She Found A Sissy PART 2

She Found A Sissy PART 2

By: Donna Sash

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\[BI\] \[TG\] \[TESTICLES\] \[prequel to the castration story\]

“You will spend the night here. Tomorrow we will go to your place after I come home from work and you will show me every thing. Tonight you will see where you will spend all of your nights here in my house. You will remember, it is My House. You will be a servant here. You will be my lover here, but it is My House, and all the things here belong to me. Every thing you see is mine, and so are you my dear, from now on you are mine, my sissy, to do with as I please.”She took his hand and led him to a door.“This is the sissy bedroom. This is where you will be when you don’t have any duties to perform, or training is over. You will not think of this as your room. This is my sissy room. Do you understand?”“Yes Mam.”

She opened the door and clicked on the light. He looked in and saw a room any little girl would be pleased to have. The color pink was to be seen all over. From the walls to the rug, the canopy on the bed, to the scarf on the table light, each was in its own shade of pink. The furniture was in antique white. On the bed was a coverlet of soft off white with small pink roses on it. The room spelled out feminine charm. No one would think of this as a boys or man’s room. This was the room of a girl; only he knew this was the sissy room. The room he would occupy, but it would never be his. Actually he was starting to wonder if anything would ever be his again. She had stated that he was hers.

“Take off your skirt and blouse and hang then in the closet. Now take off your camisole and slip and fold them and put them in the hamper.”He did so and stood there in his bra, panties, stockings, and corset.

She took down the bed cover and had him lie down.“As I told you your sexuality in now mine to control. You will not masturbate with out my permission. This will be very hard for you to comply with, especially tonight after all your stimulation.”She pulled from under the cover a restraint that was hidden there and cuffed his ankle, went to the other side of the bed and did the same to his other. From under the bed she took another restraint and cuffed his right wrist over his head tightly, and then the left.He was stretched on the bed and couldn’t turn or move.“This is how you will have to learn to sleep. I just love having control of a sissy, and you look so cute there.”

She lowered his panties and started to stroke him. She worked his sissy cock till she could see the strain on his face then she pulled up the panties and kissed him on the fore head.“Good Night my sissy, sleep well.”She turned off the light and closed the door. He heard the lock in the door click closed.

He was frustrated. Sure she had masturbated him before and he had relief then, but now he was at the peak of sexual tension. His first evening in her presence was more than he could fathom. He did things he never dreamed of. Being turned into this girlish sissy by this woman he just met. In addition, licking her, his head spun It took a long time for him to fall asleep.For her part she cold not have been happier. This new sissy would turn out to be the blessing she had needed for a long time. She needed this from the time her husband had passed. She now knew this was what she needed. She was going to have a lot of fun. Her sissy would have fun too, but for him things would start tomorrow. Tonight she had played with him and used him, but in the morning she would really start his training.

He awoke to the sound of the door opening. When she came into view she was wearing a dressing robe. She sat at the side of the bed where he was restrained and asked, “Did you sleep well?” “Yes Mam.” She lowered his panties. His erection grew to its fullest. “This is a problem with all sissies. In their panties are cocks. A sissy’s cock is where all his attention is centered. See how just a touch brings it to attention. The first rule I am going to give to you is that: A sissy may never have an organism with out permission.

I don’t matter how; you may never cum with out my telling you it is all right. Your hand, my hand, by another woman or man, I don’t care. If you cum with out my permission you will be punished. Do you understand?”

“Yes, Mam.”

“Now I know that this would be a very hard rule to keep, especially as you are very new to sissy rules. You have never had to practice restraint of your sexuality so I am going to help you. Unauthorized masturbation will be punished too so I have this for you.”

In her hand was something made out of pink plastic? He did not know what it was, but he was worried.

“This is called: The Chastity Belt 2000. It was designed for wives who had unfaithful husbands. When it first came out it was in clear plastic. The good people at CB2000 realized that others could and would need one and they made this one in pink for sissies. You are going to learn about a lot of devices that I have for a sissy. Your night time restraint was the first and now a chastity device.”

She placed it on his tummy.

“From the look of your sissy cock, I could never get it on to you. I will have to do something about this hard on. Lets see, I could jerk it off. No, if I give you an orgasm like most males, sissy or not, you get lazy after cumming. I could slap it till it got soft, but that is punishment and discipline. You haven’t done any thing wrong. Getting hard isn’t something a sissy can control, not when his mistress has it in hand anyway.

Ah! I have an idea. She pulled a bag of ice from the bag she had with her when she entered. She placed it on his sissy cock and balls. He jumped when the coldness hit him. It just got colder and colder.

“Please! Please take it off.” He pleaded.

“See only one night here and you are learning some sissy things. All sissies beg. What you have to learn is that begging isn’t always welcome, and you really should really only beg for something that you really want. This is just a little cold.”

She put her hand under the bag of ice and felt his cock shrinking.

“It will not be long and we can put your CB2000 on.”

He felt like shivering. It was getting so cold it felt almost like it was burning him.

She smiled at his dilemma. She knew he wanted to plead for her to take the ice off of him, but he responded to her first training by keeping quiet and enduring it.

She took the ice bag away and started to put on the restraining ring on his cock and balls. She had picked the smallest ring in the kit. She then put the cage over his cock and snapped the plastic lock in place.

“There all safe and sound. Now you won’t have to worry about being punished for masturbation. You will still be responsible for orgasm control though.”

She took off his restraints and told him to shower and call her when he was done.

During the shower he felt his new chastity device. He had not realized when he accepted becoming her sissy that things would go this far or this fast. He tried to touch himself and found that he could not get any stimulation. When he finished, he went to her room and knocked softly.

Your ready, good, lets go to the sissy room. She dressed him in his first day’s sissy maid uniform. It consisted of a corset, bra, panties of course, nylons, high heels, a camisole, a few crinolines to puff out the skirt of his pale pink maids dress. It was a one-piece dress that zipped in the back. With the petticoats it was stretched out very far from his legs. She tied a shear lace trimmed apron on him. She did a light make up job on his face and tied a scarf on his head peasant style.

“Your duties for today are to clean the kitchen from the ceiling to the floor. You don’t have to do the inside of the cabinets but I do want polish on the outside doors. I expect the floor to shine. You will find everything you need under the sink. Any questions?”

“Yes, Maam, where do I find the mop and bucket?”

“You don’t. I told you every thing you need will be found under the sink. You have earned your self a discipline. I will only tolerate smart questions. I already answered that one. You will learn my dear.” She said as she held his chin in her hand.

“Oh rule #2: Do not enter any room except for the ones you already have. I have locked all the doors to other rooms and I do not want you to try to get into any of them. Each has some kind of surprise for you and I don’t want you to find out too soon just what pleasures we will be having in them. Good Day, my sissy, work hard.”

With that she left.

He opened the door under the sink and found a tiny scrub bucket and brush. There was no folding mop or anything like that. He now knew that he would have to do all the work the hard way, including washing and waxing the floor by hand. He worked hard all day and by the end of it he was hungry and thirsty. He then wondered, he didn’t have permission to have any thing. He was all ready learning that he would need her permission for just about anything, so he went hungry. He did have water though, through out the day. When he thought he had done enough and the room really sparkled he went back to the sissy room to rest and wait.

When she entered the house she went right to the kitchen and was pleased. He had done a good job. She then went to the sissy room and entered. He was asleep on the bed. She thought I would teach him about laziness tonight. She went to her room and put on another outfit that would remind him of a schoolteacher, short dark blue skirt and off white blouse, a scarf tied around her neck, her hair up in a bun, and she was ready.

She entered the sissy room again and yelled, “Get up you lazy sissy!”

He came alert.

“Who gave you permission to take a nap?” She asked.

“You did not tell me what I was to do after finishing, and I was very tired.”

“I will give you tired. Take off that dress and your petticoats.”

He did so. He was then standing before her in his lingerie.

“Follow me.”

They went down the hall. She took some keys and opened the door. When they entered he saw a large block of wood on a stand. There were cabinets on all the walls. She took him to the block and told him to place himself over it. When he did he found that his rump was higher than his head. She took a restraint and attached it to the leg of the block and his wrist, then did the other. From the bottom of the block she took a wide belt and placed it around his waist, which bound him to the block. At this point the only thing he could move would be his leg. She lowered his panties and left them only on one leg. She then restrained his legs, keeping then open to the legs of the bloc.

“This is my punishment room. If you only earned a spanking, by not doing anything other than that silly question this morning, but by sleeping in your bed with out permission you will gat a strapping for your first discipline.”

He was really worried now. Of course mommy had spanked him. Mommy had placed him over her lap and pulled down his panties and gave him some spanks, but it wasn’t hard and didn’t cause him that much pain. That was the only real discipline he had ever had. This! This seemed off the scale in his mind. Bound to a wooden block?

“This is a tawse. I think you will find that it gets attention really quick. I am going to go easy on you because this is your first discipline and I am only going to give you 5 of the best.”

Smack!

He could not believe the instant pain that came across his ass.

“Owwwww!” he yelled.

Smack! It came down again. Smack!

“Oh Please! It hurts so much Please stop.’

You only have 2 more to go.

Smack!

Whack! The final blow had fallen.

“There now that wasn’t too bad, was it? It was jut to get your attention and let you know right here in the beginning that you are responsible for the decisions you make. Now this is how it ends, when I let you up you go to your knees, kiss my panties, and thank me for your punishment. Do you understand?”

“Yes, Mam.”

She released him from the spanking block; he knelt and kissed her panties.

“Thank you, Mam. I am in need of your correction and need your punishment to make me a better sissy.”

Now go and shower, I will be up to dress you for our trip to your former home.

She entered the bathroom as he was drying himself. She sat him down at the vanity naked. She started to work on his hair doing it in a mock male do. She put a very light coat of make up on his face in very neutral colors, so it would be hard to see that it was on. She then led him to the sissy room and dressed him in an androgynous look. He had on women’s pants with a zipper on the side. It was a man’s cut shirt but in a pale yellow. His lingerie consisted of panties a garter belt holding up dark stockings and a camisole. She tied a small square neckerchief on his neck.

When he looked at himself in the mirror he saw a very feminine looking sissy. He didn’t think it was as androgynous a look; it was very much more a sissy. Nevertheless, that was what he was now. His new Mistress was making it clear that his former life was over and she was making him a new in an image that she, and only she wanted.

She gave him a pair of penny loafers and they even had pennies in them. As he put them on, he could see the stockings at his ankles.

She then handed him a sweater that matched his blouse and in her other hand was a purse.

“You must always carry a purse when you go out. Women keep things they need in them and a sissy will need it even more. I have put some cosmetics in here. There is also a tampon, a panty liner, and a full size maxi pad. I have changed your wallet. She took a long pink woman’s wallet from the purse and showed him that there was a $20 bill and his driver’s license in it. As time goes by we will be filling the picture section, in fact, I want to take your picture right now and put in one.”

He stood there as she took a few pictures. She tied a scarf to the strap of his purse. It had a pink border and multi color flowers in the middle on a white background. Anyone who saw it would know it was a woman’s scarf.

She re did the pictures and told him to wait by the door. She came back and put two pictures of him back to back, in his wallet. When he looked he knew he was looking at a “real Sissy”.

They got into her car and he gave her the address to his former apartment. They entered it and she asked him to get some garbage bags. She told him to put all his men’s clothing into the bags. He filled five of them.

While he was doing this she started going through his drawers. She found all his feminine underwear and put it on the bed. From the closet she placed all his woman’s shoes on the bed also. Looking through the clothing on the hangers she picked all his skirts and shirts that had a fem look. She asked him if there was anything else that belonged in the feminine pile and he brought out his own scarf collection. Thee were about 20 scarves in multi colors and she was pleased with the selection. They went through all of his other possessions and after she had everything she wanted, she told him he would not need anything else from here, and that the only thing he needed to do was to take his former men’s clothing and place them in the garbage bin.

“You won’t be needing them any more and I want it to be by your own hand that you throw your old life away.”

She had him put everything else in the trunk of her car. She took the keys and asked which apartment was the owner or maintenance man. She knocked on the door of the owner’s apartment. When he opened the door she said, “I am returning the keys to Bobbie’s apartment”.

The owner looked past Ms. Watson and saw his tenant Robert Wise. Of course Robert didn’t look anything like the boy that had rented the apartment from him. What he saw shocked him. She knew why this woman called him Bobbie. What he saw was a feminized boy, a sissy.

“You may give what is left in his apartment to any homeless organization that you feel like, Bobbie will not be needing them anymore. If there is anything left of his security rent, you may also give that to the poor.”

With that she turned and said, “Come on Bobbie, dear, we have lots to do.”

The apartment owner really didn’t know what to think as this woman took his former resident by the arm, he saw the scarf in the breeze as the went around the corner.

He was humiliated. It wasn’t often that he saw someone he knew when he was in his own feminine clothes, but tonight this person he had known for almost a year saw him as a sissy. He was blushing as he entered her car.

“You know, it’s still very early. I’m not ready to go home just yet. I’ve been looking at your ears and I know that you need something. I think its time to buy you a small present for the beginning of your new life, kind of a celebration.”

Now what he wondered? What was she up to? Then he started to worry again. Ms. Watson as he had just found out her name was pulling into the mall. She found a parking lot.

“Come on Bobbie, let’s find something for you.

The entered the mall and he was again blushing. Never in all his time dressing had he gone public with his femininity on show like this. He was very conscious of his purse and scarf, the way he looked, and the makeup. He was embarrassed at the way he was dressed. Of course that was just what she wanted. She wanted him to feel really out of place.

As they were walking down the hall she stopped at the Piercing Pagoda.

“What you really need is earrings. No sissy should be without earrings. Oh Miss!” she called out. “I would like to have his ears pierced.”

The sales girl came over to them. “Hello, I can do a piercing right now if you like.”

“I think that maybe 3 holes in each ear would be a good start for tonight. Can you show me the most sissy starters you have”?

The girl smiled, “ I have just the thing. We just got some posts in pink ice. I think a sissy should have something pink in his ears for the first time.” She said getting into the part. She had a few women bring in their men in the past. Most had just one hole in their left ear, but a few women like this one wanted to make their boys into sissies. She knew the score and if she wanted repeat business she would play the part.

“Hi she said, what’s your name.”

“My name is Bobbie.”

“I want you to sit here on this stool.” She took her pen and marked his ears each in 3 places.

“This is going to pinch you a bit as the earring goes into your ear. You won’t cry will you? I have had some other sweet boys here in this chair and they did cry.

However, you are a good boy aren’t you? You won’t be crying here tonight.”

She put the first pink stone post in the gun and set it to his ear.

“Ready, honey? Here goes.”

She put in the first of the six posts in. She held his face, looked at the both of his ears, and was ready to put in the second.

“I love your make up dear, it isn’t too over stated.”

Snap the next one went in. For her part his mistress was having the time of her life having this girl humiliate her new sissy.

“The sales girl looked at his mistress and said”, I think I have some blusher to use on him. His cheeks are red now and I think if I put some on him, I could get it right in his very own natural place.”

“That would be so kind of you. He hasn’t had anyone do his makeup except for me. He is a new sissy and has a lot of new experiences left.”

The sales girl took a compact from her purse. Rubbing the brush in the blush, she looked at him again and worked it into his cheek.

“There you are. That looks much better, and now others will be able to see your makeup better.

“Thank you.”

The sales girl finished his last piercing. He got up from the stool.

“Bobbie, I think you should thank her properly, I don’t think you can kiss her panties right here in the mall, but a kiss on the cheek would be alright.”

He kissed her on the cheek and Ms. Watson paid her.

“Bobbie, when ever you give someone a kiss you must repair your lipstick.”

Very humiliated once again he took the lipstick from his purse and applied a new layer.

They said good by and headed for the exit.

“You did very well in there Bobbie. You will just love it as time goes along and you have all these new sissy experiences. You have a lot to learn but you are coming along.”

The got back into the car and after driving a bit they pulled into a driveway of a very nice house.

“I want to show you off to my very best friend. I want you to be on your best behavior.”

They went to the door and she rang the bell. When it opened Bobbie saw another attractive woman in about the same age group, in between 45 to 50. This new woman was dressed in a lounging dress. It kind of looked like the kind you might have seen on women back in the 50’s, a bit like June cleaver.

“Diane, its so nice to see you,” Said the woman. “And who is this?” She looked at the sissy from head to toe.

“This is my new maid. His name is Bobbie. Isn’t he precious”?

“Hello Bobbie. It’s so nice to meet you. Come on in.”

She led them into a sitting room. “Sit here Diane, and Bobbie, you can stand just in back of her.” She smiled at them.

“So to what do I owe the pleasure of this visit?”

“I wanted to bring Bobbie over for you to meet. He came into the store yesterday to buy a new scarf and thing have progressed from there.”

“Oh? You have just met. He seems sweet.’

“He is. We went over to my place in the evening and he has accepted a position as my new sissy maid.”

“Your so lucky. I have been jealous of you for years. First that lovely husband of yours for all that time and now a new sissy of your very own, you go girl.”

“Bobbie I want you to go and make us some tea.”

As he left he heard the women giggle.

“He is so cute. I love what you have done with him already. Is he very submissive? I remember some of the things you have had your hubbie do.”

“Oh he is very submissive. I gave him his first spanking tonight. And if you want, I think the second could happen tonight, right here.”

“I would love that. I haven’t seen a spanking in a long time. Does he cry?”

“Well he did when I took the strap to his ass.”

They both laughed at that.

Bobbie returned with a tray.

“Bobbie, set it down here on the table and stand up strait.”

He did so.

“Ellen, do you see something wrong with this picture?”

“Of course dear, a maid always should have an apron on when serving.”

“See Bobbie, everyone knows that you aren’t to do any serving with out an apron on.”

“Mam, I don’t have one with me’

“That isn’t an excuse. You could have asked. I’m sure that Ellen has a few aprons around; in fact if you looked behind the door to the cupboard you would have seen one hanging there. I want you to look now, go and find the most feminine apron there.”

He returned with an apron. It was a bib style pinafore. Ruffles were all around the edges of it; it was also in a pretty rose color.

“Now take off your shoes, pants and blouse. Then put on the apron.”

He blushed as he took off his outer clothing, and standing there in his lingerie he put the apron over his head and tied a big bow. His Mistress took the scarf from his purse and tied it on his head.

“Get a chair from the dining room and put it over there.”

He got the chair and she sat in it.

“I told you before we came in, you had better be on your best behavior. You have embarrassed me in front of my friend and you have to be punished. Lie down across my lap, now!”

He knew what was coming next. She lowered his panties and started to slap his ass. He tried to block the hits with his hand.

“You don’t know when you have it good, do you sissy Ellen, would you get me a scarf and tie his hands?”

Ellen got a scarf from the hallway closet and knelt to tie his hands.

“Poor boy. You are a spanked sissy, but now you are a spanked sissy in front of a new woman.” She said as she finished the bow binding his hands.

The slaps continued for a while. With his ass still sore from before, it didn’t take long before he started to cry from the sting.

“Ellen, you know he insulted you too by not wearing an apron. Do you think you should punish him too?”

Ellen was in her glory. She loved to spank, but had not done so from the time her son had left the house years ago.

“If you think it will help, sure I will spank him.”

Ms. Diane Watson pushed the sissy off her lap. “Sit here my dear.”

“Bobbie I want you to kneel in front of Ellen, and by the way her last name is Smith, ask her very nicely to punish you.”

Bobbie knelt in front of this woman he had just met an hour ago and pleaded, “Ms smith, I am very sorry. I don’t know what I was thinking, would you please discipline me so that if its in your heart you might forgive me.”

“Yes sweetie, I will spank you and because you asked me so nicely, I may forgive you after.”

He lay across her lap and Ellen for the first time in years felt her hand smack an ass. She kept it up for a while. She could feel the sissy squirming in her lap. She could feel the hard on he had. She was getting sexually stimulated too. It is a heady feeling to have a grown man, although in this case sissy boy, in her lap getting his ass slapped. She felt the power, as the sissy cried for her. While spanking him she looked to her friend and saw a knowing look on her face. They shared a smile and she finished the spanking. She pushed the sissy on the floor in front of her.

He knew what he had to do next. He knelt up strait as he could with his hands tied in front of him.

“Thank you Mam, for punishing me.”

He then took his tied hands, and pushed the skirt of her dress up, and leaned in and kissed her on the panties.

“What a bold sissy he is!” Stated Ellen.

“And he isn’t done thanking you yet. Go ahead sissy; thank her like you would thank me.”

He still used his tied hands and lowered her panties, and then kicked her cunt. She spread her legs so the sissy could get a better shot at her. She looked at her friend and noticed that she had a camera in her hand. She watched as Diane took a few shots of this sissy; in makeup with the scarf on her head suck pussy.

He kept up at it using all the skills he and learned just the night before. It didn’t take long before he felt the woman having an orgasm. He looked up and saw the smile on her face. He turned and crawled on his knees to his Mistress.

“Thank you Mam, for my punishment.”

“You may just kiss my pants for now sissy.’

“Ellen do you still have the table?”

“Yes I do its in the basement.”

“Lets all go down there.”

They went into the basement and he saw the table they were talking about. It was the kind you might find in a Doctor’s office, the kind with stirrups for a woman’s examination.

Diane took off the sissy’s panties exposing his chastity belt.

“Get up on the table sissy.”

She took each leg in turn and put his feet in the stirrup. There was a belt at each and she tightened the belts around his ankles.

“Would you like to play?” she asked Ellen.

“Sure would.’

“She gave Ellen a small knife and said, “all you have to do is cut off the plastic lock, and I have another.”

Ellen cut off the lock and took off the basket from the sissy cock. It sprang to erection.

She rubbed and teased the cock for a bit.

For his part he had to concentrate. It would not take long for him to cum. It felt so good, this strangers hands on his cock. He was putting out some effort quickly into trying not to cum. She teased him some more with out really jerking the sissy off.

“Please, Mistress, I don’t know if I can hold out, please may I cum?”

“Yes dear you may, it was good of you to know to ask permission.”

His tormentor started to jerk him off. She stroked his cock and in just a few minuets, he came all over her hand.

“Now sissy, this is a new rule: if you cum you must eat it.”

He looked at her. Was there no end to the humiliations?

She brought her hand to his lips. He touched his tongue to the slime on her finger and for the first time in his live he tasted sperm. Even though it was his cum it was cum. Men do not eat sperm. However, sissies do. He was now a sissy. As he was licking her fingers he heard his Mistress say, “I hope you like the taste of your slime because you will be having it from time to time from now on. Each and every time you cum you will be required to eat it.”

After he finished cleaning her hand he thanked her for the pleasure of having an orgasm. He was dressed and they went home for the night.