She Found A Sissy By Donna Sash

She Found A Sissy

By: Donna Sash

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

a prequel to A new Friend. Women who feminize their men into sissies, and for some bi sex Read A One sided Marriage and this one before A new Friend

She Found a Sissy

by Donna Sash

She had been working at Bardwell’s for the last 10 years. Five years ago she moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales.

Women reacted well to someone who believed in their product. Some women just wore a scarf occasionally but a lot of her customers were regulars and followed her example and wore scarves of all types with all kinds of outfits.

She looked down to the end of the counter and saw something that she didn’t see all that often. There was a young man looking at the scarves. He seemed to really study all of them hanging on the display on the counter, and looked at the ones under the glass too. She didn’t want to scare him away. She had a lot of male customers, but most were looking for gifts for their wives or secretaries. Usually men found the first thing they were looking at and asked to have it placed in a box so they could get away from the woman’s department.

Some men though really seemed to like browsing and asked some real questions about their purchase. In addition, just a few really loved what they were looking at. This boy seemed that type. In addition, if they were that type they were very easy to scare off. She didn’t want to do that. First of all she needed some sales, and second he way really unusual because he had a neckerchief on.

Very few men wore scarves. It was nice back in the late 60’s neckerchiefs were in fashion and she loved the look on men. This boy, he seemed to be around 18 or 19 was well dressed. He had on dress slacks and a nice shirt. He had on a suede vest. His neckerchief was a little longer than the ones she usually saw on men and it had a very feminine pattern.

He reminded her of her late husband. He had passed away five years ago, almost the same time she came into this place, the scarf department. She had met him while they were back in high school and it was the time that the scarf for men was just starting. One night they were making out in the family room of her parents house and she told him how nice she thought he would look in a neckerchief. She put one around his neck and she saw just how aroused he seemed to be. From that day forward he wore that and many other things he never thought he would and it led to a very fulfilling if somewhat way left of the unusual marriage.

She walked over to the young man and asked if she could be of help. He explained that he was looking for something new to go with a new shirt he just bought. She asked to see it and was looking at a nice satin men’s shirt in light pink.

“I have a lot of scarves that would go with this shirt. What did you have in mind?” she asked.

“Well I’m not sure. I will mostly be wearing it with a black suit. I don’t like ties and want something that would go in many occasions.”

“Why don’t you come down to my better scarves then I have some there you might like.”

They went down and she pulled out a few scarves. He picked a nice one with a dark burgundy border and paisley in the middle.

While he paid for it she asked, “ I don’t get many young men here to buy scarves, and while I am pleased that you came here, I was wondering, do you often buy scarves?”

“I always wear s pretty scarf. My mother wore scarves and when I was a boy she taught me the pleasure of scarves. I have a few that I wear a lot.”

She then took a step that wasn’t very like her and she told him, “I have a very large collection of scarves at home, if you are interested I would love to show them to you”.

“If it wouldn’t be too much trouble, I would love to.”

She gave him a card and told him she would be home by 7 pm.

As he left the store he was thinking about his luck. She is a very good-looking woman. A little older, around 45 or so, but just the kind of woman he liked to spend time with. He loved his mother and while she was still alive he spent most of his free time with her. A lot of his friends didn’t know what to make of a boy that would rather spend time with Mommy, instead of playing out side. His Mother taught him many things that boys usually didn’t learn. He was well versed in home making. He could do almost anything the girls of his age group could and maybe some things they didn’t. His mother was kind of old fashioned and he learned how to do things like real sowing and hair care, done the way it was done in beauty shops. He found girls his age just didn’t appreciate a person who could do things as good or better than them. Older women loved it though found it very nice. While his mother was still here her friends would come over to visit and he would do things like making tea and serving them. They all loved it when he was around and he felt that it was great to be accepted.

What he didn’t know is that the kids around his age referred to him as a sissy behind his back. What they didn’t know was that he was a sissy. His mother had shown him some other things too. She taught him that it was ok to have some effeminate feelings and actions. She also showed him how nice it was to wear feminine under clothing. He wasn’t a transvestite, at least not in his mind. Sure he wore panties, and sometimes a camisole under his shirts. He wore stockings not socks, but these were ok. He didn’t wear dresses or skirts, and never wore makeup, not like the pictures of drag queens he has seen.

Now he was thinking about what he should wear for his visit with his new friend. He selected a nice pair of slacks and his new shirt. For underwear he wore plain white panties and a nylon tank type camisole with a slight lace trim, a pair of stay up stockings and he was ready to put on his new scarf. He then topped it off with an off white cable knit sweater. He was off to her house.

When she got home she hoped he would show up. She went right to her bedroom and changed. She put on a white blouse with an A line black skirt. High heels went with her stockings. Then she took a large square scarf, draped it over her shoulder, and tied it off on the other side with the ends hanging in the front. Looking in the mirror she presented a formal woman of her age group, the kind she hoped he would respond to. She really wanted him to be responsive to her. She didn’t know why, but there was something special about him.

After her husband passed she really didn’t have anything to do with men for a long time, and when she did, she didn’t like what she found. Most were looking for some short-term fun. Most of them were demanding. Well she liked to be the dominant one in a relationship and the men she ran into were not the kind she wanted. She had tried to meet some people on the Internet and found that almost all of them were just into it for a sexual thrill. It wasn’t that she didn’t like sex, in fact she pleasured her self almost every day, it was just that she wanted to have the kind of man she wanted and for him to show her the kind of submission that would turn her on, and not off like most she had met.

Finally she sat at her vanity and did her hair in an up sweep to get it off her neck to have that matronly look. She put things away so her bedroom was totally clean and went downstairs to wait.

It wasn’t long and the doorbell rang. She went to open it and let him in. As the door opened he entered and looked in on a nicely appointed living room. It was Very feminine in the window treatments and colors on the upholstery. The rose rug brought it all together.

“I thin your house looks very nice.” He stated.

“I’m pleased you like it. Come into the den.” She led him through a door into a sitting room. It had two sitting chairs with a tea table in between them. Sitting on the table was a silver wine cooler and glasses.

“Would you like a glass of wine?” She asked.

“Only one, please, I am driving”

They sat and she poured.

She looked at his pink shirt with the scarf around his neck and smiled. She wondered how he would respond to her as she started his domination. She stared at him hoping that she might intimidate him a bit.

For his part he did feel a little intimidated. She looked like an old time schoolteacher. She reminded him of some of the women who met with his mother back when he would serve them.

“I was wondering about your scarves? Just, how is it that your mother started you wearing them?”

“I was around 4 or 5 and I went into her bedroom this day and said, “Mom, I can’t tie my tie”. She looked at me and said, “here honey, lets put this scarf around your neck, and then you only have to tie a simple knot”. She put the scarf on my neck instead of under my collar. She smiled at me, and when I looked in the mirror I thought it looked pretty. “Gee, thanks mom, that’s a lot easier” From then on I would wear a scarf instead of a tie. She bought me some of my own”

“Were you very close with your mother?”

“Mom and I did everything together. She took me shopping with her, she taught me how to do house work, when it was time for me to learn how to do things like the laundry or harder things she would spend a lot of time showing me the right way to do things.”

“You two must have had a really good relationship.”

“We were very close I miss her very much. She gave me direction, these days I am kind of lost with out her but I’ll manage.” He said with a sigh.

“Well why don’t we go and look at what you came over to see. Would you like to leave your sweater here, I would much rather see you in your new blouse.”

He felt kind of funny when she said blouse but he took off his sweater and left it on the back of his chair.

She led him up stairs to her bedroom. She had a lace topped canopy bed. The carpet here was an off pink, it went well with the floral pattern on her bed cover.

Her vanity had a lace scarf on it that matched the dresser scarf and that on her chest of drawers. She had him sit at her vanity and opened the bottom drawer. He could see the top scarf in the drawer it seemed to be a really expensive one. She took it out.

“This one is my most favorite one, it’s a Hermes.”

She folded it into a triangle and draped it on his shoulder. He looked at it and loved the way it went with his pink shirt.

“Pretty isn’t it?”

“Yes it is.” He said smiling.

She went to her dresser, opened a drawer, and took out another; she placed it on his other shoulder. It wasn’t as expensive a scarf but it also went with the pale color of his shirt.

“See you can go a lot of ways with the colors or patterns.”

He smiled at her. He hadn't felt like this since his mother had passed away. His new friend had the touch to make him feel like he fitted right in.

She saw the look of pleasure on his face and knew that this was a boy she could mold to her liking. She knew that he loved all this feminine bonding that was going on here. She was ready to try something. While putting the scarf on his shoulder she had noticed his camisole. She knew that he was wearing women's clothing and she was pleased. He was a sissy. She loved sissies. Her husband was her special sissy and they had done a lot with it. He being her submissive through out the whole time, she being the one who was in control.

She took out another scarf. The background color was almost the same as his blouse. She approached him folding it into a triangle, and placed it on his head and tied it under his chin. He started to blush. No one but his mother or some of her friends ever saw him with a headscarf on. This was as feminine a thing he ever wore on the outside. He looked at her, saw the look on her face, and didn’t know what it meant, but he could tell she was pleased.

“Do you like this scarf?” She asked.

“Yes I do, but I usually don’t wear scarves like this.”

“Well you should. Your face goes well framed in this color. It suits you.”

“Its kind of girlish though.”

“And you mind that? With your pretty face, you could look very girlish and feminine, is that a problem?”

“I guess not.” He stated with little enthusiasm.

“I like it she said. Moreover, lets get it out in the open ok; I know you’re a sissy. I can see your camisole with its lace trim, so admit it.”

“Well I do wear some woman’s things, but I’m not a transvestite.”

“I didn’t say transvestite, although you might fit into the real definition. What I am talking about is a sissy, an effeminate personality. Boys that wear panties and camisoles under their clothing are sissies.”

“But! But, no one is supposed to know about that!” He said shamed. “I have to go.” He took the scarf off his head and started to rise.

“Its ok! Hold on, its ok, I like sissies. Don’t you think I knew when I asked you over?”

.” How could you have known?”

“A woman can tell. In addition, I’m glad that it’s out in the open now. Sit down and relax. No one is going to hurt you, and no one is going to think any less of you because you’re a sissy, in fact, like I told you, I like sissies. My husband was one.”

“Really”?

“Here look at this.” In addition, she handed him a photo album.

When he opened it he saw a man in lingerie. There was page after page of the same man in different female clothing. Many of the pictures had him in lingerie but some had him in full dress, skirts, dresses, and each with a scarf on in some way. He was speechless.

“I’m sure your mother knew what you were like when she first gave you a pair of panties. It was your mother wasn’t it?”

“It was just after the time she had me wear a scarf. She came into my room one morning and said we were going to have some company that afternoon and she wanted me to be dressed special. Mom took me into the bathroom where she had run a bubble bath. She usually didn’t stay with me but on this day she shampooed my hair and washed me all over. When she dried me with a towel, she then showed me my underwear. It was a girl’s tee shirt and a pair of girl’s panties. “Do you like them?” she asked me. I told her they were pretty, and asked if it was ok for a boy to wear girls things. She told me some boys liked to wear girly things and I could if I wanted to. I told her I would like to try at least. She pulled up the panties and then put the tee on me. I looked in the mirror and loved it. She then told me that this was going to be our special secret. I was never to tell anyone, not even her women friends that usually came over, because some people wouldn't understand why a boy wanted to be so pretty. She said I was her special boy and I could do things that other boys couldn’t.

After that I had many new things to wear, but they were only for special occasions and it was kept as out secret all these years. You are the first to know.”

“I feel very special that I do know and I want to share this with you, if its al right with you. I want to be like a mother to you. I want to teach you a little more about what you have been doing. I what to show you what it is like to be and “Adult sissy”, would you let me?”

“I guess its ok.”

“I will never hurt you dear boy, but you might not understand all we will be doing. I have a lot of experience at this. My husband spent his whole life with me as a sissy. I do have some other pictures to show you, but first, I what to dress you. Would that be aright?”

“What do you mean dress me?”

“I’m going to put you in girls clothes. I’m going to let you see who you really are under all that boyish exterior.”

“You’re going to make me into a girl?”

“No sweetie, I’m going to make you into a real sissy boy, although you most likely will look like a girl, you will be the sissy that is inside just waiting to get out. I could tell when you came to my counter, I knew that there was something about you, but when I saw you at my door, in your pink blouse and scarf, I knew just what you are and that you should know it too. Will you let me make you into what you really are?”

“Yes Mam.” He said as if he was speaking to his mother.

She smiled at him and said, “I think you need another bubble bath. Just like your mommy, I am going to start you all new. This time you are going to learn how an adult girl dresses. I think you’ll love it.”

She entered her bathroom and started the water running. He wondered just what he was getting himself into. He never really had girlfriends. He never dated like so many of his friends did. Now this woman who he just met today was going to see him naked and treat him like some kind of male Barbie Doll. Did he really want this? He didn’t know but it did really sound like fun. The other thing was, he felt good. He felt like he was back with mommy. Mommy had played some dress up games, but only with lingerie. He knew that when they were done he was going to really look like a girl.

She came back into the bedroom and looked at him. She could tell he was scared. She went over to him and said, ”It’s going to be ok, honey, and you are going to love this, if what I’m seeing in you is true”.

And with that she started to unbutton his shirt. He looked into her eyes with a questioning look on his face.

“Don’t worry sweetie, I’m going to take good care of you. You will feel like a little boy again, but this time I will be acting like your mommy, and mommy will never hurt her little boy.”

He couldn’t believe his ears. She was treating him just like mommy did. Could this be real? Could he really be lucky enough to have a new mommy in this wonderful woman? He was down to his panties stockings and camisole now and he had a problem. Feeling himself in his panties he was growing hard. He was embarrassed. She noticed it and smiled at him again.

“I see you like this already.”

He blushed even more.

“I want you to know that you are showing me just how much you like this kind of treatment. All sissies get hard. And all sissies need to be taken care of.”

“What do you mean?”

“You will really like this. You masturbate don’t you?”

“Yes.” He said sheepishly.

She lowered his panties and his hard on stuck out the way a young man usually did in a sexually charged atmosphere. She sat down on the toilet, pulled him closer, and started to stroke him. She had a hankie in her other hand. He looked down at what was happening to him.

She said. “ Let me know when your ready, we don’t want to make a mess.”

With that she masturbated him for a few minutes.

“I’m ready now,” he said

She took the hankie, placed it at the tip of his hardness, and felt him start to orgasm in her other hand. She wiped it off and told him to take all of his things off and get into the tub. She took off her scarf and blouse and knelt beside the tub. She took the shampoo and washed his hair. She told him to keep his arms away and she washed his whole body. She spent extra time by his cock and balls teasing him and worked her fingers at his dark hole. Finally, she started the water in the handheld shower and rinsed him off as the water emptied of the bath water.

Now I want you to stand. She got a pink bottle and started to put the pink stuff on him. She made sure she covered him all over. She started at the neckline and worked until she had it all the way down to his toes.

“What is this?” he asked.

“Oh you’ll see.” She smiled.

He stood there for around twenty minutes and finally she took the hand shower again and started to rinse him off. He did not have much hair on his body, but still it rather shocked him to see it all coming off him during the rinse.

She took a nice fluffy towel and dried him off. They returned to the bedroom.

“Now I am going to dress you. You might find that some of the things I put on you are shocking, but that is the old you thinking. I am going to start to mold you into something else and it’s going to start now. One thing, some of what I am going to put on you are from my husband. These things are really special to me and for me to let you use them is, well, I don’t know how to put this into words, but I never thought I would ever use them again.”

She opened the closet and he saw another chest of drawers in the back of it. She went to a drawer, opened it, and took out a pair of panties. They were the most feminine panties he had ever seen; in a pink with white lace trim, they were something else. She drew them up his legs to his waste. She took a matching bra and started to put it on him.

“This is your first bra. It can happen only once, like so many things we are going to be doing, but a boy’s first bra is a step that once taken can never be reversed. Boys do not need a bra. Sissies wear a bra and it shows them that they are a sissy.”

She put it all the way on him and clasped it behind his back. She then put in silicone breasts. She worked them until they fit perfectly.

“Now you have real sissy tits.” She said. “ What we have to do next is let you feel a little constriction.” She held up a pink and white lace trimmed cincher. She started to put it on his belly. As the hooks were locked, he felt his tummy being brought in. It had laces in the back and she started to tighten them. He started to feel as if he could not breath.

“You have worn stockings before, but this time it is a little different. Stockings on freshly cleaned lags feel better. Now here are some stockings, I want you to put them on, and remember keep the seams strait up your leg.”

He sat at the vanity chair and put on the stockings. They did feel better. The more this happened, he was feeling better about this complete possess. When she first started, he had some feelings of reservation, but now that things were coming along, he liked it more and more. He had been wearing feminine underwear for most of his life, but this lingerie was so feminine that he could hardly stand it. He was glad she had masturbated him before because he was already feeling that hic cock could get really hard again.

For her part, she was having a great time. It had been a long time for her to play with a man, and this boy was going to be the best sissy she could imagine. He did everything she asked. She could not wait until she had him fully dressed. What she did feel was a sexual thrill she had not felt since her husband died. Of course, his little cock had felt great in her hands and she loved it when the little thing spurted into her hanky. She would keep it for a memento of this her first time with her new sissy.

“Have you ever worn high heels?” she asked.

“Err no. I have worn female shoes, but usually moccasins or flats.”

She went back into the closet and came back with a pair of pumps with a 3” heel.

“Here try these on.”

He put the first shoe on and it fit. When he had the second one on he tried to stand. He was a little wobbly.

“You will learn to walk in them, it might take a little time but.”

Next came a pink camisole and a matching half-slip. He put these on and as he looked down he saw a rather feminine body.

She took out a black skirt. When he put it on, he saw that it only came to his knees and that it flared out some. She then put a white lace covered blouse on him. He could see the pink through the shear blouse.

“Now sit here at my vanity, I’m going to do your makeup.”

Make up? He thought that this might be going too far. Sure, he was here dressed up as a girl. Nevertheless, Makeup?

She did not waist any time and started to put on his foundation. As it was drying, she started on his eyes. She used deep blue mascara, and put it on thick. She lined his eyes, for a dramatic look. She used a few colors in shades of blue to do his eye shadow. Then powder all over his face and finally some blush. She finished off her creation with deep pink lipstick.

Back into the closet she went and after a minute. She came back with a cute blond frosted on light brown hair wig. She put it on his head and told him she had the finishing thing.

She came over with a pink scarf with deep red roses on it. She put it on his shoulder and tied it off, draping the ends in front of him; it looked like the way she had worn hers before.

Now go look in the full-length mirror while I get my blouse on again.

He looked at himself and thought that maybe it was herself? He was beautiful. He looked better than many of the girls he saw at school or even a lot of the women he knew.

She came behind him and gave him a hug from behind.

“Well my little sissy what do you think?”

“Its fantastic. If I did not know I was a boy, I do not think I could tell. Thank you.”

“I have ways that you will thank me later.” She looked into his eyes in the mirror. Now come down stairs and we will have another glass of wine.”

“You need t learn how to sit in a skirt. You look like a boy in a skirt. Keep your legs nice and tight, and if you want to cross them do so at the ankles. There is a lot to learn to be a good sissy, but first you have to make a commitment. That’s what we will talk about. First of all, how do you feel and do you like the way you are now?”

“ I like the way I look. I feel so feminine dressed like this. I really feel natural. I never thought that a skirt and makeup would be something I would want, but looking in the mirror it was just so special. What kind of commitment?”

“First let me ask you a few questions. Tell me what do you do for a job?”

“I’m in between jobs right now.”

“And where do you live?”

“I have a small apartment across town.”

“Then you do not really have any other commitments right now?”

“No, not really.”

“Then the commitment you must make to me, if you really want to continue, is to come here to live in my house and become a full time sissy under my training.”

This is a big step, he thought. What would it be like? How would it feel living under someone else’s roof? What kind of rules? So many questions were rising in his mind.

She looked at him, he was so cute all feminized. She could see the confusion and dough on his face. She could see that he needed more information.

“This is how things would be. I would take care of the expenses. You will earn your keep by being my sissy maid here in the house. You will have duties and chores that must be done. I will inspect your work. If it is done correctly every thing will be all right. If not, I will discipline you.”

He looked at her with a look of wonder on his face. Discipline? He wondered.

“My discipline will not be harsh just fitting. I will use things like spanking, humiliation, and even more sifficiation. I know of things that will make you blush with embarrassment, and you will love it. I know how sissies are. Each of you really wants to be exposed as the sissy that you are, but the idea of exposure really is embarrassing. This is a good thing. You will learn things that you will really get excited by, but at first you won’t like them. This is where my fun comes in. I love playing with a sissy’s emotion.

In addition, in a sissy’s sexual expression, your sexual identity will change over time. My sexual expression will have much to do with you. In some ways you will become a sexual maid to me also. You will have sexual duties, and they will be completed to my full satisfaction, or you will be sexually disciplined. They will include denial of orgasm, punishment enemas, and once again sexual humiliation and exposure.”

She looked down to his skirt and saw that it was tented. All of this talk was stimulating him. He was really hot. She could tell that he was having a hard time trying to keep it on, but she could tell, he really was excited by what she had to say.

“Well my dear, what is it to be, Shall you become my personal sissy?”

“It all sounds so? So? I don’t know. Oh my, I really want to, but I am afraid.”

“Of course you are. I would be surprised if you weren't. That is what makes it so good. The uncertainty of it all. You will be committing to a woman who you have just met. A woman who has told you that she will discipline, spank, and humiliate you. A woman who is saying that she will expose you as the sissy you really are. Look at your skirt; your body is answering me, now it is time for your mind. What will it be sissy boy?”

“Yes, it does sound so exciting. I will be your sissy. I will commit to your training. I haven’t felt so sexy as I do right now. I love the way you look and dress.

Please, be my Mommy. Please let me return to the best time of my life. I want to work for a woman, have her give me direction. Mommy used discipline on me when I was young. I understand the need. And, yes I will be your sexual servant.”

“Then my dear, come over here and kneel in front of me.”

He did.

“Now lift my skirt, and kiss my panties and show me that you will respect me. Kiss my panties and show me your commitment to me. Kiss my panties and seal your fate.”

He raised her skirt and saw the wonderful panties she was wearing. He leaned in and kissed her right on her mound through the panties.

“Now lower my panties and kiss me on my flesh.”

He did so. He had never been this close to a woman before. Sure he had seen his real mommy with out her clothing on. He had bathed her. This was different. He put his mouth at her opening, puckered his lips, and kissed her pussy. He sold smell her womanly sent. He felt very submissive.

“That’s a good sissy. Now I want you to lick me. I want you to show me just how much you want to be my sissy. I want you to make me feel as good as I did for you just a little while ago. Eat my cunt.”

He started to lick her. He could taste her secretions. He felt her flesh on his tongue and it was good. He worked it all over her labia. His tongue went up and down her pussy lips and he could feel her start to respond.

For her part, she was delirious. She loved it. Here was this boy, dressed in full sissy clothing a boy she had just met today and he was on his knees sucking on her cunt. She had not had her pussy licked in a long while and it felt good.

“Suck on my clitty. It is that part that looks like a tiny cock in the hood.”

Moreover, he did. He took it in his lips and softly sucked. His tongue darted out and licked her nub. He worked on her and he felt her squirming. He could tell that she liked what he was doing, and then she came.

She was humping his face and she started to feel it. She screamed. I’m Cumming. She rubbed her cunt on his face even more.

“Keep going. Don’t stop. Lick my cunt; fuck it with your tongue. Show me, sissy, show me how much you want to be my sissy.”

He worked even harder. He placed his hands on her butt cheeks, pulled her cunt to his mouth, licked it, and stroked it even more. He circled her clit with his tongue and felt her rise to greater heights of pleasure.

She came again. “Unnnght Yes! Yes!” It was so good.

She released him and he fell back a bit still on his knees.

“That’s it. That is the way you will pleasure me always. My good sissy.”

He looked at her. He felt a love starting. He wanted to do any thing to see her pleased like this. In some was this was better than pleasing Mommy. He loved doing things for his mommy and loved the praise he got. Nevertheless, this was different. He knew he had pleased his new mommy. He knew that he did all right.


Kristen