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Remember in the first Chapter. Robert Long was found by his sister in her bra and panties. Where he confessed that he couldn’t help himself. Jessica Long then decided to help Roberta find her true self. By the end of the summer. Roberta has been wearing some kind of feminine clothing since April. We now find Roberta about to start her new school.

It is not what she expects.


MOM! I Can’t Help Myself                   by: Jennifer Allison


Chapter 2          Roberta: First Day at Miss Lynne’s School for Girls

Remember in the first Chapter. Robert Long was found by his sister in her bra and panties. Where he confessed that he couldn’t help himself. Jessica Long then decided to help Roberta find her true self. By the end of the summer. Roberta has been wearing some kind of feminine clothing since April. We now find Roberta about to start her new school.

It is not what she expects.

"Roberta, I would like to ask you a question. It is one I should have asked last April, but I never did.

"What exactly do you want to do? Stay as Roberta or go back to being Robert."

"Mom, don’t say anymore. I want to stay Roberta. I even want to have that operation. The one they call the sex change. The way I figure it. I won’t be able to afford it until after college. I have started saving up. Half of my allowance and half of any other money I earned go into a special saving account I have setup."

"Do you know will happen to you?"

"Yes I do. I dream of the day I will have my penis removed and a vagina in its place. I check it out over the Internet."

"What about the other things? Things a girl needs to know, and a boy doesn’t. If there was a place where they can teach you the ways of being a woman, would do go there."

"In a second. I did a lot checking on the Internet. There are a few places out there, but all of them require a person to be at least 18. I won’t have my fifteenth birthday until October.

"Mom, why all the questions?"

"Just checking something out. Right now Roberta I want you to do something strange. In the bag at your feet, there is a black hood. Could you please put it over your head? I don’t want you to see where we are going. It is a big surprise."

Roberta did what she was told.

After what seemed like hours to Roberta. They finally came to a stop.

"We’re here. Don’t remove your hood yet. Take my arm and I will lead you."

As She was being lead, Roberta kept thinking. ‘What is happening? Where is mom taking me?’ Roberta even heard someone say. "Looks like we have another new student. This one is a little further along than most. Her breasts are starting to show." Roberta was a little ashamed. First time in public and the first person that sees her, notices her breasts.

As they walked through a door. "Roberta, we are here, you may take off the hood."

As she removed her hood, the first thing Roberta saw was this on the wall in big black letters.


As Roberta was digesting this she heard mom say. "Ms. Long and Miss Roberta to see Miss Lynne."

"MOM!! This can’t be your surprise. A girl school would be the worst thing that you could do to me. Girls will treat me worse than any boy would." As Roberta was saying this, she tried to leave.

Then came a sweet very nice voice. "Miss Roberta, don’t be afraid. You have nothing to worry about. I guarantee you won’t have any trouble with any of the other girls." This came from Pamela, Miss Lynne’s secretary for the day. Pamela remembered what her first impressions of Miss Lynne’s school two years ago. When her mother brought her here.

The intercom buzzer went off just then. "Yes, Miss Lynne."

"Please send in, Ms. Long and Miss Roberta," said the voice.

As they entered the inner office.

"Nice to see you again, Jessica."

Turning to Roberta. "You must be Roberta. You are a very lovely girl. Please have a seat."

A little shocked as being told by someone else other than her family that she looked lovely. He sat down. "Please stand up Miss Roberta." As she did so. Miss Lynne said. "Now sit down as a young lady would. Straighten out your skirt as you sit down. If you want to be a girl you must act like a girl at all times. I do not want you to cross your legs unless you do it in a ladylike fashion."

Roberta sat down. Keeping her legs together not wanting to upset Miss Lynne again.

"Roberta I bet you are very confused, on what is happening."

"Yes, I am."

"I can explain it all, in a few words. My school is for Boys who want to be Girls. Out of the twenty-one students we have attending this year. Only one of them was born a girl. The rest of them like you, who are pre-op boys."

"You mean to tell me, that there are 20 other boys in just our area who want to be girls?"

"No! My students come from ten different states. I am very selective on those young ladies I let attend. They have to be highly recommended. Even Amanda, the only girl had to be highly recommended.

"What happened there was. A niece of one of our major benefactors, she was raised by her father as a boy. He recently died and she moved in with her aunt. So her aunt has sent her here to learn to be a lady."

"You mean this is one those school I read about on Internet?"

"No, we are not like those. 95% of those don’t do the job they are supposed to. We teach our student everything they need to know about being a girl. Like just now, sitting, crossing your legs, and walking. We will teach all our students everything. None of our former student have been found out yet."

Very hesitantly, with worried voice Roberta asked. "Will I be one of those students?"

"Certainly, why do you think you are here. Your mother enrolled you in our school last April."

Roberta jumped up and went over to her mom. She was crying. Roberta started hugging her mom. In between the sobs, these words could be heard. "Thank You, Thank You."

Jessica hugged her daughter, and said. "This is that surprise I promised you back in April."

"Now, Miss Roberta please sit down. We have a lot more things to do."

Roberta went and sat down. Like a young lady would.

"Your first lesson. Let me explain in more detail. This is a boarding school. You will attend my school for the next nine months. You will attend classes just like a regular school, but there will be a lot of extra classes dealing with things a girl needs to know. Stuff a girl learns as she grows up, but since you learned only things a boy needs to know we teach you the things you have missed. "

"Are you a certified school so that I won’t have to repeat a grade?" asked Roberta.

"We are, but we very strict. A student must maintain a 3.0 grade point average in all classes. There will 4 quarters and two semesters. So if you have a 2.8 in the 1st quarter. You’ll need a 3.2 in the 2nd. We haven’t had to flunk a student yet."

"I don’t want to be the first."

"We are also very strict in discipline. If you break one of the rules, you will be spanked but not in excess. The rules are written down in our Rule Book. Also listed is the amount of spanks for each infraction. An instructor or a member of the staff can administrate any spankings. At all times an instructor or staff will be treated with respect at all times, no exceptions. You will have the right to challenge any discipline that is to be administrated to you. It will be brought to me. I will then listen to both sides of the issue. If you win, no punishment and recrimination, if you lose 5 more spanks will be added to your punishment. Do you understand me, Miss Roberta?"

"Yes I do."

"During your stay here, you’ll be assigned to group of four girls. I try to put groups together who will work well together. In your case, the four of you will turn fifteen within four months of each other. A Housemother, yours will be Ms. Stoneman, is assigned to each group. She will help you with your clothes and other things. She will be your mother away from home. You can tell Ms. Stoneman anything, and she will not break your confidence unless she feels it is in your best interest to do so. Then she will tell me, and I will decide how much further it goes from there. In the five years Ms. Stoneman has worked for me. None of her girls have had or even a reason to complain about her. Am I going to fast for you Miss Roberta?"

"No, why do you keep calling me Miss Roberta, why not Roberta?"

"All my student are called Miss, as the staff at all times will be addresses as Ms. or ma’am or with respect at all times."

"Now for something very important. I figure you have notice a few changes in your body since that day in April, when Jennifer first caught you in her bra and panties."

"Yes, I have," Roberta said, as she ran hand in front of breasts.

"That is part of the school. By helping you get ready for the big step. Your mom has been giving you female hormones since the first of June. Your skin is softer; there is very little hair. Your breasts started to make their appearance."


"The reason why we asked your mom to start you on the hormones. In about six weeks you’ll be given a very big choice. I know you have been checking out the sex change operation. The question we will ask is if you want yours."

"YES!!!!! I want to become a girl, all the way. I thought I had to be at least eighteen, before I could have one?"

"In most cases that is true. With yours and your mom’s permission and some good lawyers and some understanding Doctors and Judges we can have the operation done on a minor."

"Can I have mine tomorrow?"

"NO! The earliest any of our boys will have their operation is after Thanksgiving. It is one of the requirements that the judge requires. A boy must attend my school for at least six weeks before he can even consider a sex change application. The following people will have opinion on the matter. Your mom, yourself, the school doctor, an outside opinion from another doctor, myself, your instructors and Ms. Stoneman, might be asked, too."

"What happens if someone says no?"

"Out of all my students who have applied to have the operation. Only one was turned down. The reason why she was turned down. It was found out that it was her mother and not the girl, who wanted the operation."

"I do have another question. What happens if someone finds out I was once a boy?"

"I’ll make a bet with your Roberta. If you win, you’ll be able to get away with something minor without a spanking. If I win, 3 extra spanks will be added to your first punishment. Agreed."


"I bet you. There is someone you know right now. You knew before he started dressing up like a girl, before he had his operation and you know her a real girl."

"I’ll take that bet. I think I could tell."

"Do you remember Jennifer’s boyfriend Dean Courtland?"

"Yes I do. He was a bully and some other stuff I can’t say. He left town last February."

"He didn’t leave town. He started here at my school. A week after President’s Day. He had his operation three days after school let out."

"Wow! If you can take a bully like that and make her into a beautiful girl. You are a miracle worker. Still I think I would know Dean any where."

"Do you know where he is living now, and who is his best friend is."


"She lives with her mom and her best friend is your sister. You know her as Deanna."

"I guess I lose my bet. I would never have known."

"Mrs. Courtland is the one who told your mom about my school.

"I must now end this interview. There is another girl coming in for hers."

"So I go home and start school next week, right."

"No! Miss Roberta you have already started my school. In a minute Pamela will take you to Ms. Stoneman. We still have to sign the Letter of Agreement. Then I will give the rule book. I should warn you, a written fill-in test will be given tomorrow over the first half of the rule book. You will be required to get nine out of the ten questions right. If you don’t a make-up test will given, twenty questions, and 100% is required for this test."

"I understand, what if I don’t pass these tests?"

"You’ll be sent home. Here is the letter. Please read it and then sign it, as it is printed and then date it. If you agree to the terms"

‘I, Roberta Vanessa Long, agree to abide by the rules set down by Miss Lynne’s School for Girls. At no time will I ever reveal the presence of this school to no one. I agree to obey all instructions that are given to me by the staff and Instructors of Miss Lynne’s. I also agree to the honor code. Where I will report myself for any infractions of the rule book.’

Roberta Vanessa Long

28 August 2000

"That is the first time I ever signed my name that way. Mom, is Vanessa my middle name?"

"Yes, If you had been a girl, it would have been your name."

Miss Lynne called Pamela in the office. "Pamela, please take Miss Roberta to Ms. Stoneman."

As Roberta followed Pamela down the hall.

As they walked, Pamela asked a question. "You don’t recognize me do you?"

"Should I?"

"Three years ago I spent a lot time at your house. Jennifer even had a crush on me."

"I still don’t."

"My name back then was Paul Timmons."

"You’re Paul Timmons? You were supposed to be the next John Elway. Then you just disappeared."

"I didn’t disappear. I found my true self. I spent a year here, in February of that year I had my operations, so I went from captain of the football team to the captain of the Cheerleaders Squad."

"Does my sister know the truth?"

"No, I don’t want her to know either.’

"I won’t be the one to tell, Pamela."

"Roberta you got lucky in one respect. Ms. Stoneman is the best housemother at the school. I should know. She was mine.

"Also, If you need to talk to someone, other than your mother, sister or someone from the school. Get a hold of me. Ms. Stoneman will know how to."

When they came to a door, Pamela knocked. Then said "Ms. Stoneman, this Miss Pamela. I have a new student, a Miss Roberta and she has been assigned to your group."

A voice from inside answered. "Miss Roberta you may come. Miss Pamela you can return to your other duties."

As she walked in. Roberta noticed two other women in the room. An older woman in her late forties, who must be Ms. Stoneman and a younger one, her own age who must be her roommate.

What caught her attention more was what they were doing. The younger woman was holding onto a bedpost as Ms. Stoneman was lacing up a corset. Not one those new ones, but the old-fashioned kind. Like the one wore by Scarlett O’Hara in Gone with the Wind.

For the first the younger woman spoke. "Isn’t it a little tight? I can hardly breathe."

For a moment Roberta though she had recognized the voice.

Ms. Stoneman replied. "It’s supposed to be tight. It’s supposed to help you obtain the girlish hourglass shaped figure I know you want. You think it is tight now, just wait a couple weeks and you’ll wish you had this corset back."

For the first time Ms. Stoneman turned to look at Roberta. "Miss Roberta could you please come over here. I might as well start your training, next week the two of you will be lacing each other up."

"Yes, ma’am."

As Roberta moved over to Ms. Stoneman’s side. "I bet Miss Lynne didn’t tell about this. At all time our students will be wearing a corset. The only times you won’t will be in gym class."

The other girl spoke again. "You mean I have to wear this heavy and tight thing to bed?"

No it can’t be. The voice matched the voice of Roberta’s best friend Mark.

"Miss Marcia, my only warning, you forgot to add ma’am or Ms. Stoneman to your question. The answer to your question, yes you will have to wear a corset to bed. But not the one you are wearing but a more comfortable one.

"Finished, now turn around and meet your roommate."

"Miss Roberta meet Miss Marcia."

A looked of utter shocked came over Roberta’s face, as it did on Marcia’s. Finally Roberta broke the spell. "Is that you Mark?’

"Yes it is. Robert you certainly don’t look like my best friend anymore."

"Girls, please use your right names."

"How long have you been cross dressing?" asked Marcia. "And are those really yours?" Pointing to Roberta’s breasts.

"Yes they are, my mom started feeding me hormones the day school let out for the summer. I started dressing last January. Jennifer caught me in her bra and panties, the 1st weekend of April. The following Monday mom bought my own training bra and panties to wear around the house. What about you?’

"I started eighteen months ago. Stole some of my mom’s stuff and even got one of your sister’s panties. Last May, mom found my stash. When she confronted me I confessed. I started wearing my training bra and panties, the 1st of June. I started the Hormones the middle of July. I guess I will have my breasts by the middle of next month."

"Miss Marcia, you won’t have to wait that long. The two of you have been receiving a small dose of hormones per day. We increase the dosage here, in about 18 days your breasts will start making their appearance. Now, Miss Roberta it is time for me to put you in your corset. Please strip down to your birthday suit. Then put on the clothes you find on your bed."

Marcia looked on as Roberta stripped. When she got her first look at Roberta breasts. She noticed that the nipples were spreading out. "Will my nipples be as large as Roberta’s, Ms. Stoneman?"

"Could be, it depends on how Mother Nature decides how to do it."

As Roberta put on the top and then the old fashion bloomers, she noticed that near the bottom of the legs, there was a thick plastic strap attached to each leg. "Ms Stoneman, why is there a strap attached to legs on my bloomers?’

"We use the strap to control the length of your step. Miss Roberta if you notice most men and boys take a very long step. Where as most women and girls take small dainty steps. So the straps will teach you girls how to walk like a girl. The strap will stay on, until walking like a lady becomes natural to both of you."

Then the corset was put on. Roberta noticed a flap down at the bottom. Ms. Stoneman noticed Roberta’s look. "That flap will stop your piece of manly equipment from showing. Now, hold onto the bedpost. So I can tightened it up good and tight."

Five minutes later, Roberta was tied up in her corset, barely able to breathe. "If you take short breaths, It will make the corset wearing easier.

Ms. Stoneman started Marcia and Roberta doing things, to get used to their corsets. Sitting, walking, laying on their beds, even bending over. "You’ll just have to learn the correct way of picking up stuff from the floor. Now sit on the bed and I will show you how to put on your shoes."

"We know how to put on a pair of shoes, Ms. Stoneman."

"You do, wearing a corset." Both girls shook their heads no. "I think we will start both of you off with 2 inch heels."

Both girls spent the next ten minutes learning to walk all over again, with short dainty steps and in heels.

Then came a knock on the door. It was Pamela again, "Ms. Stoneman, Brigitte is ready in her room."

Both Roberta and Marcia looked at each other. Brigitte must one of the other two girls in their group.

Turning to the girls Ms. Stoneman said. "I want the two of you to sit down and start reading the rule book. You can talk with each other but I want you to stay in your chairs. I’ll be back when I have Brigitte and the other girl dressed up like you are, then I will come introduce the four of you."

As both girls started to read. It wasn’t very long before they started talking.

"Why did you picked the name Roberta," asked Marcia.

"I didn’t really. When Jennifer caught me in her clothes, she started calling me Roberta, and mom just started doing the same. But I am going to ask Ms. Stoneman if there is a way I could change it."

"Why do you want to change it."

"When I signed the letter of agreement. Mom gave the middle name of Vanessa. She told me, if I was born a girl. It would have been my name. So I think I would like to be Vanessa. My question, why Marcia?"

"Remember, I have always had a crush on Marcia on the Brady Bunch. So there was really no choice in the matter. Marcia is the name I like so Marcia I am."

"I think we better get on with our reading. I don’t want to flunk that test tomorrow. Or any test for that matter. I don’t to give them any reason for kicking me out."

"Neither do I. Let’s make a deal. You help me and I’ll help you. This way we can help each other this year."



As we end this chapter in Roberta’s life. Maybe soon it will be Vanessa’s life. She has found a place where her dreams of being a woman can come true. Then finding an old friend to share the experience with her.

Look for the next chapter in Roberta’s Life at Miss Lynne’s



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