Ms. Lisa had never penetrated a male before but of course as a female had been penetrated many times. She knew full well the difference between a gentle penetration and a "dammed to all" forced penetration. She instinctively chose the latter and plunged full into her victim in one solid thrust. Sissy Bunny was not used to this type of penetration as Madam used a gentle persuasion to cause the sissy to like and want to be penetrated. But as soon as the life like and liquid filled balls of the strap on pressed hard against the pansies bottom she pulled nearly all the way out only leaving less than an inch in his body. Then back in she thrust her hard Black cock, then in and out with rapid succession. She next began to talk to him which surprised both of the other ladies.
"Sissy Bunny, I am going to fuck you until your brains leak out your ears. I am going to fuck you all night until I cum a dozen or more times. You are such a pathetic wimp. First you cheat on your wife and then you are forced to be a sissy and suck cock and watch videos of your wife enjoying real men. I loved the video of Burt fucking her while Ted was having her suck his cock. Do you think she has shown that to all of your friends yet or will she wait till you get home to do that and have you dress up like a prissy little French Maid and serve them popcorn and snacks while they all watch it together? Then when they are through maybe you can fluff their big hard Black cocks so she can fuck them again in front of you. I bet you can't wait t for that can you?"
Sissy Bunny was answering her as she asked questions but Ms. Lisa cared not a bit what he had to say she just wanted him to know who was in charge and to feel the power from her hard strap on that was now controlling his entire body and mind. Ms. Lisa threatened him and said, "Sissy Bunny I am going to count to ten and when I say ten if you don't cum like a school girl getting her cherry popped for the first time I am going to use the shocker on you again but three times in a row this time."
Madam Rebecca swallowed hard and Ms. Crystal grabbed Madam's arm as if to say, "What are we to do?" Madam just patted her arm but inside she was worried as a Dom could not go back on an order or a promised punishment without losing credibility. She could only hope Sissy Bunny would climax on command.
Ms. Lisa then increased her thrusts to a spectacular rate, one that only a young woman in full sexual excitement could perform. As she thrust, she counted slowly towards ten. By four Sissy Bunny was thrusting against her thrust trying to get more like a sex-starved woman would. Ms. Lisa said, "That's a very good girl Sissy Bunny, that's the kind of action your wife's Black lovers are going to want and your wife will really enjoy seeing. Maybe I should stop now so you can't cum?" Sissy Bunny pleased, "Oh please, please Ms. Lisa, don't stop, I want you to fuck me, please, harder faster fuck me like a bitch needing fucked, please Ms. Lisa." Sissy Bunny was thrusting as hard as his restraints would permit and Madam was not sure how he could possibly move as much as he was moving but was thoroughly enjoying the de-maleing of this trainee. As Lisa got closer to number ten, Bunny's breathing and straining increased proportionately and when she reached ten she reached down and squeezed her liquid filled balls three times in a row squirting deep into Bunnies sissy bottom and Sissy Bunny exploded in a climax. His climax was so strong that he nearly passed out. It was the most exceptional climax of
his life and he loved the feeling through it drained him completely of emotion and energy. His mouth went completely dry and he was exhausted by the time that Ms. Lisa removed the sissy tamer from his bottom.
Sissy Bunny lay there completely subdued and limp and M. Lisa felt as if she had conquered the world. What a power trip it was for her to make a male climax like he was a woman! She now understood why men liked to fuck so much. Why they liked to make a woman beg or say things they would normally not say. It was not just the pleasure of sex but the power that went with it that women seldom got to experience and share. But now, well now, she knew the secret and she saw the results but it was not over. As she realized all of this she began to cum so she renewed her thrusts into Sissy Bunny as she came over and over. And a strange thing happened as she did this. She heard Sissy Bunny quietly saying, "Oh yes Ms. Lisa it feels so wonderful, thank you Ms. Lisa you are so great I feel so good I understand what you want of me now and I am ready to accept being a sissy and serving my wife and her lovers."
It was now obvious to both Sissy Bunny and Ms. Lisa that Bunny had crossed the line and was now mentally a full sissy. Yes he had a great deal of training to go through but the pleasure he experienced from a completely dominant and controlling woman allowed him to see what his real status was and furthermore, to accept it.
Madam Rebecca knew he was very dry so she suggested Ms. Lisa allow him a drink. Ms. Lisa remembered what madam and said earlier about his feeding and she smiled as she reached for the cock with the tube extending from it and placed it to Sissy Bunny's lips. Without hesitation he licked the end as taught and then opened his mouth and took it in deep. He sucked on it like a cock hungry whore draining as many juices from it as fast as he could while Ms. Lisa held the cock shaft in her hand and watched pleased and amused as he so hungrily sucked it.
She patted him on the head and said, "You make a very pretty cock sucker Sissy Bunny, I bet your wife will be very pleased with how well you suck cock when she has you suck some of her Black lovers for her." Sissy Bunny paused his sucking long enough to say, "Thank you Ms. Lisa, I hope so, I really do want to make her happy." Then he continued taking the shaft into his mouth and sucking on the fake cock.
Ms. Lisa turned and smiled at her mother and Madam Rebecca and said, "This is fun; I could really get into this." Both women smiled back at her and gave her a knowing nod. Madam Rebecca then helped her to start to take off her strap on and Lisa looked disappointed and said, "Oh Madam, don't you have any more sissies that need fucking?"
Madam looked at her with a stern look and said, "No dear, not right now and I don't know how many of them could take what you just dished out anyway. Remember dear this one was and I do mean WAS a hard case. You seem to have resolved that problem but the rest are gentle souls who just need guidance and you need to remember that. We are not in the habit of abusing sissies just for the fun of it you know?"
Ms. Lisa looked disappointed but accepted what Madam had to say. Just then, Sissy Bunny, looked up at Madam and said, "Madam if it please you may I fix my makeup, I look a terrible sight and I want to make sure I am always pretty from now on?"
Madam Smiled at Sissy Bunny and said, "Yes it does please me Bunny, I hope you will continue to along these lines of accepting and improving, it will be far better for you and you will be much happier if you do."
"Yes Ma'am, I know that now. Ms. Lisa has helped to understand that I am here to please and not be selfish as I have been in the past. I am very ashamed at how I have acted in the past as, you know, a man, but I see the error of my ways and I really do think I am ready to really begin making some progress to becoming the good sissy maid cuckold Ms. Elizabeth wants me to become."
Madam smiled back at him saying, "I am very proud of you Bunny and you to Ms. Lisa it seems you have transformed your first sissy though I think we need to work on some of your technique but still it worked very well and you too should be proud of yourself. Sissie, assist Bunny in getting off the bench and move him to the next level of training."
Sissie Curtseyed and replied, "Yes Madam, right away Madam" and provided a respectful curtsey to her. Sissie then with a large smile on his face when to Sissy Bunny and undid his restraints and began to jabber about how much fun it was going to be now that he had advanced and then holding hands took him off toward the vanity to redo his terribly messed up makeup.
It was then off to the next sissy in training for the ladies, Maid Tabitha who was in the kitchen cleaning up.
Across town Ms. Brenda was in route to the seamstress who had agreed to make her Sissy Tammie some new dresses. Tammie was slightly nervous but also was in full anticipation of what was going to happen. Ms. Brenda pulled into the small parking lot next to the shop and they both got out and Tammie followed her across the parking lot and around the corner of the building. Just as they rounded the corner a couple walked their way. Both instantly noticed that Tammie was a man in drag and stared. The man elbowed the woman next to him and said in an audible voice, "Look at that, will you?" Both stared at Tammie as he and Brenda passed them. They entered the door with Tammie carrying the garment bag holding his white communion dress and with his purse hung from his shoulder containing his heels.
They were greeted by
's helper. Katie had been informed as had Linda, Virginia's other helper that a woman was bringing her sissified boyfriend in for measuring for several dresses' one of which was to be his wedding dress but he was not to know so to pretend the dress was not a wedding dress. Both Katie and Linda were anxious to see this situation. All the women had worked on clothes for sissies before but this one was reported to be a little more special and they loved seeing males treated this way. It somehow made things more equal. Katie, Virginia
With excitement in her voice and her eyes darting back and forth between Ms. Brenda and Tammie who was still red faced from the outside encounter with the couple asked, "May I help you?"
"Yes, I am Brenda Moore and this is Tammie, we have an appointment with
to get Tammie measured and pick out some fabrics for some new dresses I want made for him." Virginia
It was obvious to all that there would be no pretending about why they were there. The frankness actually helped calm Katie's nerves a bit and bring her around to doing her job.
She smiled and said, "Yes, we were told to expect you, please follow me and we will get
and get started." Virginia
Brenda had discussed the situation with
Virginiaand was anxious to assist Brenda in her quest for two reasons. First because she liked to see males put in their place and second because she could see this could be a profitable venture if she assisted and helped Brenda sissify her future husband. She knew that Brenda wanted the measuring and subsequent fittings to be done as publicly as possible to expose Tammie as much as practical and Virginia had no problem complying with this request. Virginia
"Hello, you must be Brenda and this must be our little Tammie, I am Virginia, the owner. Shall we go over here and measure Tammie?"
"Yes I am Brenda and this is my future husband Tammie. Tammie brought one of his cute little communion dress to model for you so we can start with a style and build on it so do you want him to model it first and then measure or measure first and then model?"
did not care about what made sense or was most efficient so she smiled and said, "Oh lets have him model it first then we will measure him and then have him model it again so we can see how the measurements we took may affect how the dresses fit." Virginia
Brenda liked the way
thought and she could see the big smiles on Katie and Linda's faces. Tammie knew better than to resist or even to speak unless directly spoken too so stood there in submission listening and getting ready to do what he was told to do. The four women loved seeing a male being so subdued and acting so submissive. His entire stance radiated submission. Standing with eyes down cast, feet together, hands folded in front and purse hanging from his right shoulder. He had a feminine figure resulting from the corset and padded bra as well as the women's pants and blouse he was wearing. He exhibited no masculine traits at all which made the women feel powerful in his subdued presence. Virginia
"Tammie let's get you into your pretty little sissy dress so the ladies can get a good look at you. Make sure you put your heels on and let's see some good turns and mincing so the ladies can get an idea of what they need to do."
"Yes Ma'am, right away Ma'am."
Tammie went to where Ms. Brenda pointed and removed his blouse, pants and shoes to revel that he also had a slip on. All four females intently watched every move he made as he got undressed. Katie made the comment, "What pretty panties you have on Tammie." "Thank your Ma'am."
Ms. Brenda said, "Katie you may be interested to know that Tammie made those panties. Well actually modified them would be more accurate. All the lace and bows that are sewn on were sewn on by Tammie to make his panties more sissy like."
"Very nice job Tammie, they look very good on you and they certainly do make you look more sissy." The ladies all giggled and agreed with Katie.
Tammie was now putting on his petticoat and looked even more feminine than before. The ladies commented on how cute it looked as well and made mention of how nicely it swayed and swished as he moved.
Linda asked, "Tammie do you like your petticoats as much as I like seeing them on you?" Tammie not getting that the ladies were purposely drawing as much attention to his sissification as possible replied honestly, "Yes Ma'am, I very much love the feel of a god petticoat."
"What is it you like so much about the feel," asked
"Oh it just feels so swishy against my nylons. Every time I move or sit I feel it against me and it makes me feel so feminine and submissive. I also enjoy the way it makes my skirts flare out and gives me a more feminine figure."
The women all smiled partly because of how true his words were but also because of how acclimated he was to wearing girls things and the positive way in which he accepted them. Each moment brought more confidence to the three ladies that would be assisting him with making his new dresses as they explored their limits and his reactions.
Tammie was now slipping into his communion dress and approached Ms. Brenda and while turning asked her if she would hook him in the back. She said, "Sure" and fastened up the back of his dress. As she did, she called attention to the two rings at the neck line and the two at the waist line pointing out these should be part of dresses made for Tammie.
Linda asked if they were for ribbons or belts or collars. Brenda replied, "No Linda, if you will note there is a band of heavier fabric that circles the garment at each location as well. The rings are for locks. So I can put a small padlock and make it so Tammie cannot remove the garment unless I want him too."
Katie said, "Is that a problem is he a bad girl some times and won't wear his dresses?"
"No, he actually loves to wear his dresses but it's the idea that I am in control. He has no say so nor is he able to make decisions on his own. This lets him know that I am in charge at all times over all things."
said, "Linda put that in our notes so we don't forget it. Put down "Two locking bands for securing the garment to the sissy one at the waist and one at the collar."" Virginia
Linda giggled at the "sissy" part and Ms. Brenda gave
an approving smile. Ms. Brenda was already quite pleased with the way the staff was treating Tammie and her worries about them being too prudish or not wanting to participate in Tammie's exposure was unfounded. She could see that these ladies were very much enjoying the tormenting of Tammie and would most likely get more creative as time went by. Virginia
Now that Tammie had his dress, petticoats and heels on Ms. Brenda commanded him to walk. The ladies were impressed with how his skirts swayed left and right as he minced so sissy like. His hips were moving in a most feminine manner. They could also hear the swishing of the petticoats as they rubbed back and forth across his nylon-covered legs. Tammie was made to walk back and forth nearly a dozen times before Ms. Brenda told him to display his sitting in a dress. She had him sit and stand over a half dozen times. Next she told him to perform a curtsey to each one of them.
Linda and Katie both had to cover their mouths when Tammie executed his first curtsey before the ladies. It was eloquent they thought, probably much better than either of them could possibly do. They both wondered how many hours he had practiced his curtseys to become so proficient at it.
Just as Tammie was in his second curtsey two customers walked in. The two customers were not just any two customers, no they were
and Jessie Caldwell, the next door neighbors and the ones who had seen Tammie dressed like a sissy before. Tammie had his back to them so did not know who was approaching but Ms. Brenda recognized them right off. She said, "Why hello Alice and Jessie how are you?" Alice
"Why hi Brenda," said Alice and "Hello Ms. Moore," said her daughter Alice as they continued to approach.
Tammie continued through his curtseys and recognizing the voices became red faced. Ms. Brenda noticed this and was ready to exploit it as much as possible. She said, "Tammie you know our neighbors Ms. Alice and Ms. Jessie say hello to them and give them each a proper curtsey as well."
Tammie recalling how Jessie called him a sissy and gave him a look of contempt for wearing feminine apparel was reluctant and embarrassed to turn and face the two as he was sure they did not yet recognize him for whom he was. Jessie had never been referred to as Ms. Before and was still contemplating the elevation of rank from Brenda's remark when Tammie turned and she instantly recognized him. Her mouth flew open and her eyes flared wide and she spouted, "Look Mother, it's the big sissy from our building, look at him he is wearing a dress again."
slightly embarrassed herself by her daughter's outburst tried to calm things down saying, "All right dear, he is just probably trying on a costume for a play or part or something, control yourself young lady." Alice
Ms. Brenda smiled at the innocent actions of the young lady to Tammie and said, "Jessie, you are right he is a big sissy and he is going to stay a sissy. You see dear, we are going to be married soon, as soon as Tammie passes all of his tests and I really don't want to be a housewife so I am training him to be my housewife. Now he can't do a good job at that if he thinks or pretends he is still a man now can he? So I am sissifying him through petticoating and feminization to be a submissive housewife to me. So you see dear he has no choice in the matter and it is I that is making him dress like he is. We are here in fact to have several more dresses made for him, would you like to watch how the ladies go about that?"
Jessie was blank faced and still trying to process all of the information she just heard. Whatever it all meant she was so curious that she definitely wanted to know and see more so she just nodded her head like an android confirming she did. But after doing that she looked over at her mother and pleaded, "Mother may we stay and watch I would really like to watch?"
a little shocked by the events herself but also just as curious as her daughter smiled back at Jessie and nodded her head OK. Alice
Tammie still in shock himself and unsure what to do was standing there amongst all these females, all the females by the way wearing pants and he ironically, the only male, the only one wearing a dress! Ms. Brenda noticing that Tammie had not followed his last order spoke in a louder than normal voice saying, "Tammie, I expect a proper greeting to our neighbors right now!"
Tammie instantly executed a proper curtsey to Ms. Alice and said, "Hello Ms. Alice it is wonderful to see you again." Then to Jessie saying, "Hello Ms. Jessie, it is also wonderful to see you again." Both Alice and Jessie said hello back and smiled broadly at his efforts to obey Ms. Brenda.
keying on the events said, "Ok Tammie let's get you out of your dress, petticoat and slip but leave your high heels on as they affect your posture s we can get your measurements now." Virginia
Normally Katie and/or Linda would assist a patron in undressing from such a garment but all of the ladies really wanted to watch Tammie do it himself. It seemed fascinating watching a male dress and undress in feminine clothing and none of them wanted to miss a second of it.
did look at Brenda giving her a questioned expression and glanced over at Jessie in wonderment of how appropriate this might be for a young lady to attend. But Brenda smiled and nodded her head and mouthed the words, "She will be fine, it's OK really." Alice
Katie did help unlatch the back of Tammie's dress but then stepped back so all could have an unobstructed view of Tammie getting undressed.
As Tammie removed his dress then petticoat and finally his slip Jessie was totally amazed at what she saw. Here was a man, well sort of, that had a pinched waist, full breasts like chest and was fully feminized even down to his frilly, sissy panties. She also noticed something that the older ladies did but were reluctant to mention it. Her youth did not prevent her from asking direct questions as maturity often did.
"Mother did they remove his thing? The boys at school all have big bulges there and he is very smooth like a real girl, did they take it off of him?"
The women all laughed as they knew and remembered all too well how well they noticed the boy's bulges when they were school girls as well. How they would talk privately about them and try and decide how big they must be. It was just too funny that this young lady had the courage to ask such a direct question that each of them, less Brenda of course, wondered about.
Ms. Brenda replied, "No dear he still has his boy things, but he must keep them tucked up inside and back between his legs lest he begins to think he is a man with manly rights. Keeping them tucked helps his feminine appearance as well. You can imagine how unsightly it would be for him to be wearing a tight skirt or skimpy dress and have "things" sticking out. He also must sit to pee like a lady does out of respect so it works out very well."
"Well, doesn't that hurt him?"
"No dear it does not hurt him though it does make it difficult for him to act like man?"
"Well what do you do when you want to have sex with him I mean do you let him out or what?"
"Jessie, what questions from a young lady's mouth," her mother replied in shock.
, these are normal healthy questions and she should get answers to them. Jessie, Tammie is going to be my sissy wife. He won't be doing manly things like sports, or drinking or having sex like a man. His boy things will stay tucked unless he is washing and then they will be placed right back into their proper place. If he has sex, he will have it like a girl. And as for me I have boyfriends who will take care of my needs. You see Jessie. Tammie is not only a sissy but a sissy maid cuckold. Do you know what a cuckold is Jessie?" Alice
"Yes it's a sort of bird."
The ladies laughed and Jessie looked at them strangely not understanding why.
"No Jessie, that's a cuckoo. A cuckold is maried male whose wife enjoys sex with other men, real men, lovers who can please and satisfy her and has no say in the matter at all."
"Really, wow, you mean like you have a harem but it's made up of boys and you get to pick and choose."
They all giggled again and Ms. Brenda smiled and said, "Well sort of but I don't keep them all at the apartment, I just invite one over when I want him and then he goes home when I am done with him. It works out much better that way."