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"Kate darling, you haven't seen my red knickers have you? Only I'm sure I washed them and put them back in my drawer. You're sure you didn't accidentally pick them up by mistake?".
The passive aggressive accusation, camouflaged as the innocent friendly question. These days, Sophie and Kate often communicated like this.
The "squeeee, best friends foreverrr!!!!" energy that they'd started the year with was now a little frayed, dampened by the frictions of two months sharing a small and somewhat damp terraced house. Quarrels over shower times, dishes, abandoned ash trays, had stacked up. Petty resentments building. All the usual joys of shared living. They still were ostensibly best friends, still hung out all the time. But a little bit of trust had got lost somewhere along the way.
They'd been best mates through first year at uni, bonded over their shared private school education and love of skiing. Excitedly, they'd gone looking for a two-bedroom flat to share off campus in year two. But the lack of small enough places meant they needed a third wheel for what was now our shared flat. All their other girlfriends had already made their housing arrangements, so in desperation to get this place, they turned to a quiet, slightly timid and decidedly unthreatening male acquaintance from their course. Me.
We'd always got on perfectly fine, and the three of us had occasional DVD nights and trips to the local pub. But a lot of the time, they had their life, the girlie trips and rugby boys. And I had mine, studying, playing football, nights out with the boys. Well, that had been my life at least.
"Sophie, I swear I haven't got them. Red is more your colour anyway."
Twenty year old me wasn't fluent enough in girl to be sure exactly how, but I was pretty sure that was intended as an insult.
Kate was of course innocent of this crime. The lacy red item wasn't in Kate's room, or Sophie's for that matter. They were under my suit trousers as this very conversation took place, their soft fabric stretching over my backside, struggling to hold down private parts they had never been designed to accommodate. Sophie and Kate were at home already when I got back from the office, and I hadn't yet had the chance to safely change and return them to Sophie's drawer. As I listened to their argument, guilt at my violation rose up from my stomach and into my throat.
Wednesday and Thursday passed in a blur. As the boss had explained after Tuesday -- after he changed me forever -- he had meetings in London and wasn't around at all. So I had to endure two full days of my drab temp job with my two drab coworkers. Take an old file, look up the reference number, log it on a spreadsheet, scan the file, put the scanned file in the right folder on the database. Rinse, repeat. Kill me. This was the job, the real job, the one I actually signed up for. But after the events of Monday and Tuesday, it seemed ridiculous to be doing this, and then just going home at the end of the day. What sort of life was this? Luckily it required so little active brainpower, I could do it while daydreaming about what the boss had done to me.
I barely slept Thursday night. Lying in the dark of the pokey bedroom of my shared flat, I played back in my head every memory from earlier in the week. How he'd made me kneel to suck him, lick him, please him. How he'd fucked my face, fingered my little hole, then fucked me like I was nothing. How he'd cum in my mouth, cum deep inside me. Used me. Called me a slut, a whore, a sissy. A good girl. How I'd loved the last one.
Sophie's boyfriend Hugo was around again on Thursday night, and our shared dividing wall was once again thudding in time with his thrusts. Lying in the dark of my bedroom, hard as a rock, I listened as she begged him to fuck her ever harder. When I'd heard the same show on Monday I'd stroked my cock until I brought myself to orgasm, but today a different urge took me. Once again my hand slipped under the covers, but this time it slipped past my cock, down further and around until my fingertips reached my arsehole.
"... YES YES fuck me Hugo, fuck me harder..."
As Sophie moaned from the heavy thrusting of her giant rugby-playing boyfriend, my own fingers swirled around the entrance to my hole, just like the boss's had done on that sofa on Tuesday. Lying on my back, the angle was difficult, and my hand was cramping from trying to reach behind myself. I needed easier access. Unsure what to do, I raised my knees, altering the angle of my pelvis. Still a bit tricky. So I pulled my legs back and up further, bringing my knees back all the way to my shoulders, my feet raised up high above my head, my hole now primed and exposed. I pictured Sophie next door in the same position, with her heavy, oafish rugby playing boyfriend lying on top of her, pumping away at her while her little feet bounced on his shoulders.
I licked the tip of my finger to wet it, and began to gently swirl the tip around the entrance to my hole. Just like the boss had done to me on Tuesday, the first time anyone had ever touched me like that. The tingles of a million nerve endings activating from my tight little sphincter, starting small and gradually radiating out and up and down and through my entire body. Electric currents gradually moving over more and more of the surface of my skin. Bliss. Emboldened, I pushed my finger into the centre, pushing against the elastic resistance of my entrance. For a few seconds, stalemate, the door remaining firmly closed despite the growing pressure I was applying. Then suddenly PLOP, my index finger drove through and inside, a little "ohhh" escaping me as the muscles gave way.
As before, my sphincter immediately panicked at this intrusion, and tensed and tightened into a death grip around my finger. I remembered what the boss had said to me when this happened on Tuesday.
"Relax, just relax"
It took a few seconds, but the tension began to ease, the death grip began to loosen. And as it did, I started to slide my finger further up and inside me, looking for the magic button the boss had probed, the button that three days ago I didn't know existed. Another inch and suddenly BOOM there it was, and once again that fullness, that pleasure, so intense my brain could barely process it. That small ball of energy, growing with every stroke of my finger.
"... Oh fuck yes Soph, take my cock you slut..."
Hugo was speeding up. He always did that when he was close. As the thud thud thud got more urgent, I rolled my finger up and down inside me, keeping perfect tempo with the thrusts next door. As I lay back, eyes closed, my finger pushing firmly into my prostate in time with each of Hugo's thrusts, I imagined myself as Sophie, lying back, my ankles either side of Hugo's ears, getting pounded and being told what a whore I was.
"Oh ohhh I'm cumming Soph. I'm going to cum on your face. Hang on"
The thrusting next door abruptly stopped. I pictured Hugo straddling my face with his heavy frame, his cock just inches from my lips, his large hand furiously jerking.
"Urrrrrgrgrgrhrrrhhhhhhhh"
As my finger rapidly darted up and down inside me, I imagined huge gobs of his cum explode out onto my lips, my cheeks, my nose, my forehead. My face covered like those girls in that porn DVD I'd seen that time. I pictured Sophie lying next door, her face covered in Hugo's cum for real, and wish with every fibre of my being it was me.
I slid my finger out. I briefly thought about jerking my own cock, to give myself an orgasm like Hugo's, but for some reason that didn't feel right. I lowered my legs back down, pulled the duvet cover over myself, and fell asleep.
Friday. Finally. The day the boss was back.
I woke up earlier than usual, before my alarm even, and immediately felt bolt upright. Three days of anticipation but today was the day. He'd promised that the dreary coworkers would be away at some corporate away day. That it would just be us. That he had something special planned. I had know idea what that meant, and excitement and fear both competed for supremacy inside me.
Monday he'd just made me suck him after everyone had gone home. Tuesday he'd fucked me, taking my anal virginity and introducing me to sensations I never knew were possible. If today was indeed something special, it would surely involve something truly mindblowing. Shaving in the bathroom mirror while the possibilities ran through my mind, I had to consciously stop my hand shaking so as not to cut my face.
I practically ran down the street to the office, the butterflies in my stomach like rocket fuel, pushing me down the road at a gallop. As I passed each person, I wondered to myself what each would think if they knew that normal looking young guy walking down the road was heading off to be some old guys fucktoy, his sissy slut. Who would laugh, who would be disgusted, who would be turned on? I played my silly game all the way to the office door.
I bounded into the office a few minutes early, thinking that maybe I'd get there before the boss. But he was already there, sat behind his desk, in the middle of a phone call. Something about pension schemes, matched contributions, I don't know. Finance stuff I didn't understand. Who cares, soon he'd be done, then surely whatever he had planned would start. I sat at my temporary desk and tried to busy myself with the filing I was supposedly being paid to do, but I could barely concentrate.
The phonecall lasted an eternity, almost an hour by the time he put the receiver of the bulky desk phone down with a firm clunk. Hearing that sound, my heart dance and my pulse near doubled. What was in store for me now?
"Come in here"
I leapt from my desk, then, catching myself, resolved to play it a little cooler. I walked easily into his private office, closing the door behind me. On getting inside, I realised I hadn't thought of what to do or say next, so I just sort of lurked awkwardly, unsure what to do with myself.
"Take this."
A backpack.
"You can use that room."
He gestured at the door to the small, and somewhat grimey, single cubicle bathroom in the far corner of the office.
"Oh, and make an effort, yeah?"
Then he picked up the phone again, and started dialling.
"Matthew, hi, just getting in touch about next week...".
He raised his hand to shoo me out the room, before turning back to his desk, to talk to Matthew about next week. Feeling a little embarrassed, I traipsed out, across the room, and into the bathroom cubicle. The motion sensor clicked, and sickly yellow fluorescent light filled the room as the door closed behind me.
Standing in the bathroom, I laid out each item from the backpack one by one onto the change table in the corner.
A silky white blouse. A light grey, cotton pencil skirt. A pair of black holdup stockings. A matching lacy black bra and panties. A black wig, in a 1960s style bob. A dark crimson lipstick. A jar of ruby red nail polish.
Oh god. Ohmygodohmygodohmygod.
I stared, jaw agape, at the collection for a couple of minutes. The absurdity of it all bouncing round inside my skull. This is the "something special". He wants me to wear this for him. To dress up like a girl for his amusement.
ohmygodohmygodohmygodohmygodohmygod
I'd never thought of my figure as feminine before. I mean sure, I was kinda slender, and never really grew much in the way of body hair. At aged twenty, I still couldn't grow a proper beard if my life depended on it. But there's a difference between being slim and not very hairy, and looking like a girl. And I definitely wouldn't look like a girl, no matter what I wore. Would I? Suddenly nothing seemed certain, everything seemed absurd. As my mind raced I picked up each item in turn, running my fingers through the fabrics. So different to the guy clothes I'd worn every day of my life, so much softer.
The more I thought about it, the more I decided that only two things really mattered here. One, no one is here except us, for the whole day. No one will come in and see me. Two, the boss had ordered me to do it. Not asked, ordered. A week ago I'd have laughed and told him to fuck off. But everything had changed since then, EVERYTHING. Now, making this man happy, doing what he tells me, had become the single most important things to me. How I craved his approval, how I longed all day every day for him to tell me that I was a 'good girl'. In just a few short days, those two words had become everything.
A deep breath. Here we go.
I took off the men's shirt, tie and suit trousers I'd come to the office in. I slipped off my socks and boxers, now standing naked in the bathroom, looking back at myself in the mirror. Definitely a boy's body. This would never work, I'd look stupid, ridiculous, he'd laugh at me, maybe throw me out on the street for not being what he wanted. But I had to try. He'd told me.
I slid the panties up my legs, that was easy enough. Then the bra, which took forever. I was never good at removing bras from girls, embarrassing myself as I tried to unbutton them until they'd get frustrated and do it themselves. And I'd certainly never attempted to put one on before. Eventually, after much struggle, I figured out to button the clasp at the front, and then spin it round. I pulled on the stockings one after the other, nearly overbalancing as I ham-fistedly pulled them up my thighs. I looked at myself in the mirror in my lingerie. Still a boy, all the lines and curves in the wrong places for a woman. But yet, but yet. Something was different. I couldn't say what.
I stepped into the pencil skirt and pulled it up my legs, before fastening it round my waist. Being taller than most women, it sat a little high, a good few inches north of my knees, showing off the tops of my stockings. But then, the boss probably wouldn't mind that. I slipped on the blouse, that was easy at least. But now, the lipstick and the nail varnish. How to tackle that, I had no clue.
I tried applying the lipstick, my hand steady and even. Or so I thought. When I pulled my hand away and looked in the mirror again, I realised I'd smeared a good half inch of crimson all round my lips rather than just on them. A circus clown in a dress. I frantically dabbed round my mouth with hand towels until I'd cleared up most of the spillover, and it looked (almost) like it should. Then I remembered something. I'd seen Sophie putting on her lipstick, and then putting a little square of tissue paper between her lips and delicately dapping down, taking away excess and leaving it looking neat. I tried the same, while wondering what she would say if she could see me now. Then the nail polish. I realised that excess would not be so easily removed here, so I went as slow as possible, meticulously painting each of my fingernails one by one until all ten were a bright ruby red. They looked a bit streaky, but from a distance they seemed about right. It would have to do. Then finally the wig, a dark shoulder length bob, the sides curling back down towards my neck in a circle.
As I stared into the mirror at the figure looking back, I felt quite different to how I'd expect. I thought I'd cringe in shame at the stupidity on my appearance. But, while I looked clumsily thrown together for sure, somehow it looked like me. Maybe more like me than before.
There were no shoes in the bag, and my men's leather brogues just wouldn't look right. So I packed all my boy clothes and shoes into the backpack, and stepped back into the office in my stockinged feet.
I tiptoed into the boss's office. He was still on the phone, either to the same guy or someone new. Who cares. Looking me up and down, he silently mouthed "good girl" with obvious lust in his eyes, then turned his attention back to his call. He was pleased. I had pleased him. I was a good girl. I practically floated out the office and back to my filing.
All day I waited for the boss to exit his office. Lunch came, and the calls finally stopped, but he just walked off out the office without addressing me, and didn't come back until an hour late. Then straight back onto the phone, endless calls with god know who about god knows what. I began to feel desperate. I made a point of walking into his office with files, stretching up to high places and bending over to access low drawers. And he would look, and smile. But then back to his phone. Why would be dress me up like this if he didn't want to look at me? To play with me, to use me? What could I do to entice him? I caught this train of thought, and chastised myself for being so pathetic.
It was now almost five pm. Nothing. I'd given up even the pretence of filing a couple of hours ago, now just sitting at my desk, fiddling with the stationary and sulking. Then suddenly he appeared from the office, pausing to stare admiringly at my figure from across the room.
"You did make an effort. Good girl. Come on, we're going for a little drive. My car's just outside"
So desperate had I got by this point, I didn't care to ask where, or why. I just knew that I needed to obey. I scanned round the room, trying to find my bag of boy clothes so I could slip them on for the short walk from the door to his car.
"If you're looking for the bag, don't worry. It's already in the car."
Panic. I had to walk to the car dressed like this. It was only five yards. But it felt like five miles. I bowed my head, and steeled myself for the scariest ten seconds of my life. I felt like I might explode from the anxiety. I had never felt more alive.
As we wove our way through the city centre streets I realised I was physically shaking with adrenaline.
We were now on one of the busiest streets in the town centre, crawling through the rush hour traffic, travelling maybe a couple of hundred yards in ten minutes. In that time dozens, no, hundreds of people had walked passed us, leaving work, heading home, or to the pub, or to a friends house, or to one of the hundreds of other places a normal person might go at 5pm on a Friday. Not dressed up in girly clothes in the passenger seat of an older man's car, heading off to god knows where to do god knows what.
At this time of year it was at least already dark, and what little light there was from the streetlights reflected off the windows in such a way as to make seeing into the car almost impossible. I knew that, of course I did. But as far as my nervous system was concerned, I might as well have been carried behind the car like a parade float, with blinding spotlights, and a tannoy announcer balling "Look here look here! Everyone look at the little sissy slut! The freak! Doesn't she look ridiculous in her little skirt and knickers!". I imagined all the decent normal people staring at me, laughing at me, threatening me, telling me what a pathetic little perv I was. I looked down to my hands balled up on the top of my rights, realising they were shaking.
Finally we were up to the traffic lights, almost ready to escape the town centre, escape the sea of looks and judgement I had created in my own mind. Turn green, turn green, come on, hurry up. But no, the crossing lights kick in, and a gaggle of people cross in front of us. A group of guys in suits, all braying loudly with that "look at me" camaraderie that had always felt so forced and unnatural whenever I'd attempted it. A middle aged couple arguing about something. A group of women in catering uniforms with their arms hunched in front of them to repel the cold Yorkshire air. And finally, a big group of my fellow university students, presumably off for a happy hour pint before the late evening prices kicked in. My eyes moved down the line, one person to the next, all the way to the last two figures. My eyes stop. My heart stops. My whole nervous system stops. Every ounce of breath leaves my lungs with a gasp that startles the boss in the drivers seat.
Sophie and Hugo.
The logical part of my brain attempts to reassert control. "They can't see you, they can't see you". It's true. But my body's not listening. I can't breathe, my legs rattle up and down, shaking with the adrenaline coursing through them. Sophie and Hugo reach the pavement, and to my abject horror, turn left, about to walk right past my passenger side window,
"they can't see you they can't see you they can't see you" my brain blares over and over to myself in the darkness, heard but ignored, like a car alarm in the night.
They're walking right past me now, giggling at a shared joke, arms round each other's waists. They're now so close they can touch my window. In irrational panic, I fling up my hands to cover my face, and angle my head so the bob wig obscures as much of me as it can. But the sudden movement seems to draw Hugo's attention, and for a brief moment, a single heartbeat, it feels as if our eyes meet. And then as fast as it happened, they're past us, off into the night. In panic, I look into the side mirror, to see if they turn back. If Hugo recognised me they surely would, then they'd tell everyone at uni and my life would be over. Oh what a stupid reckless fool I've been! But they keep walking, never even looking back. I take a lungful of air for the first time in what felt like an eternity. We drive through the traffic lights and head out of town, first onto the busy bypass before winding our way down a quiet road cutting through the rolling hills of the Yorkshire countryside.
"Pour me a drink" he says from the sofa, leaning back into the cushions.
He gestures to the small cabinet in the corner of the living room of the little country cottage. I grab one of the crystal tumblers perched on the top, and open the little mahogany doors at the front. Bottles, expensive looking ones. Scotch whisky, cognac, something called 'sochu' with some kind of Asian writing on it. Back in my flat I might have a couple of cans of Fosters, on a good night. Nothing like this. Unsure what to serve him, I opt for the scotch, pour a little into the tumbler, and totter back over to him. I tried to do so in a way that gave off an air of grace and sophistication, but being totally unaware how to do so, I gave off nothing of the sort.
I hand him the glass, with a nervous "here you go sir". He takes it without saying anything, or even making eye contact with me. Instead, he clicks the fingers of his left hand, then points his index finger to the floor by his left foot. I don't understand the gesture, so just stand motionless while staring at the relevant bit of carpet.
"Kneel there". His tone shows how my foolishness has irritated him.
Embarrassed, I scramble to move. I want to please him, I want to be a good girl. I drop quickly to my knees, to the side of him by his left foot, my feet tucked underneath me, my hands on my the top of my stockinged thighs, my head bowed, as if at church in prayer.
The boss takes a long, slow sip of his whisky, holding it in his mouth for a moment before draining it back with a deep mmhhmmmm. Looking straight ahead, entirely in his own world. He picks up a slightly dog eared copy of that morning's Daily Telegraph, and absent mindedly flicks through its pages, sipping his whisky. It is as if I've vanished. This goes on for what was in reality probably no more than ten minutes, but felt like years.
The room may be silent, but in my head, a cacophony. To start with nerves, anticipation, excitement. Then after a few minutes of being ignored, confusion. Then a few minutes later, a rabid yearning to be allowed to please him, to be told what to do, to suck his cock and let him put it wherever he saw fit. I knew I needed to stay still, to do as I was told. But it took every part of my self-control not to start desperately pawing at his crotch, like some affection-starved puppy.
Good god but how much had changed since Monday.
Then without notice, he slowly turned his head and looked straight into my eyes. Unable to hide it, I tilted forward, my whole demeanour lifted in anticipation. He's ready for me now. He wants me to please him.
"Well well, someone's eager to get their hands on some cock" he chuckled. A blush of heat filled my cheeks. It wasn't until that moment that I'd even admitted to myself how desperately I wanted him.
"Don't be embarrassed, all good girls know like to please their man". His tone was kinder again, gentler. As his words came out, he gently stroked my check with the thumb of his left hand, slowly sliding it across until it met the corner of my mouth, and slid slowly across my lips. When it reached the middle of my mouth, without thinking I gently kissed his fingertip. He smiled.
"Your contract finishes this week. So you can't be my employee anymore. But you can be something else if you like."
I'll be anything. Tell me what you want and I'll do it. Anything. ANYTHING.
"You can be my girlfriend"
Five hundred thoughts and emotions all burst into voice in my head at once. There was still a part of my brain that wanted to burst into laughter at such an absurd idea. I'm a guy! I'm straight! What do you mean your girlfriend?! Monday morning that would have been the only voice. But today was Friday, and today that voice was barely a whisper, drowned out by another thought, booming across my mind. And that voice said yes, yes, let me be your girlfriend. Let me exist for your pleasure, let me be a little fuck toy for you. This is who I am. This is home.
"Would you like that?". His voice snaps me back into the room. I open my mouth to speak, but not for the first time with the boss, no words come out. Instead I smile, a shy, foolish smile, and nod my head awkwardly.
"Good girl"
There they are, the words I love to hear.
"So here's how this is going to work. Monday to Thursday you can do whatever you normally do. Go to lectures, go out with your friends, do whatever it is that you do. But Friday to Sunday, you're mine."
I gulp. My cock twitches against my panties as the idea percolates in my head.
"I expect you to take a spare key I'm going to give you today, and let yourself in before I get home at 5.30pm. When I get home, I expect to see you dressed up nicely for me, with my drink in your hand, and ready to take care of me. I expect an obedient, well behaved little slut, who will do whatever I say, and I'd better get it. Do you understand?"
Another shy, awkward nod from me. My heart is pounding in my chest. He pauses, and takes another slow sip from his whisky.
"Good, so that's settled. Well, I suppose you're desperate to take care of me aren't you? Is that right you little sissy slut?"
Another nod, this time with a nervous giggle.
Suddenly the boss leans in, his face inches from mine. "Well there's just one thing I need if I'm going to let you touch me. Do you know what that is?"
I shake my head, realising how the dynamic has shifted so swiftly. Now HE's going to let ME touch HIM, only if I do something else first. I realised the absolute truth of it though. I would do anything.
"I need you to beg. Beg to be allowed to take my cock out and suck it. Beg for me to fuck your little slut mouth, and your little fucking hole. Beg, BEG, you whore"
Monday I would have baulked at this. But today is Friday, and today is a different day. And I am a different person.
"Please sir, please let me suck your cock, please fuck my little hole, you can do anything you want to me, I'll be your obedient little slut sir, please, pleeeeeese..."
I tail off into nothing. The boss sits there unmoved, then a smile grows across his face, the self satisfied grin of a man who's victory is total, who's dominance over me is now complete and unquestioned. I would do anything to satisfy him. I need to please him. I need to be a good girl. We stay like this for another thirty seconds that feel like a thousand years. Then I hear what I want to hear.
"Very well, you may start".
I don't need asking twice. I practically leap across from my position by his side until I'm kneeling between his spread out legs while he leans back into the sofa. My hands immediately tugging at his belt buckle, pulling open the fastening, dragging down the zip of his suit trousers. I realise how fast I'm moving, how obvious I've made my desperation to get at him. NOw unzipped and open, I reach my varnished fingers inside to pull his already half engorged cock through to gap on his boxers. I stroke him up and down gently, holding him just inches from my face.
"Don't use your hand. I can wank myself off if that's what I wanted. Use that little whore mouth of yours"
I've displeased him. Disaster. I can fix this. I must fix this. I'm need to be a good girl.
I release him from my right hand, and slide my lips over the tip of his dick. I remember what seemed to please him last time, so to begin with I gently just the tip in my mouth, gently swirling my tongue round in circles and figure eights all round the head. I caress the underside with the base of my tongue, before flicking the tip of it round and above, trying to stimulate every millimetre of his hardening cock.
Then slowly, slowly, I slide my head down, my tongue rolling down the length as I do, until I'm all the way into his crotch, his balls on my chin, my face buried deep in his mound of pubes. That smell in my nose again, that deep musky mix of sweat and precum. I inhale deeply, an addict getting their fix. He hardens as I do so, growing deeper into my mouth, pushing back into my throat, pulsing against me. I hold for a few seconds to adjust to his growing volume, before sliding back up his cock again, dragging my tongue, never breaking the seal of my lips around his shaft. Then I'm back up at the head, and it's time to start the rhythm again. Tongue swirl, then down down down the shaft until he's in my throat, then pulling back up, up, up, dragging the tongue. Up down, up down. For a few minutes this is all we do.
"Look at me"
I look up to his face, our eyes meeting as I take his full length deep into my mouth. He almost purrs as I do.
I reflect on how much gentler this was than last time. On Tuesday he was grabbing my head and fucking my throat almost from the first moment, a rough almost angry animal, furiously using me for his own pleasure. Today he was lying back, luxuriating in my worship of his dick, letting me control the pace. Perhaps he was a different person in the security and comfort of his own home. Perhaps it was the fact I was dressed like a girl. Whatever it was, it felt different. I held the eye contact as I slowly slid my mouth back up his length. Impulsively, I think out a desire to look coquettish, I pulled him fully from my mouth, licking the tip of him with my cock, bringing up my right hand to stroke his shaft while I did so. I wanted to look sexy for him, to please him, to be a good girl.
"I thought I said not to use your hand. Do you not understand simple instructions?"
The tone has changed. He's irritated. I've screwed up.
"If you can't do as you're told then you can go home now. Get out, now"
"No please sir I'm sorry. I won't do it again. Please let me suck you sir please I'm so sorry pleeeeeese"
Even in my new state, the new person I am now, I realise how especially pathetic this sounds. Kneeling there, dressed up in a skirt and stockings, with a cheap wig and badly applied lipstick and nail varnish, begging for the privilege of sucking his dick. A wave of shame rolls through me, flushing my cheeks and making my stomach not. My cock twitches under my skirt, and I realise the indelible link I've made in my own brain between being degraded and being aroused. I know in that moment I am never going back.
The boss looks down at me for a few moments, seemingly weighing up what to do, the annoyance still plastered across his face.
"Hmmm. I'll give you one more chance. But first, I'm going to take temptation out of your way."
I have no idea what this means. My body quivers with nervous energy as his hand reaches to his right and under the sofa cushions, pulling something out that he must have stashed there earlier.
"It seems to me that the only way I can be sure you'll do as you're told, is if you have no other choice."
He places a hairy hand on the top of my head, pushing it down until my face is down in the carpet in front of him.
"Put your hands behind your back. Now."
I obey without hesitation. I am a good girl.
He reaches over me, grabbing my right hand, then wrapping something around it. It is cold, and feels rough against my skin. I think it's leather. I hear the crackle of Velcro, and feel the tight grip of the leather around my right wrist.
"Give me the other one"
I stretch my left wrist up my back until its as close to the right one as I can get it, and feel the same sequence. The coldness, the crackle, the tightening. My wrist shackled together behind my back, my face on the floor, my bottom high in the air. Trussed up and ready to serve, like a Christmas turkey.
"Now get your face back up here"
With no hands to support me, I have to engage my core to lift my head back up to crotch level. And there is his cock again, hard and pulsing, striking forward towards my face. I realise it has only been a minute or two since I last had eyes on it, but I how much I've yearned to have it back even in such a short absence. I open my mouth hungrily and take his full length inside me.
"Now hold still slut".
I knew by now what this meant. He was going to face fuck me with all his might. My job was to be still, to not gag, to provide a convenient hole for him. But the fact that my hands were now tied behind me made me feel more vulnerable still. I really was his to use as he pleased.
He stood up from the sofa, holding my head in place with a big hand either side of my skull. And then, with no build up, no gradual ascent, he begins thrusting into my open mouth, pushing roughly into the back of my throat with each angry pump.
The first thrust is so aggressive it catches me by surprise, and my gag reflex yelps in protest. I somehow manage to overcome the urge to puke, but my body responds by producing an ungodly amount of saliva, filling my mouth. A feeling of panic washes over me, as the saliva fills my throat and I struggle to draw breath into my lungs.
"Yeah, that's it, take my cock you slut"
He doesn't care. His pleasure is all that matters.
With the next thrust he doesn't pull back, but stays buried deep into my throat, my nose crushed closed against his pelvis. His throbbing head, and the saliva filling my mouth, almost entire closes my throat. The panic in me grows as I desperately struggle for air.
"Just relax, just relax. Sluts like you need to know how to take a cock properly. I'm not coming up until you relax"
There are many things I'm feeling in this moment, but being relaxed is not one of them. But I realise how helpless I am here, restrained, kneeling before him. I have to relax. I have to be a good girl. Mind over matter. I focus every fibre of my consciousness on calming my spluttering, to no longer writhing in panic. After a few seconds I am still. And while I am very far from calm in reality, I have obviously done a good enough impersonation of it to satisfy him,
"Good girl."
He pulls out of my mouth. As his cock finally leaves me, a river of spit and sputum follows it, barrelling down my chin and onto my blouse, before settling down into the tent in my skirt caused my now rock hard cock. I move to wipe my face, before the rough pull against my writst reminds me that my hands are stuck behind my back, so my chin and lips stay wet. I gulp great lungfuls of air, the relief mixing up with the now familiar blend of shame and arousal.
"Come with me"
Not that I am left with any choice in the matter, as the boss grabs hold of the chain linking my two wrists, and begins marching me forward, up the stairs of the cottage, a dog on a lead, down the short hallway to the master bedroom. The room is tidy, organised, sparsely decorated. A small dresser table sits in the corner, a shaving set, comb and nail clippers, lined up neatly. A small closet. And a large double bed, awaiting my arrival.
"On the bed, face down"
The aggressive tone is back, a sergeant major on the parade ground. I comply immediately, awkwardly shuffing first one knee then the other onto the end of the bed, before allowing my head to fall forward onto the beige bedspread. This action cause my skirt to hitch up a little, exposing almost my whole backside to the boss as he stands behind me. I feel him release his grip on my hand restraints, and then a finger sliding along the lacy fabric of my panties, running up and down the crack of my arse. Then the underwear being tugged down, until it's half way down my thighs. I am open and exposed. I know what happens next.
The cool splash of the lube as he squirts it directly from the bottle onto my hole catches me surprise, and I let out a little moan, which I supress in case it displeases him. Then the finger returns, swirling in little circles, just like he did Tuesday, just like I did to myself last night while I listened to my flatmate get fucked. Those little circles, teasing the entrance to my hole, each one sending those same bolts of lightening up through my body, that same feeling of bliss, of euphoria. How had I gone so long without realising I could feel this good? Nothing would ever be the same.
Then the pushing at the door, the firm pressure before POP, his finger is inside me, stretching my sphincter, filling me. This time I wasn't caught by surprise, but the feeling was so overwhelming still that I couldn't help but moan out again. But today it was different, not surprise and panic, but a moan of joy, of a deep itch being scratched. A slut's moan. I managed to relax the death grip round his finger much quicker this time, and within a few seconds the boss felt able began to push his index finger in and out, in and out, each entry going a little deeper. As he slowly fingered my tight little hole, that glorious swell gradually grew inside me once more. That ball of warm energy, starting small, growing slightly bigger which each gentle push of the finger. I cooed in delight with each press against my prostate.
"What a whore you are".
I couldn't argue.
Sensing I was loosened up to his satisfaction, the boss pulls out his finger. With my face buried in the duvet, I wait for what I knew was coming. The hard, pulsing thickness of his cock, pressing against my hole, pushing away my body's resistance. In my imposed darkness, waited, my skin, my mind, my whole nervous system on fire. I was still a little scared, remembering the intensity of the feeling last time. But also desperate to feel him inside me, to be filled up, to feel the electrticity and the warm energy, and to know that I was being used as his little fucktoy. I felt how hard my own cock was, but with my hands tied, I couldn't have touched it even I'd wanted.
No warning, no preamble. With one solid thrust, he was inside me. His cock jammed hard against my prostate, not a little tickle but a heavy thud. I felt an intense fullness, no room inside, the pressure bursting out and up from deep inside. But not just my body. my brain emptied every thought or emotion, everything that wasn't about processing the sensation of his hard cock inside me. There was no space for anything except this intensity I couldn't control. I was being fucked. I was being used. That was all that existed.
Hands tightly gripping me by the waistband of my skirt, the boss started to thrust with the same aggressive intensity with which he'd fucked my mouth a few minutes ago. My muscles were loose from the finger, but his cock was big, so my sphincter struggled to relax enough to let him in easily, giving a sharp sting with each pump. But despite that sharpness, the feeling was incredible. That warm little ball that had been building slowly against his finger now felt like it was doubling in size with every thrust, until it felt like it filled my entire body.
"Oooh your tight little hole feels so fucking good, you dirty little sissy whore"
I couldn't hold back, I didn't want to hold back. I panted and moaned like a whore with each thrust, surrendering my self entirely to the feeling consuming me. Surrendering to him. With the soft cotton of the blouse bouncing against the skin on my back, and the soft fabric of the stockings teasing the skin on my legs, I felt a full body bliss unlike anything I'd ever experienced. I was in heaven, every square inch of my body singing for joy, the feeling of nirvana so powerful I couldn't hope to contain it, just give myself up utterly to it. I was his sissy whore. He could do whatever he wanted to me. I wouldn't just let it happen, I would delight in every second of it. This was who I was. I was home.
Then suddenly, nothing. He's pulled out. A wave of emotion floods over me, and I feel bereft, grieving this sudden and heartbreaking loss. Absurd as it sounds, I feel like I could cry. Then the rrrrrrrrrippp of the Velcro of the restraint on my left hand being ripped open.
"Turn over slut"
"I flip my body round, now lying on my back on the duvet, the boss standing before me at the foot of the bed, his cock twitching with excitement. Suddenly he lurches towards me, causing me to flinch involuntarily in fear. Before I know what is going on, he grabs both my wrists, jerking them violently above my head, before yanking my slim body up towards the pillows. I open my mouth to say something, but before I can get a word out, he pulls my hands towards the wire frame of the bed head, interweaving the chain and resealing my left wrist. I realise what has happened. My hands are now tied above my head to the bed itself, exposing my whole body to him. He grabs one of the pillows, and tucks it under my bottom.
"Feet up in the air".
I don't need to be told twice. I pull my knees back until my ankles are hight up in the air, either side of the boss's head as he starts to reposition himself between my legs. Looking up, I feel more girlie than ever, letting myself be fucked missionary with my skirt and tights now in my field of vision. Just like I imagined Sophie last night, like I've imagined her many nights.
This time, when the boss thrusts there is almost no resistance. My passage yields immediately and he shoots straight up and in, slamming against my prostate so hard I yelp out almost at the top of my voice. He doesn't pause, just hammering immediately, with a speed and power that causes me to almost entirely lose control of myself. I buck and moan, shaking like a rag doll and he piledrives me down, my hands flapping helplessly above me and clanging into the metal frame.
"Tell me what a sissy slut you are. TELL ME." he bellows without breaking his furious pace or rhythm. "TELL ME!!!"
"... iiiiiii'm a siiiiisssssssyyyyyyyy sluhhhhhhht..." I barely cry out between breathless moans, using what little conscious control of myself I have to get the words out.
"TELL ME YOU'RE A DIRTY WHORE"
".... iiiiiiiiii'm a diiiiirty fuckkkkkking whooooooore....."
"TELL ME YOU'RE MY SISSY FUCKTOY"
I try to do what I was told again, but couldn't. There just wasn't enough brain function left, not enough body control. My mind had left this plain of consciousness and all that was left was physical reaction. The intensity of feeling was just too great, and all that was left was to give myself over to it.
My limbs started to shake uncontrollably, my lungs let out just one long noise, like an animal caught in a trap. Every nerve ending in my body was seemingly spasming at the same time. I looked down my body, and saw cum uncontrollably leaking from my twitching cock, sending a steady flow up onto the fabric of my hitched up skirt. For about ten seconds all I could do was jerk, spasm and moan, as if someone had just plugged me into the mains.
All of this seemed to send the boss finally over the edge. When I stopped convulsing, he pulled out his cock, and immediately lurched up my body, until he was sitting on my chest, his heavy thighs pushing into my shoulders. He jerked furiously at his cock, but it only took two or three strokes before he exploded all over my face.
"URRGRRGRRGGGGHGGHHHHHH"
Great rivets of spunk, one after another, all over my lips, my cheeks, my forehead. Some was in the wig, some dribbled down from my chin onto my neck. I again lurched my hand to wipe myself, before the tug of the chain reminded me that my hands were fixed above my head. So I had no choice but just to lie there, trying to catch my breath, his cum slowly oozing across my face.
The boss takes a deep breath to compose himself, before getting up. Then, without even looking in my direction, he wanders off down the corridor to the bathroom. I hear the sound of the shower. I am abandoned on the bed, my hands still tied, my girlie clothes still on, my face still covered in his cum.
He's back in the room, unlocking the cuffs.
"You can go now".
I awkwardly raise myself up from the bed, grabbing a tissue from the dresser to wipe his cum off my face, and head downstairs. I open the front door when the I realise that I'd somehow forgotten I was still in the blouse, skirt and stockings. I hear the boss's voice boom down the stairs.
"Your boy clothes are in the boot of the car. I left it unlocked. You can catch a bus from the end of the road."
With fear in each step, my eyes darting in all directions to check I wasn't seen by some nosy neighbour. I sprint out to the car, before hurriedly throwing my boy clothes on over the top of my outfit. Then down the road, waiting twenty minutes at the boss stop, my calm exterior hiding the whirlwind of emotions swirling round inside me.
The key turns in the door. I look up at the clock. Five thirty pm exactly. I leap up from the sofa, and straighten the little black cocktail dress I'd bought earlier that week from a clothes shop a couple of towns over. I check my wig and lipstick once more in the mirror, and run my hand down my freshly shaved legs, just to feel their new smoothness again. I grab the already poured whisky, and totter to the door. As the door opens, I smile a beaming smile, and hand the drink over. Without saying a word, I drop to my knees.
"Good girl."
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