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July 16, 2007

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The worst was that Jill knew she was pretty and took advantage of that

fact to torment me further. She would unexpectedly brush against me, or

casually sit with her legs wide apart so I couldn’t help but see her

naked sex, so close but so forbidden.

At one point she so distracted me that I dropped a dish and one of the

cooks angrily beat me with a wooden paddle, urging me to be more

careful. Jill stood nearby and looked innocent, winking at me with her

wide eyes and casually kneeling and caressing my cock as she told the

cook to punish me harder. I was weeping helplessly when it was over. But

then the cook took a large carrot with a leafy stalk and thrust it deep

into my buttocks.

“Keep that in place,” he ordered, “or you’ll really be asking for

punishment.” So in misery I crept back to my duties and tried to ignore

Jill’s smart comments about how pretty I looked with a green stalk

sticking out between my legs.

“It’s almost as though you have two cocks,” she said with a giggle.

“One green and large behind and one tiny and red in front!”

Because of the feast that evening there was no lunch so there was no

respite to my misery. As the day wore on Jill seemed to become more and

more bored with her duties, pushing more of it upon me. I hoped the

cooks would notice it and report it to the mistress but they were too

busy. Jill seemed determined to take out her frustrations upon me, and

several times she warned that I was in for dire punishments as soon as

we were finished with our duties. This terrified me. So though I was

tired I didn’t want our work to end. What terrible cruelties did Jill

have in mind for me?

Our duties were finally over early in the evening, and I had the

unwelcome opportunity to find out. We weren’t permitted to go to the

banquet, of course, so our time was our own until the master or mistress

called for us at bedtime.

First Jill and I took another bath. The cool water felt delicious

against my punished skin, and again I was aroused as I washed Jill’s

body. I was finally permitted to remove the carrot from my anus, but she

made me eat it, which was a miserable task, but I was hungry and I

didn’t want it put back.

After the bath she took my cock in her left hand and proceeded to whip

my thighs until I could barely stand still. This gave her an idea, it

seemed, so she had me run in place as she whipped me, enjoying the sight

of my body as I jogged. When this was finished she put her face close to

mine and ordered me to crawl on my hands and knees to her room, where

she could “really” punish me.

In misery I crawled before her, the stone floor of the courtyard hard

on my knees, her belt never idle. “Keep your head lower,” she shouted.

“Arch your back, let me see those buttocks in the air!” I couldn’t move

fast enough for her, and she whipped me constantly.

By the time we were in her room I was completely exhausted. I felt I

couldn’t endure any more. “Flat on your back,” she ordered, and I

obeyed, though the stone floor was like ice against my burning bottom.

“Lift up your legs and grab them with your hands and pull them to your

chest,” she commanded, and I obeyed the best I could. She made me spread

my legs wider, which meant I could pull them closer to my chest and also

that my cock and scrotum were more visible. My buttocks felt split and I

knew my anus was painfully vulnerable. I felt horribly exposed and

humiliated. My face was flushed and I knew that there was nothing I

wouldn’t do for this pretty little dark-hair beauty that knew how to

torment me so well.

As I lay in this undignified position she knelt beside me and licked my

face. “Do you like this?” she asked. “Isn’t this the proper position for

a naughty slave like yourself?”

I moaned in misery but she just giggled and leaned so close I felt her

nipple touch my shoulder. “Look at your cock,” she whispered. “It knows

what you like. Look at it grow.” I watched in astonishment as my cock

grew larger even as she spoke. I had never seen it so enlarged. It

swelled to such proportions it was almost frightening, but I was past

caring. All I could do was whimper and wiggle it in the air and hope

that she would have mercy upon me.

But this was Jill, not an angel, and she didn’t know the meaning of the

word mercy. Her hand reached out and touched my cock and I saw a tiny

droplet of moisture ooze out the tip. “Naughty, naughty,” she hissed at

me, her eyes bright with excitement. My heart beat wildly as I watched

her pick up her leather belt. She smacked the back of my legs again and

again. The blows were hard and fast and stung without remorse. I wanted

to scream.

“There now,” she said when she had finished, “we must keep your passion

in check, boy!” As she said this she caressed my cock lightly, teasing

me, daring me to defy her again. I desperately tried to think unsexy

thoughts, to think of the punishment I would surely receive if I

disobeyed her. Somehow my cock obeyed.

Almost disappointed, she resorted to other tricks. I saw her game now.

She meant to make me come and then punish me severely for it. This

frightened me greatly, because I could think of nothing I wanted more

than to come, right there.

Her first trick was to stand before me and show me her body. This was

tempting, to be sure. She stood and caressed her breasts, squeezing them

in her palms and showing me the stiff nipples. Next she ran her hands

over her body, along her waist and hips and down to her sex. There she

spread her legs and I could see the moisture that extruded there she was

so aroused. “Don’t you want to lick me?” she whispered.

She turned slowly away from me then, her hands going back and resting

on her buttocks. She patted her bottom and rubbed the cheeks against her

palms. Standing stiff she bent way over taking care not to bend her

knees. She grinned at me from between her legs and slowly began to

spread her legs wide. Soon I could see her sex between her legs and I

felt my cock ache.

When her legs were wide enough apart she began to wiggle towards me,

taking tiny baby steps backward, so that soon she stood over me, my body

between her spread legs. Staring straight up into her sex, its narrow

mouth open and craving my cock. I began to cry. This was too much. It

was irresistable.

She began to lower herself, now, the mouth coming closer and closer to

my face. I desperately gripped my legs closer to my chest and thrust my

buttocks even higher into the air. My body was shuddering with

anticipation. Suddenly I felt a drop of moisture splatter on my face and

I saw with astonishment that she was dripping on me!

She paused just inches from my face, her body in a painful squat, and

then she began to wiggle her bottom. Her body arched with tiny pelvic

thrusts that drove me into a frenzy. It was all I could do to not let go

of my legs and wrap myself around her and take her. But the punishment

for a slave’s satisfaction is unendurable. At least I had heard that it

was. At the moment it seemed a minor consideration.

Suddenly Jill stood and turned and knelt beside me. She leaned over my

head so that her outstretched tongue was licking towards my cock. It

bobbed wildly in anticipation but she kept teasing it, never making

contact. Her breasts dangled in my face and I managed to lick her

nipple, which caused her reach around me and pinch my buttocks cruelly.

How long these tortures lasted I do not know. It seemed like an

eternity, and at some point my mind lost track of the order of things. I

remember her body toying with me, brushing against me, against my cock,

her tongue licking at my balls. But nothing was ever quite enough to

give me satisfaction. Each time I was aroused to the point of explosion

she would spank me, a long hard spanking that had me weeping and begging

for mercy when she finished.

She had a thin wooden paddle in her room, and a couple of times she

made me lay across her lap while she paddled me, making sure my cock

couldn’t brush against her legs. The relief from having to maintain my

sprawled and exposed position was wonderful, but the paddling was quite

harsh. As soon as she had finished I promptly had to return to my

doubled position on my back, my buttocks and sex exposed.

Once I remember her squatting below me and placing her cool buttocks

against mine. The sensation was thrilling. She moved up slightly until

she was almost sitting upon my thighs, my balls against her bottom. This

made me weep.

Another time she decided to play with my anus, and she amused herself

by placing various objects into me with scarely a glance at my tormented

face. She started small, with twigs or metal spoons, but soon she was

inserting broomsticks and even the wide handle of her wooden paddle.

In this way the evening passed. Occasionally in moments of quiet I

could hear the distant sounds of the banquet we weren’t permitted to

attend, but we were not interrupted.

At one point it seemed very late and I wondered how much time had

passed. But Jill was in the process of paddling me across her lap for

yet a third time and I soon forgot all about the time and concentrated

on moaning and showing the proper abasement of a punished slave.

After the paddling Jill seemed especially passionate and I remember

wondering if perhaps at last she’d allow me to satisfy the both of us. I

was in my miserable doubled position again when she sat on my thighs,

this time facing me. My cock was inches from her sex and I could feel

her wetness against my balls. I moaned and wiggled desperately.

Then she did it. She leaned forward and took me insider her. The

position was awkward but I didn’t care. With rapid movements she began

to ride me. Almost immediately I felt myself swelling with imminent

orgasm, but suddenly I froze.

Standing in the doorway was the Master, and next to him the Mistress.

With a frantic moan I tried to warn Jill but she had her back to the

door and plunged away. My cock burst as the Master pulled a shocked Jill

away from me and I sprayed my come everywhere. The relief was immense

but the dread in my heart was unbearable. What would the Master do?

A large man, he pushed Jill against the wall and slapped her face

several times. As soon as the shock wore off she bowed her head and

wept. But the Master was too angry to let this pacify him.

“Horrible, disobedient slave!” he hissed. “How could you do such a

thing? You know that slaves may only be given pleasure by their Masters

and Mistresses! How dare you!”

Jill wept and knelt to kiss his feet but he kicked her away. He turned

and looked at me and I saw his eyes go wide as he studied the welts on

my buttocks and thighs. “So you’ve been having a little fun at Will’s

expense?” he said to Jill. “We shall see how you like your own

medicine!”

He snapped his fingers as Jill crawled to obey. “Assume the same

position,” he ordered, nodding toward me. I watched with delight as Jill

laid down on her back and awkwardly pulled her legs to her chest. The

Master knelt and spread her legs wider, so wide she was gasping. “Hold

that position.”

He took her leather strap, the heavy one I’d learned so much from that

day, and proceeded to whip her bottom and thighs soundly. It was an

excellent whipping. Though most of my whippings came from Mistress

Samantha, I’d received enough from the Master and I knew he did not

believe in mercy.

The belt smacked her rump countless times and then proceeded to whip

her thighs for a while, then her buttocks again, then her calves, and

back to her bottom. Jill was groaning and whimpering, wiggling her body

the best she could to ease the blows, but there was no escape. She could

only weep and hope the Master would cool down.

But he was furious. With a sudden movement he lifted her and flung her

across his lap and proceeded to spank her bottom with his hand,

tremendous swats that must have hurt as much as a paddle. Soon he grew

tired of this and picked up the wooden paddle and gave her the hardest

paddling I have ever seen anyone receive. Jill was sobbing outloud-she

couldn’t help it–and I watched as her shapely bottom danced under the

blows. Her round buttocks and creamy flesh that had so tormented me

moments before was now swollen and fiercely red.

Still the Master was not satisfied. He lifted her and placing her on

his knee he began to spank her naked breasts. Jill’s head was thrown

back and she moaned as he slapped her breasts, the nipples huge and

erect. Jill’s legs were spread wide and I could see her naked sex

dripping as she bounced on the Master’s knee, her raw buttocks pressed

against his leg.

Suddenly I felt a hand touch my cheek and I looked up to see the face

of the Mistress kneeling beside me. She was smiling and her hands were

caressing my body. Her hand went down to my cock and I thought I would

die, but she only wiped a droplet of come off by thigh with her finger

and brought it to my lips and forced me to swallow it. Her expression

did not change the whole time.

I wept as I sucked on her finger, the sounds of Jill’s punishment

echoing frighteningly around the small room. To my immense relief the

Mistress released me from my doubled position and had me stand. I saw

that Jill was spread facedown on the floor with her buttocks high in the

air. The Master was naked and I saw him plunge his huge cock into her

buttocks without any foreplay and I knew that it must have hurt her

tremendously.

But then the Mistress made me turn to her and kiss her breasts.

Mistress Samantha was wearing only a thin nightgown and I realized that

the banquet must have ended hours ago and they were preparing to retire

when they noticed our absence. She slipped off the nightgown now and I

kissed her naked breasts. Kneeling, I licked at her sex. Behind me I

could hear Jill grunting with pain as she was raped. Somehow this

excited me and I licked Mistress Samantha frantically.

Moaning, the Mistress pushed me away and turned her back to me and I

began to lick and kiss her buttocks. She had wonderful buttocks,

Mistress Samantha, large and round and supple, and I often wondered if

the Master didn’t ocasionally enjoy giving her a good spanking. Just the

thought of having her round bottom under my hand aroused me fiercely,

and I redoubled my efforts at licking her buttocks. I licked into the

crack of her ass, my tongue tickling the tiny hole of her anus. The

Mistress moaned and leaned against the wall, bending over slightly to

make my task easier. I began to lick at her sex from behind, licking the

juices that trickled down her thighs.

Behind me I heard the paddle going again and I couldn’t resist a

glance. Jill was on her back and doubled again, but this time the Master

was holding her feet against the floor with one hand, forcing her

buttocks high into the air. He spanked her upturned bottom with the

paddle and I could hear her sobs despite the terrific noise of the

spanking.

But Mistress Samantha sensed my distraction and was annoyed. Taking the

leather belt her husband wasn’t using she whipped my legs several times.

I began to cry I was so sore but she wasn’t impressed.

“Turn around and give me your buttocks,” she said crossly, and though

it was impossibly difficult, I obeyed. As she beat me, however, I could

gain satisfaction from watching Jill being punished.

Jill was quite beautiful, I thought. She was standing now, completely

naked, hands behind her head. The Master was slapping her breasts again,

and as she stood there trembling under the blows I watched her reddened

buttocks quivering delightfully. I had never seen her punished so

thoroughly before, though I knew I had often been so severely

disciplined. It was wonderful to watch her being punished. As I watched

she thrashed slightly and rolled her head to the side. Our eyes met

briefly and I saw her face flush with shame and she looked away. Her

eyes had gone cold and I knew she would blame the entire incident upon

me, but I didn’t care.

A sudden sharp pain brought me back to reality and I realized Mistress

Samantha was still whipping me. I had been so mesmorized by Jill’s

punishment that I had forgotten. The Mistress was angry with me and

ordered me to grab my balls in my hands and spread my legs wider. I

groaned, knowing what was to come, but obeyed. She whipped me between my

legs, the belt slapping against the tender flesh of my crotch. The tip

of the belt stung my hands and it was difficult for me to keep them

there, but I knew they protected my balls from the belt.

The whipping stopped and I watched as the Mistress and Master exchanged

weapons. Suddenly I was being paddled, and the stinging blows seemed to

ignite the tender flesh between my legs. The Mistress grasped by cock

with one hand as she paddled me mercilessly with the other, ordering me

to jog in place as she spanked me.

But despite everything I could only lust after poor Jill, now standing,

bent at the waist, as the Master whipped her crotch from behind as the

Mistress had done to me moments earlier. Jill, however, was not

permitted to protect her sex with her hands, and I saw her staggering

with sensation as the belt smacked against her naked sex. She was

moaning so loudly it was almost a scream.

I heard the Mistress and Master exchange some words but I didn’t catch

what they said. But the Master stopped whipping Jill and brought her

over to me. Making her kneel he ordered her to take my cock in her

mouth. My heart nearly broke when I heard me say that! At last I would

have relief!

As Jill took my cock I stared into her eyes and saw she was humiliated,

but I knew she’d obey. The Master stood behind her and whipped her to

encourage her, and the Mistress gave me the same treatment.

I came almost at once I was so desperate, pumping my come into Jill’s

mouth. She swallowed it immediately and began again at the Master’s

urging, his whip really stinging her. Desperately she sucked at me, but

even as lusty as I was it took me a moment to get ready again. It didn’t

bother me–I wanted to take my time–but Jill was frantic and I could tell

she was angry that I wasn’t ready immediately.

When I had come a second time I expected that to be it, but the Master

insisted on a third time, and Jill wept in misery as she began yet

again, knowing full well that this time I was almost sated and it would

take longer to revive me. She pressed her breasts against my legs and

ran her tongue around the tip of my cock, her hands caressing my legs.

No question, she was good.

But the Mistress still paddled me, not especially hard, but I was so

sore that every blow really hurt. She struck me randomly, catching me

off guard. I couldn’t get into a rythm, and that confused me. I was so

exhausted that I was almost past caring. Nothing Jill did could revive

me.

But then the Master said something to Mistress Samantha and the

paddling stopped. He reached down and lifted Jill’s legs off the floor

and she wrapped her arms desperately around me to hold herself in place.

She was now stretched out flat in front of me, her mouth still holding

my cock, her hands digging into my buttocks to hold herself up.

I could see Jill’s gorgeous rump in front of me, swollen and scarlet

from punishment, and that aroused me slightly. As she wiggled to suck me

her bottom gyrated and I lusted after her mightily. Then Mistress

Samantha stepped forward and began to spank Jill with the wooden paddle,

spanking her almost as hard as the Master had earlier.

Jill was so shocked she actually dropped my cock for a moment and she

writhed under the paddling. Crying desperately she took my cock back

into her mouth and began to suck frantically, her body arching and

bouncing under the paddle. Watching Jill’s face as she was punished was

fantastic. Her dark eyes flashing with fear and passion, her lips spread

on my organ as she clung to me and sucked with every part of her.

I was hard at this point, but still far from orgasm. I was just too

exhausted. But Jill seemed to realize what turned me on and so she

arched her back and thrust her buttocks into the air to receive the

Mistress’s paddling. Though it must have been excruitingly difficult for

her to do, offering herself like that, it filled me with passionate

desire. Watching those round orbs trembling under the blows finally did

it and I came in huge, slow bursts into her mouth, almost choking her

with the volume. Mistress Samantha didn’t let up at all but continued

the punishment until even after I had finished, allowing me to relax and

really enjoy Jill’s spanking.

I don’t remember much after that. I was bound to the wall inside the

Master’s bedroom, my wrists and ankles firmly tied. Mistress Samantha

put a cool ointment on my sore buttocks and thighs which felt like

heaven, and her touch served to arouse me and left me hard and desiring

all night long.

Jill was also cleaned and creamed, but she was doubled and mounted

opposite me on a large wooden stand designed expressly for the purpose.

Her wrists and ankles were bound together over her head and her buttocks

were pierced by a large leather-covered phallus that projected from the

stand. Mistress Samantha had coated Jill’s sex with honey, and

throughout the night it would drip and tickle, and as it dried it would

tighten and torment her poor sex.

Jill was also gagged, something that disfigured her face and made her

look even more helpless. Her red eyes glared at me over the wide mouth

of her sex as though I was the root of all her troubles.

But when the Master entered she looked humble and subservient. The

Master took a leather thong and whipped her breasts for a while before

retiring, stopping only when her breasts were almost as red as her

bottom, and the nipples practially bursting.

So we spent the miserable night in the dark, hanging in torment, our

sexes starved for attention, our bodies exhausted. Near us we could hear

the passionate groans of the Master and the Mistress, and that too

tormented us, because we were not a part of it.

But despite the ache in my cock and the hot tingling of my thrashed

buttocks and thighs, I was happy. In fact, I was more than happy, I was

ecstatic. This was because the Master had discovered from one of the

cook’s that Jill had been forcing me to do all her work. As punishment

the Master had decreed that I was promoted to escort, and it would be my

duty to ensure that Jill behaved properly. Even better, for the next

week she would be required to do all my work in addition to her own, and

the Master was adamant that I should be extra generous with her

punishment if she failed to meet her quota. I was looking forward to it.

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