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K R I S T E N' S C O L L E C T I O N
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The Highwayman
by Doghead_2000 (doghead_2000@dizzydoggie.org)
***
The robbery went badly wrong for Jack Black the
Highwayman this time, but at least he left the scene
with a big smile on his face and some interesting
memories. MFF, inc, nc, rp, v, oral, bd, preg)
***
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 in contact with many of the
gentry from the big families. His rugged blonde good
looks and healthy physic had made him a special
favourite 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 favourites. 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 unexpected 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 ostracised by
the gentry. Besides the scars he carried on his face
from that incident 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
Kings 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 ones 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, travelling 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 firing one of his pistols
into the air for effect. The carriage driver pulled up
sharply on the reigns 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 of 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 the other 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
colourful 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 mothers. A tantalising flash of the frilled
bottoms of her pantaloon draws over her stockings was
also caught as her dress rose up slightly when it
caught on the carriages 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 travelling 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 recognise the face of the Lady
DeBear.
"There's nothing here!" Jack swung around at the shout
from the two men who had broke 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 were
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, realising
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 though 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 realised 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 discus 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.
He told the men that the Lady Elisabeth was theirs, to
do with, as they will, as long as they tied up the two
younger girls to the wheels of the carriage and gagged
them. With the older woman being still a very
attractive female, especially as she was now, displayed
in her undergarments, the men didn't put up much in the
way of any objections.
While Jack covered the older female, the two men used
strips of torn cloth from the discarded clothing on the
ground to gag the two twins. They were each stood
leaning against one of the carriage wheels and their
arms were lashed to the top of the wheel rim in about
three places. Their ankles were also bound to the
bottom of the wheel rims about two feet apart.
Satisfied at their handiwork the men turned their
attention again on the older woman. Jack put away his
pistols and sat back against a large tree and dug out
his clay pipe for a smoke. While relaxing, he watched
the two men and their captive, throwing an occasional
glance across at the two bound girls.
The men gagged and tied Elisabeth's hands together in
front of her and dragged her into a small clearing at
the side of the road, in clear view of Jack and the two
girls. Selecting a thick branch about seven feet off
the ground they tied her hands to the overhead branch
so that her feet were just resting on the ground. With
her arms outstretched her ample breasts were forced
upwards and outwards making them look even larger to
the men's eyes.
They tore off her silk vest to get a better look, and
then started to grope at her breasts, kneading the
flesh and squeezing her large brown nipples until they
hurt, her whimpers into the gag went unheeded by the
men as they got to know her body more intimately.
Next came her silk pantaloon draws, the men pulled them
out from under the waistband of her corset, and tugged
them down until they were below her knees. She made a
really erotic sight like this; her body was still firm
and attractive. There was no sign of the childbirth of
the twins eighteen years ago, and her husband had never
been able to give her any more children.
She was now hanging there, white silk stockings from
her ankles to just above her knees, a waist corset from
her waist to just under her ballooning bosoms and her
draws down around her calves. Her arse was shapely and
taught, and the neat brown patch at the junction of the
top of her legs was trimmed and inviting.
The men savoured the sight of the defenceless woman for
a few moments before stepping forward again and letting
their hands once again rove over her body at will.
While one of them explored around her pubic triangle,
teasing the very top of her thighs apart to gaze at the
hidden treasure hidden in there, then using his fingers
to rub the revealed lips and bud.
The other man kneaded the flesh of her shapely
buttocks, spreading the valley between them and teased
the tight little opening of her anus with a finger.
They switched places and their manipulations got
rougher as they worked themselves up to a frenzy of
sexual excitement at her expense.
Unable to restrain themselves any more, the two men cut
her down from the tree and ripped her draws completely
off. They then threw her down over a fallen tree trunk,
face upwards. While one of the men held her arms up
above her head on one side of the trunk, the other
grabbed her knees and held them apart as he sunk his
engorged cock deep into her pussy.
He rutted into her like an animal on heat, no finesse,
just pure animal lust as he pumped his hips backwards
and forwards to ram his cock into her cunt. It didn't
take long to spew his load into the woman's abused
twat, and they swapped positions so that the second man
could rape the ladies cunt. The sex, if you could call
it that? only lasted a few minutes before the man also
emptied his balls into the woman's slippery cunt.
Elisabeth thought the rape was over as the two men
started to lift her up off the tree trunk, but as she
stood back up on her two feet, she was pushed forwards
onto the trunk again, this time face down. One of the
men again grabbed her arms and kept them stretched out
in front of her, as the other man knelt between her
legs again.
Lady Elisabeth realised what was about to happen to
her, but couldn't believe that anyone could even
consider such a thing, she had never had anyone even
consider having anal sex with her, the very idea of if
was sickening and revolting, besides there was no way a
man could possibly even enter her there, her hole would
be just to small. Of course she was wrong.
She started to scream in hysterics into her gag as the
first man placed the head of his cock against her
virgin arsehole. The screams changed to ones of shear
agony as he started to force the head inside her and
kept pushing. When the head was through her portal, he
rammed the full length of his shaft home, deep into her
insides and started to fuck her stretched arse with
gusto.
He pumped her butt until he spewed his seed into her
bowels, and then held her down so that the other man
could sodomise her ravaged anus as well. When both men
had satisfied their carnal lust on her used and ravaged
body, they allowed her up and marched her back over to
the carriage, where they tied her up to one of the
wheels on the other side of the vehicle. Nodding a curt
farewell to Jack, they picked up their booty, mounted
their horses and rode away.
Jack sat there for a few minutes, going over the scene
he had witnessed in his mind, while watching the two
younger girls tied to the carriage. The girls had also
been watching their mother's rape and buggery, and
although they found the events to be both sickening and
frightening, they had both found the sight of their
mother being stripped and ravished by the cocks of two
big men to be strangely erotic.
Slowly Jack got up and crossed over to the two girls,
standing between the two wheels and without saying
anything, he gently cupped a breast of each of the
girls through their silk vests. He tenderly kissed one
of the girls on the forehead and then the other as he
very gently tweaked the nipples on the cupped breasts
through the silk. The girls could not understand why,
but they trusted this strange masked man not to hurt
them, even after what they had witnessed with their
poor mother, but for some reason they did.
Jack continued to stroke their breasts and going from
one to the other with little pecks of his lips on their
cheeks, necks and even their eyes, and the girl's
bodies responded to his touch. Finally letting go of
both girls he gently ripped open the top of each girl's
vests and rained gentle kisses onto their breasts and
erect nipples, sharing his time with equal attention to
both girls. And then while kissing one girls breasts,
he used his hands to free up the waistband of her
pantaloons and let them drop. Without touching the girl
below the waist, he crossed over to the second girls'
breasts and again gently dropped her draws while he
kissed her swollen nipples.
Before going back to stand between the girls again, he
noticed that each of the two girls had a large
identical horseshoe shaped birthmark at the top of
their right inner thighs, Jack again went and stood in
the middle of the two girls, fondling both their
breasts, and then slowly allowed his hands to drop down
past their waists to the mound of blonde hair nestling
between their perfect legs. He gentle rubbed the palm
of his hands over their pubic mounds, as he did so both
girls pushed their bushes forwards to meet him.
He let go of one of the girls and knelt in front of
her, as he moved his mouth to the soft centre beneath
her bush of hair and started to kiss the tender lips he
found there, she forced her hips forwards to grind
herself against his mouth, He kept the fingers of his
other hand on the other girls mound and started to
gently stroke her lower, between her legs. After a few
minutes he changed position and started to use his
mouth on the second girl while still manipulating the
other with his fingers.
All of a sudden he stopped touching the girls, except
to place another gentle kiss on their foreheads. He
took his knife from his belt and gently cut through the
bindings of one of the girl's ankles, as she closed her
legs to stand more upright, her draws slipped down to
her feet, and she stepped out of them. Jack then cut
the other girls leg restraints and she too stepped out
of her draws. Still without saying a word he untied the
gags on the two girls, kissing each on the lips as he
did so. When both girls were free of their gags, he cut
through the bonds on their arms to release them from
the wheels completely.
Still with none of them saying a word, Jack took each
of them by the hand and led them over to the clearing,
away from the carriage and their mother, who had seen
nothing of what was going on, as she was tied to the
wheel on the opposite side of the carriage. On reaching
the clearing he lay down on the grass and the two girls
lay down beside him.
They spent a lot of time kissing and fondling each
other before he mounted one of the girls and made
passionate love to her, she was biting her lips as his
huge swollen penis entered her pussy, it was the
largest cock she had ever felt inside her hot body and
she rode it in a passionate frenzy until they both
reached orgasm, her body sucking in his seed deep into
her womb. The other sister had been kissing and
fondling both of them the whole time that they were
making love.
Jack continued to fondle and kiss both girls until his
libido had recovered enough for his penis again to
swell and grow hard, and then he mounted the other
sister and made love to her until they both again came
to orgasm together.
When they had finished, Jack led both girls silently
back over to the carriage, taking each of the girls
right hands, he brushed his lips across the backs of
their hands in a gentle kiss, then mounted his horse
and rode away.
As he rode, Jack contemplated on the robbery that had
gone wrong. Still he thought, as he rubbed the family
horseshoe birthmark at the top of his right thigh
through his trousers, at least I have got to meet a
couple of my daughters.
Epilogue:
Nine months later, both Mary and Anne DeBear gave birth
to two very beautiful blonde haired, twin girls with a
strange horseshoe shaped birthmark at the top of their
right inner thighs.
The End
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 30