by Sadie Wolf
His please s turn to fuck-fuck-fuck s and I know he’s going to come. I wish I could see his cock, wrapped and rubbed a little raw, as he lets go, but it’s enough that I can imagine it. It’s enough that I can see his ass clench tight under my hand. I tighten my grip on the ribbon, use it to help his momentum. I up my spanks, faster and harder, meeting his ass each time it rises, and then giving a sharp hit on his downstroke.
Soon, he comes the way boys do: loud and quick, and drenching the front of my skirt. The room smells instantly like sex and sweat and cum. While his body shivers and pumps, I softly stroke the sore places on his skin. Small bruises – from the book, likely – are beginning to show through the pink. He’s going to feel this every time he sits down for the next week, maybe longer.
He lays across my lap for a long time while I stroke his skin back into the memory of softness. After a while, my thighs start to ache. The rest of me is already aching for my fingers, the memory of him behind my closed eyes. Later, I tell myself. Wait. Keep this pleasure.
‘Stephen, it’s time to get up,’ I say.
‘Oh, oh yeah.’ When he slides off of me, his grin is all boyish, but not flustered or embarrassed. Not any more. Chest and cock still jut, still pink, with more power now, not less.
I brush a hand over the front of my skirt where the fabric is wet. My fingers come away ink-stained.
‘Here, let me cut that off you.’ Careful with the scissors, I cut through the ribbon at his wrists and waist first, and then slice against the softening skin of his cock. He doesn’t flinch, not even when the scissors touch his skin. ‘There you go.’
I gather up the ribbon that has fallen from his body. I’ll use this later, remembering. I admire my handiwork across his body – black ink, pink handprints. I wonder what he’ll think of later, after, when he undresses and sees the marks I’ve left on him.
‘What about you?’ he asks.
‘Tuesday afternoons,’ I say. ‘You can wash windows.’ Him and Anthony. I think they’ll work well together.
‘No, I mean, what about you .’ He actually points in the general direction of my skirt, which makes me want to laugh. Someone is training these boys well, long before they come to me.
‘You’re off the hook for now,’ I say. ‘Next time.’
He actually looks a little sad. ‘Oh, okay.’
I pick up his book. ‘I’ll wrap this up for you to take home. Come on out when you’re ready.’
By the time he comes out, I’ve tucked my hair back up in its up-do. I’ve reapplied my lipstick. I have my pencil between my lips, the taste of lead in my mouth. My glasses are tucked between my breasts. He’s looking and not-looking at me again.
I slide the book across the counter to him. ‘I hope you enjoy this,’ I say. ‘It’s been bound quite beautifully.’
His face actually goes pink, from the cheeks on up. The reminder of the colour sends a small shiver through me.
‘Oh, and flip the sign on your way out, will you?’ I watch him walk out, memories of that ass beneath my hand. When the door shuts, I lean over and start making squiggles on my paper. I’m expecting the dark-haired boy who does my books any minute now.
Advantage Headmaster
by Philippa Johnson
The shadows were lengthening across the sweeping lawn in front of James Bendrick’s office. A light breeze drifted in through the open window, as did the distant chock chock of tennis balls from the main court behind the schoolhouse, where the annual inter-school tennis tournament was in progress. His establishment – a private girls’ boarding school – nearly always walked away with the top prizes. Trophy cabinets were full of the results of previous years’ hard work. Something was troubling Bendrick though: the usual whoops, cheers and occasional applause were interspersed with strange catcalls and wolf whistling.
He reached forward to a bank of switches close to his desk, and a large flat-screen TV flickered into life. Adjusting the remote control, he quickly found what he was looking for: the camera covering the school’s centre court showing the final match in progress.
On court was Nina Birch, Bendrick’s personal choice for head girl. Tall, blonde, athletic: she was the perfect choice. Her shapely hips and prominent firm breasts were flattered by the tight white T-shirt and her short tennis skirt barely covered her ample derrière.
In addition to being head girl, Nina was the deserved captain of the school’s elite tennis squad. As Bendrick contemplated the spectacle of Birch bending forward to retrieve a tennis ball, he inhaled sharply: rather than seeing her buttocks neatly framed by the regulation crisp white knickers, edged with lace, Birch appeared to be entirely naked beneath the microskirt. A good thing, he mused, he was able to access an instant replay. He did so and slowed down the action to get a better look. When Birch bent right forward to retrieve the ball, the space between her thighs glowed white. She had on the tiniest thong; the back strap concealed by her muscular buttocks. The bending forward coincided with another chorus of catcalls from a group of sixth-form boys from a nearby school. So that was it: he would have to deal with Nina after the match. His tongue ran over his lips, savouring his evening’s entertainment.
One Hour Later
Bendrick was roused from his perusal of the evening paper by a faint knock at his door.
‘Come!’
Nina Birch stepped into the room still clad in her tennis attire, sporting a rosy glow, flushed with success and, Bendrick thought, a slightly mischievous smile playing around her lips.
‘Good match, Nina?’ he enquired nonchalantly.
‘Oh yes, sir. We won again and it was all decided by the final match,’ she said breathlessly.
‘I’m sorry I couldn’t come to watch, you know how I take a personal interest in my tennis girls.’
‘Indeed, sir, I think you missed a treat today,’ she smirked imperceptibly.
‘Good job I had the CCTV installed this year, then. It was almost as good as being there.’
‘Oh … I … didn’t realise you could watch the match, sir,’ she began to stammer as the colour drained visibly from her cheeks.
Bendrick went on, barely acknowledging her nervous interruption.
‘It was the demented cheering of those sixth-form boys from St Stephen’s that alerted me,’ he said.
He took a tennis ball from one of his desk drawers and tossed it so that it landed in the middle of the Persian rug that occupied the centre of his vast office.
‘Now, bend over and retrieve that ball.’
Nina knew better than to argue: she stepped forward and reached down with her right hand. As she did so, her pleated white skirt rode over her fleshy posterior. She straightened briskly and the hem came to rest a couple of inches below the crease twixt buttock and thigh. She turned to face him, her hands folded neatly before her.
‘Since when do you girls decide what undergarments to wear?’ he thundered.
‘As you know well, the senior girls in my establishment have their underwear personally selected by me. Thongs may well be appropriate, especially if you’re coming here for some personal attention. Sometimes even for a night out when wearing a tight-fitting skirt or skin-tight trousers. But never on the tennis court.’
‘Well, the boys were certainly enjoying it,’ she said with a smile.
‘Enough! You know you’re making things worse for yourself, Nina. In two weeks you will leave this school and go to university. I want you to be an asset to this place, and in the next two weeks I intend to drive that lesson home forcefully. I’m sure you know what I mean.’
Birch looked down at the floor. As head girl she was more than used to the headmaster’s attention. A summons to his study induced in her a curious, nervous excitement. She found a session with Bendrick would often leave her glowing and expectant; a feeling she would often recall while exploring herself under the duvet at night.
And, as head girl, it was her duty to discipline the other senior girls; a duty she had grown to relish. She ha
d progressed from lightly spanking the others over their school mini-skirts to full-blown, bare-bottom thrashings using the crop, wooden paddle and, occasionally, the cane Bendrick had presented to her after she was elected head girl by the senior staff.
‘What you have done is so serious that a mere thrashing, even a severe caning, will not, I think, do the trick. I’m going to push you beyond your limits, introduce you to pain and sensations in other parts of your body. This will be an experience you will never in your entire life forget. And when we’ve finished this evening, it will be repeated, daily, until you leave the school.’
‘First, you will fetch the large, leather punishment bench from my outer office and you will arrange yourself in the customary manner.’
Barely half a minute later, Birch was draped across the large punishment stool. Her knees were on a padded ledge just above floor level while her torso was splayed horizontally across the expanse of black leather. Bendrick had the authority to strap girls to the bench, though it was something he seldom chose to do because it was his belief that girls must submit voluntarily if they were to grow up into respectable young women.
‘Knees apart!’ he barked.
The punishment bench was constructed so that its occupant was forced to thrust back her rear in order to remain comfortable. Even at this angle, the string between Nina’s buttocks was almost invisible. Bendrick moved swiftly behind her, grabbed the top of her miniscule thong and tugged it swiftly upwards.
She gasped in pain and surprise as the string bit into the crease of her bottom.
‘Dental floss for the buttocks, eh?’ sneered Bendrick. He gave the string several sharp tugs and Birch squirmed, straining to retain her dignity.
Abruptly, he let the garment go and it twanged painfully back into place. She knew better than to cry out in pain; a sharp intake of breath was all that could be heard. Then silence.
Without warning, the slaps started to rain down on Nina’s exposed behind. These were not the almost playful slaps he often delivered to warm a girl up; his arm swung back and the palm of his hand landed with full force on the firm, rounded cheeks of her youthful behind. Her face was buried in the leather and she emitted small grunts with each resounding slap. Later, several of her friends told her they could hear the spanking across the lawn in the schoolhouse. Bendrick had pointedly left the window open in order to make an example of her.
Her cheeks began to redden; changing from light pink through scarlet to a deep, angry purple. When Bendrick was satisfied that her rear was covered in its entirety, he began to aim the slaps lower. This was a new sensation to Birch; school punishments were normally restricted to a girl’s bottom, very occasionally the palm of the hand was also thrashed. She twitched and squirmed as her thighs and the backs of her legs began to sting and burn. Still, though, she knew better than to cry out in pain.
After five minutes or so, Bendrick was satisfied that his initial attack had had its desired effect. Birch was subdued, breathing heavily and fighting back tears.
‘Stand-up, Nina, and come over to my desk,’ he ordered.
As if nothing had happened, Nina got up from the punishment stool, smoothed her white skirt over the smarting skin and stepped forward. She was motioned to come around the side of the desk, standing next to the headmaster, avoiding eye contact.
‘Now lift that skirt so that I can have a good look at your choice of undergarment,’ he coaxed.
Nina lifted the hem of her pleated tennis skirt and held it at waist level. The front of the thong was almost as skimpy as the non-existent back: a film of diaphanous fabric showed off her shaven mound to perfection. The sides were of intricate lacework and a small embroidered heart was placed directly over the top of the start of her labial crevice.
‘Very pretty, I’m sure. In fact, you must tell me where you bought it because it’s an ideal punishment garment. It leaves nothing, or almost nothing, to the imagination.’
‘Erm … it’s from Agent Provocateur, sir,’ she whispered.
‘Reassuringly expensive, eh?’
She opened her mouth to reply but was caught off-guard as she felt Bendrick’s finger gently tugging at the side of her knickers. She knew that he took a close interest in his girls, but never before had he so blatantly invaded her feminine intimacy.
Holding the flimsy garment to one side, he gently brushed his fingers against her labia. She shuddered with fear and excitement. Her outer lips were perfectly smooth, freshly shaven that very morning.
The shaving of pubic hair was mandatory for all girls and the results were checked on a daily basis by Matron. Nina and the others strongly suspected that this was a duty to which Matron had no objection, as she would often linger in her inspections of her favourites. The girls would line up outside the dormitories, skirts held to their waists, while Matron would pass along the line, sliding her long fingers into each girl’s white school knickers in turn. A girl who did well was rewarded by a finger gently circling her clit, sometimes even entering the moistness of her vagina.
‘Good girl,’ Matron would say. ‘Now off you go and have your breakfast.’
Those who tried to skimp on their morning shave would first be subjected to a full inspection. This involved lowering her knickers to her knees, spreading her legs so that her underwear was taught, bending over and grabbing her ankles. This allowed Matron a full view of the offending genitalia including the anus and bottom crack.
She would first pass along the line, slapping here and pinching there before entering her office to retrieve a small flogger. She would then pass down the line in the opposite direction, flicking out mercilessly at the exposed buttocks and into the girls’ most intimate folds. Once satisfied that the recalcitrant girls were all burning to their inner cores, they would be told to straighten up, place their knickers in a laundry basket at the end of the corridor, and report to Nurse Midgley for waxing. They would, of course, miss breakfast and were obliged to spend the rest of the day minus their undergarments. This policy was designed to encourage the girls to maintain exacting standards of intimate hygiene. The penalties for not doing so ensured that it worked.
Back in the study, Bendrick began a more thorough examination of Nina’s intimate contours. ‘Lie down on my desk and place your feet so that they almost touch your buttocks,’ he said firmly.
Nina lay on her back and stared up at the ornate ceiling. She felt strong hands pulling the sides of the thong and she obligingly lifted her buttocks off the leather-topped desk to assist with its removal.
He parted her knees with his hand and, extending two fingers, entered her vaginal cavity. As he did so, the tip of his thumb brushed lightly against the tip of her clitoris. It was all Nina could do not to scream with pleasure and anticipation. Her breathing became deeper and her pupils started to dilate.
He began to move his fingers in and out and she responded with tiny thrusts of her hips. Her cunt began to moisten and her head moved rhythmically from side to side. Sensing her growing excitement, he used the little finger of his right hand to circle the bud of her anus. This at first tightened instinctively, but Nina was far too well trained to deny access to a superior. She allowed her sphincter to relax and, moistened by her own wetness, the finger began to explore.
Nina’s face was flushed with ecstasy and, calculating his moment exactly, Bendrick abruptly abandoned his stimulation of the writhing 18-year-old. He took a thin leather strap from his desk drawer and brought it down swiftly across her splayed labia. Without a thought for decorum, Nina shrieked and closed her legs instinctively.
‘Get those legs open!’ he barked.
The strap hissed through the air once again and landed, this time vertically, on her splayed pussy. Her clit began to sting and she screamed at the top of her voice.
‘Get used to it, Nina, if you relax a little I can even bring you off this way.’
He brought his hand up to his shoulder preparing to strike again. Nina fought to control her breathing and readied hers
elf for the next slice. It landed on her clit and she bucked involuntarily. Then another and another and another in exactly the same spot. And with each new impact another thrust of the pelvis upwards. A few more strokes and her entire genitalia was ablaze. It was certainly painful, but there was something else as well – a growing excitement, a building pressure, a longing for release.
‘You’re nearly there,’ he whispered. ‘Just breathe through the pain and try to ride it.’
The strokes became even more intense and she surprised herself by raising her hips ready to receive the next.
‘Now countdown from twenty to one,’ he ordered.
‘Twenty … ah! Nineteen … ow! Eighteen … oh, Headmaster!’
Nina was only aware of the pain, the boiling excitement and the need to concentrate on counting backwards. Each swish of the strap became more intense and landed on top the previous strike, intensifying the sensation.
She was down to ten, her breathing more rapid and her eyes closed and she felt her climax mounting.
‘Nine!’ she screamed. ‘Eight … oh God … seven …ah! Six, oh oh oh … Five! Four … Christ! I’m … I’m … coming. Three! Please, I … can’t. Two! Fuck! One!’
Nina was enveloped by strange and unfamiliar sensations that seemed to pulse from her toes to her head. She writhed uncontrollably on the desk as wave upon wave rippled through her body.
Bendrick padded across the Persian rug and opened his walnut cocktail cabinet. He withdrew his ice bucket and returned it to the desk across which Nina still lay. With a pair of silver tongs, he retrieved an ice cube and began to rub it over her swollen pussy lips. The sensation was a sweet release from the stinging torment of his strap. She uttered little sighs of contentment as the cold substance drew the heat from her throbbing cunt.
‘That’s just the beginning, Nina,’ he said. ‘Now we’ll progress to the next stage of your correction.’
