Uncovering the Sissy Beneath

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My journey of being held captive and turned into a sissy.
2.9k words
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Part 1 of the 7 part series

Updated 06/09/2023
Created 06/06/2019
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Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional.

*

During my childhood, things were rough. I wanted to be cool, but the other boys in my neighborhood and school would pick on me. I was always getting beat up, and everyone would call me gay. When I got older I did everything in my power to avoid these situations. I was much bigger and looked as though I could handle myself in a fight, even though I couldn't. I Grew a beard and did everything possible to prove I was alpha and not to be messed with. It worked for the most part and I was rarely bullied anymore. However, I would run my mouth off to anyone who would try to put me down, but one day it went too far, and my life would change forever as a result.

I was in my early 20's and working as a pizza delivery driver. One day I was out delivering to a customer in an extremely wealthy neighborhood. I pulled up to the customers house, a beautiful mansion with a gated entrance. Pine trees lining the entire property. It was very private and you could barely tell there was even a house there. I pressed the button for the intercom and the gate opened a few seconds later. I pulled my car up the driveway, parked, and brought the pizza to the front door. I knocked and a few seconds later, a tall older man with a deep voice answered the door. He told me he needed to go grab the cash from his wallet and to come in to the kitchen and wait. In most situations I would wait outside, but I wanted a good look at this enormous house.

I followed him into the kitchen, and he tells me to just wait there. After a few minutes he comes back with the cash. He hands me the money and asks for his change. Unfortunately, I didn't have enough to give him back. He gives me a mean look, and says, "well, go back to the store and get it."

I start to get mad as obviously he was not planning on tipping me, but also wants me to go all the way back for a couple dollars. I explain to him that maybe if he tipped me there would be no need, but he insists that I do not deserve one as it was irresponsible for me to leave the store without enough change. I start to loose my temper, and the next thing I know we are in a full on argument. He starts going on about how I lack discipline and need to learn some respect. I tell him to fuck off and begin walking back out the door.

A couple seconds later I feel him grab my shoulder and spin me around. He swings his hand back and slaps me right across the face. I try to hit him back, but he grabs my arm and throws me strait to the ground. I try to stand back up but he yells at me to stay down. I cower as I can tell this is not a fight I can win. He draws his hand back again and I curl up into a ball with my hands over my face to block him. He keeps his hand up as I plead for him not to hit me again. He brings his hand down and grabs me by the chin. screaming at me to look him in the eyes. Whimpering, I look him in the eyes, begging for him not to hurt me.

He then proceeds to lecture me on my attitude. Saying that a sissy little girl like me should never talk that way. confused, I respond, "Dude, I don't even look like a girl, and aren't you a little old to be bullying someone."

"Let me guess," he says. "You've been called these names before haven't you? Did you ever think that maybe they were right? Maybe they weren't bullying you, and just trying to help you accept what you are?"

I try to stop him from continuing. Saying "I'm sorry I cursed at you, but I really need to be getting back to the store now. I won't call the police, just please let me go."

He says, "Okay, but first, you have to admit to me, AND yourself, that you're a naughty little girl that lacks proper discipline."

"This guy is fucking crazy," I think to myself, but I comply and tell him "fine, If that's what I have to say for you to let me leave... I'm a naughty little girl that lacks discipline. May I go now please?"

He responds "While that's a great start, "I don't believe you're being sincere to me, or yourself."

I take a deep breath. "Alright, I'm not sure what I'm supposed to say here then..."

He replies, "your words are a great start, but words alone aren't nearly enough to prove to me you truly believe in what you are saying. If you are ever going to truly admit to yourself that you are what you now say you are. You will need to show it with your actions."

"No way" I say as I try to back away again.I start to get nervous, as I hesitantly ask,

"What can I do to show it with my actions then?"

He shakes his head in an annoyed manor, "You say you're a naughty girl, and that part I already know, but it's going to take time for you to understand this. However, you clearly lack discipline, but don't worry, I can help you with that."

The situation was getting creepier by the minute, but as he was talking I was trying to figure out if there was a way I escape. I knew I wouldn't stand a chance in a fight, but I was one hell of a runner.

He proceeds to ask me, When the last time you had a good spanking?"

That was it, I jumped up and made a run for it. I started running down the hallway towards the front door. To my surprise, the front door was a double lock system that required a key to unlock it. I scramble for another way out. I found another door out the back, but that too was a double lock. I realized, I was completely locked in, and he didn't follow me or anything. It's obvious this was a set up from the start.

"Let me out, please!" I shout as I continue to panic. He starts walking towards me. Scared, I dropped back to the ground and curl up again.

In a stern tone he says to me, "I asked you a question young lady. When was the last time you got a good spanking?"

"I don't remember," I cry out. My dad never hit me and my mom only spanked me a few times when I was younger, but that's all I can recall."

"Well that explains a lot, doesn't it. If you can't remember, then you definitely never got a proper whooping. See, if your dad had just taken a little time to set you right maybe then you wouldn't be in this situation. Real men, like myself, got whipped into shape fast, and it builds strength. When little brats like you don't get the discipline they need they end up getting into trouble. Trying to prove they are masculine and strong, but it doesn't work that way. So here is what's going to happen. You're gonna get that whooping you need, and depending on how you take it. Maybe I'll reconsider your release."

"yes, yes indeed" he says with a evil grin as he keeps getting closer. "I'll tell you what, you take it like a man, I'll admit I was wrong about you, and I'll let you go on back to work, but if you keep crying like a spoiled little cunt. We're gonna keep working to get you out of this denial. How does that sound?"

I saw no other option, and agreed to his terms. I needed to get out of there as fast as possible anyway so that I didn't lose my job.

He tells me to stand up and follow him. He then forcefully yanks me by the arm to keep up. He leads me up the stairs and into what I assume is the master bedroom. His bedroom is gigantic but we walk strait past and into his very spacious walk in closet. He has very many tailored suits, and then I realize what he's going for. A large collection of belts.

"I usually keep one of these on my waist at all times, but this at least adds a little fun as you get to choose which belt I use to strip that attitude right off your backside."

At this point I was shaking uncontrollably. So much was going through my head all at once and I could barely even concentrate enough to pick. I touch a few of them looking for the lightest material in hopes that it'll hurt the least.

He chuckles at me, "You're looking for one that won't hurt as much aren't you? I wouldn't put too much thought into it. No matter which one you pick, I'll still make sure it gets the job done right. So hurry on up now and stop stalling. You don't want me to be anymore angry than I already am."

I grab a random belt and cross my fingers. He tells me to take a good look at it, and then hand it over to him. I glance down as I can see that the one I grabbed was pretty thick. I hand it to him, hands shaking so hard I nearly dropped it. He grabs the belt and with his other hand, drags me by the arm back into the bedroom and situates me facing right into a corner. He let's go of my arm and begins instructing me. "Now, I want you to stay facing the corner, and slowly take off your clothes until you are down to your underwear. I want you to fold each article of clothing neatly and hand them over to me."

I begin to remove my shirt, followed by my pants. I do as told and fold each article carefully handing them over to him. I remain facing the corner, standing in nothing but my underwear, awaiting further instructions.

He tells me to turn around and walk over to him. He is sitting down on the edge of his bed with the belt lying to his side. As I begin to walk towards him he points to his lap, signaling for me to bend over his knee. I think to myself "here goes nothing," and drop my body right over his lap.

He holds me down firm in his lap and maneuvers my ass into position. I couldn't believe that I, a grown adult, was allowing some middle aged strange man throw me over his lap for a spanking.

"Now," he says, "You say you're a man? I say you're a sadly mistaken little sissy who's been living a lie. Well let's just find out who's right and wrong." However, I want to make sure you understand why you need this. You Irresponsibly show up at my door, late, and without change. Then, when I decide you don't deserve a tip, which is entirely my decision by the way. You have the nerve to start arguing with me, in my house. You may think you're an adult because you're over 18 now, but let me tell you something. You show some damn respect to your elders. Just because you're legally an adult now does not give you any entitlement. You have the attitude of a teenage brat that never got what was coming to them. Well we're gonna fix all of that right this instant!"

"Smack!" His hand comes down hard over my ass. I flinch but he keeps me from moving with his other arm. Without pause he spanks me bare handed cheek to cheek. I start to shout "stop," but he keeps on going, and I can feel my ass start to heat up.

"Oh does it hurt?" he interjects. "Well guess what, we're only getting started here, I haven't even gotten to the belt yet."

After about five minutes, he lifts me up right off his lap and throws me face first onto the bed. He's so strong my body could barely stop him. He grabs me by the hips and pulls my ass into the air. "Now stay on your arms and knees with your ass up!"

There's a pause as I make sure to position myself as told. He grabs the belt from the bed, folds it in two and cracks it a few times. The sound scares the life out of me, and all of the sudden I can remember the fear I had when I was child, and my mother would do that. I thought those days were long gone...

Out of nowhere I feel the first blow of the belt. My body jumps forward and I lay flat as the sting is unbearable. He pauses, "ass up I said!" I reposition myself and he strikes a second blow. I can't help it. My body jolts forward yet again, but this time he doesn't pause. Blow after blow he starts wailing the belt down on my ass. I start to scream, but it does me no good. I try flailing my body to the side back and forth, but he anticipates my move every time. As much as I'm trying to be a man about it, I simply just can't take it, nor do i understand how anyone could. He begins shouting, "I said ass up you little shit," and pauses as I try to reposition myself, but my legs are shaking so hard I can't keep myself up. The next thing I know he starts to yank down my underwear.

"No, no, no, no, please no," I cry out.

"What, did you think we were done here? Not even close."

Then I feel the belt come down right on my bare ass. I had never felt that level of pain in my entire life. It stung so bad, I jumped right off the bed. "Back down he screams!" I can't though, I try to run out the bedroom door, but he catches up to me, and as I'm running I feel the belt hit my ass again. I trip and hit the floor. I lay on the ground curled up, but I'm naked and I don't want to be hit anywhere else so I leave my ass exposed.

He continues dropping the belt onto my ass as hard as he can.

Within seconds I realize my attempt to prove I was a man to him has failed, and as I beg for mercy my eyes begin to tear. "Please stop! Please, I can't take anymore," but he just keeps on going. My tears begin to flow out fast, covering my entire face.

After a good 10 minutes of beating my bare ass mercilessly he pauses and picks me up off the ground and stands me up facing him directly in the eyes. He talks for the first time in minutes. "I told you that you were no man, You can't even hold still for one second. You're just laying on the floor pouting like a little baby." We're still not done here, but I want to here you say it again. Admit to me what you really are! Go on, say it!"

I try to speak, but I'm crying so heavily I can barely get my words to form. I try to catch my breath, and in a choppy sentence I reply. "I'm a girl!"

"Ah, so you admit your a girl then. What kind of girl are you?"

"I'm a naughty little brat."

"And you're learning a very important lesson aren't you?"

"Yes," I respond.

"Yes what?" He asks

Uncertain of his question I reply, "Yes sir?"

"Well that's a start, but I think now it's probably proper that you call me Daddy, don't you think? I mean, I am helping to give you what a real daddy should have given you right?"

Confused and feeling weirded out, I questionably say, "I guess so?"

"you guess so?" And he turns me back around throwing me forward onto the bed again. This time I land with my upper body on the bed, and my legs on the ground below. The belt starts to come back down with fury once again.

I begin to cry out at the top of my lungs, "I'm sorry, I mean yes Daddy!"

He continues with each stroke, "that's right, I'm your daddy now, and you are going to do as I say from now on, do I make myself clear young lady?"

"Yes, yes Daddy!"

"Thwack," and then he pauses, "what was that?"

"Yes Daddy!"

"Thwack."

"Again!"

"Yes Daddy, whatever you say."

It went on for what felt like eternity. It was probably around an hour or so, but it most certainly felt longer. I thought for sure by now, my boss was pissed, but honestly my employment had fallen to the least of my concerns. The only thing I could concentrate on now was doing exactly what this man, or 'Daddy,' tells me so I can get out of this situation.

To be Continued...

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5 Comments
AnonymousAnonymousover 4 years ago
Yes Daddy! Spank, me!!!.

Harder feasted ooooooooo oooooo owwweeeee ouchie harder

harder harder harderoooooooo owweeeeeeee!

AnonymousAnonymousover 4 years ago
spelling

Not a bad story but you need to get it roofread to correct the spelling and grammatical errors.

AnonymousAnonymousalmost 5 years ago
very hot

I wish I was you

Vineelasissy143Vineelasissy143almost 5 years ago
AWweesommeee...

continue the story

formyqueenspleasureformyqueenspleasurealmost 5 years ago
an interesting beginning

I do look forward to your next instalment, and how (s)he will conform.

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