This is a very extreme fantasy – anal pear

At my order, big Kargoth lowered the singletail and stepped
back. Kerry Black leaned — no, better, sagged — against the
leather-padded whipping post, breathing heavily, loudly.

His arms were stretched over his head, the leather wrist cuffs
chained to the metal ring at the top. His whipstreaked back
glistened with sweat wherever his long, curly brown hair didn’t
cover it. Candlelight flickered off the little gold reversed
crucifix dangling at his throat.

The air of the “dungeon” room reeked with smells that told a
story: the tangy-sour scent of fear, the sharp musk of the anger
that was so much a part of his psyche, the more subtle musk of
masculine arousal with its hints of semen. And, of course, the
smells of leather and sweat, and the faint burning-paraffin
scent of more than a dozen candles set in iron sconces around
the room, casting their golden light on his compact, muscular
body.

I savored those smells, savored the sight of his body in the
flickering light. Kerry’s head was half-hidden by his long hair
at the moment, but then he lifted it slightly, turning to me to
glare once again. He didn’t bother to glance down at my breasts.

*You can’t break me*, the look in those dark, angry eyes said.
*You haven’t even *hurt* me yet.*

He’d just taken a hundred lashes, half of them with the
singletail. It would have been an extremely severe whipping for
anyone else. For Kerry, it was barely out of the parking lot.

I looked back at that blunt, brutal face with its heavy brows
and deep, dark eyes, at Kerry’s anger no longer sullen but fully
aroused and flaring — like his penis, rock-hard in spite of the
pain he’d just endured.

If I didn’t break him, or at least impress him, I’d lose his
respect.

I wasn’t worried.

“Like that?” I said, smiling blatantly into his face. “Well, it
gets better. I’ve got a little surprise for you.”

I went back to the dresser in the corner of the room, opened the
top drawer, and pulled out the little wood-and-metal object.
When I returned to his side, I held it up to his face as he
leaned against the whipping post.

Kerry shook the hair out of his sweaty face to get a better look
(and more candlelight flickered off that reversed crucifix), and
then his jaw went slack, eyes widening. He recognized it, all
right.

“No way!” he said, his rough voice hardly more than a husky
whisper. “No –” And then he turned his face away.

I grinned. This time I’d really rocked him.

“Come on,” I challenged. “Take a look. I went to a lot of
trouble to have this made, just for you, because I don’t know
any other sub who could take it.”

Kerry can’t resist a challenge to his pride. Reluctantly, he
turned his head again to get a closer look.

The pear was one of the most vicious devices in the arsenal of
medieval and Renaissance torturers, which was why he recognized
it. Perhaps even had an encounter with it in some forgotten or
not-so-forgotten past life. This one wasn’t that old; I’d had it
custom-made, out of polished wood instead of metal.

It looked like an elongated wooden pear or a fig, only three
inches wide at the widest part, with a little metal crank where
the stem would be on a real pear.

I demonstrated its workings, turning the little crank to open it
up. The four beautifully dovetailed ‘quarters’ of the pear
opened up, widening like vise jaws in reverse, to their maximum
width as I kept cranking – about five inches, as big as a large
fist.

The original versions would have been bigger – big enough that,
when used, they usually killed the victim.

Kerry clamped his jaw again, his face turning a shade paler.
Kargoth laughed – mockingly, cruelly, white teeth gleaming in
his dark face.

I waited tensely for a safeword. None came. Instead, he lowered
his head again, giving me an ever-so-little headshake, and I
heard a muttered “Fuck.”

“Let’s get him over the padded bench again,” I said to Kargoth,
who grinned and stepped forward.

Later: bent over the bench, he was an even better target, his
muscular ass offered up invitingly. Kargoth used him a second
time, fucking him slow but hard, making it hurt as much as
possible. Kerry clenched at the stout bench legs, at the chains
holding his wrists to them. His head was up, his face almost
beautiful, transfigured by mingled pain and passion, now
gritting his teeth, now open-mouthed and moaning — not with
pleading but with pleasure.

Toward the end he was actually thrusting back, making the bench
squeak, grinding his ass into Kargoth’s pelvis. I squatted down
to see his penis, now harder than ever as Kargoth fucked him. He
couldn’t quite rub it against the padding, but it looked like it
was dripping precum.

Kargoth came inside him, throwing his head back and grimacing
with ecstasy. He stood there a few moments relaxing, while Kerry
slumped with mingled relief and disappointment over the bench,
before he stepped back to leave him once again.

I went over, squatted down again and examined Kerry’s puckered
little anus. After two fuckings already, not to mention a
session with my largest strap-on, it was swollen, still slightly
open and leaking Kargoth’s cum in a sticky stream down the
cleft.

He was ready for a bigger caliber.

I rose and got the pear again. As I approached, I was rewarded
with the sight of his hard muscles tensing up. I held the toy up
before his eyes once more; he stared bravely at it, but I could
smell his fear.

The tension between us was electric; he was aroused, terrified –
– and very genuinely angry, as he so often is during our
sessions. I gave him my best predatory mocking smile, looking
into his eyes.

“You — fucking — bitch,” he gritted.

I let my smirk get broader, and then I walked around the bench
to his other end.

I’d greased the pear, of course. Kargoth held his buttocks open
as I pressed the bulb against that hard-used, quivering anus and
slowly pushed.

Kerry’s body shuddered all over. Having to take that terrible
thing into his anus was probably the hardest thing he’d ever had
to do under my command, but he’d be damned if he’d safeword.

Slowly, slowly, the ring of the anus stretched around the pear,
helplessly accepting it.

I don’t know how long it took for me to get it all inside him.
Maybe five minutes, maybe ten, as I pushed it little by little,
never letting up the pressure except when I paused to let his
rectum adjust. He writhed slowly on the bench as Kargoth held
his ass wide open, muscles standing out in relief, shaking his
head, his entire body rigid.

As the widest part of the bulb entered his tortured asshole, he
actually groaned despite himself, “No . . . no . . .”

“I do not hear a safeword,” I told him. “Do I hear a safeword?”

“Nope, no safeword,” said Kargoth, grinning from ear to ear.

“Shit . . . *Damn* you, bitch!”

Once the bulb was in, the rest followed easily. At last the
whole torture device was buried in him, up to the little ‘stem’
end with its crank.

His life was in my hands. It would be so easy to go too far . .
. . And his agony, too, was in my hands. That’s what really got
me going! I could inflict as much as I wanted, as long as I
wanted.

I eyed his taut, sweating body. I couldn’t see his face, only
his shaggy dark hair, but I knew already he was in Purgatory. I
considered my choices: take him to Hell right now, or taunt and
tease him with the agonizing anticipation?

I opted for a few moments of teasing, nudging the pear, playing
with it as it protruded from his asshole. His entire body
writhed slowly, unable to remain still, but he didn’t make a
sound, except for the hiss of his explosively released breath.
He wouldn’t give me his cries yet.

Kargoth squatted on his haunches in front of Kerry. His black
face was split in a wide, white, cruel grin as he watched
Kerry’s face. But I knew pretty much what he was seeing: Kerry’s
teeth gritted, jaw muscles trembling with the strain, his face
twisted in utter agony.

And then I began cranking the pear open, as slowly as possible.
I braced the protruding end with the fingers of my left hand and
gave the crank a slow turn with my right — it expanded maybe an
eighth of an inch with each full crank. One full turn . . .
another . . . Even before I finished the third turn, Kerry was
shaking uncontrollably, and once again his exhalation was a
hissing whimper.

I paused, my hands poised on the pear. “Want to safeword?”

He shook his head angrily, sending sweat flying from his
drenched hair. More sweat was literally running in rivulets onto
the leather of the bench, every muscle was quivering, the agony
had to be excruciating — and he would *not* safeword. I gave
the crank another turn and stepped back to watch again.

We watched for fully a minute as he writhed on the bench, body
jerking, fists clenching. His erection was down to half-mast.
Not even Kerry can eroticize that much agony, even though he
needs desperately to feel it.

Then I stepped forward again. This time I tried just a half
turn.

I couldn’t have gotten a more powerful reaction if I’d run a
jolt of electricity through him. His scream of pain punished my
ears as he lost control, and his entire body spasmed and arched
on the bench, one big hard tight muscle. The crank was torn from
my grasp and I pulled back my hands as his hips wrenched away
from me, his body trying wildly to escape my torture even as his
mind refused to safeword.

Kargoth’s eyes glittered with delight as he watched, and I
wondered if mine did, too. His erection was at full mast,
practically slapping against his belly as Kerry writhed on the
bench, his scream dropping to a strained, involuntary whimper.
Finally Kerry took a hissing intake of breath, teeth bared, his
whole body shaking as he regained control.

I watched in awe. I honestly hadn’t thought he’d be able to stop
screaming. But then I crouched down again to continue.

Kargoth stepped around to seize his hips as my hands once again
went to his ass — and the gracelessly protruding crank.

Another turn — same thing. Once again I got only one scream,
and no safeword. Sweat dripped off the bench onto the concrete
floor.

Another turn. Another . . . more . . .

And finally, with the pear opened to more than four inches wide
inside his rectum, Kerry arched and threw back his head again,
screamed more loudly than ever — and then slumped in total
collapse.

I let go of the crank, straightened up and went over to his
head, brushing his hair back to get a look at his face. He was
out cold, in a dead faint, eyes closed, face slack.

I glanced over to Kargoth, who shrugged and looked disappointed.
As for me, I was almost relieved. Almost.

I padded back to Kerry’s hindquarters. On a sudden thought, I
pushed a hand in between his groin and the padding — he was
lying belly-flat to the bench now. It came away drenched, but I
wasn’t sure whether it was semen or just sweat. He’d really
soaked the bench during his agonies.

I cranked the pear back closed again and gently withdrew it from
his tortured anus. There was no bleeding, but it remained half-
open in a gentle pout, swollen and a bit reddened.

Only as Kargoth and I unchained him, half-dragging his
unconscious form off the bench, did I finally see that there was
indeed a big splotch of thick, translucent semen on the wetly
shining cover, dripping down to the floor. Somehow, he’d managed
to come while half-hard.

Kerry came around with his usual speed a few minutes later on
the nearby sofa. He shook his head, blinking his eyes as we
watched. Then his hand went down to his crotch, feeling his now-
limp penis — and he cursed savagely and glowered up at me,
taking his gleaming-wet hand away again.

“You cunt! You fucked up! I should have been awake to enjoy
that!”

I smiled a snake’s smile right back at him. “Is it my fault you
couldn’t take it? You’re the one who passed out cold.”

Kargoth laughed.

Kerry glared at each of us in turn, then finally sighed and gave
up.

“All right,” he growled. “But I want another chance to come
later.”

I wordlessly padded over to the small fridge, brought out a
bottle of beer and opened it. I smiled as I walked over to his
side, squatted down and offered the bottle to him.

“You got it.”