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High School Dilemma Parts 3 4 5

June 8, 2011

The stories posted here have all reached certain standards of readability and content. I focus on collecting stories that involve humiliation of a young, feminine submissive by a dominant male. As a rule, all the stories posted here are X rated, but they involve more than straightforward non-consensual sex. Instead, these stories will pay attention to the emotional and psychological humiliation of the submissive. More often than not, there is a training or feminization scenario through which the sub learns to submit to and please "real men".

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A collection of sissy humiliation stories I've read and liked, with strong emphasis on dominant males and submissive boys or sissies.
Once in His office, I strip and approach Him humbly. He is sitting at his desk, fully clothed again in a suit. He barely looks toward my direction, before He rolls back his desk chair, opening up my entrance Home. I crawl underneath. Since the last time I was here, He had installed a stainless steel D-ring on the back panel under the desk, the curve of the ring was heavy-duty thick and glistened even in the darkness. Attached to the ring is a leash about four-feet-long and punctuated by a thin leather collar.
My body freezes when I see the leash hanging under the desk as I contemplate what is going on. It’s obvious, but I need the pause because my body is trying to tell me to run. I can leave. I can be dressed in a few seconds and still make it to school on time. But my dick is rock hard. My heart is pounding against my breast plate.
“Welcome Home,” he says, cheerfully.
I put the collar around my neck. It’s thick, dark leather and cold against my skin. He reaches over and fastens the buckle. The collar is secure but he keeps fiddling with the mechanism until I hear an unmistakable click. I reach up to finger the small padlock that is threaded through a latch in the collar. I am locked here.
A tear runs down Jade’s cheek when she realizes it is time for her to start slurping the excess gunk up.
Her stomach protests as she leans in and licks the slop off the cock. She makes sure she also gets the excess that is spider webbing between her fingers.
There isn’t much taste to it but this fact doesn’t make it any less disgusting to her. She knows she is supposed to smile and look joyful about performing the act. However, her mind is focused too much on trying not to be sick.
“Good girl,” Simon says with a smile.
Simon loves sissies that hate dick. It boggles his mind that anyone would want them any other way.
“Action.” We all sat in silence. I knew what I was supposed to do. I couldn’t believe where I was. This morning, I had woken up a virile young straight male who was almost going blind he was so crazed for pussy. Now I was the pussy, being lowered onto a massive cock, still wearing a miniskirt which was now pushed up against my waist, exposing my naked cock and legs below, and most importantly my ass.
What the hell, my face streaked with tears I looked at the camera and read the cue card “My name is Roy and I’m a pussy bitch who needs to be taught how to please a man.” I turned bright red as I said it. I didn’t want to say the next part. I swallowed and said it, “Make me cry daddy. Turn me into the cockslut I am.” I had sealed my fate, feeling as the man below me softly lowered me down over his big fat dick, dripping in precum.
Janice swallows hard and then kneels down in front of her teacher. She makes sure she doesn’t bend over too far. The last thing she wants is for the back of her skirt to raise up too high. She has white cotton panties on under her short tartan skirt, so they would probably only notice her plug. That would still be horrifying.
Her hands tremble as she reaches up and pulls her teacher’s cock out.
I know that you may think me something of a bully, but who cares? Forcing a lad to dress like a girl, act like a girl and serve my cock like a girl against his, or should I say her will, is the most powerful aphrodisiac for me! And looking down at her with her legs open in her pretty little panties; trembling with fear, the wide eyed scared look on her face was making my cock bulge.
The tears in my eye were overshadowed by the sound of a vehicle, the first in a month. I was hoping it was someone coming to rescue me. But I knew it was just the opposite. I was afraid, nervous, apprehensive, and submissive about what would be next.
“Here come the men. Go open the door. ” he said.
I walked obediently towards the door and although the plug wasn’t that big I could feel it every step. Between the walking lessons of short steps foot in front of foot and the plug I could feel myself swaying to the door. I heard car doors open and some muffled male voices. Apprehensively I turned the old rusty knob and the door creaked open.
Now she was completely hairless except for the hair on her head.
“Turn around facing me and kneel down, bitch.” Zeke ordered.
“Now you look like the sissy you are.” Zeke sneered. “What are you, bitch?” Zeke demanded.
“Yes, you little whore. You belong to Daddy and Daddy’s going to mark you as his property.” Zeke said. And grabbing his now flaccid cock, he aimed it at Chrissie’s chest and began to piss on her.
‘How will you act when I’m here boy?’
‘Like a faggot Sir,’ trying hard to sound as faggy as I can.
‘I will still act like I’m a fag Sir.’
‘Good boy.’ You let me loose. ‘Go get me a drink faggot.’
I prance out of the room trying to walk like a fag. My ass still feels on fire.
I come back with your drink. Head down, I extend my hands. ‘For you Sir.’
He takes the drink from me. His finger lifts my chin making me look at him, his stare intense, penetrating. ‘Why are you still standing faggot?’
I move to my knees quickly. ‘I’m sorry Sir.’ Head down, knees spread.
Thirdly, we have full control and access over you and everything you
own. Your house, your clothes, your car, everything. Is that clear? Are you
keeping up you sissy faggot? Go on tell me that the sissy faggot
understands and agrees to comply with everything I’ve said so far”
Tears were welling up in the corner of my eyes as the bleak future promised
by his, no by my new orders, was so clearly painted. I resolved not to let
them see me cry, it would serve me on purpose, and would only serve to
emphasis their hold and superiority over me at this time. I followed the
only course open to me. “Yes… yes, I agree.”
“Not good enough cunt. I told you to tell me the sissy faggot understands
and complies with everything Master Sam has said. . In fact beg me! Go on,
beg me to let the sissy faggot do everything Master Sam and Master Jim
want, beg me to use and abuse you and all your stuff. Go on cunt, beg me”
I laughed at him. “Does my little cocksucking girlie boy want daddy’s dick in her mouth?” I teased him.
He squeezed his eyes tightly closed and shuddered, but then whispered, “Please, daddy, I… I wanna suck it. I wanna… I wanna suck your big cock, please.”
I reached out and pinched his earlobe with my fingernails. “You know what that makes you, Punk?” I asked him, my voice gentle.
Punk groaned but said, a mixture of misery and lust in his whimpering voice, “A little faggot… I’m a little cocksucking faggot… I like to suck dicks, daddy… plah… please…”
“You’re gonna want to stay real still, girl, or this is going to be painful.” I advised, showing him the razor. He whimpered but lay back and allowed me to get on with my work. God, I love shaving these boys, turning them into the little cock-hungry sissies I know they are. When finished, he only had a thin strip of hair running vertical right above his crotch—just like a real girl!
“Turn over.” My voice was already a bit husky, anticipating what was coming. He struggled a bit to turn over with his cuffed hands but managed without my help. My cock started leaking precum when I got that first look of his beautiful ass. It was high and tight, not too big, just how I like ’em. Spreading those pale cheeks, his pink cunt was winking at me shyly, and he had absolutely no hair in his crack. I bit each of his cheeks and gave a sharp slap; he jumped.
“Does your little roommate know what a little slut you are? Because if you don’t send me a text of you sucking his dick by the end of the month I think we’ll have a little party the following weekend” and with that he thrusts up carrying me up off the floor and and into the wall. pushing me up against the wall while he hammers into me. He grabs me around the throat, choking me, and asks right into my ear in-between breaths “whose slut are you? You’re my little fuck meat and anyone I hear of you with outside of your work becomes the same, and then you work from home. Now say it!”
“Yes, daddy I’m your little fuck puppet, please fill me with your love juice.” I croak out. It hurts, but what all makes it worse is that is when I cum.
“Pick your bowl up and kneel in front of me,” he commands.
“Higher,” he corrects me. “Put your chin right against the side of the bowl with your lips just above the top.”
The tears are streaking down my cheeks as I obey.
“Good girl,” he praises. “Now open your mouth real wide and stick out your tongue.”
I want to protest. He gave me a choice and I clearly choose the food bowl and not my mouth for his deposit. I resist for a second then open my mouth. I feel like such a pussy. Just a few seconds ago I told myself I would never let him cum into my mouth. Yet here I am like a baby bird waiting for its supper.
“Oh, daddy’s going to give you plenty of protein,” Dean Miller says as he jacks harder on his dick. “Oh! Here it comes!”
I look on in shock as a huge blast of white cum fires out of the end of his dick and hits the dog food just inches from my face. Some of it splashes off the food and sprinkles my tongue and lips but not much. He fires 4 more equally impressive blasts that do the same. By the time he is done the dog food is absolutely soaked. Amazingly, less than a half teaspoon seems to have gotten into my mouth.
“Good girl,” he praises again. “You can finish your breakfast now. Don’t stop until that bowl is spotless.”
“Maybe if you are good, Master will let you suck his cock someday sweetie,” she tells me. She throws me a kiss and leaves the room.
The dom stands there looking at me. Even after coming, his cock looks big, hanging there above those big balls. He sees me looking at it.
“Well Stevie, having fun?” he asks as his hand reaches down and strokes his cock.
A drop of cum comes out and he wipes it off with a finger and moves over to me and bring his finger to my mouth. I just stare at his finger as he brings it to my lips and rubs cum all over my lips.
“You will learn to crave cum boy, not be able to get it out of your mind,” he states coldly. “I don’t know Sir, this is different than what I expected, I don’t know if I can do this,” I tell him, confused and unsure of what is happening.
As he thought about this, Dan raised his left hand up to his son’s head and started pushing it downward. Danny knew what his father wanted and didn’t put up a struggle. He did groan in despair though. He had sucked his dad’s dick earlier in the day without groaning, but that instance had been a spare of the moment thing.
However, Danny knew this blowjob was coming over 2 hours ago when they were at the clothing store and he found out what they were buying. God, Danny was embarrassed while they bought the clothes. His father told the sales lady that the clothes were not for his son but for a twin sister who was the same size. That they were just using Danny as a model since they were the same size and wanted the items to be a surprise for his sister.
Her latest boyfriend looked on in amusement. He couldn’t have been more than sixteen; young and muscular, just like all the others. So many of the others. The only real difference was this one was blond; Stephanie’s dates tended to be Black or Hispanic of late. He was naked, cum glistening on his still-turgid cock. Nine or ten inches, I quickly estimated. I doubted I’d be able to take it all in my mouth. I hadn’t yet learned to deep throat, even after six months of humiliation at the hands of my stepdaughter and her suitors. He was probably inexperienced, too, so might cum quickly if I had to suck him off.
“Is your slut any good?” he asked, taking a moment to flick his finger against the cage surrounding my cock, causing me to flinch. “Very cute, by the way,” he laughed. “I think the look suits her.” Except for my head, I was completely, permanently hairless. She said it would make the tattoos she had planned easier; so far, there was just one – the word “sissy whore” in lower case letters on my left ass cheek. Heavy mascara and bright red lipstick only made me look more hideous, I felt, but even that wasn’t as bad as the professionally done finger and toe nails. Bright, florescent pink, with a single letter on each digit spelling out “panty slave.” I could hide the tattoo with clothing; I could remove the makeup; but if I ever I went out in public – that hadn’t happened yet, but would soon – everyone would be able to see my fingernails.
“No, I mean, I don’t believe you’re not a girl, just cuz you’ve got one of those. You came in here and your name was Candy, and you seemed quite like a girl, I’d say. Do boys usually dress like that, talk like that, and wag their little behinds around like that?”
“But you did those things, exactly. So you’re a girl.”
I couldn’t believe what I was hearing. Could he possibly be that dumb? For a second, I wondered if that be the case, and then I noticed that my bulge was, well, a bulge. Had I got myself up with Candy’s ass?
“Besides,” he said, and in one motion, undid his belt and dropped his pants, and a second later the guest did too, “these are cocks. That’s just a little toy.”
“Daddy?” one of the dumbasses asked, “He’s not your dad, Klint. What the fuck’s going on here?”
I turned to the boy and said, “Your boy here is really my girl.”
“Daddy please don’t…” pleaded Gaby, as she came over towards me.
When she got close enough, I slapped her hard on the ass and gave her the bag. “Go put these on. Now.” I commanded. “Show these boys what a pussy you really are.”
“You see, Don, you are not going to be a male anymore. As of this moment, in fact, you are not to consider yourself a man. I certainly don’t regard you as one. No, to me you seem like a perfectly sweet and innocent, if a bit naïve and silly, teenage girl. Sure, your hair isn’t long, your voice is too deep for my liking, and your breasts haven’t developed yet. But we’ll get there, and within a few months you’ll be my feminine slavegirl, and with a little luck maybe even my girlfriend. I’m getting ahead of myself, though. What’s your gender, slave?”
Don’s mouth was still agape, and his eyes were becoming wider by the second. He closed his hands in hopes that Dave wouldn’t see them shaking.
“Slave, I asked you a question. What. Is. Your. Gender.”
“Uhhh….”
“’Uhhh’ is not an acceptable response, slave. Do not make me ask again.”
“Ummm… female. Master.”
“’This slave’s gender is female, Master,” Dave coaxed.
“This slave’s gender is female, Master.” Don gripped the armrest in a mixture of fear and anger.
Parts 1 and 2 here: High School Dilemma
“Well Sissy you are definitely a girl. Girls often have accidents so get use to it. It’s something to do with the length of your urethra to your bladder. Don’t you wish you had a penis?” Sean taunted me.
“Yes Sir I wish I had a penis,” I answered.
That’s when Sean began telling Uncle and Tiny how I really didn’t have a penis but instead a slightly enlarged clit.
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