Being Trustworthy Part II free porn video

Becoming Trust Worthy Part II By Sissie Maid Cuckold With dinner and Karen both finished... John was sent to cleaning up the kitchen as Karen sat there watching and instructing him. She noted that John was allowing his arms to fall by his sides when he was not using his hands. Karen approached him and said, "John, you are not being efficient the way you are holding your arms. I want you to allow your arms to remain parallel to the floor and let your wrists go limp so your hands hang down, yes like that." "But Ms. Karen isn't that...well...like girly or something?" "John you must stop with this girly stuff! It isn't about being a girl it's about being efficient. Did I say it was about being feminine or did I say efficient?" "Efficient Ma'am." "That's right John now if you are ever to get what you want from me you really need to wipe out these ridiculous concerns about being to girly and stop thinking that way. I thought you figured out what this was about, putting you in the top 10% of men. Yes, I let you wear a few feminine things because you have earned them and it's a privilege and all because you have pleased me and are so damned sexy in them but if you keep up with these ridiculous suspicious questions about being turned into a girl...well, I just won't let you wear them anymore and that will be a huge turn off for me sexually...so what is it to be?" "I'm sorry Ms. Karen I guess it was dumb of me, please forgive me I am very sorry." "Ok I guess I forget you're just a boy and don't understand most of these things. You know what... I am sorry too and to prove it to you I am going to let you wear one of my nightgowns to bed tonight, but only if you promise not to have these silly thoughts about me trying to feminize you again. I mean John Really...think about it...if I wanted a girl don't you think I could get a real girl?" "Thank you miss Karen, thank you for understanding, forgiving me and allowing me so many privileges. And yes Ma'am I am sure you could." "One more thing John, I want you to wear the penis gag to bed tonight to help you remember what your mouth is for and it is NOT for complaining or challenging, that is very un-becoming of you to complain or question, it makes me feel bad." "Yes Ma'am Thank You Ma'am." "Ok come here let's put this one on you, it's my prettiest and most favorite nightgown." It was a pink flimsy thing with lots of lace and ruffles, ultra-feminine and as it slid over Johns body briefer and the hem touched his nylon covered legs a shiver went through his entire body making him feel ultra-submissive. And when Karen fastened the penis gag into Johns mouth he was feeling as helpless as a baby. Completely vulnerable and thinking only of Karen. He was beginning to idolize her and his face showed it. "You look so sweet and sexy... I am going to have to do something about it. Turn around and fold your arms behind your back." John now feeling totally helpless did as told and could feel his penis pulsating at the thought of being dominated by Karen. She applied the two plastic wire ties securing his arms and told him to lay over her lap on the bed. She took the vibrator and worked it into his bottom and barely playing with his pantie covered penis brought him to the brink of climax and then backed off over and over again while she spoke to him. "Do you like the name Cindy?" John nodded his head. "I do to; I think it's a very pretty name. I thought you might like it since that was the name you came up with when you purchased your Princess diary. By the way I think a Princess Diary was perfect because I think of you as my Princess... my Pretty Princess. I have even considered letting you get a Princess dress and high heels after you earn your maids uniform. It makes me so hot when I visualize you dressed like a Princess. I can't imagine how wonderful sex with you would be if you were pretending to be my Princess...would you like that John?" John knowing full well what Karen wanted to hear and what would happen if he disagreed nodded his head again. But there was more to it than just agreeing with Karen. The thought also stimulated John. Oh maybe it would not have if he was not sexually worked up but he was and the idea was quite stimulating. Karen was making it a point for John to associate any and all pleasure with being feminized and dominated and it was working while convincing him he was not being sissifed. "You know John you have a pet name for me, "Ma'am or Ms. Karen and I really like that. I think I should have one for you, don't you?" John nodded his head again. Karen smiled at his response, "Good glad you agree, I was thinking of Cindy. I think it's perfect because you choose it and it symbolizes your dedication and obedience to me. You must be aware Cindy how much better our relation has become since you submitted to me and began to obey me without question. I am sure you see the benefits just as I do don't you Cindy?" John nodded his head vigorously about ready to cum. "You are coming along so well Cindy; I am so proud of you. I am truly amazed at how attractive you have become to me and I have a feeling that is only going to increase. Have you thought about hiring a body guard to protect you from my sexual advances Cindy?" This time Cindy shook his head to indicate no. He was looking forward to all the promised sex with his beautiful girlfriend Karen and the rest of this was just things to deal with and then in his mind to just let go. He knew Karen could not possibly resist his attractiveness and soon would be laying under him being banged and banged. He just knew it was mostly because it was how sexy she found him and how manly she said he was even when wearing the most feminine things. He was somewhat confused about how he was becoming more of a man while he seemed to be getting more girly but Oh Well Karen said it was so, so it must be! The next day when Karen got home Cindy was writing in his princess diary laying on the bed like she had instructed him to. She read what he wrote and he had mentioned he was having trouble keeping his nylons up. When she read this part she stopped and said, "Oh Cindy baby, I am so sorry. I thought those with the elastic tops would stay up for you, lets fix that right now you shouldn't have to deal with that. It's all my fault honey here put this on." Karen handed him a pink garter belt with plenty of pretty lace on it. Cindy look confused by it so Karen put it on him and showed him how to run his leg to attach the back straps. "There sweetheart, I really shouldn't let you wear garter belts but since it was my mistake I will and we won't worry about it." Cindy studied the new feminine item and accepted everything Karen had said to him. After dinner Karen called Cindy to her. "Cindy, come here darling. I want to have a smoke and read the paper and while I am doing that I want you by my side, please turn around and put your arms behind your back." Cindy turned and meekly obeyed knowing what was about to happen. Karen took Cindy's arms and tucked them up his back and secured them with two plastic wire ties like always. "Now I want you to kneel on the right side of my chair facing out." Cindy again complied. "Now Cindy I want you to sit back on your feet and tilt your head back." Cindy complied again and Karen lit her cigarette. "Ms. Karen I didn't know you smoked." "Yes Cindy I do occasionally when I really want to relax. But Cindy don't you understand that it is rude to question me? We have talked about how much I love your submission and obedience. Submission and obedience are virtues Cindy; you do want to be virtuous don't you? You do want to make that top 10% don't you?" "Yes Ma'am." "Does it matter to you if I smoke or not Cindy? And if it did do you think I should care?" "No Ma'am." "That's right Cindy so now matter my answer its unimportant. No matter how you might feel its unimportant. What is important is that I get to relax and you use your mouth for what it was intended for Cindy which is NOT talking." "Yes Ma'am." Karen went back to reading and when her cigarette ash got long she told Cindy to tilt her head way back and open up wide. Cindy complied and Karen flicked the ash into Cindy's mouth. This surprised Cindy and she instantly closed her mouth and half gaged. "Did that startle you Cindy, "said Ms. Karen as she laughed. "Yes Ma'am, why did you..." "Would you rather it fell on the floor and then you had to lick it up?" "No Ma'am but..." "But what Cindy? Your mouth is for my pleasure and I was nice enough to share my cigarette with you I hope you're not going to complain and make me mad." "No Ma'am I'm not I was just wondering..." "Wondering why I put the ash in your mouth?" "Yes Ma'am." "Cindy not 3 minutes ago we had this discussion. Does it matter why I used your mouth for my ashtray? Does it matter what you think or what I think?" "No Ma'am." "That's right Cindy. Ask yourself this. Are you better off now than you were two weeks ago with me?" "Now Ma'am." "I think so too. I think we have made tremendous progress these last few weeks but if you don't and you want out just say so and I'll help you leave." "Oh no Ma'am that's not it at all I don't want to leave. I just dint know you were going to do that that's all Ma'am, I'm sorry Ma'am." "If I didn't think it was important or good for you I would not have done it Cindy. Whatever I do is for you to help you. Being my ashtray shows dedication and effort on your part. It shows me you are serious about our relationship. It shows you can be useful in so many ways regular looser men are not. Now do you think those are good things?" "Yes Ma'am I sure do." "Then you understand and agree that being my ashtray and not complaining is important and good for us don't you?" "Yes Ma'am, I do." "Good then while I am finishing my paper and cigarette I want to see your head tilted back and mouth open at all times." Cindy instantly did as Karen had told him. Karen smiled to herself at how simple minded he was and went back to reading. During the course of her reading she flicked ashes into Cindy's open and waiting mouth a dozen times without resistance or complaint from Cindy. When she was finished she flicked the cigarette but into Cindy's open mouth and said, "I'm done dear finish it off." Later in the bedroom with Cindy over Karen's lap, the vibrator in Cindy's bottom, Karen spoke of how proud she was of Cindy and how pleased she was with her progress. Karen was now referring to Cindy in the feminine form. Cindy simply accepted it. Then Karen said, "I was especially proud of you when you were next to my chair. You made an excellent ashtray and I have no doubt that with a little more practice you will be a fantastic ashtray. I hope your proud, you should be." Cindy thought this over, it was good that Karen was proud of her and it was good in how Karen was making Cindy feel right now. He thought about being an ashtray and while the taste was terrible, especially having to swallow the butt and how it made him feel funny, weak and submissive. Along with what Karen was doing to him at the time he simply succumbed to her will and agreed. Cindy replied, "Yessss...Ms. Karen...I...ammmmm....ahhh, oooooh, very ...proud!" he went into body shaking organism as his mind associated all of the things being done to him and the ashtray incident with the pleasure Ms. Karen was giving him. She milked him dry and then eased up enough to allow him to come down but not enough to allow him to come down all the way. She slowly caressed his penis through the panties as she said, "Cindy, I want you try and remember the importance of embracing your bra and panties. Think of all the wonderful things doing that has done for you. You are in an amazingly wonderful position right now. Realize it is the key to our closeness, my pride in you, my faith in you. Understand that your submissiveness and obedience have been key to getting you where you are. No other many has this with me Cindy, only you and it's all because of what we are talking about." "Yes Ms. Karen I think you are right." "Good girl Cindy, good girl. I am so proud of you. You know what? I'm going to let you brush my hair for me before we go to bed." Cindy liked that idea and enjoyed learning how to do it properly. In the morning Karen gave Cindy a fresh pair of nylons and a pretty red garter belt to wear under his clothes to work. She told him she shouldn't let him do this because it really was way to special but since she was so happy with him she would. Cindy smiled curtsied and thank her. At work the girls just seemed to be more and more interested in him. Lisa, the payroll clerk was especially interested. Oh not in a sexual way but in a curiosity way. Then she noticed that John was wearing nylons. She was sure of it but didn't say a thing but kept her eyes on his ankles to see when he sat if they looked like nylons. Sure enough after several trips of made up reason to talk to him she was positive. She knew all too well what a pussy whipped male acted like and this had been her suspicion all along. She did everything she could to have John around her and the other ladies in the office. They would all go to lunch together and each day it seemed she could tell John had advanced into a deeper submission. John spent the rest of the two weeks repeating his submissive acts but also getting deeper and deeper into Karen's control. She had him doing all of the housework, cooking and laundry. She had increased his falsie size to a full C cup and had gotten him a corset. He now had pink toe nails to help keep him from making runners in his nylons. Ms. Karen had informed him there was a dramatic reduction in runs because of this polish there really was not. He had been allowed to wear a nightgown, of which he now owned 5, to bed every night and was regularly wearing the penis gag to bed and keeping it in during the day when home until Ms. Karen removed it. The girls at work had started to touch him, mostly on the middle of his back but once or twice in the upper center of his chest. They asked him about his Girlfriend which he accidently referred to as Ms. Karen a time or two catching their curiosity. He explained it away as being polite. After that they all referred to her as Ms. Karen also stating it was a sign of respect which caused John to smile with pride. They were all so nice to him and so full of questions. When Angie found out he did all of the housework she exclaimed how wonderful that was and wish she had a boyfriend who did housework and how she would admire him. When Lisa discovered he had given up his driver's license and took public transportation to work while Ms. Karen drove her car she exclaimed what a righteous man he was and how proud she would be to be his wife. John had become a female's dream come true, submissive, obedient, faithful and compliant. Now John didn't see it that way at all he was a stud in his own mind so attractive to a beautiful woman and she could not keep her hands off of him. He was a top Man a top 10% of all men, Karen had said so and it was his brilliant deductions that got her to admit to it. Tonight was Friday night and the two weeks were up and Ms. Karen had promised him his maid's uniform reward, he could not wait. This also meant he was to have sexual intercourse with Karen...his dream of well over a year. It was all coming together and he was finely going to get what he deserved! He took the bus home, Karen having sold his car the week before and placing the money from the sale into her bank account providing a safe place for him to keep it. Upon arriving home, he took a shower and got ready with his nylons, panties, stuffed bra, body briefer and corset. Exactly what Karen had told him to do. He stood by the front door awaiting her arrival and didn't have to wait long. Upon her entering the home Cindy provided a proper curtsy to Ms. Karen even though he had no hem to hold out during his dip. Karen smiled brightly at her Princess and kissed him on the lips followed by cupping his bottom. "Come with me my sweet Princess we are going to break new ground tonight and this entire weekend. This is going to be great, I have waited way to long for this night my darling Cindy." They entered the bedroom where Karen immediately began to lay things out on the bed. First a very full petticoat and then a French maids uniform, collar, cap, heels and an apron. "But Ma'am, I thought you said I had to wear a plain maids uniform?" "Well yes I did but my fantasies got carried away with me so I got you one of each and we can try them both and see which one we like the best. But if you would prefer the plain one we can do that first?" "Oh no this is fine Ma'am really it is; I think that's a wonderful idea." Karen smiled knowing Cindy would go this route, after all what sissified male wouldn't? It was all about instilling the desire for the feminine in them which was not that hard and then allowing them to chase it which as a lot of fun. Oh yes the plain uniform would be used and used a lot but for now it was all about illusions and pleasure and putting the two together in an irresistible package! "Oh Ma'am this petticoat feels divine. I just love it thank you Ma'am, it is so nice and so pretty, look at how it swishes!" "I agree Cindy its very pretty on you and very, very sexy too, I hope we can get you fully dressed before I can't stand it and have to fuck you!" and they both giggled. Once Cindy was fully dressed Karen smiled at her and said, "Were not done yet honey, we need to add the accessories." She sat Cindy down and applied make up and finger nail polish to match her toe nails. Karen even shaped her eyebrows through tweezer plucking! Cindy felt so submissive and sexually stimulated she offered no resistance at all. The whole matter was having a strange effect on Cindy. Each step seemed to cause her to become more submissive while increasing her obedience. It was almost as if she were in a hypnotic trance. When the makeup was applied Karen put a wig on Cindy and as the long hair fell on her neck it sent shivers through her body causing even greater submission and subservience. After the wig was properly situated and brushed out Karen place earrings on Cindy and announced her uniform was complete. Karen stood back and looked at her handy work, "Oh MY Cindy you are so beautiful you make such a beautiful girl you should have been born one. Curtsy for me...again...yes so very wonderful." Now she moved Cindy to the full length three-way mirror and watched Cindy's face as she saw herself for the very first time as a full girl. Her face lit up, her eyes popped wide open in amazement at how beautiful she was. "Do you like it? Do you like ho beautiful you are Cindy?" "Oh yes Ma'am I do I am so amazed it doesn't even look like me." "Oh I disagree Cindy this is exactly how you do look with some proper care. Do you see how pretty you are and how great you look in that uniform...it means this is how you were meant to be. If you think about it, you look kind of ugly the other way compared to this don't you think so?" "Oh yes Ma'am you are right I didn't look anywhere as nice as I do now did I?" "No Cindy I am afraid not. Now we know what you can look like with a little effort, I think it was well worth it. How does it make you feel?" "Kind of strange, nice but strange. It sort of makes me want to act girly...I don't mean that in a bad way Ms. Karen I just mean it makes me think about all the girls have been observing and wanting to be like them...is that wrong?" "No sweetheart it's not wrong, why would it be wrong. You have learned to relate to women and admire them for their strengths. I admire you very much for theat. That's something very few men can do, they are just not smart enough but you are. With that in mind before we have sex I want to do one more thing to help you see yourself in your true light. Karen led Cindy to the sofa and had her lay over the back of it and then secured her hands and ankles. She got a mirror and laid it on the seat so Cindy could see her face very well. Then she got the penis gag and put it in Cindy's mouth. She began to brush Cindy's dress and petticoats up over her back which Cindy enjoyed immensely. The feelings generated by the petticoats brushing against her nylon clad legs, the bare spot above the nylons and below the panties and the feel of the petticoats against her pantied bottom were marvelous and consuming. The Penis gag resulted in several degrees of deeper submission as designed. Karen left the room and returned a few moments later with a 6.5" strap on attached around her loins! She was sure to show it to Cindy. Upon seeing it Cindy's eyes got very large. "Well I know you have been waiting for this for well over a year my Princess. And now you're going to get to experience fucking with me. Oh honey from the look on your face you seem a little surprised, I hope you are not disappointed. Would you rather I just left you here like this and went to a movie?" Cindy's eyes got even bigger and she shook her head no vigorously. Being left stimulated and tied like this for several hours would have been torture! "Then you do want me to go ahead and fuck like you like you have been dreaming about?" Cindy nodded her head yes. "Good girl. I would have been very disappointed if you would have said otherwise and maybe would have had to go to a bar after the movie and pick up some strange man to have had sex with, would you rather I did that little girl?" Cindy shook her head wildly trying to say no. "Oh did you think you were going to put your little tiny dicklete in me and fuck me?" Cindy nodded her head slowly. "Oh poor baby, don't you see, that's never going to happen. It's way too small for me to possibly enjoy. So is this an acceptable form of sex for you? Will you be happy being fucked this way?" Tears now falling from Cindy's eyes as she resigned to her fate she nodded her head." "Good Girl Cindy, I am sure you're going to like this, I sure do when my boyfriend's do me like this it's amazing to say the least. This statement caught Cindy off guard. He had never had sex with her and thought she was a virgin but now...what was she saying? Karen lubed Cindy up good and was gentle inserting the dildo in Cindy's bottom. After all the greater the pleasure the better the results. She slowly inserted it until it was past all of the sphincter muscles and allowed Cindy to adjust to the size. Then she began to pump the sissy until she was all out fucking him. It was obvious he liked the pleasure and was struggling to climax. "You know Cindy, I just made up my mind. I like this so much that I have decided to allow you to be my full time maid. Isn't that nice darling? You will be dressed like this or in your working maids uniform all the time. Well except when you go to bed or we go shopping. It's going to be so nice having a full time maid. You have just the perfect personality for it. Oh I should ask you your opinion. Do you want to be my full time sissy maid for ever and ever?" Cindy hesitated. "Oh Cindy my little princess, it is so rude to not answer, I will ask you again and if you don't do better, a LOT better with your answer I will leave you like this while I go to a movie and a bar now let's try again. So you want to be my full time sissy maid for ever and ever?" Cindy paused for about 3 seconds and then dejectedly nodded her head yes. Her fate was sealed. I also know you had your hopes up of putting your little penis in me, well think about that Cindy, is that really such a good idea? I don't think it is. All men have penises Cindy, some much bigger than others and many little like yours. Often times they fail to please and satisfy their women and then what? She is disappointed and is not proud of her man. I am proud of you Cindy but what if your little penis failed to satisfy me? I have enjoyed sex with men who had much bigger penises and I enjoyed sex with them very much but I didn't love them like I love you. I just think if you were to put your tiny little penis in me and I was disappointed I may not love you anymore. I may not be proud of you like I am now. Would you really want to risk putting your little penis in me for loosing me?" This all made perfect sense to Cindy and no he did not want to lose what he had. His penis was small, maybe smaller than he thought but he knew it wasn't big. He listened to Karen talking about having sex with men with big cocks and that she enjoyed it. She surely knew better than he how a woman was affected by penis size. He knew like every other man knew, size did matter. He had it pretty good he got lots of sex now which was a new thing for him. She fucked him like a girl and he came like a girl and it felt good. After a bit she unfastened him. "Ok Sweetie, lest see how you do walking in your new heels." Cindy tried to walk but her ankles went side to side. Her but was ticking way out and her head far forward. "Oh my, we do need to have you practice now don't we?" Karen helped Cindy stand straight and then to walk. It was very slow going at first and Cindy was somewhat frustrated but kept at it. Karen kept encouraging her and assisting. Cindy began to make progress, very slowly at first but then faster and soon she was doing pretty good. Karen smiled at her Princess and said, "Pretty fun once you get the hang of it isn't it? I admire a man that can handle all these new things with grace and poise as you are, I am so proud of you honey." "Ms. Karen, I have to tell you I don't feel much a like a man right now and I sure don't look like one. I sort of feel a little uncomfortable about being a man right now." "Well we don't want that because you are certainly a man and heading for the top 10% but let's fix it. Let's pretend you're not a man for now, just for a while and pretend you really are a girl that way it won't be confusing or nagging at your ego. You will eventually learn that your male ego is a negative anyway and this will help. So Ok from now on we will just "pretend" you are a girl and see if that helps." "Oh Ok I guess that would work. But what about work I can't pretend to be a girl at work?" "No...no you can't. Hey you have two weeks' sick leave coming don't you?" "Ya I guess so why?" "Well I'll just call in sick for you on Monday and then the problem is solved. Besides the way we are going to be enjoying sex I don't think you will have the strength to go to work anyway!" "So will I have to pretend to be a girl the whole two weeks then?" "No sweetie, we will just play it by ear. But who knows you may just want to when I start mauling your body for sex...unless of course you don't like sex anymore?" Cindy just smiled. Karen had Cindy walk all over the house, up and down the steps and in and out of rooms opening and closing the doors and practicing a proper curtsy every once in a while. When she was done with that Karen told her that she wanted her to serve her tea. Cindy went to the kitchen and fixed a cup and delivered it to Karen. She curtsied and Karen instructed her to stand with her back to the wall where she was out of the way but could see if Ms. Karen needed anything. She was told to keep her feet together, her head bowed slightly and her hands folded on her apron. She was told to not make a sound or move until directed to do so. Karen enjoyed her tea and a TV show while leaving Cindy as instructed. As Cindy stood there she began to feel extremely submissive. It was if she were an object and was put away until needed. She concentrated on how her pretty new clothes felt and looked and allowed her mind to drift into the submissive things she had been doing at Karen's request. This resulted in strong inferiority feelings. She began to see Karen as larger than life and someone to really look up to. It was a pleasant feeling even the inferiority and submission parts. It somehow appealed to Cindy. She fused in her mind that she didn't want to stand their put away like that but at the same time sought to do exactly what Ms. Karen had commanded. Ms. Karen totally ignored Cindy and even spoke to a few friends on the phone. One for sure was a man and it sounded as though she may have even been flirting with him a bit. That scared Cindy and she instantly vowed to work harder at being a good maid since that was what Ms. Karen really liked, a real man made a good sissy maid and so he would be sure to be the best!!! "Cindy...come here." Cindy approached Ms. Karen and curtsied saying, "Yes Ms. Karen." Cindy I have been thinking that we should use a bell to summon you so I don't have to raise my voice to find you if you are scrubbing the upstairs bathroom floor. I will use this hand bell to do that with. When you hear it I want you to scurry as fast as possible to me for orders, do you understand? "Yes Ma'am." "Cindy we are pretending you are a girl but we both know you're a man and we both know that men have trouble understanding directions. Their smaller brains just don't process information was well as women's brains do so even though we are pretending you are a girl you need to respond like a man until you can developed your abilities to equal those of a girl. So I want you to repeat what I say not just agree to it, OK?" "Yes Ma'am, I am to repeat what you say Ma'am."