tagGay MalePoor Simon Ch. 04

Poor Simon Ch. 04


*Hello one and all, this disclaimer is a little longer then usual and I apologize.

Through some technical difficulties, I managed to lose almost my entire 60-page manuscript of Poor Simon and I am now writing from memory so it will take a little longer and I want to thank you all for bearing with me.

In the following chapter, there is gay content, emotional turmoil, forced makeover, and pretty serious Master/Slave dynamics, so if any of those turn you off, scram.

Also, in this chapter there is *Gasps of horror* a heterosexual encounter.

All characters in this account are 18+

As always, this is a fictional account and none of this should be attempted. Make sure any rough roleplay is just that, roleplay. Remember that human trafficking is a real and sick problem and I am just a lonely fag-hag pervert that gets off on it and hopes that you will enjoy it too.

Please tear it to shreds in the comments section so I can make this story better for you, since I am re-writing it, you could even make suggestions, though I am not guaranteeing I will use them.

And as always, please enjoy this new chapter of Poor Simon.*


After a brief nap, no more then twenty minutes, Master woke me up and now we were walking down the hallway. I was naked and on my knees, but I found out that though not even 24 hours had passed, I was already far less conscious about my nakedness. After all of the things that happened to me; it seemed like a very minor ordeal.

We went down the hallway with all of it's mysterious doors, and we stopped at one made of cloudy glass. Through the glass, the walls were soft pink and I could see dim objects and someone moving around.

We went in, and I let out a surprised little laugh. It was a hair salon. There were large padded chairs (sheathed in dark maroon faux-leather) and walls full of hair products. I could see tubs of wax and bottles of shampoo and hundreds of hairsprays.

A slender man in tight black jeans, a black mesh shirt and short black hair in a faux-hawk was sitting at an office chair, filing his nails with a pink file. His eyes were lined with black eye shadow and mascara and I could see an intricate smoke-colored dragon tattoo that covered most of his left arm and shoulder all the way to the smoky-flames designs that covered his left wrist. Looking at him, he seemed ageless, he could've been anywhere from twenty to forty five.

He looked up from his nails, his full red lips in a pout. Then his pale blue eyes widened.

"Oh Tony! He is so ADORABLE!"

He got up and his movements were quick and birdlike and decidedly effeminate. He swooped down onto his knees and suddenly my face was cradled in his warm hands that smelled like ink and scented hair products. His ice-pale eyes were less then six inches from my own. I could feel my skin getting hot and flushed against his hands as I tried to look away, embarrassed and anxious and a little flattered.

"Is your afternoon free? If it is, I think you could get a more intimate setting then this."

I looked up at Master Anthony, shocked. I felt a mixture of excitement and shame and shock and even a little jealousy. I was painfully aware at how familiar this mixture was getting. The man let out an excited squeal, clapping his hands in a very feminine way.

Master smiled, I hated him for how much I loved that smile. "Makeover first Axel, and call Kara in, I want Simon to learn how to pleasure women."

Another shock. My stomach twisted nervously and I bit my lip. Axel looked indignant and pouty. I couldn't help but giggle. He strutted (I blushed at how low those jeans rode on his pale hips, I could see a small heart tattoo just above a tantalizing little cleft) over to an intercom set into the pink wall.

"Yeah... hi sweetie, Tony brought that new blonde kid... yeah I know... you better not steal him from me toots... yeah... mm-hmm... bye hon."

He lifted his hand from the button and patted the surface of the faux-leather chair with a hand that glittered with at least a dozen slender silver rings. I crawled up, and sitting on the leather chair reminded me with a flash of sudden arousal and shame of when I had woken up to Master Anthony. I had been in a chair just like this, only blindfolded and tied up and then he wrapped his hand around my cock...

"Oh, honey... if you keep tormenting me with that pretty little thing I don't think I'll last very long."

Axel was staring hungrily to were my semi-hard cock was sticking from my wispy pubic hair in a weak exclamation point. Him looking at it just made it twitch. I moaned with humiliation, but it wasn't as bad with Axel. Axel was friendly and bubbly and flirty, he didn't have the same sort of hold that Master Anthony had over me.

Master chuckled and spanked Axel, something passed between them and I instantly knew that they had been partners, casual or serious I didn't know. A hurt noise escaped my lips and I was surprised and ashamed at the force of the jealousy I felt bubbling in my chest. Then Kara burst into the room in an explosion of pale blue.

Kara was a short curvy woman with very short white-blonde hair. Everything she wore was blue. Pale blue top, skirt, thigh-high stockings, shoes, even the barrettes in her hair. The skirt was long enough so she could have worn it in public, but her top was unbuttoned enough to see a pale blue bra.

Her eyes (Pale blue) opened wide and she squealed, sounding eerily like Axel. "Oh my Gawd, he is so CUTE!!"

She bounced over, I tried to shrink into the chair. I had given up on trying to make sense of the tangled knot of confused emotions, I just turned my head away hoping to put out the fire in my cheeks by laying it on the cool maroon seat.

Her small cool hand pinched my nipple and I yelped.

Suddenly they both were pulled back. Master had his hand in the laces on the back of Kara's top and (I cringed with jealousy) the back of Axel's jeans. "I love your enthusiasm boys and girls." His voice was cool and amused. "However, I came here to get this fish cleaned up. Only then can you two fight over him."

They put on identical woeful expressions and spoke at the same time.

"Yes Sir"

"Jeez Tony."

I couldn't help it. I started laughing. I laughed so hard that soon I was out of breath and tears were squeezing from the corners of my eyes. I was muffling my mouth with my hands and curled up a little on my side but I just couldn't stop, even when my stomach spasmed with hot cramps, still sore from the workout.

When I finally got myself under control, letting out weak giggles, the barbers were grinning and even Master Anthony had a small smile on his face.

And then they started the makeover from hell.


They both worked on me at the same time. It was very unnerving to be absorbed in turning my head the right way to have Kara trim my hair and suddenly feel Axel clip a toenail. Or to be blushing and looking away as Axel gave me a string of flattering comments while trimming my nails and suddenly yelp as Kara plucked an eyebrow. It made me a little jumpy.

I liked them though. While I was with the barbers a sense of relief filled my confused head and soothed my frayed nerves. They treated me nicely. They made me laugh, they squabbled like siblings.

I winced a little when Axel came from a back room with a tub of hot blue wax. I bit my lip.

"Aw poor little baby. Don't worry Simon, it only hurts a little." Kara was trying to reassure me but I was still panicking a little and I curled my legs under me, trying to cringe from the spatula of hot wax.

"Legs down, hon. I don't want any of that nonsense here."

Axel smeared the warm sticky wax over the tops of my legs from knee to foot. He had a strip of cloth and before I could even tense, he put the flat strip of cloth over my legs and tore a swatch of hair.

"Owowowowowow" I yelped, but he was moving so fast and so smoothly that barely thirty seconds later the area he had covered with wax was shiny and clear of both hair and wax. Tears gleamed in my eyes from the pain, but I reached down to feel how smooth those patches of skin were. The pain also had another effect.

Axel groaned. "Oh honey, you just can't DO this to me." he reached forward and suddenly his long fingers were wrapped around my semi-erect shaft and I could feel the warm metal of his rings. I yelped, but his warm hand didn't stay there for long. Suddenly he was slathering more of that warm blue wax around my crotch, matting the crinkled gingery-blonde hair.

I shrieked a little as the first strip of cloth was torn off, absolutely sure that it had taken a swatch of skin as well. Axel was merciless, tearing off strip after strip so quickly I couldn't react and so painfully I was crying.

After what couldn't have been more then forty seconds (but had felt like an hour) my groin and inner thighs were free of the pale tufty hair that had been growing listlessly since I was about fifteen. My cock seemed bigger without that hair around it, and the pain, as well as the sensation of Kara's hands feeling me over for stray hairs, had it looking perky and erect.

Kara put some baby oil on the soft reddened skin of my groin. Three days ago (had it really only been that long?) I would have been moaning and thrashing with embarrassment and shame to have a girl touching me there. But things had changed, and her hand was soothing and businesslike, at least for now.

The makeover from hell ended when Axel plucked one final stubborn hair from my knee that had somehow evaded his merciless waxing. Kara looked sympathetic and tried to reassure me.

"It wont hurt so bad the next time sweetie, you wont have a full growth and hair always grows back a little smaller and thinner after you pluck it."

Master came forward and picked up the leash from where it had dangled during the Makeover. As we left the room (me on all fours) I glimpsed my face in the mirror, and I barely recognized myself.

I was smooth and naked and slender, crawling like a woman in the dirty magazines my friend carried around. My body smooth and hairless, my eyebrows arched and smooth. My eyes were a little red from crying all the time, but my mouth was full and my cheekbones high and I looked... I looked pretty. I had never seen myself in this way before. Part of me hated that pretty face surrounded by a new stylish haircut. Part of me hated the sensation of my hairless thighs whispering together as I crawled. That part of me was broken and emasculated.

But that was only a part of me, a part that was rapidly fading, weather I wanted it to, or not. I crawled after Master Anthony like a dog, holding back the tears because they would do no good, and trying to convince that fading part of me that I wasn't looking forward to being given to these strangers like a party favor. I was lying.


As soon as we entered room 17, Kara and Axel jumped on the bed and looked at us expectantly. I got a furious shock of arousal and nervy excitement when I realized that Master Anthony might come to bed with us, but he only ruffled my hair and unclipped the leash.

"Go on up there Simon, do what they say."

I shivered, and I felt a sudden longing to touch him. I crawled to the bed and heaved myself up so I was in between the two barbers. Master sat on top of my kennel and proceeded to give instructions.

"Face Kara, you need to learn how to eat her out. Axel, he is to be kept a virgin so use your fingers and tongue, but nothing else.

I was kneeling between these two, being devoured by their eyes. Suddenly Axel was embracing me from the back. They lunged on me together and my head arched and I let out a loud whimpering moan. I couldn't tell whose hands were tugging on my sensitive nipples, or stroking my buttocks. A smooth cheek rubbed against my neck and a rough stubbled cheek brushed my left shoulder blade, trailing kisses down my spine as his hands pinched and caressed my ass.

My head rested on Kara's shoulder, I was overloaded with the sudden sensation of Axel's teeth nipping at the sensitive area just above my crack. She cradled my head in her hands and suddenly a perky pink nipple was an inch from my face, cresting her small, firm left breast. She caressed my head in her small hands.

"Bite it sweetie" she purred, "Bite it hard."

I cried out and lunged forward as Axel hungrily lapped his tongue from the base of my scrotum to that sensitive, ticklish dimple at the base of my spine. His hot wet tongue swirled through that tender little sweet spot and my cry was muffled by a mouthful of Kara's firm breast. I felt the nipple in my mouth, hard and insistent, so I sucked hard before giving it the commanded nip.

This time, it was Kara that lunged, almost choking me as I frantically sucked and nibbled at her chest, trying to make her happy and wondering in some dark corner of my brain why on earth strait men enjoyed this. I was also squealing and squirming from Axel's skillful manipulations. He was making hungry noises as he caressed my thighs and hips and ass with his hands and mouth. I loved the feeling of his slick tongue and soft hands on my silky hairless skin.

It's worth it, I thought deliriously, the amazing smooth feeling made the makeover from hell all worth it.

Kara's hand was hiked up under her short blue skirt, working frantically as she continued to let out high-pitched rabbity cries of lust. Out of the corner of my eye I could see Master sitting, smiling faintly but studiously, his eyes sharp, but his hand cupped around the crotch of his dark pants.

I practically yipped with surprise and arousal as Axel spread my cheeks wide and plunged his tongue into my asshole. It was my first intrusion since the first traumatic experience with the Doctor, and easily a thousand times more enjoyable, I was shaking with arousal. I had a brief image in my head of Master Anthony doing this, but the image seemed jarringly wrong. He was my Master, he would never be inclined to touch my so intimately with his mouth. I glanced at him and cried out as my cock twitched in eagerness. The pure taboo of the image just made it more exciting.

Kara cradled my head in both hands and pushed me down. While I had been ogling Master, she had tugged the pale blue skirt around her slim tanned ankles and now was forcing my head into a part of a woman I had only ever seen in neat diagrams in my high school health classes. My brain kept ejaculating the official names of whatever I was putting into my mouth.

Her crotch was neatly waxed except for a thin strip of closely trimmed white-blonde curls. Her hand was delicately pushing apart the lips (labia major) to reveal a patch of bright pink skin that was soaking wet (vaginal fluid) and two fingers were gripping a small pink bud (clitoris) and dandling it in small circles with a somehow vicious intensity.

I hesitated, feeling slightly disgusted and rather ashamed at being disgusted by something so natural. Then I dipped my head like a hummingbird reaching into a flower for a sip of nectar. I felt my tongue rub a hot moist slit (vagina) and two wrinkled flaps of skin (labia minor) and then my lips wrapped around her clitoris.

While I was so weirdly fascinated and disgusted by this display of female anatomy, Axel had graduated to gently stroking my cock as he teased my quivering opening with a single finger, nipping and licking my ass cheeks. Kara, meanwhile, was going insane.

"Oh! Oh! OH!! Harder sweetie, suck my clit!"

I was doing my best.

I liked Kara, but she had no appeal for me. I had heard some people say that everyone liked both sexes to some extent, but I felt almost nothing being chin-deep in her crotch. Axel on the other hand...


I writhed as I moaned and I nearly squirmed off the bed with the force of my arousal. His middle finger was deep inside of me, and instead of carelessly jabbing my prostate as the Doctor had, he was deliberately stroking it. Hitting that spot inside of me that filled my brain with hot sparks and made my knees weak and my groin steely and hot. Kara shrieked as my moaning and thrashing drove my face harder into her vulva and made my teeth scrape that sensitive pink lump just a little bit too hard for her to handle. Kara had her first orgasm with me burying my face between her legs and I heard the quiet jingle of keys as Axel dropped his pants.

And that was just the beginning.


I don't know how long my first threesome lasted. It could have been anywhere from a half hour to an age, and I would have believed it. All I know was when it ended.

I had Axel's sperm on my belly, it was cooling, but still warm. Axel and I were naked. Kara still had on her undone top and it hung in limp blue curtains as she squatted over my face, long since soaked with her countless orgasms. She rode my face as hungrily and mercilessly as a predator going in for the kill (in this case, orgasm #5) and I had long since gotten over my weird fascination and I was just working my mouth, mindlessly moving my sweat-soaked body, nearly crazy from my withheld climax.

Axel held the backs of my thighs in his strong hands and had them spread-eagled while his face was in my crotch. Right now he was licking and nibbling my cock, which was bright red with denial and hard enough to cut glass. I was delirious with my need for release. Kara shifted a little and I felt a cold lurch in my stomach as I saw Master standing over us at the edge of the bed. He had the whip in his hand and I saw what he was going to do a brief moment before he did it.

He heaved the whip down on my stomach and my mind flared with bright sudden pain. Every sore aching muscle in my stomach and chest tensed and I wailed into Kara and my cock exploded into Axel's eager mouth. My climax was so intense that I passed out very briefly and when I came to, I was lying weak and dazed on my back. Kara was panting and flushed and primly putting on her mussed-up clothes, Axel was hungrily sucking on my small limp cock, making me whimper with its sensitivity.

Shame came back with a vengeance. Tears filled my eyes. I had slept with two people at once. My parents hadn't been in their graves for a full week and I was here in this bed with a collar around my neck and a grown man's mouth on my cock and my face smeared with a grown woman's vaginal fluid and panting in the aftermath of the best orgasm of my life, with semen growing cold and trickling down my belly onto the sweaty bedsheets. And I had liked it.

I weakly curled into a ball and I started to cry. I cried for my parents and for my self and for what I had become. I cried out of shame and fear, but also out of a simple weariness. I was so tired.

Kara was babbling, "What's wrong with him Tony? Tony! I thought he was liking it..."

"Leave us, I'll take care of this."

I cried harder, I waited for him to whip me, punish me. I even wanted him to, just to snap me out of these jagged, lung-hurting sobs.

Instead he picked me up. He carried me in those strong arms despite the fact that my filthy body was staining his uniform. My eyes were closed but I could still sense the change in light as we entered the bathroom.

He ran the shower water and let my feet sag to the floor.

"Hold onto that bar for a second, then I can help you."

I held onto the steel bar set into the wall and the hot spray pounded my trembling body. Through my tears, I could see him strip, see a dim blurred outline of his beautiful streamlined body and dark blurred patches of hair.

I cringed when he stepped into the huge shower stall, still sure that he would punish me. I slipped but he caught me before I fell. My face was pressed into his wet wiry chest hair for the briefest of moments, and that moment was like a sliver of heaven.

He washed me. he washed my body with the detached tenderness of a nurse washing a patient. His hand held the big white bar of soap, and as my sobs tapered to sniffles my Master washed me. He dried me with the fluffy towel.

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byCruel2BKind© 5 comments/ 40437 views/ 13 favorites

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