The Riding School

by C. P. Mandara

  Jenny tried instinctively to cover herself up, acutely aware of how naked and exposed she was. Of course the effort was pointless. All of the most intimate parts of her body were on display and he didn't even bat an eyelid. To make matters worse, the man was drop dead 'I've died and gone to heaven' gorgeous. He had a posh English accent, short black hair gelled upwards in soft spikes and chocolate-brown eyes. If that wasn't enough, add tight white riding breeches, a white shirt, a pair of black knee-high boots and a matching riding coat. Most women would have melted into a small puddle before him and she was definitely one of them. He was quite possibly the most desirable man she had ever had the good fortune to lay her eyes upon and she had to meet him like this. Life was not fair. A groan of frustration left her lips as her body began to heat once more, blood pumping furiously through her. Oh no, she thought, this cannot be happening yet again. Gritting her teeth she tried to quell her reaction.

  'Did you want to help perform the exam, Master Mark?' asked Hetty.

  Jenny tried to shake her head in horror, knowing that as soon as the man's fingers touched her she would explode. It had been bad enough being observed by the two old ladies, but having an attractive man there to witness these depravities would make it ten times worse. With all her might she willed him to say no.

  'Well,' he paused, as if thinking for a moment, 'how about I sit over here in the corner and watch? If you need a hand with anything you can let me know.' The devilish smile he gave to the ladies indicated that he knew his presence would give an added torment to their victim.

  Jenny tried to thrash about on the horse to let her feelings on the matter be known, but other than her bottom sliding around on the leather which was now slick with her own juices, there wasn't much movement of any account and no-one paid the slightest bit of attention to her.

  In a few brief seconds Mark had settled himself quietly on a wooden stool that would give him the best view of everything that would shortly be happening between Jenny's legs. Hetty, meanwhile, had grabbed the larger steel speculum out of the water again and was slowly patting it dry with clean linen.

  'There, there, horsie,' said Hetty, who had watched Jenny's attempted protest with amusement. 'Most of the fillies around here would kill for a few minutes of Master Mark's time. Give him a few hours and I'm sure you'll be drooling at the mouth along with the rest of them.'

  That was exactly what Jenny was afraid of.

  The Exam, Part II

  The speculum slid into Jenny in one single motion. Most of that was due to the added presence of Mark, who had made her so wet that her body was practically 'gushing' with enthusiasm. It was mortifying and there was nothing she could do to control her reaction. As the blades of the speculum pulled at her inner walls and stretched them, she felt herself being opened and displayed for these three strangers and it wasn't as unpleasant as it should have been. Jenny was aroused. She knew Mark's eyes were upon her most intimate parts and it made her hot; breathlessly, heart-poundingly and deliciously hot. She squirmed.

  'Interesting reaction,' said a deep male voice.

  'I think most of it is down to you,' said Agnes, who couldn't help a smile.

  Hetty picked up a long cotton swab and bending over Jenny's torso, all the buttons on her starched white linen shirt straining, took a sample of cells from Jenny's cervix. She talked as she worked, letting her patient know exactly what was happening. 'We're just checking for any abnormalities or lesions. The sample of cells I've just collected will be sent to our laboratory and if there's anything that concerns the technician then your Master or Mistress will be notified and will take it from there.'

  That was when Jenny started to realise that all control was going to be taken from her. If she'd contracted cancer, she wasn't going to be the first to know. Until she could arrange her escape ticket out of here, her life was no longer her own. To say it was a sobering thought was something of an understatement.

  The speculum was slowly closed and extracted.

  'Right,' said Hetty, 'we'd better get started on the rectal exam. Can you get me some cushions, Aggie?'

  As soon as she heard those words a new wave of rebellion swept its way through Jenny and she renewed her struggles with vigour. She had never before been touched in that particular part of her anatomy and she certainly didn't want to start in this room, with these complete strangers watching over her. She would not stand for this. Helplessly, she watched as Aggie plumped up two large, overstuffed cotton cushions and placed them under the small of her back. This had the effect of thrusting her bottom into the air, giving a much better degree of access for whoever chose to perform the exam. Struggling had no effect and the cushions would not be moved.

  'What does it say on the form for anal, Aggie?'

  Agnes consulted the paperwork on her desk again. 'Unknown.'

  'Have you ever had anal sex before, Jenny?' Henrietta asked softly.

  Jenny shook her head as fast and as hard as she was able.

  A soft male chuckle served to further humiliate her.

  'I think she's going to be very popular around here,' said Mark, trying to suppress a grin.

  'My, oh my,' said Aggie with awe, 'an anal virgin. We haven't had one of those in years and years.'

  All Hetty did was grunt in response. 'I have a feeling I'm going to need some help with this. Would you keep her distracted for a moment or two, Master Mark?'

  'It would be my absolute pleasure,' came the immediate response.

  It eventually occurred to Jenny that wriggling about like an anaconda was going to give everyone more of a show, rather than less. So by sheer force of will she managed to stop herself squirming madly, but only just.

  'May I take out her gag?' Mark looked to Hetty for an answer.

  'You are the ruling authority here,' she replied, 'but I thank you for asking. Feel free to do as you please with the trainee.' Hetty thought for a moment. 'She's going to need a "breaking in" session later, if she has any chance at all of wearing a tail tomorrow. Would you like us to leave a little present inside her, if you catch my drift?' She smiled innocently.

  'I think she would like that,' said Mark.

  Jenny wasn't at all sure that she would. No-one was touching her down there and as soon as Mark removed her gag they were going to find out just what she thought of them all, and it wasn't going to be particularly polite.

  'Right, I'm going to remove your gag on two conditions,' said Mark, which immediately focused Jenny's attention. 'One, no biting. Two, no talking unless spoken to. Nod if you understand these conditions and agree to comply with them.'

  Jenny was no fool and nodded her head quickly.

  'Just for clarity's sake, there are three good reasons you'll do exactly as you've been told: there is a riding crop attached to my belt and I am itching to use it. Two, I bite harder, and three, you are going to spend the next three or four hours in my company and I am a Master at torture, amongst other equally unpleasant things that you may not want to find out about on your first day with us. Are we clear?'

  Jenny nodded. She'd take her chances where she could find them, threats or no threats. Besides, no-one would dare mess with Jenny Redcliff, when they found out who she was and what her father was capable of.

  When the gag came out it made an embarrassingly loud sucking noise and left a long trail of saliva from her mouth to the trolley, which was where he placed it. He broke the connection and before she had a chance to voice all the rather pressing concerns she had at the top of her lungs, he took her lips in a brutal and punishing kiss. He literally sucked all the air from her body and it was... electric. He licked, nipped and even gave her bottom lip a small bite and she loved it. Gone were all thoughts of stamping her feet, screaming and shouting with rage, or contacting a lawyer. In their place was an escalating need which was increasing by the second.

  Mark's eyes watched as Hetty reached for the smaller speculum and he gave a tiny shake of his head. That wasn't going to be happening today. They would be
lucky to get a measurement. It wouldn't pose a problem. All ponies had regulation visits to the vet and she would get her fair share of attention then. He picked up the slimmest-ruled dildo on the trolley and handed it to the gloved fingers which were still hovering in midair. She nodded silently and covered it in as much lubricant as possible.

  When the cold, slippery glass dildo was placed at the entrance to her anal passage, the shock was evident in Jenny's eyes. She did not want to be touched down there. Another round of frantic struggling ensued, but the dildo remained irritatingly in place and no amount of wriggling would shift it. It didn't matter because Jenny had clenched her sphincter so tight that they'd be lucky to get a matchstick near her. She was not going to let down her guard.

  Mark's eyes had a knowing gleam in them. It wasn't a secret that he preferred it when the trainees played hardball. Give him obstinate, unruly, rude, sarcastic, narcissistic or greedy any day. They were a lot more fun to tame than the 'Miss Goody Two Shoes' variety. Jenny was definitely not going to fall under the latter category and that was so much the better. She already had him smiling. Now that he'd pulled away from her lips he could see her gritted teeth and narrowed eyes. She believed she would be able to deny them entry just by tightly tensing her body. The girl had a lot to learn. He whispered in her ear.

  'That long glass dildo is going to be filling your ass as far as it can possibly go whether you wish it or not. Not only that, but in a few short weeks you are going to beg to be fucked in that hole or indeed any hole your trainer may choose. You will have to beg for the privilege of serving your Master or Mistress and perhaps, if you are lucky, to earn a rare moment of release. One of the things that all pony girls or boys have in common is that their asses are rarely left unplugged. That's why you'll need a "breaking in" session. At the moment you'll only be able to take the tiniest of plugs, which means your tail will be of a very unimpressive thickness and length. Your trainer will work with you every day until that beautiful backside can hold the weight of a proper horse's tail inside it. Every single moment you wear it, when you feel the coarse hair tickling your inner thighs or feel the plug vibrating inside your body, it will remind you of your status. As of now, you are an animal. There will be no speech, no clothes and no conscious will of your own. Ponies are no longer seen as human and your sole purpose in life will be to please your owner. You would do well to remember that.'

  The words that dripped inside Jenny's ear made her go cold with fear. She had little time to dwell on them though, before his fingers began to torment her body. They were skilled, expert fingers that knew exactly how to play a woman; a soft brush on the underside of a breast, a light caress down the length of an inner thigh, a flick of a fingernail against the tender point of a nipple or a slow, sensuous lick following the curve of the neck. It didn't matter where his fingers landed as they had more magic in them than a witch on All Hallows' Eve. They made her gasp, shiver, tingle and burn. She was supposed to be screaming, shouting and demanding her release, but the spell she was under had her body coiled with tension and her mouth moaning in pleasure. Try as she might, she couldn't snap herself out of the sensual haze that had befallen her.

  'You're not going to give in that easily are you?' asked Mark, raising his eyebrows in challenge. 'I thought you were going to prove a tough little filly to tame and yet here we have a purring pussycat.' His fingers gave her clit the lightest of strokes, that tiny pressure nearly all that was needed to send her over the edge before nodding to Hetty, who, in one swift motion, breached the tightly clenched inner anal walls to lodge the measuring dildo inside her back passage.

  Jenny's orgasm died an instant death as the pain of having her anal walls dilated took hold. She shrieked and bucked and shrieked some more for good measure. It took another hard, brutal kiss and vigorous pressure on her clit before the noise subsided. She could feel her sphincter convulsing madly around the foreign object lodged inside it. It was not welcome, but that didn't stop her tormentor. Hetty twisted and turned the thin, cylindrical glass rule inside her and urged it forward. Jenny tried to stop the dildo's insidious movement, but squirming with all her might just seemed to encourage it to slip more deeply inside her, so she stopped even that small token of protest. Compressing her lips together, she gave Mark a baleful glance, eyes flashing pure malice. If he wanted his lips anywhere near hers he'd better be prepared to do battle.

  'Now that's what I'm talking about,' said Mark, as the corner of his lip began to twitch in amusement. He turned his attention to Hetty, still carefully poised over Jenny's groin. 'How far have you managed to get?'

  'Three inches, Master Mark,' came the somewhat concerned reply.

  She had a right to be concerned, for that wouldn't do at all, thought Mark. The bigger the eventual plug a pony could take would affect her value considerably and you weren't going to manage a great tail with just three inches to play around with. Time would tell if it was going to pose a problem and the first few weeks of training would be crucial. Still, he suspected that Hetty had given up a little too soon. 'Would you mind if I have a go?' he asked.

  Hetty shook her head and smiled. She was more than happy to let an expert take charge and she had a feeling that Mark would achieve more success than she. The man ratcheted up female heart rates by just breathing. She held the rule in place until Mark had closed his fingers around it and then took a seat next to Agnes.

  Jenny did not want Mark anywhere near her ass or anywhere near her at all for that matter. She finally managed to find her voice. 'I demand you release me this instant! Do you know who my father is? He'll have you all arrested the second he realises I've been kid...' her tirade stopped almost as quickly as it had started. There were two fingers pumping up and down in her slippery wet channel, a mouth and tongue doing a flawless tango on her clit and yet more stimulation as the dildo twisted, turned and pumped mercilessly inside her. Jenny's voice died in her throat. She could not have another orgasm in front of all these people. Not like this. Desperately trying to quell her feelings of intense arousal by thinking of everyday mundane things such as painting her nails, cleaning her teeth or sitting through her French lessons, she reasoned that eventually her body would come back down to earth.

  Mark watched her battle for control with interest. His perceptive glance missed nothing and he was thoroughly enjoying watching her lips as they silently mouthed a decidedly eclectic mix of French vocabulary. The poor lass didn't stand a chance. He had just found her G-spot and was beginning to torment the area with consummate ease. Watching the trainee's body light up like a Christmas tree, Mark stared at her pretty little face as flames of anguish engulfed her. She couldn't lift a finger to stop him and neither could she curb her reaction. To be fair, even the most skilled in restraint would have a hard job resisting the mechanisms he employed.

  'No, no, no,' Jenny whispered, even as her body cried out exactly the opposite. She was fighting her reaction with everything she possessed, but it was like trying to stopper a storm drain with a bath plug - pointless. The floodgates had been opened and the room was filled with her scent. It was the heavy, musky, sweet smell of arousal and it was getting stronger by the second. Her legs were sticky and wet, her body strained against the leather straps and she was already trembling violently.

  Mark's lips stopped his ministrations on her clit to speak. 'We have six inches, Aggie. That'll do.'

  He slipped the dildo smoothly out of her ass with an audible pop and there was a quick scratch of pen on paper before the room went silent once more. Then footsteps; loud, heavy footsteps which she guessed were Henrietta's. The next thing she knew Mark's face was pressed against her ear and he whispered.

  'Do you want to beg for release, horsie?' His words were like a red rag to a bull.

  'Fu...uuuu,' came Jenny's response, which would have been much clearer had Henrietta not just squeezed her jaw open and forced the orange ball securely back in place.

  'We'll have none of that nastiness here, dearie,' said Henriett
a disapprovingly, in her sternest voice.

  Mark laughed and gave the trainee a pointed look. 'I'll take that as a no, shall I? You'll live to regret that decision.'

  Finding a new burst of energy Jenny shook her head, trying to indicate that she would not, but his face had already disappeared once more, disturbingly between her legs. Once again his tongue found her clit and this time he sucked. It produced a much tighter friction than the licking, and the sensation quickly turned to intense pleasure before additional light pressure on her anal passage had her gasping once more. Something else was being forced inside her. Staying completely still, she tried to evade the object by clenching herself as tightly as possible.

  Mark thrust two fingers inside the trainee once more, found the elusive G-spot on the front wall of her vagina and started rubbing enthusiastically. In a few short seconds it achieved the desired effect. She couldn't keep her body tightly clenched when she was on the knife-edge of release. In a single thrust he part pushed, part forced the slippery object inside her. In this particular instance it was a kindness to be quick. Not that she was going to thank him for it.

  Jenny didn't scream. Although the sound bubbled up inside her she forced it back down again, unwilling to give them the satisfaction of hearing it. It hurt. It bloody hurt. Her sphincter was contracting madly around the device, whatever it was and it hurt. That didn't seem to matter though, because the sensation had nearly pushed her over the edge into what promised to be the mother of all orgasms. Her body hummed, throbbed, pulsed and shivered. Just the tiniest touch would send her tumbling. As soon as she thought her body had taken the path of no return, the stimulation stopped. All of it ceased at once. Not a hand, finger or tongue moved. If Jenny had thought denying these three strangers the pleasure of her release would hurt them, she'd had no idea how much it would actually hurt her. Her body trembled helplessly as the agony of sexual frustration overtook every pore. She was unable to hold back a sob of torment and a single tear slid down her cheek. As her chest heaved up and down with the effort needed to draw in breath, she felt her whole body ache with an indescribable pain.