Simon and Sir

By MaineboyXY

Published on Mar 6, 2023

Gay

Simon And Sir, Ch.10 Disclaimer and Legal Stuff: Don't read this if you're not supposed to, either because you live in a regressive community or you don't like erotic stories about gay sex (in which case, why are you here?). If you distribute this story, that's fine, just don't edit it, and leave my name on it. Thanks.

Simon And Sir
Chapter Ten
By
MaineBoyXY
(for story list and FAQ, go to maineboyxy.freewebsitehosting.com)

I know now that hours passed.  Panicked struggle faded with exhaustion to resignation as the itch cream he had spread over my cock, balls, perineum, and ass built to its climax and then, slowly, excruciatingly, waned.  All the while, the latex cock gag filled my mouth, the vibrating butt plug filled my ass, and the looped cut of electronica filled the room.  I lay limp in every sense of the word, barely conscious, my arms still stretched apart by the wrist restraints attached to the upper corners of the bed and my legs pulled apart and up, tethered to the wooden block affixed to the ceiling.  My begging and cursing, muffled by the gag, had gone unheeded, and it had dissolved into plaintive moans and then to whimpering, and now to silence.

There had been a time, while my muscles were just beginning to fail after the uncounted minutes of frustrated, futile resistance, when the itching on the outside of my skin and the vibrations rippling through my prostate from the butt plug had brought me to the edge of climax.  I had reflexively contracted the muscles in my groin, making my cock bounce, in the useless attempt to bring my cock into contact with anything, craving some delicious friction to assuage the itch.  The repetitive sensation only added to the itch and the vibration, and my panic grew in that instant when I realized I might cum.  I knew the penalty for shooting without permission:  I would be photographed exactly as I was, and those photographs could be used however he wanted.  Pictures of my current predicament would have had horrific consequences.  I was bound to the mattress, a butt plug clearly visible in the cleft of my ass between my uplifted legs, a cock gag in my mouth, and dried cum all over my face – the load he’d jerked from his own cock to deny me the chance to please him.  And there would be the fresh cum, too; fresh cum that I’d shot all over my chest as evidence that I had been aroused.  If he sent that email to my parents, or my friends, or anyone I knew, I would be ruined.  So I had had to fight off the orgasm as well as the itch.

So I hung limply when he returned.  As ever, his approach was silent.  My eyelashes had been sealed together as his cum had dried, so when I felt the pressure of him sitting on the bed, I could not look at him.  I felt the warm, soft wetness of a washcloth as he cleaned my face.  When I could finally open my eyes, I looked up at him, expecting a face stern and unrelenting.  I was surprised to find that, while his brow was furrowed, his eyes were not hard.  He had dressed after he had left me, and he now wore khakis and a richly green polo shirt.  I glared up at him as I pictured him acting so casually during my torment, probably watching television in the living room or, worse, listening in the adjacent office.

“Don’t make me do that again,” he murmured softly as he looked into my eyes and brushed a lock of hair from my forehead.  The tone of his voice made my anger and nascent hatred dissolve.  He wasn’t ordering, he was imploring.  My eyes widened as they read his; he hadn’t dressed casually and idly waited while the cream wore off.  He’d dressed and fled.  He may even have left the apartment, unable otherwise to resist the temptation to free me before the cream had run its course; with his quiet tread, my single-minded concentration on the itch, and the ambient soundtrack of torture, his departure would have gone undetected.  

His face still reflected his internal conflict between resolutely punishing me for disobeying his order to keep my crotch completely smooth and pardoning my transgression, or moderating the premeditated intensity of the punishment.  “The lesson has been learned, right, Simon?” he asked quietly.  I nodded.  The relief was obvious in his smile as he rose and knelt on the bed.  He first turned off the vibrator and slipped it gingerly from my ass.  Laying it on the mattress, he then stood and freed my leg restraints from the wooden block.

He climbed down from the mattress and kissed me on the forehead as he unfastened my right wrist.  “Finish taking everything off and then hit the shower.  I think we’ll take it easy for the rest of the night,” he said as he backed away.  He moved to the armoire, switching the light from red to standard incandescence.  I reached over and unbuckled my left wrist, feeling the soreness in my right arm, as he moved to the corner and deactivated the little black box that controlled the music piping through the speaker system.

A muffled shriek issued from my raw throat as I tried to sit upright and unfasten my wrist restraints, pain shooting up through my abs and thighs.  He turned in alarm, instantly took in the chafed skin on my wrists, and discerned the problem immediately.  “You fought it hard, didn’t you?”  He moved to the bed as I nodded and he laid his hand on my abs, stroking gently.  My cock stirred to life at his touch.  “Why don’t you get the gag and I’ll get these then,” he suggested, moving to my feet.

My fingers unclasped the straps of the cock gag behind my head and pulled it free.  I slowly worked the stiffness from my jaw after I removed the latex.  I saw him frown at the chafed skin on my ankles beneath the now-removed cuffs, and then he sat down beside my head again.  He rubbed each side of my face over the mandible, and I could see the unspoken apology in his expression.  He couldn’t say it.  Neither of us would let him.  It was his place give the orders and mine to obey; but I had disobeyed.  I had earned the punishment and, even though I had hated him through it, the guilt he evidently felt only made me feel that much more ashamed of what I had done.  There was only one way to break the tension.

“I’m sorry sir,” I whispered hoarsely.  “I won’t disobey again.”

Surprise flickered across his features and then he grinned slowly.  He leaned over and kissed me.  I closed my eyes and slipped my hand into his hair as I tasted him greedily.  Too soon, he broke away and rose.  “Let me help you up,” he said as he took my hands and pulled me to sit on the edge of the bed.  I grimaced as he slipped his arm around my shoulders and pulled me to my feet, my legs numb and weak from all the futile kicking.

“Can you take a shower?” he asked as we headed to the bathroom.

“Yes sir,” I nodded.

“OK.  Take as much time as you need,” he invited as he left me at the bathroom door.


I stood motionless under the cascading water, feeling the hot, pelting stream rejuvenate my sore and tired flesh.  Only when it turned tepid did I begin to lather and bathe, scrubbing the last vestiges of cum and cream and sweat from my body.  The water was nearly cold when I turned it off and slid open the shower door.  I took the towel and dried, then stepped out.  I expected to find the jock strap and the butt plug waiting for me on the sink counter, but instead found a pair of his boxer-briefs neatly folded.  I derived a sensual pleasure in pulling the brushed cotton up over my legs and feeling my package settle into the pouch that usually cradled his genitals.  The loose knit boxers I always wore didn’t cling so tightly to the skin, and I relished the new, form-fitting feel.

I looked up to the mirror and saw his reflection as he leaned against the doorjamb, smirking and watching.  “You look good,” he said.  He moved forward and tousled my unkempt and still wet hair.  I smiled back and watched as his smirk faded into something less playful.  He sucked his lower lip between his teeth as his hand moved from my hair and the back of his fingers grazed the day-old growth of beard on my cheek.  He watched his hand as it moved under my chin and along my jaw line.  He stepped behind me, his hand loosely clutching my throat at the Adam’s apple.  He bent his face to the juncture of my neck and shoulder, below the dark bruise he had left above my collar line the night before.  I felt him lick, then bite, first gently but then nipping with firmer pressure.  I gasped and tilted my head, exposing my skin to him.  He tightened his fingers on my throat slightly, and I watched his hair in the mirror as he mauled my neck and shoulder, then closed my eyes as his free hand gripped my cotton-clad package.

He ignored my cock, which quickly swelled to full erection despite the tight fabric.  He juggled my balls in his fingers and I felt him pull his crotch tight against my ass.  Suddenly, his fingers were gone and his mouth vanished from my neck.  I opened my eyes just as his thumb pressed against my jaw to straighten the angle of my head.  His eyes met mine in the mirror.  “Don’t move,” he ordered.

He released my throat and opened the mirror to reveal the medicine cabinet.  He pulled out a razor and shaving gel, setting them on the counter.  He turned on the water and stopped the sink.  He rinsed his hand in the water and brought it to my face, smearing the moisture over my cheeks and chin.  With both arms reaching around me, he sprayed the gel into the palm of one hand and dribbled water onto the glistening mound with the other.  He dipped in two fingers and raised them to my face.  His six additional inches of height made it easy for him to watch what he was doing over my shoulder, and I could feel the firm, hot pressure of his chest and abs against my back as he worked, and the slow growth of his erection pressing into my ass.

He massaged the subtly mint scented lather into my face in small circles.  In spite of my long shower, the water was still sufficiently warm to be soothing.  I found myself leaning back against him.  When my beard and upper lip were covered, he washed the remaining lather from his palm and picked up the razor.  He pulled gently on my ear to tilt my head to one side, and then he slowly, deliberately, scraped the razor over my cheek, clearing a swath of stubble and foam.

He repeated this again and again, holding the razor in one hand and gently moving my head with the other, until the lather and stubble had been completely removed.  His eyes had followed his hand as he shaved me, and my eyes had remained on his, and ours had met solemnly each time he ran the razor through the water to rinse it.  Finished, he daubed away the rest of the shaving cream with a washcloth.  He unstopped the sink and replaced the razor and gel in the medicine cabinet.  His hands paused indecisively over three tubes of balm, and I felt him lean in and breathe gently beside my cheek.  He then picked one of the tubes and closed the medicine cabinet.

He opened the tube and squeezed some of the balm into his palm.  He rubbed his hands together slowly as I watched, then our eyes met again in the mirror as he raised his hands and stroked the substance into my skin.  I instantly caught the subtle scent of orange and jasmine, a scent I’d never detected on him.  Our eyes remained locked in reflection as he leaned in again inhaled the smell of my face.  As he pulled away, he smiled.

“Don’t close your eyes,” he ordered as he slipped the elastic waistband of the boxer-briefs he’d leant me down, tucking it under my scrotum.  I looked down as he squeezed more balm into his hand.  “Keep looking in the mirror.  I want to see your eyes, Simon.”

I gasped at the cool tingle as he closed his fist around my cock and began to stroke.  My lips parted as, still looking into the mirror, he began to nip my earlobe.  His free hand rubbed slowly and softly over my chest, starting at my pecs, and then moved lower over my abs, until he pressed firmly into the middle of my hips, centered between my navel and cock.  He began to grind his own erection into my ass as he continued stroking, maintaining a smooth, regular pace.  “Cum for me, Simon,” he whispered into my ear, and I shivered at his breath.  He snickered and licked at it.  My hands, which had hung limply at my side, moved back to his hips.  He stopped fisting and moved his hand to the end of my dick, firmly rubbing my knob in the curl of his palm.  I gasped again, groaning loadly, and leaned forward with my hands on the sink counter, trying to pull my crotch back away from his hand, but I was stopped as my buttocks pressed harder into his groin.

“Cum for me, Simon,” he murmured again more loudly.

“Yes sir,” I whimpered.  He resumed his rhythmic stroking as his hand moved still lower and he began to play with my balls.  It had been almost twenty-four hours since my last orgasm as he had fingered my cock head with his thumb.  He’d fucked my ruthlessly over the back of the couch in the hotel, then over the anteroom desk, plowing his load into me while my balls had been leashed to my neck with his necktie.  Since then, I’d nearly cum once while I impaled myself on his cock this morning and had nearly cum again through the itching with the vibrator in my ass.  Now, after the long, salubrious shower and the overtly sexual shave, it took only minutes for his handwork to bring me to the edge again.

I leaned back against him once more, and my eyelids slowly closed.  I yelped and jolted upright, eyes flying open, as his thumb and forefinger firmly tweaked one of my nuts.  “I said to keep your eyes open,” he reminded.  “I want to watch you watch me.”  He was smiling evilly again, his face so close to mine we almost touched.  I fought to keep my eyes open as I felt the orgasm growing closer, his hand still pumping in the inescapable, steady rhythm.  He could see the climax approaching from the look on my face.  He turned his eyes away from mine as he moved in towards my ear.

“Earlier, in the grey room,” he spoke softly, “I couldn’t cum without thinking about how good your mouth feels on my cock, and how hot, tight, and smooth your ass is when I fuck you.”

He had been thinking about me when he beat himself off over me, while I was strapped helplessly to the bed during the first, most psychologically difficult phase of my punishment!  He had made me believe he hadn’t needed me to get off, that I was just a toy for him to use whenever he felt like it, but it wasn’t true!  As his fist moved tightly on my swollen, throbbing cock, and his fingers played over my balls, my abs clenched and my fingers balled into my palms, and my eyes fought my conscious effort to hold them open, staring at him biting his lower lip, expressionless, his eyes boring into mine, I smelled the scent of orange and jasmine.  And I came.  My hips bucked against him and my balls pulsed as he stroked them and my cock spewed as he relentlessly fisted it, never slowing his pace.  And I watched him watch my soul split in half as shot after shot of spunk sprayed across the porcelain, and we both knew that he owned me and that I wanted him to.


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