The Highwayman
by Doghead_2000
Copyright© 2025 by Doghead_2000
Erotica Sex Story: A former footman turned highwayman, orchestrates a heist on a carriage carrying Lady DeBear and her twin daughters and things become more spicy...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Mult NonConsensual Rape Incest Sister Humiliation Rough Sadistic Anal Sex Masturbation Oral Sex Petting Pregnancy Voyeurism Size .
As the midday sun started to wane and the temperatures dropped to a more comfortable level, the three men in the shadows of the trees prepared themselves for the afternoon’s business. Jack Black had been a Highwayman for these last fifteen years. He was in service as a footman as a lad and came into contact with many of the gentry from the big families. His rugged blonde good looks and healthy physique had made him a special favorite of the ladies. He had bedded many a so-called lady while their husbands were away.
Of course, the unmarried daughters of their lordships were his favorites. Young, nubile, and chaperoned around men of their own class, they were usually wild in the hay when he got the chance to get them alone and out of the house.
Many a daughter had been married off quickly or sent to a convent a couple of months later, after he had knocked them up with his virile cock. The shame of being made pregnant by a servant always kept the girls quiet about who the father was, though, and they tried to pass on the blame to some young lord or other.
Sadly, this good life had ended one day when one of his lordships had returned home unexpectedly to find him bedding her ladyship in her chamber. He had been beaten nearly to death by the master of the house and his guests and left for dead in a bloody pulp in the roadway.
After that, he could never again work in service. Once the story got around, he was personally ostracized by the gentry. Besides the scars he carried on his face from that incident, they had removed his good looks for all time, and no one would want to hire a man with an ugly face to be around their families.
So now aged forty, he made a sort of living on the King’s Highway as a Highwayman, robbing the rich to give to himself. His two helpers were other men of the road who would assist men like him for payment or a cut of the spoils. They were more muscle than brains and incapable of planning heists on their own, but useful to have around to protect one’s back.
He had spent weeks planning this particular heist, and paid out a small fortune for information on the movements of the family involved from servants and family retainers. Lord DeBear and his family always moved from their family estate in London every summer to their summer home in the rolling hills of Kent. His Lordship always made the journey a couple of weeks before the rest of the family, taking the majority of servants with him, along with wagon loads of the possessions that they would need for the summer months.
Once the house had been cleaned and prepared, the rest of the family, his wife and two daughters, would join him, traveling light in a carriage with just their personal clothes and jewel collections. It was this carriage that he was waiting for, in the trees where the road passed through the forest. He was on one side of the road in the trees while his two colleagues were waiting in the foliage on the other side. Their horses were tethered to fallen branches enabling them to graze, although they were still carrying the highwaymen’s equipment ready for immediate mounting.
Finally, the sound of an approaching carriage could be heard through the trees and the men mounted up and got into position. As the carriage drew level, the three men rode out of their hiding places and onto the road. One of the men blocked the track in front of the carriages’ lead horses, while Jack and the other man approached from different sides, level with the driver and coachman sitting on top of the vehicle. All three men had two cocked pistols at the ready and masks covering their faces.
“Stand and Deliver.” Jack shouted at the top of his voice, and at the same time, fired one of his pistols into the air for effect. The carriage driver pulled up sharply on the reins to avoid a collision as the footman reached for a large old blunderbuss weapon under his seat. The man on the other side of the carriage fired one of his pistols at the man, who was hit in the shoulder. As the large lead ball smashed into his body, the man was propelled backwards off the carriage running board, to lie moaning in the dirt on the ground.
The driver was ordered off the carriage, and while Jack and the other man at the side covered both the two men and the carriage doors, the third highwayman approached, dismounted, and tied up the driver and footman to a tree. Once the servants were well and truly secured and gagged, the three highwaymen turned their full attention to the carriage itself. Ordering the occupants to get out with their hands in clear view, while they covered the doors with their pistols in case of any surprises.
The first to get out was the Lady Elisabeth DeBear herself. An attractive woman aged about thirty-six in a long red wig. She had on a high-necked black long-sleeved dress, drawn in to a slim waist, with pearl buttons from the neck down to her waist.
As she stepped down from the carriage, the men caught a glimpse of her black calf-length lace-up boots and a flash of white silk stockings on a pair of shapely legs. Her face looked strangely familiar to Jack, but this was not unusual, as he had met a lot of the gentry at one time or another during his years in service. The woman was made to stand at the rear of the coach while the other occupants disembarked.
The next person out of the carriage was a striking blonde girl aged eighteen; Mary DeBear was wearing a colorful shiny green silk gown with a low-cut neckline that showed the top half of her beautifully formed large breasts. The gown had a slim corseted waist and a small bustle over the girl’s derriere.
As she stepped down out of the carriage, the men were able to see her small black lace-up ankle boots, over white silk stockings, covering a pair of legs to equal that of her mother’s. A tantalizing flash of the frilled bottoms of her pantaloons drawn over her stockings was also caught as her dress rose up slightly when it caught on the carriage’s step. She had the pretty innocent face of an angel, and yet the look in her eyes was that of a highly sexually mature woman. She was led to stand at the side of her mother at the rear of the carriage.
The third female to get out of the carriage door made the highwaymen take a second double take with their eyes. She was identical in absolutely every way to Mary DeBear. Only the fact that she was wearing an identical-cut blue dress could tell the two girls apart. Anne DeBear was the eighteen-year-old twin sister of Mary. She was also led over to the other two females at the rear of the carriage. The girls’ resemblance was even more striking when you saw them both together.
When no one else disembarked from the carriage, the men cautiously inspected the insides to make certain it was completely empty. Once they were sure that the coast was clear, they climbed up on top of the carriage and started to throw down the traveling chests secured to the roof. While his men searched the inside of the carriage and got the luggage down, Jack covered the three women with his pistols. He still had that strong feeling that he should recognize the face of the Lady DeBear.
“There’s nothing here!” Jack swung around at the shout from the two men who had broken the locks off of the chests. Women’s undergarments and night clothes were spread out around the chests. “There are no bloody jewels.”
Jack ordered them to check for false bottoms and ransack the coach for secret compartments where the women’s jewels might be hidden. Turning to the women, he waved his pistols at them and demanded to know where their jewel boxes were.
The Lady Elisabeth answered, saying that her husband had insisted on taking them with him this year. All they had with them were the small necklaces that they were wearing for the journey and the rings that they were wearing. If that were the case, he was well and truly out of pocket on this robbery. What the women had on would not really cover the other two men’s share, and he would still be out on the cash he had used to gather information and to bribe the family servants.
The two men were annoyed at not finding any of the jewels; they had practically ripped the carriage apart to its shell. Seats and panels were scattered all over the roadway. As they returned to Jack and the three women, they were not in any mood to be messed about any further.
Jack ordered the women to hand over their purses, necklaces, and rings, which they quickly did, realizing that the situation was getting more dangerous by the minute. Handing the small amount of booty to one of the men, he told them to take the spoils and any of the valuable silks in the chests to sell and make their getaway.
The men rummaged through the clothing and selected the more valuable items with a resale value and stuffed them into a couple of nightdresses as sacks. The men were still not satisfied with their hoard, though; the three women were wearing the most valuable silk dresses. They went back to Jack and insisted that they had the women’s dresses as well.
Jack ordered the three frightened women to take off their dresses and hand them over. Reluctantly, the three females started to comply, helping each other to undo the ties and studs. All three realized that they were in no position to object at this point, and their very future depended on them complying without any hesitation.
The men greedily snatched up the three discarded silk garments and stuffed them into their makeshift sacks, all the time eyeing up the three gorgeous women now dressed only in their white stockings, pantaloons, vests, and waist corsets. After whispering to each other for a moment, they demanded more in payment: the women themselves.
This was not the way that Jack had intended things to go, but he was in an awkward position, with the men having three loaded pistols between them to his one. If he objected, the men could turn against him; they were in no mood to sit and discuss things sensibly. If a confrontation did erupt, he could very well be the loser, and the men would have the females anyway. Studying the three women in front of him, he made a decision.
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