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An Appointment for Sissy

by Caroline Richards

 

"I am not a sissy. I won't be dressed as a girl. Go away."

The sissy was chained to his bed as usual when his mother came in to make sure he was awake and thinking about getting ready for his appointment at the Sissyboy Boutique. He was dressed in his pink baby doll nightie and, of course, he was in nappies and plastic panties to prevent the mattress in his cot from getting wet. As usual he was soaked through because he had to drink a large bottle of juice each night after being put to bed, and he had even occasionally soiled his nappies when he was released later than normal.

"Oh dear. Are we going to go through this again? Perhaps I will get Aunty Margaret in to help me get you organized, and you know that she will take none of this nonsense." Margaret was her older sister, and a formidable woman who had initiated the process that lead to Jamie becoming a sissy. At 14 years of age he was uncontrollable but now, only 6 months later, progress had been made despite the usual morning outburst. At 5'9" he was slim and fine featured and he had all the makings of a beauty, if only he would cooperate.

His mother sat on the edge of the cot and put her hands on either side of his face as she drew him towards her. "Perhaps a wake up kiss will settle my little darling down," she said looking directly into his blue eyes that were wet with tears. She ran her tongue over his cheeks collecting his tears, and then kissed him on the mouth in a manner that she knew would both arouse him and make him more compliant. Although she didn't like to admit it to Margaret, it aroused her too. She could see his penis swell inside the nappies, and she put one hand on the outside of the plastic panties to feel it grow further as she touched him. He groaned with pleasure and forgot who and where he was for a moment as he moved against her downward pressure. She felt him release and watched as he closed his eyes and savoured the delicious feeling that all sissies feel when they are allowed to cum.

She sat and stroked his lengthening blonde hair as he settled down and finally used his little sweetly perfumed handkerchief to dry his eyes. Finally his mother kissed him again before taking the key from its hook on the wall and undoing the steel collar locked around his neck and chained to the steel bars of his cot. He was chained this way each night without exception, and he had initially found it hard to sleep comfortably with the collar in place. At first his mother thought it was an unnecessary precaution, but Aunty Margaret had insisted. She had prior experience of a sissy who had tried to escape at night.

"Now. Into the bath, and when I come in I want to see lots of suds and lots of perfumed oil in the water. Your clothes will be on the cot waiting for you, and I think I will get Aunty Margaret to help you with your makeup this morning, because we are to have such a special day my darling." He got into the bath and his mother came in to help him wash, making sure he got into all those nasty cracks and crevices that could hold dirt.

Returning to his cot he looked in dismay at what he was to wear and, despite trying hard not too, he burst into tears again. He seemed to cry a lot more these days for some reason, and he had started to lack the confidence to do things himself, often having to depend on his mother or Aunty to help him dress, do his makeup and even prepare himself for bed each night. He walked down stairs with a towel around his waist to find if his mother was there to help him. However, Aunty Margaret was sitting in the lounge room when he came in and she soon sorted out that he needed help to dress.

"Up the stairs quickly Sissy. We have only an hour before your appointment." As he walked upstairs Aunty walked right behind him, occasionally slapping him on his bare legs with the little whip she always seemed to have with her.

Soon, and without any fuss she had him in his tightest corset, a heavily boned white with purple lace garment that he hated with a passion. "Now bend over and take your plug darling." He obeyed, bending over the changing table and gasping as the horrid thing was inserted deep inside him. He was nearly always plugged this way and he had not yet got used to the feeling of stretching and discomfort that occurred until the plug finally slid inside and locked itself into place. Next came his white lace training bra and matching white panties with a purple ribbon in the front. Long white socks with lace tops and white Mary Janes were next and then a multi layered petticoat under a white long sleeved dress, with purple lace edging, finishing just above his knees.

"Sit down in front of your mirror darling. We need to be quick now, so I will leave your false eyelashes for next time."

Despite himself, he had begun to enjoy having makeup smoothed on to his face. Today his lipstick and eye shadow was mauve and when Aunty put his hair into short pigtails he had to admit he looked really cute, especially when the purple ribbons were tied around each of them. "Move your head from side to side honey. Let me make sure your hair is sitting properly."

"Now, stand up. Turn around for me. Curtsey. Well, what a nice looking Sissy we have today. Come with me."

Aunty Margaret took him by his right hand and led him downstairs where she found Janette was already in the car waiting. She took his white leather baby reins from the hook near the front door and slipped them on, buckling and then locking them in the small of his back, before taking the leash and leading him out to the car and helping him climb into his baby restraint seat in the middle of the back seat. There was a panel on the front of his reins which told the world that he was Sissy Jamie.

Within 30 minutes they were at the front door of the Boutique where the owner, Miss Catherine, was waiting for them. "Hello Janette, Margaret. Here. Give me the leash and I will take him out the back to get started. If I have trouble I will call you. My goodness he is quite pretty isn't he. Well, today will be a true test of his capacity to be a good sissy. Come with me darling." She pulled on the leash and almost dragged the sissy through the boutique while at least a dozen women, all impeccably dressed and most in leather outfits and black high heeled boots, looked at him pass. Each of the women also had a sissy on a leash of some description, and none of them looked any happier than the newly arrived sissy.

"We have ten dresses that you are going to parade for my lady friends darling, but you are to choose them from the selection on these racks and I want you to choose a prettier dress each time. Get to it."

The sissy just stood there not knowing what to do, until Miss Catherine took his leash and pulled him towards her. Looking directly into his eyes she said "Get started sissy. I have a wonderful new little horse whip that I have been waiting to try on a reluctant sissy, and you will be the first to feel it if you don't move now."

He rushed over to the racks and quickly took off a wonderful pink dress that would reach down to his feet. With lace and bows everywhere it was a delight, and as he stepped into it Miss Catherine let his hair out and brushed it to sit around his neck and frame his face prettily. A pink bow, new pink shoes with 3"heels and locking ankle straps were next. With his baby reins removed, Miss Catherine locked a gold plated steel collar around his neck and, after attaching a chain leash, she led him out onto the small stage for exhibition.

The sissy was petrified, but a few short and sharp commands had him walking across the stage following Miss Catherine, and almost hypnotized by the sound of her boot heels on the wooden floor in front of him. He was made to walk backwards and forwards a number of times until Miss Catherine was happy with his walk and his posture. As he left the stage he was told to curtsey and the embarrassed sissy did his best in his constricting corset.

Over the next hour he was to wear nine more dresses, each of them getting progressively shorter and more transparent. The last was really just a white lace short apron covering his underwear, and the women watching were delighted to be able to see his panties, his bra and the hated corset through the lace concoction. For his last parade Miss Catherine also asked his mother to come up on stage and show him off, which she did with great pride. After his last curtsey she kissed him in front of everyone, and of course his erection became obvious to everyone in the room, even more so when his mother touched it through the lace with her fingers with luscious long pink painted nails. She even ran one nail along the length of his penis and he shuddered with excitement despite himself, and a little wet spot appeared where all was dry before. To his shame he even noticed a number of the other sissies looking at him with excitement in their eyes, although their Mistresses were quick to whip any of them who gazed at him for very long.

Finally, it was all over and he was back in the clothes Aunty Margaret had dressed him in before leaving home. Miss Catherine lead him back out into the room on his leash and handed it to his mother after saying, "What a beautiful sissy you have Janette. He is a credit to you and Margaret, but I do think that now you have taken him this far, you should both join our little club. I think he would benefit by being able to socialize with other sissies from time to time, and you of course will learn much from the other Mistresses here. Perhaps both of you would like to come back next week to select some leather outfits and other devices that will be useful in his further training."

Two weeks later the sissy woke up in tears again, distressed at his circumstances. He was wet and this time he had soiled his nappies because it was late in the morning. When his mother came in he noticed that she was, for the very first time, in a back leather full length dress over leather boots with 4"heels. Her hair was swept up into a ponytail and she carried a small whip, just like the one Aunty Margaret had used on him."

"Stop crying Sissy." The whip lashed onto his bare legs before she sat down beside him as she did most mornings now. "I can see we have much more work ahead of us dear haven't we. I think I may have been a bit too lenient in the past. Aunty Margaret and Miss Catherine have convinced me that I need to take a much firmer hand with you." She unlocked the collar. "Now get up, bathe and dress in your maid's uniform. You have a lot of work ahead of you today." And his transformation entered a new and critical phase.

  

  

  

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2006 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.