Every Three Months

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He visits mistress, remembers why he started.
2.9k words
4.06
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(Note: Thanks to everyone who's read and enjoyed, and offered positive feedback lately as I get back into writing. I do want to say though, that as I experiment with different ideas, that some of my writing may seem to be be detailed and long. The reason I have for this is that BDSM to me is more about the mental state of the players, than about strict action. A person could be naked anywhere and it not mean a thing, but draw around them a very specific setting, with stakes, and everything changes dramatically. I appreciate that this isn't necessarily everyones style, but its the one I'm choosing to work with in this genre. So if you're looking for a quick toss, maybe this one ain't for you. Always love to hear from folks about turn-ons and scenarios that simply call out to be lavished out in word. Peace!)


Every three months, I take out a couple hundred dollars, and put the crisp bills into a plain white envelope. I traipse across the city to a quaint looking victorian home in a neighbourhood full of identical homes. Passing by minivans and recycling bins lined up neatly at the curb, I can look into picture windows and see families, newlyweds, old guys in recliners watching TV, a taste of every day life. I can see myself amongst these regular people.

Working in a cubicle farm of an office, pushing papers and killing time, I entertain myself with a crew of similarly young single guys at lunch, sometimes hitting a bar after work, or trading in the khakis for jeans and some out of town excursion on weekends. We drink beer, watch sports, chase women, trade outrageous, if not questionably true stories about our conquests and appetites.

But every three months, I make a trip to this quiet victorian home and leave everything behind.

Knocking politely, I'm greeted by a brunette housewife with neatly drawn red lips. She takes my coat while I kick off my shoes, I stand waiting for her to return not saying a word. She's wide hipped, a slight paunch under her blouse, she's the type of woman I wouldn't think twice about if I passed her on the street. Plain and round, seemingly past her days of attracting young guys like myself; someones mom maybe. Her backlit silhouette returns to the hall and stands still.

"Well?"

Looking downward, I begin to unbutton my shirt, pulling it out of my pants. I fold it best I can before placing it on a nearby table, wrestling out of my t-shirt immediately after. Shirtless, I pause, looking up for tacit approval. Silent, but shifting her weight, the woman shows me her impatience. I calmly hurry through my belt, unbuttoning myself, and pushing my pants and underwear to the ground in one swift move. My limp rubbery cock bounces into the cold air. After kicking off the last pant leg, I pick up and drape the rest of my clothes over the side table in the hall. Placing my hands at my side, I cast my eyes downward and wait for inspection.

Click, click, click. She's in heels now. I'm naked

Of all the times in my regular life I find myself without clothing, I struggle for decency. I squirm when the doctor has me bend over and cough, I hold a towel tightly around my waist when I change at the gym, and if I find myself in a group shower with other men, I try and hold eye contact while chatting, errantly tugging at my cock under the guise of washing, trying to make it seem larger. Sex is usually a victory in and of itself, but I don't present myself or linger enough to become a mental picture. My body is a means to an end, just a small part of the identity I enjoy sharing with others.

Standing naked in the drafty hallway of an old victorian home, I have exposed myself in sacrifice to a dowdy old housewife. My mistress.

"Well, Mr. Tiny cock is back. How many dumb whores did you get drunk this month to service your pathetic dick?" Her gloved hand pinched at my drooping penis.

"Two mistress. I did not please them. I used them for my pleasure."

She purred.

The women I sought were meaningless, just hook ups for the sake thereof. I played the game, took them to bed, and did the bare minimum of work, whilst enjoying their effort, and feeling like a king. If I was lucky, I could talk one into taking my load, either swallowing or on their face. The stories between the boys were uproarious, but rarely described the basic jackhammering and cumshot that climaxed the fun, a bored club girl trying her best to pretend she was pleased as she wiped up.

"Of course you couldn't please them with that. Even if you had a 9" dick, you'd still be a useless, selfish fuck. Wouldn't you?"

"Yes mistress," I replied quickly.

"You're a selfish, worthless little boy, aren't you son? Can't please a woman to keep her, can you?"

"No mistress."

"That sad shrivelled dick. You keep getting fatter too don't you? Any of those women could see you right now in the light of day would be repulsed by... this, wouldn't they?"

"Yes mistress."

"Tell me why they would be grossed out by you" She hissed in my ear.

"Because I'm fat and because I have a sad shrivelled dick mistress."

THWACK

Her hand swatted my ass hard, stinging and surprising me. I was trying to give her what she wanted

THWACK. THWACK

"Tell me in your own words you fucking piece of shit."

THWACK

My mind raced, Why am I so pathetic? What can I tell her? The spanking was intensifying.

SMACK

The next blow was across my face, leaving my head ringing and dazed.

"I'm... I.. I have a tiny dick, and I'm fat, and I'm shit at bed, I don't know what I'm doing, and, and, and... I have to make girls feel like shit to fuck me. I'm ugly. I make shit money. I'm a fucking loser, I swear, I'm a fucking loser"

THWACK. The pain returned to my backside.

"Nobody loves you do they?" I whimpered in pain quietly as she whispered in my ear "Nobody loves you because you're a pathetic piece of shit aren't you?"

"Yes mistress. I'm a pathetic piece of shit."

Her heels clicked slowly around me and towards the door to the basement.

"Boy, you need to give penance for what you've done, and you need to prove your worth to me. Now get the fuck downstairs."

* * * * *

The basement wasn't a dungeon, it was just a cold unfinished basement with choppy concrete floors, exposed ducts and wooden studs making up the walls. A raised workbench stood off to the side, various ropes and chains hung in a non-descript fashion around the room. To anyone walking down those steps, they would have just seen an innocently messy cellar - to me, everything in sight was designed to push boundaries.

The first time I had visited, I was new and fearful of my desires. I had struck up a conversation with the mistress online, spoken about the thoughts I had, and what I was curious about trying. She spoke in an understanding fashion, talking a lot about the psychology of her work. I was comforted by the depth of thought she had put into things, and felt comfortable submitting to her. Eventually I was ready to cross the threshold from fantasy to reality.

That first time I had been brought down to the basement I was clothed, she'd suggested I come by in gear I didn't mind getting dirty or torn. I was already anticipatory. I was toured around her makeshift apparatus, and joked with. She was sweet and helpful, putting me right at ease with her, despite our ultimate intent. She suggested I get up on the workbench and try some restraints. I leapt up and stretched out, letting this polite housewife begin to wrap me in nylon rope, as it got tighter and tighter, I began to panic slightly. My responses to her chit chat were becoming more and more stilted, perhaps a bit tense. I tried to remain as chipper as she was, even as I began to feel more confined. Once I was good and tied down, she pulled up a stool and sat beside me.

"For the rest of our time together, I will refer to you as boy, and you will refer to me as mistress understand?"

"Yes, ma- er, ah Mistress"

"Good. Now for today, I want you to honestly answer some questions for me. Think of this as a getting to know you session" With that, she gently put her hand on the bulge in my jogging pants "If I think you are holding back, or not telling the truth..." Pain shot straight up between my eyes as she twisted my cock. I squeaked.

"Yes mistress!"

For the next while, she caressed me to hardness while asking probing questions about my sexual history, my relationships, and my fantasies. She questioned me on how I felt about my body, about being naked, whether I thought about other men. I was asked about the most humiliating moments of my life, what my worst fears were, what weird stuff turned me on I wasn't willing to tell others. She never had to torture my cock again, because I found myself eagerly wanting to tell her everything. She was practically milking me through my pants as I opened up to her in a way I never had with anyone before.

"Now for the last part of our session sweetie, I'm going to need you to wear this gag for a bit, do you trust me?"

The gag had been somewhat unexpected for some reason, I had been tied up for the better part of an hour spilling my guts, but the gag had put me back on alert. I didn't need to be threatened though, I wanted to do what the mistress asked. Mind you, in my current predicament, I didn't have much choice.

"Yes mistress"

She affixed the gag onto my face, and I grunted into it to test its effectiveness. When i drew my attention to the mistress though, my eyes widened and I began to panic, struggling into my bonds. She held up a sizeable pair of medical shears that glinted in the dim light.

"For the next step, you need to be inspected, and for that, those clothes are going to have to come off I'm afraid."

Suddenly everything got real. These were the only clothes I had with me! How was I going to get home? Was this all a ploy? Was she going to murder me? What the fuck had I gotten myself into?! I tried to plead with her through the gag, but could only produce muffled noise.

Straining at the rope, she began to cut up one of the pant legs. Reflexively wanting to escape, I simultaneously realized I was trapped, and was at risk of getting hurt if I struggled while a blade slid next to my skin. I calmed. By this time, she had brought the blade up along the other side of my pants. Every cut was diminishing the hope I had for saving my pants and my dignity on the way home.

She struggled through the rest of the pants before shearing through the elastic waistband and pulling the scraps away. I lay prone, my hard on bulging obscenely at the front of my grey briefs. My eyes watched her intently, but she never bothered making eye contact, simply kept about the business of cutting my clothes off. The insecurity of my situation, was slowly becoming a turn on for some inexplicable reason.

Deftly, for a lady of her size, she lifted a leg up across the table and straddled my thighs, I could smell her perfume and sweat, felt the pressure of her body. She pulled the bottom of my t-shirt down to make it taut, found a notch with the scissors and sliced it up the middle, until the blade poked at my neck. In a flash, my shirt had opened, and I exhaled. With all the anticipation, and sensations, I had forgotten to breath, but being exposed, stripped to a tiny pair of grey briefs - I felt massive relief. And then neediness.

It was then, that the Mistress had finally looked me in the eye, cocking her head as she placed the palm of her hand on top of my bulge.

"Hold very, very still now,"

Her scissors came up the side of briefs, and I heard that delicate crunch of each snip as it tore through the cotton. Done with one side, I felt the material pull away from my body. She looked away as she set blade on the opposite side, before looking at me again. Snip. Snip. Snip. I was freed from the bounds of clothing now, merely covered with a small torn rag of cotton. All Mistress had to do was to bunch up the material in her hand and pull it off my cock to have rendered me naked and defenceless, but she paused.

A sinister smile spread across her lips as I waited. Her hand formed a tight grip around my shaft, wrapping it in what was left of my briefs. Methodically, she began to move her hand up and down.

"You're so pathetic aren't you?"

I tried to nod.

"Every day you get dressed, and you walk out of the house and you put on this character. You interact with people, you wave at the mailman, you flirt with the secretaries, you drink with the boys. You tell women the stories they want to hear so you can fuck, you pay your rent, and you go to sleep thinking you're fulfilled."

Her tone was patient, but pointed, and I could feel the head of my penis getting slick with pre-cum as she massaged it under the cotton.

"But you came to me because you're not fulfilled at all. You came to me because you're a scared little boy, who doesn't know what he's doing, who wants to have everything he knows..."

She firmly grasped my cock, eliciting a guttural moan from me.

"...Stripped away. So you can be naked, and led, and told what is right and what is wrong,"

She began to ramp up her pace on my cock, getting me closer, I tugged at my restraints as my body began to shudder.

"You seek approval, and if you want my approval, you will have to earn it. Now DO. NOT. CUM. DO YOU UNDERSTAND?"

I nodded my head as she continued to jerk me off. With her freehand, she tore off my gag, and I gasped and moaned.

"ARE YOU MY SLAVE, BOY?! ARE YOU MY FUCKING WORTHLESS SLAVE,"

"Yes mistress! I'm -ugh - I'm your slave! PLEASE LET ME CUM!"

*SMACK*

"BEG ME TO CUM YOU LITTLE BITCH!"

I was about to lose it, I couldn't hold back much longer. I had to cum now, but I didn't want to disappoint.

"Please mistress, please let me cum, please, please, pleeeaase. I'll do anything you tell me to. Just please let me cum!"

She looked me dead in the eye, no smile, just malice in her face. She was nearly tearing my cock off now.

"Cum now." She commanded. And I let loose, bucking underneath her, and crying out, trying to catch my breath. I felt every spurt wet the cum rag that used to be my underwear, I felt her squeeze every drop out of me as I came back down to earth.

In my daze, I felt her weight shift off of me as the workbench creaked. As I lay there, she gathered the last shred of fabric on my body, the final piece of clothing that hid my complete nudity, and used it to sop up my mess, before peeling it away to expose my softening penis and matted pubes. Her heels clicked on the concrete floor as she approached my head.

"I want you to think about what you've done today, understood, and I don't want to hear another word from you until I'm done cleaning up." And with that, she took my soggy, shredded briefs and jammed them into my mouth.

I started to breath through my nose as I began to taste my own cum as it mixed with my saliva. I was repulsed and resigned to this new flavour, this new life experience. I could hear a sink off in the distance. There I lay, naked, dirtied, exhausted, bound and gagged by my own soiled briefs - happy for once to be... nothing.

* * * * *

That first experience was enough to keep bringing me back, to be reminded that much of my life was constructed, an artifice, a facade. That I was already constantly becoming someone to retain other peoples attention and approval. I talked the talk, said the right things, and earned what I thought was expected. I did what everyone else did, never stood out, and tried to enjoy all the things we accept to be good, fun and normal. Which was all fine I suppose.

But when I visited my Mistress, and she took away my name, took away my clothes and took away my free will - I never felt more real in my life, which is a scary, sad and exhilarating prospect all at the same time. But I guess that's why I only visit her, every three months.

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rdoolittlerdoolittleabout 8 years ago
Got my attention

Very well thought out with good dialog. Look forward to more.

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