A Tale of Two Sissies



On one beautiful summer’s day, early afternoon on a Friday, the clouds cleared as the sun came out, and as the shimmering light shone through the larger windows of an expensive home. The serenity of the scene was broken by the sounds of a demanding yet beautiful and statuesque blonde.


“Now Cindy, get your sissy ass in here.”


“Yes Mistress,” Cindy submissively responded, scurrying nervously into the room, stopping with a sudden halt, curtsying, her knees pressed together, eyes cast humbly and submissively downward, past the all too short hem of her petticoated pink maid’s dress, trying to see past her puffy petticoats to her pink patent leather pumps, covering her pink stockinged feet, her 1960’s style blonde bubble hairdo with big bangs and the pretty big pink bow above her bangs, hanging slightly downward.


“Seems to me someone’s been a naughty sissy girl today. . . “


“Yes Mistress,” the sissy chillingly responded.


“I’m thinking that while you’re supposed to be enjoying the privilege of working hard and cleaning my home, your attention wandered and you were listening to my phone calls, not only the one with my lover, but the other calls to my girlfriends telling them about my date last night. Were you eavesdropping again you little sissy? No excuses, did you hear my conversation?”


“A, um, I’m sorry; I tried not to listen but. . . sissy couldn’t help but overhear, sissy was so nearby, and I, I, um, sissy guess so, I . . . “Yes Mistress,” Cindy finally admitted dejectedly.


“It seems to me that someone’s little sissy girl needs some correction and obedience training, don’t you think? So Cindy, quickly run upstairs and fetch some of my correction tools, I think the strap and Ms. Hairbrush would work here very well in correcting you, especially before all Ladies arrive here this evening for my party. It’s important I set the proper tone for you sissy.” Waiting as trained for Mistress’s final word in her sentence, Cindy quickly curtsied, and scurried up the stairs at top speed in her high heels, to fetch the demanded instruments of training and correction as per her Mistress’s orders. Scrambling back downstairs, the sissy quickly curtsied, then knelt down, with arms held high over her head and palms holding the instruments of correction as required, looking down on the floor as trained.


“Well . . . .?”


“Please Mistress correct me very hard, strip away any and all unsuitable things, such as any remaining maleness and train me to be the best little sissy girl in the world! Dearest Mistress, this little sissy wishes only to serve you and all Women, my superiors, whom I joyfully serve with all my love and all my heart.”


“Well then you annoying and disrespectful little sissy,” as she reached past Cindy’s long hair gripping her ear, and lifting her to her feet, “it’s bend over the couch, skirt up, panties down, and reeducation time again,” as Cindy’s ankle’s were kicked apart slightly. “Don’t to have something to say?”


“Yes Mistress, please Mistress, re-educate me very well.”


“Oh, don’t worry your silly, pretty little head about that Cindy; I’m a firm believer in your education.”


With that, Cindy’s tearful reeducation began, ending in a very red bottom and a face full of free flowing tears, later followed by an hour of on tip-toe, of shoeless corner time.


While she obediently stood there, with a steady stream of tears flowing down her face ruining in her makeup, Cindy looked down to her now very real C cup breasts, one size smaller than Mistress’ and wondered how a fantasy once dreamed up during her very early adolescence, could have ever gotten this far. As far as she could remember, being dominated by Women and feminized by them was her earliest and most intense lifelong sexual fantasy. How many days and nights, Cindy had dreamed of being a Female, of having grown up Female, of having gone through life as a Female, having gone to school as a Female, having puberty as a Female, and in her dreams at night, of looking down through her eyes and at Female body, breasts, a flat Female’s stomach and naval, an appealing feminine mound were pronounced split labia down below, only to wake up disappointed and frustrated to see her maleness, if you could even call it that, still disappointingly there.


Maybe it was the fact that this fantasy of hers, once his, seemed relentless and ever running throughout many of the thoughts each day - maybe it was the naughty nature of these fantasies that were so compelling - perhaps it was the desire to realize these fantasies - perhaps it was the insistent nature of this Woman, who would sexually tease her, playing with the genitals, keeping her on the edge, while repeating, “ I want to know your fantasies, tell me, tell me, no relief for you until I know. This Dominant Woman, once a girlfriend, later a wife, then a husband, now a Mistress after their legal divorce, without any real interest in breaking up, who made Cindy sign over everything, having Cindy sign a slave contract she found on the Internet and adjusted too suit her needs, who had Cindy’s name legally changed to Cindy, and her sex legally declared Female, by an insider within the courts, now a former lover, and now close personal old friend, and once in a while infrequent bed partner. Cindy’s Mistress, a beautiful and dynamic Woman and a real leader, who remained interested primarily in Females as conquests and lovers, and who still had a once in awhile occasional fling with a stud, just to keep things interesting, that drove this life into reality around Cindy. One thing was pretty much for certain, Cindy would never actually realize the fact that this once he, now a she, for all intents and purposes, was chosen for her noticeable sissy streak, and possibilities for sissy development, which her Mistress decided to promote and cultivate as a part of her own needs early on.


So much had changed for Cindy, her mind wondering back to the days when she was a sort of big man on the college campus, thought of as a big man stud by all of those people who didn’t actually know of her secret desire to become a submissive sissy and dominated. Nor did they know the secret of sissy’s tiny under endowment, which sissy would keep carefully hidden away from the locker room boys and how Cindy would only use the restroom in a stall in the seated position, keeping this embarrassing secret to herself. But this Woman, this Dominant, this Mistress, did know all of this while dating Cindy, turning Cindy on, keeping her frustrated, breaking down her will and generating deeper submission, often joking about Cindy’s ever-increasing sexual frustration vs. Mistress’ sexual fulfillment, then getting Cindy to beg for sexual favors, first begging to perform, then having her perform oral sex for Mistress, giving her Mistress head in the back seat of cars just like many girls did for the boys. Many times Mistress would leave herself just a bit dirty, after many trips to the Ladies room, to get Cindy addicted to the taste of her dirty pussy. Later this evolved into Cindy being used as Mistress’ feminine urinal indoors and sometimes even outdoors especially at night in public places. More and more, how Cindy craved to submit to become more and more submissive and feminine to please this young Dominant Woman, her love, her boss, the center of her world, her Mistress.


Hearing footsteps in the hallway, Cindy snapped back to what she had been trained to think about, what she had been doing wrong, how as a sissy, she needed to try harder and harder to not offend and to serve at Mistress’s whims better and better, how she should feel bad about even the possibility of disappointing Mistress, how she should work even and harder to correct all things objectionable to her Mistress, as yet another wave of feminine hormone induced tears, began to flow emotionally from Cindy’s eyes, further ruining her makeup, and making her deeply desire to submit further and please her Mistress even more.


Two quick claps of Mistresses hands signaled that Cindy’s corner time was over, and it was time for Cindy to shower, reapply make up, fix and sissify her hair, change into fresh sissy undies, don her pink formal sissy serving uniform, answer the door and let in the caterer, make sure all things were set, run upstairs and assist Mistress in her bathing and dressing, and the downstairs promptly at 6:30 PM to greet Mistress’ guests as they arrive.


This evening’s event was what many in the Lesbian community called a fish party. In the strictest sense, that usually meant Women only, but in this case it had evolved into guests who are Women and the occasional former men in their lives, now sissies in tow, and on a once in a while basis, the occasional well hung stud for servicing purposes, for the Women in attendance who still enjoyed this sort of thing. For all intents and purposes this party would seem like a normal social event, until 10:00 PM, at which time, those who wished not to participate in the orgy-like atmosphere, could respectfully go home, while all the rest, would strip down as desired, for the evening of the realization of their most intense and enjoyable sexual pleasures. Of course at this party, all would stay and enjoy.


Cindy’s redress went quickly and well, as Mistress had told Cindy which clothing to wear for the evening earlier that day. Dressy pink maid’s mini-dress, a pink bra with matching rumba panties with very tight gaff of course, flouncy petticoats, pink garter-belt and stockings, pink high heels, which matched Cindy pink finger and toenails, perfume and sissy makeup, made Cindy the picture of overdone sissy femininity.


The caterer having seen Cindy so many times before was completely unfazed by Cindy’s overly feminine sissy costume. Cindy thought to herself that there seemed to be quite a bit of food being delivered, some of it cooked, some of it uncooked, some of it for dinner, some of it for what appear to be a brunch that would have to be prepared. Cindy the thought to herself, “I am my Mistress's sissy-servant, she always tells me, mine is not to reason why.”


After completing her duties with the caterer, Cindy quickly put on her rubberized bib apron, softly knocked at the Mistress bathroom door, and was granted entrance by Mistress who was already relaxing in the tub, having drawn her own bath, which worried Cindy just a little bit, for fear of future punishment. Cindy massaged Mistress’s feet and back, and assisted in shaving Mistresses legs and underarms, as well as Mistress’ pussy area, which Mistress liked to keep clean shaven for better orgasmic stimulation. Cindy helped Mistress stand and helped pat her dry was a big fluffy towel. Next was off to help Mistress get dressed. As her breasts were strong, high and perfect, she decided to forgo a bra and simply put on a see through top, a garter-belt, sans panties, with her newest designer strappy pumps. Cindy actually felt for the first time in a long time, a twinge of sexual excitement, apparently just an echo from her past self, as Mistress had recently had been discussing with her friends the possibility of having Cindy fixed, and unbeknownst to Cindy, planned on showing off Cindy’s newest alteration to the Women attending some upcoming party. The rings between Cindy’s legs that forced her sissy wee-wee backwards between her legs, which forced Cindy to pee sitting down like the feminine creature she was evolving into, just as she had done some months earlier when Cindy’s breast implants were done. Mistress, a Female Supremacist, knew that in this age of burgeoning re-enlightenment for Women, such displays were not only educational but also a triumphant turn on. Cindy, being not a true and complete real Female, was at many times unaware or incapable of understanding, or confused emotionally enough via her new and raging feminine hormones within her blood stream, to have any understanding of what was going on around her sissy self. While putting the final touches on her outfit, Mistress reached up under her own skirt to find the thoughts of this evening’s festivities were making her wet. She reached down and raised her skirt laid back on the bed, and ordered Cindy to orally pleasure her, not to completion, just enough for a bit more stimulation. “Lick Cindy, love me like a girl.” “Yes Mistress.” Cindy as trained, eagerly and obediently pleased and pleasured, knowing just how Mistress liked it best in this situation. Okay Cindy, mmmmm, that’s feeling so good, maybe I can have just a little come right now, ahh yes cindy, right there, just like that!


Upon completion of Mistress’ cum and cool down, Cindy rushed two washcloths one wet to clean and refresh and one to dry. Mistress upon rethinking the situation in combination with her excitement, she ordered Cindy to fetch her newest and hottest drawstring thong, which she was quickly placed into.


Now done, and smiling, Mistress arose using the top of Cindy’s head for leverage. Mistress decided before leaving there was still time for a little more time for the verbal re-education for Cindy.


“Cindy, you’ve come so far, I’m so proud of what I’ve done to you and what you have become. Do you remember years ago when you try to pass yourself off as a guy, even a stud? Just imagine, a sit to pee stud with a tiny tampon sized mini-wee-wee like you have, what a scream!” as she broke out into hysterical laughter. “if those girls could see you now! As I’m thinking about it though, we do have a reunion coming up about five months from now, don’t we? Hummmm, I’ll have to get us some tickets for that. Do you remember years ago when I first changed your name to Janet, and then to pussy, and finally Cindy, I think I made the right choice don’t you? Do you remember how I made you beg each time to hear what name I came up with for you? Do you remember as well, how I had you beg for your breast implants and how hard you’ve been begging and crying when I ordered it, to have you fixed? Won’t you just love your tiny and empty sissy bag? I know I will! Your tiny sissy bag will go so well with your tiny sissy wee-wee! You do seem to love begging don’t you sissy? Isn’t it great you’ve been able to realize your dream, of being a Dominant Woman’s sissy submissive and obedient feminine sissy maid?” “Don’t you just love being feminine and submissive, dressing pretty and obeying? Don’t you just love stepping out of the shower and seeing your beautifully large very feminine breasts? Don’t you just love looking down and see a nice feminine vee in the front of your panties, now that I’ve had you ringed?” I know for a fact that you simply adore your bra and panties, don’t you remember a few weeks ago when I told you as punishment that I was thinking about putting you back into boy underpants and how you just cried and cried and begged me not to, how you love your panties so and how you’d do anything to keep your panties, awww, I felt so sorry for you! And we both know you need to wear a bra these days, as well as all the other feminine items like your dresses and your skirts and all the pretty things you wear, most especially your nighties and feminine briefs in bed at night, and your sweet smelling perfume and your makeup. Don’t you just love the way your body is changing, finally you’re going through puberty as a girl, well sort of, anyway, more later on that, good for you! Don’t you just love the fact that I get to victoriously have all the sexual fulfillment and pleasure I want, wherever and with whomever I want, while you’ve got to wait and learn and beg me to obey, to submit, to be humbled, to be humiliated, to be defeated, to surrender, to embrace and enhance your femininity? Haven’t you just loved the way we both have crushed any and all of what little manliness you once tried to fake out of you? Not much of the old sexuality here anymore is there sissy bunny, well . . . I for one am happy and delighted to say, bye-bye to your little maleness, bye-bye, and good riddance, I’m glad you’re gone! One of the very few things you were so right about, was the fact that you should have been born a Female. One other is that you needed a Dominant Woman like me to shape and mold you into what you are becoming, and really deep down, you have to admit, have always been, my sissy toy plaything- isn’t that right Cindy? In fact you truly love being my pussy-whipped, fixed sissy girl creation, don’t you little girl?” “And we both know how eager you are for my dildo, don’t we little girl?” As she had been trained to respond and she always did to such questions, as beaten sissy she is, her response was a resoundingly weak, “Yes Mistress,” with her made-up eyes properly and humbly downcast.


Happy and laughing at her sissy once again, a continued source of amusement and laughter for her, a sissy who was certainly now further and completely molded and beaten down into proper submission, Mistress truly now happy with herself, drifted downstairs to relax before her social event. As always Mistress had a few surprises up the sleeve of her see-through blouse for Cindy, a few guests who would fit right in at this party, guests sissy hadn’t seen in quite a long time.


About fifteen minutes before the official start of the party, the doorbell rang. Cindy curtsied to her Mistress and quickly ran to the door to open it. At the door was Mistress’s current lover, Carrie and standing behind her, as a once proud husband, now ex-husband and now, also a feminized sissy maid, was sissy Tina. Tina’s transformation had begun just a few months before Cindy’s transformation. Tina’s new name had been arrived at by the Women, as an extension of how under-endowed she had been years earlier when she tried pretending to be a man, originally they were calling her, Tina with the tinnie wiener. More work had been done on Tina, her face looked like that of a teenaged girl, and Tina also had more experience in being exposed, humbled and humiliated in a feminized state in public to both men and Women alike. Even with this experience, Tina was blushing furiously. Carrie cheerfully sweeping by Cindy inquired, “where is your Mistress and my lover? I can’t wait to see her.” Bobbing a deep and a well practiced curtsy, in a high pitched well practiced feminized voice, Cindy responded, “good evening Ms. Carrie and sissy Tina, Mistress is a waiting your arrival in the main living room, please follow me.” The Dominant Female blew this off, saying, “I know where the damn living room is sissy, out of my way. Baby here I am!” As the two lovers embraced, sharing a deep passionate French kiss. The two sissies stood just inside the archway to the room hands clasped in front of them, heads bowed, eyes downcast, awaiting orders. “Corner time sissies, while we Ladies get reacquainted.” So off the two sissies went to a corner, as ordered, until Ladies were done greeting one another. The two sissies were quite a sight to behold, two feminized Sissy maids facing the corner rigidly, in submissive obedience, heads down, legs pressed together, Cindy in pink, Tina in yellow, hands behind them, dresses and petticoats held up high, to expose their lacey rumba pantied bottoms, as their two Mistress’s, lost in a sea of sexual passion, yet happy, contented and confident from the results of the training. These two ex-males, formerly drinking buddies, now just feminized extensions of their Mistress’s will, feminized creations and obedient sissy servants.


After just an all too short few minutes kissing and some light fingering, two lovers came up for air, and addressed their maids. “Sissies Cindy and Tina, front and center,” came the order with a double clap of the hands, from Cindy’s Mistress.



“Cindy, you will be our official greeter to door when the guests arriving. Tina, you will assist Cindy by taking our guests bags putting them away. Once our guests are settled in, you’ll fetch drinks and serve food has ordered like two good little sissy maids. Also of course, as a regular part of your duties, should any Woman here require more personalized service, and you know we mean, whether being assisted in the Ladies room, with dressing and undressing or with wiping after one of us pees, which many of them still consider a luxury, but as your two Mistresses here right now know that a day to day thing here, or should any Woman order a little oral pleasure or anything else within reason, your main focus is to obey, to serve, to please, and to pleasure in the sissy ways you do best. Is that understood?”


In high pitched harmony, with two sissies chirped out, “yes Mistress!” and curtsied simultaneously. “Now sissies, isn’t it time you properly greeted one another?” This was the part the two sissies dreaded the most, as they turned to each other to plant a deep, longing passionate French kiss into each other’s mouths, like a long lost lovers. Even though both of these sissies, bore very little resemblance to anything masculine, in the backs of their minds there was still some very fading hope of returning to a more masculine existence, even though that was never going to be. The Women laughed and clapped at their antics triumphantly.


Now the doorbell rang again, as more guests were arriving, in the two sissies scampered, to answer the door has trained. Frightened yet in position, Cindy and Tina positioned themselves to open the door. Cindy’s jaw dropped in complete disbelief at whom she greeted at the door. It was Women from her college days, she had not seen in years, Mistress’s high school and college girlfriends, of which Mistress had always sort of been the leader of the group. In her college days, these Women would come on to the male persona that Cindy once was, flirting with her, getting her excited, seeing her as macho and very manly, little did Cindy know that these were to be the guests of Mistresses party. Two decades later, Many of them had been married and divorced, all of them had given up on men with the exception of the occasional stud for recreation purposes, all of them now accomplished and successful, all of them now Female Supremacists.


The first one and was Jenna, a strawberry blonde, who really blossomed since her college days, into a stunning knockout. Back then she was always more or less the most sexually active of the bunch, having sexually enjoyed over six dozen boyfriends and secretly just as many if not more girlfriends as bed partners in the 4 1/2 years of college she attended. Jenna had grown not only to see Women as the superior sex, but also to see men as easily manipulated weaklings that most of them are. She by trade a plastic surgeon.


Next in were Sandy with dark straight hair and hazel eyes and Mandy with dark very curly hair with blue eyes, two Hispanic girls who looked a lot more like sisters than friends. Mandy had been married to a drunken loser, the dreamer who never got anywhere in life, whom she had dumped just before a large family inheritance was received. Sandy on the other hand, had come out of the closet early as a Lesbian making no bones about her choices in her life, and as fate would have it, these two have been lovers for the last eight years or so. Sandy had made plenty of money in the futures market, both were as very well off as they were the able to turn heads and stop traffic with their bodies. Last in was Heather, always the sort of a lot odd ball of the bunch, who now dressed in black leather every chance she had, been kept a stable of both Female and male stud slaves, working both as a psychological counselor and dominatrix.




two sissies, part 2




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