Archive for the ‘sissy boys’ Category

Awakening of a Sissy: Part Three

February 7, 2014

Previously, from Awakening of a Sissy: Part Two

Sylvia told the baby to get up and assisted him in climbing into his crib. She smiled at him as she locked the door behind him. “No story tonight, you disobeyed Nanny” she said as she blew him a kiss and walked out.

 

…the story continues…

A Sitter for the Sissy

 dressing sissy

Jake tried to go to sleep, but his mind was racing. Who did this Sylvia lady think she was? Why was he so incredibly turned on by the way she treated him? He had longed for this for sometime. Now that it had actually become a reality though he was terrified. He suddenly realized that he could hear his mother and Nanny Sylvia talking in the next room.

 

“I will have to take a short leave of absence next month for a previously scheduled appointment in Paris.” He heard Sylvia say. He got excited thinking things might go back to normal for that time.

 

“We’ll have to start interviewing sitters immediately.” His mother responded. “I don’t want just anyone involved in Jackie’s care.”

 

Jackie??? He thought to himself. She is already referring to me as a female, as a girl. Jake was amazed at the series of events that had taken place. Soon though he was drifting of to sleep.

 

Jake woke up to the sound of voices the next morning. It seemed Nanny Sylvia was on the phone with an associate. From what he gathered the woman’s name was Cindy and she had worked with adult babies before.

 

“Oh I’d love to bring Jackie and his mother by this afternoon.” She said cheerfully.

 

Jake felt his heart sink. He was going to be taken outside of the house with his mother and Nanny dressed as a baby girl. He tried to fight it but the tears came anyway.

 

“Oh Baby is awake, I will call you before we head for your place, bye for now.” she said and hung up. Jake listened to the sound of Nanny Sylvia’s heels as she approached. The crying was out of control now.

 

“What’s wrong sweet pea?” she asked him. Jake just stared at her face. How could she not know what was wrong? Everything that was his was taken and he was being turned into a sissy, or a girl. This strange woman was arranging for someone to babysit him in her absence, and he was old enough to have kids of his own. What’s wrong??? He thought. What a ridiculous question to ask.

 

“Jackie, I asked you a question,” she said.

 

“I’m scared,” he sniffed. “I don’t want to go outside and meet a sitter; I don’t want to be a baby girl.”

 

Nanny Sylvia studied his face. Then she reached in to wipe his tears with a cloth diaper. “Well that’s too bad Jackie, you will just have to grow to like it,” she told him. She walked to his closet to find clothes for him. The Nanny pulled out a thick pastel pink petticoat and laid it on his changing table. He heard the rustling as she came out with a frilly white dress with pink ribbons on it.

 

He was taken from his crib and over to the changing table. Nanny Sylvia hummed as she changed him and put him in thick cloth diapers. He was surprised this time that the rubber pants were not of the locking variety. He assumed it was because they would be close by. Once he was dressed in his layers of ruffles, he was put in thick white tights and white patent leather Mary Janes. When he looked at himself in the nursery mirror he was shocked at how girlish and babyish he looked.

 

His Nanny presented him to his mother and they left the house to meet his potential sitter, Cindy.

 

 

…to be continued…

 

 

Scarlet

1.888.430.2010

Awakening of a Sissy: Part Two

January 10, 2014

Previously, from Awakening of a Sissy: Part One

 

“Oh but you are a sissy baby, Jakey you are. “ Sylvia said as she rubbed his shoulders. “Now it’s time for me to show you where you will be staying from now on.” She said.

…the story continues…

The Darling Nursery

the darling nursery scarlet 1.888.430.2010

Sylvia took Jake by the restraints and walked him to his mother’s ‘library’. “I don’t believe you have been in here in quite some times have you angel?” she asked. Jake shook his head no slowly.

 

As Sylvia opened the door Jake was amazed. The rows of bookcases had been replaced by larger sized baby furniture. In place of his mother’s reading chair was a glider rocker. Soon his eyes moved across the room to the crib in the corner. It had a locking door and high sides. Above the crib hung a beautiful mobile playing soft music.

 

“Jakey, on the changing table little one,” Sylvia said. He looked at her sadly but climbed up on the table. Sylvia pulled his panties down and tossed them into a laundry basket. She hummed to herself as she carefully folded a cloth diaper and slid it under his hips. Jake watched in horror as she reached down into the compartments on the table and grabbed an interesting pair of plastic panties. They were light pink with lots of white ruffles.Sylvia motioned for Jake to flip over and she snapped something on the panties.

 

“They’re locked in place now Jakey – they will stay in place until your mother or I change you.” She told him “Now that bra must come off; you aren’t old enough for a bra yet girl.” Sylvia unhooked and removed his bra.

 

After he was diapered and locked into his panties his new nanny helped him from the changing table. He was told that unless told otherwise that he was to crawl. Having reached his limit Jake continued to walk about the nursery.

 

“There is no use in trying to fight this baby, you are what you are.” Nanny told him as she grabbed his wrist. She walked him to the chair and pulled him into her lap. His plastic panties crinkled against the soft fabric of her skirt as she lifted her hand to spank him seven times on his plastic panties and diaper. “Next time, the diaper comes off; the next time after that an instrument will be used, and each time after that it will  increase and gain and again.” she warned.

 

Sylvia told the baby to get up and assisted him in climbing into his crib. She smiled at him as she locked the door behind him. “No story tonight, you disobeyed Nanny” she said, as she blew him a kiss and walked out.

 

…to be continued…

 

Scarlet

1.888.430.2010

Sissy Milking Cont’d

September 20, 2013

Previously

Immediately I ordered her to “Take your sissy dripping and use it as lipstick, bitch. I want your lips glistening with pre-cum. Do it now!” As humiliating as it was, she had no other choice but to obey…

 scarlet bed 1.888.430.2010

The story continues…

“Now, do you want to suck cock or get fucked by one, today?” I asked my sissy bitch-dog Buffy.

She seemed frozen with panic as she whimpered back to me, “Mistress, I am not gay. I don’t want either.”

I then informed my sissy that I didn’t care, and if she wanted to squirt, she would have to fantasize about one or the other. Of course I gave her the option of remaining in chastity for another week, but her being in “heat”, that wasn’t a viable option.

So, I asked her again in that calm and teasing voice that I have, but still never leaving my authority in question, “What will it be sissy? Do you want a cock in your mouth or your pussy?”

Being the bitch in heat and wanting release, she mumbled, ‘Mouth, Mistress’.

“You want to be a cocksucker?” I laughed. “Then, say it slut”.

 Trembling with shame, my bitch dog repeated the words, “I want to be a cocksucker, Mistress.”  The realization of how low my sissy had gone just to squirt her sissy juice was made crystal clear. Even with such humiliation and shame, her little dicklet got harder

“Louder, slut.”

I want to be a cocksucker, Mistress.’

“I said louder, slut.”

I want to be a cocksucker, Mistress.’

“I can’t hear you.”

I WANT TO BE A COCKSUCKER!

“Again.”

I WANT TO BE A COCKSUCKER!

“Stop milking your clitty and put your thumb in your mouth, sissy. Suck it!” I giggled at her, daring her to defy me. I informed her that “Since this is your first cock, I am starting with a small penis, but soon you are going to learn to suck a real man’s cock, whore.” I couldn’t help but laugh as she sucked and slurped her pre-cum soaked thumb.

“You like sucking cock, don’t you, bitch?”

 ’Yes, Mistress.’

 “Say it. Say, you love sucking cock.”

I love sucking cock, Mistress,’ she said while still licking and sucking her thumb.

“Keep sucking, sissy. Take your other hand and stroke your clitty dick. I want you to cum with that tiny thumb penis in your mouth, slut!”

It only took my sissy slut a couple of strokes to squirt her sissy milk as she was ordered. I made her go to bed with her lips glistening with pre-cum, her clitty stick wet and sticky with her sissy cream, and her thumb still in her mouth, ashamed at the realization at how much she loved her sissy milking.

Lady Scarlet

1.888.430.2010

sissy spring

April 9, 2010

bandagedress

Now that it is getting warmer I am thinking of all the pretty dresses and things the sissies can be wearing. I have fallen in love with these bandage dresses (like in the picture). They would be cute and tight but with a diaper bulge, perfect. Do you like sun dresses and sheer legs for spring and summer? I’ve imagined having a sissy retreat where the mommies I know help me feminize boys who need to be more like sissies. Wouldn’t that be the most fun sort of retreat?

Mommy Scarlet


diapers and discipline

March 10, 2010

diaper-punishment

Isn’t this the cutest picture? A naughty little sissy called me and had already soaked her bedtime diapers before she had made it to bed. After going over the different implements we had to work with I decided to warm her up with a hairbrush spanking but then move to this Attitude Adjuster paddle. It’s not everyday a naughty little one knows they will need an adjustment and therefore have a paddle just for that occasion. I made her keep the soaked diaper on but add boosters inside of it and another outer diaper. I checked my e-mail the next day and found this picture that I requested and the scan of her hand written line writing assignment. The little one even gave me advice on how to make paddled bottoms sting longer. I was very happy to have heard from her and to help her too.

Mommy Scarlet
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adult cloth diaper pins

February 26, 2010

chocolatediaperpins

Look what Mommy found? It’s diaper pins that baby can touch. Baby can even put these chocolate diaper pins in their mouth. They have such cute things you can make for baby showers. I have some candy molds for these kinds of candies; maybe Mommy will make you some. Then when your face is all sticky and messy Mommy will get such a cute picture of you. Will you smile big with a chocolate covered face for Mommy? I bet your as sweet as the chocolate.

Mommy Scarlet
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a day for sissies

February 19, 2010

I found a store on Café Press that is for Sissy Pride Day 2009. It fell on February 4, 2009. I couldn’t find anything about a Sissy Pride Day 2010. Café press is a place where anyone can sign up and design T-Shirts, mugs, totes, and sweatshirts. So I wonder if there is an inside story to this with the person or people who created the store.
It made me think though. Having a sissy day would be pretty nice. There are sites about gay pride days but we all know that gay and sissy are not synonymous. Now it has me thinking what would Sissy Day be like? One sissy I spoke to said a day in spring would be a good time for it. Another offered that Sissies should wear something on the outside of their clothing to signify they were celebrating, even if it were something subtle. I would hope there would be a good amount of participation for a day all for sissies.

Mommy Scarlet
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switches for you

December 9, 2009

reasonsantasnaughtylist

You told me you were good, and then I saw “the list” your name was right near the top. I couldn’t believe it. So now that you have lied and been super naughty what will Mommy do with you? Don’t expect too many toys in that stocking of yours. My opinion is that Santa will bring you switches. Then I’ll know just how bad you are. There won’t be anything to lie about when Mommy bends you over and gets the switches out.

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all the girls

August 20, 2009

It’s no big secret that I am a sissy-a-holic. If there were such a thing anyway that would be me. You know what else I like? I adore girls who were once all boys, as in ones who have gone for gender reassignment. I’m not talking about roleplay or magic or fantasy, I am talking about actual real life stuff. I don’t think the transformation is for everyone. For those that seriously feel they were born the wrong gender though I think it is wonderful when they have a support system and can make the transformation. If you happen to be in that situation and also love abdl and Mommies, know that we love special little girls like you. It’s hard to find the right words to use, because everyone has their own preferences on what they want to be called. I think girls or women sums it up though.

Mommy Scarlet
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can you hold it?

August 6, 2009

I can think of bunches and bunches of situations that would get you put back into diapers. One I was thinking of involved setting someone up. Mommy fixes you a tall cup of juice right before getting in the car. Usually I take you to the bathroom before we go, but things are rushed this time. You say a little ways down the road that you have to stop, but I keep driving. It would be the perfect situation for you to lose control when Mommy hits a few bumps in the road.

Then with your pants wet and your face red I would march you into the store and talk to you loud enough for everyone to hear. What a big baby you were to wet your pants on such a short car trip. For some that would be too much, but I know many of you would get such a rush for Mommy treating you that way.

Mommy Scarlet
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