Crystal's StorySite


Sissy Rita

by Caroline Richards

Part 2


Mistress Sandra put the leash and collar back onto the sissified boy and led him back through the corridors of the Institute to the dormitory where Mistress Gillian was waiting for him. As he entered Her presence he cast his eyes downwards and curtseyed as required. It was a very deep curtsey and he could feel the leather corset gripping him tightly and making sure his back remained perfectly straight throughout.

"Thank you Mistress Sandra. My, our darling boy does look really good doesn't he? Such a pretty sissy in his white virginal clothes and makeup. I just love the satin bow in his hair Mistress and I am sure he will do well at review in a few moments time. Come with me darling but first you must thank Mistress Sandra."

He turned to face Mistress Sandra and again he curtseyed deeply while saying, "Thank you so much Mistress Sandra for making me look like a pretty sissy today."

"You are welcome dear. I hope to see you again soon", and She gave him a small kiss on his pink glossy lips. At this he could feel himself becoming erect again inside the lacy petticoats, but the skirt and petticoats were too full for it to be obvious.

Mistress Gillian took the leash and he followed Her towards the front of the Institute and the Office of the Head Mistress. Mistress Gillian knocked on the door and entered with Sissy Rita following at the required respectful distance. Without looking up he curtseyed and waited to see if he was to be allowed to speak.

The Head Mistress got up from behind Her desk and walked towards him. She was a tall woman, and the 4" high heeled boots meant that She towered over Sissy Rita. She was dressed in a full leather outfit, as were all Mistresses, and although She must have been in Her mid 40's She was still a good looking woman and a very powerful personality.

"Look at me Sissy", She said as She lifted his chin with Her hand. She examined his makeup and dress closely and was obviously very pleased with what She saw. "He has come a long way in 6 months Mistress Gillian. He is a real credit to you I really value the work that you do here and so does the Board of Management. Keep this up and you could well head an Institute very soon."

"Now Sissy. Tell me how you feel right now."

"Yes Mistress. I feel humble and lucky to be with You. I feel very feminine even though I may have much more to learn. I feel very sexy Mistress", he said blushing furiously as he did so.

He had been taught to be totally honest about his feelings and so his words were sincere and both of the Mistresses in the room were aware that he was being open and honest with them. They knew sissies very well, and had no trouble telling when they were not being honest about their feelings.

"Good sissy. Thank you Mistress Gillian, I will call you when the review is finished."

Mistress Gillian turned to leave the room and the sissy curtseyed as She left he knew his place it seemed thought the Head Mistress.

Over the next hour the Head Mistress questioned him about his reaction to his training and how he felt about becoming a sissy. She made him walk around the room for Her, stand in front of the large mirror on one wall and touch up his makeup, curtsey and thank Her for every compliment about his appearance. More importantly She asked him to tell her how much of a sissy did he feel right now.

His answer was interesting because it showed the Head Mistress that, as far as he had come, he still had a long way to go. But he would only hear that towards the end of the review.

Near the end of the interview another sissy entered with a tray of tea and biscuits and left it on the table just inside the door.

"I will want you to serve tea to me and my guest in a moment Sissy. You will do it well or you will be severely punished, although I suspect that you already know that", She said smiling.

Sissy soon discovered that the guest was his Mother. Despite his shock at seeing Her come through the door, he managed to curtsey as She entered and sat down next to the Head Mistress.

"Hello dear. How are you? I see that you are coming along nicely." His Mother had seen the whole review from behind the large one-way mirror. "I just knew that this would be good for you and you are such a pretty sissy."

"I am well thank you Mother", was all he could manage in response. He had not seen his Mother since the first day and he was shocked, but also hopeful that She would now take him home.

"Well that is good dear. I have had a long talk to Mistress before your review and the review has just confirmed what we both thought. You are not yet the sissy that I want you to be, so I have agreed that you will remain here for at least another year. I want you to be the best sissy in the neighbourhood when I do allow you to come home."

Sissy Rita was devastated and a few tears gathered in his eyes and trickled down his cheeks. His Mother saw this and got up to dry his tears with Her handkerchief, dabbing them gently so as not to ruin his impeccable makeup. "Don't be sad dear. I still love you really, but this is important to me and you will do your best for me from here on as I see you have already been doing. Won't you?"

"Yes Mother I will."

"Good Sissy. Now lift up your skirt and pettis, I have something for you to put on."

He did as he was told and he stood with his penis growing erect as both his Mother and the Head Mistress stood in front of him. His mother took a small stainless steel ring from Her bag and showed it to him. It was inscribed with the words Sissy Rita. She undid the clasp and then placed it around his scrotum, using the screw mechanism to tighten it sufficiently so that it could not be removed. A small drop of super glue in the mechanism meant that it would have to be cut off at some time if, of course, it was ever to be removed. His mother also had brought him a new pair of white high cut silk panties with his name, Sissy Rita, embroidered on the front and on the back of them.

'Here darling. Let me slip these on you. I want my boy to be properly dressed for the rest of the day. He stepped into them and he felt his Mother's hands touch him gently as She smoothed them into place and told him to drop his pettis and skirt and smooth them into place.

He curtseyed at the finish and said "Thank You for the gifts Mother. I am so pleased with them."

At that She kissed him on the check and gave him a hug before departing and leaving him alone with the Head Mistress. Mistress Gillian came to get him soon after, and he was with Her for the rest of the afternoon. She took him for a walk, on the leash of course, through the gardens and told him about the remainder of his training would proceed.

At night he was back in the cage, in his nappies, plastic panties and baby doll outfit and chained and cuffed as usual. What would tomorrow hold? Indeed, what would the next year hold for him? He was frightened and excited at the same time. As he drifted off to sleep his mind drifted back to the difficult first few weeks at the Institute that was to become his home away from home.


On the day he was left at the Institute by his Mother he was very, very angry and very upset. When his Mother left, Mistress Gillian immediately put shackles on his legs and a broad steel collar around his neck with the name Sissy Rita engraved upon it. His arms were cuffed behind his back and, because he kept talking after being told to stop, he was hooded and gagged. Totally helpless, the potential sissy was taken down into the bowels of the Institute and into the dungeons, which is where he first met Mistress Jennifer.

He was kept in the dungeon for over a week and his routine consisted of little more than sleeping or being punished and humiliated. Most sissies were like this at the outset, so this sort of treatment was given to many of those who were new to the place.

He had a cage on his own, was fed from a bowl and made to eat from it like a dog, and Mistress Jennifer strapped him regularly until he cried and begged Her to stop.

"So will you finally begin to do as you are told boy? Do you realise that your future is in my hands and you could potentially never get out of this dungeon if you do not begin to accept your fate?"

It was about the eighth day when he finally submitted. He was too sore and tired to do anything else.

"Yes Mistress. I will be obedient from now on. Please do not beat me anymore. Please let me learn to be a good sissy."

Mistress Gillian then came to collect him and he moved into the dormitory under Her direct supervision. Mistress Gillian was about 30 years of age and She had a lot of experience in training new sissies having been at the Institute for almost ten years. She loved Her work and was usually stern but fair with those in Her charge. She had three other sissies in the dorm, all of who were older than Sissy Rita and had been there for some months already.

Sissy Rita soon started to learn about true obedience, about posture and how to greet a Mistress all of the rules that were to govern his behaviour from here on. Mistress Gillian made it clear that he would be back with Mistress Jennifer at the sign of any discontent and so he determined to do the best that he could.

At the end of the first day with Gillian he was exhausted and looking forward to going to bed in his cage. Even so he was taken aback when it became clear what he was expected to wear to bed.

"Up on the changing table darling and let me get these nappies on you."

Mistress Gillian slipped the thick nappy under him and used large safety pins to hold them in place. The soft pink plastic panties came next and his groin stirred as he felt Her warm hands touching the nappy near his private parts. She was very aware of his reaction and began to rub Her hands gently on the nappies, feeling him get hard under Her touch.

"That's a good girl Rita. Enjoy the feeling. We can do this often if you have been a good girl, but you are never allowed to do it for yourself. Now, here, sit up while I put you in your brand new baby doll outfit darling."

He sat up and felt the silky smoothness slide over his skin and he shivered with unanticipated pleasure. His erection grew even further and Mistress Gillian laid him back down on the table and then bent over him, touching his face with Her red lips and moving Her hands over his belly and over the smooth pink plastic panties. She could feel him losing control, and it excited her that She had such power over these boys Her pussy was dripping inside Her leather underwear and She could feel some of Her juices running down Her legs. She felt him cum inside his nappies over and over again and She held him tight as She decided that this could be one of the prettiest sissies She would ever have under Her control. He was so young and therefore so susceptible to the training methods that She would use on him.

"Off the table and kneel in front of me Sissy."

He knew better than to disobey and he was at Her feet very quickly.

'Now, I want you to clean my thighs with your tongue Sissy. Do it quickly but be gentle or I will whip you."

He moved close to Her and, shaking with nervous tension, he licked the sweet fluid from Her legs. The bond between them was incredibly strong from that moment which is exactly how Mistress Gillian wanted it to be. She was an expert at this.

"Now. Into bed with you." She locked him into place, closed the cage and turned off the lights. The new Sissy lay there wide-awake and his mind in turmoil over what has just happened to him. He could feel the cum inside his nappies but he could not touch himself down there. The chains saw to that.


The next morning he was awake early but Mistress Gillian did not come into the dorm for what seemed like hours. By that time he found that he had to pee in his nappies or he would burst and then, to his everlasting shame, he had to poo in them as well and then lie in the mess he had created for at least an hour. He wondered if something in the food he had been given the night before caused him to poo so early and so easily. In the end, he gave up worrying too much about the cause it was the effect that was terrible. He could feel it squelching against his skin.

"I see my new Sissy has wet himself and, from the smell, has soiled his nappies hasn't he", said Mistress Gillian when She came to let him out of the cage later that morning. 'Why did you do that Sissy? Answer me boy."

"I didn't mean too Mistress", stammered the new Sissy. "It just sort of happened to me before I knew it. I am sorry Mistress, I will try not to let it happen again."

"Good answer Sissy. But the truth is it will happen to you often from now on. Sissies are required to wet and soil their nappies from time to time it is designed to become a part of their way of life and your life will be no different. You will never again in the whole of your life go to bed without nappies and plastic panties, and you will never again get up dry and often you will have soiled yourself as well. That is the way it is meant to be and it will most certainly be that way with any sissy that I train. Do you understand?"

"Yes Mistress."

"Good. Perhaps you will be a quick learner after all."

He was then allowed into the bathroom to clean himself up and then, as routine demanded, come out and kneel before his cage awaiting further instruction from the Mistress.

What surprised him was that on the first day he was allowed to wear very little, but that did not mean that the humiliation wasn't intense. Mistress Gillian arranged first for a shoe fitting, and he soon found himself in a pair of black 3" heels that were locked on around his ankles. He stumbled many times during that first day, but gradually he became accustomed to this new way of walking. He was fitted with a plain pair of black panties and a plain black top before Mistress Gillian led him into what appeared to be a medical room of some description. He was weighed and measured from head to toe, to ensure his new outfits would fit him properly. Finally, after being restrained and forced to bend over a bench he felt Mistress Gillian put some sort of cold and slippery gel on his bottom and push some of it inside him with Her gloved fingers.

"Now we will really start your training Sissy Rita. A butt plug should become the joy of every sissy like yourself and you will wear one at all times during the day unless you have special permission to do otherwise. You will learn to fit it yourself in future but, just for my special sissy, I will fit it for you today."

With that he felt pressure on his bottom and his anus gradually opened to receive the intruder. He could not see it, but it felt enormous and it hurt a little at first but Mistress Gillian was gentle and took Her time moving it backwards and forwards until it finally slipped deep inside him with his cheeks closing around the narrower portion near the end. He gasped as it locked inside him and then he felt Mistress Gillian reach around and rub his cock with Her gloved hand. He was erect within seconds and suddenly the plug felt warm and comfortable and in the right place. He knew he could resist the feeling no longer and he began to move with the motion of Mistress Gillian as She stroked his rigid cock.

"My, my what a sexy little sissy we have here."

She leant over his back and stroked him with Her left hand while Her right hand found its way to his mouth. She pushed a finger passed his lips and into his mouth and it was clear he was to suck on it as She stroked him.

"Good boy. Learn to suck quickly. It is a skill all good sissies learn early in their training. Suck on my fingers and move against me as I stroke you to a pleasure greater than you have known before my little one."

She stroked him for what may have seemed like ages but was in fact only a couple of minutes. For the second time in no more than a day he came in great jerks with his seed spurting from him and onto the floor beneath the bench. He moaned with pleasure and felt so grateful to his new Mistress for pleasuring him in this way. He had never in his life felt as good as this before. At least he did before it became clear that he was to clean up the mess on the floor in a very personal way.

"You are to get down on your knees now Sissy, and kiss my feet and thank me properly for allowing you to cum."

He knelt before Her and, despite himself he became hard again. His penis pushed out the front of his black panties as he kissed each of Mistress Gillian's booted feet in turn. This action and the strong smell of leather were to become constant features of his life.

"Now, clean it up with your tongue."

He hesitated. Surely She didn't mean him to lick up his own cum, but he soon found out that was exactly what was required. Her whip cut into him as he hesitated.

"If I have to say it once more you will be back with Mistress Jennifer for a month. Clean up your cum with your mouth now Sissy."

The taste was salty and he hated it, but he did as he was told there was no option open to him. Learning to clean up his own cum in this would also become a feature of his new life.

The final action taken that day was having his hair cut short by the hairdresser located at the Institute. She was really nice, and She explained why it was being cut and how he should begin to look after one of his most important assets from now on. She gave him some special shampoos and conditioners and explained how to get his hair into the condition expected of every sissy.

The end of the day could not come soon enough for him. Exhausted, excited and worried were all emotions he carried with him, as he was nappied and changed and chained into his cage for the night. Mistress had also given him a big rubber dummy to suck on while he went to sleep.

"I want you to have this in your mouth from now on until you go to sleep and you are ensure that you have it back in your mouth as soon as you come awake Sissy."

"Yes Mistress."


Over the next few weeks he fell into a routine of cleaning himself when he got up and ensuring that he had his butt plug in place before putting on his simple clothes and locking his high heels on. His hair shone from the attention that it was getting and he was becoming quite competent in his high heels. To this stage he had seen other sissies, including those in his dorm of course, but he had never been allowed to speak to any of them. He felt isolated and although Mistress Gillian took extra care with him, he was starting to get quite lonely. Even at meal times he was not allowed to talk to the many others in the dining room.

Then one morning after breakfast Mistress Gillian took him to a quiet room still on his leash of course. He knelt before Her and listened carefully as She explained that it was important for new sissies to be inducted the way he had so the Mistresses were sure that they would not be a disruptive influence with others in the midst of their training. From tomorrow he would be fitted with a number of brand new sissy outfits specially prepared for him, and from then on he would join all the regular classes and activities within the Institute. Mistress explained that not only would he need to learn to look like a sissy, but that of course his actions and talents would have to match those expected of all sissies and particularly those laid down in his training program by his Mother.

The next morning he was introduced to the Wardrobe Mistress and he dressed completely as a girl for the first time. Over the preceding weeks great care had been taken to permanently reduce his body hair and he was as 'smooth as a baby' as Mistress Gillian liked to say. The outfit that was to become his favourite, even though he would never admit it, was the first one he put on and it felt wonderful as it touched his smooth skin.

That morning, for the first time in his life, he wore a matching pink and white bra, panties and suspender set. Flesh coloured nylon seamed stockings were attached to the suspenders and Mistress Gillian helped him adjust the clasps so the stockings could not sag. Breast forms filled the bra nicely and he had a wonderful figure after a pink waist cincher was tightly laced around him. A pink satin slip was followed by a lovely satin pink dress with white lace trim. It had short puffy sleeves and a full skirt that flowed around him as he walked. Pink open-toed shoes with 4" heels made him stumble a little at first with the new height. Small gold studs in his now pierced ears, a gold necklace and a gold bracelet on his right wrist completed the ensemble. His makeup was sparing but brought out his eyes and both Mistresses were privately stunned by what they saw before them. He really was beautiful, even though, because of his short hair it was still very obvious that he was a boy.

"Take a look in the mirror honey. Your Mother would be so proud of you if She could see you now."

He looked and could not believe it himself. Richard had long gone and Sissy Rita was alive and well, even if only a novice. Despite his early difficulties in adjusting to his new life, he had to admit that being a sissy had some advantages especially when Mistress Gillian was kind enough to allow him to cum. It was still true, however, that he wished he was still at home and that his Mother had not decided to send him here.

"Now walk around the room for me, curtseying as You come back in front of me. Get used to the new height of your heels because you will be required in the future to wear even higher heels on some special occasions. Start to adore the feel of your slip and dress and stockings as they move against your petty body let yourself go because you will forever more be dressed in clothes like these honey. Show Mistress what a pretty sissy you are and what you can become."

He was a little clumsy at first on his new shoes, but he started to get the hang of it after five minutes or so. His Mistress was very pleased with his progress, and at last She told him to stop before Her while She re-attached his collar and leash and led him out into corridors of the Institute.


He met the three other sissies in his dorm for the first time that night as Mistress Gillian was preparing them all for bed. After they were all in their baby dolls and nappies and plastic panties, Mistress Gillian made them sit together on the floor and hold hands forming a small circle. She told Sissy Rita to say 'hello' and then describe who he was and how he came to be at the Institute.

The three other sissies introduced themselves Sissies Rose, Roberta and Robyn. They were all pretty, but none was as pretty as Rita. Rose and Roberta were in fact soon to graduate and two new sissies would be with them in the next couple of weeks. Sissy Rita was surprised to learn that both of them had been at the Institute for three years. He still hoped he would not be here that long.

"All right girls let's get you all to bed, but to celebrate Sissy Rita's graduation to being allowed to dress fully for the first time I am going to allow Sissy Robyn and Sissy Rita to sleep in the same cot perhaps Robyn you would like to take Sissy Rita to your bed for the evening? Would you like to do that?"

"Yes Mistress Gillian. Thank You', and with that Sissy Robyn took Sissy Rita by the hand and took him across to his bed. Mistress Gillian locked them both in as usual so there was no way they could be really naughty during the night, but She was hoping that the two sissies would become close friends over the next few weeks. In a place like this it was important for new sissies especially to have a friend to help them find their way when the Mistress was doing other things.

When the cages were locked and the lights turned out, Sissy Robyn took Sissy Rita by the hands and pulled him close. Sissy Rita resisted at first, but Robyn was insistent and eventually the two sissies lay side-by-side revelling in the smell and closeness of their respective companion. Robyn had done this before, but for Sissy Rita it was a strange and disturbing experience although eventually he found himself getting erect as the perfume and feel of Robyn's body so close to him made him aroused. When finally Robyn kissed him with lips covered in the soft shade of lipstick that all the sissies were required to wear at night, he succumbed to the feelings sweeping his body. He returned the kiss timidly at first and then with passion as his need for companionship and affection overcame his reticence at being with someone just like himself. Robyn then placed Sissy Rita's dummy in his mouth before putting in his own. They went to sleep in each other's arms, and when they awoke they kissed again. Indeed they were kissing when Sissy Rita peed his nappies for the first time that morning and then pooed himself as he had become used to doing at this hour of the day. Mistress Gillian was pleased to see them together that morning. She knew Sissy Rita would now adjust to the life that was to be his from now on.

"And how are my sweet little girls this morning", She said as She walked in after the cages were opened. "Perhaps you would like to sleep with Sissy Robyn again sometime Rita? Would that be something you would like dear?"

Sissy Rita went red, but eventually in a very shy voice he said, "that would be nice thank you Mistress." The direction of his life had been changing irrevocably over the last few weeks and this admission was another important step for him.




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