[dionnespet]

every day it was the same - his step daughter would bring another of her friends home to witness his servitude and humiliation.

all the young women got off on punishing and degrading him. each day he suffered pain and frustration as they would tease and torment him with their sexuality.

yet they had trained him so well he longed for tomorrow when it would all begin again.

[aisissyfun]

[valeriesimms]

Imagine if this were truly possible 🥰

[daddys-sissy-baby-girls]

I used to be a bad boy and cheat on my girlfriend but when she found out she taught me a lesson. I’m a good girl now and my girlfriend is now my Mommy. She decided I could stay with her but I am a diapered sissy maid now who does whatever Mommy tells me to do. Now I get to wear cute clothes like frilly maid’s dresses, adorable shoes and comfy tights and thigh high socks. I have to wear straps round my ankles and wrists at all times but only so Mommy can keep me restrained whenever she needs to. I have a really cute pink collar as well so that Mommy can take me out on walks so I get exercise. My favourite things to do are cleaning the house and eating Mommy’s pussy when she gets home from work. And Mommy rewards me for being a good girl by putting my vibrating but plug in. It’s the only way I can make cummies since Mommy put my clitty in chastity so I’m so grateful to Mommy for allowing me that. I’m happy like this, honestly.

[sensuallyspanked]

But you still need regular maintenance spanking

[man2maiden]

[iamasissy23]

My dream

[sissyjamiedreamer]

A perfect way to spend a couple of hours. For both of them.

[sissyjamiedreamer]

They used to be happily married but their relationship had become boring for her in recent years. So she decided to spice things up a bit. A perfectly reasonable solution to a stale marriage. Don't you agree?

[man2maiden]

[babybobbysstories]

Sissy Captions #27

[onesubbyfemboyyy]

Spending time in my rightful place 🤍🔐

[sissyjamiedreamer]

On his third day as office maid, after he got changed into his uniform in front of Victoria, she revealed the ball gag he was to wear. Due to his frequent complaints to the women in the office and petulant reactions to being bossed around they had decided to silence him for the time being. Of course his reaction to being forced to be a maid were completely justified, but women wanted to foster a mentally in him that he was the one being unreasonable.

[sissyjamiedreamer]

Carla and Simon's parents passed on when they were younger, so Carla had raised Simon for the last ten years. Now she was a very successful 32-year-old business woman and very driven. Simon on the other hand was completely the opposite. 10 years younger than Carla he still lived her but he hadn't found a stable job. And spent long periods unemployed. Thinking this was unacceptable she decided to put him to use around her large house. Together with her housekeeper, Audrey, they gradually tested the waters in how much they could boss him around. To the surprise he was quite submissive and a very diligent with his chores. It even seemed therapeutic for him. Over time Audrey was doing less and less housework and now acted as his matron/supervisor. She even start having him dress as a maid. Just simple outfits, a white blouse, knee length black skirt and comfortable smart trainers. Carla loved it and to their surprise, Simon, although slightly reluctant, wore the clothes without argument. He now did all the household chores with great efficiency so Carla and Audrey now decided to go all out and turn him into a full on sissy French maid, and him serve them and other women drinks and afternoon tea, on top of his chores. In the scene above Carla has taken him dress shopping for his sissy uniforms. Although he was deeply embarrassed at his first public outing, he obeyed his sister without question and tried an array of delightful sissy attire.

[sissyjamiedreamer]

[abobachann]

The store lights hummed, but all I saw was her, holding the stack of diapers like a trophy. My new life, all wrapped up in plastic and promises of permanent change. Each package represents a step further into my feminization, a constant reminder that my old life is gone. She chose those pastel colors, just for me.

I tugged at my pink pajamas, the floral pattern a pathetic attempt to retain some shred of masculinity. It didn't help. The diaper beneath felt thick and undeniable, a permanent fixture. My body is hers now. My money, my time, my very existence, all feeding into her Findom desires.

"Do you like your new diapers, sissy?" Her voice was soft, but edged with command, her eyes never leaving me. "They’re a good fit for my little girl, don’t you think? You should thank me. You look so pathetic.”

I swallowed, a lump of shame rising in my throat. I knew I should be grateful, for every single purchase, every single decision, because every single dollar went to her, to further my transformation. She is my goddess, the architect of my permanent future. This isn’t just a phase, this is a new me. A permanent me.

"You know, baby, these new diapers are just the beginning,” she continued, her lips curving into a smile. "We're going to make you so very pretty. Isn’t that right, princess?”

I nodded, my gaze dropping to the floor. My new permanent reality was a blend of embarrassment and anticipation. I knew, deep down, that she'd always have me right where she wanted me. My heart is now hers. And my money is too. This was permanent.

[cleversissy]

Is this what heaven looks like? Me kneeling before my omnipotent Goddess for all eternity? Forever in service to her?

[iamasissy23]

I want a goddess to worship!!!!

[made2play]

You and your girlfriend are fiercely competitive. While watching a Poker game on television. Both of you are drinking and carrying on. Both of you declare. They are the superior poker player. So your girlfriend suggests a poker game. You agree. Not knowing how competitive she is. She says best two out of three. You play the first game you win. You play the next game. She wins. Now the pressure is on. As the cards are being dealt. She says, “ Let’s make a bet?” You say, “Why not? What should we bet?” She suggests a Winner Takes All. You agree not knowing exactly what she meant. She starts the deal. You sweat the moment. Time to show your hand. You lay your cards down. She lays her’s down. In absolute astonishment you lose. How did this happen you think? Before you say anything. She says, “Time to pay up!” She leads you to another room. You see a bed. On it is a total sissy outfit. She reminds you that you lost the game and you gotta pay. So you agree. She helps you dress. As you put on each piece of clothing. You feel a tingling sensation in your penis. You are dressed minus panties. She does your hair and make up. You’re getting hard now. You fight it, but you’re loving it. Now she hands you the matching panties. She tells you to wait. Just two more things are needed. A cock cage and plug. She cages you and plugs you. Then you put on the panties. You are in total bliss. When you accidentally tell her you love dressing like this and that you never want to be anything more than her sissy. She strokes your face and tells you she always knew and the game was fixed. Now this is your new life. It’s not a dream.

[sissybabydaisy]

Now is not the time to be fussy sissy girl, mommy has a date and hes taking me out of town for the week. If everything goes as planned you'll be getting a Daddy when I get back. He's been asking about you more and more and he even said he would love to change a sissy diapy soon. Now all that being said mommy can't leave you here alone for a week with no one to take care of you can she? No no no, you know sissies can't change their diapys or get there own foods, and most importantly a sissy can never ever have any access to her sissy cage. That belongs to mommy and soon daddy will get the only keys to that cage by the way and he said he's going to glue both the cage and lock so it cannot come off until he cuts the cage. Also daddy told me that your wearing no less than 3 diapers at a time. Mommy will cut them so they leak into each other. Daddy said he likes the idea of you not getting a diapy chabge for as long as possible.

Ok now that we got you diapered and dressed up mommy has some advice for you if your going to get along with your sissy baby sitter. I have been talking with her for a few months about you and everything you had on your tumblr that landed you in this mess. Shes 19 and she is a total fucking brat. Now she has a kink of her own and that is pushing and breaking men's or in your case sissies limits. She knows all your kinks and fears and she has already told me a few of the ways you'll be spending your time with her and all mommy has to say is . . . When your crying and blathering like a real baby remember this is everything you had ever wanted and even not wanted to have happen. She works as an intern in a fertility bank. She has access to all the samples real men deposit as well as all the funky jizz that doesn't meet the cut. She said she has more cum saved up for you than 2 whole sperm banks have ready to sell.

Ok she's here little girl im going to greet her. Mommy loves her little sissy girl. Now fill those diapys and mommy will be getting updates from your sitter. Hi sissy girl my name is hah like id tell you. If you are allowed to speak you'll address me as Goddess. I own you as of right now. I've got your sissy dick cage keys in my purse and a tazer on the table. You'll be wearing a shock dog collar as well to ensure you don't get any silly ideas you little bitch. I'm not your mommy I don't have to be sweet, or kind, or even acknowledge your alive at all. Now I'm going to get some dinner and your going to watch me eat it all and then your going to sniff my feet and my ass while I watch some of my TV shows I'm way behind. Ok good chat.

[sissyjamiedreamer]

Back after a short break, and straight back to posting again.

Here Sissy Jamie has been instructed by his Mistress to keep his hands in a new position whilst walking from now on. The ribbons tied to his wrist connect to his collar, preventing him from dropping his arms. Ensuring a delightful sissy pose.