Secret Life of Oliver

Chapter 4 - The Proposition

For the next week, Oliver found himself a new routine. He would come home from school and change from his school trousers into the skirt and tights his sister gave him. He wouldn't do anything special when he dressed up, he would just go about his night like normal. He'd change back to go down for dinner then immediately swap afterwards. A few times he came close to being caught when his parents would knock on his door to speak with him about one thing or another. In these cases, he would usually throw something on to cover his legs, like a blanket, or dive under his duvets. In one instance, his Dad walked in to give him some laundry and, unable to do anything else, he basically pinned himself to his desk in order to hide.

When Alyssa came in from time to time, usually to ask about homework, he didn't hide. He felt like he was growing closer to her. Everyone so often, she would come in and ask his opinion about an outfit. Oliver knew she wasn't planning on wearing any of these outfits, she was just doing it to for Oliver, but he appreciated it.

Friday afternoon was no different. When Oliver and Alyssa got home from school, he rushed up to his room, got changed, and started doing his homework. He was half way through his chemistry homework when Alyssa came in.

"Hey, you got a sec?" She asked, sitting down on Oliver's bed.

"Uh, yeah." He swung around on his chair, pulling his skirt down a little. "What's up?"

"God, I still can't over how well that skirt suits you..." Alyssa said, looking him up and down. "Anyway, I have a proposition for you."

Oliver blushed a little. "What?"

"All week, you've been wearing this exact same outfit. And every time I see you in it, you look more and more happy. How do you feel about experimenting a little more?" She asked.

Oliver thought about it. He wanted too, but his parents were around too much. "I mean, I'd love to. But how is that a proposition?"

"Because I had an idea that I think would be really fun, would help you figure yourself out more, but is pretty risky." Alyssa said.

Oliver was a bit unsure. "How risky?"

"Well, that depends. There's a risk no matter what, but if we can pull it off, it should be really fun." Alyssa said.

This didn't make Oliver any less unsure. "What's your idea?"

"Okay so, tomorrow, Mum and Dad are away until Monday. They leave stupid o'clock in the morning tomorrow and won't be back until we get back from school on Monday." Alyssa started.

"Okay...?" Oliver said, curiously.

"I was thinking, as kind of a big experiment, what if we went on a little shopping trip? We can get you some clothes of your own that you can hide with the stuff I gave you. You can even try some stuff on, find your own style." Alyssa said.

Oliver thought about it. It would be fun and it would be really nice to have some of his own stuff, but he wasn't sure. "That'd be fun, but what if people from school see us? What if people think I'm a weird perv for looking at girls clothes?"

"That's where the risk comes in. If you're up for it, how do you feel about dressing up? You can borrow some of my casual clothes; skirts, dresses, jeans, whatever." Alyssa said.

"But then I'd just look like a guy pretending to be a girl looking at girls stuff. That just makes it worse." Oliver said, his stomach turning.

"Which is why I want to completely make you look like a girl. I have a wig from Halloween, a plain brown one that's really good quality. That and some makeup, I'm hoping I can make you look like any other girl." Alyssa said, smiling a little. "If you don't wanna do this, it's fine, but I had the idea and I thought I'd at least bring it up."

Oliver thought about it. This could be a really good opportunity for him. It could be fun and if he felt comfortable, maybe it would help him figure some stuff out. After a few minutes, he nodded slowly. "Okay. But if I end up looking hideous and gross, we don't go. If I say I want to go home, we go home. Deal?"

"Deal." Alyssa smiled. "If we are gonna do this, I can't call you Oliver. And people know that I call you Oli. So, you need a girls name."

Oliver had been thinking about names all week. In fact, balled up in his bin was a list of names had been thinking about yesterday. But he had decided on one that he liked. "Olivia."

Alyssa thought about it. "Olivia it is, Olive for short." She giggled. "One more thing, in case you decide to wear a dress or a skirt tomorrow, you might want to shave your legs and arm pits. Mum has an electric razor that I use for my legs and I know you have some grooming stuff so you could probably use some stuff in that for the rest of your body. Generally, you should try be hairless from the eyebrows down, but as long as the visible body hair isn't there and you should be good. Plus, the feeling of smooth legs, it's so good. So, so good."

"I will, thanks." Oliver said. "And uh, thanks for... everything."

Alyssa stood up and smiled. "You're welcome, Olivia." She walked away, leaving Oliver to think about tomorrow.