Dear Auntie Helga,
Miss Gracie B. here again with another observation into the working of the sissy mind and how most intended punishments actually turn into a joyous gifting for the true nanny-no-nuts. Albeit at the same time exampling how a virtuoso Mistress will in turn leverage those fleeting girlish whimsies into a situation where the gifting is in turn utilized so as to present the temporarily euphoric sissy before others in a most humiliating spotlight. One that leaves the nancy so totally mortified that it sobbingly collapses into a deeper depth of emotional emasculation and submissive shaming than it ever thought possible.
A scenario that my ex Lisa played out on multiple occasions prior to her riding off into the sunset with all the fruits I'd garnered during the course of my failed faux manhood, arm in arm with my former best man Peter. The man via whom she not only cuckold me, but the one by which she brought about the adding of the term pansy to my resume of sissified achievements, when she ordered me to my knees on the occasion of their first amorous tete-a-tete for the purpose of fluffing up his manhood in preparation for his pleasuring her. It was during those informative years of my budding effeminacy when she demonstrated the fine art of taking my little smiles and turning them into her big laughs at my expense. Albeit as you will see, if the truth be told, each time it came about as a result of my demonstrating the misunderstanding that I might initiate a return to my former manly ways by pushing back at some injunction on her part.
The prim example, being the one that was the coup-de-grace to my delusions of a return to my macho grandeur of yore, when I rebelled against the notion of my enforced chastity being taken to a new low. To wit instead of the decreed prince albert piercing, which would allow for the scrunched containment of my former seven inches within the one inch miniature encapsulation she desired so that my panties might provide a more feminine appearance, I instead found myself the recipient of a nuclear option. One that left me permanently incapable of ever again enjoying the manly orgasms I once had, as the alternative she devised would render that an impossibility. For while the penal thimble-sized penile incarceration that would have resulted might offer the faint hope of a reprieve someday, the alternative she forced upon me left that a mote point. For the only O's I have these days are not of a spurting ejaculatory nature, but rather the oozing sissy-O kind that occasionally come via a real man or strap-on bearing mistress taking their pleasure at the expense of my bottom.
A final solution if you will which instead of ending with a trip to a piercing parlor, instead found me coming out of the hospital with a more permanent short end of the stick. To wit Lisa's guile and strength proved more than adequate in the face of my refusal to acquiesce on such a diminutive encapsulation, as I awoke to find myself secured to an operating room table with the necessary papers signed, sealed and delivered for the purpose of watching my scrotum slit open and the white testes pinched off into an awaiting metal tray. The sight of which did what the local anesthetic didn't as I feinted away. The second time I awoke it was back in a room where some days later I found out that not only were my family jewels gone astray, but that the seven inches I was so proud of had been shortened in a far more permanent way via a partial penectomy. Such was the extent that only the nubbin knob that once was the proud head at the end of my totem pole was left and that stitched in an inflexible manner directly to where it once hung forth over my reduced scrotal area whose diminutive size was best suited for marbles and not the walnuts I once sported. The result is a button nose type effect, which while it does get flushed a rosy pink at times when sensuously pitter-pattered by a flouncing pair of silken panties, is incapable of functioning as it once did. When taken in their entirety the truncated space and volume that my once manly privates now took up was almost infantile in comparison and would easily be dwarfed if a miniature boutonnière was set over them.
Like so many other sissifying life lessons I've endured I quickly came to embrace the new me however, for unlike the humiliating, degrading and shamefaced thoughts that any real man would have, which I once foolishly counted myself among their numbers, I instead quickly learned to smile at the effeminate emasculated picture I now present for it is obvious I was always meant to be a full fledged sissy and I am ecstatic knowing it. Nevertheless Lisa wasn't going to let me mince away from even this radical change even if she did get the blessing of knowing she had finally put me in the place she desired for me, as she still needed to have that ending course correcting stage presentation before those who thought they knew me, but were about to get a healthy does of a different kind of reality. To wit Lisa arranged for me to do a show and tell of my neutering for a small gathering of about forty family and friends, replete with my having to explain that the earrings dangling down either side of my girlish face were fashioned from my shorn family jewels being bronzed for posterity. A scenario that once again left her with both the last and best laugh as almost everyone else was a gasp outside of my own smiling acceptance of what I'd come to be.
While this was her ultimate work of gilded gelding on every level from emotional to physical it was preceded by many a sissifying shadow being cast over the cemetery she continuously laid my former manhood in. Similar in nature to another occasion in which I rebelled at having my family see me with bouncing falsies, which I stubbornly removed just before they arrived for the party she was throwing in honor of introducing me in my new capacity as her sissy maid in waiting, I found myself as a result of that impertinence the recipient a few weeks later of a set of C size implants which I couldn't discard. Once again however my chagrin at her one upping me quickly turned to joy when I not only discovered the pleasure to be found in my feeling them through my silken nighties, but how much more magnified they could prove via Peter invigorating them when he would run his ample manhood through them on his way to poking me in the lips.
Alas the last laugh was yet again Lisa's, for the makeup debutante ball she threw to out me as her servile sissy maid came courtesy of me serving in a see through bullet bra to the tune of Lisa inviting each of my siblings to do a touchy-feely of their own to appreciate the lengths I'd gone to in order to express my love for my 'true' sissy nature. A rebellious loathing leads to sissy joy leads to corrective debasement scenario that she played out endless times in breaking me into the ninny she declared me to be.
Such as the time she drove me to an appointment at her beauty salon attired in a skirted suit and heels so as to take the long straight hair that I'd kept n a ponytail, based on the image of a rock star I fancied it brought o myself, so as to get it restyled into a soft feathery Farrah Fawcett cut more suited for a my secondary position as Lisa's secretary in the same office I previously had been general manager. Once again my obstinance in refusing to take a seat found me forcibly bound to one instead, as my wrists and ankles were velcroed to a styling chair abutting one of the wash sinks for the purpose of a much more effeminate make-over, but not before I was stripped of my canary waist jacket and matching pleated A-line skirt, along with the flouncy cap sleeved chiffon blouse in a slightly softer yellow under it, leaving me siting there in bra and panties with half slip and nylons all in a pale pink.
The makeover started with a super tight chemical processing on little red rods that engendered a poodle perm with dime sized ringlets that sat high on my forehead and just barely kissed the tops of my ears, courtesy of the little miss bob style haircut reminiscent of the kind the girls in my catholic grammar school used to wear. My somewhat mousy hued locks were than reddened to a deep wine color, replete with pinkish highlights on the curls tickling the back of my neck and the edges of my face. This in turn was complemented by the light rosy pink blush and lip gloss that a juvenile school miss might affect. As I looked in the mirror the younger looking missy looking back, courtesy of the schoolgirl visage that the cosmetology had wrought coyly smiled at the same moment I thought back on those times as a buzz cut willowy kid I had envied in the back of my mind the fact that my twin sister had looked like this for so many year, especially when I reflected on how even then a part of me wished I could be in a perky plaid pleated skirt and uniform blouse, replete with bow tie, saddle shoes and dainty white tulip cuffed bobby socks.
When I was finally freed some three hours later I was informed we would still be heading for the office, however my attire would be more befitting that of my new do. With that Lisa returned from the car with a garment bag containing the essential adolescent little miss party frock one might expect a sissy to be humiliated in before his peers and associates. A dainty pink frock with loads of lace on the ends of the short sleeves and around the neck line with a sash that tied into a big bow in back and three layers of chiffon petticoats undergirding the dress such that once in place the multiple hem lines rose up in unison to assume a horizontal position that placed them in alignment with my outstretched fingertips creating the illusion of a continuous curtsy in process. A pair of pink lace wrist length gloves and pink patent leather MJ's to take the place of the heels from earlier completed the outfit. As I swayed in place the ever growing sissy spirit within me couldn't help but glowing, however yet again Lisa had a major object lesson still in store for me.
To that end given the office was only three blocks from the salon Lisa opted for us to walk there bringing my trepidation quickly to a boil as I found myself alternating between trying to keep my breeze blown skirts form raising up around my head and shoulders while at the same time trying to keep my eyes glued to the ground like an Ostrich in hopes of not being noticed. (fat chance there as many people did double takes with some offering a running commentary once they ascertained my true gender). All of that was nothing however when compared to my speech reiterating for everyone that not only was a truly a lowly sissy and unworthy of the title of man, but I was also forced to admit that my pansy persona had made a real mess of my claims to the general manager's position and that I was now quite grateful to have Lisa step up while I took my rightful place as the lowly office pool secretary... aka errand runner and coffee maker. And if all that wasn't humiliating enough Lisa furthered my mortification when she mentioned her first rule of business would be one of more decorum, especially on the part of the other men in the office who might take a few cues from the new me. Although no one other than myself was directed to curtsy to guests and clients in my greeter capacity. In the end I couldn't complain however as I was living the dream... both a sissy maid and fawning secretary at the same time for a mistress boss who knew the value of keeping me dainty and demure... prim and proper.
On another occasion my opposition to a tattoo of a lavender fairy in flight on my lower belly, turned into so much more as well, when 'Tinkerbell Gracie' was etched over that in a very distinct font similar to Old English Test, At the same time a second artist graced my eyes, lips and cheeks with permanent tattooed on makeup, including dramatic arched eyebrows following the lasering off of the natural ones I had, as well as perky plump ruby red lips that just begged for attention from someone of a randy nature. A very unmanly regimen that found me at the end of a very long trying day required to tip the leading attending artist with an on the knees servicing of my own.
Once again, as with many of these misadventures fostered by my own faltering deceitful male pride, I found myself changing out from the outfit I arrived in, this time leaving decked out in a very dainty two piece nylon and spandex swimsuit patterned in pink and red flowers. One whose waistband of the skirted bottom half was of the hip hugging variety that left nothing to the imagination when It came to my girlish tat. Donned in anticipation of the swim Lisa intended for me to take at the country club where I in the not too distant past had been a noted golfer among the other male members. Needless to say Lisa made sure that those gathered at the 19th hole paid me a visit with ribald humor coming from their lips as quickly as they poured liquid libations back down over them. More than a couple of whom suggested that if I was looking to broaden my service resume I might want to stop off at the locker room to polish their putters for them in the capacity of 'equipment caretaker'. To wit once again Lisa proved that she who laughs last, laughs best, especially given she always made sure she came equipped camera ready for a lasting Kodak moment.
The most demoralizing 3-step process I was subjected to is one whose details I believe the nelly readers of your journal will truly find Giggling-Gertie enjoyable, for who wouldn't like a tale of a girly-boi in a prissy Anime Lolita Sailor-Suit school-uniform prepped to greet the fleet. An episode that started out like so many others with Lisa making a demand that was to the betterment of my aborning sissy nature even if I couldn't see the value to it. In this case the shedding of multiple toys-for-big-boys that had been my pride and joy brought about by her wanting to rid the house of unnecessary clutter, and what could be more of a useless dust collector to a dainty and demure sissified lady's maid then a giant bag of golf equipment as well as several dozen high end fishing poles of varied types, along with a half dozen tackle boxes loaded to the gills. Needless to say they both were the source of all my vacation time pursuits and the endless stories of the glory I'd accrued utilizing them, there was no way I was going to lug them out to the trash as she required of me. You would think I would have learned my lesson when it came to digging my heels in, especially when I am in six inch high patent leather ones, and that I would have at least tried to use some subterfuge in trying to rescue them from going the way of all my male clothing, however I just reasoned she didn't have enough desire to see them gone if it meant digging them out herself.
Once again I was to learn however that getting a temporary joy would only lead to a far longer lasting shamefaced fall on my part in the eyes of others. In this case the three guys whom I first met in the navy, who not only went on to be my best friends and poker buddies, but the core group of the foursome I played golf with at the country club, as well as the trio that accompanied me on many a fishing/camping trip in my former manly man days. All leisure time activities that are symbolic of the camaraderie of masculinity we shared, although in my case they were to find an antithetical club/pole had been introduced to my game in the form of the chastity cage they eventually found in my pantied equipment bag courtesy of Lisa bringing the sissified phoenix out of the ashes of my failed manhood. And although this was prior to my ultimate penile reduction, the inch and a half encapsulation my new persona would be revealed to them in certainly did not reflect my former seven inch gun battleship proportions, but rather left me looking for all the world like a dangling worm in a dainty dingy. A pansy burlesque review that oddly started with a gifting from Lisa in the form of her instructing me to forego my typical in home maid's ensemble for a more 'youthful' sailor uniform, albeit not the kind I'd donned in my seafaring days of yore.
One that was comprised of an old fashioned British navy bibbed style shirt whose petite length hem barely reached the hips, with extended V-neck collar in front turning into a squared profile running down over the shoulders in back, overlaid with a satiny white scarf tied in a loose bow in front, accessorized with shinny buttons on the epaulets, only the buttons were snow white as the piping on the lace shoulder bands, with the rest of the blouse fashioned out of a similar satin of the tie. As for the skirt it fell just short of the knees, with knife point pleating all around and a taut elastic waistband that nipped me in to a adolescent waspish figure. needless to say my undergarment kit was not military grade either, but rather a full length pettislip, ruffled bloomers whose length was such that the lace of the leg bands peeked from under the skirt with every mincing move I made and a pair of knee high socks fashioned from a soft wool and nylon blend in a crochet diamond pattern reminiscent of those worn by prim and proper misses of days gone by, all in a pure as snow white, with the latter shod in navy blue paten leather Mary Janes. A uniform I found to be an odd choice for doing the dusting and other light housework scheduled for the day, however given the way it perked my budding effeminate emotions I blissfully went about my chores.
Around 11 AM I was in the process of dusting the den when Lisa appeared with a small three step stool and light bulbs in hand for the purpose of changing out the chandelier in the room at the same time I dusted it. As I went about the task, having failed to pay attention to what she was fussing with below me, I became unnerved to find that she had not only bound my ankles together with zip ties, but had in turn run others in a manner from that one which bound me to the frame of the stool. At the same time I confusedly looked around while trying to maintain my precarious balance I heard the doorbell ringing in the foyer bordering the den. From my position I could see the center space of the entrance but not the door. I was used to a pair of Lisa's friends dropping in unexpectedly to visit and join in her tormenting of me at times and at first did not think much of it, however instead of their light singsong voices I was greeted by a chorus of greetings in three varying male timbres. Ones which I quickly determined were those of my three friends, Fred, Roger and Kevin. Needless to say I went into an instant panic with nowhere to go given my secured position left with nothing but hopes and prayers she'd send them away. Instead I heard the door close and at the same time I saw their profiles slide into view I heard Lisa assuredly telling them that yes I wanted them each to take a portion of my golf and fishing equipment given I no longer had a use for them. They still hadn't turned my way as I listened to Lisa reiterate that those were my wishes, while at the same time trying to tell them that the reason for my parting with them was that they no longer suited the new person I had decided to become. As their confusion only heightened, brought on by comments of my finding my softer side and a statement that my psychiatrist had helped me come to terms with an aspect of my persona that I'd been keeping in hiding for years called 'sissy-syndrome', she finally said, "Before they went out to the garage maybe it would be best if they came in and saw for themselves and let me explain the inner self I now felt the compulsion to let out".
At the same time she ushered them in she explained a little further, "You see guys, Greg has changed a lot, you will see in a moment but I hope you will still want him to come to fishing camp and encourage him to do so. He may not want to fish anymore but I think you would find him to be very useful around the camp, maybe more so than before. He has taken up cooking and house cleaning and laundry and maybe he could stay in camp and take care of it for you men while you're out fishing and have your meals ready when you get back, the dishes done and all you know. I know you men don't like to do those things anyway." Given they way they looked at each other in a perplexed manner I guessed that this only confused them all the more. I on the other hand felt suddenly light headed, as my heart began racing and my breath caught in my throat, on the verge of fainting over the humiliating enormity of my best friends seeing me attired as I was! Not having seen me in over a month, and that prior to my permed and bobbed locks and tattooed makeup, all three at first had a confused look on there faces seeing what appeared to be a strange adult female in juvenile garb tied in place to a stool with a feather duster in her one hand. However the quizzical looks quickly changed to stunned, as first Roger and than the other two gleaned that it was I.
With that came the shocked rejoinders of the sight before them of "What the F, How come and This must be a joke?" To which Lisa replied, No it is all true and to tell you the truth guys it is not only the best thing for him, but for me as well, for sex with him was no good, no good at all and now I am free to find it elsewhere. Greg's a sissy now guys and you can accept him that way or not, but he really has come to like this new girly side of himself and he's made every effort to be a really good sissy."
At that point Fred spoke what the trio must have been thinking with his simple,"But why?" To which Lisa replied with a snickering glance up at me, "Some guys put up a good front but they are just not real men, at least not real men like you three. You're all manly men but Greg, well he tried to pretend, but he's better off in a dress and doing housework and serving my lovers and..."
It was Roger who then replied with "Wait... what was that about lovers? What do you mean by your lovers?" To wit Lisa, again with a snicker smirk towards me followed by a sincere doe eyed look of innocence towards the trio said, "Look guys you men don't understand how important sex is to us women. We need it and we need it from real men and as such I have found it with others but mostly Peter, whom I'm sure you remember was the best man at our wedding. However not only has it been a mutual blessing for the two of us, but it has also brought Greg and Peter into a closer bound on those occasions where Peter has needs I am not ready to meet."
As the implications of this settled in the look on the three faces changed from ones of concern, distress and wonderment to those of contempt and disgust which only left me that much weaker in my knees and feeling on the verge of blacking out. As such I found myself clasping my sailor skirt for support, but instead found myself presenting the appearance of a curtsy to the three of them which added mocking scorn to their eyes. It was at that point that Lisa played her 'correction-card' announcing that in addition to each getting a portion of my now redundant male sporting trinkets that she would like them to compete for the honor of being the one of the three who can show her his version of manly in a sexual sense. Something that garnered their immediate attention and although they all seemed hesitant once the rules of the game were revealed, the provocative pose she offered as she playfully made a point of touching each of them in an intimate place, soon had them rethinking. For it was to be a contest to see who could last the longest while a beneficiary of my oral services. A pronouncement that quickly had each of them stating things like the defense of their manhood and that they wanted nothing to do with a pansy fag like I'd revealed myself to be, However Lisa quickly assuaged those concerns by pointing out that there wouldn't be anything gay about it given I wasn't a real man, but just some simpering third sex pathetic creature who now goes by the name of Miss Sissy gracie B.
I'll spare you all the on my knees details, but suffice it to say Kevin the Irishman in the bunch face pumped me the longest. So that in the end my manly toys still all went out the door in the hands of what were now my former best friends, I had paid a mulligan of being a sissy-sally to the fleet, and most importantly Lisa got a double last laugh retribution for my being uppity over complying with her wishes that I put to trash the remnants of my failed manly past. For not only did I have to listen to my friend Kevin enjoy the pleasures of my wife in my own home, but a few weeks later Lisa made good on her promise of sending me to their fishing camp with them in full French maid garb and an overnight bag replete with two sets of baby doll nighties especially designed with a port-of-call slit hole in the rear of all the panties accompanying me. A tale for another time, although I can assure you that some of the contests they devised that weekend, including fish whoppers of another kind, were not of a singular nature for we wound up rebonding group-wise on several occasions as one would expect 'dear-old-friends' might. Thank you as always Aunt Helga for this chance to hopefully both enlighten and delight at the expense of my ever expanding effeminate emasculation.
Forever yours in Little Girl Dresses and Tight Curly Tresses,
Miss gracie B
Thank you for your letter Sissy Gracie. As most regular readers of our little magazine will recognize Gracie is a friend of mine and I have had the privilege of publishing many of her sissy ramblings, I had asked her to tell us about some of how she came to be the person she is today and to relate some of the special treatments her very dominate ex-wife used to help her realize her full potential. I hope you enjoyed the read.