The Boss

I am making a collection of photographs – call it an art project – of the guests’ belongings. I think it will make an intriguing exhibition when it is finished. All the detritus of life is in it: the pill bottles, the discarded novels, the ripped stockings, the binned pregnancy tests, the dying anniversary flowers. Once, a gun. Another time, a crack pipe and a wad of money. But most of what I photograph is sexual. Vibrators, used underwear, handcuffs. He looks like a handcuffs man.

I opted for the room on the right, which appeared to be hers. It had all the typical feminine fixings. An evening dress hung on the outside of the wardrobe. Perfumes and lotions on the dresser. I opened the drawer, hoping for something shocking, but found only some electric chargers and a Gideon bible. Her underwear yielded no latex or leather, not even anything cheekily crotchless.

Perhaps I was wrong and they were simply a boss and a secretary spending a post-conference night here.

Footsteps on the landing threw me into panic. Had they changed their minds about the tea? I considered hiding in the wardrobe, but seconds later realised that they were both going into the room nextdoor.

His was the voice I heard first. ‘I’ve told you about this before,’ he said. ‘You do not give orders. You leave the ordering to me.’

‘But you were in the lobby, seeing about your newspaper. And they came to take the order. And I knew what you wanted.’

‘None of that alters anything, Mara. You have broken a rule. And you know what happens when you break a rule, don’t you?’

‘Yes, Sir,’ she said with a resigned sigh.

Mara might have known what happened when she broke a rule, but I didn’t, and I very much wanted to. I tiptoed to the connecting door, knelt down and put my eye to the keyhole.

He stood by the bed with his arms folded while she – Mara – was rummaging in a dresser drawer. She had her back to me and, as she bent to retrieve whatever it was, her bottom was thrust out, tautening her skirt to maximum stretch. He was looking at it too, the dirty bastard, getting a good long eyeful.

She straightened up again, turned and handed him something. It was a leather strap, about half an inch thick, with a grip for the hand at one end.

I took a deep breath. I was in for a treat.

When he took the strap, he slapped it into his palm, as if testing its painfulness, then he nodded.

‘You know what comes next,’ he prompted, and the lovely Mara dropped on her knees in front of him, head bowed.

‘Please, Sir, I’m sorry I broke a rule and I beg to be punished for it.’

‘I’m considering it.’

‘Please, Sir. I really need it. Please punish me.’

‘How hard?’

‘As hard as you think I deserve.’

‘Good.’

He was good. Very good. Making her beg for it – nice touch. I’d have to add it to my repertoire.

She bent to kiss his shiny shoes, her silky hair falling over her cheek. I pictured her bending like that to lick my clit, all so sweetly submissive and obedient. I raised my skirt to my waist and put my fingers down my knickers. Damn this stupid country-house hotel and its inconvenient uniform.

‘We’ll start with my hand,’ he said, seating himself in the armless straight-backed chair by the bureau. ‘Remove your skirt and place yourself over my knee.’

I watched her unzip, my mouth watering as I wondered which view of her I would have. Perhaps her face, suffering and contorting in pain. Or perhaps her bottom. I rather hoped for the latter.

Her tight skirt had been tugged down over the swell of her hips before I glimpsed her milky thighs, with their suspender straps interrupting the smooth expanse of skin. She stepped out of it and laid herself gracefully over his lap. Joy of joys, I had the most perfect view of her upthrust bum, the flesh spilling from her silky shorts.

Not that the silky shorts lasted long, for he peeled them down until her bottom was bare and they rested just above her lace stocking tops. Now her arse was cunningly framed by the suspender belt and straps, with the froth of silk and lace three-quarters of the way down her thighs.

She was ready to begin. And so was I. My finger was on the button. Three, two, one …

But he wanted to lecture her first, it seemed, while his hand moved idly round and round her vulnerable cheeks. He spoke about mindfulness of rules, respect, discipline and duty. She chimed in only to say ‘Yes, Sir’ and ‘No, Sir’ but he seemed satisfied with this.

His palm flattened against her buttocks, which tensed immediately. I imagined her teeth and fists clenched in concert.

‘Now this is just to start us off,’ he warned her, starting in with quick, sharp smacks across the centre of her quivering bum. He did not seem to be putting a great deal of effort into it, lifting his arm only to chest height before swooping his hand down to meet her flesh, but the sound was music to my ears, as were Mara’s wails and complaints.

‘Oh! Ouch! Ouch! It hurts!’

‘Don’t be silly, Mara, this is a gentle warm-up. I haven’t even started.’

A long, despairing moan met this statement, but I could see that the boss was warming to his work now, laying on harder and harder strokes, at times leaving handprints. It was strangely aesthetically pleasing to watch Mara’s bum jiggling around and changing to a deep-pink colour under her employer’s chastising hand and I watched transfixed, hoping that he would carry on for a very long time. Much as Mara disliked the slow, hard strokes, she seemed to hate the sudden volleys of speedy ones even more, for these made her wriggle and twist like fury, calling out for him to please, stop, please, it was too much, she would be good, oh, she would. But he was utterly resolute and no amount of gasping, pleading or tearful contrition would deflect him from his purpose. Only when Mara’s poor bottom was fully and blazingly reddened and her kicking legs limp and spent did he begin to stay his hand.

For my part, my hand was hard at work, stuffed eagerly inside my cotton boyshorts, and I knelt with my fingers stroking the wiry curls of my muff and my longing clit, excited beyond expectation at Mara’s humiliation.

Oh, why did it have to end? I silently protested. Mara’s bottom had taken ten long minutes of this summary treatment, but I wanted to see more.

I uttered mute thanks to an unnamed deity when the boss, helping his subdued secretary to her feet, instructed her to go and bend over the side of the bed with her bottom high and her feet apart. This was not the end!

My joy was not matched by Mara, whose lower lip stuck out a mile.

I wondered about this dynamic. Surely it must be consensual. They would have a safeword, presumably. He seemed highly experienced, at least, and they had clearly developed their own rituals.

‘Mara, a spanking by my hand is the least you can expect for petty rulebreaking. Breaking one of the golden rules of obedience merits the application of something a little more forceful. If you are to learn, I must be strict and consistent with you. Do you understand?’

‘I am too sore,’ she snuffled.

‘Do you understand, or shall I be harder on you than I originally intended? There will be extra strokes for defiance.’

Mara let out a great howl of anguish, but she went to the bed and obediently bent herself over the side, grasping the frame. Her sore bottom glowed like a beacon amid the pale-pink frilliness that framed it. I sucked in a breath on her behalf, then another when Mara parted her feet, as instructed. All at once, that gorgeous little slut’s most secret and intimate parts were visible, tender pink lips spread and vulnerable. To me they looked edible and I imagined my teeth nipping and tongue licking at the tempting array.

But it seemed that Mara could not expect anything so pleasurable, as the boss had picked up that wicked-looking brown leather strap and stood testing it for bend and snappiness.

‘Do you ever go anywhere without those nasty things?’ blurted Mara, fearfully watching him stroke the supple hide then bend and flex it against his palm before slapping it gently down.

He looked over at her, strap in hand, without answering.

‘You will count,’ he said briskly, crossing to stand at her rear. ‘I plan to apply twenty strokes, but I will give extra for broken position or disobedience of any kind. Now then.’

He swung the strap through the air a few times before allowing it to whistle down and snap across Mara’s backside, causing her to sing out in pain and rock on her heels until she could count out a shaky ‘One, Sir’.

I noted the wide red stripe left to burn across Mara’s bottom and watched agog as the rest were delivered, slowly and with decorum, sometimes leaving a little pause for Mara to recollect herself, falling across the full width of her bum and down to the upper thighs, which appeared especially painful. I fidgeted furiously with my needful bud while I watched Mara lift her feet, clutch the bed frame and yelp into the mattress, as her bottom received stripe after stripe. The air around me smoked and snapped with the sounds and scents of punishment and arousal; the shocking crack of the strap urged my fingers on to the completion of the quest.

Mara earned herself two extra strokes by jumping up straight and rubbing her bottom furiously, and, by the time the twenty-second was applied and counted, I had found my moment of sweet release, biting my lip as she doubled over on the floor, intent on allowing no sound to betray me.

I shuffled back to my knees for a final glimpse of Mara’s crimson bum with its pattern of long rectangles. The girl was panting and mewling, still bent over, while bossman was issuing some words of wisdom or other which went over my head, so transfixed was I by the obvious changes that had been wrought to Mara’s cunt. Now it was deeper in colour, swollen and glistening slightly with what must surely be her female juices. It certainly seemed that Mara had taken some pleasure from the pain. It wasn’t my bag – I used to think it was some myth made up to suit the purpose of cruelly inclined men. But I had seen enough juicy little pain sluts over the years, and here was Mara, almost dripping …

I watched the errant secretary slowly uncurl her spine and stand, head bowed and bum burning, before her master.

He bent and whispered something into her ear. She grimaced and turned towards me and – oh, shit! – she was coming straight towards the door.

I didn’t have time to stand straight, still less back away, before the handle turned. It was unlocked. I hadn’t thought it would be unlocked. In my haste to scramble out of view, somewhere, anywhere, I fell backwards.

When the door opened, my fingers were still struggling to escape my knickers and my skirt was hiked around my waist.

Mara’s hands flew to her mouth and she aimed a desperate look at her boss. So did I.

What the hell was going to happen now?

I retrieved my juice-stained fingers and tried to stand, blabbing out incoherent apologies. At least, they might have been apologies, or I might have just repeated ‘Oh, God’over and over.

The boss, surprisingly unruffled, simply folded his arms and watched me. ‘What have we here?’ he said. Then he crooked a finger.

‘Please don’t report me,’ I whispered, finally managing to arrange my legs and my skirt so as to allow me to get up.

He shook his head and shushed me.

I walked past the curious Mara and presented myself to the boss. I couldn’t look at him, focusing instead on my fingers, which gripped each other so tightly they whitened around the knuckles.

‘Who are you?’

‘A chambermaid. Sir.’

‘No, I mean what’s your name?’

‘Kim, Sir.’

‘And what were you doing, crouched down there by the door?’

‘I was … polishing the handle, Sir.’

Even as I said the words, I knew lying was a bad idea, but I felt I had to make the token gesture, or he’d think I was some kind of pushover.

‘Polishing the handle? Look at me.’

I twisted my neck to the side, but he repeated the instruction and I lifted my eyes with much reluctance to his.

‘Do you often polish things with your hands down your knickers, Kim?’

I could do nothing but shrug.

‘You were watching us, weren’t you?’

‘I couldn’t help but notice …’

‘No, I’m sure,’ he said dryly. ‘And what did you notice?’

‘You spanked her. Your secretary. And you used a belt. Strap. Thing.’

‘That’s right. So you saw everything, from start to finish?’

I nodded.

At this point, he looked away from me, towards Mara. ‘I thought I sent you to fetch something, didn’t I?’

Her mouth fell open and I thought she was going to protest, but she decided against it and headed into the other bedroom, her red bottom swaying from side to side.

‘And what did you think of what you saw?’ He spoke to me again, his voice lower this time.

‘It was very interesting, Sir. I’m so sorry!’ I burst out again.

‘Don’t apologise. Clearly, you found it quite stimulating. Didn’t you?’

‘Yes, Sir.’

‘Did you come?’

I sucked in a quick breath. What a question.

‘Yes,’ I whispered.

‘I see. So you like spanking?’

‘Not really. It wasn’t that, so much as … watching her getting spanked. She’s very pretty, Sir.’

‘You like her?’

I nodded again.

‘You’re gay?’

‘Yes.’

‘Well, this is interesting.’

He was silent for a moment, his hand at his chin.

‘Are you going to report me?’

‘No. No, I don’t think so.’

‘Oh, thank you,’ I blurted. ‘Thank you so much. And I really am sorry …’

‘I haven’t finished yet. Listen. You like Mara. How would you like to help me complete her punishment?’

I looked wildly back into the other bedroom. Mara was on the threshold, holding something in her hands. I couldn’t quite make out what it was.

‘Oh … is that … I mean, would that be OK?’

Her blushing face was bowed. She still wore a silky blouse on her top half, while her bottom half consisted only of stockings, suspenders and lowered knickers. Her little pink triangle was shaved bare, her pussy lips peeking out at me.

‘Mara,’ said the boss. ‘Kim here would like to join us. I trust you will be a good girl for her. Won’t you?’

‘Yes, Sir,’ she said.

‘If she wants to,’ I said, turning to the boss, suddenly firm. ‘Only if she wants to.’

‘She wants to,’ he said.

‘I need to hear it from her.’

‘Fair enough.Mara?’

She raised her head and nodded shyly at me. Her blush was gorgeous. I wanted to kiss her lips and stroke her hair, especially when she gave me the tiniest little smile, a secret between us.

‘Thank you, ma’am,’ she said.

‘Now,’ said the boss, ‘bring me the plug and then undress yourself, for Kim to watch.’

Mara handed over the item, which I saw was a butt plug, quite a wide model, not for beginners. Then she came to stand opposite me, so close I could touch her, but I wasn’t sure it was allowed, so I held off.

She unbuttoned her shirt and slipped it off, then took off her bra to reveal beautiful full, plump breasts with round red nipples.

‘Touch them, Kim,’ invited the boss. ‘Feel how heavy they are.’

They were rather heavy, not the weightiest I’d ever held, but certainly filling my palms satisfyingly. I let them jiggle in my hands, then I squeezed them, then I stroked the nipples with my thumbs and was rewarded with a pretty little shimmy of her hips.

‘She has very sensitive nipples,’ he remarked. ‘The lightest of clamps is all she needs. But I’m not going to clamp them today. She’s had her quota of pain. Feel how hot her bottom is.’

I slid my hand around her hip, on to the luscious curve of her arse. Oh, he was right. The heat was lovely, like warming my hands on a radiator. I loved the effect the strap had made, ridging her skin so I felt little ripples of sensation when I stroked it.

‘Best of all,’ said the boss, more softly now, ‘is the effect a good thrashing has on her pussy. Touch it. You’ll see.’

I looked up at her face, as if seeking permission, but her eyes were closed in a kind of rapture. She was somewhere deep inside herself but, wherever she was, it was exactly where she wanted to be.

I parted her thighs a little wider and dipped two fingers between her pussy lips. So hot and juicy, and her clit was swollen right up. I massaged it slowly, enjoying the way her thighs trembled against my hand.

‘You’re right,’ I said to the boss. ‘She’s soaking wet.’

I pushed my fingers into her cunt, digging inside, feeling her tightness, while I kept my thumb on her clit.

‘Hmm, careful there, Kim, you’ll make her come. She’s not to come yet.’ He changed the subject brightly. ‘Have you any experience with butt plugs?’

‘A little,’ I said. ‘Not much.’

‘But some? Oh, I’m sure you’ll do a good job.’

He sat down on the edge of the bed and unbuttoned his trousers. ‘Over here, Mara, on your knees.’

She knelt between his legs, waiting obediently while he removed his erect cock from his underpants.

‘She’s going to suck my cock while you put the plug in,’ said the boss. ‘Lubricant is in the right-hand drawer. Let me know when it’s fully inserted.’

I blinked, a little nonplussed at the turn of events, but I retrieved the bottle of lube and went to sit on my heels behind Mara, who by now had a good mouthful of the boss’s rather large cock.

I parted her buttocks, seeking the tiny round hole I had the task of filling. Her cheeks were hot and obviously still sore, and her little rosebud quivered when I pressed my thumb against it. She was obviously well trained, though, because she kept her bum thrust out and didn’t try to clench or wriggle away from me.

I uncapped the lube and spread plenty on my fingertips, then I pushed them against the rosette, circling it delicately, getting closer and closer to the target. I felt a tiny pressure of resistance, then my forefinger eased inside. How tight she was. I thought she might suck my finger inside and hold it there, but I was able to pull it back with little trouble.

I applied a good squirt of lube to the plug and went to work on that next. I pushed it slowly and gently, rotating it until it began to slip in. As I pressed, then stopped, then pressed some more, she made scoffing noises, her mouth too stuffed to express her real reaction.

The boss was holding her by her hair, keeping her head low down. I wondered if she was deep-throating him. He looked pretty happy, at any event.

‘How … is it going?’ he rasped.

‘Nearly halfway in,’ I reported. ‘Just getting to that nice wide part.’

‘Keep that held there for as long as you can before you push in the rest,’ commanded the boss. ‘Make her feel it. Make sure she really feels how full and stretched she is.’

‘You’re the boss,’ I said. ‘Now, keep still, Mara, and be a good girl. You’re going to have a sore bum, but you won’t mind, will you? Because it’s what you deserve.’

I loved her little gasps of shock and amazement as I held the plug at the cruellest part. The boss shoved down hard on her head, fucking her mouth. She writhed at the hips and I took pity on her and pushed it all the way in, so that the flange sat between her cheeks, showing anyone who looked that her rear hole was occupied. How decadent it looked, with her striped scarlet bum cheeks on either side.

I wanted to touch myself again, but I knew better things were coming, so I held off.

‘Good,’ said the boss. ‘Off, Mara.’

He let go of her hair and released her mouth from his thrusting cock.

‘Now then, Kim, it’s up to you what you want to do with your clothes, but you need to lie down on the bed with your legs spread and your cunt available for Mara to lick. I’ll give you a moment …’

It barely took a moment. I threw myself eagerly on to the bed, pulled up my skirt, yanked off my knickers, layingmyself bare for Mara’s tongue.

Soon enough it was there, planted between my lips, while she breathed and stroked and licked like an expert, kissing my clit and pushing her fingers inside my cunt with such absorption that you would never realise she was getting fucked from behind all the while. Her face lay buried in the junction of my legs, building my arousal higher and higher, while the boss, still almost fully clothed, rose behind her like a giant, his tie flapping this way and that, his cheeks growing redder, his veins beginning to stand out on his forehead.

I was the first to come, melting blissfully into that hot, eager mouth. She didn’t withdraw her tongue, but kept on kissing my spread lips until she moaned into them, her own orgasm forced from her by the boss’s purposeful thrusts.

He held on a while longer, seeming to enjoy his view enough to want to prolong it, but eventually he too joined us in our post-coital haze, collapsing on top of Mara’s back with a roar.

‘Well, Kim,’ he said, once he had Mara over his lap to remove the plug. ‘Thank you so much for your input, but I hope we haven’t kept you from your duties.’

Oh. My duties. I should have finished polishing the silver in the drawing room ages ago.

‘Oh, right,’ I said, looking from him to her.

Mara smiled at me with lazy satiety. ‘That was awesome,’ she drawled. ‘We’ll come here again.’

‘I hope you do,’ I said, smoothing down my skirt. ‘I really hope so.’

Without him, next time.

‘Here’s my card,’ said the boss, handing it over.

It read: ‘J Barraclough. Professional disciplinarian and dom. All submissive tastes catered for.’

‘Oh! So you aren’t …?’

‘We have a purely business relationship,’ said Mara. ‘You can have my card too, if you want. Or just my mobile number.’

‘I’d like that.’

Leaving the room with Mara’s contact details, I praised whoever might be the patron saint of voyeurs. And, as I passed the bust of the old lord, I almost thought he winked at me.

Property Of

Sommer Marsden

‘Winona,’ he said. Just him saying my name sent a shiver up my spine. I turned a bit too fast and almost propelled myself out of my office chair. Which led to a nervous little titter.

Nice. Very sexy.

‘Mr Bennett,’ I said, nodding.

I wanted to look cool, but I felt like I was vibrating. How long would this last? I wondered.

He smiled as he put some papers neatly on top of his stack of folders. His suit was charcoal grey, his tie a navy blue, his shirt white. All very boring components that did nothing at all until you tied them all together by hanging them on a lean but muscular handsome man. A breath-stealing kind of handsome.

Trevor Bennett. My boss of all things.

‘Can you come into my office, please?’

The word ‘can’ was a joke. He meant: ‘Come into my office. Now.’

I nodded and cleared my throat. I had nothing to say, but he just made me feel that way. Like I had something stuck in my throat – maybe his cock. I bit my tongue to stop myself from laughing and then said softly, ‘Coffee?’

‘Already have some. We need to discuss tonight.’

Tonight? I had no idea, but I faked like I did and locked my computer. ‘Coming,’ I said.

That made him smile.

***

Trevor Bennett is a powerful man. He plays with money the way I used to play with dolls as a young girl. I followed him into his office, feeling like my legs were only a mirage. That they couldn’t actually support me. My spiffy black slingback heels tip-tapped on the hardwood floor. They are his favourite shoes. I wear them often. And often when I wear them, they are all that I am wearing.

Trevor indicated a seat and I took it, smoothing my skirt primly because I knew it made him think dirty things. It often made him do dirty things shortly after thinking them.

‘Tonight is the big wooing party. We bring in all the millionaires and billionaires and all those we want to bring into the fold. We woo them and wine them and dine them and try to convince them to let us play with their money.’