Crystal's StorySite

This is a little spin off story from Maggie Fights Back. Involving Deanna’s friend Jennifer and her family.


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


"MOM, come quick," screamed Jennifer. As she walk into her room.

The reason Jennifer screamed was, she found Robert, her fourteen year-old brother, in her room. Robert had thought that Jennifer had left for her friend Deanna’a slumber party, and he decided to have some fun, in her room.

Jennifer had forgotten something and had to come back.

What she found was Robert wearing one of her bras and a pair of panties, and in the middle of applying some lipstick.

Robert tried to get undress. "No! Robert, or should I say Roberta. I want mom to see you just the way you are."

"Please, Jennifer let me change. Please!" Robert begged.

"No! I want mom to see you this way." Then they both heard the footsteps. They knew there would be no more arguments.

An utter look of shock came upon Mrs. Long’s face at what she found when she came into the room.

"Robert! What are you doing?" Jessica Long knew this was all Robert’s doing. She knew that Jennifer just came home.

"I can explain, mom," Robert stammered.

"Go ahead young man, or should I say young lady."

"Give me a minute to get out of these clothes." asked Robert.

"No, I want you to stay in them. Jennifer why don’t you give our little Roberta that simple house dress of yours, to cover herself with."

As Robert put on the dress, he started to explain.

"I Can’t Help Myself. Six months ago, I got to wondering what it felt like to wear a bra and panties. So I came in here, when both of you were gone and tried them on. Ever since then, I have had to wear them at least once a week. If I don’t, I feel so sick until I do. I have tried to stop, but I can’t."

"I have noticed lately that some of my panties didn’t look and feel right, and I noticed that they weren’t in the right places," Jennifer added.

"Have you told anybody else?" asked Jessica.

"No! How could I." replied Robert. "I haven’t even have enough nerve to wear this stuff outside. Cause of my fear of someone finding out."

"I understand Robert. There are things that happen to each of us we can’t control. Like my smoking, I want to stop but can’t. All I ask for now Robert is to give me a couple days to figure something out. But I also don’t want you to wear anymore of Jennifer’s clothing. Now get out of Jennifer’s clothes."

With this Jennifer went to Deanna’s slumber party. She is a cousin to her ex-boyfriend who had moved away, Deanna moved in with her aunt, to keep her company. Cause of a bad situation at home.

Deanna and Jennifer went to separate schools, Jennifer to public and Deanna to private. Cause Maggie, Deanna’s aunt wanted her to start public school at the beginning of the school year.

At the party were seven teenage girls, three went to school with Jennifer and two went with Deanna, their names were Veronica and Patricia. Three of them attended Ms. Lynne School for Young Ladies.

The party went like all girl’s slumber party, talking about boys, clothes, and more boys, cooking and more boys. After a while Jennifer had to visit the powder room. As she slipped into the room she noticed that Deanna was already using it. No problem with that, Jennifer thought. Until Jennifer got a shocked of her life.

As Deanna stood up Jennifer notice that between Deanna’s legs was a man’s cock. Not a very big one, but still a cock.

Deanna slipped on her girdle and left without noticing Jennifer.

While Jennifer sat and did her business she started talking to herself. How can this be? Why is there a cock between Deanna’s legs? She asked herself a lot.questions. Until she realized the only answer.

Dean hadn’t moved away, as his mom said. But had been transformed into a girl. What a story I can tell everybody. That old bully and ladies man, now is a girl.

No I don’t want to do that. I never liked Dean, but I do like Deanna. As a friend I should learn to live with this, and help Deanna as much as I can. Yeah! That is it. It will be Deanna’s, Maggie’s and my secret.

I wonder. If Deanna is a boy, and she attends Ms. Lynne school. What about Veronica and Patricia. Are they boys too?

I think it is best that I talk to Maggie about this, alone. I want to wait before I say anything to Deanna. That is what I am going to do. With this she went back to the party. She had been gone for 45 minutes. Patricia piped up. "Jen, you were gone so long we thought you fell in."

"No, nothing like that."

There was no problem the rest of the night. It was a normal girl slumber party.

Jennifer just made sure to find out when Deanna made it home from Ms. Lynne’s. Jennifer found out there was an hour where she could come over and talk to Mrs. Courtland without Deanna finding out.

The following Monday, Jennifer called Mrs. Courtland.

"Mrs. Courtland, this is Jennifer."

"Hi, Jennifer, is there a problem?" asked Maggie. Thinking something might have happened Saturday night.

"No, not really. I just would like to come over and talk to you."

"No problem, Deanna won’t be home until 4:30."

"I wanted to talk to you before Deanna came home."

"Is there something I should know about?"

"No, I just wish to talk you. I’ll try to get there as soon as I can."

"Okay, see you then."

At 3:45 Jennifer walked into the Courtland house.

"Mrs. Courtland, I don’t know how to say this, so I am just going to say it."

"What is that you want to say."

"I know the truth about Deanna. She didn’t tell me. But I entered the bathroom as she finished using it, and I saw her body before she replaced her girdle. She didn’t see me."

"So you know Deanna’s secret. May I explain what happened? I do have one question first."

"I haven’t told anybody yet. If that is what you wanted to ask. Also I have figured out that Dean and Deanna are the same person."

"Do you remember what my life was like eight weeks ago?"

"Yes! Mr. Courtland was trying to force you to divorce him. I remember Dean telling us what he was doing to you. That is one of the reasons I wanted break up with him. One of the reasons was I had trouble with what he was doing to you. What would he do to me."

"I found a company that help women like me. Using hypnosis they make some changes to people. So I changed Dean into Deanna. You remember the day Dean told everybody about his Uncle Paul. He was under hypnotic control that day. We used that day to help explain his disappearance. He went directly from school to Women’s Help Corp. Where she stayed until the day we meet you at the mall."

"You mean Deanna has been under hypnotic control since then."

"No, I haven’t used any controls since three days after our meeting. Deanna likes being a girl so much. I would bet even if she has a chance to go back to being a boy, she wouldn’t."

"What happened to Mr. Courtland? Did he just leave town."

"No, he is still undergoing treatment at WHC. I won’t tell you what is happening to him. All I will tell you is it isn’t very nice."

Maggie stared at Jennifer then asked. "Since you know Deanna’s secret, what are you going to do about."

"Nothing, Nothing at all. I made a decision Saturday. I would rather Deanna as a friend than Dean, any day of the week. I just wanted you to know, I knew. I want to help, any way I can."

Maggie got up and hugged Jennifer. "Thank you. You had me worried for a moment."

"I do want to ask for one thing. You might be able to help me and my mom with a problem we have."

"What it that?" asked Maggie.

Jennifer then explained what happened at her house, before the slumber party.

"I don’t think Roberta needs hypnosis. She sounds like she already likes being dressed as a girl."

"What about Ms. Lynne’s school. I don’t think it is a school just for girls, is it."

"You’re right there. It is a school for boys who want to be girls. It is a school that trains these boys to be girls, so they can live in the outside world without someone finding out the truth. 95% of the students are boys who want to be girls or already have become girls."

"You mean some of the boys have had a sex change operation?"

"Yes, you remember Patricia and Veronica."

"Yes, I do"

"Pat, has already had her operation. Veronica hasn’t yet decided what she wants to do yet."

"Whoa, that is amazing. I would have never known. What about Deanna?"

"Shortly after school is over, she will have her operation. That is when I think she will need your help the most."

"You can bet the house, on me helping. I think I better leave. It is 4:25 and I don’t want Deanna to see me. Should I tell Deanna that I know?"

"No! Not yet. Let’s wait until after her operation, and then I will tell you when."

"I’ll wait, Goodbye Mrs. Courtland."

"Jennifer, THANK YOU."

Jennifer didn’t get home until supper time. What she found surprised her. Her brother was helping her mom. With cooking and setting the table. He hadn’t done this since he was ten.

What shocked her even more, was the outline of a bra showing through the back of Robert’s shirt.

"I thought mom told you not to wear anymore of my clothes."

"I am not."

"Then what is this?" Jennifer asked as she reached over and snapped the bra Robert was wearing.

"My training Bra, I am even wearing a pair of panties. Mom bought them for me today." Robert lifted his shirt to show Jennifer his training bra, even pulled his pants down enough to show off her panties.

As Robert did this Mrs. Long came into the dining room. "That is right, I did buy some stuff for Roberta today. Let me explain, after dinner.

After dinner was over. "Roberta, I want you do the dishes while I talk with Jennifer."

"Yes, mom."

Jennifer turned to her mom. "I have noticed that you have been calling Robert, Roberta since I came home."

"I have, and so will you. I want you to call her Roberta as long as she is wearing anything feminine, okay."

Sitting down in the living room. Jessica started talking. "I have been doing a lot of thinking since Saturday. Thinking over what we can do and what we must find out. So I decided to find out if Roberta is just going through a stage, or is it more serious. So I decided to buy her some clothes, and see how long she will go with them. If it is a stage she will be out it by Summer. If not I have to do some more thinking."

Mother and daughter did some more talking until Roberta entered the room. "I finished the dishes, is there anything else you want me to do?"

"No I don’t, dear. Why don’t you talk with Jennifer some? Tell her about this afternoon. While I do a little work."

As their mother left, Jennifer turned to Roberta. "So what happened?"

"I came home like I normally do. When I cam through the door, mom called out and said she wanted to see me in her room. When I got there she told me to strip. Still wondering what was going on, I did. Then she told me to hold my arms straight out towards her, I did. I felt her sliding something up my arms. When she hooked me up. I knew what it was.

"She then told me to turn around and open my eyes. I found myself staring at myself in her mirror. I was wearing a bra, one without cups. It felt so good. She then said. ‘This is a training bra. Girls wear them before their breast start developing. Most mother’s dream of the day they help put on their daughters’ first bra. I guess I will have to make do with helping you with your first training bra.

"Is this bra for me, I asked very hesitantly. Not wanting to hear the answer. Yes, it is, I have bought four of them for you, also I bought a dozen panties. I almost fainted. Then she told the rules.

"I can only wear my bra and panties when I am at home. At no time will I wear them outside, no excuse will be accepted if I do. I can’t wear them if there is a chance of anybody finding out. During the time I am wearing them I will be referred to as Roberta, or a feminine form. Since I am a girl I must act like one, like helping with dinner and dishes. At any time I must not do anything that might be considered masculine."

Jessica then walked into the room. "I also promised Roberta that the change would become more permanent if she decides if this is what she wants. Roberta, I just got your bubble bath ready, so why don’t you go take it. Then come down when you are ready for bed."

"Mom, I might have the answer to your promise," Jennifer said after Roberta left the room. "But I need to make a phone call first."

"Make the call, I can’t wait to hear on how you can know the answer," Jessica watched her daughter go into kitchen.

Jennifer called Maggie. "Mrs. Courtland, this is Jennifer can we talk?"

"Yes we can, Deanna just started her bath."

"I would like to tell my mom about Dean/Deanna," Jennifer went into the details about what had happened with Roberta. "I think Miss Lynne’s School would be perfect for Roberta. If mom and Roberta decide to go further. I just wanted to make sure if it is okay with you first."

"I trust your judgment. Your mom was one of the few ladies who supported me when I needed it. Make sure you remind her I don’t want Deanna to know, that anybody knows about her."

"Thank you."

Jennifer then returned to her mom.

"Mom, you won’t believe this. Do you remember Dean Courtland, my old boyfriend."

"Yes I do, it has been only six weeks since he left."

"Dean didn’t leave. He is still living with his mom."

"No he isn’t. The only person living with Maggie Courtland is her niece, Deanna. You should know she is your best friend."

"That is where you are wrong. Dean still lives at home. You see Dean and Deanna are the same person."

"What! You have to be kidding. Deanna is so feminine, I was hoping some of her femininity would wear off onto you."

"Let me explain. I just found out most of this information this afternoon. That is where I was after school. That was Mrs. Courtland I had to talk to. I promised her I wouldn’t tell anybody about Deanna. I wanted her okay before I told you. She said yes."

So Jennifer went into all the details. Explaining the WHC, Miss Lynne’s School, then the slumber party.

"WOW! I didn’t know these places exist. I heard rumors, but nothing concrete. Do you mean you have met a girl who was actually once a boy."

"Yes, I couldn’t tell the difference, not between my friends from school or those from Miss Lynne’s. The only reason I found out, was because I caught Deanna in the bathroom."

"Does Maggie think Roberta needs some help from WHC?"

"No she doesn’t, because Roberta wants to be a girl."

"I think I will talk with Maggie tomorrow and go into more detail."

They heard Roberta leaving the bathroom. She entered the living room. Instead of wearing his normal PJs Roberta was wearing a pink baby doll nightgown, which barely came down to the top of her legs, and matching panties. "Mom, told me I could wear this, if I wanted too." Roberta went and kissed her mom good night. She then turned to Jennifer and pecked her on the cheek. Like two women did. "I am not sure if I did that right, I hope so."

"It was okay."

Roberta then left for bed.

Jessica then said, "I think I will get the address and phone number for Miss Lynne’s from Maggie. Cause I don’t think Robert Long doesn’t live here anymore, Roberta Long does."

Jessica and Maggie met the next afternoon. Jessica explained in more detail, on what had transpired at her house.

"I think it is great that you want to help Roberta, and I will help in anyway I can. Here’s the phone number and address of Miss Lynne’s. They are expecting your call."

Jessica made the call, right there and then. An appointment was setup for the next day.

At Miss Lynne’s School for Girls, Jessica was escorted into the Headmistress’ Office.

"Mrs. Long, I am glad to you. My name is Lynne Snobgrass. Mrs. Courtland called and explained your situation. Yes, we would love to help."

So the two ladies talked for an hour.

Lynne said. "I do like your idea about testing Roberta’s will for the change. I hate finding out halfway through the process that a transformee has changed her mind.

"Here is what I would like you to do. Till school lets out, continue to do the same as you are doing. After that, if Roberta still wants to be a girl. I want you start giving her a small amount of hormones. Not a lot. By the time September rolls around Roberta’s body will look more feminine. Her breasts will be just starting to make their appearance.

"Then right before school starts you’ll bring her here."

"We like to have all of our girls live here on campus. This way they are under going their training 24 hours a day. And there’s no chance of somebody noticing the changes.

"Two months after school starts. Roberta will be given the choice. 1 being a girl body and soul. Or she can keep the last piece of male equipment. 85% of the girls who come here are willing to have the sex change operation. We have found out over the years that there are some girls who are not ready for that final step."

"How do I get these hormones?" asked Jessica.

"From the school’s physician. She is also a trained psychoanalyst. So she will have an opinion about Roberta. Here is her name. I suggest you call her."

Jessica and Lynne talked for another hour.

By the time summer rolled around. Roberta was showing no signs of wanting to go back to being a boy. She even had Jennifer helping her be more feminine. Even the doctor agreed that Roberta really wanted to be a girl. So Jessica started the hormones, telling Roberta they were vitamins.

By the end of summer vacation the hormones had the desired effect. If you took a very close look at Roberta’s chest you can see her breasts just starting to push out from her chest.

Even Roberta noticed. She asked her mom. "Look mom, do you know what is happening? Wearing a bra must be doing something to me, I’ve grown breasts."

"Don’t worry about it. It is a passing phase."

"What will the guys say in gym class when they see me with breasts?" asked Roberta.

"That won’t be a problem. I wanted it to be surprise, but you’ll be attending a private school this year. They have their own uniforms and such and that is why we haven’t gone shopping for any new school clothes."

"A new school, why?"

"Remember when Roberta first came to live with us. I promised her something special."

"Yes, I do."

"This is it. Tomorrow I will take you there. I won’t be taking Robert, I will be taking Roberta. That is right, I want you to wear a dress, with all the trimming, make-up and tonite Jennifer and I will put your hair in curlers so it has a more girlish look to it."

"What will they think of me at this new school."

"I don’t think there will a problem. That is why this school is so special."

All during supper and afterward Roberta kept asking questions about her new school but all she got was the old answers.

"Don’t worry you are going to love it. You won’t have to worry bout anybody finding out about your secret." So on and so on.

"Roberta, I am so glad you haven’t gotten a hair cut since last April. We can really make it look so beautiful for your appointment tomorrow." Jennifer said to Roberta, that night.

Roberta wasn’t sure why, but she couldn’t sleep that night. Maybe it was the curlers or of the unknown that tomorrow will bring.

Roberta finally got to sleep around 3 in the morning; the alarm clock went off at 7.

Roberta found both her mom and sister in her room when she woke up.

As she watched, Jennifer unrolled the curlers. Roberta couldn’t help notice how beautiful her hair was in the new feminine style. It was almost the same hairstyle in the dreams she had been having.

Now she removed her nightfown. Jessica said something like. "I don’t think your breasts are large enough for an A cup bra, so we better just use your training bra for today."

Roberta asked. "Do mean my breasts are almost large enough for a regular bra."

"You’re just not large enough yet. We don’t want your bra just to hang there," Jennifer replied.

After Roberta slipped on her panties, Jessica pulled out a slip, which she helped pull down her younger daughter’s head. "You’ll need to wear a slip with your dress." Then came the dress. It was one of those that were tight from the shoulders to just below the bust. Then it hung loosely below that point. Roberta noticed after her mom zipped her up. The dress didn’t hide the fact that Roberta had breasts. When she looked down, she could see them pointing out. Then came the knee socks. Jessica said, "you aren’t quite ready for panty hose." Then at last the Mary Jane’s.

She then turned to Jennifer. "Why don’t you put on Roberta’s make-up while I finish dressing. I know she can do herself, but I want everything just right."

Roberta tried to sit down facing the vanity mirror. "NO, Roberta I don’t want you to see yourself until I am finished." Then came the rouge, mascara, eye shadow, and then the lipstick. "I would like to pluck your eyebrows, but we don’t have the time."

"Don’t look, I want mom to be here for your first look."

A minute later Jessica came into the room. Jennifer then led Roberta to a full-lenght mirror. "Now, Roberta take a look."

Roberta finally got a look at the new her. She just there for two solid minutes looking up and down at the reflection in the mirror. Finally she said something. "That can’t be me. I am Beautiful!"

"Yes you are." Jennifer and Jessica said in unison.

"Now let’s go. I don’t want to be late for the meeting."

Roberta left the room with her head in the clouds, saying to herself. "I must be dreaming, and I don’t want wake up."


Look for the next chapter in the Roberta story.
Roberta at Miss Lynne’s School for Girls



The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.