Little Sissy Prick free porn video

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I know what they say about it not being your fault; that you are the victim and are in no way responsible when someone forces you to have sex. Still, I cannot help but feel somewhat to blame. I, after all, did stupidly put myself in a bad place and even if circumstances did play a part in what happened, I would still be a virgin if only I had not taunted him so.

My brother, Howie, and I had a typical roller coaster, sibling rivalry relationship. We had the usual childhood fights and were always bugging one another. On one day in particular the advantage fell my way and from then on I did everything I could to exploit it. You see, I walked in on my brother in the bathroom.

The door was shut and locked but he had somehow not pushed the door all the way into the jamb so that the latch had not engaged. I was in a hurry to use the facilities and he was taking the usual "forever" in the morning. I was yelling at him, through the door, to hurry up and he just told me to, "Go away, you stupid bitch."

I grabbed the door knob and raised my fist to bang on the door. The knob didn't turn but I felt the door move a teensy bit. Immediately I knew what had happened and pushing hard I burst into the room. The total look of surprise on his face was fantastic as was the immediate crimson blush of embarrassment that followed.

The little dweeb was standing in front of the mirror, a girlie magazine open on the counter and a pair of my used panties from the hamper held to his nose. His pants were about his ankles, his hard-on tightly gripped in his fist and his hand was jacking it at rabbit speed. He gasped, while turning slightly toward me in his surprise and at the same instant blasted off his gooey, white stuff all over the floor and counter.

He tried to back up and turn, but with his legs encumbered by his jeans, only succeeded in falling backwards. He reached back and was able to break his fall, but ended up on his butt with his stiff prick jutting up from his hairy patch, pumping his cum all over his legs, chest and balls.

I, as his older sister, did the only thing that I could; I broke up howling in laughter while pointing at the him in his predicament. The funniest thing, to me, about the whole situation was the size of his unit. It was incredibly skinny and not particularly long, reaching four and a half inches at most.

"What's that?" I demanded, pointing at his deflating penis. "Whoo-hoo-hoo-hoo," I laughed at him as I continued, taking advantage of his discomfort, "I caught you beating off!"

He squirmed, trying to cover up while at the same time attempting to pull up his pants. The job wasn't made any easier by the sticky goop all over his legs. "How did you ever get that puny little thing to work?" I went on. "It looks like a sissy's prick; a little sissy prick!"

The look on his face told me that I had really hit a nerve. I knew I could exploit it to great advantage. He eventually got his pants up and pushed past me to run and hide in his room. I, in the mean time, was doubled over nursing a side ache from laughing so hard at my brother and trying not to pee my pants.

It was Saturday morning and Howie was taking a shower. Our parents were gone for the day and there were just the two of us in the house. Once again I was in the mood for some sadistic teasing. I waited in Howie's room for him to come out of the shower. I was just wearing a terry cloth bathrobe and planned on embarrassing Howie. He entered the room, as I expected, wearing only a towel. I was hiding behind the door and snatched it off of him as he went by, leaving him totally nude. "Hey." he yelled as he immediately tried to cover up.

"What'cha trying to hide there, little brother?" I asked. "Whatever it is you sure aren't having much trouble covering it up It must be pretty puny." I continued.

"Leave me alone!" he shouted.

"Aww, come on; I just want to see what ya got," I said. "Tell you what. You let me see and I'll let you see," I dared. To show that I meant business I peeled aside the top of my robe and exposed my right breast. "What d'ya say?" I asked.

His eyes went round as he stared at my erect nipple. I've got a thirty five inch bust line, and very cone shaped breasts that stick up and out slightly to the side. My nipples are several shades darker than the creamy colored skin of my perky chest. I am five foot eight and really watch my weight with diet and a lot of exercise.

Our whole family is a bit neurotic in that way and we are all in top shape. I could tell that the little bit of flesh that I had exposed to Howie was definitely having an effect on him and that the promise of seeing more would make him putty in my hands. I figured a little flash on my part was worth the embarrassment I planned on dishing out in just a few moments.

"Well, wha'd'ya say? Want to see more?" I asked again as I teased him by slightly pulling aside the top of my robe starting to expose my left tit to my brother's saucer like eyes.

His mouth fell open as his hands fell away exposing his childlike phallus to my eyes. It appeared to semi-erect although it was a bit hard to tell, it was so small. I kind of felt sorry for him but not enough to not continue with my plan.

"Fair is fair." I said as I peeled open the top of my robe exposing both of my pointy tits to his eyes. His eyes flicked back and forth between my two cones as he took a couple swallows. "Oh, but I'm still not being fair am I?" I continued. "You are showing all your stuff and I haven't shown you mine."

I smiled at the dumb look on his face as I slowly peeled open the rest of my robe and let it drop to the floor about my feet. I now stood not five feet from my brother totally exposed. His mouth opened even more as he started breathing heavily through it. His penis quickly rose to it's full miniscule length as Howie stared at my chestnut brown hairy triangle.

"Here," I said, as I lowered my right hand and dipped the middle finger into my slit gathering some of my moisture onto the digit. "I know how you like my scent," I said as I walked over to where he was standing. "So let me add a little smell to what you're seeing." I continued as I wiped off my juices, in one quick movement, on to his upper lip.

His nostrils immediately started to flair as beads of sweat appeared on his brow. "Oh. I'm still not being fair." I said as he continued to soak up my nakedness with his eyes and sniff my musk into his nose. "I can see it all hanging out but you can't 'cause mine is all covered up. Tell you what..." I said as I turned and walked to his bed. Spreading my feet, I bent over at the waist and rested my hands on the bed covers. "That better?" I asked as I looked over my shoulder at Howie's dumbfounded expression.

I could see myself in the mirror that hung on the back of his bedroom door. My pussy was totally exposed to him now. My pink hole was slightly gaping open and to my surprise it glistened wetly and a bit of my slickness dripped out to the opening. My darker inner labia were pulled apart by my wide leg stance. Being quite long, they hung like velvety curtains on either side of my virgin hole. It was all framed by two hairy and very puffed up outer labial lips.

Looking at myself made me realize that my brother was not the only one excited by the situation. A weird squeaking sound came out of my brother's gaping mouth. His pecker now started to bob up and down, sort of like a little heart beating and a bead of moisture glistened at it's tip.

I turned my head, facing forward and tried my best to contain myself but it was too much and I broke out in a loud guffaw. Glancing over my shoulder at my brother I saw the look of confusion on his face. Not being able to hold back any more I sprung my trap.

I now let loose with a howling laugh as I said, while looking over my shoulder, "Is that ALL you've got? What a puny little pecker ya got there bro. Why, I've seen bigger meat on the babies I sat for! How do you ever expect to satisfy a woman with a sissy little prick like that?!... Though, maybe it's just my fault. Here, let me try to give you a better show." I went on in laughter as I started to rotate my hips first in a little clockwise circle and then a swing to the left followed by a little counterclockwise circle and swing to the right.

I watched the repeated movement in the mirror and could see my lips opening and sliding in a very seductive way. I was now starting to drool moisture out of my hole and down toward my clit.

The look on Howie's face was to die for. He looked confused, dumbfounded and embarrassed all at the same time. I knew that I had gotten him good this time and tears of laughter started to stream down my face as I now buried my head on his bed. My body was shaking with laughter at the look I had seen on Howie's face as I continued to repeat between laughter "What a little sissy prick!"

I was having a grand old time at my brother's expense when I heard a growl-like sound come from behind me. Suddenly I felt myself being shoved forward by two hands on my ass cheeks. I landed face down on Howie's bed with my waist on the edge and my legs spread and over the side.

In what seemed like no time my legs were kicked out farther to the sides and Howie was on my back. He pushed at my elbows and before I knew it my hands were over my head and both wrists were in the powerful grip of Howie's left hand. My brother is on the wrestling team and I've seen him make a similar lightning quick move before, only joking with his friends. I felt him reach down between us with his right hand as he said into my ear, "Hey sissy, how about a little prick." With that I felt the head of his penis being drug through my labia and positioned at the entrance to my hole.

"Howie, NO!" I screamed as I felt his hips lunge forward and my hole stretched. He had the head of his penis just barely pushing into my vagina. He hadn't yet really entered me, and still my virgin hole felt stretched to the point of tearing. I felt a burning pain in the delicate tissues at it's entrance.

For all the shit I was giving him about being so small he sure felt HUGE at the entrance to my most cherished place. 'How can this be hurting so much?' I thought to myself. 'I must be incredibly small down there myself to be feeling so much discomfort.' All this passed through my mind in but the moment that Howie held his breath following his initial assault at my center. I felt his hot breath on my right ear as he let out a ragged sigh.

"Howie..." I gasped as he held himself pressed into my divot. "Howie, please..." I begged as he panted into my ear. "don't..." I continued as I realized my labia had been pulled and stretched in somewhat with the initial slight intrusion of his penile head. "You mustn't..." I went on, "it's incest."

He continued to grip my wrists over my head and to keep his dick head just splitting my entrance. After listening to a few more ragged breaths in my ear I said "Howie it hurts... you're too big."

"What... this?" he croaked into my ear as he emphasized his words by nudging his hips forward once again.

"AAH..." I cried out as the movement caused the head of his prick to pop through the stretched ring of burning tissue. I felt the taught band snap tight around the bulbous head of his dick holding it firmly in place. He now had the head of his penis in my vagina. I gritted my teeth at the pain it's presence was causing. "Oh, it hurts." I cried through clenched jaw. "Please take it out, take it out!" I pleaded. His breathing became more panting-like and he made no move to withdraw. "You're ripping me apart."

Taking a deep breath he growled "How can I be ripping you apart with 'this' sissy little prick?" With the word 'this' he shoved in another half inch or so and pushed up against my barrier. A pain shot through me as I felt the stretching intruder probe deeper up my tight passage. Through my clenched teeth a let out a gasping moan.

'Oh, God, ' I thought 'my HYMEN!' His probing penis was now pressed into these delicate tissues. "HOWIE, STOP!" I cried out. "I'm a virgin!" He didn't shove it in any more, although I noticed I could now feel the invader twitch and pulse in place.

Each throb caused a corresponding throb of pain to be felt in my stretched and gripping hole. He continued to hold in place, neither advancing nor withdrawing. I started to plead once again "Howie, pleas..." but was cut off by the sound of the screen door banging shut. "No!" I whispered as I heard the thumps of heavy boots running up the stairs.

"Hey, Howie; look what I just got..." as the door flung open he stopped in mid-sentence. "DAMN Howie!" exclaimed Bill Baxter; Howie's best friend. I closed my eyes as hard as I could and tried to will this horrible nightmarish turn of events way. It was bad enough that my brother would do such a thing to me, but to be caught by someone else with my own brother's dick sticking up my twat was too much.

"Please Howie." I begged.

"How long you been fucking your sister, Howie?" asked Bill.

"Please." I begged my brother.

"Shit Bill, we're not fucking; just wrestling." replied Howie.

"Please." I begged.

"Well you got your dick up her cunt. It sure looks like fucking to me."

"Please."

"It was just an accident, Bill. I hardly got it in her... 'sides, she's still a virgin." he said as I felt him start to pull out. 'Thank God.' I thought as I felt my labia turn out and the head start it's exit from my hole.

"Pop her cherry, man; you heard her beggin' for it." Bill said as he approached the bed. "Let me give you a hand." With those words Howie's hips shot forward driving his dick violently up my hole. I saw stars as a searing pain exploded from my vagina. Just like that, my cherished hymen had been ripped apart and my brother was suddenly embedded all the way up my violated hole. "There ya go." said Bill.

"Fuck!" cried Howie.

"AiEEE!" I cried out.

"Well you sure are fucking her now!" said Bill.

The burning in my hole was so intense. It felt as if I my insides had been stuffed with a huge, hot pole. I had a hard time believing that my brother's small penis could cause so much stretching and pain. Then the realization that I was no longer a virgin came to the forefront of my mind. I thought I was going to be sick. I had my brother's stiff prick fully buried up my cunt and I had his best friend to thank for it. "Howie, please." I begged once again.

Howie responded this time and slowly pulled out. "God, damn!" he said and then he paused. He stopped with his prick's head still in me.

"Please." I continued to beg.

"Fuck, you're tight... aww fuck it." he said as he suddenly slammed forward to once again bury himself in my slick hole.

"Oomph, no, Howie, NO!" I cried to no avail. Howie now started to pound in and out of my abused hole.

"Yeah, she was cherry." came Bill's voice from low behind us as Howie fucked my burning pussy. He walked around to the front of the bed and said "Let's see her face." Howie pulled back at my hair forcing me to lift my head and sway my back. Bill could now see my tits. I could feel them jiggle each time Howie pounded his hard prick into me. I opened my mouth but kept my eyes tightly shut so as to not have to look into Bill's eyes. I had to protect myself from that humiliation. "She looks like she likes to fuck." said Bill. "How's the ride?"

"Umm," was Howie's strained response as he pounded away, "gonna blow." With that he pulled on my hair, back and to the side, forcing my head to the left. Suddenly his mouth covered mine and his tongue wormed it's way past my lips. As he French kissed me he slammed his pelvis hard up to mine and held himself there.

I felt a bloating and twitching from his penis and then a sudden warmth flood my vagina. Howie moaned into my mouth as he tried to shove his tongue down my throat. He hunched his pelvis at mine as his penis continued to dump it's load. Slowly, as the twitching of his penis subsided, he released my hair and let me lay back down on the bed. I felt his weigh crush me to the mattress as he started to relax.

I felt his penis slowly go limp and slip from my folds. I was in a daze. My brother had just given me my first fuck. He had taken my virginity and ejaculated into my virgin cunt. Well, I was a virgin no more! And to make matter worse, he had raped me in front of his best friend. I didn't even have the luxury of knowing that the secret could be kept in the family, so to speak. As I felt his cum start to leak out of my hole I tried to slip my wrists from my brother's relaxing grip. At the same time I heard Bill approach and felt him shake Howie's shoulder. Instantly Howie's grip returned.

"Get up man." said Bill.

Slowly Howie roused himself and climbed off my back and to the side. As I started to rise up myself I felt another body climb on my back as Bill said "My turn."

"NOO!" I shouted as Bill shoved at my recently vacated hole. "No, no, no!" I repeated as Bill stabbed at my gash with what seemed like his fist. I squirmed and bucked underneath him as I struggled to get free. I felt my pussy lips being spread with the fingers of Bill's left hand as he shoved at my hole with something way too large to comfortably fit.

With a mighty shove and grunt from Bill he succeeded in entering my vagina. I screamed at the top of my lungs and retched. The pain was like no other I had ever experienced. Fighting my stomach to not throw up, I tried to let my battered pussy adjust to the massive intruder. Though Howie's penis had caused a burning pain on his entry into my cunt, this thing that was now inside me had set my hole on fire.

"Fuck, you're tight." said Bill. "You're about to pinch my dick off." That answered my question. It was just his penis that was causing all this pain. I thought for sure that he had shoved his hand up inside of me! I tried to calm myself and get my stretched and sore pussy to accept his massive girth.

Before the burning had much of a chance to abate Bill started shoving it in and out of me. Luckily the juices that my brother had left behind somewhat helped to quickly lube his shaft and ease it's passage. My long labia were mercilessly pulled in and out with each stroke he took.

Without the slickness of my brother's cum I am sure that they would have been pulled off. My brother finally let go of my wrists as I was not about to be going anywhere; being pinned to the bed with Bill's fully imbedded penis. Bill snaked his hands under my chest and grabbed hold of my tits. Lifting my chest up off the bed, Bill pulled at and played with my nipples, all the while pounding his hard dick up my burning cunt.

Still with my eyes shut tight, I heard my brother say "That sure looks good. It would make a pretty picture."

"Feels good too." replied Bill. I no longer cared as Bill continued to pound into me. I just wanted to survive this ordeal. Suddenly I realized that the sooner Bill got off, the sooner it would all be over. Settling on a plan of action, I started driving my pussy back at him with each stroke he took. "Fuck, yeah." Bill commented on my sudden animation.

The room was soon filled with the sounds of our combined heavy breathing and the squishy smacks of our pelvises joining. My plan paid off as it wasn't long before Bill grunted and practically twisting my nipples off, shoved his dick as far into me as he could and busted his nut.

Once again I felt a warmth bathe my vagina as Bill ejaculated into my fertile hole. Again and again his fuck pole lurched and squirted out warm gobs of his impregnating stuff. Soon my twice filled pussy was leaking out much of the cum that both these teenage boys had put in there. It dribbled down my mound and dripped onto the bed in front o! f me.

"Damn, your sister is the best fuck ever." said Bill to Howie; and to me he added "I love your tight virgin pussy."

'You stupid shit.' I thought to myself, 'I'm no longer a virgin, thanks to you.' He rolled off of me and onto his back on the bed. As his penis slipped from me the burning eased and my battered pussy started to throb. It was definitely a relief to have the painful stretching replaced by just a tolerable soreness.

Looking to my right I saw Bill's blood covered and shrinking penis lying across his belly. I could not believe that something so huge had so recently stretched and poked my cunt. The monstrous thing looked to be nine inches long and as big around as my wrist!

Seizing the opportunity given me, I jumped up from the bed and ran out the door. Dashing into the bathroom, I locked the door and propped a chair up under the door's handle. Now knowing I was finally safe, I attended to my abused genitals. Grabbing a hand mirror, I looked at my gash. I was a gooey, bloody mess. My labia were swollen and red; showing signs of the friction they had just lived through.

My pussy no longer was recognizable as my own. What was once a tight slit running between my legs now was replaced with a gaping maw. I could look right up my vagina and see my cervix. All over were slimy deposits of blood streaked, whitish blobs. More of the shit drooled down out of my gaping tube to run down my legs and drip onto the bathroom floor.

Turning my attention to my poor, abused nipples, I saw the little cones puffed out like never before. They were extremely red where Bill had twisted and pulled them as he fucked me. I now realized they too were throbbing in unison with my fucked hole. I heard my brother and Bill, laughing, run down the stairs and out the front door.

At that point I turned away to look in the above sink mirror. On seeing my own reflection in the looking glass the recent events of the morning washed over me and made my stomach flip-flop. I gagged into the sink, not able to bring anything up and then collapsed to the bathroom floor and broke down crying. As I hugged myself in a fetal position, I cried for my lost hymen. I cried for my sore, abused nipples and pussy and I cried for my lost innocence. I stayed there for I know not how long before venturing out to lock myself in my room to cry some more.

I could not believe how stupid I was to have brought this on myself. What if I had not teased my brother so? What if I had not exposed my tits and bush to him? What if I had not gotten totally naked with him and taunted him with my pussy? What if, all along, we had had a peaceable, loving sibling relationship? So many 'what ifs' ran through my mind that afternoon I lost count of them all.

Nothing would be the same now; not the relationship between my brother and me, not the way Bill looked at or treated me, not my cum filled, stretched out pussy, not my confidence in myself and not the way I saw myself. Off and on I cried to myself for a week and a half.

It was a Wednesday morning, after third period, when I found the photo spread in my locker. They had been stuffed through the door slots and were sitting on top of my books. I gasped and quickly covered them up, glancing around to make sure no one else had caught a glimpse.

Running to the bathroom I secreted myself in a stall and stared in disbelief at the pictures of ME! There was a close-up from below and behind of my bloody pussy lips, a cock up my twat, being deflowered by my brother. There was a side shot of Howie mounting me from behind. There were close-ups of my face with my eyes shut and my mouth open, giving the impression that I loved what my brother was doing to me.

There is no doubt who the participants were in the pictures and what we were doing. God; the ones of me and Howie French kissing as he fucked me were disgusting! There were pics of my fresh fucked, gaping slit oozing big globs of bloody cum while my brother's red prick dangled beside it. There were shots of Bill's big dick splitting my gash and filling me up. Just looking at Bill pulling at my nipples as he fucked me silly made my pointy tips ache anew.

As the visual evidence of my first fuck sank in I noticed the note slipped among the proof sheets. It was short and simple; just telling me when and where to show up. As I stared at the sheets in my hands I tried to figure out how could this be? Then I remembered Bill being all excited when he first ran up the stairs and entered the room, saying he had something to show Howie. It must have been a digital camera and I, with my eyes shut, posed so nicely for them both!

I walked around numb and in a daze for the rest of the day. At 2:30 I arrived at the deserted back of the stage off the auditorium in the boy's costume change room. As I entered, I notice that there was nobody in the room. It was lined with clothe racks filled with costumes. In the middle was a large table. A few scattered chairs finished off the room.

Just as I was beginning to hope that maybe he wouldn't show, Bill entered, closing the door behind him. As he turned the latch, locking us in, my heart sank to the pit of my stomach. Looking me over, Bill said, "I see you got the pictures. They came out kind of nice, if I do say so myself. If you want to keep them from being plastered all over the school you'll walk to that table and lean across it... after first taking off your panties. I need some more of that tight pussy of yours."

My mouth fell open and I stood and stared at him.

Raising his voice a bit he ordered, "NOW!"

As a tear rolled down my cheek, I turned and walked to the table as told. I reached under my knee length skirt and pulled down my panties. Kicking them off, I leaned face down across the table. I heard a rustle of clothes behind me and Bill's chuckle. He stepped up behind me and kicked my feet out to the sides. I flinched as I felt him flip my skirt up across my back and run his hand over my naked ass. I flinched once again as he leaned in and touched his penis head to my pussy lips.

With cock in hand he then started rubbing the head up and down; up and down my pussy's gash. He kept this up for two or three minutes, going slightly deeper as time went on until he was traversing the bottom of my cleft from asshole to clitoris and back again. From the moment he touched me with it, his penis was leaking out a slimy wetness with which he painted my gash. He also started to dip into my wet divot and accumulating my dew on his dick head, spread it about.

As if to betray me, my hole started to add more of it's own juices to the quickly moistening dance his dick was making with my pussy lips. Then on one pass through my divot he stopped and slowly applied pressure. As my eyes sprang wide open I felt his head push through my folds and begin to sink into my cunt hole. A groan escaped his lips as his dick sunk deeper into mine.

I was surprised that I did not feel the same pain as last time. The stretching of my vagina was still there but the burning and soreness were gone. He paused, pulled back slightly and then continued forward once again. This pattern was repeated several more times before he bottomed out in me.

"God damn girl, you've got the tightest pussy." said Bill as he started a slow fuck of my hole. I felt him slide his massive dick almost all the way out of my pussy before reversing direction and fully burying himself in me. I once again noticed how my long, slick labia would follow the passage of his massive pole; pulling out and puckering in with it's movement in my cunt.

Bill was now moaning constantly and starting to pant. He picked up the pace with which he fucked me and soon was smacking my bottom with his thighs each time he bottomed out in me. "I'm gonna cum." said Bill as he really started to pound away.

'Oh, FUCK!' I thought as the danger suddenly dawned on me. In my shock I had only concentrated on what would happen if the photos got passed around the school. When my brother and Bill first fucked me I had just finished my period. Now I was entering the fertile phase in my cycle and I could get pregnant. "Bill, NO," I pleaded, "don't cum in me. I could get pregnant."

He continued to pound away in me.

"Please Bill, please; I don't want a baby."

If anything Bill sank harder and deeper into my pussy. "Bill please," I added with a sob, "don't fuck a baby into me. I'll do anything you ask!"

With a mighty groan from Bill I felt the full length of his dick lurch.

'Fuck!' I thought 'He's cumming.' My heart sunk as I waited for the walls of my vagina to be bathed with his hot, impregnating goo.

Suddenly Bill yanked himself from my pussy and blasted my bottom with his spunk. 'Thank God' I thought. Grabbing his cock, he pressed it's head to my butt hole and went off again, coating my puckered hole and forcing some to shoot inside. Pressing a little harder, his third shot went through my asshole and into my bowels lubing it with his slippery deposit.

With a sudden lurch he chased the cum wad up my butt with his lurching dick head and crammed his penis in me. "NoooaAGH!" I uttered as my bowels were speared by his penis. The memory of the pain of my first fuck returned as I thought my ass had been ripped apart. Bill hunched at my butt as he fucked the last of his cum up my poop hole.

When his dick stopped pumping, Bill sighed and laid across my back. I softly sobbed my tears onto the table top as he slowly shrunk and eventually popped from my poop chute. I puckered my burning sphincter to try to keep the cum from dribbling out.

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A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

1 year ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

2 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

1 year ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

1 year ago
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Cuckold Sissys First Meet Fantasy

This fantasy summary was sent to my wife and her prospective boyfriend to let her boyfriend know our fantasies and for me to know which bits got my wife and bf really wet? And feeling very horny? Which bits she really liked? And what they would you like to add to also?The text was sent to the prospective boyfriend's iphone with a picture of me on all fours showing my girlie soft pathetic knickered and caged boi-clit after he sent me a picky of his gorgeous cock which I had previously been lucky...

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