"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.
"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.
"Maybe I will, but it sounds like you'd get off on that as well. I'll have to think about it while I do your make-up. Sit down so I can start."
I sat down at the dresser and let Michelle prettify me. It didn't take long, but there was a problem.
"Chelle, my hair is too short to make this work." I said as she finished with my face.
"Thought of that." She said, pulling a blonde wig from one of the dresser drawers. "Sit still while I fix this on." Dutifully I did so. The final result was stunning. I stared at what she had wrought in the mirror. It was strange, looking into the mirror and seeing a reasonably attractive girl peering back.
"WOW!" I said.
"You do look cute." Chelle laughed. I was unaccountably pleased by her praise. As brother and sister we had squabbled pretty much all my life, so any compliment, even one that said I made a good-looking girl, was a novelty. I beamed.
"What next then sis?" I asked.
"I think," she said thoughtfully, "that we should show you off, go outside." My smile vanished. "What's the matter?" She asked.
"You really think I can pass for a girl?" I replied.
"Only one way to find out 'sis'." She laughed.
"All right then, lets see." I said, squaring my shoulders. "Where are we going?"
"Just a walk down to the local shop." Michelle smiled. "Just remember to swing your hips when you walk."
"Yes ma'am." I gave her a worried grin.
The shop was a fifteen-minute walk away. As we stepped out into the street I was terrified that I would be recognised so I concentrated on perfecting my walking, but after drawing a couple of admiring glances from guys I had been to school with without them realising it was me I began to feel confidant that the disguise was holding. I began swinging my ass even more exaggeratedly.
"Ease up on the wiggle sis," Michelle whispered, "otherwise you may well end up with a date." A sly grin crossed her face. "Unless that's what you're aiming for?"
Suddenly I panicked.
"What? No! I'm not gay." I exclaimed.
"Ah! An idea that you don't like." Chelle grinned. I caught the hint of triumph in her voice and felt a tinge of worry.
We reached the shop and Michelle made me stay outside, saying that she wanted to get some vodka and being accompanied by a schoolgirl with no I.D. would complicate matters. As I waited I got a whistle from a passing car and didn't know whether to be pleased or embarrassed. Michelle came out of the shop with a carrier bag in one hand and slipped the other through mine. She looked suspiciously pleased with herself. I gave her a quizzical look.
"I've had an idea about what to do next." I grimaced. "Don't be like that. You've enjoyed yourself so far. Too much in fact." She smirked.
"I suppose." I sighed, letting her lead me home. We were nearly there before I realised I'd been wiggling my ass as we walked without thinking about it. It made me wonder about myself: Was I some sort of hybrid boy\girl, or was I just the pervert my sister thought I was? I got the feeling from Chelle that I was about to find out.
In the kitchen Michelle took her purchases from the carrier and stood them on the table in front of me one at a time. First was the vodka, then a bottle of cola, followed by a small chocolate bar, and finally, a bottle of baby oil.
"Want some?" Chelle asked, waving the vodka bottle at me and munching on the chocolate. I shook my head, unable to tear my eyes from the baby oil. I knew what it could be used for and I suspected that I knew what my sister intended to do with it. "Sure?" She asked again, pouring herself a generous measure of vodka and adding not much cola.
"No thanks." I said dryly, still apprehensively staring at the baby oil. Shrugging, she downed the drink in one and then picked up the three bottles and the glass.
"Come on then, lets get on with it." She said and started upstairs to her room. Gulping, I followed.
I sat down at the dresser once more as Michelle stooped to look for something in her bedside cabinet.
"Found it!" She said happily, holding up a large black vibrator.
"Shit! I knew it." I swore.
"You sure? Maybe I'm going to play with myself and make you watch." She grinned.
"Maybe, but you're not." I said flatly, worried and excited at the same time.
"No, I'm not." The grin had now become a nasty smirk. She poured herself another drink.
"What do you want me to do now?" I asked resignedly.
"Kneel down next to the bed, flip up your skirt and pull your knickers down from your butt hole." She ordered.
Sighing, I did what I was told, Michelle taking another drink before dribbling baby oil over the vibrator. She moved around behind me and suddenly I felt the cold liquid squirted around my ass hole, causing me to jump.
"Calm down, you know you'll probably like it." Chelle said soothingly.
"That's what's worrying me." I said.
"Don't, just relax. I'm going to stick my finger in first." She said as I felt the aforementioned finger inserted into my ass. It was worryingly arousing and I felt my cock stiffening again. Oh shit, I was a pervert. I let out a moan as Michelle added a second finger into my ass.
"Chelle, is this incest?" I asked as she moved them in and out of my butt.
"Not yet, little sis, not yet." She replied. That was worrying too. What else did she have in mind? "Ready?" She asked. I peeked over my shoulder. She held the vibrator up. Scared and curious, I nodded my assent. Michelle took her fingers from my ass and gently replaced them with the plastic phallus. I tensed. She slapped my right buttock. I forced myself to relax and it slid in. It was an incredible feeling, and one I was more ashamed of than anything else so far. Chelle worked the vibrator in and out of my back passage slowly and I could feel my now-hard dick starting to leak pre-cum. I moaned softly as she thrust the toy deeper and deeper.
"Chelle," I panted, "you're going to make me cum."
"Really?" She sounded surprised. "You take over with the vibe so I can see." I looked over my shoulder to see her crouch down. A little reluctantly I reached behind me and took the vibrator from her. It was awkward and I couldn't keep the same rhythm as she had. I felt rather than saw her hand pulling my panties further down, releasing my throbbing cock. "You're leaking onto the clothes." She said from beneath my stomach. "Your naughty prick needs something over it."
"Like a condom?" I suggested.
"Not a bad idea, but I was thinking of something else."
And then I felt my sister's lips encircling my engorged penis.
"Chelle! What are you doing?" I asked incredulously.
"What do you think?" She replied, momentarily releasing my cock from her mouth.
"But you shouldn't."
She ignored me and carried on massaging my member with her tongue and lips. I knew I wasn't supposed to be liking her oral ministrations, she was my sister after all, but my dick evidently had it's own ideas. She stopped abruptly and sat up from beneath me.
"This is awkward and uncomfortable. Lie on your back with your legs up." She told me.
"Chelle." I protested.
"Just do it." She sighed.
A little reluctantly I turned over onto the bed and held my legs out of the way.
"Good. Now I can get at your prick properly and work the vibrator at the same time." She said and then engulfed me again as well as thrusting the vibrator in and out of my ass. She also turned it on. The added sensation pushed me close to a climax but I managed to hold back. I couldn't cum in my sister's mouth; that would be so wrong. It seemed that Michelle had other ideas though. She bobbed her head back and forth along my shaft, quickening her pace at the same time as speeding up the thrusts of the vibe. I was panting with the effort of NOT cumming, but it was to no avail.
"I'm gonna cum Chelle!" I cried out as I felt myself begin to twitch, but she didn't let up. I could hold off no longer and shot off my load into her mouth. "Shit! I'm sorry sis." I panted, almost in tears.
"Why?" She asked sitting back on her haunches. "You liked it didn't you?"
"That's not the point is it? You're my sister."
"So?" She said, unconcernedly wiping excess cum from her lips.
"Siblings aren't supposed to do things like that." I explained. I was starting to get annoyed with her attitude.
"My choice: Your punishment." She grinned. And then I saw an idea flash across her face. "Maybe I should be punished in return then." She suggested.
"What?" Her sudden change of tack confused me. What was she on about now? Michelle stood up and slipped off her knickers, hiking her dress up over her hips to reveal a shaven cunt. I stared at it uncomprehendingly until I suddenly grasped her intention. I gasped. "Chelle, you want me to..?"
"Fuck me? That's exactly what I want."
"But I can't." I wailed.
"Can't get it stiff for a woman then?" She sneered.
I had been annoyed before, but her words sparked anger in me now. I'll show her I resolved, all fears about this taboo coupling burning away. I jumped to my feet, grabbed Michelle and threw her onto the bed. Although surprised, she smiled up at me and spread her legs.
"I'll show you what I can do, you wanton bitch." I yelled, tearing off my skirt and then pressing my still-rigid cock against the entrance to her astonishingly wet pussy, stopping before I actually penetrated her.
"Go on, stick it in." Chelle urged. I plunged in as deep as I could. She grimaced and tears sprang to her eyes. Confused again, I stopped; my anger dissipated as quickly as it had arisen. I looked down at Michelle.
"What's wrong? I thought you wanted me to fuck you?" I asked softly.
"I did, I still do. It's just..." She tailed off.
My gaze shifted from her face down to her exposed cunt now plugged by my dick. And saw traces of blood. I looked back at her face in shock.
"You were... a virgin? But how? The blowjob? The vibrator?" I was monumentally confused.
"The vibrator was for my ass. I never found a guy I wanted to let fuck me, so I sucked them off." She explained, her tears drying and a smile coming back to her face.
"But why me?"
"Because I love you."
"You've had a funny way of showing it through the years Chelle. And why the dressing up?"
"I thought the best way to get you to screw me was to get you horny and angry. I was trying for inebriated as well." She gave me the warmest smile ever. "Now I want you to fuck me. Fuck me like your lover." She clenched her pussy around my cock to emphasise her words. Still a bit shocked, I hesitated for a moment until I realised that I loved her too. All the rummaging through her clothes, the wanking off into her panties, had been because I couldn't have her.
"Okay sis. Because it's you." I finally replied and began to slowly screw her. Michelle wrapped her long legs around me, pulling me closer in.
"Damn sis, you fuck good." Chelle laughed.
"You're not too shabby yourself." I panted. She couldn't reply as she was cumming, her pussy grabbing my cock as she climaxed. I had to stop until she relaxed again.
"Carry on bad girl." She breathed as she came down from her sexual high. I resumed my pumping but then had an idea of my own.
"Chelle, I don't want to cum in your pussy, just in case. So how about I fuck you in the ass? You said you got yourself off that way."
"I'm protected anyway." She smiled. "But we'll try it your way, lover girl."
I moved back to let her flip over onto her hands and knees. She looked over her shoulder provocatively and waggled her bottom at me.
"You seem to be enjoying your 'punishment' as much as I did." I said wryly.
"Probably for the same reasons." She laughed. "Now get on with it, slacker."
"Yes ma'am." I laughed back.
I eased up behind her, positioning my cock head so that it rested against the starfish of her ass hole. Impatiently Michelle pushed back against me and I slipped partway into her butt.
"Hmmm, real meat feels so much better than imitation." She cooed.
"And your ass feels as sweet as your cunt." I replied, pushing deeper in.
"Hey, where's my vibrator gone?" Chelle asked.
"Here in my hand. And it's going back into my butt." I told her before sinking the dildo up my bum and switching it on.
"You really are a perv." Chelle giggled.
"Hark who's talking." I smiled back.
"Oh shut up and take my ass."
"Thrusting in now ma'am."
I pulled back and then pushed deep into my sister's butt. She gave a satisfied grunt and then looked over her shoulder at me.
"You know what feels weird?" She panted as I rocked her back and forth along my cock.
"Apart from having your brother fuck you in the ass?"
"I give up."
"The feel of your stockings rubbing against the backs of my legs."