Chapter 1
"What the hell are you doing?" My cousin said as she entered her bedroom. Her eyes wet and wide open in surprise of what she had in front of her. Me in her underwear.

I should go back a week to explain. I am 15 years old and live with my parents. The house is too big for just the three of us, with three bedrooms; one for my parents, one for me and one for any guests we might have, which are not many; an ample garden where my mother plants flowers like roses and daisies. Both of my parents worked so I was alone for the most time during the week. That time I spent mostly doing homework and playing videogames after school, mostly playing videogames.

Last weekend my cousin Vanessa, who was a year older than me, came to stay with us for the summer because her parents, my uncles from my mother’s side, were travelling to Europe for their 20th anniversary.
The doorbell rang and my mother opened the door.

"Hello, how are you doing? Come in, please" she said, greeting my uncles and cousin. My father and I took Vanessa’s baggage inside.

"Good, very excited for the trip" My aunt answered.

"Do you want anything? A glass of water, maybe?"

"No, thanks, I’m afraid we are in a hurry, we are a bit late to the airport so we don’t have time, plus a taxi is waiting"

"Oh, ok, don’t worry then, you can’t be late to your flight. We’ll talk when you arrive in London"

My uncles said goodbye to Vanessa, and then to us – Goodbye then, I call you when we get to the hotel – My mother walked them back to their cab, who was waiting outside.

"Why don’t you show your cousin her room?" My father told me " I’ll take her things upstairs in a minute"

She took the stairs and I followed behind her. She was wearing a short blue dress, because it was summer and it was too hot, and as she took each step of the stairs I could see everything that was under it. I tried not to look, but still, I did. She was wearing a matching blue thong under her dress, her toned legs and round butt looked amazing. She was almost perfect. I, on the other hand, was a skinny boy, with little to no muscles and, something that embarrassed me a lot, a little penis. I hate genetics. How could my cousin look so good and I so bad?
We walked to the guest room on the second floor, just beside my own bedroom. I opened the door. It was the same size as mine, there was a bed with light pink sheets, a small bureau with a lamp on it and a desk just in front of the window.

"We prepared the room for you, " I said " last week it was a mess with boxes filled with useless stuff everywhere"

"That’s really nice "

" You can put your clothes there" I said pointing at the closet "We hope you are comfortable here"

"I will, thanks, just need to get my things in place" my father entered as she said this.

"Here are your things, if you need help with anything, just ask. We will leave you to settle" my father said and she nodded. He stepped out of her room and I followed.
But before I could leave Vanessa said "Mark, can you help me organize my stuff "

"Sure, what do you want me to do?" I asked.

She pointed to her cases in the bed "Just pass me everything and I’ll organize it in the closet and drawers"

I opened the first bag. There were some jeans, shorts, skirts and shirts. I passed some of them to her." How do you feel about your parents leaving you here for two months?" I asked while handing her another bunch of her clothes.

"A little jealous, but happy for them, it’s their anniversary and they should be together, but I wish I could go" I passed her another bunch "Anyway, I’m sure I’ll be fine, going out with my friends, with my boyfriend"

"I didn’t know you had a boyfriend" I opened the second case, where there were dresses and shoes.

"Well, it’s kind of recent. His name is Daniel, he’s nice and he makes me laugh all the time" I gave her the dresses.

"That’s good, you need someone that makes you smile" I handed her the shoes. And then there was her underwear. It was very colorful, and I don’t know why by looking and touching them I started to get hard. I tried to hide it. I don’t think she noticed.

"I just hope it doesn’t end like the last one" I gave her the bras and panties. She looked a little embarrassed.

"How?"

"My last boyfriend cheated on me with one of her friends"

"That sucks" I said, and started to open the last bag.

"You can leave that one" she said "You can leave now, it was nice talking to you. Hope we can do it more often"

"Sure, anytime" I walked out of her room and went into mine.

The first week went very well. We talked a few times, she told me about the date she had with his boyfriend that week, about her friends, and I told her about my friend that was out of town and a girl I met during school but was afraid to ask her out.

"Her name is Melissa" I told her, a little embarrassed "we had a few classes together. She is really cute, we talked a few times and she is very funny"

"And why didn’t you ask her out?"

"I don’t know, I was afraid she’d say no" I answered "but I still chat with her sometimes"

"I think you should ask her to go on a date with you?"

"I don’t know"

"Come on! I’ll help you!"

"Ok, but next week"

"Ok"

The next Monday arrived and she went out with her boyfriend to the movies. I was left alone in the house, as usual. During the week I kept thinking about what I felt when I took her underwear. How soft it was and how would it feel on my skin. I played videogames for a while but that thought kept coming. So I decided to enter into her room as she was going to be out with her boyfriend. It wasn’t locked. I opened the door, headed to the closet, and opened the drawer where her underwear was, I took out a pair and felt it on my hands. It felt so good, I started to get hard again. I put the thong and bra I took, they were both pink, on the bed. I looked at her dresses and chose a small red one and put it on the bed too. I decided to take a shower and shave before trying them on.

I got to the bathroom, took my clothes off, and looked at my small penis, just 3.5 inches when hard, I measured it a month back. I found a hair remover cream in her things too, so I used it in all of my body, except the arms, so my parents couldn’t know I used it. I got into the shower and as the water hit my body, the hair started to fall. At the end I was so smooth. I took a towel and dry myself. I went into her room again, this time to get in the clothes.

I put on the thong first. My penis was comfortable in it, even when hard. Then I put some stockings, very slowly because I knew they could break easily, and a garter belt. I only needed the bra, I brought out a pair of socks that could fill it, and it was a little hard to put it on, but at the end I managed. I looked at myself in the mirror that was next to the closet before wearing the dress. I looked funny, a little like a girl but still manly without the hips, butt or breasts. I was going to put the dress on but the door opened.

"What the hell are you doing?"
My cousin arrived early, I couldn’t believe it, and I was paralyzed, there in her room, in her clothes. It was the end, she would tell my parents. The fear filled my mind.

She closed the door. Not saying anything for a few seconds that seemed like minutes to me. "You look nice in those, but you could’ve asked, you know?"

I was still shocked and embarrassed and could only mumble "I… just…I"
She stopped me "It’s ok, do you like them?" I still couldn’t talk, so I nodded. "You can keep them, let’s just finish what you started, ok?" She opened a drawer "I see you used my shaving cream" She took out a small box. "Let me put you some light makeup"
I sit on the bed, silent. And she put something on my face, I didn’t know what it was. She put some lipstick on my mouth and some eye shadow around my eyes. "You look better. Now put on the dress and let’s have a look at you"
I put on the dress and stood in front of the mirror. I looked at me, with the makeup and the dress I did seemed more like a girl. Then I saw a flash.

To be continued…

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?”

“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?”

“Great”

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”

“Thanks”

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”

“What?”

“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”

“Ok”

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…

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.