Lady Ravensdale and the Highwayman

The man continued to fondle the inside of her cunt and moved to and fro to massage her clitoris all the while circling inwards on her anal aperture until it slowly yielded to the piercing of his tongue. Gently he penetrated the forbidden orifice. Annabelle's breathing was coming quick and fast, adrenaline was pumping around her body, she had never felt more vibrant. The man continued to gently rub her clit producing the most exquisite tingling sensations in her loins. His other hand moved to insert two fingers into her dripping pussy coating them liberally with the mixture of female juices and male spunk which were still dripping from her slit. Now his fingers moved upwards, one finger was now circling her anus, this time coating the star-shaped opening with lubricating slime. Annabelle began to intimate what might be coming next and flinched slightly as the man's index finger probed her most intimate opening. The tight little ring of her sphincter yielded to his probings and he inserted first the tip and gradually all of the finger spreading more lubricant juice around the interior of her rectum. Slowly her tight anus relaxed and allowed the man to move his finger within the little aperture. After a few minutes the first finger was followed by a second, coating her with more juices and distending the puckered opening still further.

Annabelle knew now with some certainty that the man was preparing to sodomise her. She remembered how Lord Kempston had unsuccessfully tried to penetrate her anally. She had heard whisperings of the doings of 'nancy boys' and 'buggeradoes' and accepted that perhaps some men might indulge in such unnatural forms of pleasure but she could not believe that a gentleman would wish to avail himself of lady's backdoor when she could offer a front entrance expressly designed for the purpose. Besides she was sure that a gentleman's organ could not fit into a lady's delicate little bottom. After all Lord Kempston's attempt to penetrate her in this way had ended in failure.

Such thoughts were, however, soon pushed from Annabelle's mind as the highwayman continued to stimulate her engorged clit all the while probing further and further into her anal cavity with his fingers. Annabelle knew that she did not want this to stop. What the man was doing to her was utterly wrong; he had no right to use her body in such a vile way but somehow she now craved the pleasure that he offered. His nimble fingers were producing exquisite waves of ecstasy such as she had never before experienced with a man. What had she been missing out on all her life?

Suddenly the highwayman withdrew his finger from her rectum and shifted his position. He knelt behind her and Annabelle felt something much larger than a finger probing the cleft between her buttocks. It became readily apparent to Annabelle that what she had feared was about to come to pass, she was about to be buggered. She felt the head of the man's organ probing obscenely at the tightly puckered opening of her anus. It felt so much larger than his delicate fingers to which her sphincter had so recently yielded. Surely so large an organ could not pass through such a narrow aperture.

Now the man applied more pressure and Annabelle could feel the crinkled skin around the tiny brown hole stretch as the crimson head of his manhood began to inexorably invade her. At first it seemed the assailant would not penetrate her postern gate. Annabelle clenched her muscles in fear and repelled the assault.

"Madam, do not be afraid," said the highwayman. "I have no wish to cause you pain. I can see that you have never received a gentleman in this manner before. I can assure you that do you but relax a little you may have the opportunity of a new pleasure to which you have been so far unaccustomed."

At first Annabelle was shocked. How could this fellow who was about to ravish her virgin anus speak of 'a new pleasure'. However, on further consideration Lady Ravensdale realised that the prospect of losing her anal virginity was more than a little exciting. She also realised that the whole act was likely to be more pleasurable if she acceded to the man's demands rather than putting up further resistance.

Annabelle tried hard to relax her sphincter muscles and nervous as she was her tight little ring yielded slightly to the pressure of the highwayman's manhood. Suddenly the engorged purple head of his manhood had slid past the constricted aperture and lodged in her rectum. To Annabelle's surprise the man did not push forward his advantage. Instead he murmured in her ear.

"That will be very tight my lady. Pray take a moment to adjust yourself before we proceed."

Indeed Anabelle's little anal sphincter had never before been so cruelly distended as by the invasion of this monstrous organ. She felt stretched yet also intensely excited; for the first time in her life she had a man's organ in her back passage. It felt so wanton. After a few moments she began to become accustomed to the feeling of fullness in her rear and even yearned for her ravisher to penetrate her further.

The highwayman perhaps sensed her willingness to proceed and began to thrust himself forward but with infinite gentleness for a would-be ravisher. He merely moved the tip of his cock to and for within Lady Ravensdale's tight rectum. Even these tiny thrusts were painful at first but Annabelle also felt an exquisite thrill as her forbidden orifice was probed by the swelling organ of this stranger. Fortunately the highwayman had lubricated her little cavity well and although it was a tight fit his organ was able to slide its way forward bit by bit. Annabelle had expected the man to brutally thrust himself into her and to then mercilessly ravish her anally but he appeared to have enough patience to take his time. Once or twice she gasped in pain as his manhood invaded her bowels deeper and deeper. However, at the same time the delicious and wicked sense of being taken and filled by a man's meat excited Annabelle beyond measure. This man exuded such strength and power and a degree of control which Annabelle had never experienced before, despite the fact that her husband had been a member of Britain's ruling class.

By degrees the highwayman inched his cock into her rectum until at last his considerable rod was fully embedded in Annabelle's stinging rectum, Annabelle could even feel the hairy sac of his balls stroking against the cheeks of her buttocks. Now he pulled back and began to deliver longer strokes into Annabelle's reddened anus. His thrusts were slow and measured. The man was in control he seemed to know exactly what he was doing. The other two highwaymen stared open mouthed as they watched this English lady totally at the mercy of their leader. However, Annabelle and the highwayman were in their own private world oblivious of the stares of the two men and intent only on their own pleasure. Suddenly the highwayman reached forward and his fingers brushed Annabelle's clitoris. She gasped as a shock of pleasure ran from the engorged little organ through her loins. Once again the man found her clit and began to gentle stroke it as he continued his long slow thrusts into her rear entry. The pleasure for Annabelle was exquisite. The pain and discomfort of her sore and stretched anus faded into the background as her twin sources of pleasure brought her to increasing heights. Soon she was moaning in delight as the caresses on her clitoris raised her nearer and nearer to climax.

The highwayman now began to thrust more quickly and firmly into Annabelle. All restraint and gentleness were abandoned and at last Annabelle felt that she was being truly anally ravished. However, she was past caring. Anabelle at last realised that she could only find true pleasure in completely debauching herself. She had left behind the genteel aristocratic lady and knew that after this day she would in some way be a different person. However, of all this Annabelle was only dimly aware for at the centre of her consciousness were the rising waves of pleasure radiating outward from her clitoris and her anus. Her cries were no longer muffled, she could no longer restrain herself and now openly begged the highwayman.

"Oh please take me, make me yours," she cried.

"What is it you wish me to do my lady?" grunted the highwaymen still thrusting the full length of his cock up Annabelle's arsehole.

"Take me, ravish me!" screamed Annabelle.

"Say it my lady. Tell me you want me to fuck your arse," insisted the man.

"Very well, please fuck my arse," retorted Annabelle.

"With pleasure ma'am," replied the highwayman.

Once more her ravisher plunged his weapon into her now reddened and gaping arsehole. He plundered her open rectum with renewed force and feverishly rubbed her clit. Annabelle had never been fucked with such passion and force. However, she had also never experienced the sensations which were now running through her body. She knew that some women climaxed when making love and now realised that this was what she was experiencing herself. Higher and higher she rose on a wave of pleasure until she could hardly bear it then suddenly pure ecstasy exploded in her whole body, Fireworks went off in her head. How was it possible that she had gone all these years and had never achieved such rapture.

The highwayman was also approaching his own climax realising that Annabelle was in the throes of an intense orgasm he left off his clitoral stimulation and concentrated on taking his own pleasure. While the lady's arse had opened up nicely it was still sufficiently tight to exercise a firm grip on his throbbing member. Each time the head passed the tight muscle of her sphincter it was tightly rubbed achieving a throb of pleasure. Truly this exquisite sensation could only be achieved when sodomising a woman. The highwayman repeatedly stabbed his weapon into the close sheath of Annabelle's rectum. He too felt intense waves of pleasure as his come built in his balls. Soon he knew his orgasm was imminent. The beautiful woman beneath him, naked from the waist down, was still writhing in pleasure and he delighted to watch his own engorged member repeatedly plunging into the crevice between her deliciously plump and rounded arse cheeks sinking to its hilt into her tautly stretched rear entrance. What a delight to anally debauch such a beautiful and aristocratic lady and to see her actually enjoying the act. These thoughts combined with the delightful sensations running through his cock meant that the highwayman could hold back no longer, with a rush his seed erupted from his balls and gushed from the tip of his throbbing pole filling Lady Ravensdale's bowels with sticky cream. Wave after wave of semen gushed forth as he continued to thrust deeply into her until he had squeezed the last drop of pleasure from the act.

For a moment the two figures remained still. The highwayman still crouched over the lady kneeling on all fours his softening manhood still embedded in her anus. The Scotsman and the boy continued to watch the scene in silence. After a moment the highwayman stood up and pulled up his breeches. Gallantly he offered Annabelle his hand and helped her to stand. He smoothed out her clothes, helped her into a chair and ordered the boy to bring her a glass of wine that she might refresh herself.

As for Annabelle she was in a state of shock but coming to her senses realised what had just happened. The boy thrust a beaker of wine into her hand and she drank it gratefully. Annabelle suddenly realised that her servants were next door and focused her mind on their welfare. She seized the hand of the highwaymen's leader.

"Sir, now you have had your way with me please let me and my servants go," she said. "I swear to you that if you release us unharmed I will say nothing of tonight's events to the authorities.."

"You swear this to me on all that is holy to you madam?" asked the highwayman.

"Oh indeed I do," gasped Annabelle.

"Very well but know this. Should you break this oath I shall hunt you down and kill you," replied the highwayman. Moreover, the world shall know that Lady Ravensdale is a strumpet and a whore who begged for more when she was sodomised by highway robbers."

At that moment George and Mary were bundled back into the room by the two other robbers. Mary fell at her mistress's feet.

"Oh Madam, what have these villains done to you. I swear I will kill them myself if they have harmed a hair on your head."

"Fear not, dear Mary," said Lady Ravensdale reassuringly. These gentlemen have done me no harm. It has but taken me a little time to convince them that we have nothing worth stealing. They have promised to release us on my oath that we speak nothing of what has passed here today. You and George must also so swear."

At that George and Mary promised with some reluctance to remain silent about the night's events. Soon they were bundled back into the coach and driven back to the road through the darkness of the forest. Once on the main turnpike the robbers vanished having melted away into the darkness of the forest.

After more hours of driving through the darkness Annabelle and her two servants at last reached the outskirts of London and found their way to her sister's house. It was late at night but her sister Caroline and her husband Henry had waited up for them, having expected their arrival hours earlier. After some supper Caroline showed Annabelle to her room and she was at last able to rest after a long and arduous day.

Chapter 5: Annabelle encounters the highwayman again

Of the events on the road Annabelle did not speak to her sister and brother-in-law. This was partly because of her oath to the highwayman and partly out of a secret sense of shame at what had happened to her and more importantly the extent to which it had given her pleasure.

In the weeks that followed Annabelle settled into her new life. After the large house and open space of her husband's northern estate Annabelle found the London townhouse small and restricted. To even take a walk she had to navigate muddy and smelly streets to reach any green open spaces. More importantly she was no longer the lady of the house and in charge of her own affairs but reduced to the status of a female companion to her sister.

Annabelle found solace in a new secret life. In her bed at night and in private moments she reflected on the events in the hut in the forest. The way in which the leader of the highwayman had forced her to commit that most lewd and depraved of all sexual acts appalled her but never failed to arouse excitement in her. Annabelle would lie in her bed and remember each moment of that encounter. When she had tried to arouse herself to climax in the past she had failed but now she secretly rubbed herself between in legs beneath the sheets while fantasising about being anally penetrated, this never failed to bring her to a quivering orgasm. Soon Annabelle added a new variation to her nightly activities. She had a silver hairbrush with a long handle, Annabelle soon adapted this as a dildo inserting it at first into her vagina as she caressed her own clit. Soon she plucked up the courage to insert the hairbrush handle into her anus, assisted by the lubrication of some of her cold cream. The thrill of committing such a forbidden act aroused Annabelle intensely and each night she would dream of being sodomised as she brought herself to a pinnacle of exquisite pleasure.

After some months Annabelle had settled into her new life. She found her new station demeaning and she though her sister's life tedious. She seemed to occupy herself with playing cards and drinking tea with her lady friends who Annabelle found empty headed and frivolous. Caroline's husband Henry was even more insupportable. He was arrogant and boorish and appeared to have the lowest opinion of women and clearly resented Annabelle's presence in the household.

One day Henry came home and was sitting in the parlour smoking his noxious pipe and telling Caroline of his activities that day.

"I heard in the coffee house that that infernal rogue and highway robber Captain Ackroyd has been captured at last," said Henry. "Apparently his two accomplices were taken along with him. Hanging is too good for these villains, they should bring back drawing and quartering like the old days."

"But wasn't that only used on traitors?" said Annabelle who had a good knowledge of English history.

"And what you know about it madam?" said Henry in his usual oafish manner.

At that Annabelle held her tongue but pondered on whether it could be a coincidence that three highway robbers had just been captured and she too had been attacked by three highwaymen.

Annabelle had almost forgotten about this incident when some weeks later Henry made another announcement.

"Remember those highwaymen I mentioned some time ago, well it appears they are all to hang and good riddance too. My good friend Jeffrey Jones has rented a balcony overlooking Tyburn and has invited me along, so I think I shall go along next week and watch the buggers swing."

"That will be nice for you dear," said Caroline in her dutiful way.

"You mean you will go along and take pleasure in the torment of your fellow human beings?" burst out Annabelle before she could restrain herself.

"We would all be murdered in our beds and our homes ransacked if the threat of the rope were not there to deter these villains," growled Henry.

Annabelle realised that further argument was useless and relapsed into silence.

Once again Annabelle pondered on the identity of the condemned men mentioned by Henry. Could they really be the same gang who had attacked her? If so part of her was pleased that they should be punished. However, another part of her realised that the events of that night had unleashed a secret passion in her which might never have come to the surface but for their actions.

Annabelle was even more surprised when the next day the footman brought her a letter. She broke open the seal and examined the contents. The letter was headed Newgate Prison, 28th November 1720.

My dear Lady Ravensdale

I must crave your pardon for intruding once more upon your life. It was I who with my confederates detained you on your journey down the Great North Road some months ago. I now stand convicted of my crimes and I must pay for them with my life within the week. I crave your indulgence to a man about to die and ask of you but the boon of a visit to me in prison. Before I die I would like to acquaint you a little with my history that you may better come to an understanding of my actions. I may have deluded myself but I felt that in our brief acquaintance I formed some kind of bond with yourself. If you to have any kind of sensibility of this I now pray that you meet me this last time.

I remain your most humble and obedient servant.

Richard Ackroyd (Capt.)

Annabelle remained staring at the letter immobile for some minutes. She re-read it several times to be sure her eyes had not deceived her. But no, the meaning was quite plain, the man who had ravished her now wanted her to visit him in prison before he was hanged. The impudence of the fellow! How dare he intrude once more into her life now she had pushed the whole unpleasant incident to the back of her mind.

All these thoughts rushed through Annabelle's mind but no sooner had she considered the matter from this angle than she was forced to reconsider. Had she really banished the incident from her thoughts? If so why did she fantasise night after night about being sodomised? Why was she now able to bring herself to climax each night as she pleasured herself with fingers and hairbrush handle? No, this man had unlocked some kind of door in her. He had unleashed a potential which she had previously been unable to access and perhaps for that she was in some way in his debt.