Learning to Change - Part 1

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.


"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"


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…

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This story is 1629 words long.