So-Called Friend             by: Jennifer Allison

 

Part 5

 

Billy and I had to lay back and rest for a few minutes.

Finally I said, "it's time to make your fantasy come to life."

I went over and covered my vanity mirror.

"Why did you do that?"

"I didn't want you to peek until I am done. It will ruin the effect."

"I'll put myself in your capable hands."

As I trimmed Billy's eyebrows. "I hope you don't make them to feminine."

"No just a little unisexual."

Then came the face powder followed by the blush. I could see what effect I was having on Billy. His woodie told me.

"It looks like you like the idea of becoming my girl."

"I guess I do?"

"Have you ever thought of becoming a girl full time. I don't mean. Dressing up like a girl. I mean a girl with breasts and a pussy."

"Sometimes, I wonder what it would be like. My mom and dad would have a fit, if they ever found out what I am doing right now."

"Anything can happen Miss Wilma."

"Why did you call me Miss Wilma?"

"If you are going to be a girl you need a more feminine name. I think Wilma suits you."

"I like it. But why did you call me Miss Wilma?"

"All the students at my school are call Miss. The instructors are called Ms."

"You go to an all girl school?"

"Sort of. I'll tell you more about it later. Now I have a question. Do you want me to make you look like a school girl or more like a hooker?"

"I'll leave it up to you."

"School girl this time. Since it is your first time. Next time a hooker, okay?"

I finished the mascara, lipstick and eyeliner. Still wanting not to spoil the moment I kept the mirror covered. "Now I want you to close your eyes until I tell you to open them."

I then had Wilma slip on a pair of panties. Then a babydoll nightie, which barely hid her panties. Then came the wig, it was reddish/brown in color.

I then moved Wilma over to the closet's full-length mirror.

"You may open your eyes, Miss Wilma."

For two solid minutes Wilma stared at her reflection. "This can't be me, I am beautiful."

"It is you."

"Why did you dress me in white?"

"You are still a virgin."

"No I am not."

"William isn't a virgin but Miss Wilma is. We will soon take care of that."

 

"Now on your knees you high school slut. Open up your red fuckable lips so I can feed you this dick that will take away your maidenhood."

Wilma fell to her knee and took the dildo in her mouth.

"We want it all wet and slobbery so it will slide up your ass as wet as a whistle. Come on suck like you mean it.

"I SAID SUCK ON IT!!!!"

"That is a good girl. Keep it up for a couple more minutes.

"Now get on the bed face down. With your butt in the air. It is time for me to turn you into that girly slut you were meant to be."

As I applied the KY-gel. I tried to soothe Wilma a little. I knew from my experience that she was very tense.

"It will hurt at first, but when your butt accepts the dick all you will feel will be pleasure and no pain. The pain you went through will be all worth it."

Before she could react I slammed that dildo up her ass.

There was a scream of pain. Then followed some crying. Then all of sudden the noise changed from crying to moaning as I felt her trying to meet each of my thrusts.

Finally Wilma said something I could understand. "Come on, faster, faster put that dick deep inside me. I am cumming, cumming!" I kept it up until Wilma had at least four orgasms.

By the amount of cum on my sheets, she must have shot at least three loads.

As I pulled the dildo out. Wilma rolled over and smiled at me. Then fell asleep. I guess the excitement was too much for her.

This gave me time to go out and talk to my step-mom and Wilma's mom.

I found them in the living room playing gin rummy. The other two moms had left when they found out I had picked William as my partner.

"May I talk to you?" I asked.

"Question first. Did you do what you were supposed to do?" asked my step-mom.

"Yes I did."

Then I went on to describe what had just taken place.

"You mean William is asleep in your bed in a nightgown and make-up?"

"Yes."

"I can't believe it. I thought I would have to fight tooth and nail to get him to do this."

"I do have one request though."

"What is that?"

"I would like to be the one to tell her. It might be easier that way."

My step-mom agreed and so did Wilma's mom.

"You realize she might hate you for the rest of her life?"

"Yes I do."

 

Wilma was starting to stir as I reentered my bedroom.

I sat down and waited for her to become fully awake.

"That was incredible," were the first words out of her mouth.

"Why don't you put your panties back on. Then I would like to talk."

"Why do we have to talk. You're not pregnant are you."

"No, I am not. There is no way I can be pregnant. That is one of the reasons we need to talk."

"What is it you want to talk about."

"First off I want to tell I didn't want to do it this way. But my step-mom and your mom left me no choice."

"What do you mean? my mom. Does she know what we just did?"

"Everything, including the way you are dressed right now. I told her while you were asleep. The other guys' moms were here earlier. Waiting to see who I would take to bed with me."

Then it dawned on her what I said. "What do you mean. Calling your aunt your step-mom?"

"It is very simple. She is my step-mom."

"Hold on there. I know this family. There is only one child, and he went off to a private school eight months ago."

"That's right, I did."

It finally dawned on Wilma what I was saying.

"DEAN! It can't be you. You are a girl."

'That is right I am a girl, but eight months ago I was your friend Dean."

"What happened? How? Why?"

"I was setup by our So-Called Friend John. He convinced me to try a little experimenting with a little man on man sex. As John was butt fucking me. My step-mom walked into the room. It seemed it had been a setup. After she showed the tape they had made of John and I to my dad. I was sent to Ms. Singleton's."

"What's Ms. Singleton's?"

"It is a school where boys are sent and then transformed into girls. Some under go the sex change operation like I have. Others are allowed to keep their dicks, but everything else is all girl."

"That is hard to believe."

"I am not the only one John has done it to. Do you know the new girl in school named Donna?"

"Yeah, I was going to ask her to the dance next week."

"She attended Ms. Singleton's. A year and a half ago she was our friend Bruno."

"Why are you telling me all this?"

"I don't know how to say it but I am just going to say it."

"Go ahead and say it."

"Starting Monday you will be attending Ms. Singleton's."

"My folks would never do that to me."

"I don't know about your dad, but your mom is all for it."

"Why me?"

"That is where I come in. You see one of the requirements is that I am to have sex with a boy a couple months after my surgery. My step-mom set it up with John's, Tom's and your mom. The one I took to bed would be attending Ms. Singleton's."

"Then you set me up, just like John did to you."

"I didn't have a choice. It was going to be one of you. Remember how I left the pool area for a little while. I went and tried to talk them out of it, no such luck. Then I had to make a choice. From what I heard by the three mothers one way or another that all three of you will be sent to Ms. Singleton's eventually. I picked you, for a very good reason. It is a lot easier to make it through Ms. Singleton's if you have a friend there. Since I will be there for at least four more months. I will be able to help you through it."

"You mean it is that bad."

"Not as bad you might think, I cried myself to sleep many a night. Donna was there to help me through it."

For the next five minutes Wilma just sat there. Not saying a word, but deep in thought. Then finally she said something.

"You know I have always wanted to see what was on the side of the fence. I was always afraid to tell my folks. Now that I have my chance I going to take it."

"You mean you want to become a girl?"

"Yes I do. I want to become a girl with all the right equipment."

"That will be up to mother, I see no problem there. She probably will be so happy that you have accepted this, that she will go with your wishes."

"What do we do now?"

"I have an idea."

 

An hour and half later. We went to supper Wilma and I.

As I walked into the dining room Wilma's mom asked. "Where is Billy?"

"She will be here shortly."

"I hope he is here before supper."

Finally my step-mom ordered Roberta to start serving.

You should have seen the look on their faces when a second maid appeared behind Roberta. In full uniform, including two-inch heels.

"Miss Wilma has asked to serve you tonight Ms. Marston."

Both mothers stared at Wilma as she walked around the table. As Roberta and Wilma returned to the kitchen.

"How did you do it?" Ms. Marston asked.

"Wilma has always been there. But she has been afraid to tell you."

"Why do you call her Wilma?"

"That is what I started calling her and she liked the name."

"So do I. Have you told her about attending Ms. Singleton's?"

"Yes I have. She also wants to ask for something."

"Miss Wilma would you please come here."

 

Wilma then came back into the room.

"I heard you want to attend Ms. Singleton's?"

"Yes I do. I would like something else too, if I can."

"What is it?"

"I would like to become all girl like Deanna. Also I would like to spend the weekend here with Deanna."

"Doing what?"

"The same thing we have done this afternoon. Fucking each other brains out."

"That's okay with me as long as Deanna's mom don't mind."

"I see no problem."

"As for the other part. It has already been arranged. In six months you will have a pussy just like the rest of us."

I lost count how many times we fucked each other that weekend. My step-mom didn't forget my duties just because I had a guest. I was the maid and serving girl to all three my step-mom, Roberta and Wilma.

 

The following Monday in my Woman's History class a new student was introduced.

She stood there with a very large smile on her face, in clothes meant to be worn by a six year-old with two earring in each ear.

"Girls, I would like to introduce a new student today. A Miss Wilma. Miss Deanna I have heard you have assigned to help Miss Wilma."

"Yes I have."

 

I never was able to get my revenge with John. John and his mom left the house shortly I left with Billy. Three months he fooled around with the wrong person. He ended up HIV positive.

As for Tom, he ended up at Ms. Singleton's three months later. It seemed his boyish charms didn't work on a certain girl. She cried rape. To stop them from sending Tom to jail they decided sending him to Ms. Singleton's was a better idea. There were two additional punishments placed on her too. After her time at Ms. Singleton's Thelma has to spend the next six years as the girl's personal maid. Thelma was allowed to keep her penis, but unfortunately the only thing it was good for was taking a leak.

 

 

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© 2001 by Jennifer Allison. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.