“What the hell are you doing!!?” I heard my s****r scream. My eyes snapped open, my hand flying away from its grip around my cock. With our parents away and my s****r 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 s****r 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 s****r 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 s****r 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 s****r 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 bl**dy 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 s****r 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 b*****r and s****r 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 s*s?” 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 ‘s*s’.” 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 s*s,” 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 boygirl, or was I just the pervert my s****r 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 s****r 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 i****t?” I asked as she moved them in and out of my butt.
“Not yet, little s*s, 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 f***ed 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 s****r’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 s****r 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 s****r’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 s*s.” 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 s****r.”
“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 bl**d. 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 s*s. 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 s*s, 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 s****r’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 b*****r fuck you in the ass?”
“I give up.”
“The feel of your stockings rubbing against the backs of my legs.”
“Well I quite like it.” I grinned.
“Oh shit! I’m cumming again.” Michelle cried out suddenly.
“Hold on, I’m nearly there too.” I gasped.
It only took a few more strokes for Chelle to climax, clamping around my dick. That did it for me too; I fired my wad into her anal passage. The two of us collapsed together in a heap on the bed; my cock still in Chelle’s ass, the vibrator in mine.
“That was everything I imagined.” Michelle whispered.
“Never having imagined fucking you, I can’t compare,” I whispered back, “but it was some kind of wonderful, s*s.”
“Your dick is still hard.”
“Must be because it’s up your butt,” I paused, “or it’s the vibrator up mine. I’ll take them both out.”
As I did so, Michelle changed her position to face me. We wrapped our arms around each other.
“What’s going to happen next?” She asked.
“You’re the one with the ideas Chelle.” I joked.
“No. I don’t mean for the rest of the week. I mean after that.”
“I honestly don’t know. Let’s not think about it until we have to. Let’s enjoy these few days.”
“I like how you think.” She said, kissing me. “How tired are you?”
“Not very. Why?” I said carefully.
“Cos I’m still randy.” She actually blushed.
“Good. So am I.”
“You know, you still look awfully cute in what’s left of your school uniform.” She giggled.
“You look cute in whatever clothes you’re wearing.” I said, kissing her on the nose.
“What about without clothes?” She teased.
“Well I can’t really say can I?”
With a grin Chelle threw her remaining attire to the floor and then lay back, now totally nude. I ran my eyes over her nakedness.
“How about now?” She asked coyly.
“If pressed, I think you look even cuter like this.”
“Smoothie.” She laughed.
I couldn’t take my eyes off her. I was mesmerised by the sight of her naked bosom. I had never really thought about them before. I was entranced by their smooth milky roundness, topped off by perky, pert nipples. Michelle spotted my staring.
“Like what you see?” She asked, her hands cupped each breast. “I told you I didn’t need a padded bra.”
“Michelle, they are lovely, beautiful. Why have I not seen that before?”
“Probably because you were obsessed with my knickers.” She smirked.
“Could be. Can I touch them?”
“You’ve just had your dick up my arse and you’re ASKING about groping my tits?” She laughed. “Feel free to fondle.”
I reached out tentatively, brushing the magnificent orbs almost reverentially. Michelle giggled.
“Go on, they’re not that fragile you know.”
Emboldened, I cupped both breasts, gently massaging them, teasing the now erect nipples with my thumbs.
“That feels nice.” Chelle breathed, her eyes sparkling. I leant forward and licked her right tit, leaving a wet trail across her skin. “Oh yes.” She sighed, closing her bright eyes. I began to suckle on the teat, teasing the left one with my thumb and forefinger. “Your new hair is tickling me.” Michelle said suddenly.
“It is getting in the way a bit.” I responded, moving to pull the wig off.
“No. Leave it. I like the way it makes you look.”
“Yes ma’am.” I mumbled, my mouth again full of breast. The feeling of Chelle’s tits under my mouth and hands was nothing short of awesome; I found I couldn’t leave them alone. But Michelle was getting impatient.
“You going to be playing with my bosom all night?” She asked pointedly.
“I was considering it.” I grinned, looking up.
“There’s somewhere else you could be using that surprisingly talented tongue you know.”
“There is, isn’t there? Sorry.”
“Apology accepted. Now I want to feel some tongue action between my legs.”
“Certainly ma’am.” I smiled and then slowly slid down her body, kissing her stomach as I went. I reached her naked cunt. It was wetter than ever. I lapped at the liquid that was leaking out. “You taste great Chelle.” I told her.
“You did too.” She told me as my tongue slipped between her pussy lips, causing a gasp. I smiled to myself and ran my tongue along her slit to her hooded love button. I sucked on the sweet nub for a moment before pushing my tongue deep between the folds of flesh that were the entrance to her cunt. Michelle let out a long low moan of pleasure. I continued to plunge my tongue in and out, switching up to her clit every so often. Soon Chelle’s breathing was becoming ragged. And then:
“Oh god! I’m cumming!! Just your tongue and I’m cummmmiinnnnng!!!” She came, flooding my mouth with her sweet nectar; So much of it that I nearly choked. She subsided and looked down at my face still between her thighs. “Your dick. Stick your dick in me again.” She begged. I became aware of how big a boner I was now sporting as I shuffled up to her and sank it into her soft welcoming snatch. Michelle gave a contented sigh and thrust her hips up to meet mine, wrapping her legs around me and crossing her ankles behind my back. I rocked gently back and forth, slowly fucking my s****r. To be honest by now I was tiring a little and told Chelle so.
“Really? Okay then.” She said, rolling us over so that she was on top and then riding my cock. Looking up, I was mesmerised by the jiggling of her tits as she bounced on my shaft. She leant forward and put her hands on my chest to brace herself. I raised my hands to her perfectly formed breasts, marvelling at how they seemed to fit so neatly into my palms. Michelle was moving faster now, pushing towards another orgasm. I felt my balls tightening and knew I was close as well. Chelle stiffened and stopped her riding of me as she climaxed. I flipped us back over, pulling out of her cunt as I did. I jerked my dick for a few strokes until I came as well, spurting my milky jizz over her heaving stomach.
“Why?” Chelle panted, looking up after she felt the hot spunk on her skin.
“Cos that’s what I was doing at the start of this escapade.” I told her. “Sort of rounds it off nicely.”
“Replacing my panties with me? You are weird. I wanted that cum in my pussy.” She pouted.
“Tomorrow, I promise.” I smirked. “Now we need sl**p, it’s late and we’re both tired.” I crawled up alongside my s****r. We curled up in one another’s arms and drifted off to sl**p.
I woke up late the next morning, glad that I booked a weeks leave from work already. I left Chelle to sl**p on. She too was using some accrued vacation time. It meant we had at least another two days together before we had to think about the future. I took a quick shower and then went downstairs to the kitchen wearing only a towel. I made myself coffee and sat down to wait for my s****r to wake. Half an hour passed before I heard the water running in the shower and it was another thirty minutes before Michelle appeared in the kitchen in her flimsy and nearly transparent sheer dressing gown.
“Morning sl**py head.” I said cheerfully, moving toward the kettle again. “Want breakfast?”
She shook her head, but carefully.
“How much did I have to drink?” She asked.
“About a third of a bottle of vodka.” I smiled.
“Why did you let me drink so much?” She muttered. “You know I can’t take too much alcohol.”
“Hey, you were in charge, remember?” I grinned.
“Well maybe you should be today.” She groaned. “I feel like shit and I’d probably end up doing something we’d both regret.”
“So you don’t regret what we did? I know I don’t.”
“Just that we didn’t do it sooner.” She gave a weak smile.
“Well, if I’m in charge,” Chelle nodded, “then I think that you should get some more sl**p while I sort a few things out. Use my bed, I’ll wash the sheets from yours.”
“Okay,” She gave another wane smile, “and thank you.” She turned and went back upstairs, leaving me to make plans. My mind was ablaze with possibilities, most of which I discarded as impractical. I couldn’t dress Chelle as a guy; that would be copying her. So what then? I continued to muse as I set about the chores for the day.
Michelle resurfaced mid-afternoon looking much perkier.
“Better?” I asked.
“Much.” She smiled. “Come on then, you’ve had a good four hours, what have you go planned for me?”
“I’m glad you asked.” I gushed. “After thinking about some of the clothes I’ve seen you wearing over the years I think I can dress you as…” I paused for effect, “a lap dancer.” I beamed.
Michelle gave me a cold stare.
“Are you suggesting my clothes are slutty?” She frowned.
“What? No! I just meant that I could take various bits and pieces from your outfits and come up with something a dancer might wear. My first choices would have been a nurse or a policewoman, but both of those would need something like the proper uniforms.” I gabbled worriedly.
Chelle’s face broke into a smile.
“Only teasing.” She laughed. “It sounds…interesting. Sure it will work?”
“If I can have the run of your wardrobe.”
“Any excuse to fondle my stuff.” She laughed again. “In any case, you’re going to get girlied up again tomorrow, so you should make the most of today.”
“I intend to Chelle, I really do.”
“Come on then, show me what clothing I’ve got that you think should be on a stripper.”
We entered Michelle’s bedroom and she flopped down onto the freshly made bed, a questioning look on her face.
“Okay then mastermind, what first?”
“Erm, do you still have your fishnets?” I asked, knowing that wear and tear on hosiery was high.
“Tights or stockings?” Chelle responded.
“Stockings, hold-ups for preference.”
Chelle nodded and went to one of her drawers, pulling out a rolled up pair of what I’d asked for.
“Next?” She asked, sitting back down.
“That silvery set of bra and panties.” I said, slightly embarrassed about letting on I knew about them.
“Get them out then; you obviously know where they are.” Chelle laughed at my discomfort, pulling on the stockings as she did. Still blushing I found out the underwear and passed it over. She slipped those on too. “That it?” She asked.
“It needs something else.” I suggested. “Can I take a look through your wardrobe?”
“Like you never have before?” She laughed. “Go on then.”
I flipped through the clothes hanging up in her closet, pulling out one or two for a closer look, before shaking my head and putting them back. I turned around to Chelle.
“Is there anything else?” I asked. “You’ve got some nice short skirts, but none of them seem…well, short enough.”
“Try the suitcase on top.” Michelle grinned. “I can’t believe you never found my ‘bad girl’ stash.”
“I never knew you were keeping stuff especially for me either.” I retorted over my shoulder as I got the suitcase down. I put it on the bed next to Chelle and sprung the catches, opening it. I gasped. Inside was a veritable cornucopia of risqué clothing and similar items. A latex top, a sheer nylon body stocking, some sort of leather harness, a baby doll nightie, one or two exotic toys, and what I was looking for: A pleated tartan skirt little wider than a belt. Michelle picked it out of the case and wrapped it around her waist. “How come I’ve never seen you wearing any of this stuff s*s?” I said.
“That’s because mom and dad would have had a cow if I put them on at home. So we used to get changed in the loo’s up town.”
“So you actually wore this stuff out?” I was incredulous; the skirt barely covered her ass.
“Yep!” She grinned, enjoying my surprise. “Hey, how about this to finish off the outfit?” She asked, fishing out what appeared to be a ring of Lycra that may or may not cover her breasts.
“Try it.” I said. “But I think it’ll look better without the bra.”
She took the bra off and replaced it with the tiny tube top. Suddenly I saw the final part of the outfit nestling in the corner of the suitcase: A pair of really tall and glittery stilettos. Michelle followed my gaze and then with a sigh picked the shoes up and strapped them on. She stood a little uncertainly, as if not as used to the shoes as she pretended. Now she was taller than me.
“That looks great Chelle. It just needs some over-the-top make-up to finish it off. I’ll leave that to you while I go and get changed.”
“What makes you think I know about overdoing my make-up?”
“Chelle, I’ve seen what you normally put on when you go out. If you go a bit further than that, it’ll be right.” I laughed, making to leave.
“Smart arse!” She called out as I shut the door behind me.
I’d dressed up a bit; shirt and tie, jacket and trousers; and was waiting for Michelle in the lounge downstairs. She announced her arrival by wrapping her leg around the door and then peering around the frame. She had obviously taken on my idea completely. Her hair and make-up could have been taken straight from the picture I had in my head.
“Did someone here order a lap dance?” She whispered huskily.
“Yes.” I managed to squeak, using the remote to turn on the stereo. It was a slow bluesy rock track. Michelle began to move to the music. I had no idea she was capable of such sensuous movement. She flowed across the floor, dancing toward me. Once she got to me she started to tease me; pushing her bosom towards my face before turning around and waggling her ass mere inches from my crotch. Fascinated by her lithe movements I reached out and put my hands on her hips.
“No touching: House rules.” Chelle said over her shoulder. Reluctantly I took the hands away again as Michelle continued her dance, writhing to the music like a natural dancer. She flaunted and teased, her body almost but not quite brushing mine.
“Hells teeth Chelle, you’re fucking good as this.” I breathed, itching to reach out and run my hands over her sinuously swaying body.
By the time the song ended Michelle was perspiring freely. She sat down on my lap heavily.
“That was fun, but tiring.” She sighed. “No need to ask if you enjoyed it.” She said, grinding her ass against the massive boner her dancing had given me.
I groaned in frustration.
“God Chelle, you missed your calling. You would have been a great stripper.”
“Why thank you.” She giggled and wriggled her butt again.
“Please don’t do that, you’ll make me cum.” I gasped desperately.
“Not until I’ve got to play with it you don’t” She laughed and slipped off my lap and onto her knees in front of me.
“I thought there was no touching?” I asked as she unzipped me.
“Only while I was dancing.” She answered, pulling out my cock that was slick with pre-cum already. Michelle dropped her mouth around my throbbing shaft, greedily licking at its wetness. I let out a moan as once more her soft lips went all the way down to the root of my member. It felt so good that I knew I wouldn’t be long before I blew my load. Within a minute I was hosing spunk over Chelle’s beautifully painted face.
“That was quick.” She said, wiping the gloop from her eyes.
“Sorry.” I panted.
“No sweat. But you’d better last longer when you fuck me.” She grinned.
“No guarantees s*s, you are one sexy bitch.” I grinned back. I leant forward and kissed her, tasting my own spunk on her lips. Michelle lay down, pulling me with her. I kissed down her face and neck towards the lycra-clad mounds of her tits. I licked at the now-hard nipples through the material. I eased the tight Lycra from her heaving breasts, licking at her pert buds and eliciting a moan. I replaced my tongue with my hands and moved my head lower down to her belly button, using my tongue to tease it while continuing to massage her tits. Chelle giggled and squirmed under my tender assault before gently pushing my head ever lower, towards her pelvis. I took the hint and slid down between her legs. I flipped up the narrow tartan cloth masquerading as a skirt to reveal the growing damp patch on the silvery panties beneath. Michelle let out another moan so I glanced up: she was kneading her tits while toying with her nipples. I felt a sudden desire to get at her snatch quickly, so I jerked her knickers to one side and plunged my tongue into her wet pussy. Chelle gasped at the unexpected intrusion but responded by pushing her hips up into my face and crossing her ankles behind my head.
“Come on lover, make me cum with your mouth again.” She breathed.
I went to work with a will, slipping my tongue into her cunt as deep as it would go and coincidentally rubbing my nose on her clit. In the spirit of inquiry, just to see what would happen, I stuck a finger into Michelle’s ass hole. She began to thrash about in some sort of pleasure induced sensory overload and came hugely moments later; tensing up and then relaxing with a satisfied sigh.
“You do have a talented tongue little b*****r.” She managed to wheeze out.
“And you have a very tasty pussy, dear s****r.” I grinned back, licking my lips.
Michelle pushed herself up onto her elbows, looking me straight in the eye.
“What do you have planned for me next?” She asked, a devilish glint in her eye.
“I…I…dunno.” I stammered. “I never expected you to go along with the ‘dancer’ idea even.”
“I told you you were in charge today.”
“I know. I just never really believed you I suppose.” I shrugged helplessly.
“So, no ideas then?” Chelle frowned.
Even as she asked the memory of an old fantasy of mine resurfaced.
“Well,” I said slowly, “how about a knee-trembler? Outside. Against the kitchen wall.” I was still expecting Michelle to balk at this, even though our garden was totally secluded and not overlooked by any of our neighbours. Instead she sat up and smirked.
“Okay.” She said.
A little stunned by her acceptance, I helped her to her feet and led her out of the back door. She shivered slightly in the cool evening air.
“Let’s get you warmed up.” I said, leaning her back against the outside kitchen wall and plonking a kiss on her lips. Only this time I added something else; I pushed my tongue between her teeth. After a minor pause to overcome her surprise Chelle responded in kind, our tongues dancing around each other. At the same time my hands went once more to her lovely tits, softly squeezing and rubbing them. She in return left one hand holding the back of my head while the other dropped to my crotch and began to fondle my still exposed balls and giving me a raging hard-on in seconds.
“Uhhh.” I grunted. “Sorry Chelle, I can’t wait.” I said as I pushed her panties aside again and thrust my cock into her willing cunt. She gave a satisfied grunt of her own and wrapped her still fishnet-clad legs around my waist, held between the wall and me.
“That feels so good,” Michelle cooed, “and so deep.”
I was concentrating on keeping us both upright while giving Chelle the rigorous shafting she obviously wanted. I could feel her pussy muscles grabbing at my dick and the hot rasp of her breathing as she edged closer to yet another climax. I wasn’t that far behind her. With a cry of joy Chelle came, grasping me tightly with her legs. It took only a few more thrusts before I followed suit, my knees actually trembling as I shot my hot spunk into her. We leant against the wall catching our breath.
“Great idea b*o.” Michelle panted. “The thought of being seen gave it something extra.”
“It’s hard on the legs though.” I agreed, gasping.
“Wanna go again?” She asked, licking at my ear.
“You are insatiable Michelle.” I said back. “Not to mention incredible.”
“I can’t help it if you haven’t fucked me in the ass yet today.”
“Slut.” I grinned.
“Whore.” She grinned back. “Now let me suck you hard again.” Even as she was saying that Chelle had swapped positions and was now kneeling in front of me with her talented lips around my still semi-hard meat stick.
“Oh you greedy mare.” I said as she enveloped my cock completely. She sucked deliberately noisily for a few moments before leaning back.
“Our combined juices taste great.” She smiled.
“Better than chocolate?” I asked cheekily.
“Too close to call.” She laughed in reply. Meanwhile my cock had gotten stiff again surprisingly quickly. “There we are; ready for action.” Michelle smirked triumphantly. “But first…” She swallowed my whole dick in one go before standing up again, leaving my hardness covered in her drool. Evidently eager to be buggered, Michelle braced herself against the wall after finally taking off her silver knickers. She looked coyly over her shoulder and fluttered her eyelashes at me. I wondered why she had decided to fuck me, not that I was complaining. I knew I’d never find anyone I’d love as much for all our fighting as k**s. I stepped up behind my beautiful lover and carefully lined my cock up with the starfish of her ass. With a soft grunt I thrust it in, Chelle pushing back against me as I did so, sinking me deep into her butt hole.
“Ooooh that’s gooood.” Chelle moaned. “Why did I put off fucking you for so long?”
“I couldn’t say Chelle.” I replied, plunging in and out of her ass. “But I am glad you did.”
“Oh god! You make me cum so quickly. Uuuuhhh!” She orgasmed but continued to respond to my attentions.
“Michelle, should I stop?” I panted, not wanting to.
“Don’t you fucking dare!” She gasped out. “Keep going until you cum.”
“Yes ma’am.” I replied, quickening my pace. I could feel myself getting closer to my own climax when Michelle came again, her ass muscles clenching around my thrusting cock. That set me off. I pulled back and squirted my jizz over her heaving butt cheeks and the backs of her fishnet-clad thighs. We were both huffing and puffing with our recent exertions as we made our way back indoors and up to the shower. We showered together, possibly a mistake, as we made love under the stream of hot water. And again in bed together before finally falling asl**p in each other’s arms like the night before.
We both slept late the next morning. Michelle woke first and I found her gently shaking me awake.
“My turn in charge again if I remember.” She smiled.
“Whatever you want Michelle.” I blearily replied, wiping the sl**p from my eyes.
“Careful what you promise me.” She grinned. ” I might just go all sadist on your ass.”
“If that’s what you want lover.” I truly didn’t care. I just wanted to make her happy, maybe for one last time. “Besides which, you’ve been torturing me for years.” I laughed.
“Sorry.” She said shamefacedly. “I was only joking anyway. No physical pain I promise.”
“Mental anguish then? You want to dress me as a girl again?”
“Of course! We both had fun with that didn’t we?”
“We did.” I blushed, somewhat embarrassed by my liking of the feeling of being done up as a girl.
“Good. Cos I have an idea.” She smirked. For some reason this wasn’t exactly reassuring. “First up: Shower and shave.”
“All over again?” I asked.
“My little s****r does NOT have stubble everywhere.” Michelle said in a mock stern voice.
“Yes ma’am. I mean, no ma’am.”
“Good girl. Now get!”
Michelle had already showered before waking me, obviously learning from the night previously. By the time I had finished with the razor she was dressed, in a pair of really tight jeans and a figure- (bosom!) hugging top, and was waiting for me as I came into her bedroom.
“First things first.” She said, picking up a roll of masking tape.
“What’s that for?” I asked hesitantly.
“Don’t want you bulging where girls don’t, do we?” She told me, tearing off a strip from the roll. She stuck down my dick and balls deftly, before I could get an erection, with several strips of the tape. “Bra next.” She said, handing me a different padded bra to the one I’d worn before.
“I thought you only had one of these?” I said, clipping it on.
“I never said that. I just showed you I don’t need them anymore.”
“You definitely don’t.” I laughed.
“Thank you. Panties.” She handed me a pair that were black satin in appearance, with lacy edging. I pulled them on, loving the feel of the material.
“Tights.” She announced.
“Tights?” I was surprised. Chelle gave me a stare. Shrugging, I took the hosiery and sat down to put them on. They seemed quite thick, but the touch of them on my recently shaved legs was quite pleasurable and they did make my legs look feminine. Michelle smiled as she saw me running my hands along my thighs.
“LBD.” She said, handing me a dress. A little black dress. I slipped it over my head and wriggled into it, smoothing it down over my hips. Again the material felt lovely as I ran my hands over it.
“Put your heels on and come sit at the dresser so that I can do your wig and make-up.” Chelle told me. I strapped on the shoes and plonked myself in front of the mirror. It didn’t take her long to attach the blonde hairpiece and apply the cosmetics. Again I was stunned by the view in the mirror: It just didn’t look like a guy looking at me.
“Now what?” I asked.
“We’re going shopping!” Michelle laughed.
“You mean, go out like this again?”
“It was all right before.”
“Well…” I was not convinced this was a good idea.
“Oh come on. I have a wonderful scheme planned.” Chelle enthused.
“Okay, okay.” I gave in.
“You’ll need this handbag. I’ve put everything you’re going to require in it.” She passed me a small black shoulder bag that went with the outfit. I took it and then followed her to her car.
I don’t know what I was expecting really, except it wasn’t a trip to the nearest city; twenty minutes by car. When we had parked I was sure we’d be off to some sort of clothing retailers, but instead we headed for the back streets. For a horrible moment I thought she was going to pimp me out or something, but that passed when she found the shop she was looking for; a shop selling ‘marital aids’. In a state of confused worry, I hardly dared move from where I’d stopped when we’d come in. Chelle was obviously looking for something specific, or possibly more than one thing, and she was soon back with me with a carrier bag, but not before I’d endured several lustful stares and a not very subtle attempt to chat me up. If I hadn’t been so scared I’d have taken them as a compliment, another worrying thought. Michelle led me back outside and walked with me to the end of the street.
“Okay then s*s, the bus station is just round the corner. I’ll see you when you get back.” She smirked.
“You’re just abandoning me here? What happens if something goes wrong or I get found out?” I was angry and terrified at the same time.
“There’s money and your phone in your bag.” She said calmly.
“If the people in the sex shop couldn’t tell you were male, why should anyone else?”
“See you in an hour or so. I have to go home and get things set for your return.”
“CHELLE!” I called out as she turned and walked away but she ignored me. I suppose I could have run after her and demanded she drive me home, but the confidence she had that I could pass myself off as a girl must have rubbed off on me. ‘Damn her!’ I thought; ‘I’m gonna do this.’
I caught the bus but was full of trepidation; it looked like it was going to be fairly full and I would have to sit next to someone. Looking worried, I found a seat and sat. A girl of about my age eased in beside me.
“Mind if I take this seat?” She asked with a smile. “It’ll keep the wolves from trying to chat us up.”
“Sure.” I managed to squeak in a high-pitched girlie voice. I caught a whiff of her perfume; it smelt divine. I briefly wondered if Chelle had ever thought of using some on me. I was horribly aware though of my new friends proximity; surely she’d be able to spot that I wasn’t a girl? I must have looked panicky.
“Nervous?” She asked. “Don’t take the bus much?”
“Not much, no.” I squeaked again. This was true; I rarely caught a bus these days.
“It’ll be fine.” She said. “Stick with me, I’m a veteran.” She smiled sweetly. “I’m Katie by the way.” She offered her hand.
“Michelle.” I replied, shaking her hand, picking the only girls name I could think of at the moment.
Katie chattered away the whole journey back. My contributions consisting of short answers to questions and encouragement to continue. She didn’t seem put off by this and by the time she rose to get off outside of town I was feeling a lot more comfortable in her company and was sorry to see her leave.
“Bye Michelle. See around some time.” She waved.
“Maybe Katie.” I waved back, amazed that my disguise had stood up to such close scrutiny.
A few minutes later the bus pulled into the station and I hurried to get off. I knew that there wasn’t enough money left in my bag for a bus closer to home so I started to walk; it was only ten minutes or so away. I concentrated on walking like Michelle did. By the time I reached our front door though, my feet and calves were aching; I wasn’t really used to wearing heels yet. I found the keys in my bag and let myself in.
“Made it then?” Chelle called out cheerfully from upstairs.
“Thanks more to a girl called Katie than you.” I said angrily striding into the room.
“Now, now, little s****r. There’s no need to be like that. I knew you’d be fine and you have to admit, you liked the attention, didn’t you?”
“Suppose.” I grudgingly agreed.
Michelle came up behind me and turned me around gently to reveal that she had got changed. Now she was wearing the body stocking from her secret case and something she’d obviously got from the sex shop; a worryingly big looking strap-on. The dildo jutted out obscenely from her pelvis, wobbling weirdly when she moved.
“Come on, cheer up. We’ve only got today. Mom and Dad will be back sometime tomorrow.”
“You’re right.” I sighed. “And you did warn me that it wouldn’t be easy for me today.” I managed a grin, my bad mood dissipating. “What do you want me to do next then?”
“I was wondering what sort of cocksucker you were.” She smirked.
“No where as good as you are I expect.” I said, dropping to my knees in front of her, the strap-on level with my chin.
“Flatterer.” Michelle smiled. “Go on then. You’ve seen me do it.” She encouraged me.
Shyly I poked out my tongue and licked at the tip of the plastic phallus. Then, remembering what Chelle had done, I ran it down the shaft and back up again. I looked up into Michelle’s supportive smile and the last vestiges of worry and anger went. I opened my mouth and swallowed the head of the fake dick. Moving my head forward, I took the dildo deeper into my mouth until I began to gag. I jerked my head back, coughing.
“Take it easy s*s.” Michelle soothed. “You don’t have to take it all in at once.” She patted the top of my head reassuringly.
“You make it look so easy Michelle.”
“I’ve had a lot more practice than you sweetie.” She said. “Have another go and try to breathe through your nose.”
“Kay.” I opened my mouth again, taking half the length on the dildo in.
“Ease your head back a little.” Chelle advised. I did and to my immense surprise I found I was practically deep-throating the strap-on. “I knew you could do it.” Chelle smirked. “Now move your mouth back and forth along it.” I did as she said, gradually building up the pace. Michelle was thrusting her hips in time with my oral ministrations. “That looks so realistic. ” She laughed. “It’s just a pity I can’t jizz down your throat and over your pretty face.” She added slyly. I have to admit to a little curiosity to what that would be like. Instead I stopped and sat back on my heels, drool all over my chin and the strap-on.
“This is all well and good Chelle, but I seriously doubt that either of us is going to get off this way.” I said.
“Eager to get to the next part are you?” Chelle grinned. I looked at the saliva-covered dildo and back up to her smiling face.
“Yes,” I said, giving her a big grin.
“Slut.” She laughed.
“Whore.” I rejoined in kind.
“So you want me to stuff this cock up your dainty little ass hole do you?”
“Yes ma’am.” I grinned.
“All right then. Pull down your tights and knickers and lie back with your bum on the edge of the couch.” She saw the puzzled look I gave her. “I want to watch your face while I fuck you.” She explained.
“What about the tape over my dick?” Already I could feel my cock straining against its imprisonment.
“Lets see shall we?” Chelle nodded.
I slipped my girlie underthings down until they were bunched about mid-thigh and then laid back as ordered. Michelle got to her knees and shuffled close to me. I raised my legs, exposing my ass hole and taped cock to her.
“I think the tape is coming off.” She said. And ripped it off.
“YEOW!” I yelled.
“Oh shush.” She laughed. “You knew all along that was going to happen.”
“Suppose.” I grinned. Peering around my legs I watched Michelle rub baby oil on to the strap-on with her fingers. It was strangely erotic. She began by easing her still oiled fingers in and out of my butt for a while; first one, then two, and finally three. Then she pushed the head of the dildo into my willing hole. I let out a moan.
“Hold your legs out of the way.” Chelle told me. I wrapped my arms around them and held them to my chest. My treacherous cock was already leaking pre-cum; I could feel it oozing down the shaft. Michelle pushed again and the phallus sank all the way into my butt much more easily than I’d expected. I sighed as Chelle began to fuck my ass. While she pounded into me I grabbed my dick with one hand and started to jerk off in time with her thrusts, almost as if I was fucking myself. In my highly excited state it wasn’t long before I came, and hugely; my spunk shooting into my tangled panties and tights.
“Oh, don’t stop Michelle!” I moaned.
As I was saying it, the door opened.
“WHAT THE HELL ARE YOU DOING!?” Mom screamed.