Sir Harold Goes Riding

An episode from the ongoing adventures of Sir Harold Pithwinter, Victorian English landowner, local dignitary, magistrate, and general debauchee. All active participants in this saga were over eighteen years of age at the time of the events chronicled here.

Sir Harold's encounters were by no means restricted to the members of his immediate household. Several of the more attractive females amongst his many tenants had been the subjects of his carnal attentions. Attractive, as far as Sir Harold was concerned, simply meant that they were still breathing. He had made it his practice to undertake frequent inspection of the properties on the estate. The inspections were invariably carried out during the working day when the men folk would be hard at labour in the fields or with the livestock. Inspections were normally completed in under an hour or two. This left the recipient safe in the knowledge that her recent full compliance had ensured that she and her family would continue to have a roof over their heads, at least until the next inspection became due. Usually, the target would be the head goodwife of the house, although there were some households where the daughter provided the service. Sir Harold rather enjoyed having the mother watch helplessly as he slipped into her offspring. All about power.

There had only been one occasion where a husband returning at an inappropriate time had interrupted him in his labours. The man was clearly not supposed to be away from his place of work at that time of day and was thus doubly embarrassed by not only being caught out by his employer but also by finding said employer's prick embedded firmly to the hilt in his wife's vagina. The distraught man was made to stand watching while Sir Harold finished and was then subjected to being forced to lick out the cuckold sperm before servicing his wife's back passage. Sir Harold naturally watched the show. The husband's performance was feeble initially but improved dramatically following the liberal application of a well-placed riding crop across the wretched man's bare buttocks. Matrimonial matters were never quite the same following this incident and the couple left the estate, separately, shortly afterwards for the industrial north.

Sir Harold was quite fastidious in record keeping in all matters relating to the estate. This applied particularly to his visits to the tenants. It allowed him to keep track of when his fillies had been serviced and recorded dates for possible impregnation. His father had been far less concerned and as a result Harold could never be quite sure whether or not he was slipping his rod into one of his half-sisters. It didn't bother him in the slightest; a pussy was a pussy after all. The ones that he was reasonably sure of gave an added boost to the proceedings. His probable daughters were yet to come of age so that was not a concern for the present.

Most of the recipients accepted the visits with resignation and succumbed to his demands by offering nothing other than token protest. While not the overwhelming majority, there were some who did actually appreciate the rigorous shafting that a visit from the Squire inevitably brought. These Sir Harold especially rewarded with his favours and earmarked them for use at the main house when he was between servant girls, or his sexual appetites gave rise to a particular requirement.

There were also a few that, while not offering outright refusal, were less than enthusiastic in their commitment to the proceedings. These particular ladies ironically often became Sir Harold's preferred targets. Overcoming the resistance to his advances added a higher degree of spice to the proceedings. He had no fear that any cry of rape would receive a response. That was totally out of the question particularly as he was one of the local magistrates. It was simply that the struggle to overcome and subdue the hapless woman provided an additional thrill and enhanced his erection. As an aid for his visits to these particular tenants he carried a set of sturdy leather straps fitted with brass rings and snap clasps. Each strap was roughly 30cm in length with a brass spring clasp at each end. A brass ring was sewn into the strap, about 5cm from one end.

Before leaving for his day's sport, he prepared the restraints by connecting one clasp into its neighbouring ring. The other end was looped round and then fed through the loop to form a slip noose.

So, all prepared, Sir Harold is out for his day's hunting.....

A flurry of activity occurs in an isolated cottage triggered by the sound of an approaching horse. A young woman nervously answers the insistent rap of the riding crop on the closed door. She is in her early twenties, of medium height with shoulder length chestnut brown hair. The hair while clean and tidy has obviously not been subject to any coiffeur in the discernible past and, other than the simple tie at the back, is unadorned. She wears a simple brown smock that gives a broad hint of the contours hidden beneath. Her breasts, while not overly large, are prominent and obviously moving unhindered as she walks. Age, work, and childbearing have yet to take all her youth although the signs are starting to appear in the lines at her eyes and the roughness of her hands. She has one child so far.

Her breasts retain their youthful pertness despite never having been supported by anything more than a simple breast cloth and the enthusiastic hands of her husband and, of course, Sir Harold. She is not slim but also does not carry any excess level of fat; the flesh can best be described as ample but firm. A pair of well-rounded hips indicates that childbirth would be far less difficult for her than for many others. Her waist still tapers well and reveals, at the present time, only the barest rounding of her belly. Her legs are on the long side but sturdy, flowing into well-formed buttocks containing a crease that is clearly defined as she moves. She is not, in truth, the greatest of beauties, but has all the female requisites, and in the correct quantities to satisfy Sir Harold's current need to deposit his seed deep into a female belly.

A shadow flickers across her face as she recognises the caller and memories of the many previous visits flood back to her. The young son asleep in the cot by the fire is probably the product of a previous encounter, the timing could well be correct for Sir Harold passes this way on a regular basis. She stands, head bowed, awaiting her fate.

"Good afternoon madam and how are we today? Ready for a little more rough riding perhaps?"

Sir Harold leans heavily against the rude wooden door to prevent its closure. The girl backs slowly into the room, her hand going to her mouth as she hisses. "Oh God Sir, not again. Why can't you leave me be?"

"'Tis that time of the month again m'dear. Just look on your little service as being a small part of your dues to wellbeing of the estate."

Sir Harold grabs the girl by her wrist before she can move further away from him into the shadowy interior. As he does so he pulls her towards him, turning her sharply round so that he is positioned behind her. In one swift movement he slips the prepared strap over her left hand and pulls it sharply behind her causing the noose to tighten firmly. His other hand grips her shoulder and then slides down her right arm, pulling it across her back so that both hands can be lashed together by the strap. His well-practised actions are so rapid that the girl has no chance to escape him before the leather carried out its duties. She has experienced this several times previously but is still unable to defend herself against it.

Pressure on the back of her knee forces her to stumble forward. A firm pair of hands stops her from falling completely to the ground. Even so she slides down slowly onto her knees. She gasps as her hands were pulled up high against her shoulder blades. Her palms are moved until pressed together. The leather is quickly looped once around her neck and back over the other shoulder to be clipped to the ring. Any attempt by her to move her arms down will now cause the strap at her throat to tighten, choking her. The reverse prayer position is very effective as a means of restraint as she well remembers. She wisely remains still as a hand comes over her right shoulder and reaches forward to firmly grasp her under the chin.

On some occasions Sir Harold chose to employ a gag on his victim. This was not because he feared interruption; none would dare, but that the muted sounds increased the level of his excitement. He carried two of his favourites with him at all times. The first was a simple ball gag, consisting of a stiff vulcanised rubber ball about 5cm in diameter attached to a thin leather strap.

The second was a much simpler but no less effective bit gag made from a 3cm thick strap of inflexible leather some 12cm in length. Brass rings were sewn at each end to accommodate the snap clasps of the reins. Straps are attached to each end and connected together by a brass buckle at the rear of the head.

It would be the latter device that he plans to use today.

Pressure from fingers and thumb at the base of her jaw force her teeth apart to accommodate the hard leather bit that is roughly inserted into her mouth, restraining her tongue. Her cheeks feel the harsh material as the strap is fed through the buckle and tightened, trapping, and pulling her hair into a painful bunch at the back. The reins are attached to the gag rings and draped over her shoulders in preparation for the coming ride. Strong hands on her shoulders pull her to her feet and guide her towards the rough pine table in the corner of the room. She gasps through her restrained teeth as she is roughly pushed forward to lay prone against the work surface.

The hands leave her for a moment and she hears the sound of clothing being removed behind her. The loud thump of heavy riding boots hitting the earthen floor resound through the tiny hovel. This is soon followed by the far softer sound of a pair of riding breeches being thrown over the three-legged stool by the table.

A hand moves down her leg and draws the material of her smock up and over her buttocks to lay loosely around her waist. The swish of parting air gives her a fraction of a second warning before the riding crop slashes down against her bare cheeks. Even with the gag her cry can be clearly heard. A momentary pause and then the sound of the leather tip slashing downwards again to its soft flesh target.

Sir Harold is a past master at this. He knows, by instinct exactly how long to leave between the blows so as to exact the maximum pain for his victim. Three strokes on each cheek produce six well-defined red wheals standing clearly against the pale flesh. The marks will be obvious for several days, not that Sir Harold cares. The woman's husband will probably not see her unclothed in daylight anyway, and even if he does there is nothing, in practical terms, that he can do about it.

The faint sound of a jar or bottle lid being undone catches her attention. She groans as she realises what is about to happen. She begins to squirm as a knee is inserted between her legs, forcing them apart. The hand on her neck holds her face firmly down against the table. Fingers begin to explore the pussy crack at the top of her legs. They begin to apply some form of lubricant to the still dry lips. She bites deeper into the leather as a stout finger is inserted into her body. It withdraws for a moment and then re-enters deeper than before, down to the second knuckle, then revolving and applying the lubricant to the tunnel walls. Out again and then back in to its fullest depth forcing the passage into accepting the intrusion. She feels involuntary twitch of the anal muscles as the thumb playing across the tight rim is pushed inexorably inwards. Her husband uses that way so regularly that resistance is now minimal. Like many of his compatriots, he needs the regular relief but not the burden of additional mouths.

The finger and thumb begin a rhythmic pincer movement like the claws of a crab closing in on its prey, rubbing through the thin inner wall. Several minutes pass and the damp grows as her body instinctively begins to produce its own lubrication in response to the familiar movement. Her muscles begin to lose their strength to resist. The hand moves back slightly and then forwards to the full flesh of her mound. The fingers pull at the pubic hairs and the cupped palm massages the sensitive flesh, sliding from front to rear with increasing rapidity. The forefinger slides smoothly through the now well-lubricated crack and pushes hard against the swelling clitoris. The rotation of the finger against her sensitive flesh makes her gasp. Her hips begin to buck gently in time with the familiar movement as her body betrays her and the remaining inner resolve begins to evaporate.

A pause as the hand is moved away, followed by the sensation of something larger and hotter being rubbed against her secret spot, seeking an entrance. The prepared lips part easily now to allow Sir Harold's rigid member to pass through the gateway and drive down along the passage to the inner sanctum. One impatient thrust takes him to his full depth. She screams angrily into the gag as the tool's head hammers against the mouth of her womb and forces its way inwards.

Sir Harold pauses for a moment to feel the tight hot cunt walls enclosing his rod. A small shudder passes through her as he begins to withdraw. A second scream, not so harsh this time, disappears into the leather as her passage concedes to the insistent re-entry. He pulls the reins on the gag sharply, jerking her head back towards him. Time to start properly riding the helpless mare below him.

"Now then m'dear time to get another one set in there I think. Need to get those lovely bags of yours full of milk again don't we? Got to have something warm to coat my hands in when I come over in winter."

She shuddered at the memory of Sir Harold milking her, as she milked the cow in the yard. He had forced her to kneel on all fours on the table while his strong hands pummelled her engorged flesh to draw the white fluid from her breasts into the large wooden bowl beneath her. The squeezing and pulling only ceased once he had drained her completely on both sides. She had initially cried at the thought of her son going hungry that evening, but Sir Harold at least had the common decency to leave most of the supply. Indeed he stayed to watch her spoon the now cooling liquid into the tiny mouth. This new activity became an integral part of his visits, which increased considerably in frequency while her milk was in. During these visits he altered his usual entry point and invariably took her in her anal passage. The usual position was for her to lean forward with both hands resting on the table; legs spread wide so that he could enter her at will and simultaneously continue with his hand milking; her ankles and wrists firmly tied to the legs of the table.

The memory fades as she feels the cock inside her working its way into the sides of her tunnel. Left, then right; upper and lower. She knows that all sides of her inner belly will be stretched by the pistoning rod into her. She remembers this more than anything. Her husband just fucks her straight in and out a bit and comes. Sir Harold takes his time and works away reaming at her inner belly.

Her cries begin to change to deep moans as the speed his rhythm increases. The penetrations are now full and deep. She feels the ache building deep inside her. The rein draws tight, pulling her head back and upwards to give a graceful arch to her neck. With every stroke the heat in her body increases as her juices commence their inevitable flow. His left hand moves down to lift her leg up from the floor so that the knee is now resting on the tabletop. Thus, skewered against the family food board, one knee held high, head held firm in the grip of the reins, she is totally open and available, ready to be ridden hard like the trained filly that she has rapidly become.

His speed increases. She feels the tugging as the master's hand reaches down to grasp the long hair that rests against the nape of her neck. She cries again as her head is pulled sharply further back; the hair now fully entwined between his fingers and the rein. The ache builds and starts to flow out of her.

His hips continue to bounce hard and fast, slapping against her spread buttocks as he approaches his climax. With one great lunge he sends forth the first batch of his seed deep into her. He drops forward onto her back, pulls her hair to one side and sucks viciously at the skin of her neck. She screams at the pain but is powerless to resist. The marks will be with her for days but hidden by her crowning glory. The ache finally flows over her completely and she is engulfed by the heat.

Sir Harold's arse continues rise and fall for a few strokes more as he bites and injects the remainder of his seed into the quivering body.

The spasms decrease slowly down to nothing. Heavy breathing and a few soft whimpers from the tabletop are all that punctuate the silence of the room. The child in the crib is still asleep despite the noise.

The neck straps are released and the hot weight lifts from her back. She feels the gag being removed none too gently. He withdraws his cock slowly until just the head remains. A deft couple of strokes assisted by well-practiced finger action along the tube extract the remainder of the white fluid into her collapsing tunnel. The final few drops are deposited on the walls of her cheeks as he wipes himself clean. He inspects his handiwork, grins, and nods his head in satisfaction.

"Best you get a fill of that seed from your man in a couple of days; just so there is no cause for debate."

At her rear she can feel the warmth beginning to trickle out of her and down the inside of her leg but makes no attempt to stop it. The thought of the crop and the memory of a previous afternoon's mistake are sufficient deterrent. She knows without looking that he will be standing watching the white stream flow over the contours of her leg.

"Well then m'dear, I'll take m'leave of you, until the next time I'm riding over this way. Won't be too long I expect, so don't you fret too much"

The door swings to and she is alone with just her pain and a soft dripping sound.