Friday 21st of October
It has been a very busy day at the stables so when Red comes through her door she finds him naked, except for his “decorations”, a yellow ribbons tied around the shaft of his flaccid cock and his hairless balls. He is kneeling in the prescribed position, knees wide apart to display his restrained penis, back straight, head up and hands behind his back. Reds new riding crop is held obediently in his mouth…
Red is wearing her office attire, a smart, stylish business suit, black nylons and 5-inch spike heel court shoes. He can’t help but notice her gorgeous lips curl in a smile, see the self-satisfaction, the triumph in her eyes. He had been reporting to the stables for training for over six months, ever since she had caught him at the window watching her as she was getting changed ready to ride out with Lady Sonia and she still enjoys her superiority over him…
Approaching, she ran her amused eyes over him, eager to find faults to punish. She removes the crop from his lips with a soft chuckle…
“Didn’t I specify pink ribbon today?” she asked.
She did no such thing, but he had long learned never to contradict his ex riding instructor.
“I’m sorry, Madame. I thought I was instructed to wear yellow this week…”
An elegant eyebrow arches as she looks down at him, and waits. Inwardly, he groans. She has had a hard day on horseback and fully intended to take it out on him…
“Please punish your stupid slave, Madame, for not paying attention to his orders…”
“Later!” She smiles happily, as she walks around him, to carry out a brief inspection of his work. The instructions she left required him to thoroughly clean the changing rooms and the showers… The contents of the changing room laundry basket filled with dirty jodhpurs, riding blouses, bras and panties was to be washed, dried, ironed and put away in the proper place. He only just managed to complete all items on the list, although no doubt he spent too long lingering over her sexy lingerie. If Red hadn’t already caught him doing so once already and punished him he would have been unable to resist wrapping her soft satin panties around his cock and bringing himself to orgasm several times… Red is well aware of his weaknesses, though, which is one of the main reasons he is allowed to cum only under her direct supervision. The other main reason is the pleasure she takes out of being in total control of his cock and his sex life, and in denying him any sexual relief. She, of course, like all other ladies in her position is under no such constraints…
His is left on his knees while she ensures that he has carried out all of her instructions. I can hear her spike heels striding around the changing rooms looking for evidence of his sloppiness. Returning, he is relieved to see that Red appears satisfied. Pointing with an elegant, manicured finger, she gives him permission to greet her, and he leans forward as his lips deferentially bow to softly kiss her nylon-covered knee. He can’t help wondering if she is wearing pantyhose or stockings… Even down at her knees, Reds expensive perfume fills his senses, and he gazes down at her spike heels, admiring the arch of her feet.
“Get up slave!”
He stands straight, hands still behind his back, and he tries to look ahead. He can’t help but admire her beautiful, aristocratic face, temptingly close but in reality so far out of his reach. Her haughty eyebrows, cruel shiny red lipstick and condescending eyes taunt my impotence. Despite the pain involved, he feels himself trying to grow hard inside his restrainer. He then awaits her pleasure, looking straight ahead as she pulls at his nipple… Doing his best to keep his body still… Red looks down and sees his attempted erection, contained within its leather and steel restrainer. She reminds him of what he already knows that his penis is hers to command, and that it will remain under lock and key until she decides otherwise. She tells him to kneel down on all fours and raise his bottom high for her. He tenses as the air on his exposed buttocks reminds him of her displeasure, and what is to come… She takes the new riding crop and raises it in the air. He can hear her breath rise and fall at the excitement and pleasure that having him submit to her authority brings. As she becomes wet from the experience, he too can feel the pre-cum well up and drop to the wooden floor, and then feel the sweet pain as she brings the crop down on across his bottom cheeks. He vainly hopes that Red is satisfied, but the lesson is far from being over. She pushes his head to the floor so that his bottom is further upturned and brings the crop down five more times. Not for the first time he realises the strength in her long, slim well-practiced arm exceeds expectations.
Red reaches down and caresses his naked bottom; feeling the heat that her punishment has caused with her cool, smooth hands. She moves behind him and reaches under his bottom to grab his balls. The pain has worked its lesson, and his penis has now lost its cockiness, having been put in its place by her punishment.
“You are learning slave!”
Telling him to rise, she looks at his body and he in turn notice the excitement in her eyes. It is then that he knows that he will soon be licking and sucking on his ex-riding instructors clitoris, or perhaps tonguing her perfect bottom, and this time it is his turn to feel the excitement that thought brings. He holds out the chair for her and she sits, crossing her long, elegant legs as she settles down with the “Horse & Hound” as he pours her a glass of wine and then kneels down by her side, head bowed deferentially. Shortly he is told to collect the items she has listed then go to her changing area and wait there. He kneels in the corner for almost 20 minutes before she arrives. Standing before him, looking down at his sissy image, Red begins to remove her business suit. First she unzips her tight skirt, and as it drops to her feet she kicks it towards him. He picks it up respectfully and softly kisses it before hanging it up in her locker.
Reds blouse follows, although this he places in the laundry basket. Eventually she stands before him dressed just in her spike heels, bra and suspender belt with seamed fully-fashioned stockings. His ex-riding instructor keeps these on to tease him further. She lies back on the bench and orders him to pay homage to her beautiful body, which he eagerly, and gratefully, does…
He begins as usual with the toes of her black court shoes, kissing first, then licking the smooth patent leather. He wraps his tongue around her stiletto heels, then raise himself up her legs, worshipping Reds long, nylon clad limbs. He bows his head and continues upwards, avoiding for the moment her beckoning pussy, gradually working his way, via her belly, up to her breasts. As he sucks the nipples through the restraining bra I hear Red moan softly with pleasure…
He tries not to think of their time as riding instructor and student, when he had a real man’s rights, and sometimes free access to her wonderful body. Not just her part time sissy slave…
Suddenly, she rolls over, sensing that his pleasure has increased beyond a slave’s allowance, and indicates that he is to pleasure her anus. He humbly kisses her bottom, finding his way to the pink puckered hole, working his tongue hard and long into her… She lets out a long sigh of pleasure, and he feels pleasure himself, hearing her moans as he worships her bottom, and feels her body shudder in orgasm. He knows that she currently has several lovers at the stables, but they are all strong men - real men. He is sure that he is the only one fortunate enough, willing enough, to worship her sensitive bottom… But he is so wrong…
She turns round again and pushes him back, telling him to place both his hands behind him. He does this, and she uses handcuffs to lock my hands. Red looks so beautiful and sexy… The tensions of her busy day at the stables here have evaporated as her despised ex-student has tongued her faithfully to orgasm. Now bound, she removes his restrainer, making sure that light brushes with her hands tease his cock as she does it. His cock stands tall under her amused eyes. Then, at last, she removes her bra, freeing her succulent breasts to his gaze. He knows that she gets a kick out of teasing him with them - even if his hands were free, she knows he would not dare to touch her breasts without permission. Red revels in showing him what is no longer his.
Trussed helplessly, she rolls him onto his stomach and slaps his bottom for forgetting it is for her pleasure, not his that he is there. Once, twice, his already reddened firm bottom, soft to her touch, feels the stinging pain of her slaps and begins to turn darker red. She feels a drop of cum roll down her thigh from the intense pleasure spanking her ex-student is giving her. Red then tells him to get up, which isn’t easy, and to stand as she sits at the edge of her bench and then to lower himself over her lap.
Just as he thought the punishment had ended, it begins again, this time the most humiliating, a bare-bottomed spanking over my ex-riding instructors lap. She sees the beads of wetness glisten on the end of his cock as he lay over her knees. His hard cock presses forcefully into the tops of Reds nylons, and his eyes draw level with her high heels… Then she brings down her hand on his bottom with a crack. He reels with a mixture of pain and pleasure, and say “Thank you, Madame,” after every stroke, reaching forward to place a tender kiss on her shoe. He knows how much other men desire his Mistress, and he feels very lucky that he is still allowed to get this close to her. He knows that she has many eager lovers, both men and women, who satisfy her feminine yearnings. Many men lust for his Mistress, but how many men would willingly be in the position he now finds himself, ridiculously be-ribboned, lay across her soft but unyielding lap, accepting her right to spank him. He realises that she no longer considers him a man at all, just her sissy slave.
Suddenly she feels his body shudder, and as she knows her ex-students body so well she knows that he is am cumming. Red demands him to stop, since he was not given permission to cum. Her demands are in vain, he has not been allowed to cum for three weeks and nothing now could stop the torrent building up inside him… His disobedient cock spurts its homage over Reds stocking tops and soft thighs…
He is spanked harder, and then told, “Your disobedience will be dealt with!”
She tells him that he is to make her cum several times before she will “reward” his bottom properly with her new riding crop and as he lays on his back across the bed she straddles his face and he opens his lips and begins to pleasure her…
