Crystal's StorySite


Sissy Rita

by Caroline Richards

Part 1


The Sissy could finally hold on no longer and he felt the warm pee flood into his nappy and seep through to touch the inside of his soft pink plastic panties with the beautiful red flowers printed on them. Why he tried to hold on he did not know, because after six months he really knew that it would happen to him every morning. It was just that he was still not fully accepting of his new status in life he supposed. Six months learning to be a good sissy was not really a lot, and in his heart he knew there was so much more to learn.

As he wet himself, he shifted slightly to get more comfortable in his cot. The stainless steel collar attached to the chains that were in turn attached to the steel cuffs around each wrist were something else he had also found it difficult to adjust too. There were three other sissies in cots in the dormitory, all in similar positions, but that didn't make it any easier to accept. The Dormitory Mistress, Mistress Gillian, put each of them in these restraints each night to ensure that no sissy was able to satisfy his urge to satisfy himself sexually. No sissy was allowed to cum without permission and certainly not allowed to masturbate himself at any time. The collar also had an extra chain locked to a bar of the cage that was also his cot, so that even when Mistress Gillian opened the cage electronically, no sissy could get up until She decided.

He was just settling again, when he heard the door to the dormitory open and Mistress Gillian's high heeled black leather boots beat on the floorboards as She walked over to him after pressing the switch to open each cage. As She stood next to him he simply looked up at Her until She spoke to him. He knew that to speak first would bring him a very severe punishment.

"Good morning Sissy Rita. How is my youngest sissy today?"

"I am very well thank You Mistress Gillian. It is so good to see You again."

This was the required standard greeting which he had finally learned to adhere to after a very severe spanking at the hands of the Mistress in charge of all disciplinary matters Mistress Jennifer.

It was true that he was the youngest sissy in the dormitory, although not in the Institute as a whole. He came here on his 14th birthday, which was the earliest time allowed by law.


"I don't want to go there Mummy. It is not fair. Please, please do not make me go there. None of my friends have had to go and they are allowed to live their lives as boys."

He found out the day before his 14th birthday that he was to be taken to the Institute the next day. Certainly he had sometimes been naughty, but what boy wasn't and it seemed so unfair. His father obviously didn't agree with the decision taken by his Mother but there was nothing that he could do about it. The law made it clear that a Mother could commit Her son or sons to the Sissy Institute at any time after the age of 14 years. Things had changed in the last 10 to 20 years and not as many boys were being trained a sissies any more, but it was still an option used by many mothers at their absolute discretion, and his Mother had enrolled him many weeks ago without his knowledge.

The Institute catered for well over 100 boys, and it was just one of many in the country, although the numbers had reduced somewhat in line with changing community attitudes. The President, and the government as a whole, knew that they needed to be careful about balancing the needs for control of the male population with those of economic growth, and She was nothing if not one of the best Presidents the country had ever had. The all-female government was also well aware of the direction that had to be pursued although there were always those who thought that much stricter control of the male population was required.

The Institute was on the edge of town and in spacious grounds that were well secured. It didn't look like a prison, but that is what it was in reality. Once inside no sissy or potential sissy had ever managed to escape.

He well remembered his Mother walking him in through the front door and into the Head Mistress's Office where he stood at Her side while his future program was outlined. He would be here it seemed for at least a year, with a review of progress at 6 months. He also knew that if needed he would be here much longer than a year. The government paid for all training up to a maximum of three years after which the Mothers had to pay if further training was required. The truth is that three years was usually more than enough to full train most sissies, especially if they were enrolled at an early age as Richard, or Sissy Rita, had been.

After an hour his Mother had left and he had not seen Her since. Mistress Gillian came in to collect him and his training began immediately.


Mistress Gillian unlocked the collar and other chains and Sissy Rita got up and went into the bathroom to prepare for the day. It was review day and he had no idea what would happen at this stage.

When he came back into the room, naked and clean, inside and out, he knelt down beside his cage and waited for Mistress Gillian to return for him. She soon came over and locked him into his usual collar and leash and led him out of the dormitory to the dressing room where the girls would be ready for him.

"You are aware today is a big day for Sissy Rita. Please do a good job for him girls."

"Of course we will Mistress come over here darling and let's get you started."

The outfit he was to wear today was a special one he had been told and so it proved to be. Mistress Sandra first put him into a white leather corset which She laced very tightly before also putting him into a white lacy bra with breast inserts, a white suspender belt, white seamed stockings and white shoes with 3"chunky heels and ankle straps. The bra and suspender belt had pink ribbons around the edges and the shoes had a pretty pink bow attached to the outside of each ankle strap. Finally She locked a broad white leather collar with a gold buckle in the front around his sissy neck.

"The panties and your dress will come after we have done your makeup honey, so bend over so we can get you properly lubricated before we start."

She smeared the lubricant on him and then helped him into the makeup chair which had a rubber moulded seat designed specifically for this sissy. With Mistress Sandra's help he eased himself down into the seat and felt the 6" long dildo touch his anus and then begin to push deep inside him as he slowly settled into the chair. He always felt ashamed when this occurred but every sissy was treated in the same way, and the Mistresses all knew that he would begin to love the feel of something filling his bottom. He regularly wore a butt plug of course, but somehow being treated like this while he was made up to look as pretty as possible was very different from wearing a plug during the course of his normal training.

"Settled honey? I bet that it feels good to be filled like that. Tell Mistress how you feel darling."

"I feel really good thank You Mistress', he said without hesitation because to do otherwise would simply invite an extra punishment session.

"My, what a good sissy you are becoming. Now let's get some makeup on You so that you look sweet for your review."

Mistress Sandra worked quickly on his hair first it was still quite short so it was just a simple brush and the attachment of a huge pink satin bow on the top of his head to get started. His hair was starting to grow out a bit after being cut really short when he first arrived. It was normal practice to do this for all new sissies because it made them very aware of their boyishness in the first instance, and it also allowed the Mistresses to get each sissies hair into good condition and start to style it as they wished. He now used shampoo and a sweetly fragrant conditioner everyday and his hair, although still relatively short, glowed with health and colour.

Next She applied the foundation, some blush on his cheeks, mauve eye shadow, mascara and then a full gloss long life pink lippy, as She called it. He already had long nails they had not been cut since he arrived, and Mistress reapplied a hot pink polish to them. His nails were in good condition and he had now been taught how to look after them properly.

She sprayed some perfume on him as She helped him ease out of the seat and told him to remain standing while She got out his petticoats and dress.

The petticoat was made of white lace and had at least three layers he put his hand on the Mistress's shoulder to help himself balance as he stepped into it and pulled it up to settle around his waist. Next was a white pleated skirt, again with pink trim around the bottom, which Mistress Sandra fastened around his waist. The lacy petticoat made the skirt sit out nicely from his body and the sissy shivered with delight, despite himself, as he felt the petticoat rustle against his stockinged legs. The final garment was a white and pink trimmed short-sleeved cashmere sweater. It was a close fit and his false breasts were very prominent above his tightly corseted waist. Pink dangly earrings and a simple gold bracelet on each wrist competed the outfit. He felt more like a sissy than ever before, and he became erect inside his pettis Mistress had deliberately not put any panties on him at this stage. If he was lucky, that would occur later that day.

"Now, I want you to walk around the room for me Sissy, left hand on your hip as you have been taught, right arm at your side and bent at 90 degrees, hand loose."

"Yes Mistress"

Sissy Rita walked as he had been taught over the last six months small mincing steps that made sure his arse swayed with each step. He was quite adept at walking in high heels now because that is all he had worn since his first day at the Institute.

"Very good Sissy. You are really coming on and you look so pretty today. Now, come with me darling. Let's find out what your future holds."




2004 by Caroline Richards. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.