The Samantha Project - Chapter 46 - 50
An epic story of power, money, politics, deceit and love. Epicene Sam is given to Mistress Ann for the final step in his transition into Lisa’s wife and concubine.
Femdom, crossdressing, hair and hair salon, corseting, heels, appliances attached, sex, illustrations.
The Samantha Project by G. L. Hudson
The next morning found the three girls snuggled together in their king size bed. Because of the previous evening’s circumstances, the girls had retired without any additional sexual bonding. But Lisa’s schedule for Sam still had one piece of unfinished business. She and Harriet had decided the previous evening that Harriet would take Samantha one step further in the morning.
After sharing good morning kisses, Harriet asked if she might have some private time with Samantha. Lisa dutifully agreed, and she slid out of bed and headed to the bathroom. Harriet snuggled up tightly to Sam and said, “Samantha, you are going to be one of the most beautiful girls ever. While you are being trained here in Paris, may I come see you sometime?”
“Of course Miss Harriet, whenever you like.”
“Thank you. I look forward to spending some time with you. Before you go off to your feminization and hormone therapy, I would like to do something for you while you are still in your full boy mode.”
“What is that?”
“I would like to allow you to just once in your life make love to a girl when you are on top.”
“But as you said yesterday, you’re not a real girl.”
“It’s as close as you’re ever going to get Samantha. Would you like the top just this once?”
“Why not?” and Sam pulled up his negligee.
“Wait, you have to start between my legs, sweetie.”
“But … but you don’t have a real vagina, Miss Harriet,” he complained.
“My surgery left me with all of the nerve endings still intact. Your tongue will still bring me intense pleasure, Samantha. Come on, just like you do for Lisa. And when you’re done, you may take me from the top position.”
This was a big step for Sam. Even though Harriet looked like a normal girl, Sam knew he was going to perform cunnilingus on a male. He was going to go down on a boy! And he also knew that he really had no choice in the matter. He was going to be a Hawthorne concubine, so he was going to have to accept the fact that he would be expected to cheerfully provide sex to all of Lisa’s family; even those born with an unfortunate disadvantage.
With a big swallow, Sam slid between Harriet’s legs and looked up to her. “You may begin, Samantha. Just like you do for Lisa — nice and slow, soft and feminine.”
Harriet was impressed with Sam’s ability and concentration. He moved slowly and deliberately and gave Harriet more pleasure than she had ever experienced from anyone else going down on her. And that is saying a lot, because they practiced constantly at St. Hermaphrodite.
On the other hand, Sam quickly realized that he wasn’t pleasuring a real girl’s vagina. For one thing, the scent was all wrong. And the texture and juices and details of the labia were all wrong. And finally, Harriet’s clit was nothing like Lisa’s — and Sam should know. He was intimately familiar with Lisa’s nether region.
Harriet didn’t keep the effeminate boy between his legs very long. She and Lisa had made their point and Sam had willingly obeyed. Harriet could move on. She thanked Sam for his attention then opened her legs for him. Sam hiked up his negligee and moved up on Harriet. He took his position and slid his cock into her pre-moistened vagina. He and Harriet French kissed as he began sliding in and out of Harriet’s vagina. Harriet kept up with him, squeezing her muscles and milking her boy as best she could. In only a few minutes Sam was spurting his semen into Harriet.
Sam collapsed on Harriet and received another soft kiss followed by her tongue. “Was that ok for you?” Harriet asked.
“Yeah, great,” Sam replied.
“See, you can have fun with another boy,” she said with a grin. “At least if he has the proper modifications, right?”
“Yes Miss Harriet, and you have the correct modifications,” he answered with an impish grin.
“Why don’t you go see if Lisa will let you in the bathroom? I’ll wait for the two of you to finish. The two of you might want a little private time together.”
A few minutes later Lisa returned to the bedroom. “So? How did it go?”
“Fine,” Harriet answered. “He went down on me and performed just great. You’ve trained him very well.” Left unsaid was their post-oral communion. Harriet did not have permission to allow Sam to fornicate in the top position. It was Harriet’s little gift to Samantha — girl to girl.
At the train station Harriet was the first to board her train back to school. The girls hugged and shared real kisses — no faux kisses — and the two inamoratas waved to Harriet as her train pulled out of the station. Sam, Lisa and Andre had to kill about an hour in the coffee shop, waiting for their departure back to Paris. It was an uneventful trip back, and both girls were happy to return to their Paris accommodations.
They spent the rest of their vacation shopping, sightseeing and clubbing. The following week and a half they were in a club every night. Lisa even had Sam dancing with boys a couple of times. Things were different now, and both girls realized it. Sam had accepted his new role and future. He was to become a concubine and serve his beloved Lisa. His liaison with Harriet had served a couple of purposes. Not only was he introduced to that little Hawthorne family quirk concerning the sharing of concubines, but he had also accepted his role of submitting to and obeying Lisa’s directions. When she “suggested” that the two of them dance with boys, with a pretty and sexy smile Sam readily agreed.
Now Sam hadn’t totally changed into Samantha the concubine. In spite of his favorable experiences with Miss Harriet, Sam still had his streak of homophobia. While dancing with boys was still not one of his preferences, he accepted the premise that he was expected to happily agree to any and all of Lisa’s requests. So with a big smile he accepted the hand of another male and followed him onto the dance floor where they spun and gyrated to the rhythm of the music. Lisa was especially proud and happy to see Sam’s positive attitude, so she pushed him one step further. At the conclusion of their dance, Lisa gave her manly dancing partner a big wet kiss. Then she looked at Sam, who instinctively understood that she was telling him to do the same. With his ruby red, collagen enhanced lips, Sam too gave his boy a sexy kiss. Just by looking at the boy, both girls could see Sam’s impact on the adolescent male’s hormones. Sam’s female persona of Samantha was one hot chick!
And Lisa loved what she saw. Her panties were instantly wet and she quickly called an end to the evening’s festivities. She had to have her courtesan back between her legs.
The rest of their vacation flew by for Sam. He was having the time of his life, enjoying the complex emotions of being a beautiful and sexy girl. During their remaining time together, they made additional stops at their favorite salon to get a facial or wash and set. They visited all of the best shops and boutiques and bought even more hats for themselves. They dined at the best restaurants in Paris and then went to the most upscale clubs on the continent. And after their dancing, they enjoyed a Grand Marnier crepe before returning to their love nest for an intimate conclusion to the day.
Sam relished his role of submissive and sexy courtesan. He liked being female and pretty and attractive. His reservations and doubts and baggage had all been left behind him. He could now accept and surrender to what he always wanted but could never admit. He enjoyed having Lisa take the lead and control his daily activities. He enjoyed being submissive and demure. He enjoyed flirting with Lisa and allowing her to seduce him and sexually dominate him. No dear reader, Sam was not submitting to a life of servitude and domination. He was enjoying and partaking in a partnership of wonderful vistas and mutual love. He was a willing and grateful participant in the next phase of his exciting new life. Sam was looking forward to becoming Samantha - the wife and concubine.
And he was looking forward to his training — although his enthusiasm was tempered by his anticipated isolation and loneliness. He was going to miss having Lisa with him on a daily basis. Entering into new territory and activities usually has its share of trepidation and anxiety for most people, and Sam was no different. What would his tutor be like? Would she like him? Would she be strict or lenient? Could he learn a foreign language? Would he fit in with his new environment? Could he really learn how to become a convincing female, an acceptable concubine and a loving wife? On and on the list of potential anxieties and questions went.
Intellectually, Sam knew all would be well. The family would make sure of that. But still those fears can haunt anyone embarking on a new journey. But in spite of all that, Sam knew all would be well and he was anticipating his journey with more enthusiasm than worry.
And so their fairy tale adventure drew to a close. On their last evening together in Paris, they dressed in their finest dresses, piled their hair in fancy styles and applied their sexiest cosmetics and fragrances. They dined at their favorite restaurant, sipped their favorite champagne and held hands under the table. And after a satisfying meal, they went to Escualita and danced with beautiful boys and sexy transsexuals. Andre again grabbed a tiny little table for the two beautiful girls to rest at while they sipped champagne and recuperated between their next dancing marathons.
And at the end of the evening, Lisa sensually peeled her courtesan’s expensive and feminine clothing from his soft body, applied fresh lipstick and fragrance, wrapped him in a sexy pink negligee and then took him in her arms. Lisa placed a soft kiss on Sam’s lips while she wrapped her arms around his waist and tightly squeezed his firm ass. She reached for Sam’s manicured hand and led him to another evening of pre-conjugal bliss in the City of Light. As always, Sam began between Lisa’s thighs; gently and slowly encouraging her to ever higher decibels of ear-splitting screams and intense, satisfying orgasms. Sam was the consummate chamber maid; soft, effeminate, patient and talented. If his plucked penis had been properly tucked and pantied he would have made a superb lipstick lesbian.
After spending a successful twenty minutes pleasuring his mistress, Sam was invited to roll on his back and lay over the edge of the bed. Sam loved this position. He slowly slid over the edge of the bed as Lisa straddled her paramour. Sam’s penis was already standing at attention as Lisa lowered herself and took Sam into her loins. As Sam slid further over the edge of the bed, Lisa leaned back and put unbelievable pressure — and exquisite pleasure — into Sam’s remaining masculine holdout. With Sam’s hair brushing the floor — Sam loved it — and the blood rushing to his head, his princess controlled his thrusting hips and slowed him down to prolong her pleasure. As much as Sam loved the tightness and fine sensitivity of Lisa’s cunt against his cock, Lisa was even more thrilled with the exquisite stroking against her clitoris. And of course Lisa was controlling the action.
Princess Lisa literally milked every ounce of pleasure from her prostrate lover as she brought herself to another orgasmic scream. Sam tried his best to thrust and stroke against his lover while she was enduring another glorious orgasm, and he eventually brought himself to nirvana. Both inamoratas were more than happy with the results of another successful evening of pleasure and training. Lisa had her effeminate boy on schedule for his conversion into her feminized concubine and boy-wife. All was well in Paris.
Vacation was over. It was Monday, the day after three glorious and successful weeks in Paris. In two days Lisa would be in class at Harvard, and today Sam would be introduced to his mistress for the next 18 months. Lisa wanted her fiancée in the right frame of mind, so she dressed him in all pink. Sam had a luscious and lacy pink push-up bra squeezing his breast forms together for cleavage. His matching panties and camisole were pink and lacy also. He wore pink stockings with pink 2 inch pumps. Of course his frilly dress was a bright pink with white lacey edges around the hem and cuffs. And to finish off her pretty boy, Lisa gave him pink lipstick and tied a pink ribbon in his hair.
Sam had never been presented anymore effeminate and prissy than he was now dressed. He looked beautiful and totally controlled. Lisa was full of mixed emotions; she was very proud and happy with her boy and his conversion into her courtesan and fiancée. But she was also sad; today she would be parting from him for the best part of 18 months. She would be back to visit, but those would be short visits with limited opportunities for privacy and fun.
“Time to go, Samantha. Ready?”
Sam took a deep breath and with much trepidation answered, “I guess so.”
Lisa could sense the concern in his voice. She tried to reassure her boy, “Don’t worry Samantha. You are going to have a wonderful time. You’ll do just great.”
“I hope so. I don’t want to disappoint you.”
“What a wonderful thought,” Lisa thought. He truly was accepting his situation and his devotion to Lisa. Damn! He was going to be just perfect, she thought.
“You won’t. I know you will be perfect, sweet Samantha. Let’s get going before I get all choked up.” Lisa took Sam’s hand and led him to the car.
The vehicle came to a halt and Andre walked back to open the door for the two girls. Sam swallowed and Lisa leaned over to give him a soft kiss on his pretty pink lips. “Come Samantha, it’s time for your next step.” Lisa again held Sam’s hand and led him up to the door of a very nondescript building. The door was old and weathered, but the rest of the building looked to be in good condition. Lisa reached up and used the door knocker to announce their arrival. The door opened almost immediately.
The first thing Sam noticed was her eyes. They were brown with little mascara and makeup and they immediately locked on him. Those eyes smiled at him! They looked kind, matronly and yet very sharp. They quickly flashed up and down him, taking in his posture, facial expressions, relation to Lisa (slightly behind her) and of course his dress. Then her lips began turning up. She liked Sam. He could tell. Little lines formed at the edges of her eyes and they squinted every so slightly as her big smile greeted him.
“Lisa, welcome, welcome. Please come in,” and she pushed the door open. Lisa and Sam stepped in and stopped, waiting for the woman to show them in. But instead the woman continued looking at Sam. “And you are Samantha. I was expecting a pretty boy, but you are even prettier in person. Samantha, welcome to your new home. Please walk this way.”
The woman led the two girls into a parlor. “Lisa, would you please wait for us in here?” and she opened a door to another room. Lisa walked into the other room and closed the door. It was a small room, but it had a desk with a monitor and set of headphones. Lisa took a seat, slipped on the headphones and then began watching the proceedings in the adjoining room.
The woman pointed to a small couch and invited Sam to sit. She watched as Sam used his best feminine training to take his seat. The woman smiled and sat down next to him. She sat very close to Sam and quickly placed her hand on Sam’s knee.
“Samantha, my name is Mistress Ann. That is how you will address me from now on. Understand?”
“Yes Mistress Ann.”
“Good. When we talk you will answer me with yes ma’am or no ma’am. Ok?”
Mistress Ann leaned away from Sam just a little so she could get a larger view of her new student. She took a deep breath and let it out slowly as she surveyed her young charge. “Samantha, you are a very pretty boy, as I said before. I look forward to guiding you through your studies and your maturation into a beautiful concubine. Lisa is going to be very pleased when you are finished here.
“There are some things we must discuss up front, Samantha. I think it is very important for both of us to fully understand what is expected of each other, and why we are here. I don’t want you to have any doubts as to your purpose here. Honesty between the two of us will be crucial to your successful transformation. If you have questions now is the time to ask.”
“Thank you ma’am.” Sam said.
“So let me explain why you are, and it starts with Miss Grace. Has Lisa explained Miss Grace’s history and upbringing?”
“Then please bear with me, but I like to be thorough. I am going to repeat the story and you may hear a few things you did not hear the first time.”
Actually, Lisa had left very little out. Sam thought Mistress Ann was a much better storyteller than Lisa, but there were only a few new facts and insights.
“So here are we are now, Samantha. Do you have any questions yet?”
“Very good. Lisa has proposed to you and I understand that you have accepted. Congratulations on your engagement.”
“Now, what does that mean? Being engaged to Lisa, a Hawthorne, is different than normal situations. You are a boy and Lisa is a girl. Under normal conventions that would mean that you would be the husband and Lisa would be your wife. But that is not the case here. Correct?”
“I understand Mistress Ann.”
“I know you do Samantha. I have heard that you are very intelligent. But like I said, I want there to be no surprises for anyone. In this case you are to become the wife. You are to serve Lisa in the traditional role of a wife. But it is a little more complicated than that. Lisa will not be your husband. That would be silly. Instead, she is to become your mistress and you are to become her concubine. In your marriage vows you are to pledge your life and services to Lisa as her wife and concubine. And Lisa will pledge to be your mistress. Now what does that mean?”
Mistress Ann paused and looked at Sam. Sam understood it to be a rhetorical question and he merely waited for her to continue. “You will promise to do as Lisa instructs you. This is not meant to be a typical marriage where both parties are equal. That is not what this about. Instead, Lisa will look after your best interests and you will assist her in any way you can to help her do that. You must trust your mistress and accept that she always has your best interests in mind. This is critical Samantha. Can you do this? Can you accept a life where Lisa will take care of you and you must always do as she asks? Always?”
Sam’s throat was dry. He was being asked to fully commit and accept what Lisa had been leading him towards. He had to put up or quit. Today was the day. Sam swallowed and squeaked, “Yes ma’am. I understand and I accept my role. Lisa will be my mistress and I will be her wife and concubine.”
Mistress Ann smiled at Sam and congratulated him. “I know this is a big step and it can be scary. But I have helped several boys in your very same situation, and everyone has thanked me over the years. They still send me Christmas and birthday cards telling me how happy and how blessed their lives are. I am sure you will be no different Samantha.
“So what is my role in all of this? I am to help you on the path of your great adventure. Becoming a Hawthorne concubine requires many skills and much knowledge. I am here to help you learn everything you will need to know. You must first learn how to live as a beautiful girl, but you are not to become a girl, Samantha. While you are with me there will be some cosmetic surgery to make you even more beautiful and feminine. But under your dress, tucked beneath your panties you are to remain a male. That is what Lisa wants, and that is what it means to become a Hawthorne concubine.
“So I will teach you how to dress and walk and talk and live your life just like any other girl. Like any other “special” girl that is. Remember, you are to be a society girl, so you must also learn the etiquette and traditions of being in this new society. Much of it will seem very foreign, capricious and even difficult for you. But not to worry, I will teach you everything you need to know.
“Next, after becoming an acceptable society girl, you will need to know how to run a home. Now I am going to teach you how to make a bed, wash clothes and iron, and all sorts of domestic duties. But that will be only for background knowledge. You will not be expected to be a domestic, but you will be expected to manage, organize and control your domestic help. It is good to know these jobs so that you know how best to manage your boys.”
“Yes Samantha. All of your domestic help will be pretty boys much like yourself. The Hawthorne family is a complete matriarchy, from their level down to the help. Most of their personal employees, your employees, are feminized boys with some being full transsexuals. You will find that they are much more loyal and grateful than most women, and definitely better than unconverted men. But more of that later.”
“Yes ma’am.” This was another surprise for Sam. He had never thought about the domestic help being boys. They were all so convincing as girls. He couldn’t help his mind from wandering just a little bit; he wondered about Jennifer.
“And finally, you will perform as Mistress Lisa’s hand and chamber maid. That means that you will be at her beck and call for any duty she might require. You must know how to bathe your mistress. You will have to pick out her clothes and help her dress. You must know hair care and makeup and how to give her a manicure or pedicure. You must be able to assist your mistress in all of her personal hygiene and clothing needs. You must even know how to do some sewing in cases of emergency.
“You must also know how to prepare her meals, provide afternoon tea and snacks, and attend to all sorts of duties. You will need to be her secretary and answering service. There are many responsibilities for you to learn. Mistress Lisa must be able to call on you for any and everything. And that also includes sex.
“In addition to all of those responsibilities will be your matronly duties. You will be expected to raise Mistress Lisa’s children. You will be their second mother.” Again Mistress Ann paused for effect.
Sam took a deep breath and muttered, “Raising kids. Being a mother? I have no idea how I can do that ma’am.”
Mistress Ann placed a warm hand on Sam’s knee and gave him a slight squeeze. “Don’t worry Samantha. When you leave here, you will know everything you need to know. How will you know? Let me give you an overview as to what your education is going to look like. We have been given 18 months to train you. That is how long it will take Mistress Lisa to earn her masters degree. When she graduates she wants you to be ready to serve her. So we must move with some urgency.
“Your stay will be split into 3 semesters of 6 months each — more or less. We must be flexible. In those 3 semesters we will take you from a 10 year old preadolescent to a mature woman of 23 or 24 years old.”
“Ten year old, ma’am?” Sam was confused.
“Yes Samantha. To be happy in your new life, to be comfortably adjusted to it, I have found that a boy needs a history. Just like a female wife has had years of training and indoctrination in her female life, you must also have a past to fall back on; something to rely on when difficult situations arise. Your feminine personality must be instinctive Samantha. And to be a proper mother, you must also understand what it was like to grow up as a little girl. You must know the children’s stories, the songs, the fairy tales. You need to know what it is like to dress and act and play like a little girl. It will be very useful and comforting to you later, plus it gives us a chronologic order to your training. Understand?”
“I think so. Yes ma’am.” It did make sense to Sam. He could see the usefulness of it. “But …” There was another question in Sam’s mind.
“Ssshhh,” Mistress Ann shushed him. “I know what you are thinking, and there is no cause for concern. This is not like those porno stereotypes that I am sure you have read about. It is not my intention to turn you into a sissy or humiliate you. And let me also point out one other concern that my young boys sometimes have. I do not use corporal punishment. I will never hurt you or humiliate you young Samantha. That is a promise. Ok?”
Sam felt relieved. “Yes ma’am. Thank you.”
“You are most welcome Samantha. During your first semester, and through all of your time here, you will have many different routines and learning experiences. But there is one thing that will remain consistent over the full 18 months. You will have ballet lessons every morning at 7:30 AM. It is excellent for teaching flexibility, posture, coordination and composure. And it will give you the training to step into ballroom dancing which is a must for any cultured young lady.
“Now, your second semester we will promote you to an adolescent girl. Along with makeup, hair and dressing styles you are going to learn about sex. It’s not what you think — well maybe a little. There is much more to sex than 101 positions. You will learn the age-old skills of flirting and seduction. You will learn to control boys and girls with sexual tension and possibilities. Yes, you will learn many sexual techniques, including some that you have never thought of. You will learn about bondage, S&M, sexual massage and other interesting procedures. And after intercourse, you will learn all about post-coitus techniques, how to emotionally extend your bonding, and how to perform during your pillow-talk.”
Gulp. “Ma’am, I don’t think Lisa is interested in those things.”
“Samantha, you must learn now that you will no longer refer to your mistress simply as Lisa. In private you will address her as Mistress Lisa. In public you will use Miss Lisa. And at all times you will say yes ma’am and no ma’am. Understand?”
“Thank you Samantha. To answer your question, Mistress Lisa might surprise you with her sexual preferences. But even if she is not interested in these items, some of the other Hawthornes might be. And remember, you must service anyone that your mistress gives you. So as you see, you must be prepared for all situations.”
“Also during your second semester you will work part time in a beauty salon. Hands on experience is the best way to learn hair care, makeup and all the cosmetic necessities of both being a pretty girl and servicing your mistress.
“Your third semester will see you reach slightly beyond your current age. As an early twenty something you will learn to become a mother. You will spend several hours each day working in the maternity ward of a hospital. You will learn to hold babies, change diapers, feed them and nurture them.
“So as you can see, you will be receiving a diverse and eclectic education aimed at helping you transition into a successful life as a wife and concubine. And of course along the way there will be many other items. In a matter of a few days I will stop speaking English with you. You will become conversant in French. And you will also begin your studies in political science. Miss Mona will send books for you to read and study. We will do a little traveling around France for your pleasure and diversion.
“That should cover your intellectual education. But there is also your physical transition. You will practice ballet and dancing, speaking and singing and such. In addition, every two months Dr. Ratchet will arrive for your facial peels. In fact, she will be here later this week for your second treatment. While she is here she will consult with a very talented plastic surgeon concerning facial feminization surgery for you. I know you will receive rhinoplasty to give you a smaller nose, but there might be another item or two. The two doctors will decide after they have examined you.
“And the final thing I want to discuss is your hormone therapy, which will start in about one month. Before we can start, you will need to donate sperm. Dr. Ratchet has already milked you a couple of times, but she would like more. So twice a week for the next couple of weeks, I will take you to a sperm bank for milking. When they have enough sperm, then we will begin you on your hormones. You will take two pills, one is an antiandrogen to counteract your testosterone. The other pill is progesterone to assist in the development of your breasts. Your estrogen you will receive by patch. By the end of our time together your breasts should be developing, your skin will be softening and you will have more curves and bigger hips. Your muscle mass will decrease and your arms, shoulders and legs will slim down to a more feminine shape.”
Mistress Ann stopped and settled back in her seat. She rested for a second and looked at Sam. “I know that is a lot to take in, but do you understand what we intend to accomplish? Do you have any questions Samantha?”
Sam thought for a moment then said, “No ma’am. I mean I have lots of little questions, but I understand the grand purpose and overall intentions for me.”
“That’s good Samantha. There are always lot’s of little questions, but let me help put some of your questions to rest. I have done this several times, and everything has always worked out great. As I said before, all of my ex-pupils keep in touch with. We share many ideas and discussions, but I assure you that every one of them is very happy in his new life.
“So now, I have just one last question for you Samantha. And it is a very important question. Now that you know our intentions for you, and you know what is expected of you for the rest of your life, do you want to do this? This is very important Samantha. You must be totally comfortable with what you have heard, and you must have no doubts about moving forward. Once we start, once I start devoting my time and resources to you, I do not want you to change your mind and quit on me. I do not want to waste my time or your time if you are not 100 percent certain and committed to your training Samantha.
“This will not be an easy 18 months. But it very well might be the best 18 months of your life. What do you say Samantha? I must know one way or another.”
Sam took a breath and nodded his head. “Yes ma’am, this is what I want. And I promise that I will work very hard and you will not be disappointed in me. I thank you and Mistress Lisa for this wonderful opportunity and I am ready to start as soon as you are.”
Mistress Ann gave Sam a big smile and patted him on his knee. “Very good Samantha. Then the first thing you need to do is say goodbye to your mistress. I will give you a minute of privacy.” Mistress Ann went into the other room and sent out Lisa. Mistress Ann watched on the monitor as Sam and Lisa embraced.
“I’m going to miss you,” Lisa sniffed.
“Me too. Will you come visit me?”
“Yes, but I don’t know when for sure. I’ll write to you.” They hugged and kissed as long as they could.
Their time was up as Mistress Ann stepped out of the back room. “Goodbye Miss Lisa,” she said to break up the pair. “Miss Samantha will write to you regularly.” Sam watched as Lisa walked out the door. A tear slid down his cheek.
Mistress Ann wouldn’t allow Sam to feel his temporary loss. She wrapped her arm around Sam’s shoulder and said, “Come, we need to get started.” She walked him down the hall and into a bedroom. There were two beds in the room. Both were canopied with one being a king size and the other being a single. “We will sleep and dress here, Samantha. This is my bed,” and she pointed to the king size. Moving over to the single bed she said, “And this is where you will sleep Samantha. Over the years I have found that it is best for us to share a room. We can bond quicker and I am closer to you to help you learn your day to day boudoir necessities.”
“The bath is there and I have already set you up with your toiletry needs. These dressers are empty now, but they will hold your clothes as we purchase them. Now, speaking of clothes it is time to change you into your new role. You are to be Samantha the ten year old. Please remove your clothes so I can see what we have to work with.”
Mistress Ann took a seat at a small vanity and writing desk. She pulled out a note pad, and a fabric tape measure from the center drawer. Crossing her legs she said, “Go ahead Samantha, remove everything.”
Sam was feeling self conscious, but Mistress Ann was going to be his tutor for the next year and a half. He was going to have to get used to their relationship sooner or later. Sam kicked off his shoes, then unbuttoned his dress and laid it on his bed. Mistress Ann smiled and encouraged Sam to continue. Sam continued, removing his slip, camisole and stockings, laying them carefully on his bed.
Sam was down to his lingerie. Mistress Ann said nothing, but encouraged him to continue. Sam reached behind his back and unfastened his pink brassiere, and laid it on his other clothes. Next he unlaced his corset and then his liner. He was left with his glued on breast forms and panties. Mistress Ann watched with keen interest as Sam slipped his manicured fingers inside the waist band of his panties and slid them down his smooth legs. As he straightened up he spread his legs and allowed his penis to swing free. He faced his mistress with his panties in one hand and his crumpled penis shriveled up and looking forlorn on his clean shaven crotch.
Mistress Ann smiled and stood. She walked over to Sam and held out her hand. Sam placed his panties in her hand. “You are looking very good Samantha. You have a nice start on your feminine body. You should be very proud of what you have accomplished so far. Your corset looks like it fits you well, but the rest of these clothes will no longer be needed.” She dropped Sam’s panties in the waste basket.
“You won’t be needing breasts, so please remove your forms.” The woman stood in front of Sam with her hand out, waiting for the breast forms. One by one Sam peeled them off and handed them to his mistress. To Sam’s astonishment and dismay, Mistress Ann tossed both forms into the trash.
“There is glue remover on the bath counter. Please go use it.” Mistress Ann followed Sam into the bathroom and watched as he removed his glue. Sam found it a little discomforting to have her watching him, but he was soon to discover that she intended to watch him all the time. It was her job to help him feminize his body and soul, and much to Sam’s chagrin that was a full time job.
When he was finished he was told to use the toilet. His mistress watched as he peed and shook his penis to shake off the last few drops.
“That is not how a lady finishes her toilet, Samantha. You will not manhandle your penis. Take a few squares of toilet paper and with one hand wrap the tissue over your penis and stroke the last drops out. Show me.” Sam did as he was told and his mistress watched him.
“A bit clumsy, but you have the idea. You just need more practice. Ok, please come with me.” Sam was stopped in front of the desk and told to stand there. Mistress Ann took her measuring tape and began measuring Sam’s anatomy. Like Dr. Ratchet, she measured everything from neck to ankles. The only thing she did not measure was Sam’s erect penis. But she did measure the length and circumference of his flaccid appendage. As she made her measurements she went down a list and wrote down the numbers and made little checks and notes.
“Comparing you to Dr. Ratchet’s last measurements it looks like you have put on a little weight, Samantha. That’s what good Parisian cooking will do for you. Please come here and step on the scale for me please.” Sam’s mistress weighed and recorded his weight.
“Well Samantha, we will need to reduce your weight, but we already knew that. I think your corset is a good fit for now, and it is very high quality. Please put it back on.”
After he was back in his corset, Mistress Ann inspected his fit and lacing. She made a few comments and suggestions, but all in all Sam had done an acceptable job. She then stepped into the closet and took out a small box. Removing the lid she pulled out some
rumba panties and handed them to Sam. “These are the style of panties that you will wear as a little boy. Do you like them?”
Sam had never seen such frilly panties and his first inclination was to consider them too frilly and too “young” for him. But then he realized that he was supposed to be dressing and acting like a young girl. “Yes, of course they are wonderful, ma’am.” he answered. Sam pulled them up his legs and reached inside to tuck his penis.
“Stop Samantha. You don’t have to tuck anymore. At least not until you reach adolescence.”
“Ma’am Samantha. Anytime you address me you will always use ma’am. Understood?” Mistress Ann did not raise her voice or emotions when she corrected Sam, she simply stated it as a parent would tell you the date.
“No Samantha you do not have to tuck. You can stop tucking for the next six months. Is that ok with you?”
“I thought it would be,” she said with a grin. Next she pulled a white full length slip from her box and handed it to Sam.
“Don’t I need to put on a bra first, ma’am?”
“Les petites jeune filles et garçons ne portent pas de brassiá¨res.”
“Little boys don’t wear brassieres, Samantha. You are going to become a little boy for the next six months. By then end of this semester you should have a start on nice little mounds. At that point you may start wearing a training brassiere. You are going to go through puberty both physically and chronologically Samantha. It will reinforce your new childhood as an effeminate boy.”
“Ma’am, I am to become an effeminate boy?”
Mistress Ann understood of course. Sam was worried about going in the wrong direction in his gender reassignment. “Yes Samantha. You are a boy; there is no doubt of that. But at the same time you are to dress and act like a little girl. When you begin to reach puberty we will feminize you; your appearance and lifestyle. But as a little boy without hormones or girlish attributes, you will just be an effeminate boy. Understand?”
“No ma’am, I am not sure.”
“Je ne comprend pas, ma’am.”
“I don’t understand, ma’am.”
“Exactly. That is how you say it in French. Repeat after me; Je ne comprend pas, ma’am.”
Sam did his best to imitate Mistress Ann. “Again. Again. Again.” Ten times she made Sam repeat the phrase. “I think it is a phrase that will be useful to you,” she said with a nice smile. Mistress Ann didn’t act or talk to Sam as a teacher would speak to a student. Instead, she sounded and acted more like a loving mother instructing her child.
“Let me explain it this way Samantha. We are making memories for you. I am sure that Sam has memories of his childhood as a boy; playing with friends and doing other things. And I suppose that at times these memories bring you comfort and pride in who and what you are. Am I correct?”
Sam picked up immediately and repeated, “Oui, ma’am.”
Mistress Ann smiled at Sam’s quick connection. “Well that is what we are doing here. We are making memories for the future you. You know who that is, don’t you Samantha?”
Sam caught her hint immediately. “Samantha, ma’am,” he proudly answered.
“Samantha the boy who feminized himself so that he could live his life as a girl, to be a bit more precise,” she answered back.
“But your memories have to be real and honest, Samantha. Otherwise they will provide you no comfort when you most need them. Understand?”
“Je comprend, ma’am. I understand ma’am.”
Sam repeated the phrase several times at Mistress Ann’s beckoning. “So your memories must be real and honest,” she reiterated. “In six months you will become a teenager. You will be into the start of your second puberty as your female hormones begin to take hold. Your nipples and breasts will become sensitive as they begin to blossom and grow. Your skin will become even softer and clearer. Muscle mass will begin to diminish and fat will relocate on your hips and buttocks. You will become softer, more curvaceous and buxom. You will become feminized Samantha.
“You are beginning as a boy dressing, acting and living as a girl. But you are not feminized now. You are an effeminate boy for the time being. That is what and who you are. Do you understand?”
Je comprend, ma’am.”
“Good, Samantha. And please notice that I used no derogatory terms to describe your current situation. I did not call you a sissy boy or describe you as prissy. I merely stated what you truly are. We are being honest, Samantha. There is no reason to be ashamed or sensitive to your situation. You are what you are and you are who you are. Do you see?”
“Oui. Je comprend, ma’am.”
Mistress Ann smiled and responded, “You are every bit as intelligent as I had been told Samantha. I am impressed. Please understand, to everyone else you will be a pretty little girl, but to us we will know that you are an effeminate boy learning to live life as a jeune fille. Now, please put on your slip.”
Mistress Ann handed Sam white stockings that came over his knees. Then she produced a pretty blue smock with cap sleeves and hem just below the knees. Over her blue dress, Mistress Ann placed a white apron that tied at the waist. And to finish his ensemble, Sam was given black patent shoes with 2 inch heels and a strap.
Sam looked very nice in his new clothes. Sam’s lack of not only breast forms but also his brassiere left him feeling odd — even a bit vulnerable. It was going to take Sam some time to psychologically accept the loss of his breast forms and bra. They had become an important component of Samantha the girl. The net effect was a younger looking Samantha. He was too big to pass for a preadolescent, but his lack of breasts made the appearance more reasonable.
“You look very nice young Samantha. Now come, we have an appointment for you at the beauty salon.”
“What about my makeup, ma’am?”
“Little boys do not wear makeup Samantha.”
A little sigh escaped Sam’s lips. He hadn’t expected this. It was going to be difficult changing from a beautiful and sophisticated woman into a little girl. He was feeling vulnerable and even a bit naked. “Yes, ma’am. If you would please hand me my purse I am ready to go.”
Mistress Ann smiled again and said, “Little boys do not need to carry a purse. What do you have to carry Samantha?”
Sam thought for a moment and replied, “Nothing ma’am. I am ready when you are.”
“Fine, then we shall leave. Please give me your hand and follow me. Whenever we leave the house I must always hold your hand. We can’t allow our young miss to wander off, now can we?”
“No ma’am.” And then Sam remembered that he didn’t have his purse — the purse he had carried as a big girl. He didn’t have his ID or passport or anything. He must have left it in the car. “Mistress Ann, I just realized that I left my real — I mean my previous purse in the car. I don’t have my ID or anything.”
“Not to worry Samantha dear, that was done on purpose. You will not need any identification while you are here.” Left unsaid was the true purpose. Neither Sam nor Samantha could run away. And no one else would be able to identify him.
Mistress Ann locked the front door then walked Sam to the salon. He felt very self conscious in public. Without his bra and breasts and makeup he felt totally wrong. He didn’t feel like a girl and he was worried other people could see that as well. He felt more like a boy dressing up as a girl; a little boy at that. Which is exactly how he was supposed to feel. Sam was now making memories of his earliest conversion from boy to girl.
The walk was short, not more than two blocks. They passed a few women who ignored the couple. As Mistress Ann opened the door to the salon, a little bell tinkled in a most quaint fashion. Sam took a deep breath and reveled in the wonderful smells. Sam was home. The pretty boy was hooked on salons.
“Mistress Ann, welcome,” a middle aged woman greeted them in French. “Is this pretty poppet your new boy?”
“Yes he is,” Mistress Ann said in English. “Samantha, would you please say hello to Madame Rupert. She will be your stylist today.” The two of them exchanged greetings, one in English and one in French. Madame Rupert understood both, but she had been instructed to speak only French to Samantha.
“Please come this way,” the stylist verbally instructed Sam, while she used her hands to indicate her wishes. With Sam sitting in his favorite chair, Madame Rupert asked Mistress Ann for instructions.
“Please remove young Samantha’s hair extensions and eyelashes. She will also need a manicure to a more age appropriate length. After we see her own hair let’s talk about her new style,” she said in English.
Madame Rupert swung Sam’s chair away from the mirror and facing towards a row of chairs. Mistress Ann took a seat directly in front of Sam and chatted with him as Madame Rupert first removed his eyelash extensions, and then his hair extensions. When she was finished, she swung the chair around so Sam could see his reflection in the mirror.
Sam almost began crying. All of his favorite and most important female traits were being stripped from him; first his bra and breasts and now his hair. His hair was SO short! Or so Sam believed. Actually it had grown over the last several weeks and was now long enough to cut into a short, female style. But that is not what Sam saw. He missed his long hair and curls. He looked liked a — gasp — boy! A boy under a salon cape. He had no makeup, no jewelry and now no hair. A tear slipped from his eye and rolled down his cheek.
Mistress Ann who was now standing beside him used her finger to wipe away the tear. “Do not worry Samantha. Madame Rupert will give you a nice appropriate style for a little girl. Now your own hair can grow out and you can enjoy the pride of growing into your feminization.” Turning to the French stylist she asked, “So Madame, what do you suggest for our disappointed little boy?”
“His hair is not that short. I can give him a pageboy. With his face I think it will look very cute and acceptable.”
“How about bangs?”
“They will be short, but they can grow out with his new style. Yes I think that would work for young Samantha.”
Mistress Ann switched to English and explained their conversation to Sam. “I think it will look very good for the image you are trying to project. You have the final say Samantha. Shall Madame Rupert proceed?”
With deep regrets over loosing his curly locks and older female appearance, Sam reluctantly responded, “Yes ma’am.”
Madame Rupert took Sam to the sink and washed and conditioned his hair. As sad as Sam was, he could at least take comfort in a routine that he not only felt comfortable with, but he enjoyed immensely. Sam did like being pampered in a salon.
After his washing, Madame Rupert made short work (sic) of cutting and styling his hair. She used her brush and hair dryer to turn the hair under and add more volume to it. When she was finished, he looked a bit more girly. Sam could take some satisfaction in that.
After finishing with Sam’s hair, Madame Rupert removed his nail polish and filed his nails down to a short length; boy length Sam thought. “I’m being turned back into a boy,” he thought to himself. This was not at all what he had expected. He had expected to be feminized even more. That is what he wanted. He didn’t want to go back to being a boy. That part of his life was behind him; at least he thought so. But now he was being remade as a boy. He looked more and more like a boy pretending to be a girl.
Upon the completion of Sam’s nails and hair, Mistress Ann signed for the work and again took Sam’s hand. “Say goodbye to Madame Rupert, Samantha.”
“Goodbye Madame Rupert.”
“Au revoir Samantha.”
Mistress Ann walked Sam outside and they turned down the street. “We are going to a dress maker Samantha. She will need to measure you so that she can finish some new clothes for you. I had to take a guess on the dress that you are wearing. Now we will get some clothes that fit properly.”
“Yes ma’am. Thank you ma’am,” Sam dutifully responded.
As they walked down the street, hand in hand, they again passed a few people, but no one said anything to or about Sam. They even passed another woman walking a young girl. The young girl was dressed in a frilly and lacy dress with petticoats underneath. The woman was holding the little girl’s hand, just like he and Mistress Ann.
One block away they turned into another quaint shop. All of the architecture in the neighborhood looked old and slightly dilapidated, and the dress shop was no different. Another bell tinkled as the mistress and her child entered. “Hello,” Mistress Ann called out.
“Back here,” a voice rang out in French. Mistress Ann led her young boy into the back.
“Bonjour Madame Longet.”
“Bonjour Madame Lange. Is this our new boy? He is very pretty.” Madame Longet was speaking in French just as she had been instructed.
“Samantha, please introduce yourself to Madame Longet.”
“Hello Madame Longet. I am Samantha.”
Mistress Ann handed a piece of paper to Madame Longet. Sam recognized the paper. It had all of Sam’ measurements on it. Madame Longet studied the paper and clucked several times. “Our little boy has put on some weight,” she told Mistress Ann. “Do you want me to dress him as is, or should I anticipate you removing his excess weight.” Her tone was just the tiniest bit snippy.
Mistress Ann heard the tone in Madame Longet’s voice and returned her attitude. “I shall have the weight off my boy in one week.”
Sam also could tell there was a little tension in the room, but he had no idea as to why. “Is everything ok, mistress?” he asked.
“Madame Longet is concerned that you have put on some weight, Samantha. I have assured her that you will loose it within the week.”
“I will ma’am. I promise.” Sam thought a second and added, “But mistress, I am wearing my corset and it is fully closed. So my size should be the same.”
Mistress Ann smiled at her young boy and explained, “You are thinking like a boy Samantha. It is not just your waist that is important. Extra weight shows up in your hips, your thighs and your arms.” Then she added some new information, “Miss Maggie thinks you look fine with a 26 inch waist. But I think you can reduce to a 24 inch waist. You are a small boy after all Samantha. I shall discuss it with Dr. Ratchet when she arrives.
“Now please step up on the pedestal so that Madame Longet can get a closer look at you.”
Before measuring Sam, Madame Longet had him remove his dress. She made a few measurements of her own, then began handing him dresses. He would try on the dress and Madame Longet would check a few items, and sometimes pin up a hem or collar. Sam tried on several frilly and lacy dresses.
After an hour at the dress shop, Mistress Ann and Samantha left for their next stop. “We need to stop at the ballet school and get you some tights and shoes for tomorrow.” They walked half a block and reached the school.
“It is convenient that everything is so close, ma’am”
“That is no coincidence young Samantha. This ten block area of Paris has served the rich and powerful for almost two hundred years. We have served royalty, premiers, the very rich and for an unfortunate time, even Nazis. Our work of transforming little boys into mature girls has been going on right here, invisible to our neighbors and the occasional tourists that wander through here.”
“Royalty have used your services, ma’am?”
Mistress Ann smiled at Samantha. “Yes my dear boy. We have even transformed a prince into a princess. Dukes, sons, heirs, nephews and even an enemy or two have received the benefit of our talents.”
“And no one knows that you are here?”
“Ma’am Samantha. Every time you speak to me I must hear either ma’am or mistress come out of your pretty lips.” Mistress Ann was very gentle in her admonishment.
“Some of the neighbors may suspect, but that is all they can do. We keep to our selves and we keep a very low profile. Over there is an elementary school with over 100 boys. But no one would ever suspect. And over there are their dormitories. They travel between buildings mostly through the interior courtyards, or in tunnels under the streets. We can move our students anywhere we want without having to come out on the public streets. All of these shops have back doors into our own private world.
“But once in a while, like today we might take to the public through ways. In fact, you have passed one or two boys. But we never acknowledge each other in public. We try to draw no attention to ourselves. So as you can guess, everything that we need to help you achieve your goal of becoming a beautiful concubine is right here in walking distance.”
“Wow, that’s neat.” And then he quickly added, “Ma’am.”
Mistress Ann bought Sam his ballet clothes then took him home. She pointed out the bakery, pharmacy, doctor’s office, and several other shops on the way back. Back in his new home, Mistress Ann took him to the kitchen where they cut up some fruit for a light snack. Then Sam was led upstairs to a “play room” that was filled with dolls and books.
There were many dolls, but Mistress Ann pointed out the Barbie dolls first. As Mistress Ann sat in a rocker she instructed Sam to bring over the Barbie doll.
“Please sit at my feet, Samantha. Now, you are going to be spending some time each morning here in the play room. You will begin by dressing Barbie and her friend Ken. Only I think we will call them Lisa and Samantha. How does that sound?”
“I will tell you what dress to put on Barbie, and then it will be your job to accessorize her. And after Lisa is dressed, then you will have to dress Samantha. Now it is important that you dress Samantha to compliment Lisa and not clash with her. This game is designed to teach you fashion sense. But it is not a child’s game, Samantha. All of the dresses have been made by Madame Longet. They are made from various fabrics and they are made exactly as their full size counter parts. You will learn about fabrics, jewelry, shoes and accessories in this game.
“Later, you will handle the larger dolls, learning how to handle them as if they were real babies. Also in this room you and I will read teen magazines and fashion magazines and even some of the popular celebrity magazines. They will all be in French so you can practice your language lessons while looking at current fashions and makeup and even reading some articles on dating, relationships, boys and girls and all the things that a modern girl needs to be aware of.
“How does that sound, Samantha?”
“Good. Then shall we begin dressing Lisa?” For the next hour Sam would pick out dresses and bring them back to his spot on the floor. He would sit in front of Mistress Ann as she rocked to and fro, and dress his dolls, following the advice and comments of his mistress.
In mid afternoon they took a break, “Time for tea, Samantha.” Mistress Ann led Sam to the kitchen where she put some water in a tea kettle and set it on the stove. “Once Madame Longet finishes your new clothes, you will be expected to make tea while dressed in a maid uniform. Whenever you are performing domestic duties you will dress as a domestic. Do you understand?”
“Yes ma’am. When I help Miss Maggie we both change into our maid uniform.”
“I am happy to hear that Miss Maggie is still following the lessons I taught her.”
“You taught Miss Maggie? She studied here also?”
“Ma’am Samantha, ma’am. If it makes it easier for you, always start your sentence with ma’am. It might help you remember.”
“Yes Samantha, Miss Maggie was one of my first private boys.”
“Ma’am? Private boys?”
Mistress Ann carried the tea kettle to a table already set for their afternoon tea. As they sipped their tea Mistress Ann explained a few things to Sam. “I mentioned earlier that this little neighborhood has been here for a couple hundred years. We have been transforming little boys into pretty girls for the rich and affluent for all that time. But we do it primarily through our schools. We have an excellent primary and prep school here. We operate all year long, although some boys return home for summer vacation.
“We have a very high teacher to boy ratio. That is important when you are guiding young boys around the clock. Believe it or not, without full time supervision little boys, even little boys dressed in fine silk, tend to become mischievous,” she grinned at Sam. Sam enjoyed the humor and returned her grin. “That is where most of our tutors are employed. But those are also the lowest paying jobs. Don’t get me wrong Samantha, the teachers are still paid very well. Very well indeed compared to other teachers. Like I said, we cater to the rich and powerful.
“To increase one’s income, some of the more enterprising matrons open their own shops to cater to our community. The locals also peruse our shops, but the primary customers come from our little community. But the most highly paid matrons are the ones that take a single boy and provide full time transformation guidance. It is a very time intensive job. You and I will live together for 24 hours a day for 18 months.
“This is not a career for everyone. First you have to have the temperament and desire, and you must be very knowledgeable of your craft. And second you must love what you do. Samantha, I love my job. I adore pretty boys and I love turning them into confident and consummate women. The best part of my job is watching you grow into your new life. And the proudest day of my life is the day that you graduate and I return you to Miss Lisa.
“But that will also be a sad day for me. I will miss you Samantha. I will miss having you live with. That is why I am always so happy to hear from my past students. And I am also proud when I hear that my students are doing well and remembering their lessons. I am truly happy to hear that you and Miss Maggie still follow her lessons so many years later.”
“Ma’am, how many students have you taught?”
Mistress Ann laughed. “Samantha, you are trying to guess as to hold old I am. You are a little vamp! I will save you the trouble, I am in my sixties.”
“Ma’am, you are very pretty and I would not have guessed your age. But I truly am interested in your other students. Who were they and how have they fared in their new lives.” Sam paused for a second and then added, “Are they all happy with their decision?”
Mistress Ann reached across the table and took Sam’s hand. While holding his hand she looked into his eyes. “You have nothing to fear young Samantha. I have taught many boys, including most of Miss Grace’s sons, grandsons and concubines. I am the highest paid matron in our community Samantha. And the reason is because I am the best. I say that not to brag, but to reassure you. And I also want to assure you, every boy is now immensely happy.”
Sam smiled and asked, “Ma’am, was Miss Maggie a good student?”
Mistress Ann chuckled. Samantha could sense the memories that Mistress Ann was pulling up. “Yes he was. Maggie knew early in life what he wanted. Sort of like you. But he was much more confident at a much earlier age. Miss Mona often laments the fact that she didn’t have to chase Maggie to convince him to become a girly concubine. Miss Maggie constantly wanted to move faster than I would allow him. He was like the teenage girl that wants to be twenty, and sneaks around behind her mother’s back, wearing makeup at too young an age.
“And Maggie was without a doubt the best cook I have ever had. She went on to culinary school after she left me.”
Samantha smiled. “I like Miss Maggie. Did you have any other interesting students, ma’am?”
“All of my students were interesting. And all of them were my favorite. But they were all different, Samantha.”
“Who was the prettiest, ma’am?”
“You are one for questions, aren’t you young Samantha? This is your last question, then you must go study. All of my boys grew up to be beautiful girls. But far and away the most beautiful girl I have ever had was someone you know; Gisela. Even as a boy he was beautiful. The first day I put him in a dress he radiated beauty and sophistication. The other matrons constantly commented on his beauty. And once his hormones kicked in, once he truly began transforming into his feminized body, he became a stunning beauty. After reaching her “teen” years, wherever she went she was the center of attention.
“And you dear Samantha have all the earmarks of being the same. I see so much potential in you that I am constantly reminded of Gisela. And you are why I continue to take new boys. Because every once in a while a true gem falls into my lap. And I love gems, Samantha.
“Now, you need to clean up the dishes.”
Mistress Ann brought Sam back to the last room in the house. It had at one time been a small bedroom, but now it was as a study. It had a couple of easy chairs with floor lamps behind each. There was a large desk with another lamp, and sitting on the desk was a book.
“Each afternoon you will study until 5:30. Miss Mona has sent me a few books for you to begin reading. This is your first assignment Samantha,” and she handed the book to Sam. Mistress Ann took a seat in one of the easy chairs and picked up a hard bound book. Before opening her book, she watched Sam as he settled in at the desk.
Sam set the book in front of him and looked at the title; “When in the Course of Human Events- Arguing the Case for Southern Session” by Charles Adams. “Exactly what I would have expected from Miss Mona,” Sam thought to himself. “Well Miss Mona, I will read this book, I will absorb it and I will memorize. And I will read all of your books and I will talk your talk to the day Mistress Lisa is elected President. But on that day, you will find a wolf in sheep’s clothing. I will honor my promise to Miss Harriet, and I will not financially hurt your family. But I will make Lisa the most compassionate and progressive president our nation has ever seen. Samantha may be building new memories for herself, but Sam shall never forget where he came from. I once promised my mother that I would make things better when I grew up, and now I have been given that opportunity. I will not fail her.” Sam opened the book and began reading. He fully intended to become the smartest and best campaign manager in the history of his nation. Samantha Springer (his “public” name) would be a phenom.
At 5:50 Mistress Ann closed her book and told Sam to pick an appropriate point to stop his reading. “Time to prepare dinner,” she told her effeminate boy. “Normally you would have on your maid uniform, but tonight you will have to settle for an apron.”
Their meal was meager, but tasty. Mistress Ann was going to make sure that Sam lost that extra weight. After cleaning the table and dishes, Sam was taken back to their bedroom. “It is time to prepare for bed young Samantha. When you are finished here, we will watch a movie then retire for the evening. Now the first thing I would like you to do is undress and remove your corset.”
Sam removed his clothes and placed them where Mistress Ann instructed. When he was totally stripped Mistress Ann said, “I understand that you use sit ups to keep your abdominal muscles firm. I think you will find ballet is even better, but this is a good habit for you. You won’t always be practicing ballet. So please show me what you do.”
Mistress Ann watched him do only ten sit ups and she stopped him. “You’re being sloppy Samantha. You know how to do better sit ups. Slow down and make sure you go all the way from flat on your back to stretching your abdomen as far as you can go and then returning to your prone position. Slow and deliberate is the best technique Samantha. Now start over.”
When he was finished Mistress Ann said, “Better. To the bathroom and prepare your bath.”
While the tub was filling Mistress Ann showed Sam where all of his toiletries were located. “Floss and brush your teeth.” By the time Sam was finished the tub was full. “In you go dear. Ten minutes and ten minutes only. Any longer and you will begin to loose precious skin oils. Any less and you will not be able to fully absorb the emollients.”
Mistress Ann sat in a chair and watched Sam as he enjoyed his bath. With one minute left she said, “Use the shampoo and wash your hair. Then use the crá¨me rinse.”
When young Samantha was finished Mistress Ann showed him how to wrap a towel around his hair and another around his torso. “You will wash and set your hair every other night. Now here are the cleansers that Dr. Ratchet has recommended for your skin, please go ahead and apply them.” Once again Mistress Ann watched Sam go through his nightly routine.
When Sam was finished, Mistress Ann took the boy back to the vanity and had him sit in front of the mirror. She handed him a brush and told him to brush out his wet hair. “Now I will show you how to set your hair. I will put in the first curler, and then you can try.” Sam’s hair was short, so Mistress Ann had him use her smallest curlers. Plus, she also wanted as many curlers as possible in Sam’s hair for the evening. Mistress Ann patiently worked with Sam teaching him how best to set his hair for sleeping on curlers. There was a technique to everything she told him. When they were both satisfied with Sam’s set, he placed a hair net and scarf over his curlers.
“Put your corset back on, Samantha.” When comfortably strapped into his corset, Sam was given a set of pink, silk pajamas for his evening wear. He put a light silk robe over his pajamas, stepped into a pair of fuzzy slippers and returned the towels to their proper place in the bath room. He glanced in the mirror and thought he looked a little more feminine with the curlers in his hair. But his pajamas, robe and slippers looked childish on him. And without his breasts, he thought he looked even more like a child; like a little boy dressing in his sister’s clothes. Sam preferred his old look when he was with Lisa. He was pretty and very convincing then. He missed his boobs and curly hair. And he missed Lisa.
Sam was ready for his evening entertainment. Mistress Ann returned to the front parlor and slid a disc into the DVD player. “We are going to be watching a lot of movies, Samantha. We will start with movies appropriate for a little girl, and later we will move into romance and date movies. For the first couple of weeks you will need to become familiar with the Disney princess classics. So tonight we will start with Sleeping Beauty.” The movie was in French with English subtitles. Over the next several weeks Sam would see all the princess movies several times, before Mistress Ann removed the subtitles and they watched the movies again. Mistress Ann would stop the non-subtitled movies and quiz Samantha on what had been said. These movies, along with nursery rhyme singing, would be a key component to Sam’s early French lessons, and his indoctrination into the life and mind set of a little girl.
At the end of the movie they moved back to the bedroom. “Samantha, you will now remove my clothing.” Sam’s eye got large and his mistress giggled. She knew exactly what he was thinking. “No Samantha we are not going to have sex. And I apologize for not being as attractive as your Miss Lisa. But one of your duties as Miss Lisa’s handmaiden will be to help prepare her for bed. So you get to practice on me. As you remove each article of clothing you need to lay it on the bed. After you have helped me into my negligee I will go the bathroom and you will then put the clothes in their proper place. When finished, turn down my bed and stand by it until I return.
“Yes ma’am.” Sam was surprised by Mistress Ann. When he had removed all of her clothes he found her to be in remarkably good shape … for someone her age that is. Her figure was still shapely and she had not added much fat. Her breasts looked firm and did not sag, and her skin was still soft with no wrinkles. Her muscles looked toned and Sam saw no flab on her. He was impressed and wondered how she managed to still look so good. He would find out the next morning at the ballet school.
Mistress Ann returned after completing her nightly routine and slipped into bed. “You are to pull the duvet over me, wish me goodnight, turn out the light and go to bed,” she told Sam. Sam followed her instructions and crawled into his own bed. The bed was softer than he had expected, and it squeaked every time he moved. The squeaks were there on purpose. It would be difficult for Sam to do anything without Mistress Ann hearing.
Both laid awake thinking about the other. Each was happy with her new partner.
The next day began with the radio alarm turning on and playing soft music. Mistress Ann rolled over in her large bed and pushed the duvet off her. She slipped on a pair slippers and a robe. “Samantha, time to rise and shine. Please come with me.”
Sam rubbed his eyes and stretched. He followed his mistress into the bathroom and waited for his instructions. “Please use the toilet first.” Sam did as he was told. When he was finished he wiped his penis as he had been taught. “Move to the bidet and make sure to wash your bottom Samantha.”
Afterwards, Sam brushed and flossed, put on his deodorant, washed his face and moisturized with Dr. Ratchet’s prescription solution and went about his normal routine. Mistress Ann watched and made only a few comments. They returned to the bedroom for dressing. “Normally you will put on a maid uniform, but today we have only one dress for you to wear. Here is a pair of fresh panties, start with them.” Mistress Ann handed Sam another pair of frilly rumba panties.
Sam felt a little silly sliding the panties up his smooth legs, but he understood the reason for them. Mistress Ann watched Sam finish dressing. “Now over to your vanity and remove your curlers.” Sam took a seat and removed his scarf and hair net. Then he began unrolling the curlers one by one, dropping them into a little bucket. The pins went in a shallow dish with a hinged cover. When he had removed the last curler, he was handed a brush and told to brush out his hair.
Mistress Ann handed Sam a pair of pink barrettes. “These are popular with the girls now. Slip one on each side to hold your hair back from your face.” Sam put them in his hair and Mistress Ann said, “There, now you look like a little girl. Next, each morning you will go prepare a bath for me. Let me show you which bath beads I would like you to use for me. Then you will come get me from my bed.”
When her bath was ready she instructed Sam to help her undress. “I’ll show you where to put my clothes after my bath,” she said as she slipped into the warm water. “Samantha, take that soap and lather the loofah, then you can begin washing me. Start with my feet and move up each leg.” Sam felt a little odd washing his mistress, but he knew it was a duty he would have to perform. It was just that … that she was so much older than him. This would have been easy with Lisa, but Mistress Ann was different. It was like becoming intimate with his grandmother. It just felt odd is all. He eventually got over it.
Mistress Ann guided Sam through the rest of her bath. She lifted her leg and placed it on the side of the tub. “Lather my leg, and then I want you to shave it, Samantha. There is a razor in the top drawer.”
Sam retrieved the razor, but before he lathered her leg he said, “Ma’am your leg doesn’t need shaving. There is no hair on it.”
“I know Samantha. This is practice. Please begin.” Sam shaved both legs for his mistress and he didn’t knick her once. “Good work, young Samantha,” she said as she stepped out of the bath. Please hand me one towel and use another to begin drying me.” Mistress Ann wrapped her towel around her breasts, then raised it so Sam could towel off her tummy. She held out her arms for Sam to dry, and then she turned, allowing him to dry her shoulders and back. “Very good Samantha. Now please wait here while I finish my morning toilet.”
Sam watched as the older woman used the toilet and bidet. “See how it is done?”
Mistress Ann brushed her teeth, and spread moisturizer over her face. She handed the jar to Sam and dropped her towel. Please moisturize my skin from neck to feet Samantha. Don’t use too much.”
Sam gulped. Spreading the moisturizer on her back and arms and legs was going to be no problem. But on her breasts and ass … that was going to be awkward. His mistress smiled at him, knowing full well what was going through his mind. She said nothing as Sam began. Sam started with her back and shoulders, then moved to her arms. She turned to him and presented her chest to him.
Sam very tentatively spread the silky cream over the top of her left breast. Mistress Ann took his hand and held it over her breast. “Samantha, I know this might feel a little awkward to you, but you are to be my handmaiden. As a handmaiden you must consider my body to be your body. You must be perfectly comfortable around me so that you can serve me properly. You would never spread moisturizer over your breasts in such a sensitive and tentative manner. This is not sexual; even though you are a boy and I am a girl. We are both girls now. Please start again.”
“Yes ma’am.” Sam listened to her and he tried, but this would definitely take some getting used to. Mistress Ann knew that also. Sam finished his assignment and then followed his mistress back into the bedroom. My panties and bras are in the top drawer. Please bring me a matching pair and help me put them on.
Sam picked out a pale blue set and returned to his mistress. He knelt on the floor and held the panties for her to step into them. He slid them up her legs and snugged them on her hips. Then he held the bra by its straps so she could put her arms through. Mistress Ann immediately turned around and let Sam clasp the bra.
“Camisoles are in the second drawer, please pick out a matching cami.” Sam helped her slide it over her head. “In my closet is a white sun dress. Please bring it to me.” When Sam opened her closet he saw dozens and dozens of dresses. He guessed as to the one she wanted and held it up for her to confirm. “No, keep going.”
On his second attempt Sam picked the correct dress. He then helped Mistress Ann step into it, and he buttoned the back and tied a sash around her waist. “I would like to wear open toed, beige sandals, Samantha. Please bring them to me.” Sam again went into the closet and picked up what he thought were the right shoes. “Good boy Samantha. Please bring them to me.” Sam placed them on the floor and she stepped into them.”
“Very good Samantha. Now you shall make the beds.” Mistress Ann took him step by step through the proper procedure to make their beds. After they had made the beds and cleaned up around the room Mistress Ann said, “We shall go get some juice and a bit of toast. Please follow behind me.”
In the kitchen Mistress Ann talked Samantha through preparing their meager breakfast. They would have a better breakfast after ballet lessons. Sam cleaned up the kitchen and was told, “Normally you would return to your room to change out of your maid uniform and into today’s dress. But that is not necessary today. Let’s go to your ballet lessons, Samantha.”
Mistress Ann took Sam’s hand and led him down the street to the ballet school. There was an electronic pad on the door, and Mistress Ann keyed in the password. There was only one light in the entry as they walked to the back of the room where they entered a door that said “Filles”. Mistress Ann flipped on a light switch and Sam saw a room lined with lockers. On each locker was a name. Mistress Ann knew right where to go. One locker said M. Ann and the adjoining locker said M. Samantha. Mistress removed a key from her purse and opened both lockers.
Inside Sam found the tights and shoes they bought the previous day. “Please change into your ballet clothes Samantha.” Included was a corset, but the fabric looked more supple and thinner than Sam’s corset. Sam removed his clothes down to his corset. “Corset too Samantha, but leave on your liner. The ballet corset is much more pliable for you.”
Both girls changed clothes and put on their ballet shoes. Mistress Ann locked their lockers then pointed out the necessity room. They returned to the gym and found all of the lights on and Madame Piaget doing some stretching exercises. Mistress Ann pointed Sam to a bench, then went to join Madame Piaget. Sam sat on the bench and watched the two women limber up. Sam suddenly realized how his mistress kept in such fine shape.
While he was waiting, girls started filtering in through a rear door. They all said, “Bonjour Madame Piaget,” as they filed in, then they glanced at Sam. Some smiled, some giggled and some merely ignored him as they went into the locker room to change. A few minutes later they returned from the locker room in groups of two and three girls. They were talking and joking with each other. They looked at Sam but again said nothing.
Madame Piaget finished her exercises and waited for the remaining girls to arrive. When 15 girls had arrived she clapped her hands. The playful girls turned their attention and listened to a short speech by Madame Piaget. Sam heard his name two or three times. While they were listening to their teacher, Sam was studying the girls. They were about 13 or 14 and all were very lithe and pretty. They had the curves and small breasts of teenagers.
Madame Piaget finished her speech and one by one the girls walked to Sam. Each girl did a small curtsey and said, “Mon nom est Suzanne,” and “Mon nom est Francoise,” and “Mon nom est Karin,” and all the way through the entire group of 15 girls. Each girl gave Sam a polite smile and seemed to be very nice. Madame Piaget gave some additional instructions and all of the girls ran out on the floor. She pointed to a spot for Sam, and he also took a seat on the floor.
Mistress Ann said in English, “Follow Madame Piaget, Samantha.” Then she walked over to rail and began stretching. Sam half watched his mistress and half followed Madame Piaget as she led them through their stretching exercises. Sam was intrigued and impressed with his mistress’s abilities. He became so engrossed in watching her that the next thing he heard was clapping hands. He turned to Madame Piaget and she was giving him a stern look. She spoke in French and pointed to her eyes. The girls around the room giggled as Sam was properly chastised. He turned his complete attention to his teacher.
As the lessons moved along Sam was embarrassed as to how much better the girls were than he. He could be barely do some of the moves they all managed to accomplish with ease and flair. When they took turns and Sam would miss a move, some of the girls would giggle. Sam would turn red and Mistress Ann would smile.
About 90 minutes later Madame Piaget released the class. The girls all went running and jumping into the locker room to change clothes. Mistress Ann called Sam over to a chair next to her. “We will let the boys all change before we do like wise. They have to move rather fast to get to their next class. So how did you like your first lesson?”
But Sam didn’t hear her question. His attention stopped at the word boys. “Those were all boys, ma’am?”
Mistress smiled at her young boy. “Yes, of course Samantha. They are just like you, only a little younger. What did you think?” She knew the answer.
“Wow. I thought they were all girls, ma’am. They looked so pretty and so … good at ballet. They way they moved was just like a real girl.”
“And that is why you are here, Samantha. Ballet will do that for you also. In no time at all you will be moving with their grace and balance.”
“I hope so ma’am. They were all very graceful.”
The boys began leaving the locker room, dressed in their pretty school uniforms of blouses, skirts and knee socks. Some waved at Sam as they left. In the locker room, they donned shower caps and took a quick rinse in the showers, then changed back into their street clothes. Mistress Ann walked Sam home to his next lesson of the day.
“With tightlacing it is important to not only watch what you eat, but how much and when. It is best to eat a small amount every two or three hours. After your ballet lessons each day we have our “big” breakfast.” The “big” breakfast wasn’t all that big. Sam was instructed to prepare cereal, fruit and milk. Later, when Sam had reached his weight target, Mistress Ann would add a few strips of bacon. But that was still weeks away.
After breakfast they went to the playroom. Sam and Mistress Ann played with the “Lisa” and “Samantha” dolls, dressing and undressing them several times. Mistress kept up a constant dialog explaining fashion and fabric details. After dolls they moved onto a children’s book for teaching French. And for the last half hour they flipped through a teen magazine. They sat side by side and Mistress Ann would read a sentence first, Sam would read it several times with Mistress Ann correcting his pronunciation, then she would translate for Sam.
After reading, Sam was introduced to French poems and children’s songs. “Singing is one of the best methods in the world to teach language and to help with your voice. Singing is ballet for the voice,” she said. “We will stretch your vocal cords so you can raise your voice to a soprano. Today we start with an icon, young Samantha; Frá¨re Jacque.”
By the time they were done with dolls, and reading and singing it was noon, and time for another meal. It was another smallish meal, but all of the “nibbling” left Samantha feeling satisfied. Sam handled the cooking and cleaning chores, while Mistress Ann instructed him through the routine step by step.
They had almost two hours until their next obligation, so Sam was told to return to his homework. At 2:30 Mistress Ann took Sam’s soft hand and walked him to Madame Longet’s where he tried on his new dresses. He was given a very wide selection of dresses; everything from a school uniform to frilly, petticoated dresses to maid uniforms. He must have tried on fifteen different dresses and Madame Longet had at least another ten already started.
“You did all of this since yesterday?” Sam asked in amazement.
“Heavens no,” Mistress Ann answered. “Madame Longet has been working on these for almost a month.”
“A month ma’am? But I only agreed to come here last week.”
Mistress Ann smiled and stroked Sam’s hair. “Maybe so, but I have been anticipating you for over a month now. Miss Maggie had a feeling about you long ago. I have been following your progress with much anticipation young Samantha.”
Sam felt awkward trying on the dresses. He felt that some of them were very girlish and juvenile. They had too much lace and frills and embroidery and petticoats and they made him look very childish and immature, (which was the intent of Mistress Ann). His short hair and lack of makeup and breasts didn’t help. Mistress Ann had said she wouldn’t humiliate him, but he felt … prissy wearing these dresses.
And to make matters worse, Mistress Ann was taking pictures of him as he tried on the dresses. “Big smile Samantha dear,” she would say as she used Madame Longet’s camera to take Sam’s picture. “These will be sent to Mistress Lisa so she can follow your progress.”
“Yuck,” he thought. “She’s going to think I look like a sissy. Can I look any worse than this?” Actually, by the time he reached “puberty” his hair would be longer and he would be wearing pig tails as well. And if not pigtails, he would have pretty pink bows and ribbons tied in his hair. Sam was going to feel much more sissified before his first semester came to a close.
Madame Longet kept several of the dresses for final adjustments, but she wrapped 8 outfits for Samantha and Mistress Ann to carry home with them. After leaving the shop Samantha realized that they had not paid. “Does Madame Longet just charge you, ma’am?”
“That’s correct Samantha.”
“Were these very expensive, ma’am?”
“Are you worried about the money?” she asked with a smile.
“No ma’am, of course not. I am just curious is all.”
“Yes, handmade dresses are very expensive. Each dress is probably around 1000 Euros.”
“That is expensive, ma’am.”
“But you deserve the best, right?”
“There are a number of extenuating reasons for the high price. It’s not just Madame Longet’s labor and materials; we also have a local Guild tax.”
“Our little community has some very expensive needs. The tunnels under the road that I mentioned yesterday, we paid for ourselves. Their knowledge is limited strictly to our Guild. And we must purchase special favors from certain politicians to keep our existence quiet. Plus we have some very expensive security requirements. All of those expenses are paid by our Guild. So as you can see, we need extra money to cover those items.”
“You have a Guild, ma’am?”
“Yes Samantha. Everyone involved in the business of transforming special boys such as yourself must belong to the Guild. Background checks are required of course, and proper training is needed. We have some very important boys here and we must take all precautions to make sure that their identity and safety are never compromised. Plus we must maintain the highest levels of quality and expertise. You and your fellow students are very valuable merchandise, Samantha.”
“What is the name of your Guild, ma’am?”
“It is a very old Guild Samantha dear, and the name is actually in Latin. It basically means matrons of boys to girls.”
“And you are a member, ma’am?”
“Of course. Everyone that works with our community must be a Guild member.”
“Do you have to pay the Guild Tax also, ma’am?”
“Certainly my dear, I pay the most.”
“The most? Why ma’am?”
“Because I am the best at what I do, so I make the most money. I do not work for the school, my little muffin. I am an independent. I take on one boy at a time and give him very special and individualized training. That type of training is much more expensive than the other boys receive.”
With a little pride in his voice Sam asked, “So you are the best?”
“But of course Samantha. You don’t think Mistress Lisa or Miss Maggie would let you settle for second best, do you?”
Sam grinned and agreed, “I am sure they wouldn’t, ma’am.”
When they reached home Sam put away most of his new clothes. It was time for tea, so Mistress Ann instructed him to change into a maid uniform. After tea it was time for studying. While Sam sat at his desk reading, Mistress Ann excused herself for a moment. She returned with a lap top computer that she sat on Sam’s desk. Sliding the memory card into the computer she then showed Sam the pictures that she had taken.
Sam’s worst fears were confirmed; he did look like a sissy boy. His short hair and no makeup made him look like a boy wearing a dress. He no longer looked like the beautiful Samantha he had once been. “What are you going to do with the pictures, ma’am?”
“I told you Samantha. Mistress Lisa has asked for weekly pictures to keep up with your transformation. I will send these to her. But I wanted you to see them also. I want you to see how pretty you look.”
“I look like a prissy boy, ma’am.”
“No you do not, Samantha. You look like a pretty young child. A female child or course.”
“I don’t feel like a female child, ma’am. With this short hair, and no make up and being flat-chested and all, I look like a boy. I can’t wait until I can grow my hair longer and start my hormones. I want to look like a real girl. I can’t wait until next semester when I can become a teenager and start wearing makeup.”
“How astute of you Samantha. You can’t wait to “grow up”. That is exactly what I want you to feel. That is what childhood is about. It is about the anticipation and yearning and eagerness to grow up and become a beautiful adult woman. Those are some of the strongest memories you will have. Anticipation is half the fun, although right now you might not think so. But the ability to practice with your hair and make up is one of the fun memories you will have. Playing dress up is something every little girl goes through and those are the memories that you will cherish.
“And of course going through puberty is another of those most cherished memories. Growing your breasts and trying on your first training bra is something you will never forget. These are the memories that will give you sustenance and strength throughout your adult life.”
Mistress Ann paused for affect and finished, “These are the things that will help you become a successful wife and concubine for Mistress Lisa.”
“Yes ma’am,” Sam responded.
Sam finished his study time, and since he was still in his maid uniform, Mistress Ann took him to the kitchen. Sam received another cooking lesson from Mistress Ann. At the dinner table Sam had some additional questions abut the Guild.
“Ma’am, you said that the Guild has to pay off politicians. Why?”
“My dear Samantha, for a little girl you have lots of questions. Why do you want to know about these complicated grown up things?”
Sam thought his mistress was talking down to him like a little boy, but then he realized the truth. He was supposed to be a little girl and she was merely playing the role. At least he thought that was the situation, so he decided to play along.
“Ma’am, when I grow up I want to become involved in politics, so I want to understand as much as possible about the grown up world.”
Mistress Ann obviously approved of Sam’s role playing and she showed it with a large smile and wink. “Of course, I understand, Samantha. Well you see my little girl, there are many things that the government has to do. The fire department has to inspect your commercial buildings to make sure they are safe from fire. And the building code people want to inspect your buildings to make sure they are safe from electrical and plumbing and building hazards. And the same goes for water and sewer and police. All of these people and departments are charged by law to make inspections and ensure the public safety. And this is especially important when you have a school filled with young children.
“Do you understand so far?”
“Yes ma’am. You don’t want these people coming into your school, do you?”
“Absolutely not young Samantha. You catch on very quickly. They might even find out about secret tunnels under the streets. But the most important reason is that the Guild can not take a chance on the bureaucrats finding out what our true mission is. The chances are not that high that a street worker might identify one of our little girls as the boy he really is. But we are charged with the safety and secrecy of our boys. Very rich and powerful people are depending upon us. So we can afford to take no chances at all.”
“So how do you keep them out, ma’am?”
“Bribes sweet Samantha; carefully placed bribes to high placed officials. And you must understand the difficulty of doing this, without raising too much suspicion. We can’t just walk up to the mayor and hand him money and then ask him to ignore our little business. We must be much more delicate than that.”
“Please ma’am, can you tell me how you do it. Someday I expect to be in situations like this, or at least I need to know how these things are done.”
Mistress Ann was puzzled with Sam’s curiosity. She knew much about the Hawthornes, but there was also much she was not privy too. For instance, Mistress Ann had no idea concerning Hawthorne activities in the political and lobbying arenas. And there was no way that she could be aware of Lisa’s presidential aspirations, or her intended use of Samantha as a public aide. But Miss Mona was training the boy in politics, so she decided to give him some information.
“Samantha honey, I cannot tell you too much. Our Guild survives on keeping our secrets. But I will give you an overview. These are delicate matters and one of the most important aspects is that you must allow all parties to plead ignorance if they must. To do that you must use an intermediary. A lawyer or clergy man acting as a go between allows both parties to disavow direct contact with each other. Politicians always need this excuse. You must do nothing in writing and money must be untraceable or appear to be perfectly legitimate.”
“Ma’am, I understand this is sensitive, but this is the type of business I will be involved in when I am older. Can you tell me a little more?”
Now Mistress Ann was surprised. “Samantha, you intend to do these things when you grow up? Really?”
Now it was Sam’s turn to play coy. “Yes ma’am. My reading and assignments from Miss Mona are to prepare me to enter the world of Washington politics.”
Mistress Ann hesitated for a moment, thinking about whom she was tutoring and who was sponsoring him. She knew Sam’s sponsors were rich and trust worthy. “Samantha my little boy, I share this with you because of Miss Maggie. She has vouched for you. But you must never tell another soul.”
“I will tell no one, ma’am. This is background information for me and me alone.”
“Several officials must be approached. And you must use a very legitimate messenger. We have a priest we can trust. Without giving away any information as to our true mission, he explains our ability to assure the safety of our very rich students. And he explains that if the official will trust him, he can arrange for a very large and very legal political donation to be made by a rich supporter. It sounds simple but the priest is an expert at manipulating people.”
“Thank you ma’am. I appreciate your explanation.”
After dinner Sam prepared for bed and then watched another movie in French with English subtitles.
Wednesday’s activities followed the previous day’s until the afternoon. After lunch, they visited the doctor’s office. There were two doctors waiting for Sam. He knew Dr. Ratchet, but Dr. Bethune was new to Sam. “Dr. Bethune will be performing your plastic surgery,” Dr. Ratchet explained. “She is one of the foremost experts on feminization surgery. No one in the world has performed as many surgeries on teens as she has. Her expertise with young males is unmatched.”
The four of them went to a large examination room where Sam was told to remove all of his clothes. He was given another thorough examination where everything was measured.
“You’ve gained a little weight while you were in Paris,” Dr. Ratchet mentioned as she noted his weight on his chart.
“Don’t worry doctor, he’ll drop that weight in no time.” Mistress Ann interjected. “But might I ask your opinion on his optimum, or perhaps I should say his minimum waist size?”
“What are you thinking?”
“Miss Maggie thinks 26 inches should be his waist size. I think the boy can go down to 24 inches. He is rather petite and small boned. And I think there is still some fat on his waist. What is your opinion doctor?”
“He hasn’t started his hormones yet, so that should redistribute some fat. And I agree that the boy is a petite. But 24 inches …? I think it might be difficult.”
Mistress Ann would not give up. “But do you see a problem if we try?”
“No, not really.”
“Excellent. Then Samantha, we shall have Madame Longet prepare you a new corset as soon as she can.”
“Oh whoopee,” Sam thought to himself. Although he had grown accustomed to his current corset, he by no means liked the foundation. It was tight, hot, confining and limited his ability to bend over. Another two inches was going to be murder. But … he wanted to be a pretty girl. No pain, no gain.
Dr. Ratchet resumed Sam’s examination — and inspection. She was the lead doctor — at least it seemed to Sam — but Dr. Bethune could not keep her hands off him. She extensively palpated his nipples, chest, hips and buttocks. When Sam was seated in the gynecology chair, she spent several minutes examining his scrotum, testicles and penis. “May I milk the boy?” she asked Dr. Ratchet. “I want to check his prostate.”
“But of course. I shall collect the semen.”
Sam felt like a piece of liver as the two doctors handled and examined him. Dr. Bethune began stroking Sam’s prostate and soon had him ejaculating into Dr. Ratchet’s vial. When she had milked all of Sam’s semen from him, she stroked his penis to get the last precious drop out of him.
“Are you sure you are not going to have SRS, Samantha?”
“Sexual reassignment surgery. You are the perfect candidate for it. I can give you exquisite sensitivity in your clitoris.”
“No ma’am. I am not doing that!”
“Pity my boy. You would be perfect. So be it, we have some other business to attend to. We need some 3D pictures of your face and chest.” Sam was given a robe and taken into another room with several dual-lens cameras. He was photographed from the waist up, front on and profile. Then additional pictures were taken of his face from a much closer distance.
Dr. Ratchet and Dr. Bethune talked about facial structures, and bones and sinuses and lips and cheeks and jaws and chins and on and on. They poked and felt his face and measured the size of everything.
After much discussion Dr. Bethune addressed Mistress Ann, “I think we have a consensus then. Next Friday we can perform his nose surgery, I will add cheek bone enhancement and I will give Samantha the most darling dimples you have ever seen. Dr. Ratchet do you concur?”
“Mistress Ann, what is your decision?”.
“I agree. I’ll inform the sponsor and if she changes anything I will let you know immediately.” No one asked Sam for his opinion
“Excellent then. I shall be off and Dr. Ratchet can give the boy his facial peel.” Dr. Bethune left and Dr. Ratchet took Sam back to their original examination room.
“This will be your second facial Samantha. Your skin looks very nice and so I am going to stay with the same concentration as last time. Next time we will increase your concentration. This level will leave you in good condition for your surgery next Friday. At this low concentration you will heal quickly. I will not be here, but rest assured Dr. Bethune is the best in the world. After surgery you will be sent home, and a nurse will accompany you. She will stay for the first three or four nights to make sure everything proceeds along acceptable levels. You will be a very pretty girl, Samantha.
“Do you have any questions?”
Sam had a question, but not about his surgery. “When can I start my hormone treatment?”
“That depends on your semen, Samantha. We need to collect a few more vials. If your semen is good and healthy, 3 or 4 weeks more I would say. If not, I might have to double that time.”
Sam was very quiet on their walk back home. Things were going to get more real for him. Surgery was a big step. And so was his hormone treatment. But that was too far away. Sam wanted to start now. He wanted to grow breasts so he could start wearing a bra again. He wanted to look like a real girl once more, not a dressed up boy. Sam was in a hurry to become all that he could be.
Mistress Ann had Sam in the swing of his new routine. Mornings rarely varied, but afternoons changed to accommodate various items. The 1:00 to 3:00 time slot handled trips to the dentist, the doctor, the beauty salon, the grocery and to Madame Longet’s. On Thursday Madame Longet gave Sam his first fitting for a new corset. God it was going to be tight! But Sam accepted it as necessary for his feminization. He wanted to be a beautiful girl, and he would do what Mistress Ann instructed.
Saturday the two of them had the ballet school to themselves. Mistress Ann kept Sam an extra hour to teach him a few new movements. In the afternoon Sam was dressed in a pretty — and frilly — dress and taken for a walk around the neighborhood. Mistress Ann held his hand as she took him through the courtyards and under the streets using the Guild tunnels. Sam saw the other boys out running and playing and enjoying the beautiful weather. Most of the boys were wearing their school uniform, although a few wore summer dresses and participated in less physical activities.
Sunday they went to church. “I understand you are not much of a church girl, Samantha.”
“Well, we’re going mostly for the social side. You can ignore the church services. I want to show you off to the other boys. Perhaps you can meet and talk with a few of them. Mistress Ann put him in one of his nicest dresses, complete with knee socks and leg ribbons. She clipped a real flower in Sam’s hair and gave him short, lacy gloves to wear. As they were about to leave she handed him a tiny little purse with a short handle. “Pretty girls do need a purse at church,” she told him with a smile.
They walked to church hand in hand. When they arrived Mistress Ann greeted a few of the other matrons, and introduced Sam to some of the older boys. Sam was impressed with the other boys. They were wearing more age appropriate clothing, but they still wore very nice dresses. In turn, he felt silly being dressed in his “Lolita” dress. The boys also had on makeup. Sam would have killed to be wearing lipstick and mascara. They all had long hair and about half of them had it put up in a semi-formal style.
But most obvious, and painful to Sam, was the presence of breasts. All of the boys had boobs. They were all wearing bras — Sam could see their bra straps, and some of the boys were even exposing cleavage. They had beautiful and bountiful cleavage with clear, soft skin. Their voluptuous bosoms accented their narrow waists and large hips. Most of the boys had larger hips than Sam. But they all had curvaceous bodies, accented by breasts. Sam ached to have his breast forms and brassier back. He couldn’t wait to start growing his own breasts. He felt so inadequate next to these boys. Sam wanted to grow up and become a woman.
The boys were very friendly and chatty. They introduced themselves and asked Sam a few polite questions. They seemed very happy and bubbly in their Sunday clothes and enjoying the social atmosphere after church. Sam was invited to join them for ice cream and he was allowed to accept. Mistress Ann still held his hand and walked him to the ice cream shop. She gave him two Euros and allowed him to buy a treat. “We will work it off you tomorrow,” she told him with a mischievous grin.
The boys talked about many things, and Sam mostly listened. Much of the conversation was in French, but for his benefit they spoke half the time in English. He was surprised they didn’t ask him more about himself. But he would find out later that private lives, and families especially, were not topics of conversation. Mostly they talked about clothes and fashion. Makeup was popular. Movies and actresses and how they dressed for the award shows accounted for some of their conversation. They even talked a little about hormones and how they had different affects on the different boys. Hormones were probably the topic du jour for Sam. He was very interested in the boy’s comments about hormones, and he listened raptly.
Mistress Ann allowed Sam to socialize for almost an hour, then she walked him home. “You need to write to Mistress Lisa and tell her about your week. She wants a weekly update.”
“I don’t have my lap top, may I borrow yours, ma’am?” he asked.
“No computer, Samantha. You must write to her by hand. I know, it’s an old fashioned way to communicate, but it is romantic. Waiting for the post to bring you a letter has its thrills and anticipation Samantha. Plus, you need to practice your penmanship. I want you to work on small, clean strokes with a bit of flourish.” The other reason for no computer was to keep Sam from surfing the web. Mistress Ann did not want to take a chance on Sam finding out about Lisa’s upcoming marriage.
Mistress Ann handed Sam some pink note paper with Samantha embossed on the top. “I bought this for you a few weeks ago. I thought it would serve your needs. Now sit and write. Tell Mistress Lisa what you have been up to, and make sure to tell her you miss her.”
When Sam had finished, Mistress Ann showed him how to put just a tiny little drop of perfume on the letter before sealing it up in the envelope. “We mail it tomorrow and then you can wait for her reply. Trust me; getting a love letter through the mail is much more romantic than an e-mail. Plus you can keep your love letters forever. They make a precious keepsake.”
The following week Sam followed Mistress Ann’s routine. Monday and Thursday afternoon Sam was taken to the doctor’s office for his bi-weekly milking. Tuesday Sam received his new corset from Madame Longet. Damn was it tight! Mistress Ann couldn’t pull it completely tight. “Don’t worry honey, we will get that weight off you. And when you start your hormones, you will have just a wonderful figure.” Sam was already losing weight. Mistress Ann’s starvation diet, coupled with his ballet workouts was slowly removing the pounds from Sam’s petite frame.
When they finally reached Mistress Ann’s goal of 105 pounds, Sam thought he was too skinny, but Mistress reminded him that a girl “Can never be too thin or too rich”. Mistress Ann was always right about her boy’s figures. With hormones and surgery Sam would have a prefect body; soft, curvy, feminine and busty. And his two doctors would make sure he was pretty with perfect skin and a feminine face.
And Dr. Bethune did just that on the following Friday. Mistress Ann took Sam to the office at 9:00 sharp. Sam was prepped and in surgery by 10:00. By noon he was coming out of the anesthesia and receiving his first morphine shot. Surgery is always painful, no matter what people claim. And morphine is the pain reliever of choice. Sam’s nurse would keep him pain free through the weekend.
Sam was moved home later in the day and placed in bed. A nurse spent the weekend taking care of Sam. He was valuable chattel and needed the best of care. The nurse shared Mistress Ann’s bed and was able to give Sam the close attention that he needed. By Monday most of his pain was gone, but he was uncomfortable. His entire face was bandaged, he had two black eyes and he had to breathe through his mouth. That was the worst part, as his mouth became dry and extremely yucky.
On Monday the doctor made a call and changed the bandages. On Wednesday she returned and took off a few more bandages. On Thursday, bandages and all, Sam was at his ballet lesson and back in routine. By Friday much of the swelling was down and all of the bandages were removed. Sam could see ugly red marks around his nose, but it did look smaller. His cheek bones were higher and he could see his dimples. God he was going to be cute! Sam was going to be stunningly beautiful. He just knew it!
It took three weeks before the redness and swelling were completely gone. He had a cute little, up-turned nose, high cheeks, and dimples that deepened when he smiled. When Sam wanted to totally captivate someone, a smile with those dimples would be irresistible. Every time Sam looked in the mirror he was impressed with his own beauty. He was becoming just a little bit conceited. With make up and boobs Sam knew he would be the most beautiful girl imaginable. Now, if he could just get out of these stupid girly petticoats and start growing some tits!
And finally that day came. He went to the doctor for his regular milking and after she had finished milking his prostate Dr. Bethune said, “Samantha, I have some good news for you. We are done with your semen collection. Today you can start your hormones.” Sam flashed those beautiful dimples at Dr. Bethune as his smile showed his pure joy. “Finally!” he said to himself. “Now I can begin growing my new body. I’m going to have the body of a girl at last. Lisa is going to be so happy … and impressed.”
Things slowly changed for Sam as summer wore on. Life got even better. Now he knew that he was finally moving towards a more feminine appearance. He understood the need for weight loss and that god-awful corset. But now he worked even harder at his ballet lessons. He liked ballet. Everything was so graceful, slow and powerful. He felt that his legs were stronger and he knew his ankles, feet and toes were stronger. He felt more in control of his body. When Sam wanted to strut and throw a little more sway into his hips, when he wanted to use a runway walk or when he just wanted to skip or jump for joy he was so much more confident and comfortable doing it.
Sam knew he could use his body to move and exude the pure feminine joy that he was experiencing. No boy, or mistress, would be able to resist the new Sam; or to be more precise, Samantha. By late summer his breasts felt like they were finally responding to his hormones. His nipples were puffy and irritable. That is if a nipple can feel irritable. He just noticed them more. And he loved the sensation.
Sam was writing and receiving love letters from his mistress; sometimes two per week. Mistress Ann was right about writing letters. There was something about anticipating the arrival of the mail, of opening a perfumed letter and then sitting in a corner by himself and reading it three and four times; absorbing every word, every letter, and every curlicue of Lisa’s exquisite handwriting. She would praise his progress, thank him for the pictures (that Mistress Ann E-mailed), share her loneliness and tell him how horny she was. Lisa missed her courtesan and wanted oh so much to come visit him.
But first things first; Labor Day weekend was upon them and Lisa was getting married. Only halfheartedly, Lisa went through the process of organizing her marriage to Jeff Winter. She had her wedding gown and the bridesmaids had their gowns. Flowers, bands, cakes, caterers and the entire infrastructure of an expensive wedding had been chosen and planned. Harriet flew in from Switzerland and as maid of honor took Lisa and the girls out for Lisa’s bachelorette party. They went to the best clubs in New York City and drank the most expensive champagnes.
The relatives flew in from around the country and brought expensive gifts for the newly weds. The ceremony was held in a large cathedral and hundreds of guests arrived. The reception was held in an expensive hotel and the party lasted to well after midnight. And later that night Lisa and Jeff consummated their marriage. Once and only once they were truly a couple. And after fulfilling her wifely duty, Lisa left their wedding bed and went to the guest bedroom, where she cried until the sun rose in the east.
Lisa missed the love of her life. Next time she would do it right. Her “real” wedding would be small and private, and the reception would be more subdued. But the two brides would be beautiful beyond description, and their love would be boundless. And most importantly, their consummation would be glorious! Lisa would not be happy until that day.
After the summer, Sam began receiving visitors. Mistress Ann felt he was ready, so every so often one of his future in-laws was allowed to stop by. Harriet was the first. She took Sam to dinner in a local restaurant while Mistress Ann served as chaperone of course. And Sam was allowed to be Samantha for an evening. He was allowed one of those “dress-up” days that little girls love so much. He even wore a bra over his tender nipples. Samantha still looked flat, but “she” felt so much better. Yes, Samantha felt like a she once again. Sam the boy morphed into Samantha the girl and she truly enjoyed seeing Harriet again.
And Harriet enjoyed seeing Samantha. They were kindred spirits in more ways than one. They shared a common opinion on politics and that was their binding attraction. Harriet visited “young Samantha” seven times that fall. She was looking forward to “dating” Samantha the teenager after Christmas; they would have no chaperone then.
A week after Harriet’s first visit, Miss Maggie stopped by for a day. Sam savored the familiarity of her perfume as they shared a hug then faux kisses. Miss Grace and Miss Eunice came by in early October, and towards Halloween Gisela and Janice were in Paris for a few days. Sam loved seeing familiar faces and he talked non-stop about his experiences and travels. And he especially loved seeing Gisela. Gisela had been Mistress Ann’s favorite student, but Sam was now running a close second.
Mistress Ann would allow Sam to dress “older” on selected weekends and then take him to museums, zoos and sightseeing around the Paris area. Sam even went horseback riding one Sunday.
Sam still had to wash and set his hair every other night and he was getting used to wearing curlers to bed. The next morning he would remove his curlers and pull his hair into pigtails or a ponytail. Mistress Ann would give him pretty colored ribbons to tie his hair. The routine of curling his hair and then wearing pigtails made little sense, but Sam knew the reason; it was all part of his training.
As fall moved on, Sam’s hormones began taking affect and started changing his body. His breasts and nipples were growing, but Mistress Ann still confined him to only a training bra. Sam really wanted to wear a push up bra and show off his growing cleavage, but he was still a jeune fille in Mistress Ann’s eyes. She dressed him in frilly petticoats and knee socks and Mary Jane shoes. Only on the occasional “dress up” day was he allowed to wear thigh highs and heels.
Sam enjoyed his ballet lessons, they were probably the biggest surprise to Sam. Coming into his training he had never anticipated ballet, but now it was one of his favorite activities. His French was improving and so was his voice. Singing made all of the difference in the world. His poli sci lessons were progressing nicely and had moved from the old South to the new Washington. He was now learning something useful.
Sam was happy with his training, but all was not perfect. His new corset was still very tight even though he had dropped to his final weight. Mistress Ann assured him that as the hormones performed their magic, less fat would go to his waist and more to his hips and buttocks.
But what Sam really wanted was his own mistress. He wanted to see Lisa. And finally she arrived. Lisa flew to Paris for a 4 day weekend at Thanksgiving. Early on Thanksgiving Day Sam was dressed in his frilliest, laciest little girl dress when he heard the knock at the door. He dropped his magazine and sat up straight in his chair while Mistress Ann answered the door. She seemed to spend the longest time talking at the door before she brought Lisa into the parlor. Sam could barely restrain himself and he was bouncing on the sofa while he watched his magnificent mistress glide into the room.
Lisa was the most beautiful girl in the world. She was dressed demurely in a mid-calf skirt and cashmere sweater, but you couldn’t hide her figure and prominent breasts. God, Sam wanted breasts like that. She was wearing makeup, something that Sam was only allowed on special dress up days; but unfortunately today was not a dress up day. Mistress Ann wanted to present Lisa’s little girl.
“Please greet your mistress, Samantha.”
Sam stood as gracefully as possible and curtsied, “Hello Mistress Lisa.” Sam had a huge smile and he wanted to dart up to her and squeeze her in a tight hug.
“Hello Samantha,” Lisa answered politely. “My but don’t you look pretty. You are such a lovely little girl.”
Mistress Ann invited Lisa to sit next to Sam, but Lisa couldn’t wait to hold her cute courtesan boy. She daintily exchanged faux kisses with Sam then grabbed him in a bear hug. “So much for decorum,” Mistress Ann joked. “I’ll be in the kitchen if you need me.”
Sam and Lisa kissed and quickly had their tongues in each other’s mouth and down their throats. Lisa had her nails digging into Sam’s pretty tush and Sam had his arms over Lisa’s shoulders and around her neck. “I missed you so much,” Lisa said.
“Me too,” Sam replied, took another breath and continued kissing Lisa.
Mistress Ann returned from the kitchen and the two of them were still standing in the same place and still groping and hugging one another. “Why don’t you two go get a room?” she said.
“I think we should,” Lisa answered. “Mistress Ann, may we take our leave?”
“Yes you may. Samantha, your valet is by the door, right where you left it three hours ago.”
“Thank you, ma’am. I’m all ready Lisa.”
“Samantha!” Mistress Ann snapped. It was the loudest she had ever spoken to Sam. “Have I taught you nothing? You will address your mistress properly!”
“I am sorry,” he apologized. “I got caught up in the excitement of seeing my mistress. Mistress Lisa I am ready when you are.”
Lisa smiled and took Sam’s hand. “Come with me Samantha.” Sam picked up his valise at the door and they walked out to Lisa’s limousine. Andre was their chauffeur and he helped the two girls into the rear seat. They immediately snuggled and Lisa took Sam’s hand. “You are a sight for sore eyes, Samantha. You look so beautiful and feminine. I love your dimples. And you little nose is too die for. God, you’re cute!”
“Thank you. And I missed you too Lisa.”
Lisa quickly placed a finger over Sam’s lips and stopped him from speaking. “You must address me as Mistress Lisa. Please remember that.”
Sam looked like he was in shock. “Are you serious?” he thought. “I understand in public, but we’re lovers.”
Lisa could read Sam’s thoughts and she said, “Yes Samantha, you must be proper at all times. You agreed to this. I am your mistress now, and you are my courtesan. We must adhere to the rules. It won’t be so bad, you will get used to it.”
Sam was miffed. As happy as he was to see Lisa, some of his excitement was dampened. He hadn’t thought that she would really expect him to follow all this formality in private. Was he really going to be a second class citizen to her? In private? In bed too?
Lisa didn’t want Sam to pout in silence. “I can’t wait to get you back to the condo. I want to see how much your hormones have changed you. I love seeing your weekly pictures but I can’t wait to get my hands on the real McCoy,” she said with a gleam in her eye.
Sex. Now that was something that could get Sam’s mind off his moping. But Sam was nervous. He wasn’t sure if he was going to be able to perform up to Lisa’s … excuse me, Mistress Lisa’s expectations. He knew the hormones were going to affect his ability to produce sperm and have an orgasm, but he had not had one single opportunity to test drive the new equipment. Mistress Ann never let him out of her sight; even in the bathroom. And at night his bed squeaked so much that if he had even thought of masturbating Mistress Ann would have heard. So Sam was apprehensive.
“You know ma’am, things are going to be different in bed. I mean, I won’t be able to perform … to please you like a real man can.”
Lisa thought it was so cute the way Sam addressed her as ma’am. Damn she liked that! This is what she had dreamed about ever since she was a little girl. Total control over an epicene and feminized boy was her life-long dream, and here he was. Fantastic!
“Don’t worry about a thing Samantha. You will be perfect for me. You bring me such pleasure and pride when you are between my legs and orally stimulating me. You are the best cunnilinguist in the world.”
“That wasn’t what I was worried about, ma’am.”
“I know what you are worried about, but don’t be. You can still get an erection and that is all I need. I’ll do the rest my little filly. I know things have changed, but this is what we both wanted. No matter what happens, you will always be my silly filly,” and she kissed his soft lips.
When they reached the condo it took Lisa just seconds to pull Sam into her boudoir and begin stripping him naked. “I love the way you are dressed Samantha. This dress is just so cute on you. Do you enjoy petticoats and knees socks?”
“They’re ok, but I prefer nylons and heels. I can’t wait until I can start dressing as a teenager, ma’am.”
“I know you are in a hurry to grow up. You have told me countless times in your letters. I think you are cute dressed like this. But you’re even cuter when you’re naked,” and she slowly stripped off Sam’s dress and lingerie. She soon had him naked and standing in front of her. “Please show me all of you,” she said and circled her finger to indicate that she wanted Sam to spin around for her. “Oh my, you are looking good. I can’t believe that you have lost that weight and that you are now wearing a 24 inch corset. Your waist looks tiny … and so sexy. Are you really down to a size 8 dress?”
“That is what Madame Longet says, ma’am.”
“But I really like the look of these,” and she softly touched Sam’s nipples. He jerked very slightly as Lisa touched and caressed them. They were still sensitive for Sam. “You are coming along very nicely sweetie. I love the look and feel of your breasts and nipples. I can’t wait to get you into bed. But first …,” and she presented herself to Sam.
After Sam had stripped his mistress and caressed her entire body, she took his hand and pulled him to the vanity. “You must wear lipstick for me, Samantha. You look so much sexier with those pouty red lips of yours.”
“I know ma’am. I want to wear makeup but Mistress Ann won’t let me.”
“She doesn’t want you to grow up too fast Samantha.” While Sam applied his lipstick, Lisa prepared their bed. She propped up her pillows and sat against them, spreading her legs and waiting for Sam. By the time Sam reached her there was already a large wet spot on the bed. Sam nestled between his mistress’s legs and slid his hands under her ass and gave her a soft squeeze. “Remember Samantha, just the way you used to do it; soft and slow. Be my lesbian filly.”
Sam had not forgotten anything, and he was very soft and tender as he placed a soft kiss on Lisa’s quivering cunt. His tongue slowly parted her labia and he tickled her clit with the most exquisite care and attention. With just one little touch Lisa’s back arched and she screamed in delight, squirting Sam’s face with her fragrant juices. Sam helped her by tightly squeezing her ass and helping her lift off the bed.
“Did you miss me?” he asked facetiously.
Lisa was in nirvana and didn’t even bother to reprimand his lack of respect. When she was in the throes of orgasmic delight, she could forgive Sam for not addressing her properly. He could call her ma’am after their sex.
And Sam caught on immediately. “Thank god she isn’t going to treat me as her handmaiden when we’re having sex,” he thought.
Lisa was all too eager to have another go at ecstasy, and Sam was all too happy to oblige. He loved being between Lisa’s legs, enjoying her femininity and raw sex. No amount of hormones was going to dampen his excitement and pleasure when he was kissing and fondling Lisa’s quim. Sam brought his mistress to three orgasms before she was satisfied.
Lisa looked into Sam’s eyes as she gently kissed his delicious lips. Lisa also liked the taste of lipstick; especially when it came from the lips of her favorite boy. Sam laid back and enjoyed the attention of his favorite girl. Lisa moved down to Sam’s nipples and gently tongued them. Sam’s nipples immediately responded with a shiver and hardened. Lisa gently gripped his opposite breast as she suckled on his aroused nipple. Sam was in heaven. His breasts were still sensitive, but he had never felt such an exquisite pleasure in his breasts. Lisa’s caressing was not going to bring Sam to an orgasm, but the new and wonderful feeling in his nipples and breasts drove away any remaining doubts that he might have had concerning his use of hormones. Sam loved his feminine body and new sensations.
Lisa could wait no longer and she threw a leg across Sam’s stomach and slid down his thin waist and expanded hips. Sam’s lower torso felt different to Lisa. Sam was wider where he should be wide (in his hips) and narrower where he should be narrow (his waist). Lisa’s legs and thighs just seemed to fit her boy better than they ever had. Sam’s new proportions were perfect for his epicene body.
Sam’s erect penis looked smaller than before as it lay on his soft skin. Lisa noticed how much softer his skin was and she caressed his stomach as slid her hand to his cock. She took it in her hand and gently stroked it before sliding it into her wet pussy. Oh god, it felt good going in and Lisa immediately began squeezing, sliding and rocking up and down, in and out with Sam’s remaining masculinity.
Sam also enjoyed his lover’s attention, and while everything was exquisite, he felt slow; slow to respond to Lisa’s attention. She reached orgasm long before he was ready. Lying on top of her toy she gave Sam a little kiss. “I love your lips. Did you cum?”
“No,” he answered quietly.
“Don’t worry lover, you were wonderful for me. So wonderful that we shall give you another chance.” She did a push up to apply more pressure to Sam’s entrapped cock and again she slowly began stroking Sam’s penis. Sam helped along and after a few minutes he too came to climax. Only it wasn’t what he remembered. His orgasm was “less” than what he remembered. It wasn’t nearly as intense as it used to be. But Sam was satisfied. He was going to be a girl and he knew the sacrifices. Besides, his nipples had felt wonderful under Lisa’s fondling. Yes, Sam was satisfied with his new body and life.
After a short nap Lisa suggested a shower. Sam readily accepted. While fondling one another under the excuse of toweling off, Lisa suggested a trip to the Eiffel Tower.
“I would love to,” Sam said. “But I don’t feel comfortable in my dress. I think I look too young and silly. I won’t look nearly pretty enough for my mistress,” he claimed. Sam was playing to Lisa’s vanity. “What kind of arm-candy looks like a little girl in pigtails?”
“Not a problem my pretty filly, you still have all of your clothes here.”
“Really?” he said with a big smile.
“Yes. But I wonder how well they will fit you. You have … improved since you last wore them. We may have to go shopping!”
“Darn, ma’am,” Lisa reminded him.
“What about my hair, mistress?”
“Leave it down, it’s long enough now. It will give you that sultry look.”
“I like the sultry look, ma’am.”
Sam went crazy buying bras for his new breasts. They certainly deserved more than the silly training bra Mistress Ann was forcing him to wear. He found some wonderful push up bras that gave his tiny breasts real cleavage. He bought a dozen bras including strapless, red, purple, silk, lacy and push ups. The only thing he didn’t buy was a minimizer.
And then they went dress shopping. Most size 8 dresses fit him, and he even fit into some 6 sizes. Lisa was jealous of her beautiful boy, but proud. Sam did indeed make beautiful arm candy for his mistress. Sam found several dresses, but he particularly liked one red dress that he wore to dinner and then to the clubs that night. Sam liked red. Sam sizzled!
And so did their vacation. They had the best Thanksgiving of their lives.
At the urging of Sam’s sponsor, Mistress Ann promoted Sam one month early. December first he “officially” became a teen ager. Sam the teenager was allowed to show off his breasts and dress like a 16 year old girl. That was still a little young for Sam’s wishes, but much better than a 10 year old. He was allowed to wear real bras once again. His training bras were better than nothing, but not much. Sam loved wearing a bra and he felt so much better, so much more “real” and feminine when his little girls were strapped in and cuddled by soft satin. His girls actually purred once they were in their proper environment.
Fashions in Paris that winter featured calf-high boots with stiletto heels and nylons. The look was often coupled with short dresses — not minis — and provided a sexy look that Sam really liked. He was allowed more latitude in his clothing; dresses, skirts, blouses and sweaters. Cashmere sweaters in winter were awesome. Sam’s hair was longer and he still wore curlers to bed every other night. But now he could do something with those curls. He was learning to style his hair and he tried and enjoyed different looks. And he didn’t have to wear little girl ribbons or barrettes in his hair either.
He also enjoyed different looks with his makeup. After his morning ballet lesson, Mistress Ann had him working the remainder of the morning in a beauty salon. When he arrived each morning, the stylists were allowed to experiment with Sam’s hair and makeup. Mistress Ann wanted Sam to broaden his make over experience and not fall into a rut. So some days his hair was up and other days down. Some days his hair was curly and some times straight. And his makeup went from daytime demure to evening sultry.
And once a month, just for old time sake he wore Goth. The beauticians were very good at teaching him new ideas, and Sam avidly absorbed them.
Sam would work behind the girls, watching how they cared for hair and created becoming styles. Sam learned how to wash and set, hi-light, cut color and perm hair. He was given first hand experience with waxing, manicures and pedicures. He learned many details he would later use when caring for his mistress.
Dr. Ratchet continued to show up and give him his facial peels. She was an experimenter, and had decided to change Sam’s routine. She wanted to stretch out his sessions for three years and remain at low TCA levels. The time between sessions was stretched from 8 to 12 weeks and the number of sessions from 6 to 12 sessions. His facials would continue well after the conclusion of his training with Mistress Ann. The doctor felt this would provide Sam with soft, blemish free skin for many, many years.
On weekends Mistress Ann took her young apprentice traveling. Sam’s French was improving and he was able to appreciate contact with more people. So they traveled around France and even went to Amsterdam and Berlin for long three day weekends. And even more interesting, Samantha had a regular caller on weekends at home.
Harriet and Sam were becoming very good friends. Harriet was allowed to take Sam on “dates”. What that really meant was that Mistress Ann did not accompany them. But she did set a curfew of midnight. The curfew did not stop them having fun. Harriet usually took Sam to dinner and sometimes to a club or movie or just a coffee shop to talk. They had much in common in their philosophy of politics and life. They both enjoyed their female status and femininity. And they talked about the future and what they could accomplish in the world of politics. Both girls had idealistic views and big intentions. They wanted to change the world — for the better, not the money.
And they liked each other’s femininity. To put it crudely, Harriet and Sam had sex together. Sam refused the first time. He wanted to, especially his hormones, but he felt too much conflict. Harriet accepted his decision and didn’t force him. But the second time she invoked her Hawthorne privileges to help assuage Sam’s conscience. Sam conceded and carried out his responsibility by giving Harriet his very best effort. As their friendship and “dating” continued their trysts became more mutual.
Sam felt guilt at “cheating” on Lisa, but he was conflicted. Since July he had seen Lisa only twice; once at Thanksgiving and again at Christmas. Sam was lonely. Sam loved Lisa and he struggled with himself whenever he had sex with Harriet. But the ground rules had been set by Lisa and he had to accept Harriet’s demands. He wanted to write to Lisa and tell her about the sex, but he didn’t know how. He was beginning to like Harriet and he enjoyed being with her. He was lonely and Harriet was here with him. He didn’t like cheating on his fiancée, and no matter how many times Harriet reminded him of the rules he couldn’t shake his conflicted feelings. But Sam was lonely and Harriet was a warm and friendly body. Sam felt like a quiff.
Lisa was coming to visit him on her Spring break and Sam was very excited. He decided that he just had to stop “dating” Harriet. But he didn’t want to lose her friendship either. Not only were they now good friends, but Sam expected Harriet to be an ally when Lisa began moving into politics; and he meant his ally, not Lisa’s. So two weeks before Lisa arrived he tried to break off their affair. Harriet was unhappy at first, but Sam was able to convince her to see reason. And he did it without turning her against him. Harriet was smart and she realized that they were playing with fire. If Miss Mona found out about their trysts, Harriet would be in big-time trouble. Lust often takes foolish chances, but both of them finally saw reason and stopped their sex. After Lisa departed they continued to see one another, but their visits were further apart and their relationship stayed platonic.
One of the extenuating reasons for Sam’s and Harriet’s sexual liaisons had to do with another change in Sam’s schedule. After returning from the salon each day, he changed into his maid uniform and prepared lunch for Mistress Ann and himself. Then, three days a week he removed his maid uniform and had sex education. He often practiced his lessons with Harriet. Harriet was far and away the best sex teacher he ever had. Not only did Sam enjoy sex with Harriet, but she taught him things far beyond his “formal” education.
Mistress Ann began by giving Sam books on sex. Some of his sex education was academic, but he also had practical studies and “labs” as well. Sam’s sponsors had made it clear that Sam was not allowed to be with a genetic girl unless absolutely necessary. So Sam was taught first hand by two transsexuals.
Sam’s sex education began with massage. His teachers first demonstrated on him, and then he returned the favor. Oils, flavors and special “spices” were added to the mix. Whipped cream was messy, sticky and delicious. So was chocolate syrup. Sam learned the finer art of correct “placement” of additives. Sam thought it was fun and frivolous, but Mistress Ann reminded him that like religion, there is nothing frivolous about sex. It invariably involves egos and attachment; the latter being the most powerful and dangerous.
Sam’s teachers taught him flirting and seduction. Sam saw great use in the flirting, and he pushed for advanced techniques and suggestions. He could see it being very useful in his political work. Seduction was more dangerous and he wondered if he would need to use it in the political world, but he would definitely use some of his education on Lisa and her family; especially when he needed special favors or capitulation on certain political policies.
After learning massage and other precursors to sex, Sam’s education became more … personal. With Mistress Ann watching and directing, Sam had sex with his teachers. He learned the Kama Sutra positions and practiced each one. He was taught to be submissive in the bedroom and to surrender to all demands placed upon him; no matter his personal desires and preferences.
Sam was introduced to some bondage and S&M sex. These lessons were superficial and introductory only. Sam learned about the use of safe words and that was the most important item for him to know. But he found everything distasteful. He prayed that none of his future in-laws would lean in these directions.
Only twice in all of his training was he with a real girl. Mistress Ann brought in a pretty girl to teach Sam cunnilingus. She took her position on the bed and began talking Sam through the basics. However she was soon screaming in delight as she found out how experienced and talented Sam was. She told Mistress Ann afterwards that never had she been so pleasured by a boy or girl. She lavished extensive praise on Sam.
That was his first time with a female instructor.
The second time Mistress Ann broke a golden rule; never have sex with a student. Mistress Ann had to see for herself how talented Sam truly was. One evening she invited Sam to her bed and instructed him to go down on her. Sam knew nothing about her rule and found no trouble in accepting her instructions. Deep down inside he thought she was too old for this type of thing, but that was the thinking of a 19 year old boy. What did he know about older women? What he did know was that she had a firm and supple body. He had been dressing and bathing her for a year, and in more than one fantasy dream he had shared his body with her. It was a natural fantasy — his Oedipal fantasy.
Mistress Ann went to sleep with a smile on her face. The boy was talented — no doubts there!
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