Turned Into A Sissy Baby free porn video

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Turned Into A Sissy Baby


I was terrified at the prospect of being turned into a girl. I mean it’s one thing to do it alone in your bedroom from time to time but another thing entirely to have beautiful women see you in a dress. I don’t think that’s the best way to get girls. But due to hard times I needed a place to stay and some extra money. A group of experts were offering big bucks (like 25 million) to a group of men with different views of womanhood and feminization. I was lucky enough to be chosen.
So I packed a bag with all my essentials and hopped a private jet to an even more private island over 20 hours away where my transformation would be taking place. The only building on this island was a gigantic castle. With all its separate towers and turrets it was far more than any princess would dare to dream of.
I was led into the main entryway by a man (surprisingly) then 2 tall and extremely attractive brunettes who looked about in their twenties took me down a series of hallways so vast I’d never be able to find my own way out. Clearly some of the men here tried to escape in the past.
I was at last brought into a master bedroom of bright magenta walls with white trimming and carpeting. A big bay window looked over the grounds and there was a giant canopy bed in the middle of the room hung with white lace and covered in pink satiny sheets. Also a large vanity complete with a professional chair, sink and tub was over in the corner. Double doors opened to what I assumed was a closet and a door off to the side which could only lead to a bathroom.
I was so taken aback by the immediate girlishness of the room I didn’t even notice the three women who occupied it. One had black hair and was hovering around the vanity, the other had red hair and stood near the closet, and the last was a blonde who sat on the bed. They were all exquisite, subtly beautiful.
“Well, well, well. It looks as though the girl of the hour has finally arrived!” exclaimed the blonde. I noticed she was probably in her mid to late forties. A definite milf.
“Now don’t just stand there girl! Take your clothes off for us!”
For the record let me just say that I’m a 5’10 guy with shortish brown hair and a pretty thick build. By no stretch of the imagination was I a girl….yet.
I stood there awkwardly and she said in a softer tone, “No need to be nervous dear. We won’t judge a thing.”
Surprisingly I believed her. I trusted her for some reason and I stripped naked, slowly, in front of them, feeling like I’d never be the man I was now again.
“There we are darling. Now don’t you feel better already getting rid of your old clothes? They did nothing to show off your girlish, curvy figure at all!”
Girly figure? Hardly.
“Now then dear, before we begin I want to be absolutely sure you know what you’ve gotten yourself into. We are transforming you into a lovely little 4 year old girl named Sally, and you will need to relearn everything you’ve known. We are essentially building you back up fresh from scratch. Are you ready to be turned into my beautiful little girl?”
For 25 mil? Absolutely. Turn me into a damn pigeon for all I care.
“I’m ready.”
“Ah, ah, ah say it correctly dear. And from here on out you’ll be referring to me as mommy,” she said with a smirk.
Well that sounded kind of stupid but alright. “I’m ready to be turned into your little girl mommy.”
“Hmmmm, well you don’t sound much like a little girl to me. Higher darling, much, much higher.”
Feeling very stupid now, but also wanting to please “mommy” I said in a near impossible pitch of falsetto, “Yes mommy I really want to be transformed into your pretty little girly girl.”
“Excellent Sally, excellent! Now sissy is going to take you into the tub and shave you bare and then the really fun part begins! See you in a little while sweetie!”
The red headed girl led me into the bathroom which was done completely in lavender. There was a smaller vanity in here with a high chair and an enormous shower, also (strangely) containing a chair, with restraints on it.
“In you go Sally.” Sissy said. She had a surprisingly husky voice.
She strapped me into the chair feet first, then my arms. My neck, luckily, was kept free.
“Just a precaution honey, try to enjoy it.”
She turned the shower head on which doused me in refreshing warm water. When I was finally good and soaked she slathered me in a sweet smelling body wash and began shaving my toes.
That was kind of embarrassing. I didn’t even realize I had hair there. Next she began shaving my legs very slowly. I became a bit scared when I saw how feminine my legs looked hairless but tried my best to think about the big payoff.
Next she moved to my penis, chest, then my arms, then my armpits. Finally I was completely shaven and my skin felt silky smooth. It was pretty sickening.
“Very good Sally,” Sissy encouraged as she undid my restraints. “Come here and let me dry you off.”
She dried me very slowly and took her time around my newly shaved penis clearly making sure she hadn’t missed a spot. I was beginning to get a raging erection from all her fondling, but she acted as though she didn’t notice. Thank god.
She hung the towel up to dry then headed me back into the bedroom. “Lie down on the floor sweetie, and we’ll get you all diapered up.”
Did she say diaper?
“Oh darling we have to take care of that now don’t we?” Mommy said as she walked back into the room eyeing my erection. “Keep that thing it a cage. Sissy give him a chastity before his diapering.”
“Wha- bu-,” I sputtered. “I thought I was being turned into a girl. I don’t want diapers or a chastity!”
“Ah, ah, ah Sally. We don’t want a spanking do we?” Mommy asked as she produced a large and menacing looking whip.
No we didn’t want that.
My erection died as my manhood was packed away into a tiny pink chastity with a big silk bow on it hiding my penis entirely. If anyone were to see me they would clearly think there was nothing there. Sissy then pulled out a bottle of baby powder and powdered the area around the chastity.
“Flip over sweetie,” she commanded softly.
I flipped. I didn’t want that whip.
She sprinkled the baby powder onto my bottom and again asked me to flip.
Now she produced an adult sized diaper covered with little ducks. She lifted my legs into the air and put my ass on top of the diaper. She folded it up over my little bow so it was finally out of sight, and then did up the sides.
And boom I was in a diaper.
“Let’s take a look in the mirror shall we Sally?” and with that mommy pulled me to my feet and flung open the closet doors which revealed girly dresses and ballet shoes galore. She stood me in front of the full length mirror and chained my feet and arms behind me so I couldn’t move and I was forced to look at myself.
“How do you feel Sally?”
“Ridiculous,” I choked out in my falsetto voice.
“Well then you’re just going to have to stand there until you learn to appreciate your diaper and your new self a bit more. I was left there for about five minutes standing face to face with what I had become. When she finally came back I was ready to do anything to get away from that mirror.
“Shake your little bottom Sally.”
I wiggled my hips around as best I could.
“How does that feel?”
“I feel like a baby girl mommy.”
“And that’s exactly what you are.”
She unhooked me and led me over to the vanity chair.
“Now it’s time to sit back and relax darling. Cuzzie (apparently that was the black haired one) will be giving you a manicure and pedicure while I work on your hair. I’ll be giving you a head full blonde curls!”
Oh joy unbounded.
I took my seat cautiously. It was petrifying to be demasculized like this. Throwing away everything I was ever told. But it was also such a rush. It felt so forbidden.
As Cuzzie got to work on my toes Mommy began bleaching my hair out with peroxide.
“Don’t I get a wig,” I questioned softly.
“Oh heavens no Sally. How could you ever be a real girl with a wig? You’re getting extensions and a perm angel. Nothing but the best for my baby doll.”
Now I was getting really, really anxious and as the bleach started to burn my scalp I focused instead on my toes. Already, with no polish on them, they were much more girlish looking. Expertly manicured and lotioned. Then, just as Cuzzie started applying the purple polish my neck was forced back as my hair was washed out.
I looked in the mirror to see that my locks had become white blonde. Shocking. I hardly recognized myself. Mommy then stepped in front of me with a comb and scissors. Oh no.
“Hold still now Sally. Don’t fidget.”
She parted my hair in three ways. Front, left, and right. Then she clipped me a set of bangs that barely brushed my eyebrows. Now I really was scared. Those bangs made me look like a little girl. There was certainly no going back now.
She began threading the extensions through as Cuzzie moved to my hands. She was applying neat little tips which I could already tell were going to get in the way of even the simplest tasks. By the time she was finished painting them a dark lavender mommy had finished my extensions.
My head felt much heavier. And yet it became heavier still as she started expertly knotting my new hair around little curlers. Hundreds of them it seemed.
“Oh Sally,” she gushed as she worked. “You are going to be such a pretty little girl! I can’t wait to get you into your big poofy dress. And just wait until we get your hair set in matching piggie tails and little bows!”
That sentence just about drove me wild. After my hair was all set up in the curlers, Sissy waxed my eyebrows into teeny tiny arches. It hurt so bad I started to whimper. The little girl thing was already having an affect on my personality if I was sitting there whimpering rather than screaming obscenities.
“Let’s get you all dolled up nice and pretty now,” mommy said as she pulled me from the chair and over to the bed.
“Now sit here darling and start putting things on as I hand them to you.”
The first thing she emerged with was a pair of white tights. Shockingly, they were large enough to fit me, diapers and all, but didn’t sag in any spots. As I slid them up my now hairless legs I really did start to feel like a girl.
“Oh don’t you look adorable in your little tights! They show off your legs so well!”
The next thing she came out with was a set of gigantic petticoats. They looked like they were made for a giants daughter.
This was it. The part where the real girlishness kicks in. I slip the petticoats up my tighted legs and set them between my waist and my navel. They stuck out two feet wide in all directions. I was aroused.
“Why you look like a little ballerina darling! But no little girl is complete without her corset. I’ll have to do this for you sweetie.”
She walked over carrying a white corset and put it over my chest then started tying it tightly in the back.
“Of course we’ll have to pull it tighter and tighter in the following days but for now I think this is a good place to start. Are you comfortable sweetheart?”
“Yes mommy, I’m fine,” I squeaked.
Finally it was time for the dress. Mommy pulled it from the closet with a flourish and slipped it on over my head then zippered up the back.
It was a bright pink color with huge poofy sleeves. The petticoats had it jutting out so that my diaper was only just visible. It felt….amazing.
“Oh look at my pretty little girl! You look so adorable in your poofy dress and tights! Are you ready for your shoes?”
“Yes mommy!” It frightened me of how accepting I was of my transformation but I felt so pretty and girlish I wanted nothing more in the world.
She handed me a pair of shiny black tap shoes that fit me like a dream.
“Swish your dress around like a good little girl for mommy.”
I started swishing my hips to the left and right, fingering the bottom of my dress.
“What a good little baby doll you are! Now turn around and touch your toes with your legs together so mommy and sissy and cuzzie can all get a look at that cute little diaper you have on!”
I eagerly turned around and showed them all my bottom. They all laughed with glee. “Oh how adorable is she! Look at that little blush!”
“Speaking of blush,” mommy said “it’s time to finish up her hair and get started on her makeup. Come on my little Sally, back over to the vanity! And this time lift your skirts before you sit down.”
I made my way over slowly as my petticoats and dress swished with every little movement. I did exactly as she said and slowly took my seat.
Sissy began taking out my curlers and once all my hair had come down I was spun around to face the mirror. My curly blonde hair hung past my shoulders and was curled to perfection. I was a baby girl.
Mommy took her comb and made a straight line down the center of my scalp. She took one side and brushed it up as high as it would go, almost to the top of my head. She knotted it there with a plain white hair tie and repeated the process on the other side. She used a round brush to swoop my bangs down then curled them under. At last she added two big bows to the tops of my pigtails.
“Oh look how cute my little daughter is! Wiggle your head back and forth for mommy. Let me see those pigtails bounce up and down!”
Loving all of the attention I jangled my head back and forth with a little giggle.
“Atta girl! Now there’s just one thing missing. Every pretty girl wears dangly earrings to frame their face. Hold still baby and this won’t hurt a bit.”
I got a bit scared when I saw the needle but surprisingly when she pulled the needle in and out of each ear followed by huge pink sparkly heart earrings I felt no pain. Just some additional added weight.
“Now wiggle your head like a cute little girl for me baby. And do that darling giggle again.”
I shook my head with added vigor giggling loudly and playing with my pig tails. My actions were getting me more aroused than I had ever been in my life!
“Oh Sally you’ve been such a good little girl for mommy through all this! Let’s practice a few poses. I want you to skip across the bedroom for me. Let me hear that cute little giggle once more.”
I stood slowly and ruffled out my pretty pink dress then shook my bottom. It made sissy and cuzzie laugh and I started to giggle uncontrollably. I started skipping across the room.
“Very good Sally! Now come back to the middle of the room and give us all a nice little curtsey.”
I pinched my dress between my fingers, crossed my feet at the ankles and bent my knees forward.
“Perfect darling! I’m pleasantly surprised that I don’t need to teach you anything about your form. Something tells me you were fond of playing dress up!”
At that I felt my cheeks brighten again. I’d never blushed this much in my life.
“Oh heavens dear I almost forgot your makeup! You look so girlish even with nothing on! Come sit down.”
Cuzzie came over and started applying my makeup. She put on a cover up and foundation, then pale pink lipstick covered by a shimmery gloss. A lot of blush. My cheeks were now permanently rosy red. Bright blue sparkly eye shadow and a ton of mascara that made my eyelashes about an inch long!
I looked like a gorgeous beautiful girly girl baby doll. Then mommy gave me a fuzzy pink purse and said we were going to run to the store.
“But everyone will see me mommy!” I immediately protested.
“Why of course dear that’s the point! You’ve been so good Sally don’t start fussing now. I don’t want to have to spank you.”
And I could tell from her tone and her eyes that she meant it.
“Okay mommy lets go.”
“That’s my girl!”
I was led down a different set of hallways and out of the back of the castle this time to an expensive looking convertible. I made my way to the passenger side but then mommy stopped me.
“No one under twelve in the front seat silly. Come on I’ll strap you into your car seat.”
“But mommy!” I fought.
“It’s the law,” she said shortly.
Grumbling, I scooted myself into the large car seat and allowed her to snap me in extra tight so I couldn’t move a muscle.
“Feel free to have a little fun back here sweetie,” she said with a wink.
Ah very clever. The car seat was like a type of bondage. I could feel the tingling between my legs and began to think all the things I needed to too get me aroused.
You’re dressed like a baby girl. You’re wearing a diaper and a poofy pink dress. Your hair is set in curly pigtails with cute little bows! You look absolutely ridiculous and now are going to be humiliated further being put on display like this.
My penis was aching with pleasure at all this but the chastity prevented an erection so I just squirmed and moaned a lot. Mommy either couldn’t hear me over the wind or pretended to be unaware.
By the time we reached the downtown area I was exhausted from my ‘masturbation’ session and did not protest to having to sit in the (modified) seat of a shopping cart with my feet and hands chained down. This area was bustling as if everyone from the castle and their parents were here. Some people laughed, some awed but everyone looked at me.
“Just smile sweetie. They can’t take their eyes off you because you’re such a pretty little girl.”
“What are we here for mommy?” I was surprised there would be anything here that wasn’t already in the castle.
“We’re going to get you your own stroller honey! A reward for doing so well today. And maybe we can get you a cute little bonnet too for your extra effort!”
“Okay mommy,” I said dejectedly. I wasn’t having much fun anymore.
“Oh you’ll cheer up once we get to the store.”
And shockingly the second we got inside I felt the excitement return. There were all sorts of baby girl things in here.
“Mommy can I get down and look?”
“Ah, ah Sally. I need to keep my eye on you.”
All around me were men and boys dressed up like girls. Some babies, some in their seventies. All in very feminine baby attire.
“What do you think of this one Sally?”
I looked to where she was eyeing and saw a frilly pink stroller loaded up with white restraints.
“Can I play in it like I did in the car seat?”
“If you listen to mommy then you can sweetie!”
“Okay! I’d love it please mommy!”
“Excellent.” Mommy started pushing the cart and stroller up to the register.
“I have to use their bathroom, can I get down?”
With a laugh that made me feel as though I wasn’t in to anything good mommy replied, “Oh honey, you’re a baby girl! That’s what the diaper is for.”
“I can’t go to the bathroom in a diaper!”
“Ah, ah, ah, it’s called potty Sally, and you’ll just have to get used to it. Now which will it be? Hold it in and get yourself sick and spanked or go now?”
With a sigh I gave in. “I’ll go mommy.”
“That’s my pretty baby girl.”
I had no choice. I had to take a **** right then and there sitting in the shopping cart, chained in, in my diaper. A wiz too which was no easy task with that chastity.
As mommy finished up paying for my new stroller she kindly asked the cashier if we could use their bathroom.
“My daughter here needs a diaper change,” she said motioning over to me. I put my head down and blushed fiercely as the girl took me in.
“Sure,” she said not looking surprised at all by my appearance. “In the back and to the left.”
With a thank you Mommy finally unlatched me from the shopping cart and pushed the stroller into the back leaving the shopping cart up front. She was carrying a diaper bag which I hadn’t need until now. I felt extremely uncomfortable.
The bathroom consisted of 5 long rows all carpeted with doors and mirrors. More of a dressing room than a bathroom. Only difference was there were mirrors on the ceiling, so I got to see myself for the freak I now was.
Mommy put down a changing pad (Guess what color?!) and told me to lay down. As I laid I could see my pigtails fan out around my head and my dress get all pushed up and look even poofier.
“Lift your bottom for me dear.”
I did as I was told and mommy pulled off my shoes, tights, and petticoats. She then pulled up my dress. My first ever changing. Well, at least as a girl.
I don’t want to get into the details but mommy at least let me take off my chastity and keep it off for the rest of the day until bed time.
“For being so good today,” she said with a smile.
“Yay! Thank you mommy!”
I looked back up at myself in the over head mirror as mommy slip me back into my diaper and the rest of my outfit. I took in my painted lips, my rosy red cheeks, my adorable baby diaper and immediately I grew erect.
“Oh Sally you’re such an excitable little girl!” mommy said. “How about we freshen you up a little while were in here dearie?”
“Oh yes mommy please!”
With that mommy had me sit on the floor in front of her while she kneeled over my head and took out the pigtails. She shook my hair out and then produced a large bottle of super extra hold hairspray.
“Stand up now sweetie and bend over to the front.”
I was a bit confused but did as I was told. Mommy raked my hair straight down and then tied both of the hair ties around it very tightly and securely right at the very top of my head.
“Now sit back down honey.” She took the huge can of hairspray and spritzed my hair fiercely until it was standing straight up on its end. She played with the top a bit and quickly had it fanning out like whisps. She then took one of my two bows and secured it tightly at the bottom.
“There we are dear. That will keep the hair out of your eyes! Oh you look so darling! Get up and jiggle a bit for me.”
So with my new hair bouncing at every step I took I stood up and pranced around holding my skirts for my mommy. I couldn’t help it. That high pitched giggle escaped my lips again as I lost myself in playing.
“What a good girl you are! Come hop in your new stroller.”

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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...

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