A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !

Sissy Maid Cuckold


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 "Hi...my name is Jennifer Dobson; I am 38 years old, 5' 7" tall and 127 pounds. I have long blond hair and get hit on a lot...by both guys and gals. I was married once to a jerk for 6 years. He lied to me, cheated on me, ignored me and so I divorced him. I got most all of it and he lost all of it including the girlfriend he was cheating on me with! I got the business, a consulting business and began to systematically replace most of the men with talented women and not only is it now a fully woman owned business but it is a fully women operated business. I do have three male employees but you really could not call them men if you know what I mean!

I have a very successful business and am quite busy. I have taken the occasional lover from time to time since my divorce but have them for only one purpose: you got it...sex! Oh, they want more, much more, but I WONT be trampled on by a man again. I will use them on MY terms. Even my male employees are humbled and submissive and I am sure calling me "The Bitch" behind my back. However, I do not really care, its earthier use them or be used by them and I WONT be used by them!

So it was about a year ago when a sweet young male walked into my company applying for a job. He was just 22 and fresh out of business school where he had taken classes on book keeping and accounting. He had never played sports and owned a 1998 Chevy. He was slight of build and 5' 5" tall. His weight was a mere 122 pounds. His hair was longish and his hands soft and unmanly, the perfect kind of "man" for my office.

As I spoke with him and saw that he was quite shy and submissive, I found out he was flat broke and had driven over 300 miles to try to find a job. He did not even have gas or food money left. He was desperate. He told me he would take any position I had and at any salary. I could just feel the power swell inside me, a very vulnerable male at my mercy!

As I spoke to him, I thought back to a woman I had communicated with for years and got to be very close as phone friends. She had to make a trip to my city and told me when she would be there. I offered my home to her but she said that she had "unusual traveling circumstances" and would just rent a suite at one of the five star hotels. She wanted me to come and visit her at her suite, which we would then go to dinner and possibly enjoy some male companions if I was up to it. She was sure from my tastes I would enjoy these men and it would be all her treat!

Hey, what the heck, I was curious, up for some fun, and certainly wanted to finally meet her face to face. When the time arrived, I went to her room and was greeted at the door by a French Maid. I was surprised because she never had mentioned she had a maid or that she had a maid who traveled with her. I did know she was married so was quite curious about her suggestion about some male companionship.

She was more beautiful than I imagined. A drop dead gorgeous brunette same height and build as myself. We both squealed hugging each other and smiling from ear to ear when we met. It was just great actually getting to meet her in person after all the years we had only spoken on the phone. Liz, my friend, asked me what I drank and when I told her she immediately instructed her maid to fetch it, the maid curtseyed and obeyed. I was impressed and asked her about having a maid."

"Oh Jennifer I don't know what I would do without Constance, that's what I call her, that's not her real name but she's my maid so I figure I have the right to call her what I want. She is so obedient and submissive I can tell her to do anything and I do mean anything and she will obey without hesitation."

"So where do you find a maid like that? I mean that's very unusual from what I hear to find a maid so submissive and obedient?"

"Well Jenifer, you don't, you have to train them but done right, training them can be a lot of fun, well at least for the trainer maybe not so much for the trainee," and she laughed.

I looked at her inquisitively, obviously this was some kind of inside joke but she just smiled back, raised her eyebrows and said, "I'll fill you in later. Right now let's have a drink and then go and get some dinner, I am famished."

Constance brought my drink and we chatted about her trip and reason for being in town. She apparently had some real estate she had inherited and was disposing of it. She knew some people around town and would visit with them in the next few days but right now, she was serious about eating, we soon found a restaurant and were ordering.

As we ate, I asked her about her husband, Terrance and if he had stayed home or was away on business. She said, "No he had come with her and I could meet him later." Just then, she received a phone call and interrupted the conversation. She took the call and apparently, from the way she talked she was talking to one of the men she had suggested we have some fun with. She set up a time for him to meet her back at her hotel and then hung up.

"Ok Jennifer that was the guys I was telling you about. I have met them before and they are both studs, and I do mean STUDS! They are real manly men who know how to satisfy a woman without being a problem later on. I hope you're up for it because these guys love sex and are nonstop like the energizer bunny in every way."

I suppose I had a perplexed look on my face, if not I sure felt perplexed! Liz must have sensed it and said, "Look no worries, if you decide you don't like them I'll send them home, no problem. You have to feel comfortable or it won't happen but let me assure you these are fun guys and you will do well to enjoy them."

"Ok," I said, "but what about Terrance, wont that be an issue?"

Liz got a big smile on her face and said, "Jennifer, Terrance is no problem, he is no threat, he can't take care of my needs like a real man can and he knows it and even if he tried to forget I won't let him forget. You know how you talked about using men or being used by them?"


"Well I have been practicing the same believe from many years now and I have totally learned how to use them to my advantage. Do you remember what I said about training a maid?"

"Well sure but..."

"But nothing, Terrance is my maid, he is my sissy maid and my cuckold. I control everything he does and his only purpose in life is to serve and please me, so what do you think about that for using them?"

"What? You are not serious! That's was a girl."

Liz laughed, "Well sort of, he has been turned into a girl and more of a girl than a lot of real girls, but he is still technically a male. Have you ever heard the statement that, you are either part of the solution or you are the problem?"

"Well sure but..."

"There are no buts Jennifer. Have you ever seen a husband that was NOT the problem?"


"I have, Terrance, he was the problem but after training him to be my maid and cuckold he is now part of the solution and no longer a problem. His only purpose on this earth now is to serve and please me and believe me when I tell you he does and he knows it's his only means of happiness as well."

"Well Ok if you say so but I can't say that I understand it all."

"That's ok, you don't have too, just try and enjoy yourself tonight and see if you don't agree with me after you have had a chance to see how this all works, OK, deal?"

"Sure why not."

We went back to the hotel where I kept my eye on Constance, trying to figure things out and see if I could tell he was really a man in drag. I finally concluded that if anything he was TOO feminine. Liz let him know that I knew he was a sissy which caused his face to turn bright red for a while but it also seemed to calm him at the same time. It was about an hour before the men got there and when they did, I was surprised to see they were both Black men. Both very handsome and well muscled very in shape guys and they both had cute smiles and were very pleasant to be around. It was not long before I warmed up to them and was getting interested in more than just looking at them. On top of this, Constance was scurrying around serving everybody and Liz made no bones about Constance being her sissy maid cuckold husband. This only seemed to stimulate the men more and both had obvious hardon's of some considerable size displayed under their now tightening pants!

The men soon began to pair us off and it was William that choose me. He sat down beside me, took my hand, and laid it on his hard cock! I almost came when he did that! The combination of manliness, the sexually aggressive nature, his good looks and smooth manners coupled with the humiliation of Constance was all too much for me. I flushed and looked into his eyes dreamily and submissively like a little school girl, I was embarrassed by my nature but there was nothing I could do about it! He has such an effect on me.

Liz said, "Constance, do you like my choice of lovers tonight?"

"Yes Ma'am he's a very good choice Ma'am."

Everybody laughed at this meek sissified husbands words and could not really believe how submissive and obedient he really was. Of course, our laughter was not missed or appreciated by him and he turned beat red.

Constance ordered her sissy cuckold to approach her and her lover and feel her lovers cock through his pants. You could see Constance's hand shaking as he did as ordered and once he had felt it, she asked him, "Well Constance, is it any bigger than yours?"

"Oh yes Ma'am, it is much bigger than mine Ma'am and you should find it very enjoyable indeed Ma'am."

Once again, there was laughter from throughout the room and Constance got even redder in the face if that was possible!

"Well very good Constance, when he is through you can thank him for satisfying the sexual needs that I have that you are unable to satisfy, will you do that Constance?"

"Yes Ma'am, I will thank him for satisfying your sexual needs Ma'am".

"Very good my little pansy, I would not want him to think we didn't appreciate him."

"Yes Ma'am, I understand Ma'am."

"Ok my little sissy maid go make yourself useful and turn down our beds, I think our lovers are ready for some close attention. And don't get to far away we will both be in need of your talented tongue for clean up duty when they are through."

"Yes Ma'am."

Constance then gave Liz a deep curtsey and scurried off to complete his duties while the rest of us sat there further sexually stimulated by the exchange, anxious to get it on and wondering what she meant exactly by clean up duties with his talented tongue!

Liz explained, "When we are through Constance will come to each of us and use his tongue to clean up any juices that are the result of our activities. You will find this most enjoyable and rewarding. Do not hesitate to take full control over her as she completes this duty. You men may find yourselves extremely stimulated and in need for further release which Constance is trained to provide. You Jennifer will do well to relax and enjoy the cleaning and take control of his head and tell him what to do for best results. I typically like to relax and think about what my lover has just done to me while he cleans me to get the most enjoyment possible, it can be a very rewarding climax if you do it right."

William and I headed to the bedroom where we first embraced in a deep kiss and quickly proceeded to removing each other's clothes. His cock was impressive and I soon was licking and kissing it to his delight. I have enjoyed men with nice cocks before but none that compared to William's cock. It must have been 8" long, very thick and rock hard. He was circumcised which I like and his balls were massive compared to the other men I have been with. I was quite intrigued by the color contrast of my lily-white hands wrapped around his dark meat. It simply excited me is all I can say.

It was not long until I was sucking on his hard Black cock and I could tell he liked it. He had his hands on the back of my head and was soon pumping his cock in and out of my mouth. It did not take very long for him to begin to stiffen, I knew what that meant, and soon loads of thick semen flooded my mouth. I sucked every drop I could and loved the way he took control of my head and his flavor. When I was done, I kissed and licked his cock lovingly and looked up at him to see him smiling proudly down at me. I smiled back and told him it was my turn to which he very much agreed. He lifted me, laid me on the bed and began to caress and kiss me while my hand stayed firmly wrapped around his cock. Soon it began to swell and get hard and that excited me terribly, it was almost as if some magical force was spreading my legs open asking him to fuck me. He sensed my condition and soon was on top of me between my legs. My dripping wet pussy was open and ready to accept his member, which he carefully and slowly slid into me. It was larger than I had ever experienced and it took a little getting used to. The penetration was such a dominating experience making me feel very womanly and submissive to him as he took me. Once he was in, he held it still while taking firm hold of my wrists and stretching me out all while his lips were nibbling at my neck and ear.

After what seemed like an eternity of this he began to move, pumping his hard Black cock in and out of my wet swollen pussy slowly with short strokes at first and as I relaxed he made those strokes longer but still frustratingly slow. When I mumbled for him to go faster he simply placed his lips over mine and silenced me as he continued until I was wiggling and thrashing around trying to get more contact and action. I could feel his control and power and soon I submitted to his tactics. This was what he had been waiting for and this triggered him to fuck me hard and deep. With powerful thrusts that caused his massive balls to slap my ass and as he fucked me furiously, he stretched my arms out as if I were on a rack. I knew very well who was in control, who the man was and what I was and frankly, I loved it, I wanted and needed a real man to pleasure me. Wimps like Constance had no place between my legs with their cocks. Men like my x husband were worthless in bed, he knew it and I knew it but sadly I had not the knowledge or experience to do what Liz had done to Terrance when I was still married to him. Suddenly Terrance was in my mind. Seeing the pathetic wimp of a husband sucking about curtseying, obeying his wife in the most humiliating circumstances. It turned me on even more having William fucking my brains out while thinking about having a sissy maid cuckold for a husband to train and torture and remind him that he was not a real man.

Then it happened, I began to cum. Over and over and over, like never before. It did not stop and soon I could hear screaming, sexual climax screaming and I wondered where it was coming from. Was it Liz? How could she be so loud and open in her sexual expression? Then it began to sound familiar and closer...it was ME! I was cuming and telling the world how great, it felt with abandon. I did not care who heard me, no that is wrong, I wanted everyone to hear me and how great I was being fucked. What made it so good I wondered? Was it William? He was fantastic; there was no doubt about that. Was it the sexually charged situation prior to going to bed with him? No doubt, that contributed to it but then it dawned on me. The real icing on the cake was Constance, the little wimp of a husband all sissified, humbled, and degraded. It was seeing a so- called man put in his real place that was so dammed exciting to me!

William fucked me over and over and over. He did it on my back, on my side, doggy style, sitting on his lap, bent over a chair and more ways than I can remember. My pussy was actually getting sore from his massive hard Black cock but it felt good. Finally, I had to stop. I think he would have gone on forever or maybe longer! However, I could not and I convinced him to stop. As I lay their catching my breath I started to think about what Liz had said about Constance being used for cleanup and other pleasures after the fucking ws done.

"Constance. Constance come here at once!"

Constance appeared and curtseyed to me. Yes, he actually curtsied to ME! I loved it. It felt powerful. I smiled at him standing there in his pretty Black and white French Maids uniform, with its stiff petticoats nylon encased legs and 5" locked on spike open toes heels. I noticed his long pink fingernails and the soft submissive obedient look on his painted face. "Come here Constance and clean me as your Mistress said you should. I want you to take your time and do a very thorough job, do you understand Constance?"

"Yes Ma'am, I understand Ma'am."

He crawled on the bed and lowered his face between my legs; I quivered as I felt the warm wet tongue begin its work. I watched for a moment and then laid back and began to enjoy it. It was truly wonderful. This was a husband who had been trained to pleasure a woman with his tongue not a husband who was doing it just so he could get a blowjob or get his wife off his back. This sissy knew how to lick, suck and kiss a pussy to bring it to life. My mind was spinning with all of the excitement this evening had brought. From the learning of his sissification and cuckoldry to enjoying a fantastic lover, I was primed. However, the feeling of laying there after enjoying sex with a real man to then have a sissified cuckold tenderly suck, kiss, and lick me was extremely erotic and soon I was ready to climax again. I took the sissies head and guided it along with words to bring me to a very enjoyable and satisfying climax unlike any, I had ever experienced. I now understood what Liz meant when she said it could be extremely satisfying. I also recognized that part of it was physical and part of it was mental. Having control over a sissy cuckold was extremely and I do mean extremely erotic. You cannot imagine the power and sensation you get from this as a woman until you have experienced it. It truly is using them for your pleasure and the ultimate in pleasure at that.

As you think about how he is dressed, how he acts and that he is licking and sucking the cum from a real man out of your pussy with his only intent in being to make you happy. There is no selfishness on his part, when you consider this is how real man feels when they sex a woman its powerful, erotic, satisfying, and wonderful. I was addicted to it instantly and kept him there servicing me like this until Liz finally knocked on my door and said that it was time to let Constance do some of his other duties. I giggled and reluctantly said, "OK."

All of these thoughts flooded my mind as I sat there considering the wimp in front of me that had just applied for a job and explained how desperate and vulnerable he was. A wicked thought came into my mind, "Why not I thought, why not?"

"Joel Lynn Adams. Do you mind if I call you Lynn?"

"Ahhh I usually go by Joel Ms. Dobson."

"Do you want a job Lynn?"

"Yes Ma'am, yes I do."

"Well Lynn, a friend of mine, who is very successful by the way, says that when someone works for you, you get to choose what you call them, do you have a problem with that Lynn?"

"Not if it means me getting a job Ms. Dobson."

"Well good Lynn then I guess that means you have a job...but not here I have another location I want you to work at and I don't have time to go into all of it at the moment but I will take you for dinner and then we can talk if you're interested. I think it will meet all of your needs, you will be provided with housing, clothing allowance and food along with pay and I am sure you are more than qualified for the position, are you interested?"

"Yes Ma'am, very interested, I am looking forward to it, thank you Ma'am, I won't let you down."

"I'm sure you won't Lynn, I'm sure you won't. Now wait in the outer office until I am finished and we will go and get something to eat."

Lynn did as told until I was ready to leave. We got in my car, went to a restaurant, and ate then I took him to my house. When we got there, he asked about his car and belongings and I told him we would worry about them tomorrow that he would stay with me tonight. He seemed nervous and uncomfortable so I told him not to worry I would find something for him to wear and for him to go and take a shower then we would talk about his new position. He did as I said and when he was in the shower I opened the door quietly, took all his clothes, and put them in the rubbish.

I found a pair of white panties and pair of women's jeans and a light pink blouse that I thought would fit him. I also put a pair of white socks with a pink design on them and a pair of ladies loafers in there for him and held my breath. Liz and I had talked about Constance many times since I had first met him but did I have what it took to actually sissify a man? I would soon find out.

After a while, I heard the shower stop and after what seemed like an eternity, I heard Lynn call out for me. I went to him and he said he could not wear the clothes I left for him. I asked why and he said he just could not.

I said, "Listen Lynn. You will put them on and get out here or you will be on the street and since I sent your clothes out to be cleaned ,you will be naked now make up your mind and stop stalling and get dressed and let's get on with it, is that clear"?

I had no idea if my authoritarian way would work but I hoped it would. A few minutes later, a very embarrassed and red-faced Lynn emerged.

"I smiled and said, "oh now see you look absolutely wonderful in them, come, come, turn around and let me see." I complimented him on his new clothes and told him he actually looked much better in them than the ones he had been wearing. It was then that I noticed a small bulge in his crotch. He saw me staring and looked at me and got all embarrassed again. I sat down and called him to me.

"Look, I am lending you some of my clothes for now but I can't have you ruining them so we need to fix something." And with that I unsnapped his pants and pulled them down. His little dick was straining against the silk panties from the excitement. I lowered them to his disbelief and shock and told him to spread his legs, which he did without pause. I reached in, worked his little testicles up into his body cavity, then twisted his penis, and pulled back between his legs holding it in place while I got his pretty panties back up to hold his penis where I placed it, then pulled up his jeans. Once he was all back together I said, "there now doesn't that look much better, all smooth and not stretching anything of my clothes out?" I acted as if it was no big deal and just went on with normal conversation.

I doubt that a female had ever touched him and the experience was both embarrassing and exciting to him. Then I reached behind him and between his legs and caressed his half-turned penis. "There now I think you will find certain advantages to wearing things like they are now. I like the way these fit you, look on you and feel. Do you mind if I feel you like this from time to time? It feels nice doesn't it?"

He was flushed and enjoying it. He agreed it was and that he would. I then focused on his blouse, reached up, and caressed his nipples through the blouse stating that it was a bit thin and we had better find something for him to wear under it. I took him by the hand and led him to my bedroom. For young males that have never been treated like this or around a woman's bedroom, the events can be extremely stimulating and they most certainly were to Lynn.

I took him to my dresser, opened my panty drawer, and rummaged around so he could see all of my pretty panties further stimulating him. Then I opened my bra drawer and did the same thing. I found a nice soft pink bra, took it out, and tossed it on the bed. I moved him back to the bed, unbuttoned his blouse, and took it off. My hands worked his chest and nipples for a few seconds and then I picked up the bra and put it on him. He protested feebly and asked why I was putting a bra on him. I explained to him that you are supposed to wear a bra under a blouse and continued to put it on.

It was obvious that he was sexually charged I could have done anything to him. He was still a virgin and had never had sex or sexual contact with a woman. Once the bra and blouse were on, I moved him in front of a mirror and let him see how le looked. Other than the face, it could have been a girl in the mirror and this seemed to excite him even more. Oh, he did not have a perfect hourglass figure or big boobs but the clothes made him look like, well, a country girl in jeans or something.

I got behind him, reached over his right shoulder down inside his blouse and bra, and played with his left nipple. He was paralyzed. The sexual stimulation was something he had never experienced and he was at a loss as how to deal with it except to submit to it. Boys are usually the aggressors and in control but the tables had been flipped on this young male and he was being treated like a girl and finding it quite enjoyable. Had he known what was really going on, what was truly happening to him, he may have resisted but at this point, he was clueless.

"I love the way you look in these clothes Linda, it makes me hot for you. Would you like it if we took this further...sexually I mean?"

"Oh yes Ms. Dobson, I would like that very, very much," he said in a trance like voice. He paid no attention to the fact that I had just addressed him as Linda.

"Good, because I would like to, but you understand there has to be rules, I have to protect myself, you being a man and me being a woman don't you?"

"Yes, I understand".

"Good Linda, as long as you understand and as long as you do what I say then we can have lots fun but if you don't obey me then the fun stops, is that clear Linda?"

"Yes Ms. Dobson."

"Very good. Ok now the first rule is you must remain tucked liked you are now whenever you have panties on, is that clear?"

"Yes Ms. Dobson."

"And you will allow me to touch or caress you any time I want wont you?"

"Oh yes Ms. Dobson anytime, I like that rule Ms. Dobson."

"I'm glad Linda because I am afraid I won't be able to resist touching and caressing you Linda, you are sooo attractive." At this point I moved my other hand down to his ass and then between his legs caressing the head of his penis extracting moans of pleasure from him. He bent forward slightly to provide better access to me reminding me of how a female would respond in the same situation. It was odd for a male to respond this way because their natural response is to bend backward for deeper penetration and more exposure. However, his tail was tucked and he was responding properly because of that.

"Ok Linda here is the next rule. Whenever I tell you to lay across my lap you will do it and put your hands behind you so I can hold them while I play with you. Do you understand that rule Linda?"

"Yes Ms. Dobson, I understand."

"Ok then let's try it right now."

I moved to the bed, sat on it and he lay across my lap. He put his hands behind his back just like he was supposed to and I took hold of them. I spread his legs a bit and rubbed his penis head slow and steady. As I did, I forced his hands a little further up behind him until he winced. I said, "Now I am sure you understand Linda that to get real pleasure you must experience a little pain, don't you?"

Just like a robot he said, "Yes Ms. Dobson, I understand."

"Good Linda but I am not sure you like this or wearing the pretty clothes you have on. Do you like it and them?"

"Oh Yes Ms. Dobson, I like it a lot."

"Well Linda I don't know. I like to know somebody likes something. So if you really do tell me what you like and why or if not I will stop caressing you like this because then I know you don't enjoy it."

"Oh, ah I do like it Ms. Dobson, I like being like this and wearing what I am wearing."

I stopped caressing him but held his wrists tight. "Oh Linda that won't do, that won't do at all. I want to hear the details, why you like it, what is being done and what you are wearing and why and how you want more of it, real details and lots of it or its simply is no fun for me."

"Oh I see what you mean Ok, I love wearing these ladies jeans they fit so nice and make me feel very strange and good and I love wearing your panties Ms. Dobson, I was embarrassed at first but they feel so cool and neat. And I love the way you tucked me and told me to be tucked like that its really great the way it makes me feel and how you can rub me like you are right now..."

I continued to caress him though his jeans bringing him very close but not over the top. I held his wrists and he was very submissive doing whatever I told him to do or say. After he went on and on about how much he liked everything and how good it made him feel I took over.

"Ok Linda we need to talk about your new position. I want you to be my houseboy. You will clean, cook, do laundry, and take care of my house. You will take care of my personal needs; like bathing me, rubbing lotion on me, doing my nails and hair and such, very intimate personal things Linda. In addition, I want you to sleep in my bed, of course, you will have rules to follow and you will have to earn rights but I think it would be nice. You will dress how I say and do what I tell you. Are you interested in that?"

Linda thought a moment and tried to speak but his mouth was dry and he was exhausted from being kept on the brink of a climax for over an hour!

"Really, you will let me sleep with you?"

Is all he could manage to say or think about.

"Yes Linda but only if you follow ALL of the rules, do you understand?"

"Oh yes Ms. Dobson, I do understand I really do and I will obey."

Linda had only dreamed about girls and to be with an older woman who was experienced and beautiful like Ms. Dobson was, well it was still a dream and he could not believe his good luck.

"Ok Linda, let's get you assigned to some tasks, remember you have to earn privileges around here."

I let go of Linda's hands and helped him to his feet. He was quite wobbly and needed to clear his head. I took him to the kitchen and told him I wanted him to sweep the floor and then scrub it on his hands and knees. That if he had any problem he could come to me and I would help him. I retired to the living room and the TV set. When he was finished, he came to me and informed he was done. I got up, inspected his work pointing out any deficiencies, and had him correct them. Then I went back to my chair and had him sit at my feet where I taught him to massage them. I liked the feeling of having him sit on the floor at my feet. It was both stimulating and relaxing. I felt power, real power over a male. I felt like I could make him do anything.

After an hour of him massaging my feet, I told him it was time for bed. When we got in the bedroom, I could tell he was very excited. I turned to him and said, "Now Linda if you do as you are told and obey me completely you will earn rewards. So far, today you have done quite well, some improvements are needed but since it is your first day, I am making allowances and giving rewards liberally. That will not be the case from here on. You will be expected to obey perfectly and show enthusiasm in your duties or no rewards will be given and in fact if you do poorly enough you will be punished, is that perfectly clear Linda?"

"Yes Ms. Dobson, thank you Ms. Dobson."

"Very well then Linda, we will change into our night wear. Since you have none of your own I will share some of mine with you and for being such a good girl I will reward you for wearing what I tell you to wear with your first climax from a woman. Are you ready to obey me?"

I watched his face closely as I told him he was a good "girl" he did not show any difference. I concluded that either he did not actually hear what I was saying because he was focused on getting to cum or that he was accepting whatever I did or said without question. I would explore this further later but for now, there was no apparent disagreement with my words, which was good.

I told him that I would undress and dress him for bed first and then he would do the same to me. I took off his blouse, pants and shoes. I then put a silky short nightgown on him. I noticed him shiver as the filmy material brushed across his skin. It as a shiver of delight and so I acknowledged it, "I think you will enjoy the feel of this material. It feels very sexy and will help us enjoy your climax in a few moments, do you like the way it feels?"

"Yesss Ms. Dobson, it feels very nice."

"And it looks very nice on you, do you like the way it looks Linda?"

This question seemed to embarrass him some but he replied shyly, "Yes, Ms. Dobson it looks nice."

"Good, I am glad you like how it feels and looks because you will wear items like this or similar to bed every night from now on Linda to please me. Remember by accepting the job I offered you your duty is to please and serve me, to agree with what I think and to even accept what I think as your own thoughts. When you can do that you will be on your way to becoming exactly what I want and most importantly need. Do you understand what I am saying Linda?"

"Yes Ms. Dobson I understand what you are saying and I will do my best to be what you want me to be and think how you want me to think. I like what has happened so far very much. This is the most exciting and nicest thing that has ever happened to me in my whole life!"

"I am Glad Linda. Now you must learn to undress and dress me. First, you are NOT to touch my body as you remove or put clothes on me. A good maid never touches her Mistress unless she is told to touch her and then only as directed. You will start with my shoes and then work to my top and then bottom taking things off in layers and folding, hanging or placing them in the laundry as appropriate. Are we clear on this Linda?"

'Yes Ma'am very clear."

"Very well, begin."

Linda carefully removed my shoes and placed them in my shoe rack as gently as I have ever seen anyone handle shoes. This brought a smile to my lips. He then unbuttoned my blouse his hands being ever so close to my breast I could see his fingers tremble. This was likely the closest he had ever been to a woman's breast since he was nursing as a baby! He took my pants down and I heard him gasp as his face was close to my pussy. He adverted his eyes I suppose fearing that I would take him staring as a lack of respect. This too brought a smile to my lips. He then moved to unhook my bra and when my breasts cleared the cups, his mouth opened and a second gasp emerged. I placed my hands under my breasts and lifted them, massaging them in front of him, smiling and saying, "Linda, some day you may be able to earn the right to caress them for me, but for now you have a lot to learn and mileposts to cross. Do you like them?"

"Oh yes Ms. Dobson, they are so beautiful, thank you for allowing me to look at them. I will do whatever you want to be able to touch them. I love them so much Ma'am, they are just gorgeous Ma'am."

"Ok Linda, we will work on that reward but for now please put my night gown on me."

"Yes Ma'am." He carefully put it over my head, pulled out the crumpled up hem, and smoothed it. He then took a step back and his eyes got wide. My nipples were hard and erect and they stood out in the nightgown drawing his attention. My beauty mesmerized him and I giggled inside at how much power I held over this boy.

I sat on the edge of the bed and told him to lie over my lap. I took his hands, pulled them up behind him, and fastened a padded cuff set to his wrists to keep them there. I then placed a padded collar around his neck and fastened the cuffs to the back of the collar to prevent him from getting his hands under his feet and in front of him.

I now had easy access to his panties and his little penis tucked back between his legs with a half turn making the head of it fully exposed. Caressing his little dick through his panties was far more stimulating that though the jeans earlier. I felt it get hard instantly and knew I would have to be careful to take my time and make it last. As I caressed him, I spoke to him.

"Tomorrow Linda I want you to do several things while I am at work. I am only going to tell them to you once and I want you to repeat them back to me after I tell you each one. If you complete them all without any mistakes and each task is done well...I will allow you to suckle my breasts tomorrow night before going to bed. Is that a deal Linda?"

"Oh yes Ma'am, thank you Ma'am."

"Don't thank me until you hear what your tasks are and complete them because any mistakes and you only get to look once again."

"Yes Ma'am."

"Ok the first thing is that I dislike body hair and you have body hair. In the bathroom closet, you will find a bottle of Nair, a hair remover. I want all the hair below your eyebrows removed. Front and back. Read the directions, use it, and be free of hair when I get home tomorrow.

Then I want you dressed, I will lay out your clothes for you. Remember to tuck yourself and to help you stay tucked better I am going to lay out a body briefer for you to wear. I expect you to have it on over your bra and panties and under your other clothes when I arrive home. You can put your bra on by hooking it in the front and then turning it around and pulling it up on your shoulders. Eventually we will teach you how to fasten and unfasten your bra behind you but for now you can do it that way.

I have a book on nails. How to do manicures and paint nails. I will lay that out. I want you to study it so you can take care of my nails, that will be one of your tasks. I will also put some polish and remover out for you to use for practice. You will practice on your nails and that way I can see what progress you have made. You will not be allowed to do mine until you are competent.

You will also make the bed and vacuum the entire house. I am going to train you to be my maid Linda, you will learn to be a perfect ladies maid before I am done with you." As I got to this part, I began to speed up caressing his penis and knew he was close. I began to taunt him and put images in his head hat he would relate to his sexual pleasure causing him to associate them with his release and making him want to repeat them.

"Linda, I like you calling a girl's name and I like to call you a girl. Do you like being called a girls name and a girl Linda?" He did not answer right away so I stopped caressing him. He bucked a little trying to get the feeling going again but my hand was moved. I asked him again and he replied, "Yes Ms. Dobson, I like having a girl's name and being called a girl."

"Very good Linda, your learning. Remember you are to like what I like, want what I want, think what I think and you will get rewards. Do you like wearing girls clothes Linda?"

There was no hesitation this time. He was close and wanted no delays. "Yes I love wearing girls clothes Ms. Dobson." I am sure he could justify these comments by telling himself he was pretending or something but little did he know this would become a routine and eventually it would ring very true in his mind.

"I told you I was going to train you as my maid Linda, do you want to become my trained maid and take care of me intimately?"

"Yes Ms. Dobson I want to be your trained maid."

"What sex is a maid Linda?"

"A female I guess."

"Yes Linda a maid is a girl and girls wear dresses and other frilly clothes. They wear a stiff full petticoat under a maids uniform. They wear a cap, an apron, five inch heels, nylons, and a corset. If you're going to be my maid you will need to wear all of these things as well as make up and nail polish, does that sound like something you can do Linda?"

"yeesss Msss Dobson." He was so very near coming I had to really slow to almost a stop and reduce the pressure on his little dick or he would burst.

"Do you want to cum Linda or should I stop and let you go to sleep?"

"Oh no please Ms. Dobson I want to cum I NEED to cum, you promised me Ms. Dobson, please let me cum please?"

"Well OK if you insist but for me to make that happen I want you to tell me what you will wear as my maid and why you will want to wear it and how it will look on you."

"Yes, Ok I will just rub me please."

"Tell me first then I will rub you Linda."

"I will wear my panties and bra and a petticoat like you said that is stiff and holds out my skirt. I will wear a very pretty maid's uniform like you see them wear in the movies and high heels. I will wear a maid's cap and an apron and make up and nylons and a corset so my waist is small like a real girls waist. I will be your maid and be very happy to be so."

He was so close now, "Will I have to force you to wear the dress or will you gladly do it for me?"

"I I I will Gladly doooo it forrrr you Ma'am."

"What if I decide that you will only wear dresses and skirts from now on forever and I never let you dress like a boy or even wear girls pants again what would you say to that Linda?"

"IIIIIII wooould sayyyy OKKKKK I would wear them like you want".

"Good then starting tomorrow you will wear only dresses from now on Linda and I will make you my sissy maid!"

At that, he burst shooting semen all over his ass. His panties were wet but I continued to caress him easing up but keeping him stimulated so he could not reset his sexual clock. I wanted him to go to sleep feeling the relief but still excited and thinking about what all he agreed to. Once he had completely expelled his load and I had him getting semi hard again, I had him stand up and I changed his panties so he had on dry ones to sleep in. Then I helped him into bed where he slept next to me hands secured behind his back.

He had a somewhat restless night, I suppose due to his hands confined behind him. I did reach down under his nightgown at one point and rubbed him a bit. In the morning, I allowed his hands to go free, took my shower and had him dress me. I think seeing my pussy was a real exciting thing for him. I doubt he had ever seen one before. He was very careful not to touch me and he was breathing very shallow and hard as he put my bra on. Once he had it on I turned to him and said, "Now remember your reward if you do what you are supposed to today." Then I cupped my bra and shook my breast a bit.

I had ordered him to Nair himself so he was going to be awhile before he got dressed but I began to lay out his clothes for the day. I started with a lacey pink matching bra and panty set, followed by a body briefer that I held up and explained to him. It was one with a tight waist and a padded bra, hips and derriere so I thought it would be perfect. I explained how it would hold him in place better than just panties and that he should remember that no bulges were permitted.

I got out a pair of nylons and explained to him how to put them on and a garter belt and went over that with him. Then I got out a white slip and a yellow summer dress. The dress was yellow but had pink and blue flowers on it. I could see by his eyes this was becoming a little overwhelming for him.

"Are you Ok with all of these pretty thinks Linda?"

"Ahh I guess so."

"Well you look a little confused dear."

"It's just..."

"It's just what Linda?"

"It's just that I thought maybe you were just teasing me about wearing a dress."

"Oh no Linda, I would not tease you about a thing like that. I want you to wear dresses for me; I think you will look very pretty in a dress. You looked so cute and sexy in the night gown last night, I just can't wait until your all prettied up and filling your promise about being my sissy maid."

"Whhhhat do you mean sissy maid?"

"Oh well no we didn't talk about being a sissy maid did we? Well you see Linda when a male like you wears girl's clothes they are what is called a sissy. Once you have, worn girls clothes you cannot really ever be a man again and well actually I don think you were ever really, what we would call a real man anyway. Therefore, since you have worn girls clothes and have a girl's name and are going to be my maid you will truly be a real sissy and therefore a sissy maid. You will learn to quickly like it, all the boys who try it do. So this is what you will wear if you want the rewards I promised you or you can get out right now and leave the pretty clothes here. What will it be Linda?"

"But Ms. Dobson, I am a boy and yes I liked what we did yesterday and last night, in fact I liked it a lot but about wearing dresses ALL the time, it's just..."

"Listen you pathetic excuse for a man. Did I not buy you dinner last night and let you wear my clothes and give you the best sex you ever had?"


"I thought you said you wanted to work for me that you wanted to be able to have sex with me, that you would wear what I told you to wear? Were you lying?"


"Well then you better think hard and fast about what you're going to do because you only have two choices and one minute to decide. You can take off what you are wearing and walk out the door right now and live the pathetic life you have been living, no job, no home, no sex and no prospects or you can do what you were told and wear what you were told and enjoy the best of everything. You know what I don't even care what you do and I am not going to wait around to see, I'm leaving and I will see when I return tonight so make up your mind. Bye."

As I walked out, I noticed his eyes welling up with tears. I really did not know what he would do. I do know I liked what I had done and would do it to some other male if this one did not work out!

I stewed over him the rest of the day and went from convincing myself that he would then that he would not. It was driving me crazy and distracting me from my work...not a good thing. I convinced myself he would then that he would not at least a dozen times each. Then I convinced myself that I did not care, ten more times! However, the truth was, I did care, I wanted him to be my pet sissy maid cuckold, I loved the power, the fun, the excitement and I wanted it to happen.

When I parked my car and opened the front door, I had no idea what I would find but there he was. Dressed in the yellow dress and wearing the yellow 4" heels I left out for him. His nails were painted pink and he looked submissive and defeated. He looked at me for a moment and then his eyes welled with tears and he broke out sobbing and fell to my feet kissing them and saying he was sorry.

I took it all in and then told him to stand up. He did and I told him to turn for me and then to turn faster and make his skirt fly out, he did. I pulled him to me, kissed him on the head, and said, "I am very proud of you Linda, you make a very pretty girl and you will make an excellent maid. I am glad you recognize you are a sissy and not a real man and that you like wearing pretty things. Now I want a bath and I want you to run my bath water and then I am going to allow you to wash my body because you have made me happy and proud."

He stopped crying and wiped his tears, his eyes got big, and he smiled and said, "Really Ms. Dobson, you are going to let me wash your body? Oh thank you Ms. Dobson."

He ran the water and bathed me as I commanded him to do so. He was very tender and attentive trying to do a perfect job. I could see the contentment on his face from having such a close association with me. When I got out, he toweled me dry carefully patting and not rubbing as he dried my body. He then helped me dress in my nightwear.

"Very good Linda, you did an excellent job. I am going to give you another treat for being such a good sissy girl. When you lay across my lap tonight and I rub you between your legs we are going to watch a porn video."

His eyes got big but he said nothing. We went to the bedroom and I put on a short video featuring a sissy being humiliated by his Mistress. I set it on loop so it would continue to play while he lay across my lap and had his hands fastened behind him first and then to his collar.

"Linda, I want you to learn what I like and don't like and to train your mind to accept those things for yourself. What that means is that if I like something so will you and if I do not like something you will not either. As my sissy maid you will need to learn to think like me so you can anticipate what I want, need or like. So as we watch videos I will tell you what I like and you will then repeat it saying it as if you liked it. This will help you to learn and be more useful to me, do you understand this?"

"Yes Ma'am, I understand."

"Good girl, now let's watch."

As we did, I played with him stimulating him but not allowing him to climax. The Woman forced her sissy to dress ultra feminine and then to drive to a gas station and pump gas. Others noticed him and she forced him to park down the street and walk several block home in 5" heels and a short skirt where he drew additional attention. I expressed how I liked the way she emasculated him, humiliated him to show how weak and inferior he was and embarrassed him by dressing him in such high heels and a short skirt and exposing him to others. I then had Linda tell me he liked the same thing. I could tell it excited him to have to say those things so I had him repeat it several times. Then I said, "Well if you like what is being done to this little sissy so much I want you to beg me to do it to you."

He hesitated, the reality hitting him of what he was about to do so I stopped massaging him, which he knew what that meant, so he started to beg me to do the things that the video Mistress had done to her sissy. As he talked, I increased the speed and the pressure and he came as he was just finishing begging me to do those things to him.

For the next several nights we viewed different videos, sometimes 3 or 4 night and had worked up to sissies serving Black Masters being fucked and sucking big Black cocks. I would give him his reward as he begged to be the sissy in the video and have the things done to him. What he did not realize is that while it was all fantasy, at least at the moment, he was conditioning himself to understand that wanting these things and pretending he was the sissy in the video brought him immense sexual pleasure. He had technically enslaved himself to these desires without even knowing what was happening.

The next day when I got home from work I told him I had a special treat for him that night but that he had to take the rubbish out for collection the next AM. His eyes got big, this would be the first time he was in public dressed as a sissy but it was time. I said, "Hey you begged me to send you to the gas station and make you pump gas like the sissy in the video, were you lying to me?"

"No, No Ma'am I wasn't lying but..."

"No buts about it missy, you take the rubbish out and by the way there is a bag in there that has your clothes and wallet in it. It is time for you to get rid of your old self and submit to being my sissy. You need to understand that bag is there and agree to get rid of it. I want you to take it out so I know what your commitment is. And I want you to practice your sissy walk, you know, short steps a wiggle and hands limp wristed on your way to and back from the curb. If you go to fast you will make several extra trips."

His face flushed and I could tell his breathing was becoming erratic. However, he did what I wanted. When he came back in I said, "I just love how much of a pansy you are that you obeyed me by throwing away all of your male identity and past, it shows how pussy whipped you are and there is no manliness left in you."

He looked at me and swallowed hard and said, "I just love the way you made me throw away my last reminders of being a man and have turned me into a totally pussy whipped wimp who completely obeys you."

I smiled a huge smile and said, "Perfect, you are becoming a perfect sissy Linda." Knowing he was broken as a man and could not turn back now. I felt myself get wet from the power that I had just experienced. I love it!

That night I put on a Black cock sissy trainer video that showed white sissies being used and abused by Black cocks. Sucking them, getting cum shot on their faces and asses and fucked into submission. As it was playing, he was begging to be a sissy as they were and treated as they were. At one point, a sissy was on his knees with his hands bound behind him sucking a big Black cock. It was a very sexy scene and I knew Linda liked it. I paused the video and asked him if he really liked it and wanted to do it and thinking it was all fantasy I am sure he said he did. I picked up my cell and called William, the Black Man I had fucked and sucked before and asked him how close he was. I had already arranged for him to come over that night and he said he was about 2 minutes away.

Linda heard me talking and said, "What...what are you going to do?"

"Oh sweetie I am not going to do anything but watch, it's you that's going to do something. That was William, the Black man I have talked about in the past; well he'll be here in just a few moment to make your dream come true."

"Whaa, Whaa, Whaat dream is that Ma'am?"

"Your dream of sucking a Black cock like the sissies in the video. You have been begging me for a week to suck a big Black cock and I think it's time I grant your wish."

"BU, BU, BU, BUT I thought it was just a fantasy."

"Well maybe it was when you started out but I want to see you suck a Big Black cock and you do want to please me don't you?"

"Yes but..."

"There are no butt's when it comes to pleasing me Linda, besides you know you really do want to experience Black cocks and I assure you that you will really learn to love them. We will start you out slow and easy by learning to suck them for now but eventually you will leaner to take them in your sweet little tight pussy ass as well. Now don't fear you can see how much all those little white sissies love serving Black cocks, there is no mistaking how much they want them or how much fun they are having with them. So just be a good little girl and do exactly what I say and you will soon be an expert cock sucker! And then later we will let you cum if you do a good job."

Linda was so wound up and the sexual stimulus was so great his mind was spinning. It was not long before William arrived. "Hi darling, glad you come over and help out with this little sissies training."

"Hey I'm glad to help train any white boy to be a girl. They are so much more useful that way than when they are trying to be men!"

"I could not agree more. As you can see this one is not even close to being a man and we have been watching Black cock sissy training videos and he has been begging me to let him suck a Black cock. And of course I thought of you and your wonderful Black cock and wanted to share it with him."

I helped Linda position herself in front of William and then took out his cock and stroked it next to her face. Her hands being secured behind her I thought I should help. I pushed her head close and rubbed his growing cock on her face and pushed the pee opening to her lips and told her to kiss it!

Linda was very nervous but did as I told her to do. Then I said, "Tell Mr. William here what you have been telling me about sucking Black cocks."

Linda looked up wide-eyed into his eyes and then started to tell him how much she wanted to suck Black cocks like the sissies in the videos did. He smiled down at her and asked her many question all set to humiliate and humble the pansy kneeling in front of him. He then told her to beg him, which Linda did without hesitation. "Open your mouth bitch and suck it good and don't you dare spill a drop or I'll beat your lily white sissy ass."

Linda did what she was told and started to take it in. I guided her on how to suck, tease, lick and kiss his manly cock. After about ten minutes, I could tell William wanted to cum and I prepared Linda for his load. William took her head and fucked her mouth like it was a pussy, shooting a large load of hot cum into her throat. She gagged a bit and then I heard sucking sounds as she swallowed the hot load of jisim forever making her a pansy cocksucker. There has to be a moment when this happens that sends impulses through the little sissy's brain notifying every part of his body that any chances of him ever being manly again are gone, that he has crossed over to the submissive feminine side and there is no way back. It seems you can tell this moment by watching the sissy submit and accept what he now is and suck willingly, more willingly than before the cum entered his throat. It is as though he now knows and fully accepts his position and there will be no more attempts to stall or show disgust. He has sucked the Masterful Black cock and there is no going back!

He did perfect especially for his first cock and swallowed all of it. I had him thank Mr. William and then get back over my lap. He was wound tight and ready to burst but I teased him. Then I had Linda beg Mr. William to allow her to suck him again. She did so and William positioned himself so he could stick his hard cock in her mouth while she lay over my lap. I played the video and talked to her telling her how much I liked seeing her with a Black cock in her mouth. How she was as good a cocksucker as the sissies in the video and how she looked just like them. As soon as William shot his second load in her mouth, I brought her to a climax. It was the best one she ever had and it was done while she was sucking a Black cock and dressed like a sissy. I knew this would have a powerful effect on her mind, that she would wish to repeat it over and over. I then pulled William's cock from her perfectly sealed lips and milked out the last of his semen on my sissy's face, in her nose and eyes coating her with the scent of a real man. It was a scent that Linda would be unable to ignore, a scent that would permeate his weak mind and capture his feelings through the power or a real man's pheromones that had just taken control of him.

"Kiss the man's cock little girl, yes kiss it nicely for giving you such a wonderful reward. You looked just like the sissies in the videos, you looked so pretty with a huge Black cock in your lips and I loved the way you suckled on it. Now thank the man for allowing you to suck his cock off and to swallow his semen, thank him nicely Linda."

I continued to caress his little dickette as he said, "William Sir, thank so much for allowing me to suck your manly cock, It tasted so good and was such a pleasure to suck. Your taste is marvelous and I enjoyed it so much, thank you Sir, thank you."

"Well your very welcome little sissy girl. You did well for your first time, I will have to teach you how to deep throat it though. Now let me tell you girl, I will expect you to do as good or better in the future when I come by or bring some of my brothers by to have you suck them. It is good you showed me respect after being allowed to suck me off like that; I would have been offended had you not. I think you should know that Ms. Dobson wants me to train you further in the ways of pleasing a Black Man so in two weeks I will be breaking in your sweat little pussy ass. I tell you that so you can begin to train it to take a big Black cock like mine but that is up to you. Either way my hard cock is going in and the tighter it is the better I like it so it's up to you pussy boy if you prepare or not."

"Linda, I think you need to ask Mr. William to fuck your pussy ass in two weeks and thank him for offering to do so and tell him how you plan to get ready for his fucking you."

"Yessss, yesss, yes Ma'am. Sir, Mr. William, would you please come back in two weeks and fuck my sissy pussy ass, I would love it if you would Sir. I will work hard at getting it ready for you Sir and make sure I am ready to enjoy being fucked by you Sir."

"What a fucking pansy white boy you are Linda. You have no spine at all, you surely are a pussy pansy wimp. It will be my pleasure to fuck your sissy brains out and deposit my loads in your pussy ass and watch you beg and squirm and moan like a little girl as I fuck you. You best do exactly what Ms. Dobson tells you to do and be ready because if you don't or aren't I will beat your ass to a pulp and then drop you off in the middle of the Black part of town in just your panties, bra and heels. You got that white boy?"

"Ye, ye, yes Sir Mr. Williams Sir, I will Sir, I will do as you want Sir."

Both Jennifer and William laughed as Ms. Dobson stroked the pansy and brought him to a third climax. Linda was defeated, humiliated and humbled. He felt totally owned, controlled, and submissive. He could smell the man scent left on his face and taste the cum that had entered his mouth and gone down his throat. He felt different. He felt that he had done what he was supposed to, that he had accomplished what was expected of him and in some way, he was proud of that. Proud that he had sucked a Black cock off and swallowed the cum, almost like he wanted to scream out that he had done it and tell the world. Yet he also knew it had changed him. He felt his dickette get smaller and his marble sized testicles shrink even more. He felt more feminine.

After William left I put Linda over my lap once more and told him how much I liked the way William treated and used him. How much of a wimp it made him and how I enjoyed thinking about what was going to happen in two weeks. I told Linda to beg me to make that happen and to tell me how good it would feel. Linda being totally subjugated at this point did as told and as she got deep into begging to have it done, I took the sissy over the top and had him cum for the fourth time that night, cumming while thinking about and begging for a Black Man to fuck his virgin sissy ass. This would have excellent mental effects on my pussy whipped sissy boy.

The pansy was very overwhelmed by all the power around him and was not ready to say no or challenge anything being said or done to him. I was amazed at how submissive he actually was. I found it hard to believe any male would allow such total degradation of himself without even a whimper. I kept him over my lap and asked him if he understood how we would get his pussy ass ready for Williams cock.

"Yes Ma'am, I think you will use butt plugs and dildos to stretch me, is that right Ma'am?"

"Very good Linda, I see you have been paying close attention to the videos we have been watching. I want you to get up, cleaned up, and get dressed while I dress and were going to take a ride to an adult toy store and get you what you need. You don't have any time to lose if you're going to be taking Williams big cock in your pussy ass in two weeks!"

We got ready and nervous as he was he got in the passenger side of my car and I drove across town to an adult toy store. I was surprised to see a woman running the cash register. I had only been in one or two of these previously and it had been a long time ago. It had a lot more DVD's and fewer magazines than what I remembered and a huge selection of clothes and toys, especially phallus type toys!

I figured, "what the hell" and approached the girl behind the counter with sissy boy in tow. It was obvious he was a sissy, just light makeup and no wig but his hair was longish but still styled more like a man's cut than a woman's. She saw him next to me and smiled a knowing smile.

"Hi, we need some help. My Black boyfriend just made my sissy here suck his cock tonight. The sissy did a good job and swallowed it all." The girl looked at him, raised her eyebrows, and nodded her head in approval.

"And in fact he actually sucked him off twice and thanked him for the opportunity. But My Black lover wants to fuck this sissy's pussy ass in two weeks and he's still a virgin, what do you suggest to get him ready?"

"Ok, well, is your lover well hung?"

"Oh yes he's got a very nice cock, both long and thick."

"Ok so we'll need to stretch you sissy out pretty good or it's going to hurt him. Do you want him hurt and if so how much?"

"I would prefer that he enjoy it. I am causing him to enjoy being a sissy, sucking cock and enjoying being fucked would be helpful to his mental state if you know what I mean."

She laughed and assured me that she understood what I meant and then said, "You want him to crave Black dick don't you?"

I smiled and nodded my head in affirmation.

"Ok, then I guess what you need is a pack of five butt plugs. They start small and end up huge. The way to use them is to lube them up good and his hole as well. Always start with the smallest even after he is used to them. Push it in and allow him to relax. Then pump it in and out several times until he relaxes and accepts taking it easy, you will be able to tell when he does. Then remove it and instantly use the next bigger size. It helps if you warm them to body temperature and always use a lot of lube. I recommend this lube here. Ok but now, you also need to get him used to dildos. I would imagine you will eventually want to peg him. You know, in the last two years we have had more women ask about pegging then in all the years prior. I guess more and more women are understanding the power of the cock and using it on their men or well in your case your sissy to subjugate them and train them to be obedient and submissive, nothing like a hard cock to do that, now is there?"

"Well I know how well they work on me so I suppose it's similar for sissies or males."

"Yes maybe even more so. Nevertheless, here I would recommend you get two sizes. This white one about 6" long and not to thick, it vibrates and is a good starter and then this Black one which is 8.5" long, much thicker and not only vibrates but wiggles around and even retracts ad thrusts a bit. I have one myself and it is as close to the real thing as you can get. You can get a harness for you to wear and use it on him and you can get a harness that fastens it in him and you can insert it and let it run. So sissy boy how did you like sucking your first cock?"

Linda was mortified, a direct question from a stranger. He froze and did not answer, his mouth was moving but nothing was coming out. His eyes were flared and his face beat red!

"Answer the nice lady Linda or you will be walking home."

"Ah Oh, ah, I, I ,Oh I I guess It was ok."

"Just ok? Come on sissy girl Linda, I am sure you loved it. I loved my first cock so tell me really how did you like it?"

Linda turned even redder if that was possible. "I liked it I mean it was good, I enjoyed it."

"I bet you did, how did it feel when he shot his load in your mouth? Did you like the taste?"

"It surprised me when it happened I mean I knew it was going to happen but it surprised me when it actually did. I was scared I wouldn't like it but I did and I swallowed all of it didn't I Ms. Dobson?"

"Yes you did sweetie, you were a very good girl. Tell her about what I did with his cock after you sucked him off the second time".

"Ms. Dobson took his cock out of my mouth and milked out the last of his cum and spread it all over my face, in my nose and in my eyes."

The girl leaned forward and sniffed the air, "yes I can actually smell his cum on you. Nice, I like that. You sure are pussy whipped aren't you Linda?" And she laughed.

"Yes Ma'am I am."

"Well good I am sure you make a much better sissy girl than you did a man. At least now your owner can benefit from you."

"Yes ma'am," Linda replied and hung his head.

"If you would like we can go in the back room and insert the smallest plug and that way he can wear it home and will be ready for the next size bigger when you get there."

Linda started to hyperventilate at the sales clerk's suggestion but I loved the idea and agreed to it immediately. In the back, we had Linda bend over a table, raised his skirt and petticoat, unsnapped the crotch of his body briefer and lowered his panties.

"Oh my he is so tiny, even for a white guy he is tiny, you certainly made the right choice on what to do with him, think of how frustrating that thing would be to deal with a s a woman?"

I smiled and said, "Yes I know I did and he is learning so fast. When I get done with him I plan to use him as my full time sissy amid cuckold."

"I think that's a perfect idea ad a perfect use of a pansy like this."

We lubed up the butt plug and his hole and inserted it. Linda gave out a slight gasp as it went in and was proud of how he took it. Little did he know it that the smallest plug did insert very easy and the next size up was not to bad either but the middle size, well that was different story, that would take some effort and getting used to.

The clerk said, "I see you keep him in a body briefer, that's good because it will make sure his plugs stay in. Panties don't always offer enough support to keep it in but the body briefer will and most likely you won't need to make him wear the harness if he has the body briefer on."

"Thank you for all your help, you have been wonderful."

"Well thanks for coming in and come back often, you don't have to buy anything I just want to see how the sissy is progressing. Maybe next time there will be other customers in the store and he can tell his story so they can all hear it. Wont that be fun?"

"It certainly sounds like fun, don't you think so little sissy girl?"

"Yes Ma'am."

We both laughed.

When we got home the first thing I did was to put pansy over my lap and change out his butt plug. The second one went in quite easily and I was impressed with the progress he had made so far. However, I was not under any delusions that future progress would come at a slower rate.

The next morning I had Linda lay over my lap while I worked the second sized plug in and out until he was relaxed and then replaced it with the middle or third size. This took some effort but it was in and I snapped him up and told him to have fun wearing it while I was gone. I explained to him that at noon I wanted him to take a photo of the plug still in with the cell phone and send it to me. He did and I texted him back to take it out. He told me latter this was not such an easy task for him but it felt good to have it out.

That night we watched more video of Black men fucking white sissy boys and I had him beg me over and over to male him do the same thing. I then put the second plug in and got him loose followed it with the third plug and brought him to climax with him begging Mr. William to fuck his sissy ass with his big hard Black cock. We repeated this same scenario for the next two weeks working up to the forth plug. I would get so worked up listening to him, watching the videos and thinking about what was going to take place that I would end up making him eat my pussy for an hour sometimes getting me of over and over.

I felt he was ready mentally and physically by the time, the two weeks were up. William had stopped by four or five times during that period and each time; Linda serviced his cock with his mouth. The difference was now that Linda was allowed to have his hands free, which made it so he could lower Mr. Williams's zipper, reach in and pull out the Black Man's cock. They both seemed to like this better and so did I. I would usually finger myself while watching my sissies mouth fill with cock, then listen to the unmistakable sounds of swallowing cum and then to smell the man scent as I would cover his made up face with man cum!

William would ask Linda for progress reports about his pussy ass and remind him he would be taking it ready or not soon.

When the big night came, I arranged for Nancy, the clerk at the adult toy store to come over and watch. She brought a female friend with her as well named Jody. William arrived and Linda was tied over a stuffed chair. His ankles tied to the chairs legs in the back and his wrists tied to the chairs legs in the front. His panties had been removed but he was still wearing all of his other girl clothes.

William approached his face and slapped his face with his massive Black cock until it got hard and then told her to suck it and get it wet. Linda did as ordered while the rest of us watched the show. When William was ready he move around to her rear and pulled out the size 4 Butt plug and pushed his large cock into Linda's gaping hole. He got it started ad then steadily pushed it until it had passed his sphincter muscles and was deep in the sissy's ass. He just held it there while Linda squirmed a bit trying to get comfortable. Then he slapped her sissy ass and began to move his cock in and out. Slow and methodically he moved. He would go into until his balls were pushed against the pansy lily-white ass and then wiggle it. Linda would moan each time he did this. Then he asked her if she wanted it.

"Oh Yes Mr. William I want it, please fuck me Sir, please."

"I want you to call me Master, Linda. I want you to beg me to fuck your sissy pussy ass or I will just let you hang and not cum and Ms. Dobson will leave you like this until tomorrow so you better do a good job and be a very good little girl. Do you understand you pathetic white sissy?"

"Yes Sir, Yes Sir Master William I do understand I do. Please Master William, Please Sir fuck my sissy pussy ass and make me your bitch. Please Master I need to feel your big hard man cock in my ass fucking my sissy brains out. Oh Sir it feels so good oh please Sir fuck me , fuck me over and over Sir, I want you to take me and treat me like a sissy bitch Sir. I am here for your pleasure Master, please use me with your cock and put me in my place, show me you are the Master and I am the sissy, Please Sir. I need your cock to fuck my sissy brains out..." And the begging went on and on.

Linda had zero pride left. He had become a wanton slut destined to obey his owner and anyone she lent him too. We females were all fingering ourselves as we watched the Masterful Black man totally dominate the sissy white wimp. We all loved it. It was a total turn on for us to see a real man's power and pretend mans lack of masculinity.

After some time William shot a load into the sissy's ass, which almost caused the pansy to climax but not quite. William took his time and got it back in motion and built up to a second climax. This time however, Linda was ready to cum, to cum from a serious fucking and not any other means. As her climax built it was like that of a real woman. Slow and deep and mounting, she feared he would stop just a moment too soon so begged him not to stop and to fuck her faster and harder and finally her climax triggered and she came like a real woman would. Screaming, moaning, and convulsing repeatedly. Taking it in as if a real female would and feeling his hot sticky cum deep in her bowels. She felt vindicated. It was by far the best climax Linda had ever experienced. She came and came and came and finally she was cuming so much and for so long she stared laughing and cuming at the same time. Then she begged him to stop but he was ready for a third climax and would not until he did. This triggered Linda again and she came once again the powerful manner that women climax in. She just collapsed and lay over the chair while William pulled out letting cum drip don the sissy's white ass.

"How did you enjoy it sissy dear?"

"Oh...Ma'am...it was wonderful, just simply wonderful." She said with dreamy eyes and a dreamier vice. All the girls laughed, as they knew exactly how he felt and what he meant. They all knew that he was now totally addicted to being a feminine play toy and slave. They were impressed, pleased, happy and excited about the prospects.

The aftermath!

Linda never got to lay over Ms. Dobson's lap and have her clit played with again. No, Ms, Dobson used her strap on to control and satisfy the sissy girls desires. She molded her into the perfect sissy maid cuckold and began to enjoy William and other Black lovers in her bed having Linda prepare their massive cocks before sex and to clean them after. Linda got her fill of hard Black cocks in her pussy ass as well and learned to love every moment of her new life as a submissive girl. It was the right choice for both of them. Eventually Ms. Dobson invited the other three males who worked for her to her to her home for dinner and now all of them work full time as females. Totally emasculated and feminized even having gone so far as to give them breast implants to fill her desire for an all women company. Her motto was, "No sense in letting a little masculinity get in the way of female dominance and unity."

So the next time you're walking down the street, eating in a restaurant or conducting business n a Woman owned facility, you just might be talking to or looking at a sissy!