Learning to Change - Part 2

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Chapter 2

“What is that?” I asked worried about the flash I just saw.

“Nothing, just a photo, you look very beautiful in that dress” She answered.

“Please erase it, I don’t want anyone to see it”

“Don’t worry, I’ll keep it just for me, I won’t show it to anyone” She said smiling.

“Aren’t you angry?”

“Just a little, you should’ve told me you liked girl’s clothes before, I could have lend you some” she said kindly. I was a little confused, I thought she would be mad.

“I´m not sure I like girls clothes, I was just curious” In fact I did like the clothes, but I didn’t want her or anyone else to know.

“You don’t have to lie, you know, I can keep the secret” She told me “I can see in your eyes that you enjoyed it”

“Ok, I liked it, but please, keep this a secret, I don’t want my parents or anyone from the school to know” I said, still a little scared of what she might do with the photo.

“You can keep the underwear if you like, the dress and pantyhose return them”

“Really?” I said surprised “Thank you”

“Yes, I have some more old clothes in my house if you like. They should fit you well”

“I don’t know about that, where would I keep them? I don’t want my parents to know”

“We´ll figure that out later”

“Fine, I’ll go to my room and change to my clothes”

“But why? Don’t you like being in these?”

“Yes, but my mother will be home in an hour or two” I started to walk out of the room.

“Alright, but you can keep the underwear on, they won’t see it” She said.

“I guess I can” I went into my room and took the dress, bra, and pantyhose off, but kept the thong. I put my clothes on, and hide the bra inside a drawer, and then went to the bathroom to wash the makeup. I took the dress and pantyhose, and walked to Vanessa’s room.

“Hey, here’s your dress, and thanks for not getting angry, I know I shouldn’t have entered your room without your permission” I told her regretfully.

“Don’t worry, just don’t do it again” She said as she was looking at her laptop “Did you keep the thong on?”

“Yes” I said, lowering my jeans a bit to show it “It feels a little weir between the cheeks, but I think I can get used to it”

“I know what you mean, it took me some time to get used to it too. Come on in, I want to tell you something” she left her laptop besides her. I entered the room and sat on the bed “Tomorrow we can go to my house for the clothes, you can keep them in a box under your bed. Also, I will teach you how to put on makeup”

“I would love that, thanks” I said smiling.

“And maybe we can go shopping for some clothes for you another day”

“I don’t think so, that would be very expensive”

“Don’t worry about the money, I have enough for everything”

“How do you have that much money?”

“That is my secret, sweetie” she said.

“Ok, thanks again for being so nice about this” I said and then walked out of her room. When it was night I had trouble sleeping. I was looking forward for tomorrow, having more girl’s clothes. This was going a bit too fast but I liked it. It was exciting discovering this new things.

When the next day arrived and my parents left, Vanessa came to my room and told me that we should get going. She called a taxi and we left to her house. When we arrived, she directed me to her room, it was bigger than mine, didn’t look very girly but it was very organized. She opened the closet and in the corner she had a box full of clothes. She took it out and opened it.

“I was going to give them to a clothes charity or something, but I guess giving them to you is fine” She took the clothes out and put them on the bed. “You should try them out”

“Ok” I took a plain black skirt and a white blouse and was headed out when she stopped me.

“You can change here, don’t be shy, I’ve already seen you almost naked” I didn’t say anything. “Come on, do it, or do I have to make you do it?”

“Ok, just don’t laugh” I took my shirt off, then my pants and socks and I was left with just my boxers.

“I thought you were going to come with my underwear on?” She said “I’ll give you another pair” She took a black bikini and a bra from a drawer near her bed and gave it to me. I hesitated before pulling my boxers down but finally, I did. She giggled a little when she looked at me.

“I told you not to laugh” I said angrily.

“Sorry, it’s just, I have never seen a penis that small” She took a ruler out. “Let me measure it”

“What? No?” I said with my face red of humiliation.

“If you don´t let me, I will publish your photo in my dress for everyone to see” I was silent for a few seconds, I couldn’t believe she was threatening me, after acting all nice. But what could I do? I couldn’t let her publish that picture.

“Ok, but do it fast”

She came close to me and put the cold ruler on my penis “It is 3.5 inches, it isn’t hard, is it?” I didn’t answer “By your silence I’ll guess it is. That’s why you didn’t had a problem fitting in my undies” She said laughing a bit “Put the clothes on now” I pulled the bottoms up, and put the skirt, then the bra, and finally the shirt. “You look very nice, almost like a girl. Your short hair gives it away though” There was some silence “Come on, say something”

I tried to calm down “It’s ok”

“If you are not talking much I guess we better head back to your home” she said a bit angrily.

“Just let me change”

“Fine, but one day you will have to go out with girl’s clothes”

I changed back and we headed home. On the way back neither of us talked. I was really angry she used the picture to blackmail me, I guess she could do it again, I better find a way to get rid of it.
When we arrived I took the box and put it under my bed. I was going to watch some TV when she called out for me. I went upstairs to her room.

“We need to talk” I nodded “I have some rules you need to follow from now on”

“What are you talking about?”

“If you don’t want me to put your picture online, you will have to do as I say” I was shocked by her words “Every day after your parents leave you will have to dress as a lady and put on makeup One hour before they come back, you will change back. So you don’t have any trouble with them. Do you understand?”

“You can’t do this”

“Yes, I can, you saw the picture”

I tried not to show my anger “Fine, but I don’t know how to put makeup on?”

“Don’t worry, I will teach you starting tomorrow morning” she said “the day after tomorrow we will go to the mall to buy you some underwear and makeup, I don’t want you using mine, ok?”


“Hey, I don’t want you to be mad at me, I am doing this for you. How about I help you with the girl you like, Melissa, would that make you happier?”

“That would make me happy” I said smiling.

“Ok, give me her number and leave me for a moment” I did and she said. After a few minutes she came out of her room and told me the good news “She said she would like to go out with you this weekend”

“Thank you” I replied. Much happier with her but still a bit angry.

The next day after my parents left she walked to my room and told me she would teach me about make up. I followed her to the bathroom. She was still wearing her pajama, a short and a light white top.

“First of all, your face should be clean” I washed my face “Then you have to apply foundation on it. It has to match your skin tone. She stood in front of me and applied it. Then we put some shadow around your eyes, eyeliner, and finally some blush and lipstick” While she was doing this, I could see her nipples through her top. Her breast weren’t very big but they were firm. I was hypnotized with them. When she finished she looked at me “You look very pretty”

I looked at myself in the mirror all I could see was a girl I didn’t recognized. It was me. I indeed looked pretty.

“Now go and put some clothes” I went to my room, took out a short and a red top. I changed and looked myself again in the mirror. I looked girly in the face but my body still lacked the curves of a female one. It made me a little sad, being so close to look like a girl but not quite yet.

“Why the sad face? I thought you liked being in girl’s clothes?”

“I do, but I don’t look like you? You have a perfect body I wish I had?”

“So you’re jealous”

“Yes, but there’s nothing I can do to change that”

“We’ll find a solution for that, don’t worry. For now, try to enjoy the clothes and that pretty face you have. Tomorrow we will go to the mall. I’ll buy you some things I hope make you happier. And remember that on the weekend you have a date with Melissa”

“Thanks” I couldn’t believe how nice she was being with me.

On Thursday we both woke up late. I dress normally. She at first wanted me to use a dress, but I refused. It was already 1 o’clock when we took a taxi to the mall. It wasn’t very crowded.

“First we have to go to buy you some undies” we went to a shop with the front all in pink. I was nervous about entering there. I was shacking a little and Vanessa noticed. “You don’t have to be scared, no one will know we are buying them for you, they’ll think they are for me, remember we are the same size”

“I guess you’re right” We entered the shop and she started to pick underwear. I just followed her around. Then she stopped.

“Do you like them, If not just tell me” I took a look at them. They were all very cute, with varying colors and forms. There were bikinis, thongs and others were something in between.

“They look good” I said “I trust you”

“Now, we have to get some bras” again she picked some, but this time she asked a lady “excuse me, is it ok if I try this on?”

“It’s fine, you can try them on there” the lady pointed to a changing room at the back.

Vanessa took my hand and led me to the room. She then ordered me to take my shirt off and I did. “We have to find the right size for you, so try this one” After I tried it on she said “It is a bit loose” She handed me another “this one fits you better, we will choose some with a small cup, because you, clearly, won’t fill bigger ones”

I felt a bit hurt by the commentary she made but she was right, so I smiled and said “Thank you so much, this means a lot to me” We then proceeded to the cashier. To pay, she took a credit card out of her purse. After that we leaved the shop. “Were did you get the money to pay for all of that” I asked.

“You don’t need to know that” she answered with a serious voice. “Anyway, we need to go buy you some makeup” The visit to the cosmetic shop was faster. She picked everything I would need and pay in just a few minutes.

“We should get something to eat, do you have some suggestions” she asked me.

“I think you should decide, I’d eat anything right now”

“I was thinking about Chinese food, what do you think?”


We went to a place outside the mall, just a few blocks away. We had a good time there. The food was delicious and she told me about her boyfriend, how he was the sweetest she ever met and that she was going out on Saturday with him.

“Talking about dates,” she looked at me “how are you feeling about yours on Saturday?”

“A little nervous, I’ve never been in a date before”

“I didn’t knew that. You just have to act as yourself, you’re really a really nice guy. She will fall in love with you”


We leaved the restaurant and took a taxi home. After we arrived I took my new underwear and makeup, and hid it under my bed with the other clothes. Vanessa wanted me to model it, but my parents could arrived any minute so we decided to do it another day.

At night I walked to her room and knocked.

“You can come in” She replied.

“Thanks for everything today, I really had a great time with you”

“Me too” She paused for a moment “I have another surprise for you”


“I’ve ordered something on the internet for you. Breast forms.”

“What are they?”

“They are fake boobs you can glue to your chest. They look very natural. You will look even better with them”

“I appreciate it so much, but the money you are pouring on this is starting to bother me a bit”

“I will someday tell you how I got the money, but for now, just enjoy it”


Before sleep a thought hit me. What if I erased the photo of me from her phone? She would not be able to blackmail me anymore. She was acting really nice but what if she decided to do something else. I planned to enter her room at night and get rid of the picture without her noticing. It was a perfect plan.

To be continued…

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