Chapter 3

It was midnight when I walked into Vanessa’s room. The light were off. I tried to open the door but it was locked. I stopped for a minute and remembered where my parents kept the spare keys of the house. In a drawer inside my father’s studio. I headed there, took the keys and went back to her room as silently as possible. I tried a few keys until one of them opened the door. It was very dark inside and I couldn’t see a thing. I took my phone out and turned on the flashlight. It luckily didn’t woke her up. I looked around for her phone but before I could find it I realized she was sleeping completely naked. It was summer and the nights were extremely hot but I never thought she would sleep like that.

I approached her and contemplated her body. She was sleeping facing down with her ass facing up. Her bare butt lit by my phone’s light looked perfectly rounded. Her legs were very slim. I wanted to touch them. Her body without any trace of hair. It was the body I wished I had.

After a minute or two of staring at her I focused on my task, finding and erasing the photo of me in a dress. I noticed her phone was laying under her right hand. I slid it off carefully and turned it on. It was blocked.

Fuck.

I tried a few passwords but didn’t work. Finally I used her birthday year, just one after mine. It unlocked. I searched the photo gallery and found my picture. I erased it. Placed the phone on the bed near her hand. And headed out. But before I left I took a photo of her lying on the bed naked. I thought maybe I could blackmail her with it. In my room before I went to sleep I took my phone out, looked to the photo of Vanessa, pulled my boxers down, took my penis between my hands and masturbated.

In the morning after, I acted normally, I put on my makeup, the best I could, dressed in a beautiful white dress and matching white thong and bra. The day went as usual. I did my house tasks, and played videogames. She went out with some friends. It wasn’t until the Saturday, just before I left for my date with Melissa that we talked.

“You should tell Melissa that you like wearing girl’s clothes, I’m sure she will understand, just like me” She said.

“I’m not sure. I don’t think that’s something you say in the first date”

“Well, that’s your choice. Anyway, what are you wearing to the date?” She asked.

“What I’m wearing right now” They were a pair of jeans and a blue T-shirt.

“I mean, what are you wearing underneath that? A bikini? A thong?”

“No, just some boxers”

“Really? I thought you liked wearing female underwear?”

“I do, but I think it could be a little uncomfortable. They might be visible when I crouch or something” I answered.

“I really think you should wear a pink pair of undies” she said imposingly “In fact, if you don’t, I will put your photo online”

“I would like you to try” I said challenging her.

She took out her phone and searched for the picture for three minutes.

“You will not find it. I erased it when you were asleep. And I took one of you, naked. So, if you don´t do what I say, I will post it online for everyone to see.” She didn´t looked scared or shocked or anything.

“This is what will happen,” she said “you will go change to some pink panties right now and I’ll think of a punishment for when you return.”

“Didn’t you hear me? I erased the photo, there´s nothing you can do, now the tables have turned. I have a photo to blackmail you”

“You are stupid if you think I didn’t made a copy of it. And if you ever publish the photo of me naked, you will look like a pervert, and I like a victim. I don´t think you want that. So do as I say and go change” she was almost shouting.

I was stupefied. I tried to make things better for me but just managed to make them worst.

“Go. Now” She ordered.

I went back to my room and changed to a pink thong as she ordered. Then went back to her room and showed it to her.

“You can go now. When you return I will have a punishment ready for you”

I left the house and went to Melissa’s. On the way there I kept thinking about what Vanessa would do. I was afraid. Melissa was already waiting for me outside her house. I approached her.

“Hello, how are you?” I asked her.

“Good, I’m happy we are going out together. It take you long enough to ask me. Or rather took your cousin long enough” She said laughing.

“Yeah, she helped me”

“You don’t look really happy. Is there something going on?”

“No, well yes. I had a fight with my cousin earlier”

“Oh, do you want to talk about it?” She asked very kindly.

“No, I would rather try to forget it, let’s get going”

We went to the cinema and watched a romantic movie. I don’t remember the name, but I found it pretty boring. In the middle of the movie she took my hand laid her head on my shoulder. After the movie ended we went to eat at the mall’s food court. She chose a salad and I a hamburger. We talked a lot. She was very funny and I couldn’t stop laughing. A few times I crouched to pick something up and I felt my thong showing up. I don’t think she saw it. It was getting late so I accompanied her to her house. She told me she had a great time and would love to see me again next week. But before I left, she got close to me and kissed me in the lips, said goodbye and got in the house. It was very sweet. I was happy and went back to my house smiling.

I went to my room and laid on the bed. Thinking about the kiss Melissa gave me earlier. But suddenly Vanessa walked in.

“Follow me, we have to talk about your punishment” I followed her silently. She closed the door of her room just after we entered. “I have given it some thought and came to a conclusion. First of all,” she extended her hand “give me you phone”

“You can’t take my phone. I need it”

“I will return it to you on Monday” I handed her my phone. “I was surprised to know you entered my room without my permission again. I didn’t even suspected. You saw me naked and took a photo of me. I felt violated. So I will punish you accordingly. Get naked” I knew I didn’t had a choice and removed all of my clothes. “Now lay on the bed, upside down”

“What are you going to do?” I asked a little scared.

“Shut up and do it” I laid on the bed completely naked, just as she was the night I broke into her room. She took something form under the bed. I couldn’t see what it was. Suddenly I felt something cold and wet between my butt.

“What is that? What are you doing?”

She didn’t answered. I felt the thing sliding inside my anus now. It was a bit painful. I almost screamed but I remembered my parents were home.

“It is called butt plug” She laughed. “Now stand and put your clothes on” I tried but it was very uncomfortable to move with that thing inside me. Finally I did. “You will use this for the rest of the day”

“But I can’t walk very well. And it is hurting me”

“Well, that’s the purpose. It is a punishment. Now, get out of my room. And don’t take it off”

I walked very slowly. After a while I got used to the butt plug, actually I started to enjoy the sensation of it being inside me. It made my dick hard and turned me on. I didn’t tell Vanessa her punishment wasn’t working the way she wanted.

At ten o’clock she entered my room with a smile. Ordered me to get naked again, but this time to take the butt plug out of me. I tried to act as if I was relieved.

“Why are you so happy?” I asked.

“I think you learned your lesson, or you will”

“I did,” I lied “and I want to apologize”

“Apology accepted” she said, paused for a few seconds and continued “Anyway, I didn’t have the time to ask you, how it went with Melissa?

“It went very well, we went to the movies and then we ate something. But most importantly, she gave me a kiss at the end of the day” I said with a big smile in my face.

“That’s great”

“Yeah, and she said she wants to go out again next week” I said excitedly “I just need my phone to agree on a date”

“You will get it on Monday”

The weekend went rather quickly, I was anxious to get my phone again to talk with Melissa. On Monday’s morning I woke up, dressed in a red bikini and matching bra, and a beautiful flowered dress. I went to the bathroom to put on some make up, but before I could finish the doorbell rang. Vanessa went to open the door. It was a package.

“Today I have two surprises for you” Vanessa said excitedly “One of them are these” She showed me the breast forms that had arrived a moment ago. She opened the box. They looked very real. “Try them on” I took the dress and bra off and she put the breast forms in my chest with some glue and they adhered very well to my skin. I put on the bra, now it was filled, and then the dress. “Now you look very close to a girl. You just need to let your hair grow and maybe exercise some to make your butt and hips look better” She said with a big smile in her face.

“Thank you. I like the way I look. The breast looks like mine.” I said happily. “What is the other surprise?”

“I won’t tell you, you will know in time.”

I continued the day as normal. Enjoying my new look. I washed the dishes and swept the floor. The breasts never moved out of their place and they bounced a little. They felt real. They felt mine. I went to my room and watched an action movie. In the middle of it the bell rang again.

“I will open the door.” Vanessa said “Don’t come out of your room.”

I kept watching the movie, it was not very good but I was entertained by it. I heard the door closing and Vanessa coming up the stairs.