tagGay MalePoor Simon Ch. 05

Poor Simon Ch. 05


*Hello and welcome to the newest chapter of Poor Simon!

The following piece has gay BDSM, serious Master/slave dynamics, emotional turmoil, and an actual plot, so if any of those scare you or turn you off, then scram.

I have decided to devise a 1-10 scale on how rough the sex is in each chapter just to give you an idea. 1 is strait-up consensual vanilla sex with 2 partners, and 10 is out-and-out torture. The following piece is a 4

All characters are 18+

Because of technical difficulties I am rewriting this piece from memory and I am open to suggestions, though I am not guaranteeing that I will use them.

As always, the following submission is a work of fiction only, and none of this is safe, sane, or real, so don't get any ideas.

And with that, enjoy the next chapter of Poor Simon!*


I rested for about an hour, and Master woke me up by a light lash of the whip. Not enough to hurt, but enough to sting a little and wake me up. As always, when I looked up into that face, I felt the pull of his masculine attraction, and the shame of lusting after the man who was keeping me captive. Every action has an equal and opposite reaction.

"Get on the floor Simon. Lunch is here."

I crawled onto the floor and then he got up and went to the door, leaving me by the bed. Thomas was there with our food and he gave me a little wave.

I was instantly curious. Why had he told me to go onto the floor as soon as the door opened? Was it just because it was time for lunch? Or was it because he hadn't wanted anyone to see me on the bed? Was Master doing something embarrassing, or even forbidden by letting me sleep on his bed? I remembered how he had looked around the steam room almost anxiously when he let my head rest on his shoulder, and I wondered.

All thoughts were driven from my head as he came in with a plateful of steaming food and the smell made me lightheaded and dizzy with hunger-cramps. The plate was pile high with pork and vegetables in a fragrant brown sauce, white rice, and some shrimp and vegetables in a different sauce. I had to swallow hard to get rid of the saliva flooding my mouth.

When he sat down on the bed he looked at me and patted his knee. If I was a dog I would have wagged my tail with joy. I crawled forward so I was almost between his legs and I rested my chin on his leg with a soft sigh. I could feel the firm muscle under my jaw. After he took two bites of his meal, he held a sliver of water chestnut to my mouth with the chopsticks and I gratefully took it. We had the meal this way, with him putting tidbits of food in my mouth and me leaning on his leg like an adoring dog. I tried to clear my mind and simply enjoy the experience without the nagging shame and doubt.

I felt a pang of nervous excitement as he reached into the chest, but to my surprise, he took out a bottle of suntan lotion. He saw my surprise and chuckled quietly.

"You're from Minnesota Simon, and you're blonde. We can't leave you looking so pasty-white, not when we have the sun on our side. Your skin is very pale, so our sessions will be short and assisted by lotion at first."

Without bothering to give me anything to wear, he clipped the leash and we walked outside. I was half-blinded by the sun at first, and then I tried to look around. We were on a narrow cement path on the way to a bright blue kidney-shaped pool. The pool was crowded with several masters and submissives and an old Asian man clipping the bushes that surrounded it. The path was also trimmed with strip flower gardens. The island was small and flat and rocky. I could see two other buildings, one small and boxy and plain and the other a graceful white building about the size of a small elementary school. The building we had come from was also white, but a little larger. There was a pier that extended into the ocean and had four mid-sized boats in metal cradles, and a helipad with two large black copters surrounded by a tall wrought-iron fence.

We entered the pool area. Two girls, the redhead from my table and an Asian girl I didn't recognize were in the shallow end of the pool, kissing and writhing in the water as a master and a mistress looked on. Six submissives were on their stomachs on blue mats, their naked backs gleaming with either oil or sweat as they sunbathed. Raine waved cheerily at me from the shade of a blue umbrella and I blushed a little. I was easily the palest person here, even Raine had slightly tanned skin.

His Master, the chubby man with the horn-rims nudged him and Raine skipped over, smiling mischievously (not all the masters made their Fish crawl like mine did). He stood in front of Master Anthony, smiling with his hands behind his back and wearing only a scanty little bikini bottom in a blindingly bright shade of blue.

"Master Paul told me that I could ask permission to oil Simon up."

He smirked at me as I blushed and hid behind Master's legs. I was a little afraid of Raine, I just never knew what to expect.

"Alright Raine, but don't play with him too much, we have plans."

I made a muffled little sound of surprise before I could stop myself and I could feel the blush on my cheeks get hotter then ever. The sun was already baking my pale skin.

"Aw, your so cute! Wanting big bad Master Anthony to use all his wiles on you!" He was using baby talk, and that just made me flush harder. "Come here Kitty-cat, I'll get you all oiled up."

Master bent, and to my surprise he used a small key to open the lock on my collar. Without it I felt strangely naked. I had felt relatively fine moments ago, but only with the collar gone did I feel truly naked. I lay on my back on a blue mat and nervously clenched my hands into fists as he poised himself on his knees with the bottle of SPF 10 sun lotion in his hands. He squirted it into his hands with a coy smile and started rubbing his hands together.

Raine spread the warmed white goo on my chest, gently tweaking my nipples after the lotion made them glisten pinkly. His hands felt good, he wasn't pinching or tormenting me; he was making it into a massage.

He was also very thorough. In summers in Minnesota, I would just slap some lotion on my arms and nose and the back of my neck and be ready, but then again, I was never naked back then.

He had finished my torso and arms and I had rubbed it over my cheeks and forehead and nose. He gave my limp cock a little squeeze and I moaned a little, feeling it give its first twitches of life.

"Definitely don't want to burn this pretty little thing, do we?"

He rubbed lotion very slowly and thoroughly over my entire groin area, and by the end I was flushed and semi-erect despite coming twice today, and once barely an hour ago. Thankfully, he moved onto my thighs and shins before I could get too aroused.

Then I flipped onto my stomach and he carefully slathered every inch of my skin with more lotion. He gave my pale cheeks a little spank as he left, telling me to lie on my belly until I heard the chime go off.

I lay there, and it was extremely nice. The warmth of the sun-baked concrete warmed my stomach through the mat and the equatorial sun baked my semi-protected back and I imagined that I could feel myself tanning. It made me sleepy and my sore muscles enjoyed the intense relaxing heat.

I was dozing lightly and a bell ringed. I turned over onto my back and with a little amusement I saw the others do so as well. Five girls and one other guy were on their backs. The other guy was a big muscular young man with black curly hair that hung to his shoulders and a body like young Arnold Schwarzenegger. I rested my head back down and dozed this time with the stupendous baking heat of the sun on my front, I had never felt the sun on my genitals before... and it was interesting. I hoped fervently that the sun lotion was doing its job. I had always used SPF 30 and I had never actually sunbathed, or exposed such a tender area to the sun.

When the bell chimed again someone's bare foot nudged me. I opened my eyes and the pleasant drowsiness evaporated instantaneously. I couldn't have woken up quicker if someone had dumped a bucket of ice water on me. Master was standing over me, naked but for a black Speedo. My mouth was suddenly dry, and I could feel my eyes greedily scoping out the way his package distended the Speedo, and remembering what it was like to suck on his cock.

"You're burning a little, we're done for today. Come on into the shade."

I crawled into the shade and let out a little sigh of strange relief when he locked the collar back onto my neck. I knelt by his bare feet, surreptitiously eyeing his body. He was sitting on a reclining chair, the canvas held up by the white metal frame was the same color as the umbrellas, a brilliant blue that matched the sea. His skin was a sleek tanned surface interrupted in places by wiry black hair that I longed to touch. Beads of water glittered in his chest hair and down the narrow trail that marched down his flat stomach and thickened slightly as it reached the V-shaped cradle of his hips and disappeared into the tight damp black fabric.

He saw me looking, how could he not? I was staring hungrily, like a starving man would look at a 9-course meal. He reached out and tangled his fingers in my hair. I mewed softly and leaned into his hand, liking the way his hand felt in my new shorter haircut.

"I think we can spare a few minutes before going back inside. Come here Simon."

I crawled between his legs, surprised that I wasn't drooling with eagerness. He spread his muscular thighs and briefly lifted his hips to pull the tiny black swimsuit down to his ankles. I moaned and this time I did feel saliva briefly wet my lips before quickly closing my mouth and swallowing hard.

This time I wasn't in a dark room with tears running down my face and desperately afraid of what he was going to do to me. I had to guess that his cock was around eight or nine inches long, and so thick near the base that his hand could barely encompass the entire width. It wasn't as hard as last time, it still flopped around a little as he shook it in a wordless invitation to begin.

As gingerly as if I was handling nitroglycerin, I carefully rested my hands on his muscular thighs. I was almost giddy with the sensation of touching his sun-warmed skin. I leaned forward and took the thick shiny head of his cock into my mouth, taking him in all the way to a faint circumcision scar. I could feel his pulse in the smooth sensitive skin of his cockhead.

I pulled back to create a gentle sucking sensation, and he groaned softly, looking down at me. I felt like I could have melted with happiness. I started bobbing my head and his hands rested in my short feathery hair as I concentrated fully on my task. Neither of us noticed the Doctor sliding in behind me.

I knew whom the long spidery hands belonged to as soon as they slid around my ribcage, lightly scraping my skin with the nails and raising goosebumps the size of pinheads. One hand grasped my left nipple and twisted hard enough for me to cry out and the other clutched my cock. His hands were cold and clawlike. My body arched into a perfect bow-shape and Masters cock fell out of my mouth. I let out a loud panicky whimper and looked into my Master's eyes, begging him.

His dark eyes flashed and then narrowed with a fury that was intense and cold. As cold as a frost-rimed dagger. Even though that fury was not for me I shuddered. He stood, pulling up the swimsuit as he did in one fluid motion and the Doctor fell away, his face suddenly grotesque with fear. I crumpled between Master's legs and looked back, my vision blurred with the sudden tears of shock and fear. I felt so filthy from the Doctor touching me.

When my vision cleared I was alone. Master was far away, dragging the Doctor by a strong hand wrapped around the man's thin upper arm, and the Doctor squawking with outrage and fear. They disappeared inside the building, leaving me huddled under the umbrella, naked and alone under the mildly interested stares of the rest of the people around the pool.

I stayed there for what must have been about ten minutes but it felt like an age. Without my Master, I felt unplugged, empty, and without direction. I kept expecting one of the other masters or mistresses to come over and take care of me, but everyone just let me be. I was afraid to get up, so I stayed kneeling, looking at the blue mat under my knees to avoid everyone's eyes. My body gave a brief shudder of utter disgust from the memory of those long pale hands touching me. I felt defiled.

I must've jumped about a foot in the air when Master's hand brushed my shoulder. He had changed back into his uniform while he was inside. I looked up at him fearfully and his face was still in that furious cast, but he was beginning to calm down. With some effort he gave me a strained smile and picked up my leash to take me inside. I timidly followed, trying to stay right at his heel. Sometimes I couldn't quite keep up, and he had always been patient, but right now he was so angry that his shoulders were bunched up and trembling and his hands were in knotty fists. He was also walking faster and I felt sick with fear whenever I lagged a little behind.

When we reached our room I was panting with exertion and absolutely terrified. His anger was almost a physical thing in the room. I stayed by his heel, kneeling and looking at the dull red carpet between my knees. My stomach was churning and hot and sick and I was tensed up for him to whip me. I almost wanted him to, I hoped that it would calm him down.

I flinched as he took a deep breath and let it out in a long hissing sigh. I mewed softly as he petted my hair, that gesture that always made me feel better, no matter what.

"Calm down Simon." His voice was no longer choked with anger, it just seemed disappointed and even a little worried. "I'm not angry at you, and I wont punish you for that bastard groping you."

I looked up, completely startled. Had that been... jealousy? Had I heard jealousy in his voice? His voice had always been very calm, with barely any emotion, like a strict teacher's voice, but now his voice was raw with it. I looked up at him for a moment and I was shocked by how *human* he seemed. Not the unreachable stone-hard god-like Master that I had gotten used to.

I couldn't think of anything to say, my heart felt like it was beating a thousand times a minute and I was trembling like a tuning fork. To accurately describe the confusion of emotion that drove these responses would take a lifetime. The only thing that seemed right, was to lean forward and gently lick his hand. The gesture was so submissive and intimate that my heart throbbed with love.

Then I registered the taste. I looked up at him with wide shocked eyes as I tasted the blood on his knuckles. He looked down at me with a trace of his old smile.

"Never mind that Simon, we have some work to do."


Master Anthony went into the bathroom to wash his hands, and that was the only acknowledgment of whatever he had done to the Doctor. Afterward, he spread a little aloe ointment on my buttocks, where I had received a very light burn and my armpits, which didn't even feel burned but looked a little red. I loved his touch, and the warmth of his hands contrasted deliciously with the coolness of the aloe and I shivered with arousal. Not all of my arousal was from the sensation, Master Anthony's touch was special, if Axel or Raine had done this; I wouldn't have been nearly as excited.

He unclipped the leash and told me to get on my hands and knees on the bed. When I was up there, I blushed at the position I was in. I felt a sort of phantom ache in my asshole, and I knew that I wanted him to touch me there. The itch was almost painful in it's wistful intensity.

He opened the toy chest and I gasped and my cock gave a little twitch. I was like one of Pavlov's dogs, ring a bell and the dog salivates, open a chest and my cock twitches. He reached inside and after a little rummaging he took out a pair of handcuffs with soft rubber padding the wristlets.

"Put your hands behind your knees."

"Yes Master."

Putting my hands behind my knees lowered my head until my face was barely and inch above the coverlet of the bed. He fastened the rubberized cuffs around my wrists and it left me in a very vulnerable position with my forehead resting on the bed and my ass in the air. I gasped softly at the next thing he took out.

It was like the ball gag I had worn on my first day here, but instead of a black rubber ball, it was shaped into a very short, very thick, and very realistic-looking rubber cock. I felt myself salivating a little and I wanted to know what it would be like to suck on it. He smiled at my blushing nakedly greedy face.

"You want this, don't you Simon? You want to suck on this nice gag while I use some of my other toys on you, don't you?"

I nodded, no use lying, "Yes Master"

He cupped a hand around his ear, as if he hadn't been able to hear me. "I'm afraid you will have to speak up Simon, ask me to put this gag in your mouth, and to use all of my toys on you.

My cock twitched again, this time with such intensity that I felt it bob against my stomach. "Please M-Master." I begged, speaking a little louder. "Please put that into my mouth... and please use the other toys on me!"

Just speaking it made my body tingle with pleasure and I was blushing harder then ever and trying not to moan.

I did let out a moan when he touched my head, stroking my hair with one hand and putting the fat glans of the rubber dick to my lips. I opened my mouth wide, but the rubber cock was so thick that he still had to push it home with a gentle clockwise screwing motion. Once it was in there was barely enough room for my tongue and I sucked on it nervously as he went back into the chest for more. Sucking on the dick was soothing, almost hypnotizing.

I squirmed with a mix of distaste and reluctant excitement as I saw matching nipple clips in his hands. The clips were silver with small beaded strings hanging from them. He gently tweaked my nipples as I moaned and squirmed. I let out frustrated little cries as he clamped them onto my sensitive nipples. With each clamp, my cock throbbed hotly. I was surprised at how painfully erect I was. I knew that left to my own devices I was five or six strokes from coming.

He wasn't done. He was still bent over and rummaging in the chest. When he straitened up for the second to last time I let out a half-excited half-terrified squeal.

He chuckled softly and I melted at the sound. "Oh yes Simon, I think its high time you experienced something a little more intense then a couple of fingers."

In one hand was a slender red bottle, in the other was a slender glass dildo. The dildo was not anatomically correct, it was about seven inches long, not including a small textured grip, and it was perfectly round and smooth and about an inch or so in diameter. At the very end were a series of textured bumps about the size and shape of M&Ms. He laid the bottle and the dildo right in front of my eyes and I could see that the bottle was filled with some sort of clear viscous liquid and the outside had a bit of white paper where the brand-sticker had been torn off.

The last time he reached in he took out a whip with at least twenty smaller strands. I whimpered with how close I was to coming. He laid his hand on the small of my back and lashed my buttocks with the many-stranded whip. I let out a whimpering yelp through the gag.

It only took four strokes of the whip before I came without touching myself. I sagged on the bed whimpering with the amazing aftershocks of heat in my groin and looking fearfully at Master Anthony.

He had a lively hungry grin on his face. "Bad Simon... Bad Simon to come without permission."

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byCruel2BKind© 6 comments/ 35481 views/ 15 favorites

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