She Found A Sissy free porn video

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had 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 who 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 sewing 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 attire under his 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 sox, 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 no, 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 think 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 toped 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 all 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?" "Oh yes, Maam," 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 tities," 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 legs 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 though." 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, but nevertheless, makeup? She did not waste 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 for later." She looked into his eyes in the mirror. Now come down stairs and we will have another glass of wine." "You need to 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 sissication. 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. PART 2 "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 Maam." 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 he was restrained to and asked, "Did you sleep well?" "Yes Maam." 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 without 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, Maam." "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 Best 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 nighttime 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 block. "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 get 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 twaise. 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, Maam." She released him from the spanking block; he knelt and kissed her panties. "Thank you, Maam. 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. There 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. He 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, whenever 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 goodbye 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." "Maam, 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 Maam, 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 Maam, for my punishment." "You may just kiss my panties 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 Dr'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. In the following weeks he had many lessons. Each day he was put into one of the seemingly endless maid's uniforms his Mistress had for him. The house was coming along nicely and after a time it was all polished, clean, and shiny. During the evenings his lessons in becoming more of a sissy were held. In the first week he had make up lessons where he was told to sit at the vanity and for hours he put on new make up and then took it off. He was shown how to apply it for daytime evenings, and special times where he would wear it looking like a slut whore. He learned all the color combinations and could do his own make up. It was in the second week that his new Aunty Ellen came over and taught him about a sissy douche. He was led into one of the locked rooms he had never entered before and when the lights came on he saw an examining room. It had a chair kind of like the one he had been jerked off in, but this one had more straps and knee holders beside the stirrups. Mistress Diane and Aunty Ellen had him strip down to his bra, garter belt and stockings. He was told to sit in the examining chair. First a strap was placed at his waist and he found that the chair ended before his would cheek fit on the seat. When his knees went into their holders he felt himself stretched out as much as his legs could. Each was strapped in place and his feet were put into the stirrups and tightened down. His arms were also placed at his sides and a belt at each wrist and elbow were tightened till he couldn't move at all. When he was fully in place, he felt very vulnerable. They had access to his most private parts. What he was to learn tonight was that there was nothing private on his whole body or in it. "Are you ready for some real fun dear?" his aunty asked. "I am ready for what you have planned for me, I am only a sissy and here for your pleasure," he stated. "I'm sure you are dear, but I really don't think you know what you are in for tonight," His Mistress told him. They left him here for a bit to think about what might happen. They went to her room and changed. They had the pleasure of helping each other into some latex clothing for the night's fun. Mistress in black and Aunty in white, they put on stockings made of the thinnest latex, and the same for the panties and bras. Then each put on a dress made out of thicker latex. Over the neck aprons of the thickest latex followed next, and finally they put on scarves on their head in peasant style. When the reentered the examining room, he gasped. The each smiled at him. "Well dear you are going to learn about how a sissy gets his douche tonight. Women have to douche their pussies to keep themselves clean. Of course a sissy doesn't have a pussy, but then again they do have a place that could be used like one. I am going to be using a dildo to train you so you need to have a nice clean place to put it." He was getting just a little frightened now. Dildo training, and cleaning, the only thing he could imagine was an enema. His Mommy had given him a few when he was a very small boy and he didn't like them then and he was sure he would not like one now. He saw Aunty Ellen take out a red bag. His worst fears were coming true. "Oh Please, Mistress, not an enema. I don't like them. Please don't do this," h begged. "Now lets not complain. Aunty Ellen and I have gone through a lot of trouble to get dressed just for this occasion, your first enema from us. Don't you like the way we look?" "Both of you look very sexy and you know I really want to do the best for you, Mistress, but enemas. They hurt and I do not like them at all." He heard the water running and saw his Aunty feeling the temperature of the water. He saw his Mistress taking things out of the cabinet. Hoses, clamps, and some things he had never seen before. She put them on a rolling cart with some other stainless steal things. He then saw her put on a pair of latex gloves. About th