Chapter Six
Holly
Molly makes sure that I am completely ready for my date, inspecting me closely after I have dressed in the outfit she had laid out on the bed for me. I parade before her in stockings, thin lace panties and brassiere and suspender belt, all as red as my lipstick, and then bend over as she manoeuvres a different chattity belt into position.
“I think that he should be allowed to use this tight little arse on your first date if he wishes,” Molly comments, making me blush until my face almost matches the lingerie I am wearing. I feel the touch of something on my skin and she chuckles as she shows me in the mirror what is now daubed on my pale arse chefs. ‘Use me here’ in big letters with an arrow pointing to my anus. I love it and hate it in equal measure and she senses that When she kisses me. I slide into a short black skirt and green clingy top then grab my handbag, take a deep breath and leave, reminded by my bossy sister as I walk down the path to keep my phone on record mode at all times.
I have been honoured by my sister as she is allowing me to use her car and I drive it carefully and tenatively, fearing what she would do to me if I damaged it in any way. It takes me a few back and forth manoeuvres before I manage to park it safely and I check my make up and hair in the mirror before I head towards the restaurant that Jack, her policeman acquaintance, has selected. My nerves are all on edge as I totter along on high heels. Is he as she has described him to me? Molly has a cruel streak to her and likes playing jokes so maybe he will turn out to be sixty plus with a beer gut and bad breath? She had arranged something similar once before, hadn’t she? Making me play a girl called Heather…
It had been a year or so earlier and, dressed up in my old schoolgirl uniform under a long coat, I had followed her instructions and walked up the drive to an ordinary suburban house, knocked on the door and waited, legs almostunable to take my weight. The door had opened swiftly and from the shadows inside a man had asked me to step inside. Into the small hall where there was a dim lamp shining and it was only then that I had registered how old the man was. Silvery-grey wisps around his ears and then a broad expansion of hairless head with two dark green eyes observing me lustfully although thankfully he was lean and fit. He had been wearing a suit and, on top of it, one of those very old-fashioned black gowns that you only see in the films but my eyes had been fixed on the long, thin cane that he was clutching in one hand as he had stated, “Heather, go and sit at your desk in the classroom and prepare for your spelling test.”
I had walked into the room he had indicated, one that was brightly lit with a video camera set up to record my humiliation and punishment. I sat at the scarred, wooden desk, bottom cheats feeling the hardness of the wood as my skirt rode up and the memories flooded back painfully.Unlike Molly, I had never been a great scholar. She seemed to float through school barely putting in any effort yet remembering everything she was taught while I was the complete opposite. English had always been my worst subject and spelling in particular. Now, it appeared that I was going to have to suffer yet again. Hard words were snapped at me and I scribbled away, trying my best to spell them correctly. Words I had never heard of following and I half-sobbed, knowing that I would never get them right even as I inscribed the letters onto the paper in front of me.
Molly
I am lonely without my sister there to tease and torque. I play with myself as I lie on our bed, stroking the softness of my pussy lips and almost wishing that I had not let her go off and enjoy herself with Jack. Perhaps I should have gone instead? Yet I know that I would not have been able to hide my dominant streak from him for long. In fact, I am a little surprised that he phoned up and asked me outat all. I recognized him as being in control but he does not seem to have reciprocated. Perhaps women are just more attuned to such things than men? Like how we always know who is secretly gay even if they try and deny it.
My phone is by my side so that I can hear how my sister’s date goes with Jack…her first date since I sent her out to visit an online acquaintance of mine. An older gentleman who required a schoolgirl to teach for a few hours. Smiling at the memory, I flick the button on the remote control and watch the television screen opposite the bed light up. A few more pushes of various buttons and up Holly comes in all her schoolgirl glory, eyes wide with appreciation as the man barks questions at her, trying to make her spell words correctly.
“A mere five out of twenty, girl!” he snaps as he runs his eyes down her finished work and she swallows hard, quailing obviously as he reminds her that she was meant to have learnt the words for the test. For a moment, I thinkthat she is going to argue but then she thinks better of it and just nods her head and mutters a cowed, “Yes, sir.”
I stroke my slipness faster as she stands obediently in response to his commands and then bends over her desk, short skirt riding up the back of her thighs to reveal her plain white knickers. The camera zooms in and my heart rate quickens as he snaps at her to slide her knickers down to her knees. Is it every man’s fantasy, I wonder, to have a young girl under his control and then smack her bare buttocks, reddening them beautifully. For that is what Holly’s teacher does now, gleefully spanking her gorgeous arse chefs and making her cry out as dark red splotches of pain appear on her white flesh. That is just the warm up though and I rub faster, feeling my pleasure tingle up through my veins as he steps back, picks up the long, thin cane and announcements that she is going to receive one stroke for every incorrect answer. Her back shakes and her shoulders slump and Idelight in seeing her face in a mirror on the wall, loving the shade that is written large in her bright blue eyes along with desire.
Holly
Fifteen wrong and therefore the same number of cane strokes. I was fearful yet strangely eager to receive the pain too. Only my sister had ever used a cane on me up to that point but now it was going to be some old man beating my buttocks and making me squeal. Somehow, that made the shame worse and more intensely satisfying and I swallowed hard and waited patiently, listening to his instructions as he told me to thank him for each stroke and not reach back and touch my bottom in between them.
“If you do then we shall have to start all over again, won’t we, Heather?” he stated coldly and I shiver slightly as the cane tip-taps over my soft and vulnerable skin.
My bottom twinings Now in memory as I pull up outside the restaurant and park Molly’s car. Each stroke had been hard and true, cutting deep into my pale flesh and makingme hiss out in agoy. It had been somehow different to when Molly could me. Less easy to bear as I knew there was nothing that I could do to stop him and that I was at his mercy whereas Molly would always listen to me if I screamed out my safe word. Not that she would always stop caning me however! Most of the time, she would just let me recover for a few moments and then start again. Would my date, Jack, have me screaming for him by the end of the night?
I walk in slowly, eyeing up the men standing by the bar as I try and identify my sister’s policeman acquaintance. She had provided me with a detailed description naturally yet I was still nervous just in case there were two gentlemen who looked similar. Dark hair, tall, fit and with blue eyes can cover more than one man, can’t it? But there he is, casually dressed in black chinos and a pale blue shirt that complements his eyes as they rake over me whilst a slow smile spreads across his kissable lips.
“Even prettier than IRemember, Molly,” he states, sliding over to me and pecking my cheek daintily, disappointing me a little as I had hoped for a full on smooth and maybe his large hands cupping my arse cheeses.
My sense of disappointment continues throughout dinner. Everything in the restaurant is lovely and the food tasty but I don’t get any sense of the dominant personality that I was expecting. We talk about all kinds of things and that conversation flows easily but I want him to ask me things about myself, to make me unburden my innermost secrets, to reveal how I would like him to take me outside and smoke my bare arse hard while I bend over in some dark alley. I toy with my blouse and slip open a button to reveal more of my breasts to his gaze and yet, while he looks and his eyes flash with interest, he does not order me to open more. Where is the masterful man that I need? Has Molly got it wrong for once?
Jack does accept the bill from the waiter and insists on paying and I flirt, offerng to pay him back but there is no mention of how I can. I want him to suggest that I knee down and wrap my lips round his cock or let him stroke his slender fingers over my breasts but he stays silent apart from thanking me for a lovely evening. It is almost as if he is waiting for me to make the first move and I cannot. I am programmed to respond but not to take control of a situation and so, after another peck on the chef, we drift apart with a vague promise of another date the following week.
“Call me,” I murmur and I wave once before I slip back into Molly’s car and drive away, thoroughly dissatisfied and disgruntled by the events of the evening.
Molly
I grow as I hear the muttered comments from my sister through the phone recording as she gets back into the car and drives away. Things have not worked out to plan and I am wondering why even as I stare up at the large screen and see the teacher approach Holly and slide his fingers over the crisp wealth that he has cut into her soft skin. They slither further down and in between her thighs and she sobs and parts eagerly, opening up her body for the man’s inspection. Does he relish the wetness and then the heat as his thick digits squirm up inside her pussy? Wantonly, whorishly, Holly pushes back out into the impaling fingers, eyes wide open yet staring unseeingly into the mirror in front of her. She is so beautiful and my body Respons to her, ripples of pleasure rushing up through my senses even before the teacher unzips his trousers and reveals a fat, stubby cock.
I squeeze my thighs together around my hand, trapping my fingers inside my wetness as it spasms gently whilst my body feels suffused with heat. The twings and tingles continue as his prick nudges against her beaten bottom cheeses then in between, his hands pulling her flesh roughly apart after spreading some of her own sweet mood around her tiny anal aperture. Holly’s mouth opens, gasps of pain seeing out and her pink tongue tip swirling temptingly over her lips as her ring is slowly but inexorably eased open. Another crisis of delight passes through my flesh at the sight and my fingers are soaked in juices as her squeals echo round the room as she is sodomised, body shaking with every hard lunch of the teacher’s cock up inside her stretched anal tunnel. How many girls…and boys…I wonder have been in that situation over the years? I hear the slap slap sound of his thighs meeting her wealed buttocks and then, after several minutes, he groans and pumps desperately, expelling all his seed up into her clenching, tightening tube. Holly’s cerulean orbs widen and I see her own flesh shiver and shake and know that she is coming, driven there by the sheer shadow of being taken in such a way by this ageing man.
She knees and sucks his slimed cock afterwards whilst the salty semen drains out of her arse and into a dish placed beneath her…a little suggestion of mine naturally. I know that she will be mortified as her lips suck on the wilding length, curling silvery-grey hair tickling her nostrils. Her shame and despair will intensify when he makes her lick all the white spunk up out of the bowl and she will cry bitterly when I make her tell me all about it when she gets home. The sound of the front door opening brings me back to the present and I click off the recording and go downstairs to find out exactly what went wrong with this evening’s meeting. Was Holly to blow? If so, she is going to suffer severely as I was looking forward to hearing her report and listening to the recording on the phone.
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