"What the hell are you doing!!?" I heard my sister scream. My eyes snapped open, my hand flying away from its grip around my cock. With our parents away and my sister out I'd thought I'd be alone for the evening and decided to have a wank. Now Michelle had come home unexpectedly and discovered me. It got worse. "Are those my knickers you're jerking off into?" She screamed again. I nodded shamefacedly. "You little shit. I'm telling on you."
"Please don't Michelle; I'll do anything you want." I pleaded.
She looked down at my lap where her panties were still wrapped around my now wilting dick and an evil smirk crossed her face. I moved my hand back to cover myself.
"It's too late for that you fucking pervert." She sneered. "Now stay there while I think." That scared me even more than being found. Michelle was three years older than me at twenty-one and she had tormented me for as long as I could remember. Now I had unwittingly given her free rein to torture me even more. The evil smirk came back. "Right, get to the bathroom." She ordered.
"The bathroom? Why?" I was puzzled.
"Just do it you tosser." She said and led me to the bathroom. There she made me sit on the lid of the toilet while she took my razor from the cabinet.
"What are you going to do with that?" I asked nervously.
"Give you a shave of course." She laughed. "All over."
First she shaved my face and then my chest before moving to my legs.
"Nearly done." She said, lathering up my pubic area. Despite the shame, the apprehension and the fact that it was my sister doing it, this action made my cock stiffen. "Fuck, you really are a pervert." Michelle said, running her hand along my hardening length. "You'd better not cum in my hand." She warned.
"No ma'am" I panted, trying to calm my now raging erection.
"Ma'am? I like the sound of that." Michelle giggled, taking the razor to my balls.
"Anything you say ma'am." I breathed.
"Good. Now keep still."
It didn't take too long for her to be washing the last of the soap from my now hairless dick.
"What next?" I asked. She looked up sternly. "Sorry. What next ma'am?"
"Well, you know I've always wanted a little sister to dress up..." She tailed off, the smirk on her face once more.
"NO!" I was appalled. "You can't mean what I think you mean Michelle."
"That's 'ma'am'. And I do mean it. You are going to be my little sister until mom and dad get back."
"But that's half a week!" I protested.
"Tough." She grinned. "Now get into my room, I'm going to make you look so pretty."
"But you're bigger than me, your clothes won't fit."
"Are you implying I'm fat?" She looked at me dangerously.
"No." I back-pedalled. "I meant you're taller than me."
"Anyway, you are not getting into my good clothes. I've still got some of my old things, and I know that they will fit you. Now stop stalling and get."
"Yes ma'am." I sighed, giving up on the argument and following my sister to her bedroom.
"Sit at the dresser while I find a few things. And keep your hands where I can see them." Michelle ordered.
"Yes ma'am." I sat down as she pulled a box from under her bed. It had 'for future fun' written on the side. Opening it, she pulled a pair of frilly black silk knickers out and tossed them to me.
"Put those on for starters. And try not to cum in them."
"Yes ma'am. May I say how I've always admired your choice of panties."
"I don't buy them for you to admire as you jacked off into them, pervert." She rummaged around in the box some more and found what she was looking for. At a distance it just looked like a normal bra. Michelle threw it to me and I saw on closer inspection that it was in fact padded. "That will give you a semblance of a bosom. And don't you dare ask if all my bra's are padded." She warned.
Meekly I pulled on the underwear, trying not to be aroused by the feel of the silky material around my clean-shaven bollocks and not succeeding completely.
"I think this, for your first outfit." Michelle announced as she pulled her old school uniform from the box. The sight of it made me more aroused than ever. Chelle noticed. "You weirdo; you're actually getting off on this."
I reddened and whispered; "Yes ma'am."
"This isn't supposed to be fun for you." She said sternly.
"No ma'am." I said, trying to push down my burgeoning erection.
"Just put the bloody clothes on." Michelle said, exasperated by my futile attempts to control my boner.
As I pulled on the outfit Michelle once more went into the box. This time she pulled out a pair of stockings and a pair of shoes. The stockings were black hold-ups with some strange patterning them. I got the distinct impression that she had bought them and then decided that she didn't like them after all. The shoes however were a different kettle of fish. I couldn't work them out. They were definitely the sort of shoes she would wear, but they looked new and unworn. I paused in my dressing after I had done up the school blouse and took a closer look. Chelle was changing her own clothes behind the wardrobe door and wasn't watching me. I picked up one of the shoes and turned it over in my hands. There was a complete lack of scuffing on the sole, which seemed to prove they were indeed unworn. Then I noticed the size: It was mine! A whole two sizes bigger than Michelle's. They was no way that she had bought and kept them by accident; they had always been intended for me. I looked up and saw Michelle looking at me.
"Well, Sherlock?" She smiled, raising her eyebrow quizzically.
"You've been planning this all along haven't you?" I accused.
"So?" She shrugged.
"Why?"
"The usual competition. I wanted to see how far you would go as a cross-dresser. I know you've been running your paws over my things for years now, so I thought I'd provide you with your own." She smiled again.
"Oh!" Was all I could say.
"Well?" Michelle prompted.
In reply I picked up one of the stockings and rolled it up my shaven leg, revelling in the feel of the nylon on my skin.
"Good girl." Chelle grinned. "When you've done dressing, I've got some make-up for you to try." Previously this statement would have appalled me, but now I was intrigued as to what my sister had planned for me. She had been right about my fetish for handling silky things, and actually wearing them was exciting me, so I was looking forward to seeing what she was going to do.
I finished dressing in the school uniform and pulled on the shoes, the heels were higher than I had thought. I looked up at Michelle expectantly.
"Try walking around a bit." She suggested. Obediently I stood up and tottered around a little, getting over the feeling of unsteadiness after the first few tentative steps. I looked down at my legs, noticing the pleasing feminine way they appeared with the heels on, and smiled to myself. Michelle noticed. "Yes, you don't look too bad at all." Then she frowned. "But this is supposed to be a punishment, remember? You're enjoying yourself way too much. I'll have to come up with something else."
"Maybe you could spank me?" I suggested cheekily.
