The Intern Who Became a Sissy 02

As I staggered down the road, the cold reality of what had just happened hit me. I had sucked the boss's dick. A much older man, older than my father. I'd kneeled in front of this man, with his greying side parted hair, his sensible suit, his straight-laced accountant vibe. I'd licked and sucked and done anything I could to please him, everything he ordered me to do. But not only had I sucked his dick, I'd let him call me a girl, a slut, a whore. A sissy. What had come over me to make me do such a thing? I was straight, I liked girls, I don't do stuff like that.

Remembering the feeling of his hands firmly holding my head in place as he fucked my mouth. How I'd kneeled in front of him so submissively, looking into his eyes, mouth open, tongue swirling for his pleasure. The taste of his cum still lingering on my tongue. The words repeating in my brain over and over. Slut, whore, sissy. Unwilled, my own cock firmed and twitched against my zip as I walked. My trance was only broken by the screech of the brakes of the number 72 bus. I lurch back off the road in panic.

Standing on the cold pavement, I reflected on the fact that I just almost got run over because I was thinking so hard about sucking cock that I wandered into the road.

"Get. A. Grip."

Consciously focussed on actively expelling all of these new and horrifying feelings from my head, I carefully cross the road and start the twenty minute walk back to my shared student flat. I turn my thoughts to the university work I have to do this evening, what food I have in the fridge, when time I have football training tomorrow evening, whether it might rain later. Anything, literally anything, except what I'd done -- what I'd had done to me -- in that small office just off the high street.

The flat was dark and silent when I opened the door. "Sophie? Kate? Anyone home?" I called out, hoping to hear nothing in response. No, empty, home alone. Good. Can't deal with chit chat right now. I close the door behind me and walk into the little shared living room. No sign of either of them. They must be in the library, or a friends. Or maybe their boyfriend's flats. Sophie in particular was always hanging round with that prick.

A short and skinny blonde, Sophie looked like a decent blast of wind would send her floating off down the high street. She was very much what you'd call a girly girl, all pink tops and bright nails and pencils with fluffy pom-poms on the end. This was only a little undercut by a deceptively deep and gravelly voice, a gift from the half pack of Marlboro Lights she burned through each and every day.

I imagined Sophie lying on her idiot rugby playing boyfriend's unmade bed. She'd gone to some posh all girls boarding school somewhere down South, so it was apparently compulsory she date some equally posh boarding school moron from somewhere else down South. The immutable English class system is never more rigid than on a university campus. I would never get a girl like her.

Staring at the living room wall, I pictured her lying on his scruffy sheets in those bright red panties and bra I once glimpsed her in through the crack of her only partially closed bedroom door. Now she's lying with her head in his lap, sucking him while her cute little bum points in the air, his thick fingers playing with her. Now he's pulling her hips in front of him, yanking the panties down, thrusting inside her pussy while she moans and begs him to fuck her in that deep posh private school voice of hers. "Please fuck me, please cum in me". Her blonde bob of hair flicking back and up and down and across her face while he's pumping, thrusting, grunting, cumming...

I turned in fright at the sound of keys in the door. I should bolt for my room but I stand their frozen in panic. Not for the first time today. At the last possible second, I yank my shoulder bag in front of my groin to mask the erection in my pants.

"Mark is that you? Why are you just.... standing in the dark?"

"Sorry Soph, just got home myself, was a bit lost in thought haha, you know, erm..."

I tail off into nothing.

Only partially disguising the look of unease that spread across her face on seeing me standing silently in dark living room, Sophie dumped her bag by the door way and started rummaging in the cupboard for tea bags.

"Jesus Mark, are you sure you're all right? You're being a bit weird, you know?"

No no, I'm fine. Sorry Soph. Just a long day haha.

She softens a little, no longer on edge. Filling the kettle, while absent mindedly twirling a teaspoon between her delicate finger, the pinkie nail painted a playful yellow. "How was the first day at the temp job? Was it as boring as you thought?"

My cheeks flushed. I knew she couldn't have known what had happened. How could she? Impossible. But still, a flash of heat and electricity shot through my nervous system as she said it. Guilt and shame and fear of exposure, but undeniably also excitement. I took a careful breath. Be natural, be cool.

"No, nothing at all. Sooooo boring. Just paperwork all day. Anyway, I'm pretty tired from it and I think I the fluorescent lighting gave me a bit of a headache, so I'm just going to lie down in my room for a bit ok".

I make an effort to walk extra normally to my room, which of course makes me look extremely abnormal. Sophie gave me a final quizzical look before returning to her tea. I close my bedroom door, and lie back on my bed. It's only 6.30pm, but the emotional toil that this bizarre day makes me feel like I've been awake for weeks. I fall asleep in my clothes.

I wake feeling unrested, uncomfortable, disoriented. I look over at my clock alarm -- 11.17pm. I try to go back to sleep but my brain is already up. Resentfully I trudge into our tatty shared kitchen in search of food, drink, something, anything.

All the lights are off -- it's just me again. Kate still hasn't come back, must be staying over at her boyfriends. And no sign of Sophie, she must have done the same I guess. Not finding anything worth eating in the fridge, I sat at the kitchen table, when a single thought bolts to the front of my brain.

My homework from the boss.

As I sat in the semi dark room on my own, I remembered what he'd asked -- no, what he's ordered -- me to do.

"You're going to steal a pair of sexy panties from one of those female flatmates you mentioned. Something slutty, just like you. You're going to put those panties on, and admire yourself in the mirror. You're going to make yourself cum while wearing them. And then you're going to wear them to the office tomorrow."

Even just thinking about it made my heart thump in the back of my throat. I couldn't do it. It was a violation, a breach of trust. I know I wasn't exactly best mates with Sophie or Kate, but they had always been sweet enough to me. I couldn't steel their underwear. The very idea was as absurd as it was immoral.

And yet.

I remembered the firmness in the boss's voice when he'd given me my assignment. And as I thought that, came that strange feeling I'd had earlier. I want to please this man. I need to do what he says. I'm a good girl.

I physically twitched in my chair, as I reacted to my brain's own choice of words. A good girl. Why was I talking about myself like that? I'm a guy. A GUY. This is stupid, ridiculous, I need to stop this. I can't think like this. I can't BE like this.

And yet. My brain started throwing out justifications. Bullshit ones of course. Nothing would make it OK. But they kept coming.

"It would only be borrowing. They'll never know. They won't notice one pair missing. I'll wash them and put them back the next day and everything will be fine. It doesn't make you gay. It's just a bit of fun. Don't be a prude. It's no big deal."

There was part of me that knew the nonsense of this story I was telling myself, these excuses I was making. But right now, that part of me wasn't in control. Right now, the part that had made a promise to the boss was in charge. So I walked down the narrow hallway and opened Sophie's bedroom door.

Sophie's room was always pretty messy. Clothes on the floor, mugs, papers and cigarette packets on her desk. Adrenaline coursing through me, I danced around the various tops and sweaters in my path until I was by the small chest of drawers in the corner. My heart thumped in my chest, my head rushing. This was wrong. But we're hear now, might as well just do it. Realising I had no idea where anything was, I opened drawers at random. The first was filled with blouses and shirts, all tossed in and higgledy piggledy. The second was gym stuff. But when the third opened, I froze still. My mouth fell open and a soft little sigh came out. This was it.

Safe, comfortable pants for everyday wearing. Bras of all kinds, bulky sporty ones for the gym, and small black, delicate ones for earing under shirts. Giddily, I teased their fabric between my fingers, imagining Sophie wearing them. Stretched, tired looking ones. Brand new, box fresh, brightly coloured ones. Soft white cotton ones, skimpy little thongs. I imagine myself wearing each one in turn, imagine how they would feel against my skin. Then in the corner of the drawer, I saw them. That pair. The racy led panties I'd once caught a half second glimpse of from behind. That mental image that I'd stored, relived as I lay alone in my bed, jerking myself, night after night. I gasped in glee. It had to be these ones. Nothing else would do. I held them up in the air, admiring how the light ran through all the gaps in the laces and bows. I felt so excited, so completely thrilled, so ALIVE at that moment, that I didn't hear the drunken voices outside the front door.

Suddenly the sound of the key in the door. Total panic. It must be Sophie, she must have gone to the pub. I sprint out her room, stuffing the lacy little red panties in my pocket as I go, desperately scrambling towards my own bedroom. The sound of keys still jangling in the door -- drunken fingers struggling to turn and open. Thank god for happy hour. I turn the corner and fling myself into my room, pulling the door behind me just before Sophie and Idiot Rugby Boy finally collapse into the flat, all boozy giggles and noise and kissing and pawing.

I hear them beeline straight for Sophie's room. They never make an effort to be quiet when they've been drinking. Oh god, I don't now much more craziness I can take today.

I try to ignore the sounds coming from next door to concentrate on the homework given to me by the boss. Steal the panties, check. Now I had to put them on, and cum while wearing them. Eep. Here we go.

I strip down, until I'm looking at my naked shape in the mirror. I'd always been small and slim, but I'd never thought of my figure as girlish. But after the events of the day, I looked at myself in a completely new light. I raised my heels, tilted my head, dropped my hip, and all the other things I half remembered I'd seen girls do to make them seem more feminine. It was a strange and new feeling. But somehow, it was also a familiar one.

I turned my head to look at the red panties, which I'd left lying on my bed. Now or never. Sitting on the bed, I held them lightly between my fingers, before pulling them open and pushing my feet though the gaps.

Now I was on the small and slight side for a guy. But Sophie was about 5'2, and maybe three stone lighter than me. The lacy panties groaned and protested as I tried to lift them up my thigh, and onto my waist. I could feel them stretching hard as I pulled them over my hips. Please don't break, please don't break. But somehow they stay intact, even with my little cock pushing against the lacy bow of the front.

I lie back on the bad, looking down at my body, at my cock encased in the frilly red underwear. And as I do, the noises next door get louder. I've heard them so many times before. Sophie is about to get fucked, and whether I like it or not, I'm going to hear.

"Beg for it", the braying voice of Idiot Rugby Boy demands.

"Please fuck me. Please put your big cock in my pussy and fuck me Hugo".

Hugo. People like Sophie's boyfriends are always called Hugo.

"Please fuck me Hugo. Please fuck me" Sophie implored in her rasping Marlboro Light posh-girl tones. "I need you to fuck me hard. Fuck me like a whore".

My cock twitches hard against the red panties. The unmistakable thump-thump-thump sounds of Sophie's headboard begins. I stroke myself in time with the rhythm of the thrusts, of Sophie's moans. My little cock is now rock hard and attention, my hand rattling up and down. I imagine being in the room, watching them, being them.

"I'm cumming you slut. I'm cumming right inside you" Hugo breathlessly stammered. "Please cum in me. Cum inside me." Sophie begged, seemingly climaxing herself.

A sudden extra large thump, and a loud moan. As Hugo and Sophie both collapse in each other's clammy arms, I came myself, a great jet firing up and out of the top of the panties and up my stomach and chest. As I lay on my back gathering my breath, I realised that while listening and stroking I had -- quite without realising -- lifted my knees and feet up high, like a girl lying on her back getting fucked. I imagined Sophie in the bed next door in the same pose.

I sat up and turn once again to the mirror. My naked, boyish body, in a pair of lacy red panties. Cum all over my stomach. I've never been able to explain how I felt in that moment. The day the entire trajectory of my life changed forever.

Walking to the town centre the next morning, I realised I was a bag of nerves. I was in public in a pair of lacy red girls panties. Hidden under suit trousers admittedly. But I knew. This was, by a million miles, the most outrageous thing I'd ever done. Well, not counting what I did yesterday of course. THAT was crazy. But still. I looked at each person I passed on my walk, wondering how they might react if they knew. The old lady at the bus stop. The big lads in hi-vis jackets on the building site. The mum's on the school run. Would they laugh at me, would they want to beat me up? Would they find it hot too? I played my silly make believe game all the way to my second day at the office.

The boss and the two admin ladies were already there when I arrived. This little satellite workplace with just three employees and me felt somehow even smaller than yesterday, like the walls had closed in overnight. I became very conscious of how little personal space we all had here. The ladies tapped away mindlessly without every looking up. The boss meanwhile was just looking at me, just looking slowly and intensely, up and down. Leaning against the doorway of his private office, he ran his eyes up and down my body. I stared back, our shared knowledge of what had happened yesterday evening felt like it was physically pulling us towards each other.

The two Admin Dronebots kept tapping away on their keyboards, their backs to the boss and me. As I lifted my arms up to hang my coat on the hook by the door, my shirt rode up my body, giving him a glimpse of my secret. Sophie's lacy red panties poked over the belt line of my trousers. The boss smiled at me, and silently mouthed across the room.

"Good girl".

The morning was a blur. I could barely concentrate on my extremely monotonous temp job -- organising files, scanning them in, entering the details onto a database. Dull dull dull. But so mindnumbingly simple, that any idiot could do it. Well on that day, I couldn't. My mind raced through all the possibilities of what the day would involve. He'd probably have me suck him again. That idea, so alien and ridiculous to me just twenty four hours ago, now filled me with excitement. I wanted to do a good job of it. I wanted to please this man. I wanted him to tell me I was a good girl again. I wanted to be the slut, the whore, the sissy that he wanted. I would do whatever he said.

Hours passed, the afternoon came. Just like the day before, The Boss tapped me on the shoulder as the Dronebots got up to leave just before 5pm, asking me if I'd be interested in doing an hour of overtime. Yes sir, absolutely. The women left, leaving the door two of us alone in his office.

I stood awkwardly by the doorway, while the boss lazed back in his chair, looking me up and down. In that moment I imagined this is what girls in pubs felt like, treated like an object by the men around them. Excited by that thought, my little cock twitched against the lace of the silky underwear, for about the hundredth time that day.

"Well let's see them then". His tone is calm, friendly. But also firm, serious.

Nervously I lifted up my shirt, higher this time, showing off the full waistband. Unsure what else to do, I sort of twirled slowly, awkwardly. I think I was trying to be sexy, to be coquettish. But with no idea how, I just sort of rotated. A rotisserie chicken in knickers. The boss let out a chuckle.

"I've already had the peak. I want to see the whole thing. Take off your trousers."

A wave of panic. I hadn't expected this. I figured I'd be on my knees sucking him like yesterday, but I thought he was only interested in the idea of me in panties. But no, he wanted to see it all.

He sensed my hesitation. He rose to his feet, leaning over me. His tone hardened, but his voice was still quiet, measured.

"I'm not asking. I'm telling. Now take off. Your. Fucking. Trousers."

"Yes sir, I'm sorry".

First kicking off my shoes, I hurriedly unzipped my suit trousers, and let them fall to the floor. I stepped out of them, now in front of this man, my bottom half naked except for the frilly underwear hugging round my cock. He looked up and down my slim but toned legs.

"Not bad. They'd look nicer shaved though. We'll deal with that for next time".

He wants me to shave my legs now? Oh god, what have I gotten into? I won't be able to hide that from the guys in the showers after training. God I hope he's joking, I hope he won't make me do that.

The idea that I could simply say no didn't occur to me for a second.

"Let's see the back".

I turned round, showing him my firm little bottom and the back of my thighs a calves. Instinctively, I raised one of my feet onto tip-toes, raising my calf, dropping the opposite hip, feminising my outline. I looked over my shoulder at him, and gave what I think was a very ham fisted attempt at a coquettish smile, my nervousness obvious despite my attempts to conceal it.

"Come over here". He gestured towards to the little two-man sofa stuffed into the corner of his personal office. Then he sat down in the middle of it, his legs splayed wide. I walked over slowly until I was stood in front of him, my bare legs giving away the tiniest hint of a tremble.

"Kneel".

I dropped to my knees fast. Too fast -- too eager. "Someone's a little desperate for some cock I see" he chuckled. "What a naughty little slut you are".

He was right, and I was no longer interested in pretending otherwise. I fiddled excitedly with the button of his suit trousers. I realised my mouth was watering. Finally I got the zip down and out sprung his thick seven inch cock. As it bounced up towards my lips, I opened my mouth in anticipation, and began lean forward to take him inside. Yesterday I'd frozen, and had to be physically pulled in. Today was different. Today I was different.

"Slow at first" I thought. Tease him a little. "Remember what girls do in porn. Do what you would like."

Rather than take him straight into my mouth, I hung out the tip of my tongue, and ran the tip in little swirling circles around the top of his already brick-hard cock.

"Mmmmmm, good girl". There was that purr again, like yesterday. I was pleasing him. I was being a good girl.

I swirled some more, now not just on the tip, but in little circles round the underside of his cock-head, my lips moving down to gently rest against the tip, a delicate kiss. Then slowly, slowly, plunging my head down the length of his cock, my lips tightly sealed around his shaft, the flat of my wet tongue gliding down his length as I dropped lower, lower. My god he was right, I was a little slut. There was no denying it now. Yesterday I'd been so shocked, so thrown, so nervous. He'd done most of the running, but today I was going to set the pace, I was going to be his little nymphette, show him what a confident little cocksucker I was. A part of me that had always been there, was awake for the first time. I was going to show him that I can control things and satisfy him. I plunged deeper still, taking his full length into my mouth. I pushed him right into the back of my throat, partially blocking my air, pressing towards my tonsils. His hairy, sagging balls pushed against my chin. My nose buried deep into his pubic hair, deeply inhaling that sweet, sweaty, perfume. Holding for a few seconds with my eyes closed, I tried to savour every part of the sensory overload, before readying myself to slowly slide back up his shaft.

But the boss had other ideas. A hand cupped the back of my neck, holding firm, pushing down, further down. But there was no further down to go, no more space inside me for his hard dick to fill.

The reaction was immediate, coughing and spluttering as the head of his dick thrusted firmly into my throat. I felt like I was going to cry, and suffocate, and throw up, all at the same time. This was not what I expected. Yesterday he'd finished aggressively, but at the beginning he'd been gentle. Today was different. Apparently today we were both different.

"Hold it in" came his voice. That calm firmness again. "Take it all in. Don't you dare come up".

I struggled to regain my composure. After a few seconds I managed to get my breathing going again, big heavy snorts of air just about finding their way round the pulsing cock filling my throat, down into my lungs. Unbidden tears streamed down my cheeks. I involuntarily gagged a couple more times, but eventually that subsided. I'd calmed myself. I'd got it together. For about ten seconds, neither of us moved a muscle. Then, finally satisfied I'd got my body under control, he spoke.

"Now keep your throat open for me slut"

I didn't know what that would even mean. But that didn't matter. I wasn't in control. The boss was. Whatever happened next would not be done by me, but to me.

One hand behind my head became two. Each heavy, leathery palm pushed firmly against my ears, the base of his thumbs anchoring against the lobes, his hairy fingers curled round the back of my skull. Holding my head, positioning it, lining up the angles.

Then suddenly, air. My head was lifted off his cock, sliding back up until the head was once again between my lips. I desperately scrambled an unobstructive breath into my lungs, knowing full well what was coming next. Thump, down my head again into his crotch, his firm grip accelerating me down. None of my back and neck muscles were doing any work now, all the movement was coming from him. He was fucking my face, and my only job was to keep my mouth open and let it happen. I had misunderstood everything. I wasn't hear to pleasure him. I was here to let myself be used for his pleasure. I wasn't the protagonist. I was just an object.

My cock pushed desperately against the red lace panties. This realisation had made me rock hard.

On this went for several minutes, up down and up down, thump thump thump. My head being moved up and down against his lap, my throat being violated over and over again. I concentrated on staying calm, keeping everything open for him, trying not to gag or splutter. Until finally it stopped, as with one particularly heavy thump, he pulled my head down onto him and held me there, my whole face pushed deep into the pudgy flesh of his groin.

He must have cum. I couldn't taste or feel cum in my mouth, not like yesterday. But then maybe he'd thrust so deep he'd actually bypassed my tastebuds entirely, and shot straight down my throat. Would I even be able to tell if he'd done that? My lack of experience meant I had no idea what any of this would even feel like.

"Good girl, good girl" he whispered, his raised pulse giving causing him to pant slightly as he spoke, "Don't move, keep it in there".

I, of course, obeyed. It was clear now that I would always obey. I was a good girl.

And then, for the second time, something completely I hadn't expected happened. He's leaning forward, stretching his arm over me, his hand down my back, my head still held firmly against his crotch. Now the tip of an index finger, pushing against the back of the red lace, gently sliding down the crack of my arse, stroking, pushing, probing. Then stopping at my hole, gently running little circles through the fabric of the underwear, clockwise, counterclockwise. Now over the initial shock of feeling his finger playing with the outside of my hole, I relaxed enough to realise something. This feeling was bliss. Nobody had every touched me down there. No girl would do that -- at least none of the girls I'd been with would. Even in those dark fumblings with the boy from my class back at home, we'd only ever touched each other at the front. This was new, and every circle, every swirl, sent electric pulses of pure joy up through my body, up to my brain and down to the tip of every finger and toe. This was a pleasure I'd never experienced before, completely unlike the feeling of someone touching my cock, a lovely but very much localised feeling. This felt like somehow his fingertip was swirling every single inch of my body, inside and out.

"Come up onto the couch".

His hand released me from it's seal around his dick. Up I came, doing my best to disguise the huge gasp for air I took once free. I needn't have bothered, he liked to hear the sound of my struggle.

I stood, and turned to sit next to him. I'd lowered myself half way down when suddenly

"No. Not like that. Put your head here". He motioned to the opposite arm of the couch. Not sure what he meant, I leaned laterally, placing my head sideways on the arm rest, looking as if I was about to settle in to an evening in front of the TV.

"No!". That tone from yesterday is back. He's angry with me now, impatient.

"On all fours slut". His left hand forcibly hoiks my knees round, while his other lifts me by the hips, then pushes my face down into the cheap nylon fabrics of the couch's armrest. I'm struck by how easy that was for him, how surprisingly strong he is for a man of his age. I'm now positioned across the length of the couch, my head hanging off the side, my knees and feet pushed towards him, my underwear covered bum rising high in the air. I'd fucked girls who'd been in this position before, but now it was me on my knees and elbows.

His fingers inside the waistband of the red panties, slowly pulling them down until they're half way down my thighs. Propped, primed, on display. I hear a "click" behind me, something plastic being opened. Before I can even process the sound, I feel the cool splash of some kind of liquid between my cheeks. His index finger runs up and down, a frictionless glide, before once again settling on my hole, swirling round. Again, bliss, I am once again lost in those waves of pleasure and joy.

Then it happens.

With no warning, his jagged index finger lurched firmly into the heart of my opening, and pushed its way inside. I made a noise I don't think I'd ever made before, somewhere between a yelp, a gasp, and a moan. The gentle, tingly sensations were now being drowned by a sharp pain, a muscle being contrived into a shape it had never been before. Without any conscious input, my body snapped into action, my sphincter hugging tightly around him as if I was squeezing his finger inside a fist. He'd probably only got about an inch of finger inside me before I'd tensed in alarm.

"Relax, relax". The anger had gone, but I could still here the impatience. He held his finger still inside me, my anal muscles spasming and gripping for all their worth.

"Just relax".

I tried to breath, to calm myself. I focused every fibre of my mind and body onto getting my hole to relax, to welcome in this uninvited guest. Picturing yoga, thai chi, anything. After about thirty seconds, I finally -- sort of -- managed it, the death grip on his finger beginning to soften.

"Good girl".

I'm a good girl. I'm pleasing him.

"With my body now softening against him, the boss began to gently push his index finger in and out, in and out, each entry going a little deeper. Now an entirely new sensation, probably the deepest, most intense one I'd ever experienced. In my youthful ignorance, I didn't know what a prostate was, never mind what touching it might feel like. Now, I knew. As he slowly fingered my tight little virgin hole, this glorious swell gradually grew inside. Like a ball of warm energy, starting small, growing slightly bigger which each gentle push of the finger. I had been wrong -- the boss wasn't just in it for himself, he wanted to pleasure me too. In my near delirium, I hadn't notice that I was letting out a feminine little moan, a little "ooo" with each thrust.

Then suddenly, his finger left. As it did, I felt what I can only describe as a feeling loss, my back passage grieving over suddenly how empty it now felt. I know that sounds ridiculous, so hyperbolic. But how I longed to be filled up by his finger again, how despite never having experienced that in the twenty years of my life up to that point, that it felt like how things were meant to be.

"Please put it back in" I meekly yelped, the words leaving my mouth before I'd even thought them. I was now someone who begged to be penetrated. What was happening to me?

"What a little slut you are", the boss purred. "Don't worry, I've got something even better for you".

I felt the pushing against my hole again. But not a finger this time. I lifted my head, trying to turn round and see, not that I didn't know what was happening. As soon as I did, he reach across with his big right hand, pushing my face back down into the fabric of the armrest.

"Stay down there whore" he barked.

He hadn't cum in my throat. He wasn't focusing on my pleasure. He was just getting me ready for himself. He was going to fuck my virgin little hole. And I was going to let him.

This time no teasing, no swirling, 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 like the top of my skull was going to come clean off my head. I'd never felt a feeling like it, an explosion deep in my pelvis. Pain and shock, but also undeniably, pleasure. But a pleasure so intense it frightened me, a pleasure I couldn't control or contain.

With a firm hang on each of my hips, he began to fuck my hole. My muscles were loose from the finger, but his cock was big, so my sphincter screamed at me in protest, a sharp sting of stretching too far, too fast. 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 the warm ball filled my entire body. I'd never experienced anything like this. Regular sex with a girl made my dick feel nice. This made my whole body sing, every synapse and nerve-ending joined together in a chorus so powerful, so all consuming, it was all I could do not to cry. All restraint, all decorum had now been completely driven out of me, and I was loudly moaning like a whore with each deep thrust of his cock. My little arse in the air, my face buried down low into the couch, letting this man fuck me while I wailed in pleasure. There could be no denying who I was ever again.

"You want me to cum sissy? You want me to cum in your little sissy fuckhole" the boss spat out, that meanness and aggression from yesterday was back. I tried to say yes, but every time I opened my mouth to speak, all that came out were more moans. Instead, I nodded my head furiously, while my body bounced back in forward, a rag doll on his cock.

"Beg for it. Beg for my cum". An order, not a request.

"pp..... leeeeese cum..... in..... me.... sir. pleeee............. se". I just about managed to get the syllables out between moans and gasps.

"yes. YES! You filthy fucking sissy whoooooooore....".

With the final word, he gripped my hips so tightly his fingernails broke the skin, and he thrust with a force so great I felt like I would be broken in half. I wailed, the primal, irrational noise of a wild animal. I was in bits. He made a few slower thrusts, milking every drop of cum out of him and into my passage. He was going to pull out when he was ready, not before. A minute or so passed of him gently rocking back and forth, savouring every last orgasmic twitch.

"What a filthy little sissy you are. I bet none of your friends know what a slut you are" he finally chuckled.

I opened my mouth to answer, but as I did, he abruptly pulled himself out of me, and seemingly every drop of air left my body in another primal, guttural moan. What could I possibly say anyway? He was right. I'd had sex with girls before, but nothing could compare with this. It wasn't just that it had felt so incredible, sensations more intensely amazing that anything that had happened in my two decades on this planet. It was more than that. I had been dominated and objectified. I had been physically manhandled, taken advantage of, used as a fucktoy. He had never touched my cock at any point, and had seemingly no interest in what I might want. I was his sissy, his slut, his whore. And the horrifying truth, one that I could no longer hide from, was that I loved it. No, more than that. I needed it. I wanted to please him, to excite him, to obey his orders. Whenever he called me "good girl", it didn't just turn me on (although my god it absolutely did). It made me feel right. It made me feel home.

Suddenly he's talking.

"I won't be in for a couple of days. Meeting in London. Janet and Sally will show you what files need sorting" he said.

Files. You're talking to me about files. We are seriously talking about filing? Thirty six hours ago I was a bored and lazy straight-boy student. Now I'm on all fours in my flatmate's panties, in the office of a fifty five year old man who's just fucked me within an inch of my life. And who is now talking to me about fucking files?

And what's this about not being here for two days. Two days! I realised how disappointed that made me feel, how addicted to his cock, to being his personal sissy fucktoy I'd become.

"... but I'll be back on Friday. Everyone else is at some corporate away day. Team building exercises and bad sandwiches. All that nonsense, stupid stuff. I told them I was far too busy. It'll just be you and me all day."

My breathing stops.

"I've got something special planned for you. It's time we made a real girl out of you."

Something special. A real girl out of me. I had no idea what any of that meant. But I didn't care. I was floating, Whatever Friday held in store, I wanted it with every inch of my being.

"You can go now".

Same as yesterday. He's used me to cum, so now I can go.

I pull Sophie's red panties back up my thighs, now dewey with sweat, his and mine mixed together. Pull them back over my cheeks, with the lube still smeared round my hole. Pull them back over my cock, the tip soaked with pre-cum. Then off in search of my trousers, while he admires once again the shape of my firm little arse, framed by the red lace, while he zips himself back up, adjusts his tie, smooths his hair back into it's sensible side parting. I finish getting dressed and turn to leave.

"Haven't you forgotten to say something?" I hear over my shoulder as my hand stretches to open the door. I turn, silent, not sure what he means. What else is there to say?

Seeing my confusion, he stands, and walks slowly towards me. Confident, unrushed. This is his house, this is his time. Just like yesterday, he stops so close to me we are almost lip to lip.

"You need to say thank you sissy". Calm, playful. But firm.

"Thank you sir."

"Thank you for what?"

I sense what he wants to hear. "Thank you for letting me suck your cock. Thank you for fucking me and cumming inside me. I hope I pleased you sir".

He smiled. The big, wide, satisfied smile of a man who knows he now owns me entirely, that there is nothing I won't do. I'm his. He pauses for what seems like an age before finally, he says it, the words I long to hear.

"Good girl."