Simon and Sir

By MaineboyXY

Published on Oct 20, 2023

Gay

Simon And Sir, Ch.5 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 Five
By
MaineBoyXY@yahoo.com
(for story list and FAQ, go to maineboyxy.freewebsitehosting.com)

I was in agony by the time he returned.  I hadn't gone to the bathroom since the previous morning, and the pressure in my bladder at the pit of my gut was excruciating by the time I was able to make out a slight lessening of the darkness.  There were no perceptible shafts of light, just a faded glow that welled up from the floor, presumably leaking through the crack under the door.  It would have been invisible to anyone who hadn't been tied up and gagged in the pitch black room all night, but I had.  I suffered silently even after I heard sounds of activity beyond the door, sounds of other doors opening, sounds of water in the pipes.  What would the penalty be for losing control?  For pissing all over the bed and myself?  I didn't know and that, as much as the humiliation I'd feel, kept my mind singularly focused on my cock.  I had locked my ankles together, clamping my thighs, and was sweating slightly.  I was glad, for once, for my hard on, because it helped me dam the flood.

The door opened at last, and he stood there, his bright blond hair now darkened with dampness.  He was naked, silhouetted against the sunlight that made me close my eyes reflexively, and reopen them only to narrow slits.  He recognized my predicament instantly, chuckling openly.  "I guess you've learned that lesson, haven't you?"  I nodded and grunted enthusiastically in affirmation.  "From now on, when I offer you some relief, you'll leap on the opportunity, rather than let it slip by, right?"  Again, desperate nods.

He walked over, a finger over his lips to indicate silence, and began unfastening my gag.  As he pulled the phallic plug free, I licked my lips in the instinctive reaction to the liberation of my tongue.  I closed my mouth to swallow and winced as my jaw cramped.  He reached down and massaged along my jaw line with both hands, moving from chin to either joint, stopping by my ears to rub firm circles with his fingertips.  He told me to open and close my mouth slowly, which I did repeatedly as he massaged.  When the ache lessened, I looked away from his soft blue eyes and looked over his body.  I turned my head to see his package again, and he snickered.  I looked back up at his face to see him smirking at me, knowingly.  He stopped massaging and climbed onto the bed, facing my feet.  He straddled my face and lowered his hairless ass to my face.

I licked his crack, smelling and tasting freshly cleaned, a hint of soap still hiding in the pores.  He leaned back, enjoying the rimming.  I teased his hole with my tongue, licking tight circles around the perimeter of his tight, virgin hole.  It was no surprise that his ass had never been fucked, and I didn't even register the fact the night before when I'd eaten him out as he removed the clothespins.  He was wholly a top, and the physical evidence just supported what I knew from his sexual aura, that nothing more than a tongue had ever entered him.  I started flicking his hole with the tip of my tongue, then slowly pressing it barely into the warm pucker, only suggesting penetration before I pulled away, paused and repeated.  It was a dangerous game, playing with my top, but I felt rebellious after having been tied up since early evening the previous day.  He'd let me cum once, a gift I should have seen as generous, but he'd cum once in my mouth and thrice in my ass.  I realized that I hadn't eaten since yesterday's lunch either, nothing except the cum he'd fed me or I'd sucked off his cock when he pulled it from my hole.

Suddenly, though I hadn't thought of eating till then, my stomach felt empty and gurgled.  He reached between his thighs and gripped my nipples tightly in his fingers.  "See, Simon, your stomach wants you to eat my ass properly," he said sternly, tugging and twisting my buds.  I yelped between his cheeks.  "So get to work and stop fucking around down there."  I willingly complied with the order as he continued to alternately squeeze and flick the rock hard nubs rising from my pecs.  I thrust my tongue deep into his tight hole, fucking him with more than sexual hunger.  I relished his clean ass.  I knew I loved servicing him, I knew I loved the way he hurt me.  He never gave me more than I could take, even though he had pushed me farther than I had thought I wanted to go in the past twenty-hour hours.  Hell, I'd kept from cumming for nine days to be with him, on his terms, at his mercy.  His sexual prisoner.  Naked, mostly hairless after the depilatory, often gagged, forbidden to cum except the first time he fucked me, tied to the bed with leather cuffs and straps.  The clothespins, tit clamps, paddle.  The ball stretcher, dildo, cock gag.  And his cock.  His ass.  His balls.

He was flexing his hole and rocking gently over me as I licked and slurped till my tongue was sore.  He leaned over and gently rested his palms on my abdomen, and slowly rocked light pressure over my stretched bladder, filled to bursting.  I cried out in surprise.  No more than a few pounds of his weight were added to my gut, just enough to add to the pain.  He rolled them from one hand to the other in waves as the heels of his hands pressed midway from my navel to my cock.  I groaned pitifully, but without hope.  I knew better.  "Eat," he reminded.  I raised my head again and licked up and down the length of his crack, then buried my tongue into his hole once more.  It lasted only minutes now, maybe five to anyone but me; my world was only ass and the dull pain.  He rose and turned, holding his cock up to his stomach.  He lowered his nuts into my mouth and I bathed his sack.  I slurped greedily, licking, sucking, glad to taste them, glad to service him, glad he had removed some of the pressure from my bladder.  He shifted backwards, then held the head of his cock down.  "Lick, but don't suck," he ordered.  I moved my face up and around tongue out, lapping at the hot, humid knob.  Precum had oozed down from his slit, and I licked it up and flicked over the slit and corona.

He rose and climbed off the bed, and hastily unfastened my wrist cuffs.  "Up," he said, "but don't speak."  I sat stiffly.  How long had I been tied to the bed?  Since the icy shower the night before, the icy shower after the pins and his blowjob.  Ten hours?  Twelve?  I stood but found I couldn't straighten up, the ball in my guts too tight.  I had to piss, very soon.  I felt like I was waddling as I followed him into the bathroom, but rather than raise the lid on the toilet, he motioned me into the shower.  I climbed into the tub and he followed.  "Bend over," he instructed, and I complied.  He took something and wet my chaffed hole.  He'd fucked me long and hard last night, three times, and the last of the cum and lube had dried away.  I felt him wedge the tip of his cock into my hole, not penetrating, but held with pressure at my now slick entrance.  He slid the shower door shut, then turned on the water, adjusting the temperature to a soothing warmth.  He wrapped one arm around my waist, and I knew what would happen.  He pulled me upright with his free hand, pulling me up into the cascade, and wrapped it around my chest.  The cum was washing from my hair, face, and chest, and sheeting down my hairless crotch and thighs.

Firmly, with determination, he moved to me as he pulled my waist back.  My bladder resisted, and then his cock began to enter.  I gasped at the penetration, then groaned at the fullness.  As he sank into my guts, I found myself being pulled into him.  When he bottomed out, buried to the hilt, I was tight against him, my upper ass and back against his crotch, abs, and chest.  There was no escape from the arm around my chest or the arm around my waist.  The water, the pressure, the insufferable need to piss, but my prostate was in cum mode and my cock was hard as rock.

"Oh, Je.." I almost cried, choking back the word at the last second.  Nothing coherent, nothing intelligible, that was the rule.

"Let it go," he said, and he pumped his hips into me.  I emitted something like a groan, something like a grunt, something like a whimper.  I grabbed at the tile with one hand and the glass of the door with the other.  There was nothing to brace myself against, so I leaned forward to the wall beneath the shower head.  "Let it go," he repeated.  His lower hand made a fist, and his arm slid back.  He pressed his fist with slow but mounting pressure in the center between my hips, between my navel and cock.  "Let it go!" he ordered loudly, punctuating with a hard jolt with his cock.

It was too much.  Too much pressure and too much piss, and my prostate and hard cock couldn't hold it back.  It began with a weak trickle that burned its way through my cock, but immediately erupted into a forceful stream.  My breath caught in my throat as my body convulsed.  It felt like an orgasm.  My lower body was clenched, my hole clamped, and I fought against his upper arm to double over.  I couldn't breathe as the piss jetted from my hard cock.  I could manage only shallow gasps as the feeling of unending climax filled me, pouring up from my cock and prostate.  In a normal orgasm, cum ran out after a dozen shots, but my pent up piss kept flowing, splattering against the tile, washing down with the warm water to our feet, and whisked out the drain in the floor.  The flow through my prostate, through my cum tube, and through the lips of my engorged head, was incredible.

He fucked me through it all.  Holding me erect, maintaining the frontal pressure on my lower abdomen, never relenting in the assault on my prostate or internal battering of my bladder.  When the flow began to ebb, I slacked, almost limp in his arms, head back against his shoulder, panting.  My cock was still hard as the piss diminished to a trickle, then only dribbles caused by his rapid ramming.  I weakly reached behind my neck, loosely wrapping one hand in his wet hair as he fucked.  The other pressed against the shower wall in front me, helping keep me standing on my shaky legs.

He fucked me for a long time.  His strokes were long and firm but leisurely, his cruel purpose fulfilled.  I leaned forward again, despite being nearly spent from the whole of the sexual experience over the weekend, the restless night, the intense sensation of pissing while hard and being fucked.  I leaned forward, both hands on the shower wall as he released my chest, and I rode his cock, meeting his thrusts, impaling myself on him.  We were a partnership, committed to satisfying him for what was at least the fifth time in twenty-four hours.  Since 3:30 the afternoon before, when my adventure had begun.  He again moved his hands to my nipples and abused them as the hot water washed over us.  My lust went on unabated and unfulfilled, my senses devoted to him as he pressed into my prostate and beyond, pulled back, and did it again.  Countless times.  I couldn't cum.  I had no thought of cumming after the orgasmic expulsion of urine.  My hard cock waved erratically in front of me.  He thrusted.

He came inside me like always, his hissing breathlessness behind me.  He soaked in my ass until he softened, then pulled free.  He backed away from me, leaning back against the tile at the far end of the shower.  I turned to him and took in his entire body.  He was so fucking hot.  His hair was mussed, the golden color wet to rich honey, his chest with its casual definition, his trimmed pubes, his long, thick, softened cock slimed with his cum.  I looked up to his face, relaxed, and ours eyes met.  "Do you want it?" he asked, indifferent.  I looked at it and licked my lips with a firm nod, then sank to my knees and sucked him clean.  He lay back against the cool tile and I licked him and took him into my mouth and bathed him with my tongue.  I did the same to his balls before he put his hands on my shoulders to indicate that I stand.

He moved past me into the waterfall, now growing tepid, and rinsed off, soaking his hair.  He stepped past again and slid open the door.  "Wash, dry, dress.  When you're done, you can speak again," he said as he stepped down onto the bath mat and closed the door behind him.


My clothes were on the counter by the sink when I stepped out.  They were folded as I had left them by his door when I'd stripped off the previous day.  On top of the pile was a butt plug.  Not too thick or long, pretty average over all.  He'd said dress and he'd left it with my clothes, so the implication was obvious to me.  I slid it in.  My jock strap was gone, the one I'd used to keep my erection in check, so I pulled on my jeans and shirt and went into the hall.  The smell of food wafted out from the kitchen, so I moved in that direction.  A plate with scrambled eggs, toast, and bacon stood on the counter top beside a tall glass of grapefruit juice.

"Simon?" I heard him call from the dining room.

"Sir?" I answered back, ducking my head into the room where he sat in a long robe behind this week's edition of the same foreign news magazine he'd been reading when we'd met.

"That's your breakfast in the kitchen.  You can bring it in here.  Silverware is in the drawer by the sink."

"Thank you, Sir," I replied.  I collected my breakfast and utensils and returned.  His empty plate and glass were pushed to one side.  I didn't know where to sit at the oblong table.  He folded down a corner of his magazine to look at me, his eyes smiling as he saw me looking at the five empty chairs indecisively.

"This one," he said, nodding to the empty place at his side.

He put his magazine down and watched as I walked over.  "Did you put it in?" he asked.

"Yes Sir."

"Good boy.  You're smart and adorable, and I like that."  My chest swelled.  I laid my meal on the table and sat, and jumped as the plug firmly nudged my prostate.  He snickered.  "I picked that one out just for you.  It's the perfect size, isn't it?"

"Uh, yeah," I said, squirming.  "Yes Sir," I corrected quickly.  He looked around the corner of the table, in my lap, to see my cock tenting my jeans.

"I kept the jock strap.  You won't need it for a while.  You're not going to wear any underwear between now and the next time we meet."  I had picked up my fork and had a bite of eggs halfway to my mouth.  The meaning of his statement was crystal clear.  I turned, stunned.

"But what if I get hard?"

"You will get hard.  That's the point.  You'll be wearing that plug.  You can take it out once a day for half an hour.  I assume that will be long enough to go to the bathroom and hit the communal shower.  If it weren't for the showers, I'd only have given you fifteen minutes a day.  It's thin enough that it won't stretch you out -- because I like you tight," he grinned, "but it will keep you ...attentive... throughout the day."

"But I'm not out!" I protested.

"Having a hard on in your pants doesn't make you gay, Simon," he scowled.  "It may be humiliating, but it's not necessarily gay."

"The plug is!" I whined.

"Yes, but no one will see that.  I know you don't have a room mate in your dorm, and I don't think you walk around bare assed anywhere else."  He was visibly impatient with my resistance.

I looked down at my plate.  He was right.  It wouldn't out me.  It would just humiliate me.  To death?  I knew I was on cum restriction.  My mind would be full of what he'd done to me this weekend, and fantasies of what he would do to me the next time we met.  Hell, it already was.  I'd have the plug in my ass as a constant reminder, and every time I sat down, it would press mercilessly against my prostate.

Nothing bound me to him.  He had no blackmail; he didn't coerce.  His entire demeanor was exactly the opposite, in fact.  He invited my defiance, he pushed me to the edge, he wanted to see where I would draw the line in trading my own wishes and preconceptions to indulge my lustful cravings.  For him.  My submission was voluntary.  I had applied the cream to remove my body hair.  I had refused to jerk off for nine days because it was his order.  I had held on to the stress ball through all the torture.  Because I wanted him.  Because I delighted in the way he used me and the way his use of me pleased him.  Nothing had forced me.  Nothing would force me.  If I agreed to keep the plug in my ass, if I freeballed until we met again, it would be my own volition.  I could stop whenever I wanted to stop, but I knew that if I agreed to it now, I wouldn't stop.  Not until he told me to.

I pushed the thoughts from my head of laughing, pointing students, snickering friends, the rude remarks that would inevitably follow at school.  I thought about how he looked, naked, how he looked clothed, how he looked sitting there in his deep blue robe that matched his eyes.  I wanted to look at him, but I couldn't bring my eyes to his.  I stared at my plate, the food growing cold, the food that he had made for me.

"Yes sir," I said.  And I ate.

Next: Chapter 6


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