The Twin Ordeals of Mistress Ruben
William was waiting. He was on the floor of the Main Dungeon, resting
on his elbows and knees, palms upturned, legs apart, head bowed and
completely naked. William was waiting for Mistress Ruben.
He heard the heels before he saw them. They click-clacked across the
floor and then came into his field of view, the first on the right side
of his torso and the second on the left. He felt the gentle caress of
Mistress Ruben's stockings as her legs rubbed against his body. This
pleasant sensation ended quickly. There was no welcome, no address,
only the sharp percussion of her cupped hand against his bottom. It
smacked left to right, then right to left, then found all the places
that hadn't been smacked and smacked them too. This was William's
introduction to a session with Mistress Ruben.
"Stand up, slave" she said abruptly. "Arms out, legs apart."
William complied and was rewarded with shackles around each wrist which
were clipped onto the ends of a bar that hung above him and a leg
spreader between his ankles. He looked straight ahead into the
full-length mirror mounted on the wall opposite and saw himself naked
and spread-eagled, ready for whatever Mistress Ruben had in mind. He
looked to the left and saw her reflection as she collected another
piece of equipment. He noticed her high-heeled shoes, her stockings
with suspenders peeking out from the tight, figure-hugging dress that
she wore. He was erect before she returned with the cock-tie.
"Standing to attention already, slave?" she asked rhetorically as she
wrapped the leather cord tight around his cock and balls, ensuring that
he would stay rock hard, "I might find a use for that later on."
She then fitted a slave collar around his neck and stood back to admire
"Today, slave" she announced, "You are going to endure two ordeals. The
first is the ordeal of pleasure."
She worked his standing cock rhythmically with the leather tip of her crop, leaning in close to him
until her lips almost brushed his ear and whispering "But you cannot
come until I command you" and added for good measure "In fact, I might
not let you come at all."
William's knees turned to jelly at the intensly pleasurable sensations
emanating from his groin.
"If you feel you are about to lose control" Mistress Ruben instructed,
"You must use the safeword to prevent it from happening."
"The second ordeal" she advised, "Is that of pain."
William had not seen the leather strap that she had been carrying in
her other hand but he certainly felt it as it made a loud "Crack!"
across his rump.
"I will be thrashing your arse until it is bright red and very, very
sore. Once again, if you cannot bear the pain, you can use the safeword
to bring it to an end. However, I have a reward for slaves who endure
my twin ordeals without using the safeword. Would you like a reward,
"Oh yes, Mistress" replied William.
"Very well then. Let's see how you perform."
In Mistress Ruben's left hand, the crop worked sensually on William's
cock. He moaned
with pleasure as he struggled to keep it under control. When her crop
wasn't working on his cock, her right hand and the strap that it
held worked relentlessly on his arse. He wriggled in a fruitless
attempt to avoid its sting and grunted, trying to avoid crying out in
case it jeopardised his reward. Sometimes, both worked
simultaneously and William was lost for an adequate response, being
caught between the horns of pain and pleasure.
"I'm always on the lookout for slaves with responsive cocks" chatted
Mistress Ruben amiably as she continued to thrash his backside,
"Particularly ones who can demonstrate good endurance. You see I have a
stable of slavegirls and they always need servicing. Do you think you
could service them for me, slave?"
"Oh yes, Mistress" gasped William as Mistress Ruben gave some extra
hard and fast strokes to his cock.
"Well we'll see if you're up to it, slave. Time for a position change,
William got a brief respite as Mistress Ruben unclipped his wrists and
led him over to the rack.
"Bend over that!" she ordered. William's wrists were clipped to the far
side of the rack while the ankle restraints were replaced with ropes
that stretched his legs wide apart. A third rope, looped tight around
his balls, was pulled under the rack and tied off. William was
completely immobile, his backside stretched tight and well presented
for further punishment. Mistress Ruben exchanged her strap for a
leather paddle and proceeded to increase both the pace and the weight
of the strokes applied to her slave's arse. William kept his mouth
closed to avoid crying out and instead focused on his promised reward.
"Just think of those slavegirls" she teased, "I'd have them all tied up
like this and you could go down the row, fucking each one of them in
turn! You like fucking, don't you slave?"
"Yes, Mistress" replied William from between gritted teeth.
After enduring a considerable amount of hard paddling
his arse and sensual teasing of his cock, he was once again
released. He relaxed and breathed deeeply, wondering whether his
ordeals were finally over.
"On the rack, face down!" ordered Mistress Ruben, indicating that they
were not over. With wrists and ankles clipped into the chains, the
rollers were wound tight stretching William along the full length of
"It's time for your backside to feel the flogger" she said. "Now I want
you to lift your arse up as high as you can to meet it."
William arched his body, lifting his bottom and stretching the skin
taut in anticipation. Mistress Ruben swung the flogger over her head
and brought it down smartly onto William's cheeks. The multitudinous
strands of leather cut cruelly into his rump.
"That was number one" she stated. "You will receive sixty."
Except for the sweet sound of leather against flesh, the flogging
proceeded in silence as both giver and receiver mentally counted the
strokes. After the sixtieth stroke, William managed a meek "Thank you,
"You're welcome, slave" responded Mistress Ruben, "However, I don't
think we've found your limit yet."
Returning the flogger to its hook on the wall, she picked up a large
wooden paddle, weighed it in her hand and nodded approvingly.
"I think a dozen strokes with this wooden paddle should nicely conclude
your ordeal. You'll find that this one stings quite viciously. Arse up!"
William lifted his backside again and as the crack of the first stroke
resounded around the dungeon, he knew that she was right. A sharp,
stinging pain accompanied each stroke, first on the right cheek then on
the left. He gritted his teeth but was unable to prevent grunts of pain
being squeezed out of him by the strokes of the paddle. After the
twelfth stroke had been delivered, he once again managed a "Thank you,
"Mmm, nice and hot" cooed Mistress Ruben, running the palm of her hand
over William's flaming red backside.
She released him from the rack and complimented him on his performance.
"It must be time for your reward" she added, "That fucking that we
talked about earlier."
"Oh yes please, Mistress" pleaded William, still horny despite, or
perhaps because of, the fire burning in his backside.
He was placed on his knees, hands behind his back with instructions to
keep his eyes tight closed whilst preparations were made. He could hear
the door opening and closing and lots of moving about. In his mind's
eye, he imagined the slavegirls being brought in and tied across the
rack. His cock was bursting with excitement as he imagined himself
penetrating each one in turn and giving her a good hard fucking before
moving onto the next. Then he heard Mistress Ruben's voice.
"I always think that foreplay is very important, don't you slave?
Perhaps some oral sex to get the participants warmed up?"
William's vision changed. What did she mean? Were the slavegirls going
to suck him off before he fucked them? Was he going to perform
cunnilingus on them, licking each one to orgasm? Perhaps both? Any of
these things was fine by him.
"Oh definitely, Mistress."
"Well that's good, slave, because we're almost ready. I think you can
open your eyes now."
William opened his eyes to see Mistress Ruben's groin inches from his
face. She was wearing a strap-on harness from which protruded a large,
red dildo. The tip of the dildo was directly in front of William's
mouth. As he opened his mouth to cry "No!", Mistress Ruben thrust it
forward, cutting him off as his mouth was filled with the surrogate
"Suck it slave" she ordered, "Show me how you worship your Mistress's
William struggled to take the dildo into his mouth. He managed at first
but as Mistress Ruben thrust it deeper and deeper, urging him to take
it all, he began to gag. A look of mock disappointment crossed her face.
"Well if you can't fit it down your throat, we're just going to have
find somewhere else to bury it, aren't we?"
William was quickly placed on the sling and his legs spread apart,
clipped into the chains that suspended the sling from the ceiling.
Standing between his legs, Mistress Ruben opened him up, then
penetrated him with the dildo. Swinging her hips back and forth, she
began to fuck him. With each forward motion, he felt the dildo go
deeper inside him, deeper and deeper until he felt Mistress Ruben's
hips bang up against the sore cheeks of his bottom.
"I'm balls deep in you, slave" she announced. "Now when you fuck my
slavegirls, this is how I want you to do it."
He felt the dildo being pulled all the way out and then pushed all the
"And when I tell you to fuck them hard and fast, this is what I want
you to do."
She wrapped her arms around his thighs and used them to hold him steady
as her powerful hips slammed the dildo hard into him, over and over and
William could not believe that he had submitted to this. His arse
cheeks were on fire, and his hole was being energetically violated. And
he was loving it! His cock was rock hard, bursting for release.
"I expect you'd like to come now slave, wouldn't you?" Mistress Ruben
asked, somewhat redundantly. One of William's wrists was released and
he was ordered to bring himself to the point of orgasm. "Don't forget
to ask before you come, though" she reminded him.
As Mistress Ruben continued to fuck his arse, William quickly brought
himself to the edge of orgasm.
"Please Mistress" he begged, "May I come now?"
"No!" she replied, with a little laugh.
William hesitated, confused about what he should do.
"Bring yourself to the edge again" she ordered.
It didn't take long and once more William asked and once more he was
On his third attempt, there was genuine pleading in his voice as he
begged for release.
"Hold it there, slave, hold it" instructed Mistress Ruben as she gave
his arse a little extra hard fucking.
"Now come for me, slave, come for your Mistress!" she shouted. William
exploded, the hot fluid shooting onto his stomach and splashing onto
his chest. He continued masturbating until he felt that there was no
more to come.
But Mistress Ruben had other ideas.Pulling out the dildo, she thrust
her hand inside him. As she firmly massaged his prostate, William was
amazed to see yet more white fluid come dribbling out of his cock.
Eventually even this flow dried up and they both had to admit that he
had no more to give.
Later, as William left the premises, he left with a very sore arse, a
pair of fully drained balls and a very large smile on his face.