki’s high heels and told Nikki, “Get your dress and panty brief off. Then remove your plug. Clean yourself nicely. Then return to my bed. For starters, I will remove your bra, and treat myself to your new breasts,” Portia commanded.

      Nikki returned to the bed, after her ablutions. She slipped under the covers. Then Portia put her arm around Nikki’s shoulder and pulled her to her chest. Taking Nikki’s bra off, Portia cupped both sexy, little, swelling orbs, on Nikki’s chest.

     “Oh my I need to suck on both of these. Yum,” she said, as she sucked on one nipple and played with the other. She grabbed one of Nikki’s hands and placed it under the covers, touching the strap-on faux penis Portia was wearing.

      Nikki had been panting from her ministrations of his breasts, but now touching the strap-on penis, he whimpered. “Oh my, Mistress, it is big,” he cried out.

      “Well it is bigger than Annabelle’s from what Michelle tells me. But, there are bigger penises, both real and artificial,” she teased. “Don’t worry dear, I have gotten a full report of all your goings on at Winthrop. I’m happy you got loosened up with a real penis,” smiled Portia.

      “I will be picking your roommate for you during your second term also. With Mother’s connections I’ll always be fully aware of your progress,” laughed Portia.

       She had Nikki fairly hot by now, so she told him to position himself on hands and knees facing the foot of the bed. “Get that pert little ass of yours pointed into the air. Momma is going to mount her little, sissy, French Poodle,” laughed Portia.

       Portia placed a suppository extension on a large tube of K-Y Jelly. She squeezed the tube to emit some jelly into the suppository holes and carefully slid the extension into Nikki’s anal opening. Nikki tightened.
      “Loosen up girl. I’m getting you well lubricated. Then Mistress is going to bang her sissy’s bung hole,” Portia laughed.

       What Portia liked about a strap-on was the ridge where it contacted her body. The slight ridge would rub against her clit and stimulate her while she assailed the ass of her subject.

      As the most senior member of Cassandra, at her former sorority, she had used the strap-on with numerous female pledges, and even ranking members like Michelle. Michelle might be dominant with other girls, and sissies, but with Portia she was a simpering pussycat.

     Nikki grunted and let out a sigh as Portia carefully entered him. She started slowly, then she would push firmly and finally her faux penis was fully buried in Nikki’s anal cavity.

     Portia kept a steady rhythm now that the strap-on was fully implanted in Nicolette’s butt. She giggled while Nikki, panted and mewled.

     “You like it? Don’t you, you sexy girl? Wait until you see what we have planned for your encore,” laughed Portia.

     Portia’s passions were rising, with the piece, nearest her body, rubbing her clitoris. She picked up the pace and heard Nikki howl as she rode him like a pony. “Oh yes. That’s better. Hang on Nikki. Mistress is coming. Oh my!” Portia exclaimed as her dam burst.

    She and Nikki lay in each other’s arms for some time, as Portia kissed her sissy boyfriend’s face, and Nikki hugged his mistress. “Nicolette dear. I am exhausted but we are still going to see to it that you get to orgasm honey. It just won’t be me giving you that Orgasm dear. Come with me,” Portia added.

    Portia escorted Nicolette to the door of his prissy, little bedroom. Knocking on the door she said, “Mother, are you awake? I’m bringing in Nicolette to get into bed with you,” Portia said, as the startled Nikki gasped.

     “Of course I am awake. What with all the noise you two were making. Come to Mother Martine, Nicolette. I will take care of you,” Martine sang out, as Portia opened the door and shoved Nikki into the room.

     Martine had a night lite on and looked at Nikki standing by the bed shaking, his arms wrapped around his bosom. “Come to Mater, dear Nicolette. That’s it. Get into bed and suck on one of Mater’s breasts darling. Oh yes, now what a good girl you are,” Martine said, as Nikki followed her instructions explicitly.

     Martine reached under the covers, and grabbed his swollen penis and squeezed. “This is going to feel so nice inside of my pussy. Here darling, let me climb on top of you,” Martine said as she began to ride the sissy boy’s swollen cock.

Continued in Part Two
In Part Two, we will meet a new character, Jocelyn. She is Nikki’s older cousin and the daughter of his Aunt Ariel.
   

Like what you read? Have comments or thoughts?
Contact Priscilla:
priscillagaybouffant@gmail.com