Sunday, October 4, 2009

sissy robert - part 2

An interesting weekend
At the end of the week, the weekend finally came. Once again Robert was dressed totally in women’s attire. He was wearing a peach colored sissy dress with matching 4” high heeled sandals. My sissy girlfriend tricia and I were in our French maid outfits and cleaning the house while Mistress and robert lounged around. Mistress called over her two sissy maids and had us unzip each others dress. We knew what was coming. Mistress undid our corsets and pulled each of them in tighter and tighter, so we could hardly breathe. I thought I was going to faint, but was afraid to do so. Mistress ordered us to bring her a glass of wine and pink lemonade for Robert. She sat on the sofa and ordered sissy robert to sit next to her. Robert adjusted his skirt and petticoat just like a girl as he sat down next to his Mistress.

Sissy tricia and I were standing there in front of Mistress Gypsy as ordered. We were both in lingerie and high heels. I wore black ruffled panties, a bra, a very tightly laced corset with eight garters, black seamed stockings, and 5’ black stiletto heels. Tricia wore identical attire, but all in white. Mistress began, “Now sissy Robert, I want you to see that I treat you differently from my other sissies. You are my pet, but sissy gina and sissy tricia have been trained to be maids and sissy queers.” She looked away from Robert and towards us and said, “Alright no my little transvestite fairy boys, start kissing and caressing each other erotically. And do it with feeling. I know that won’t take much, but I want you to show robert what little sissy faggots you have become.” With that tricia and I started kissing each other passionately and caressing each others’ lingerie clad body. “See this now robert? Look closely at gina and tricia. You know they are also males like you. Look at how passionately they kiss? They are real fairies.” Turning her head towards us once again, Mistress ordered, “Come over here my little sissy boys.”

We did as we were ordered and both curtsied as we approached. Mistress pulled us each close and one by one and pulled down our ruffled panties. Robert saw that we were each wearing a chastity device like he wore. But then Mistress pulled out a key and unlocked both tricia and I. All three of us sissies were surprised. Mistress ordered us again, “Alright sissy boys, continue kissing and caressing.” We did so right in front of robert and Mistress. It soon became apparent that all this sexy caressing of my sissy friend and his lingerie clad body was making me have an erotic effect and I was getting an erection of my little sissy clitty. Likewise, this was having a similar effect on sissy tricia. Mistress clapped with glee, and said to robert, “See your sissy friends are getting sexually excited by each other. I’ve trained these sissy boys differently than you. I have had them living together and they sleep together in a single bed, very close. They are not allowed to have sexual release unless I say, and when I say so, they get sexual release only with each other. I have been directing how and when they do this. I have been training them this way. This has been going on for two years and they’re now at a point of sexual intimacy on a regular basis. These two males, I have turned into transvestite sissy queers. Isn’t that right boys?” Without stopping our kissing and caressing, tricia and I replied, “Yes Mistress.” This little escapade stopped shortly thereafter without either my sissy girlfriend or I getting any sexual release. We were so horny and frustrated. We were used to putting on sexual shows for Mistress on a regular basis. Even so, it was a bit humiliating dong it in front of another sissy boy. We were put back into our French maid outfits and sent back to work. Mistress showed this to differentiate the kinds of sissies that we were.

Back to work

Week four: Mistress accelerated robert’s program further. This week he wore some new blouses that Mistress bought for him. The sleeves had ruffles. They were becoming much more feminine than in the beginning. And now she had him wear a touch of light pink lipstick, eyeliner, and some flowery perfume. He was wearing 2’ high heels with a thinner heel, making the look much more feminine. As in the past, Robert seemed to be embarrassed and by the progressively more feminine attire he was to wear each week. Each week it ended the same way. Robert followed the logical arguments and coaxing of his dominant Mistress. By mid week, his male co-workers were starting to ask Robert, “What gives Robert? What’s with this girly stuff? Are you becoming some kind of a sissy or something?” Robert innocently responded, “What stuff?” Ed, a co-worker said, “You’re wearing a woman’s blouse, high heels and make-up. Are you gay?” Robert blushed and said, “No I’m not”. Ed just said, “Suit yourself man,” and walked away. None of his co-workers would go to lunch with him anymore and he became a bit isolated. However, one young woman said, “I think you look cute robert.”

Week five came and now Robert was wearing clear nail polish and his already noticeably long nails. He was also wearing a camisole under all his blouses. With some of the blouses it was noticeable if you looked close. All the women noticed and did look close. His lipstick was a bit darker pink this week, and in addition to a heavier eye liner than last week, he wore a little pink blush. His progressively feminine look was the talk of the office. They all waited to see what was next. The boss was getting a bit annoyed with Robert. This young man had shown such potential and now he was looking feminine and decidedly unprofessional for a man. The clothing also accentuated the fact that Robert had been gradually adopting some decidedly feminine mannerisms. He looked like a swishy gay guy. But what was worse was the fact that the clothing he wore was obviously not men’s clothing. His short mannish hair style and somewhat masculine face continued to provide contrast to his feminine attire. At the end of the week, robert’s boss came in to talk to him. “Son, I don’t approve of this new look. It has got to stop. Do you understand? Robert meekly replied, Yes sir”

That night Robert told Mistress about his boss’ comments. “Mistress, I am worried. You said no one would notice. Everyone is talking about how I dress at work and my boss vehemently disapproves.” Mistress told him they would talk about it later. All that weekend, Mistress had Robert so occupied with feminine activities while wearing the cutest and feminine dresses. When Monday morning come, robert’s clothing for the day was laid out. “Roberts immediately came to see Mistress Gypsy. “Mistress, I can’t wear this. It is even more feminine than before, and my boss already disapproves.”

“Now, now sissy boy.” Mistress said in her soft soothing voice. “Your boss has no power to do anything about this. He is just blowing smoke. By wearing this you will show you are in the right and not backing down. He will make a few bold comments after which he will throw up his hands in disgust, go back to his office, and nothing more will be said. Trust me sweetie, I know how this works.” This sounded logical to Robert, but most things from Mistress Gypsy now did anyway. He still had doubts. But he had to make a choice. Who would he listen to, his boss, or Mistress Gypsy? He did as he was told by the dominant women who controlled his life everyday.

Week six, a big week
Robert walked into work dressed in a new outfit that Mistress had secretly purchased. Robert wore a bight pink pant suit with a white shell top beneath. He also wore nude colored hose attached to his tightly laced white corset. In addition he wore a white camisole and pink panties. His nails were painted bright pink and his make-up was done with pink lipstick, eye shallow, blush, and eyeliner. His make-up was a bit over done and created a stark contrast on his masculine face. He wore feminine jewelry, pierced earrings, and rings on his fingers. To top it off Robert wore 3 ½” high heels in pink to match his pink pantsuit. This all contrasted to the fact that Robert still did not wear a bra to work and his hair was in a man’s crew cut style with slight sideburns. He was flaunting the fact that he was a feminized male. The office chatter was intense. When word started getting around, all the women showed up at his cubicle to look at him. Many, mainly the women, thought he was cute and told him so. This really boosted his ego. The guys continued to make tacky comments and called him Roberta. He could hear them talking about him in the background and using words like sissy and faggot a lot. Ed said, “I remember when you were a real stud with the women, robert. You have really gone off the deep end. You look like a fairy. You’ve turned into a real queer.” After all the cutesy comments from the women, this was and unexpected blow from a former friend. He ran off to the men’s room and locked himself in the far stall to gain his composure. After a few minutes he came out somewhat more composed. As he was coming out of the stall, his 3 ½” stilleto high heeled shoes made a distinctive click click on the tile floor, a sound no one expected in the men’s room. But there was robert’s boss peeing at the urinal, when his attention was taken by the sound of the clicking high heels. His boss said, “What the hell? I thought I told you I didn’t want any more of this?” Robert said quietly, “Yes sir.” The boss turned around and finished his business, ignoring the sissified young lad. Robert left and went back to his cubicle in joy. It was like Mistress said. His boss would get huffy and then just throw up his hands and ignore it. He had won. He had won despite the fact that he didn’t have total confidence in what Mistress had told him.

An hour later a phone call came from the human resource (HR) office. He wondered what this was about. When he got there, he was told he was fired for disobedience and unprofessional conduct. The order came from his boss but he would have nothing further to do with the sissy boy. The woman in HR said, “I am sorry but I can’t do anything about it. You will need to leave immediately.” Robert was shocked and got up to leave. As he was leaving, the HR woman said, “By the way, I like your shoes.” Robert packed up his few things and went home to Mistress’ residence.

Back at home
When robert told Mistress Gypsy about his getting fired, she was very sympathetic and consoling. However, underneath she was laughing with glee because this was her plan all the time. She knew that if she could push Robert enough, he would go over the acceptable limits and get fired. She was delighted. He no longer had a job. He was totally dependent upon her. She had robert change into one of his pink sissy dresses and 5” heels. “Dress up pretty now robert and it will help you feel better,” she said. He did as he was told. But he was determined he would look for another job. He would fix this problem, and he was going to get another job as a male. Little did he know that Mistress was going to keep him so intensely feminized, that it will be difficult for him to get another job, especially since he said he wanted to go back to work as a male.

Mistress gently tugged the sissy boy to the computer. He walked slowly in his 5” heels and his petticoats swished as he walked in his frilly sissy dress. Mistress clicked a computer file and said, “Look here robert, you can’t go back to work as a male. You shredded all your male underwear and your male clothes have all been given away. Don’t you remember this video? Don’t you remember the declaration you made at the shoe store? You said, ‘Yes I want to wear women’s clothing all the time.’ Face it sissy boy, you are stuck. You are totally dependent upon me. But I want you to stay here with me. I want you to be my sissy pet. Do you understand?” Robert was shocked with disbelief. He really was stuck. All he could utter is a “Yes Mistress, I understand.”

Mistress now gave her edict, “Now, from now on my sissy pet there will be no more women’s slacks or pant suits. Your male attire is all gone forever, and after you changed into that sissy dress, sissy gina collected all you women’s office attire and took them to a resale shop. You are to dress and appear exactly as I desire. From now on you will live totally in sissy dresses and high heels. Now you have two choices. First, you can leave, but with only our high heels, sissy dresses, and lingerie since those are the only clothes you have to wear now. Your second choice is to stay here and agree to my total and unconditional domination. If you select the latter choice you will get on your knees at my feet while sissy gina films you begging me to take you, and your begging better be good or I’ll kick you out. What’s it going to be my little transvestite sissy boy? Decide now.”

Robert was in a quandary. He was lost. He didn’t know what to do. He didn’t know how he could cope as a sissified male if he left. Mistress’ offer was a safe bet, bet he felt so humiliated to be treated like this. He was scared and thought for a long minute. Then he got down on his knees and began to speak as sissy gina started the video, “Oh most esteemed Mistress, I can’t help myself, I am weak. I know that I am a sissy. I confess that I am a transvestite who enjoys wearing women’s clothing and that it is a real sexual turn on for me. Please, dear Mistress, I beg of you to not cast me out. I like being a sissy and I crave it. I thank you for taking me from a stud male to an effeminate sissified male. I want to continue. I beg of you, let me continue. I will do anything you ask” By now robert’s humiliation was intense and his desires were genuine. The humiliation he felt was so degrading that he, as a male in sissy dresses, should be begging to be kept this way. He internally acknowledged the degradation and knew he shouldn’t like it, but he did. He liked it a lot. The humiliation, however degrading, was giving him an emotional high. He felt sexual stirrings too, but his chastity device kept him in check. This was sexually stimulating and the emotional feelings intensified as he spoke. “Continue,” demanded Mistress Gypsy. “Dear Mistress, I beg of you to continue to turn this lowly male into an effeminate little pansy. Sissify me to the hilt. Dominate me and keep me for your pleasure. I don’t want to have sex with women any more. I want to be kept in sissy dresses and shown off to the world so that everyone knows what a sissy robert Johnson really is. I accept that you will post pictures of me as a sissified male all over the internet. I know this need to be done to totally break my male ego. I beg of you to continue my training and feminization and that I may be allowed to serve you and please you.” Afterwards he curtsied.

“Not bad sissy robert. I’ll keep you because this is what I wanted all along. In the past, my sissies took hormones, wore wigs and got a lot of confidence as girls. They all eventually left me. But that is not for you. You will always be a sissified male. You will never be allowed to totally pass as a woman. You will wear absurdly feminine attire to attract attention and you will never wear a wig or long hair. I will see that you are the biggest fairy around and you will continue to beg for that priviledge. From now on you will be displayed all over the internet so everyone can see you, my prissy sissy male, and they will see my dominance over you. I will continue to humiliate you to keep your silly male ego in check. You will confess all your erotic sissy desires in a well publicized blog. Before long you will be the biggest prancing transvestite sissy around.”

Unlike tricia and I, robert no longer has a job. He lives a life of spoiled indulgence somewhat like a lap dog. Robert has long since had all his male clothes taken away He now only wears dresses or skirts and is not allowed to wear any pants, ever, not even women's pants. Robert wears only sissy dresses and skirts with an occasional frilly maid's outfit. All his clothes have lots of lace, ribbons, and bows, and nearly every outfit is worn with frilly petticoats. All his panties are silky and have rows of ruffles. He always wears a bra, much like a training bra, but one that is not padded. Sissy robert is now only allowed to wear high heels that have at least 3” heels. In fact he very often must wear 5” high heels. Mistress Gypsy wants robert’s leg muscles to get so used to wearing heels, that he is uncomfortable in flats. His fingernails and toe nails are always painted pink and he is never allowed to wear a wig. In fact, his hair is cut quite short in a crew cut with slight side burns, an obviously male style. This, with his somewhat masculine face is insurance that he is recognized to be a male at all times. Mistress also decided not to give him a femme name so he would always be reminded he was a sissified male, and others would be as well.

Since tricia and I do the housework and the serving, robert only does light chores and serves Mistress when we were busy with work or other service duties. Mistress likes to have robert sit near her when she reads, watches television or works on the computer. He is often encouraged to put his head on Mistress' lap and occasionally allowed to nuzzle up to her breasts. Mistress knows this will makes the young man horny and enjoys teasing him for long periods of time. Robert was kept in chastity so he has no way of releasing his sexual frustration. This is what Mistress wanted. She enjoys dominating him this way, keeping him so sexually aroused. "You like being a guy wearing dresses, don't you sissy boy?" Robert would sometimes answer meekly, "Yes Mistress." This would displease Mistress Gypsy. Immediately she would order sissy robert to bend over her knees and she would slide down his ruffled panties and proceed to spank him until he cries like a little girl. Furthermore, the young panty-clad lad would be sent away to write a humiliating confession of his sexual perversion which would be filmed and put on an internet video site, on Mistress' site.

Photographed in many types of erotic lingerie.
On a fairly regular basis, Mistress has me, sissy gina, photograph robert in cute girly dresses or in lingerie. There are hundreds of pictures. Mistress always selects the best and they were put up on her web site. It was linked to many others. The story of robert’s feminization is everywhere, and Mistress continues to insure that her sissified male is always be recognized as just that. Robert keeps a blog of all his humiliating experiences and how he feels when his sissification is discussed openly in front of him.

Sissy robert always wears a pink collar with rindstones with his name is in large letters "sissy robert". It has a place to clip on a leash, which Mistress Gypsy sometimes did when she takes her pet sissy out in public. It was quite frequent that she takes her sissy out in public too, whether it was restaurants, coffee shops, stores, or wherever. Mistress takes great delight him having robert on a leash in public and when people look, she says, "This is robert, my pet sissy. Isn't he cute in his ruffled dress and frilly petticoats?" She delights in telling curious on-lookers about how she feminized him and turned him into a sniveling pansy. Robert would be standing there in his frilly little girl style dresses with petticoats and just curtsy, and blush in humiliation as Mistress described his feminization. She would show pictures of robert as the stud male he once was and compare it to a pictures of him in sexy lingerie. She notes that Robert doesn’t have sex with women any more. It always was difficult for robert because he was so ashamed at being a male and letting a woman feminize and sissify him. The things that Mistress Gypsy says about him, in front of him, make him so humiliated. On the other hand he craves this. He craves being shown off in public as a girly boy in dresses. It also makes him sexually aroused, and Mistress knows it.

Mistress Gypsy finally has what she wanted, a totally sissified male that is completely dependent upon her. Her new sissy will not be allowed to pass as a woman. Sissy robert would remain recognizable as an effeminate sissy male to all.


Advogada said...

Delicious, wonderful, loved it!

Sissy Chrissie said...

The only truly sad thing about all this is that it's a fantasy.

OMG, just delicious...

Anonymous said...

Has a sissy myself I love this storie.
Sissy Robert is very lucky sissy having a
Mistress look after him.
I love wearing panties and bra to work every day
I have also gone out on the town dressed a sissy.
Sissy Gina and sissy trica keep up the good work
And please write more stories.
Thank you
Sissy Mellisa.

kitty sissy said...

Hi gina I love this and I woud love you to right some more .
SO big thank you .
love kitty x

Anonymous said...

sissy phyllis says: I envy sissy robert (shouldn't be "Roberta" ?) wearing make-up is so exciting. I also wear my hair rather short but have it bleached light blonde

simone kenyon CD said...

i enjoyed this immensely, i feel for robert and i love the wicked humour of mistress :)
i wear bra and panties all the time and only wear womens track pants and tops out .... usually with an oversized t=shirt to cover it
keep these coming

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Anonymous said...

I envy Roberta. The Mistress has been most competent changing the sissy boy into a sissyfaggot.However one thing still is missing. She need to wear a locked steel collar in public