Nisan 18, 2025

Mr. Mason’s Sissy Slut Ch. 01

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Destruction

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My first story! Please let me know what you think or if you want a part 2. All characters are 18+.

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“Yes daddy!” I moaned as my best friends dad pumped vigorously in and out of my ass. “Are you really gonna cum from having your shithole fucked you little slut?” he said as he pushed down with two fingers on my caged up clitty, slowly circling the tip of the extra small cage. I was so sensitive from being caged up, that it sent shivers of pleasure through my body. I felt a straining in my body, as if I was about to pee. Realizing I was about to have my first sissygasm, I thought back to how I let myself end up like this.

My boy name was Kyle Ritter. It all started the summer after high school. I was never as athletic as the other boys. Despite being 18, I was only 5′ 7″ and weighed in at 120 lbs. I naturally became shy and submissive, spending most of my days at my closest friend Cole Mason’s house, who was the starting quarterback for the football team. Experiencing a lot of locker room talk, he often made jokes about my feminine frame and how he would love to “stretch that little asshole open.” Although he made these jokes with other boys, they felt much more applicable to me due to my frame.

I had a tight round bubble butt from my days of lifting weights, although I gave up since my body had to work twice as hard to grow muscle anywhere else. I had resigned to maintaining a slim figure through the stair machine and some ab workouts. This had the achieved effect of keeping my body slim, yet I couldn’t help but notice how girly I looked in the mirror.

If I arched my back slightly, I looked like the fuckable desire of any man.

Not that I was the fuckable desire of any woman, however. My small penis also had some trouble growing, and barely approached 4 inches rock hard. Around 2 months ago when I found sissy hypno, I immediately became hooked and began gooning for hours. However, I was too scared to order toys to my house so I resigned to wearing my older sisters “lost” panties which fit me surprising me well. Eventually, it became an almost everyday thing. The panties fit my small package well and showed off my round ass which I had grown to love. Lucky for my sissy tendencies I was a grower, but after Cole had accidentally seen my penis on soft (thank god I chose not to wear panties that day), he never let me hear the end of it.

“With you it’s gonna be like throwing a hotdog down a hallway,” he half jokingly said one day, while we were on his living room, grinning that he had gotten a chance to humiliate me.

His father suddenly walked in, which was a rare sight. Mr. Mason was a executive sales rep for a large medical company, and was often traveling. Cole immediately stopped and changed the conversation to something more appropriate. I had noticed that while Cole was very brash around his mother, he never dared talked back to his dad.

“Cole, don’t you have an interview to go to?” he said sternly.

Cole had an interview with a small medical company that his father had lined up for him. Cole had told me there was no way he was going to work there, since it was over an hour drive away.

“Yeah I’m leaving right now.” he quickly replied, clearly annoyed his earlier plan to bum the interview had failed.

He grabbed his keys, said a quick goodbye, and then drove away.

“Guess I’ll be going then” I said as I got up.

“Sit down” Mr. Mason said sternly.

I meekly followed his instructions, as he smugly smiled. I started to get scared. Did he think me and his son were fucking or something?!

I mean, not that I hadn’t imagined it a few times, but I was into older men, in fact it was serious, “alpha” men like Mr. Mason that I wanted to fuck me silly.

“I hope my son wasn’t making fun of you earlier.” he said.

“We were just making jokes” I quickly said, not wanting to get Cole I trouble.

“Hotdog in a hallway…is your ass really that loose?” He asked as he chuckled.

Never having been penetrated before (other than my own fingers all lubed up with spit, of kağıthane escort course), I quickly got defensive.

“He was talking about my dick in a girls pussy…not his dick in my ass.” I quickly blurted out, not wanting his dad to think there was anything gay going on between me and Cole.

“That’s not exactly what I was implying but it’s interesting you came up with that. Is your dick really that small?” He asked, emphasizing the last two words.

“Bet it’s bigger than yours” I retorted back, not wanting him to think less of me.

Big mistake.

I could tell from his face that he didn’t like my answer at all. Unlike Cole, he didn’t take banter of this kind as jokes, he was from a different generation.

“Don’t talk back to me you little shit” He said as he got up from the sofa. He grabbed my frail wrist and dragged me upstairs. Not wanting my only friend’s dad to hate me, I quietly followed. He took me to the master bedroom, and locked the door.

He stared into my eyes as he unzipped his pants and dropped his underwear to his knees so I could fully examine his cock.

A potent, masculine scent filled the room, as I saw a real man’s cock for the first time.

Even while soft, he was double the length I managed to reach when erect. While I knew I would lose the “bet” between us, I didn’t expect Mr. Mason to be hiding a monster like this in his pants.

He could tell I was intimidated, and began to unbutton his shirt as well,. “Now let’s see yours, you did make a bet after all” he said. I froze and started to whimper out a response but before I could say a word he pinned me against the wall.

Although he was in sales, Mr. Mason may as well have been a construction worker. He kept his upper body well trimmed to show off his massive muscles, tattoos, and wide abs. But his lower body was rampant with hair to display his masculinity. His pubic area, while comparable to the Amazon Rainforest, somehow enhanced his cock size, meanwhile I stayed clean shaven in order to give boymode me an extra inch of confidence.

Noticing my fascination, he took a step even closer. My boy mode defensiveness started fading as I realized I was being turned on. He was so much more bigger and intimidating up close, his veiny cock was beginning to brush against my sweatpants, and the smell, oh god the smell of his cock was so –

“What’s this?”

He asked as he felt my small clitty slowly rise and barely prod his massive cock through my sweatpants. My little girldick began to rise more and more as it got a better feel of Mr. Mason’s penis, which swung like a engorged elephant trunk.

“Did simply seeing my cock really turn you on that much?” he asked.

“No sir I’m sorry, can I please go now?” I barely whimpered out.

He slapped me across the face.

“You are to call me daddy when we are alone from now on, not sir. Is that understood?”

My face stung with pain, yet my erection only grew stronger. Feeling this with his own cock, he understood what my true desires were. He slapped me again, on the other cheek this time.

“I won’t repeat myself” he said, awaiting my response.

“Yes daddy” I responded, not wanting to disappoint my best friends dad.

“Good girl.” He said, pulling me even more closer while he started groping my ass.

“You have a body better than most girls, do you know that? You were made for breeding” he said as he groped my body, ignoring my cock but focusing on my hips, ass, and began swiping his finger up and down my crack, barely poking in, as if it were a credit card swiper.

“I’m not a girl though.” I quickly responded back, feeling embarrassed my small cock and sissy frame being called out for the first time.

He was angry now. He turned me against the wall, and pulled my sweatpants and boxers to reveal a pair of my sisters very exposing panties. Fuck me, and I had just said I wasn’t a girl.

He didn’t let his surprise stop his punishment as he began spanking my ass hard, switching cheeks with every word and even syllable. He yanked my panties up to give me a wedgie, to kaman escort expose my ass even more.

“You…will…call…me…daddy…when…ever…we…are…alone…to…ge…ther!

If…daddy…says…you’re…a…girl…that’s…what…you…are!”

He spanked even harder now.

“UN…DER…STOOD?”

“Yes daddy” I yelped after he was done.

He pinned me against the wall by my throat with his left hand, and began snapping pictures on his phone with his right.

My decision to turn around and see what he was doing was a mistake, he grinned as he got my face, panties, and bright red ass pinned against the wall all in one image.

He pushed me so I was sitting on the bed and said “Now what was that about you not being a girl again?”

“I just like the way these panties feel daddy” I said, still sheepish about talking about my sissy-ness.

“Guess your parents won’t mind finding out about them then” he said as he began typing on his phone.

My boner died down as I realized that he had more than enough blackmail to get me kicked out of my conservative parents house and even ruin my relationship with Cole. I knew I had to submit to him.

“Sorry daddy, please don’t send that to my parents. I’ll be a good honest girl. I do watch a lot of sissy hypno but all I do is wear panties, I swear! And sometimes i suck on my fingers imagining it’s a cock. And then I shove those fingers up my ass.”

For the first time, I saw his massive cock slowly get hard. “You’re a natural born sissy slut. Lucky for you, daddy is very welcoming of femboys who accept their place as my property.”

Right before his cock was about to touch my nose he walked to his drawer and pulled out a “nub” style chastity cage. Obviously he had had some experience with sissies before as he made me stand up and masterfully put on the cage before I could get hard again.

“This is only to be referred to as daddy’s clitty now is that understood”

“Yes daddy” I responded, cheeks flushed red as I realized my fantasies were coming true

He chuckled as he said

“Usually I have to struggle for an hour to put that on one of my sluts” he chucked, slapping my balls “guess that size was made just for you”

Half naked, shirt not even hanging over my chastity cage, with my panties barely on made my clitty respond honestly to his humiliation. It strained against the cage and daddy felt my package start twitching as he cupped my balls.

Noticing my excitement, he dragged me by my balls and cage into the master bathroom and told me to shave from the eyebrows down until I looked like one of the sluts from the porn I loved watching so much.

As soon as i was finished, I put on the outfit he had picked out for me, a pink crop top that said “yes daddy!” the sluttiest pink thong I’d ever seen, a cute white mini skirt that barely covered the top half of my ass, and white thigh high socks with pink stripes. On my feet I was wearing a pair of white and pink athletic shoes that surprisingly put the whole outfit together. However it was the short pink bob cut wig that did it for me. Only having been in panties before, I felt my clit strain against its cage as I looked at myself in the mirror.

I looked more feminine and fuckable than any girl I had ever seen at school.

However, what really turned me on was seeing Mr. Mason after I exited the bathroom. He had taken all his clothes off and was puffing on a weed vaporizer.

He stood up to get a good look at me and for the first time, his cock quickly became fully erect. No longer scared, I took a(nother) second to admire Mr. Masons naked body. He was definitely well over 6 feet tall, and his massive muscles and hairy body really put into perspective how feminine I really was.

It was clear seeing my dressed up like the sissiest slut had had an effect on him. His massive cock now had more veins budging out from all over it and had grown to be around 9 inches, now fully erect.

While I was busy staring at his cock, he moved towards me and stuck the weed vaporizer in my mouth. After coughing kapaklı escort out a long hit, I felt my sissy urges come in like never before.

“This has a special aphrodisiac for men mixed in with the thc…i think on girls like you the effect is supposed to be twice as strong or something” he chuckled

Before I could respond he plugged one nose roughly with his large thumb and lifted a bottle of poppers to the other. Knowing what to do from hypno, I took a long good sniff. My head went crazy after that and I had to do everything in my power to not shove his cock in my mouth. He took advantage of my relaxed state and bent me over so he could shove his lubed up pinky, which felt bigger than my cock, into my ass

My ass started to get very hot then cold, then stayed suspiciously warm. “Now this is an anal aphrodisiac specially meant for sissies like you.” Instead of thinking about rubbing my clit as usual, I wanted my ass to be filled like never before. Fuck. Was he trying to drug me into loving anal sex? It didn’t matter. I needed cock now.

“Thank you daddy!” I groaned as the drugs began to take effect. I had felt horny while high off weed and watching sissy videos, but these drugs were something else. I felt my sissy desires reach a climax.

As I stared at Mr. Masons cock, my clit strained and mouth drooled. I almost came from excitement when he said “Go ahead bitch, suck daddy’s dick.” I started licking and replicating everything I had seen in the videos and practiced on bananas. The drugs were taking effect, and I fell in love with the smell, texture, and size of daddy’s cock even though I could barely go past the head. Daddy was much bigger than the bananas I had practiced on, and I went into overdrive trying to deepthroat him, while applying tounge swirls to the underside of his penis head.

“I can’t believe your’e a virgin, you suck cock better than most of these sluts” daddy said and I could tell the drugs were taking effect on him too.

He began to take control with his hand, masterfully edging my gag reflex and breath intervals so I was barely breathing and always pleasing.

His scent was too much for me to handle, as his long pubes started getting closer to my nose with every deepthroat, I felt the need for something to fuck my ass. As if on cue made me inhale another popper and started fucking my ass with his aphrodisiac lube.

My moans were drowned out by his cock, but I almost screamed when he quickly inserted a medium sized butt plug and smiled, seeing tha pain in my eyes. “We’re going to have to work up a lot bigger than that one if you’re going to take daddy’s cock Kylie.” he said. Hearing the feminine version of my name that I called myself online while being Daddy’s sissy slut was so exciting. He smiled as he showed me how much bigger the following plugs were going to be.

Finally caged and plugged like I always wanted, I decided to thank my daddy by servicing his cock like there was no tomorrow. After around 10 more minutes, his cock throbbed and convulsed ropes of cum into my mouth.

With how the drugs were messing with my brain, it may as well have been an ice cold Coca Cola going down my throat. I swallowed as much cum as I could, and after I pulled off his cock, daddy smeared my face with the rest, painting my face with at least another 4 ropes of cum.

He sighed and said “Good girl. Today was just a trail phase for me and lucky for you I’m in town the whole summer. You are ordered to come back tomorrow for some real anal training.”

“Yes daddy” I responded.

He put my number in his phone, helped me clean up, but ensured I went home in the same outfit, save for anything noticeable like the shoes or wig. I simply wore my boy clothes on top and went home.

Caged and plugged, in panties and stockings I said a quick goodnight to my parents and went upstairs so I could take my boy clothes off. While the drugs were wearing off, my horniness wasn’t.

I locked my door and hopped in bed but in chastity the most I could do was rub my smoothly shaven legs in their white thigh high leggings and wiggle my butt plug around.

As it sank in that I was now going to be Mr. Masons personal sissy slut, a new feeling of submissiveness sank in. I had a master now who was going to train my mouth and ass. My boipussy twitched against its plug as I dreamed of daddy’s cock, and how I would get to service it again tomorrow.

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