sissy baby Jenny is a cuckold
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Sold Sissy Cuckold
By Debra Darling
"Damn, I hate wearing these things!" she exclaimed as she kicked off her
red high heel pumps. "I don't think it's fair that I have to stand
around all night in these things just to make you look better to your
clients."
"You know how important it is to my business," he replied. "How you
look affects how successful they think I am. Besides, it's no big deal
wearing them. It's not as if other women don't do it all the time!"
"Maybe so," she said, "but I think it's about time we leveled the
playing field a bit. It's my turn to be the top this weekend and I
think we'll just go with something I have been toying with for a long
time."
They said nothing more about the subject but on Saturday morning she had
a bunch of bags and boxes set out on the bed. They usually spent the
weekend playing bondage games. They were in the habit of taking turns
as to who was in charge. On special evenings, they even invited the
neighbors, Bob and Sandy, over for some spouse swapping as well.
"Get naked!" she commanded him.
He stripped off his bathrobe and shorts and stood before her in nothing
but his birthday suit. He expected her to produce arm and leg cuffs
before she led him down to their basement dungeon but this time she had
other things in mind.
"You always want me to wear sexy, fetish outfits," she said. "I have
decided it's time for you to see what it feels like to be on display as
a sex object."
She handed him a black Merry Widow like the one he often had her wear.
It zipped up the front and tended to cinch her waist in. Garters hung
down from the bottom and the cups were padded to lift her breasts up and
together
It was clearly a bit too small for him but with a struggle he did
finally manage to get the zipper closed. He felt like his waist was
being crushed but it was not so bad he could not manage it, at least for
a little while. He took the silicone breast pads she handed him and
placed them in the bra cups which pulled them tightly back to his chest.
They felt sticky where they touched his skin and he soon realized they
were coated with surgical glue. Quickly they were firmly attached to
him. With the bra padding he now had not only boobs but a substantial
cleavage as well.
She handed him a package of Hanes stockings, black with a sandal toe, a
Cuban heel and seams to go up the back of his legs. They had a lace top
where the garters would attach to hold them up. She showed him how to
roll them and ordered him to put them on.
"If you run them," she threatened, "you will pay dearly with the cane
when we go downstairs. Also, the seams had better be perfectly straight
when you are finished."
He was oh so careful to follow her instructions and it took him several
minutes to get the stockings on, pulled up tight and fastened in place
with the seams straight. She seemed almost disappointed that he got it
right.
At this point he felt very foolish but also somewhat submissive. He
also had a massive erection which she stroked a couple of times,
suggesting what was to happen.
From a box on the bed came a pair of shoes. They were black patent with
a rounded toe and an ankle strap.
"These are called Mary Janes," she explained. They are not as extreme
as shoes with pointed toes but I'm sure you will soon get the message
about how I feel when I have to wear them. I did get ones from the
fetish store because they had them with much higher heels than most.
These are five and one half inches high, about as high as they can be
without a platform."
She helped him put them on and then fastened each ankle strap as tight
as she could. Even so, he figured he could, with a little work, manage
to kick them off if this got too painful.
He stood patiently in place while she put the inevitable ankle cuffs on
him. He helpfully put his arms behind him to make it easy to put on the
wrist cuffs. What he did not expect were the elbow cuffs she fastened
on each arm and then cinched together until his elbows nearly touched.
With his arms held this way he realized he was really totally helpless.
"Now for really interesting fun," she smiled. "Let's see if you can
keep it up in all your finery."
She took his penis in her hand and began to rub it up and down. It did
not take long for him to respond and he was soon harder than ever. He
watched with some trepidation as she then did something new. She pulled
his cock out as far as she could and slid a lubricated latex tube over
it. Once it slid past the head, it compressed the shaft of his cock and
kept it extended. Over this tube he then noticed a second covering of
leather which had laces like a corset. She quickly laced the device
closed and his cock felt like it was being held in a vice. Two straps
went down and around his balls, separating them and holding them apart
like two solid balls.
She flicked each ball and then the cock head and he winced with pain.
"I think playing with this is going to be such fun," she said. "At
least it will be fun for me."
"Now for the ultimate controller," she said. "A lesbian domme with a
truly intense hatred of men showed me this little device. She said no
man could withstand it and would do anything he was ordered once it was
installed."
She held up a strange metal tube, very small in diameter that ended in a
ring. The tube was hollow and where it met the ring there was small
hole. He began to understand its purpose when she told him that once
installed he would work very hard to maintain his erection but he would
still be able to empty his bladder if necessary. Almost as an
afterthought, as she lubed the tube up, she let him see up close the
tiny barbs that lined the thing. They would slide in easily but any
attempt to remove the device would be very painful and the barbs were
lined up to dig in when it was extracted. A special tool could be used
to activate a device in the ring and retract the barbs. Otherwise any
pull on the ring would be very painful indeed.
He could not believe what she was doing as she inserted the tube into
his cock and pushed it home. Once in place she fastened a leash to the
ring and began to pull. He quickly learned it was too painful not to
obey and he followed her around as she led him through the house and
then down to the basement.
He still figured that as soon as he was alone he could force off the
shoes and manage to get out of the house. It would be embarrassing to
run next door but once there his friend Bob would surely help him get
out of this predicament.
Then he arrived at the rec room. In the middle stood the stocks but his
wife had replaced the center boards with two new ones that had only one
small hole. A not so gentle tug on his leash and he stepped forward and
soon found his cock resting in the half circle in the top of the bottom
board. When the top board was slid into place and the locks snapped
shut he was helpless, standing on one side of the stocks with his cock
and balls on the other side.
He was trapped and as he stood there he began to realize that those
shoes were really causing his feet to ache and the muscles in his legs
to tense up and even cramp. Then things got worse.
His wife went behind him and he felt a blow behind his right knee.
This, combined with a tug on his ankle cuff quickly caused his leg to
bend and his foot to come up high behind him. A short chain with hooks
at each end fastened his ankle to his wrists.
Now his weight was all on one foot and he could not lift it up without
hanging from his cock and balls. He could not shift his weight enough
to get out of the shoe and his leg was already cramping from the stress.
"Stand there," she announced. "Stand there until you are ready to beg
me to release you. See if you can think up something fitting for me to
do to you as a reward for letting you go."
When his wife returned his leg was on fire. He knew he would do almost
anything if she would free him. Then he saw what she was wheeling in.
"Oh no!" he thought. Surely she was not going to use that on him. He
could not bear the thought but he knew as the pain in his leg grew worse
he would, in deed, beg her to violate him with the device.
"Remember this?" she asked. "Remember how you used it on me until I was
screaming in desire and pleasure? Remember how you thought it was so
funny to then let it slide up into my ass? Well let's just see if you
still think it's so funny."
The device was the fucking machine they had built based on one they seen
on Gord's web site. It sat on a sturdy base and consisted of a pole
with a dildo machine on the top. The machine worked like a piston,
sliding up and down at whatever speed was desired. The dildo was meant
to ravage a vagina and drive a woman to orgasm, over and over until she
was satiated.
She had loved it when he had slid it up inside of her pussy and turned
it on. He had watched her as she alternately begged and pleaded and
then screamed her pleasure as she was driven to orgasm after orgasm.
When she was at last exhausted he had suggested another use which she
did not appreciate. He had only let it slide up into her helpless ass a
couple of times before her threats convinced him that this was not a
good idea. Obviously, she was even less happy about the experience that
he had realized.
"Beg for it," she commanded. "Beg for it or stand there for another
hour while I get the place ready for tonight's party"
He had forgotten about the party. Now in addition to the agony of
standing on one leg for so long, he also faced the humiliation of having
his friends and neighbors seeing him attired like a silly sissy.
He figured if he gave in he could bring all of this to an end.
"OK!" he said at last. "Go ahead and use that thing on me like I did to
you."
"Say pretty please," she said.
"Pretty please," he managed to say through clenched teeth.
"Not good enough!" she exclaimed. "Tell me how much you want me to use
this on you. Tell me you want to experience it for as long as I was
forced to endure it. Go ahead. I want to hear real sincerity in your
pleading."
In the end he did everything she asked. He begged and pleaded and
described how much he wanted to ride the machine until she finally
decided he was truly ready.
He had to watch as she prepared the device for him. The dildo she
mounted on the shaft of the machine was the same on he had used on her.
She made sure he realized that. But she then added something horrible
to it. Once it was fully lubed up, she had slid what she called the
five gates of hell onto the dildo. This consisted of a series of rings
that ran the length of the plug and gripped it tightly. They would not
move but he would feel each and every one of them as the thing slid into
and out of him.
She went around behind him and he felt her position the machine until
the tip just touched his anus. She released his leg from his wrists and
it fell quickly to the ground. As he shifted his weight at last, she
pulled up the other leg and fastened it to his wrists.
"Not fair!" he yelled. She only smiled and said nothing.
Then she turned the machine on and he felt the dildo drive its way up
into his rectum. One by one the rings slid past his anal opening. Inch
by inch the thing slowly made its way deeper and deeper. When it
reached the maximum depth it paused for a moment and then it quickly
withdrew until all but the head came out. Fastened as he was there was
no way he could lift himself off the device.
He could only stand in place in that horrible high heel as the device
slowly clicked its way back up again. He could not help himself from
counting the rings until the fifth and last one passed inside. Then the
pause followed by the quick withdrawal.
"Fun, isn't it?" she gloated. "Count the strokes," she commanded.
"I'll be back soon and you had better have the count correct. If not,
we'll just start over."
"Oh God!" he thought as he neared the one hundredth stroke. She
returned and stopped the device.
"How many?" she asked.
"One hundred," he replied.
"Close," she replied. "But you forgot the first one. It was actually
one hundred and one."
He groaned in despair until she said she would let him off anyway. Sort
of, anyway.
He felt her adjust the dildo upwards until it was buried inside of him.
Then she came around and began to play with the head of his dick. It
was so sensitive that he moaned in pleasure. When she knelt down in
front of him and took him in her mouth he knew he had never felt
anything like that before.
"I'll give you five minutes," she said. "If you can hold out that long,
I'll release you. If you come I'll force you to suck it out of my mouth
and swallow all if it," she told him. "Then we will start all over."
She went to work. Between the pressure of the dildo on his prostate,
all of action all day long and her expert work on his cock head he
barely made it at all. Five minutes was hopeless. He came almost
immediately.
She was good to her word and he was forced to accept her mouthful of his
cum and to swallow it down. She then seemed to relent and she released
his leg. But not for long. Before he realized it she had pulled his
legs apart and fastened them to the base of the stock uprights. He was
still trapped but at least both feet were on the ground.
That was where he was when the neighbors arrived. Bob had his wife
Sandy in simple bondage. He seemed to know what was going on as he
quickly shed his clothes. Then with Sandy standing by, Bob and his wife
began to fuck each other on the bed in front of him. He heard a click
and felt the dildo machine come back to life. It was much worse now
that his initial sexual excitement had been satisfied. It went on and
on until his wife had her third orgasm.
At that point, the phone rang and he heard his wife answer. He could
only hear her side of the conversation.
"Yes. He is ready," she said. "Send the collection crew over anytime.
No, he needs to be trained. He has experienced slavery, he knows he is
a cuckold, he is outfitted like a proper sissy. We agreed on the price
with the understanding that you would handle his training and that I
would receive videos as he moves deeper and deeper into sissy slavery
and finally accepts his role and is sold to his new master. Whatever
you make over what you pay me is yours to keep."
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