Sunday, October 4, 2009

sissy robert - part 1

sissy robert's story

I would like to share further information on the situation of sissy robert, one of Mistress Gypsy's sissy pets. This is an elaboration from "Sissies Serve Mistress Gypsy & Friends – part 2 of 4"

Sissy robert represents a new direction in Mistress' sissy training. In the past, Mistress Gypsy had several sissies that she fully feminized to the point of having them take hormones and they really became pretty girls. In fact the sissies felt like pretty girls, which diminished some of the effect of Mistress' training. So Mistress decided that her next sissy would remain an obvious sissy male. He would not receive female hormones so his raging youthful male sexuality could be best used against him.

Tricia and I fit into a different category of Mistress' sissies. We had been trained to become sissy queers, being constantly forced to be affectionate towards one another. We were also trained to please men and become real cock lovers. But sissy robert would be different.

Robert was a crossdresser in his mid 20's and through his curiosity was caught in Mistress Gypsy's web. Tricia and I (sissy gina) were Mistress' house maids and also used for the sexual entertainment of her and her friends. But the young robert was destined to be Mistress' sissy pet. It took about 8 months to get robert to where she wanted, as tricia and I watched the gradual transformation from a young stud male who dated lots of girls with some occasional crossdressing on the side, into a totally sissified male.

It started with Mistress buying him pretty lingerie and had him model it for her. At first he was quite embarrassed, but Mistress’ constant prodding and compliments weakened the young man’s will to resist. She took lots of pictures and showed Robert how to improve his feminine look and demeanor. Gradually Mistress had him wearing only women’s lingerie and he finally shredded all his male underwear on film and video. Following this, his was to wear stockings and garters under his male clothes when he was not with Mistress. Next it was a corset. Mistress helped him shop for several at an erotica shop in the city. Robert was so embarrassed when he had to try o the corsets in the store and the pretty young salesgirls went into the dressing room with him to lace up the corset.
The salesgirls could see he was wearing a garter belt with stockings and a pair of ruffled panties under his male attire. Mistress Gypsy would also hold lingerie and corsets up to Robert in the store and asked him loudly, “How do you think this would look on your Robert, or I think this would go nicely with your pink bra and pink ruffled panties. Don’t you think so?” Invariably when a purchase was made, Robert would have to wear the sexy garment home. He had to go back into the changing room after Mistress declared, “Oh, this is so cute, I think I’ll have robert wear this home.” And to the salesgirl she would say, “And be sure to lace his corset extra tight. I want him to develop a nice feminine figure.”

Robert would spend the weekends at Mistress’ home, all dolled-up in dresses and lingerie and do light tasks for her. On the weekends, Robert wore no male clothes at all. Mistress had him walking around the house wearing either only lingerie and high heels, or in skirts and dresses. He was not even allowed to wear women’s slacks at home on the weekend. There were also no wigs for Robert, and although he always wore a bra, it was either lightly padded or not padded at all. She was trying to keep the young lad from becoming totally feminine in looks. Her goal was to keep him as a sissified male under her control.

Moving in
After a few months, Mistress offered for robert to move into a spare bedroom, and he could come and go as he pleased. Robert liked the idea. He could have the best of both the normal and crossdressing worlds, so he agreed. Secretly Mistress had other ideas, but that would unfold. In just a matter of two weeks after moving in, Mistress Gypsy had Robert wearing girl clothing at all times except to work, where he would be wearing panties, a tightly laced corset with garters, and stockings beneath his male clothes. As a general rule, Robert was required to wear stockings with garters instead of pantyhose because pantyhose were more for normal women, and stockings with garters were more sexy and erotic. They were so much more befitting a male transvestite sissy, and that is what robert had become.

From the beginning to this point in his transition Mistress would have Robert masturbate while wearing girls clothing, often. It was her desire to hook him on associating sex with wearing girls clothing. It didn’t take much to do this since robert was already a transvestite who was turned on by women’s clothes. But Mistress reinforced this with such intensity. Even after Robert had an orgasm, he stayed dressed and after cleaning up, being put into an even prettier feminine outfit than before.

The next step was for Mistress to have the young man wear a chastity device once in a while. Gradually it became more frequent. Mistress Gypsy manipulated sissy boy’s ability to have orgasms by alternating periods of extensive masturbation, and total abstinence by wearing the chastity device. The next practice Mistress started was for Robert to wear a chastity devise before bed with the reason that he wouldn’t have an unexpected orgasm as night. Roberts bedtime attire was panties, unpadded bra, garter belt, stockings, and a nightgown, and of course the chastity device. Mistress would get him sexually stimulated by reading from one of the any sissy stories on the internet. Then she put on a hypnosis CD. Robert inquired, “What’s that for?” Mistress replied, “It is a hypnosis CD that will help you relax and give you sissy thoughts while you fade away into sleep.” She could see Robert was unconvinced. But she went over to him and placed his head against her breast, and stroked his nylon clad legs. She felt his heart beat faster. She knew that if he wasn’t wearing his chastity device he would have a huge erection. “Do this for me sweetie. Just try it for a few days, to please me. OK?” Robert snuggled against Mistress Gypsy’s breasts and reluctantly gave in. After a few nights Roberts objected again and Mistress soothed away his objections. From then on, Robert always had a hypnosis tape playing in his room at night, all night long, over and over. Mistress wanted this to have a reinforcing subliminal message all night, while she influenced him during the day.

Introduced to Sissy dresses
Now it was time to introduce Robert to wearing sissy dresses. Previously he wore normal short girls skirts and dresses at home. He came home from work one day and there were three over-the-top frilly dresses just dripping with ribbons and lace. These were dresses like a little girl would wear, and there were three very full petticoats lying near the dresses, one for each dress, all color coordinated. It didn’t take much for Mistress to coax robert to try on the pink dress with a light pink petticoat. She had him look in the mirror and spin around a few times. He just kept twirling around and looking at himself in the mirror. He was obviously pleased. He liked how he looked in this pretty ruffled dress. Of course there were pictures to be taken. There were always pictures taken.

Between being constantly dressed as a girl at home, the attention from Mistress Gypsy, and the hypnosis tapes every night, the effect on robert was becoming evident. It was obvious that he was enjoying this immensely, more and more. He was hooked and Mistress knew it. One day, while Robert was all dolled up in a cute sissy dress, Mistress Gypsy pulled out some videos of him wearing lingerie and high heels, and shredding his male underwear. “That was a momentous occasion, sissy boy. Don’t you think?” She asked the young budding sissy. “Yes, Mistress, I remember it well. I felt so embarrassed but so excited when I did it.” “Well, my little sissy boy, you are now wearing women’s clothing all the time except to work and even then you are wearing women’s lingerie. I think you should wear women’s clothing to work too.” Robert, gasped, “But Mistress, I can’t do that.” “Don’t worry,” cooed Mistress softly. “It will be clothing that is unisex, androgynous. No one will notice. We’ll get you some slacks, loafers, and some plain shirts from the women’s department.” “Are you sure they won’t notice?” asked robert. Misress replied, “Absolutely not my dear pretty boy. And you can still wear a man’s tie since that is required in the office. But that will be the only concession I make. Aside form the tie, you will only wear women’s clothing. You can do this and completely get away with it. No one will know your wardrobe is from the women’s department except you and me.” By now, Robert was so hooked on wearing women’s clothing, this seemed almost logical and tentatively by apprehensively went along with the idea.

Next day, Mistress Gypsy and robert went shopping. Mistress wore leather pants, a silky top, and high heeled boots. Robert dressed as a male as he would for work, with all the lingerie beneath. She was expecting lots of packages, so she decided to have sissy tricia and I come along. But Mistress was going to make this an attention getting event. Tricia and I were to be dressed in our frilliest French maid outfits. Our outfits had lots of white lace ruffles on our black dress. We also wore white petticoats to give a full look to our dresses. And we also wore 5” high heels. It would mean we would walk slowly and the sound of our heels on the floor would be noticeable. Finally, tricia and I wore our usual wigs and overdone make-up, and nails.

In the department store, Mistress took charge. She decided to start with the women’s slacks. She picked several pair and proceeded to tops. She picked out some that were white and also several colored blouses. The styles were not very masculine. Mostly they were feminine colors and had scalloped edges or some other feminine styling, subtly feminine, but feminine. As she selected them, tricia and I were charged with carrying the items as maids do. Our little entourage got a lot of looks, especially since we two sissies were dressed up in French maid’s attire and the click click of the high heels on the tile floor was pronounced.

Robert didn’t have much issue with the slacks, but he commented, “Aren’t these blouses a bit too feminine for my job?” “Oh, not at all Robert, besides, the tie will serve to balance out any subtly feminine style. Trust me, this will work.” One could tell that Robert was not totally convinced, but he went along with it.

Mistress led him to the men’s department to the men’s dressing room. “Now take these in here and try them on Robert. And I will wait out here. I want you to come out and show me each outfit you put on.” “Mistress, I can’t do that. I will be wearing women’s clothing and trying them on in the men’s dressing room and if I come out, others will see me.” Mistress took the items from her two sissy maids and said, “Don’t worry pretty boy. You are going to be wearing these to work, so every one will see you anyway. Remember, no one will notice.” Mistress was always so convincing, lately, even more so.

Robert did as he was told and came out to model each outfit. Mistress had him twirl around and walk a bit so she could see how it all looked. She was obviously pleased with most of her selections as people in the men’s department looked on at the two sissy maids and robert, a man in women’s slacks and blouse. She said, “These will do for now,” as she selected three pair of slacks and five tops. Sissy tricia and I carried the items over to the men’s sales counter as instructed. The male sales clerk looked at our unusual group and asked, “Are these for you ma’am?” Mistress immediately shot back, “Oh no, these are for robert,” and proceeded to point to him. “But ma’am,” the clerk replied, “these are women’s clothes, how could they be for him?” Mistress was not going to miss this set-up. She replied, “Robert is a transvestite sissy and he wears women’s clothing most of the time as it is. Just look here.” As she said this, she reached into his shirt and pulled his bra strap into view. “See, he is already wearing lingerie. This will just complete the look.” The clerk sighed and smiled, glad to have the sales commission. Meanwhile, Robert was turning red from embarrassment from being exposed as a sissy in public. The items were rung up and being put into a bag, when Mistress said, “One moment please, robert is going to wear those slacks and blouse home.” The sales clerk was fine with that. “All right sissy boy, go change into your new slacks and blouse,” demanded Mistress. Robert again blushed deeply and complied. Tricia and I just looked at each other and smiled. We knew what this was like, because we had both been though the early sissification process ourselves. We smiled too because we loved seeing other boys turned into girls or sissified males like us. Tricia and I carried the packages and followed Mistress Gypsy and sissy robert to the shoe department.

Once again, it was obvious that Mistress Gypsy was a woman on a mission. In no time, she selected several styles of shoes and asked the sales clerk to bring them out in robert's size. Mistress demanded, “OK robert, try each of these on and walk around a bit in each, and be sure to look in the mirror.” The salesman was shocked that a man was trying on women’s shoes, and he just stared at Robert for a minute, not knowing what to say. It was obvious that robert was quite uncomfortable being stared at like this. Mistress, noticed the shoe salesman’s look and said, “Robert is a sissy and likes wearing women’s clothing. In fact, he is adding to his feminine wardrobe so he can get rid of the last of his male clothing. He doesn’t want to wear male clothing any more. Isn’t that right robert?” His response was a weak, “Yes, Mistress,” as he blushed deeply and felt so humiliated. Mistress pushed him, “That wasn’t a very definitive answer my pretty little sissy boy. I want you to reply in a whole sentence and I want you to answer only if you really want this for yourself. Do you want to get rid of all your male clothing and dress in women’s clothing from now on?” Robert really didn’t want to do this. He wasn’t ready to totally wear women’s clothing. But he was weakened. He didn’t have the will to say no. So he blurted out, “Yes I want to wear women’s clothing all the time.” Mistress smiled and softly said, “OK now pretty boy, try on your shoes.” The shoes that Robert tried on were not exactly unisex. Mistress picked out a selection that varied from true flats to shoes with about a 1 ½” clunky heel. Robert’s mind was wandering, and not paying attention to the new shoes that were now being rung up. Once again, he would wear one of his new purchases home. He was wearing only women’s clothing in public. Little did he know this would be the last day he wore men’s clothing.

Robert at work
When Monday came, Robert was told to wear his new clothing; slacks, white blouse, and a pair of flats. It was obvious he was uncomfortable even after he put on a tie. As usual, Mistress soothed him and told him that no one would even notice. Robert had to put his wallet in his front pocket because he hadn’t noticed that any of his new slacks had back pockets.

After a few hours at work one of the women he works with, asked, “Oh, new shoes, robert?” He muttered a yes and went on. No one said anything else that day. The week went by and no one made any comments, but some of the women did notice a subtle difference in his attire. At the end of the week, Mistress asked if anyone noticed his clothing change. He noted the shoe comment. Mistress said, “See, I told you so.” The next week Robert continued to wear his new clothing, but on Thursday a new blouse was brought in which was a bit more femme, and the shoes with 3/4”heels were also put out to wear. Robert did get a few comments about his clothes that day, like, “New style, hey Robert?” He just gave a grunt and went on with his work. That following weekend Mistress took Robert to get his ears pierced. Once again, he objected weakly, and Mistress won him over. There were simple gold studs. No one would notice.

That weekend, as robert was all dolled-up in one of his frilly sissy dresses, Mistress again talked to robert about his experiences went with him wearing women’s clothing to work. Robert replied, “Oh, OK, I guess” was his answer. Mistress took this as a great triumph. “See, I told you it would be no big deal. Just listen to your Mistress. I will always look after you. Besides, isn’t it so much more comfortable to wear women’s clothing?” Robert remained a bit ambivalent and once again replied a meek, “I guess so.”

Week three with robert’s new wardrobe at work:
On Monday morning the sissy boy’s clothes were laid out for him to wear that day as they were every day. He noticed that there were no socks. His thin women’s opaque black microfiber socks were now removed. Now his black semi shear stockings held up by garters would show beneath his womens’ slacks. The lad looked into his drawers and closet and saw there were no socks and also all his male clothing was missing. He immediately went to see Mistress Gypsy and ask what happened to all his male clothes. Mistress was calm and said, “Dear sissy boy, everything at work is going so well. You even said so yourself. You don’t have any need to have those male clothes anymore. I had sissy gina remove them all and she will take them to a charity.” “Robert almost cried, “Oh Mistress, please don’t do that. It makes me feel so exposed and vulnerable to have only women’s clothing and no male clothing to fall back on.” “Now robert, remember the declaration you made in the shoe department? I asked you if you wanted to wear women’s clothing all the time. Furthermore, I said, only tell me if you mean it. And then you replied in front of the shoe salesman, ‘Yes I want to wear women’s clothing all the time.’ I just took you at your word. Besides, everything has been going so well. You even acknowledged that. Now, I know you feel a bit vulnerable, but I am here for you. Trust me sweetie.” Mistress could be so convincing. When she was around, everything seemed so right.

Also that Monday the young man wore the higher heeled shoes. They were a full 1 ½” with a clunky heel. He would wear heels of that height all week. The earrings he wore were noticed by all the women that week in addition to the high heels. Little did he know, that all the women and some of the men were talking about him behind his back. Even the boss was beginning to notice some of the changes, but said nothing.

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.

Saturday, November 29, 2008

sissy gina's fantasy with Master Jim

The following was written under the inspiration of Master Jim.
He started the topic and I wrote the story.

Part 1 The Fetish Ball

I would like you to take me to a fetish ball. I suspect you
will wear something befitting a doinant male. Something which
belies your uderlying strength and dominating spirit. It could
be leather or simply something casual in black. Then there
would be me. Dressed in a short pink dress with lots of frilly
lace, ribbons, and bows. A real Lolita style little girl look,
but exaggeratedly feminine. Of course I will be wearing a
petticoat to give a real frilly look. Aren't I so innocent?
I am wearing tan seamed stockings and 5' high heels in pink.
They are open-toed to show off my pretty polished toenails.
The stockings are held up by white garters, but the skirt is
short and the garters sometimes show. I am also wearing a
really tightly laced white corset to which the eight garters
are attached.

When I show up at your home, I find that there is another
effeminate sissy dressed very much like I am. You introduce
her as jill. Before we go to the ball, You take out two butt
plugs and tell Jill and I to bend over. We comply and one at
a time you slide down our panties and push a lubricated butt
plug into each of us sissy girls. You declare, "Now you little
pantywaists, you will be plugged all evening so that you will
remember your role. That is, to serve me and be my pleasure
dolls. Later the butt plugs will be replaced with my raging
hard cock, so remember that. Remember that all night long."
We are told to pull up our ruffled panties and are ushered
out the door. As you usher us out the door, you pat each of
us on the behind, just enough to make us aware of the butt
plugs, as a reminder of our submissive status.

All three of us sit in the front seat of your car, with me in
the middle. As we travel, you constantly have you hands
pawing me, and sliding them up my skirt. You tell us, "OK
now my little faggot cum sluts, I want you to stay together
and hold hands all night long. When I say the word 'pansy' in
any context during the evening, you are both to kiss each
other passionately and caress each other as a couple of
effeminate sissy queers for 1 minute." Right then we heard
you say the word pansy and immediately acted like the girly
boi fags you desired. We saw your smile as we drove on.

The fetish ball was quite an event. People were wildly
dressed and everyone was having a great time. After jill
and I fetched you a drink, holding hands the whole time as
we walked together in our 5" heels, you take a gulp and
loudly demand in a voice that many can hear even over the
loud music, "Get on your knees you pantywaist sissies!"
We curtsied quickly and complied. You reach into your pocket
and pull out two pink collars with rindstones. There is a
big smile on your face as you place it around my neck in
front of everyone. Then you did the same for jill. A small
group of people is standing and watching as you put the
pink collars on us, and they applaud. Next, with jill and
I still on our knees, you take out two pink leashes and
clip one on each of us. I don't know about jill, but I was
feeling really humiliated by this. I never expected this
kind of humiliating treatment. I swallowed hard and told
myself that I am a submissive sissy and need to acknowledge
it, so I complied with everything you said, reluctantly but

Next we hear your voice boom out again, "Alright you
little pansies, you can stand up now." Oh, my, he said
that word, 'pansy'. Jill and I quickly looked at each
other and simultaneously started our required one minute
erotic encounter with one another. We did act like a
couple of absolute fairies, kissing and caressing. I
could tell jill was getting relly turned on, her little
clittie was hard and pressed up against me. Of course
I was turned on too. I couldn't belive that I was being
made to act like a sissy queer with another pantywaist
in public. Master Jim is once again heard in a booming
voice, "Look at that folks, my little submissive cum
dolls are so hot for one another. Did you know that neither
of them are allowed sex with women anymore?" One
leather-clad woman from the crowd yelled out, "Who would
want them? All they are good for it clean up duty, if you
know what I mean." The group applauded.

The evening was quite interesting. Several shows and
displays were put on and the crowd loved them. There was
a bondage corner too. Master Jim assured us that one day
we would be displayed in that bondage corner too. All in
all the evening was a great success and a lot of fun. Of
course it was intensely humiliating to be pushed into an
increasingly submissive role in front of so many others.
Jill and I were both sexually turned on by the constant
sissy play in which we were forced to engage all evening.

Part 2 After the fetish ball

On the way home, sissy jill and I heard the word 'pansy'
many times and over and over again had to act like the
sissy queers you were teaching us to become. You just
laughed and degraded us. We were reminded often that
we were effeminate sissy sluts and only worthy if we
were serving a man, of course you were referring to
yourself as that man.

Back at your place, jill and I were instructed to unzip
each others frilly sissy dresses and take them off, along
with our petticoats. So there stood both gina and jill in
white lingerie and perched atop 5' high heels. We noticed
that as soon as we started to undress you we snapping
pictures with your camera. Then we were instructed to
pose in sexy poses, individually and with one another.
It seemed as though you were a director and making a movie.

Next you came over and tightened both our corsets, and I do
mean tightened. I could hardly breathe, but the corsets did
give us a nice feminine shape. Once again you felt our butt
plugs. You asked, "Are you two little cum sluts ready for
a man's cock?" Almost in unison, jill and I replyed,
"Yes Sir."

"OK you faggots, beg for it. Tell me that you want it.
Tell me how much you need to have my cock in you. Tell me
what fucking sluts you want to be. Tell me you want me to
be your Master. Now you first gina slut."

I didn't know where to start, but I knew I needed to start
somewhere, "Sir, I am a lowly sissy male. I have no greater
purpose than to serve you, a dominant male. As a sissy male
I know I must wear women's clothing and that I must dress
sexy to please and entertain you. It is kinky and perverse
but I like to do this for you. I like to dress like a sissy
slut for your pleasure. You should also know that I want
to be sexy and appealing for you so that you will enjoy
using me for your sexual pleasure. As a sissy it is my
job to wiggle my ass and hope that you will want to use me."

In a demanding tone, you say, "Get on with it gina, you
slutty fag boi."

"Yes, Sir. Please know Sir that I want your cock in me.
It is important for me to please you and to show my
submissive status. Please make me suck you cock. Please,
because I need it so. I want you to be sexually dominant
over me. I know that you will not only make me suck you
cock but fuck my ass as well. I know this is my fate and
I want it. I want it so much. Make me your cum doll. Make
me clean you off after you have finished using my mouth
and ass."

"Are you ready to be my submissive cum slut, gina?"

"Yes, Sir," I replied. I get on my knees and beg for
you to use me and make me you pantywaist cum doll.

"Well good gina, you can have your wish." With that you
take out a leather device and start to put me in it. I
realize it is an armbinder. My arms are soon tightly
fastened together behind my back. I am positioned in
front of a nearby tall mirror. "OK slut, do you like
what you see? Do you like being a sumbissive male in
erotic women's clothing and tied up in bondage?"

I felt so humiliated seeing myself like this in the
mirror, but at the same time I was strangely excited.
"Yes Sir, I like what I see. I like dressing femininely
and being in bondage."

"Good, my little cum doll." With that I see you drop
you pants. You cock is already engorged and you push me
to my knees and shove your cock in my mouth, and demand,
"Suck it cunt." I do. I do so eagerly. I alternately suck
it, lick you balls, even lick you ass as you demand. I
change the pace of my cock sucking many times. Sometimes
I use my tongue around the head of your cock and other
times I take it all into my mouth down to the base of
your engorged shaft. "That's right you little cock sucker,
work it harder. Work it baby. This is what you're good
for, gina. Suck like you really want it, because you
know you do. You're just a fucking cunt. Look in the
mirror. Look what you are. Look what you have become.
You're a sissy cunt."

You grab the back of my head and push my head down on
your cock so that I gag and gag. "Don't stop cunt. You
gotta learn to take it doll. Take it all." Then suddenly
you pull me off. In a moment I feel you from behind,
pulling me up to my feet. My arms are still tightly bound
behind me as you bend me over forward. I feel the butt
plug pulled out of me, but almost right away, I feel you
pushing your hard cock in my sissy pussy. Ohhh, it hurts.
Your cock is large and it is such a tight fit inside me.
I wince a bit. You notice this and state, "You better get
used to this because you are going to get fucked regularly,
you fucking cum doll. And that is what you want, isn't
it? That is what your are here for, isn't it? If you want
to wear the skirt, you better learn how to take the cock."

I meekly reply, "Yes Sir. That is what I want. That is
what I need. I know that I am sexually submissive and
can never function as a man, so I must function as a
sissy cum doll."

"Now look in the mirror, sissy bitch. You are mine now.
You are my cum slut and I will fuck you anytime I want
and use you for my pleasure. And I will tie you up to
further show you I am boss. I am going to fuck your ass
good, cunt." With that, I feel you push inside me harder.
You push in and pull out. I am so helpless all trussed
up in the armbinder. The corset barely allows me to
breathe, and I can hardly stand, perched on my 5" heels
as you ram your cock inside me over and over again.

As you pound my ass, you continually degrade me verbally.
"Slut gina, I am going to totally dominate you sexually.
It is my intention to make you into my personal cum doll,
and you will beg for it too. I will fuck your mouth and
sissy cunt to show that I am dominant over you. You will
continue to wear sexy women's clothing to reinforce your
submissive status. In fact, you will only wear skirts and
dresses. I don't want you to be wearing women's pants.
Skirts are for sissies, and you are to be my submissive
slut doll and will be in skirts all the time from now on."

It seems like I have been fucked forever. Bent over, in
bondage, and perched on high heels, I am beginning to
feel weak. I am precariously balanced, and would fall
over from pounding rhythm of your hard dick in my ass
pussy, over and over again. Only your strength keeps
me from loosing my balance. It makes me realize even
more that you are strong and in control and that I can
only rely upon you. The whole situation reinforces your
strengths and my weakness and my dependence upon you.

After an eternity of having my ass pounded as I am
forced to watch my humiliating submissive role in the
mirror, I feel you pull out. In an instant, your cock
is in front of my face and you demand that I suck your
cock again. Immediately you put your hand on the back
of my head and shove it so that I take you whole cock.
I gag, but I persist in my submissive role and suck. I
feel you are cumming. A load of cum is shot into my mouth,
and as it is, you say, "Don't you dare swallow my cum,
you fucking slut." With such a load of cum, I have an
urge to swallow, but resist as I am told.

"Jill get over here." Jill immidiately complies. "Gina,
give all that salty cum to your faggot girlfriend." Jill
comes over to kiss me and I work diligently to transfer
all you how salty cum into jill's mouth. Likewise jill
is also ordered not to swallow. We transfer the cum back
and forth to one another several times as demanded, until
finally you order, "OK jill, swallow the cum, and clean
off my cock, slut." I am released from my bondage and we
are both stood up in front of the mirror so we can see
ourselves, two effeminate sissified males in sexy lingerie,
make-up, and high heels. But what is more important is that
we were beginning to realize that we were being sexually
dominated by a man, and we no longer had any choice in
the matter. This is what Master Jim demanded, and we gave
ourselves to him because we are weak and submissive and
Master is strong and dominant.

Jill and I were both told, "OK you pantywaists, I want
you both to know that I have taped this whole incident.
After some editing, Gina, you will be required to view
this tape regularly so that you see yourself in the
degrading submissive role in which you belong. And jill,
don't worry, there will soon be a tape of you too. In
fact there will be lots of tapes of both of you on your
knees, on your backs, and in many humiliating and
submissive roles."

Part 3 Further Training Planned

Jill and I were standing infront of the mirror in our
lingerie waiting for our next instructions. "Now my
little fairies, I want you to know that it is my intention
to turn you into sissy faggot queers. You already can not
have sex with women and can never use your pathetic little
clitties to penetrate another person, ever again. You role
is to receive a man's cock in your mouth and sissy ass.
It is my intent that the two of you will spend most of
your time together as two sissy queers. You will be made
to kiss and caress each other regularly. You will sleep
together in a single bed wearing a bra, panties, garter
belt, stockings, and nightgown. I want you living so
close to each other so that you are always feeling each
other's silky lingerie clad bodies. I am going to train
you two so that you will only have sexual release with
one another. You may not suck one another, but be ordered
to cum all over each other as I demand. You will be
instructed to act like the real fairies that I am going
to train you to be. I am going to make it so that you
are so sexually charged up by one another on a regular
basis. This will be for my entertainment and also to
reinforce you submissive roles. All this will be
documented with photos and video." "I intend to have
the sissy queer activities of the two of you together
all over the internet. In addition you will often go out
in frilly sissy attire in public so all can see you and
gawk at you. I will totally break your male egos and I
will make you both totally submissive."

"Then there will be more training with me." Jill and I
look in the mirror and realized we are being totally
dominated into becoming transvestite sissy cum dolls.

Saturday, June 2, 2007

Mistress Gypsy Teaches Her sissies a lesson

Dearest Mistress,

I have so diligently desired to be submissive that I never thought about spanking someone else, especially my sweet pantywaist sissy girlfriend, Tricia. For you dear Goddess, I will do so, because you order it.


sissy gina

The story

So Tricia sweetheart, as Mistress Gypsy watches, I will prepare you for the punishment she has decreed. I may cry doing this to you but I must. Girlfriend, both of us will be dressed in matching lingerie and 5" heels. To prepare you I will make your heavily boned corset even tighter than you are accustomed to wear. Your eight garters from the corset will be checked to insure your stockings are taut, and I will run my hands up and down your stockinged legs to feel that you seams are straight. As I do, my hand will slide up to your pantied butt and then around to the front. I shall rub your sissy clit through your panties until you are quite hard. I will also kiss you gently on your deep red lipstick covered lips and press against you. I want you to be sexually aroused for your punishment.

Mistress will be in a large cushioned rattan chair with fan back. She will have one leg over the leg of the chair in a leisurely and domineering pose. I sit on a simple chair only 2 feet away as you bend submissively over my knee. As you do, I notice you quiver a bit and look up to see that Mistress Gypsy has positioned herself so that you can see her uncovered womanhood. I slide your panties down and feel you getting more sexually aroused. Obviously you are thinking of your tongue working to please Mistress Gypsy's pleasure zone, now less than 2 feet away. WHACK, WHACK, WHACK. I slowly and rythymically swat your ass until it is red. The whole time Mistress derides you with humiliating comments. She reminds you that you are not a real man and that you’re longing to dive upon her pussy with your tongue is the best you can hope for as an effeminate sissy. I look up at Mistress to see if she is satisfied. I continue to swat as you squirm and wiggle until Mistress Gypsy laughs and motions me to quit. She leans over and whispers something in your ear but I do not know what she said.

Next you are positioned on your feet, bent over, with your hands on the chair and your face only 6” from Mistress Gypsy’s vaginal zone which you beg to satisfy. As you are bent over, Mistress further derides you the submissive effeminate male that you are. I then bend over and begin to kiss your reddened ass in an effort to make it feel better. As I do so, I use one hand to caress you hard little sissy clitty and the other slides up and down your nylon clad legs.

I am so occupied with you that I do not notice the stud male in the room until he grabs me around the waist and thrusts his hard cock into me and presses me against you. He is screwing me from behind in an instant and I can do nothing but hold on to you. He pulls me away from you and says, “Bitch you are mine now. You can play with your sissy girlfriend later you little fairy.” You turn you head and as you do, there is another big stud male with a hard cock and a big grin. Mistress Gypsy grabs your head and looks at you and smiles. As she does, the second stud penetrates you from behind with his hard cock as you are still bent over and in prime position.

Mistress Gypsy now has the studs position us so that we are facing each other, but both bent over being fucked from behind. We can clearly see each other being eagerly screwed by a man, knowing that neither of us will ever be able act as these men, to enjoy screwing another. All we can to is to put our arms around each other in comfort and let the men have their way with us. Mistress laughs wildly and humiliates us with derogatory comments.

Suddenly the man screwing me pulls out and spins me around, shoving me to my knees. Yours does the same. Then almost simultaneously they both ejaculate on us. Our faces are covered with sticky cum and our hair is a mess, also thick with cum. Each of us has our heads shoved onto the cocks of our respective studs. There we are instructed to clean then off until they are satisfied.

Mistress Gypsy says, “Don’t stop now you panty boys, the camera is still rolling. I want to get the rest of this for my web site.” The whole scene has been video taped. She instructs us to lick each other clean of all the sticky cum ejaculated upon us. And as we do so we are to also to caress and kiss one another acting like the prissy fairies we are. I will never forget the first kiss we shared as our faces were still covered with salty semen. Our lipstick covered lips slid back and forth with the creamy cum lubricating them. The taste of your lips, sweet girlfriend, and the taste of cum from the two stud males who just finished using us for their pleasure leaving us sexually unfulfilled. I’m so horny Tricia darling and you and I now locked in a tight embrace.

Sissies Serve Mistress Gypsy & Friends - 4 of 4

Part 4

The final performance

Oh it was such a relief to be out of bondage. We knew that the pictures of us trussed up as a couple of sissy males in bondage while eating pussy would be quite humiliating. Mistress Gypsy said, "Sissy gina, you lost the competition so you will be required to recite your confession while you and tricia embrace and kiss. I want you to do this until you both cum all over each other, but your sissy boyfriend, tricia, must cum before you do." Two weeks ago, Mistress had each of us write and memorize a confession of our perversions, which we would recite when demanded. Of course it had to be humiliating and include praise for our Mistress Gypsy.

The women all gathered close and sipped their drinks, which sissy robert filled while tricia and I were in bondage. Tricia and I stood close, held both of each others hands and gently kissed as I began my monolog. "Dear Mistress Gypsy, thank you for making me a better sissy than I was before and for the training and attention that you have given me." I ran my hands from tricia's broad male shoulders down to the tops of his stockings. "I am a sissy male and I must confess that I like to wear women's lingerie and in fact, any type of women's clothing. It gives me great pleasure when I am dolled up in make-up, heels, and hose. The sensual feel of the silky delicate clothing brings me excitement and stimulation." As I drew a breath, tricia hugged me and gave be a long empassioned kiss and, as I moaned, he slid his deep red lipstick covered lips down my neck and onto my bare shoulders. One of the women shouted out, "keep going faggot, we want to hear more."

I recouped my composure and was about to continue but couldn't remember my confession so I just continued on as best as I could. "Dearest Mistress, I want to thank you for showing me that I am a submissive male and that I cannot be worthy of having sexual pleasures with a woman as a male. I am now content to be relegated to the status of a sexual toy for the pleasure of others." I wrapped my arms around tricia's back and pulled him close and slid my body down so that the silky fabric of my camisole rubbed against his erect cock and made it swell further. He moaned with delight.

"I now also know that you have trained tricia and I together for a purpose and that is to make us desire each other and be sexually attracted to one another by having both of us sexually charged and in lingerie together so much. You have broken my hope of ever having a relationship with a woman, other than as her servant. I now know I must be satisfied as a sissy with a sissy." I moved my hands to tricia's rear and pulled him close, starting to move to an upright position as I kept my body pressed against his rigid cock. As I moved up I made sure that the whole time tricia's cock was pressed against my lingerie clad body. When fully standing I kissed my sissy boyfriend on the mouth. Of course we were wearing matching lipstick because we knew we would be kissing together like lovers.

"I must also confess that I do like tricia as both my girlfriend and boyfriend. You are indeed so wise to make us be effeminate sissy males together. When you make us perform for you, I feel humiliated because I am a perverted sissy male and you know how to manipulate our psyches. You are young but know us profoundly and allow us no secrets." Tricia suddenly grabbed my pathetic but hard cock. I almost came right there but luckily didn't because Mistress instructed me to see that my sissy boyfriend came first.

"Mistress, you are a beautiful woman and I tried to look as good as you do, but could never attain that ideal. In fact I am now committed as a result of your training, that I should not try to obtain that ideal that you represent as a real woman, but to achieve that of an idealized woman who does not exist. The kind of woman that most men strive to have, I must become. I now dedicate myself to be ultra femme, to wear girl’s dresses with bows and ribbons, and frilly petticoats. I will never again wear male underwear but instead, delicate lingerie to always remember my place. I am humiliated when at work, the men line up at the urinals to pee proudly holding their well hung cocks in their hands. I, on the other hand, must slink over to the stalls and pull down my frilly panties and sit down to pee. Of course I can also see my tightly gartered stockings holding up my sheer stockings while only a few feet away from all those male studs." I whispered to tricia not to make me cum yet. He let go of my cock. I was so sexually stimulated I could barely stand it and with a glance at Mistress Gypsy, I could tell that she knew it too. She smiled and was enjoying my humiliation and the fact that she had pushed me into deeper submission. She knew she had me in her control.

I gently caressed tricia's hard cock with my left hand, pulled him closer to me by putting my arm around the small of his back, gave him a slow kiss with a light touch of my lips and continued. "I, I, I am sexually attracted to you tricia, darling. I like feeling your hard cock against me. I like it when we are in bed together dressed in lingerie and long nightgowns. The feeling of the silky fabric as we press our bodies together simply thrills me. Dressing with you as girls with ruffled petticoats and hearing the petticoats swish as we hug one another in a romantic embrace sends my head spinning". It was too much for sissy tricia, the women watched and cheered as he came all over me. Mistress said, "now sissy gina it is your turn but make sure that tricia wears your cum on his face." "I immediately replied, "Yes, Mistress."

I knew it wouldn't be long before I would cum as well. I pushed sissy tricia down on his knees, and as I did he put his hands on my legs where the garters and stockings came together. He pressed his fake breasts against me so that my cock lay in between. Nearly breathless I continued, "Thank you again Mistress for turning me into a complete sissy fairy, for making me love the pleasures of being with another sissy in lingerie, and making me recognize my place at your feet."

I was so stimulated all I could do is blurt out, "Oh tricia, rub my sissy cock. I love being a sissy and a fairy and want Mistress to continue to feminize me. I don't want to be a man, only a sissy in lingerie and heels. Oh Mistress, make me a fairy, make me a faggot, let me please you as the sissy I am...." With that I came and came all over my roommate’s face. He had sticky cum dripping down from his cheeks and the bangs of his blonde wig.

I was exhausted and thought I would fall over. Mistress Gypsy ordered us to clean each other up by licking up all our cum. The women directed us to any cum we missed. We realized then, that we were being photographed the whole time and would relive our humiliation in front of Mistress Gypsy and her friends again and again.

Departure and hints of what is to come

Sissy pet robert was ordered to help us back into our frilly French maids dresses so we could clean up from the party. As we began our clean-up, the women thanked Mistress Gypsy for an entertaining evening and said they were looking forward to seeing the pictures. Mistress told her guests, "I will also be posting the best of them on my web site Monday. That way everyone can enjoy them. In addition, my pet will be staying with my two devoted sissy boys for a week. I have given pet a list of assignments for the three of them to do and invite you all to watch. I will post the times for each sissy performance."

Tricia and I curtsied as each woman left, but none of them acknowledged us. They just kept chatting and saying their good-byes to one another. Tricia and I knew we would be getting further instructions from Mistress Gypsy soon. We looked forward to them with fear and anticipation. When they left we hugged and gave one another a long kiss with our matching deep red lips. My sissy boyfriend, tricia, and I knew we would be sissy lovers for a long time to come and that Mistress had many ideas for our further feminization.

Sissies Serve Mistress Gypsy & Friends - 3 of 4

Part 3

Mistress begins her sissy boys on corset training

Mistress Gypsy said, "Pagan, before you begin, I have something here for our little fairies." She reached into the shopping back she brought and out came two long heavily boned corsets with strong laces up the back and eight detachable garters on each. "Alright boys, off with those wimpy waist cinchers you are wearing. From now on you will be undergoing serious waist training. You will both be wearing corsets nice and tight. Now put them on you little sissy faggots." We did as we were told but couldn't lace them up ourselves. Mistress Gypsy saw our struggle and said, "Now sissies, you will need to lace up each others corset every day. You can start now. But I will check and if you don't lace each other up adequately tight, I will have Pagan lace you up." And with that she smiled knowing that Pagan would lace us up tighter than we could bear. Goddess Pagan said, "They are a couple of weak wimpy fairies. I bet they will do a sloppy job." Mistress Gypsy thoughtfully spoke, "Pagan, you are right about them being weak effeminate fairy boys. However, I have confidence that my sissies are adequately inspired by your reputation and will do well for fear of your hand. Besides it would be so much nicer if they put each other into intense pain and pressure."

Mistress Gypsy was absolutely right, we pulled and tugged on each others corsets. The women chanted "tighter, tighter" and made other comments like "Pull harder you weak little faggot". I made tricia squeal in agony while the women watched joyously cheering me on, shouting, "tighter, tighter, you little sissy boy. Make your little fairy boyfriend squeal some more." When it was my turn, I thought I would pass out. I could hardly breathe because tricia made the corset so tight. Of course tricia got cheered on too, but I was determined not to shout or squeal in pain. Afterwards, Goddess Pagan inspected the lacings of both of Mistress Gypsy's sissy boys. She looked disappointed. The lacings were nice and tight, really, really tight. We had made Mistress Gypsy proud of us, I thought. But just when I get a little cocky inside, Mistress does something to put me in my place. She had us pose for more pictures in our new corsets, kissing and fondling one another, two hot, sexually charged effeminately dressed sissy males acting like a couple of effeminate faggots. Miss Julie gleefully snapped photos of us in the most humiliating positions in which Miss Barb posed us.

Mistress Gypsy humiliates us further

Mistress had us so sexually excited I didn't know how I would avoid having an orgasm. And surely tricia must have felt the same way as we ran our hands over each others nylon clad bodies. Mistress could tell how hot we were. She calmly looked at Pagan and said, "time to lock up and humiliate these fairies. You can use my pet to help." That is all Goddess Pagan needed to hear. She immediately went for an armbinder and trussed up my arms behind me. Then a spreader bar for tricia. My sissy girlfriend had his ankles fastened to a bar about a yard long and then his hands strapped to his ankles. It must have been so painful for him in this position with a new corset too. It looked like my sissy roommate was about to fall over. It took a great deal of balance to be in this position while wearing 5" heels. I went over and helped by having tricia lean against me for support. The women thought that was so cute especially since I was standing up and trica was bent over such that my tiny erect cock was close to his face.

I could tell another woman, Miss Sandy, was really enjoying this. She came over and swatted each of us a few times on our bare butts and then fondled our genitals, none too gently. Tricia and I almost instantly lost our erections. Miss Sandy exclaimed, "these sissies can't even keep up a hard-on unless they are fondling one another. Gypsy you have trained them well. I'll bet they are not even turned on by women any more." Miss Barb said, "I'll take that bet, Sandy." Miss Barb immediately got up and came over to us and started to undress in front of us.

Miss Barb thrust her bare breasts into my face and said, "Do you like this sissy gina?" "Oh yes Miss Barb", I replied. Miss Barb asked, "Would you like to have a nice set of tits like this sissy boy?" I stammered a weak, "I don't think so Miss Barb." "What she exclaimed? You like nice C cup tits on me but you don't like them enough to have your own to play with?" With that, Goddesses Pagan gave me a swift swat on my bare ass which pushed my face further between Miss Barb's bare breasts.

Mistress Gypsy said, "Barb, now that sounds like a good idea. Perhaps I should start my sissies on female hormones to grow breasts. I am a little concerned that it would help them by reducing their natural male behavior with which I can use to manipulate them. However, they would look cute with little A cups. After all we want them to continue their work as males and to continue to function in the male dominated jobs they are in. This will provide a contrast to their sissy nature and keep them humiliated when they see they cannot be real men. I will think about this some, hummmmmm, yes, perhaps some nice little A cups would be nice for you little sissies."

The sissies eat pussy

Miss Barb undid her black slacks and slid down her panties and ordered me to eat her pussy. I glanced at Mistress Gypsy who was smiling and immediately went about my task. I got on my knees, but my task was certainly not made and easier by the fact that I, a male was in a tightly laced women's corset so that I could hardly breathe and had my arms totally immobilized by an armbinder behind my back. None-the-less I was diligent in my efforts.

Miss Sandy did the same with tricia. However, he was in a worse position than I was. He was not only in the tightly laced corset but hand and feet tied to a spreader bar. He couldn't get on his knees. He had to lean over trying to maintain his balance on his 5" heels while eating Miss Sandy's pussy.

Every now and then, Goddess Pagan would swat one of us on the ass if she wasn't pleased with our efforts and called us pathetic fairies. After what seemed to be an eternity of pussy worship, Miss Sandy suggested. "Barb, let's switch and see which of these fairy boys does a better job." All the women loved the idea and tricia and I each switched and strived to please the ladies before us. After Miss Sandy and Miss Barb were satisfied, they each gave a critique of our efforts as though we were in an Olympic event. In the end, tricia was declared the winner of the competition largely due to the increased degree of difficulty from being trussed up in the speared bar.

Goddess Pagan addressed her sissy pet, "sweetie, why don't you come over here and undo your little sissy friends. I like to bind up and humiliate sissy males but just hate to let them out of their bondage."

Miss Barb asked, “Gypsy, why don’t you dress up robert like gina and tricia. I think he would look cute with a wig and some falsies?” Gypsy responded, “In the past I have had several boys whom I feminized so well, including hormones, that they became too much like women and they were no longer much fun to torment. Now I prefer to keep my sissies feminized but don’t let them go too far. I keep sissies like gina and tricia for service and entertainment duties, and to earn money for my household. Sissy robert is like a lap dog. He does not work other than fetching an item or two or giving me massages. He is always dressed in a frilly dress as a male. He does not work and is treated more like a pet dog. His feminization is intense in another different way.” Miss Barb answered, “Oh, it sounds like such fun to have a pet sissy. Maybe I should get one too.”

Sissies Serve Mistress Gypsy & Friends - 2 of 4

Part 2

Mistress plans to entertain friends

Mistress Gypsy, and some of her friends have decided to get together to watch a new chick flick and Mistress decided that she would have her sissy boys provide the food, drink and subsequent entertainment.

At the appointed time, tricia and I had the apartment spotless and all the food and drinks prepared. We worked all day on the sweets and treats to please Mistress and her friends. We knew that if we did not do well it would reflect poorly upon our Mistress. We wanted everything perfect. We also donned our starched black French maid’s outfits with lots of white lace and ruffles. The petticoats pushed out the skirts so that we often could hear them rustle as we passed in the hallway.

Mistress Gypsy Arrives

Mistress' friends we all quite prompt in their arrival. Tricia and I each curtsied deeply and introduced ourselves upon the arrival of each guest and offered them snacks and drinks. Mistress Gypsy arrived fashionably late and made a grand entrance. She wore tight black jeans, a silky top that almost looked like a camisole, and black boots. In addition she had a pet in tow. The pet was one of her sissy lap dogs. Pet's name is robert, a handsome young male in his mid 20’s. As it turns out, robert is a male dressed in a sissy dress. It was pink with lots of ruffles and a big bow. Of course he wore petticoats with his dress. It was a dress very much like the one that tricia and I would wear when we dressed for dinner. Robert had pink painted nails and pink lipstick. It was quite noticeable that he was a sissified male because he was not allowed to wear a wig. In fact he had a crew cut which was highlighted by the big pierced hoop earrings he wore. He was also not wearing a bra to look feminine. He looked like an effeminately dressed male, which is exactly the look Mistress wanted for him. But what was most startling was the delicate pink collar he wore with fake pink stones and the leash that was attached to it. Of course Mistress Gypsy was at the other end of the leash smiling. She went over to the couch and sat down as though she owned the world. Tricia and I knew she certainly owned ours. Robert dutifully sat on the floor with his legs curled up beneath him like a little girl. He also had a shopping bag with colored crepe paper billowing out. It had the name of a local fetish shop on it. I eyed the bag and wondered what was in it. Actually I was a bit apprehensive over what was in it. What did Mistress have in mind? Respectfully I said nothing about it. When Mistress saw fit to let us know we would find out.

When Mistress and all her girlfriends hugged and said their hellos she turned around and her favorite cocktail was on a silver tray. Tricia held one side of the tray with his right hand and I held the other side of the tray with my left hand. Our free hands were clasped as we pressed our bodies close together. We hoped Mistress would be pleased by our attentiveness but she didn't even smile. She just grabbed her drink and turned to her friends.

Well, the chick flick went off without a hitch. However, Tricia and I were constantly running back and forth for food and drinks. The women apparently delighted in making us prance around on our 5" heels for every little item, separately. The only thing one could hear other than the movie was a quiet, "yes, Mistress", or "yes, Ma'am", and the sounds of our petticoats swooshing when we brushed up against something. Every now and then we saw Mistress Gypsy feeding a small morsel of food to Robert, who remained sitting on the floor in his pink dress like a pet dog. He did not reach up with his hands, but allowed Mistress to place the item between his lipstick covered lips. I do have to admit he is such a cute sissy pet.

The sissies entertain Mistress and Friends

Now the movie was over and one of the women said, "Gypsy is it time for the real show now?" Mistress said, "Of course. Julie, bring out the camera. Remember ladies, they are instructed to do anything they are told, so let's have some fun. Also, if you are not pleased by my sissy boys, you are free to punish them as you see fit." Well, Tricia and I looked at each other apprehensively as to what might ensue.

For the next two hours, the women would have us posing for pictures as Miss Julie snapped away. It was however, Mistress Gypsy that seemed to orchestrate the overall program, like a conductor with an orchestra. One of the other women, I think it was Miss Barb, must be a decorator or artist because she arranged most of the poses as the other women called out what they wanted. After only fifteen minutes Mistress said, "I think my sissies should take off their maid's dresses and prance around in their lingerie for us." The women were gleeful at the idea. Tricia and I unzipped each other's dresses and helped one another to slip off our petticoats as well. Both of us were wearing identical lingerie; ruffled rumba panties, bra, waist cincher, garter belt and stockings, and a very lacy camisole. The only difference was that my lingerie was all black and Tricia's was white. It made a nice contrast between us.

Tricia and I were instructed to kiss one another in many different positions. We had to hug, kiss and caress one another constantly. I was getting sexually excited and could tell that my sissy roommate was too. This was obvious to me when we were made to press our lingerie clad bodies together in intimate embraces. I think the women also knew we were getting sexually excited by the looks on our faces. We were ordered out of our panties. Now we were standing there as two effeminately dressed males with our small erect cocks in front of us. The flash went off again and again. It was humiliating for us both. The women called us fairies, sissies, and pantywaist cock suckers. Mistress told us that she would be sure that all the women had copies of the photos for their albums and that we would be required to have several enlarged, framed, and hung on the wall so we were reminded what sissies we were.

Now the women were so pleased, they increased the rate and intensity of the caressing and kissing between the two effeminate men. We were required to rub our erect cocks together as we kissed. And of course as we two male fairies intertwined our lingerie clad bodies the contrast of our black and white lingerie would be evident in the photos and to all who saw of the whole humiliating experience. Mistress reminded us, "Dear little fairy boys, remember you are not allowed to cum unless I say so." We both gave out a timid, "yes Mistress". Miss Barb promptly slapped us each on our bare asses several times. "You ungrateful sissy bitches, should be more exuberant when addressing your Mistress", Miss Barb declared. Both tricia and I quickly corrected our mistake and responded more exhuberantly and apologetically to Mistress Gypsy.

One of the women had, until now, been rather quiet and laid back. It was Goddess Pagan. Mistress Gypsy smiled knowing what was going to happen next. Mistress Gypsy whispered something into the ear of her pet lap sissy, Robert, then said, "Go fetch, bitch." Robert went into the other room while Florence and I cringed so much that our pathetic little cocks went limp. Sissy robert came back with an arm full of bondage devices from the other room where Mistress Gypsy had them stored. Goddess and Mistress looked at each other and gave one another a big knowing smile. The other women did too.