Poor Simon Ch. 08

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Simon meets Mr. Grey
2.3k words
4.55
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13

Part 8 of the 12 part series

Updated 10/29/2022
Created 02/12/2011
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Cruel2BKind
Cruel2BKind
994 Followers

*Hi guys...

This chapter is a little shorter then usual, but I'm not going to be able to work on Poor Simon for a few days so I'm just giving you what I have.

The 'Sexual Intensity Scale' is at a 7.5

All characters are 18+

Thank you and enjoy the following chapter!*

*

I was sleeping restlessly, and for the first time the alarm clock woke me up. The buzzing siren rang through my skull and I jumped.

"FUCK!"

I cradled my bruised skull in my arms, suddenly terrified. Master's hand was on the alarm clock and for a moment we looked at each other with wide startled eyes in the dim light from the bathroom in the hallway.

He started laughing. I let out a weak chuckle, more of relief that he wouldn't hit me then anything, but I was still too betrayed from last night to look at him in the same adoring light.

"It's a bit too early in the morning for such profanity, don't you think so Simon?"

I tried to say 'Yes Master' but all that came out was a hoarse caw. I was losing my voice. The second time I managed to whisper it but my voice was nothing but a foggy memory.

I winced as he turned the lights on. I looked down and I waited for him to unlock the cage. When he didn't, I looked up and it gave me a nasty jolt of anxious surprise to see that he was staring at me fixedly. I bit my lip and I looked down again.

"Do you need aspirin? Or maybe something stronger?"

He was speaking in this strange cautious tone. I realized that it seemed so strange because he was speaking like we were equals. I felt the tears coming again in a hot gritty rush, so I wiped my eyes with the heel of my hand and shook my head, not trusting my words not to waver.

He unlocked the cage and I crawled to the bathroom. There I saw why he had looked at me so strangely. My eyes were dark swollen hollows and my mouth was a weak trembling line and my lashes were matted and sticky. I was very pale.

I had cried far more often then the other boys my age at home. Hell, probably more then some of the girls in my school. I had found ways of hiding the evidence.

I ran the tap until the water was icy cold and I stuck the corner of a washcloth under it. I used the cold water to dab my swollen gritty eyes. When I was done dabbing them clean I did the same with very hot water. When I was done, my eyes looked a little puffy, but nowhere near how bad they had been.

---

I was eating breakfast listlessly when Thomas came to our table with a small white envelope. He saw me, and gave a little sympathetic shrug.

Master ripped the envelope along the seam with his thumbnail and took out a piece of pearly grey stationary. He read it, his mouth pursed slightly with distaste and then he rubbed his temples. I flinched when he looked down at me. His mouth had been open to speak, but when I flinched he looked at me strangely for a moment before going on.

"Eat up Simon." He said quietly. "Mr. Grey wants to evaluate you after breakfast, and he can be rough."

My stomach curled up with fear, and for a moment tears welled up in my eyes. I was so scared, and I was so tired of being scared. I just wanted to crawl into a corner and sleep.

I looked down at the strip of ham and sliced apples. I had barely picked at it, and for the first time here I wasn't hungry.

"Eat Simon." There was an edge of frustration in his voice. "You cannot be like this in a few minutes, or Mr. Grey can make your life hell."

I ate, but the food tasted like ashes in my mouth.

---

I crawled at his side. I was in a sort of daze as we walked to Mr. Grey. The worst thing about this mess was I couldn't hate him. I couldn't hate my Master. By all rights I should've feared and despised him from the start, and now he was breaking my goddamn heart and I couldn't even find a speck of bad feelings towards him. I loved him.

He hesitated at the doorway. It was a plain door with a small steel plate that said 'conference' in the middle. I leaned into his leg, desperate for any kind of contact. A moment later, I felt his fingers twine into my hair; petting me, comforting me. At least he cared. I don't think I could have survived myself if he had disliked me.

"Let's do this." He said firmly. "Obey every thing that we say to the letter, no...no matter how much it hurts."

"Yes Master" I whispered hoarsely.

---

It was dark in the room. The only light came from the half-closed blinds and through the blinds I could see winks of the ocean. A few chains with leather shackles hung from the ceiling, and two men sat in swivel chairs around a long table of dark wood.

Mr. Grey was easy to see. He was wearing a steel-grey suit with a bright red tie and he was looking at me with small black dead eyes. He was a slender small-framed man with a strangely smooth face. He only had two sets of wrinkles, but that word seemed inaccurate. He had deep lines around his mouth that looked like they had been carved, and another set of knife-slash wrinkles around his eyes. His hair was almost completely white, with a touch of dark grey hair in the back. He had small smooth hands that were very pale, and I wondered if he powdered them.

The other man was definitely a bodyguard. He was the biggest man I had ever seen, and as black as a coal shaft. Not brown, like some black people, but actually black. The only places where his skin was a little lighter was around his mouth and the palms of his hands. His head was perfectly shaved and it gleamed like an obsidian marble. He wore a cream-colored suit and a red tie. The muscles on his body strained the tailored suit.

I crawled at Master's feet, feeling sick with fear. I crawled until I was kneeling at his feet, looking at his pointed Italian shoes.

"So this little thing is what the fuss was about?"

I nearly jumped. Mr. Grey was such a small man, almost delicate compared to his bodyguard, but his voice was a deep smoke-broken rasp.

"Yes Mr. Grey." Master's voice was subservient, and it seemed so wrong. "What did the Doctor say?"

Mr. Grey wheezed with laughter, ending with a few deep chesty coughs. "I ain't gonna turn this into a fucking game of tattle-tale like that fucking brat wants me to." I looked up, nearly startled into laughter as he broke into a squealing falsetto, his face never changing.

"Rogan always gets the best of everything! He stole from me! He's a menace to our corporation! (his voice changed back to normal) Blah blah, whine whine. Fucking pansy."

His small smooth-lined face was like that of a cheap doll. I looked back at the carpet, flustered and deeply afraid of this strange little man.

"Well Rogan, it's time to see your little Fish displayed properly."

My Master nodded and tugged on my leash. "Yes Sir."

He tugged me to my feet and told me in an expressionless voice to stand on a chair. I did. He fastened the leather shackles around my wrists. I stood with my arms spread in a Y-shape, supporting my weight on my toes. Master Anthony sat down and Mr. Grey stood up. He couldn't have any been taller then me.

I flinched and looked away as he stood in front of me, his strange dead eyes looking me over.

"You said in your report that he is already turned on by pain and bondage. How much experience does he have?"

I have tied him up three times. He has been sounded once. He has used a one-inch-thick dildo. He has had oral sex with the barbers, three male Fish, and the waiter."

Mr. Grey snorted. "Pretty easy going there. Let's see why the doctor whined so hard about wanting this little scrap. Anyang! Come over here and blindfold him."

The huge black man got up, and though I was dangling almost two feet from the ground we were at eye level. He covered my eyes with a soft black scarf.

My cock twitched a little, just with sheer anticipation. My breath was coming in shallow fearful gasps. I let out a fearful little cry as the swivel chair was kicked from under my feet. I grabbed at the chains around my wrists with my hands to support my weight a little. He just left me there for a few moments, with my arms trembling.

I moaned when the lash went down on my ass. It was hard but not nearly as hard as the brutal whipping I had taken from Master Anthony. It still hurt because it was in such a tender bruised area. Three more lashes, one on my shoulder and one on my belly that made my body curl up defensively for a moment, and one across my knees when I lowered my legs. I tried not to cry out, but even though the lashes weren't excruciating, I couldn't tell where they were coming from. I couldn't stop my head whipping from side to side, trying to tell where the next blow would come from.

By then, the muscles in my arms were trembling and my weird pain-driven cock was perky and slapping against my stomach. I moaned with relief when I felt the padded fabric of the chair seat under my feet again. With my toes holding me up I was able to relax a little.

All relaxation evaporated when I realized that he had thrust two chairs underneath me and that I had one foot on each chair. He wheeled them apart and I stretched my legs so far apart that I was barely supporting my weight on my toes and my genitals were hanging free and my inner thighs were trembling. I was shaped like a big X.

I cried out and nearly lost my support when his hands dived between my legs and roughly held my vulnerable ball sac. This wasn't anything like Master's treatment, gentle and slow, he was wrapping rough twine around the top of the pouch and drew it so tight that my sac must have looked like a bag with a drawstring.

I squealed and every muscle in my body was shaking. He mashed my balls together and my entire groin exploded with hot leaden pain. My stomach became a tiny trembling animal in my throat and I shrieked over and over again. He mashed and un-mashed in a relentless rhythm. With each squeeze, hot pain sunk its teeth in my belly and groin and even my upper thighs. He let me alone for a moment and I sagged a little, clutching the chains for support and sobbing with pain. My penis bounced foolishly.

My nuts felt swollen and full, at least the size of oranges by now. Then I realized that he had only paused to pick up the whip. He gave me four quick smacks between the legs. I screamed so hard that my voice wavered in and out on a high breathless shriek.

When he reached for me again I finally broke. "Oh please stop please no more MASTER!! Please help me!!"

I was begging and babbling and cringing in preparation for more torture, but he didn't touch me. Suddenly, someone's hands were unfastening my shackles. I edged onto one of the chairs so I wouldn't end up doing the splits and Anyang took off my blindfold. As he untied my remaining arm I wiped my tearful eyes. My testes felt swollen and bruised. Master was sitting with feigned nonchalance, but I could see his tight fists, a sure sign of his anger and fear.

I hopped down and nearly crumpled when my balls let out a siren scream of pain. I crawled over to my Master and leaned on his leg, burying my face in the warm firm thigh.

Mr. Grey let out a smoke-broken chuckle. "Cute. You were right Rogan; this Fish is better at withstanding pain then most of our veterans. Does your Fish have any other traits I should know about?"

I trembled as Master ruffled my hair in an attempt to soothe me. "He is very obedient, and is a natural submissive. He responds well to pain and is very good at giving oral sex."

"Oh he is, is he? Well, tell your little Fish to come over and give Anyang a blowjob."

Master cuffed me lightly on the shoulder and I crawled over to his bodyguard slowly, so I wouldn't hurt my swollen ball sac.

"Anyang doesn't like boys, so your Fish will have to work hard."

I traced my fingers over Anyang's thighs through the cream-colored suit. I was still panting and shivering from my rough treatment. I nudged his thighs apart so I could rest between them, and when I looked up his face was stony and bored.

I nuzzled him through his clothes, giving the warm yielding bulge a kiss. Then I mouthed open the button and pulled down the zipper with my teeth. No conscious thought was going through my head. My mind was a pleasant blank besides a determined drive to give this man a blowjob he would never forget.

*

*Sorry for leaving you all on a cliffhanger!

Its optional... but I'm going to do a little survey right here.

Who is everyone's favorite character besides Simon and Anthony? The choices are...

Axel

Kara

Raine

Matthew

Dirk

Mr. Grey

Just put your favorite in the comments section, and thank you for the feedback, depending on what i get, that character might turn up later.*

Cruel2BKind
Cruel2BKind
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33 Comments
AnonymousAnonymousabout 3 years ago

Dirk

wawferwawferover 6 years ago
Fave character

My first is Master Anthony but since I can't choose him I will have to say Axel. I love his personality

poreyb1999poreyb1999about 7 years ago

Going to have to go with axel. He's just so bubbly

Open21andallOpen21andallover 10 years ago
Raine

Because he still has an impishness about him

icefang4436icefang4436almost 11 years ago

XD axel, I find him amusing

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