Dear Sissy Jane

by Sissy Gray

 

Dear Sissy Jane: Thank you for your delightful letter. I can truly emphasize with your situation, as girlfriends can be quite cruel in their love when they have their man helpless in skirts. As I write this letter to you I am abiding just that, for I am also under the guidance of a 'girlfriend' in my life, albeit this one is my former wife's paramour, my sister Patty.

They not only work together, along with Lisa's sister Cindy, but share a more personal relationship also, as Patty took over when I was expelled from my ex-wife's intimate affections. So as I write this I do so under the auspices of sister dearest, who having taken the liberty of reading your letter, as her and Lisa have done to so much of my life, she has instructed me to give you a mini synopsis of my prior life.

As with your own situation the two of them keep me in an array of punishment panties, expanded however to include other female accouterments. Unfortunately they have taken them out of the privacy of the bedroom, where I had intended them to stay, and brought them into the public arena. This as a result of the two of them insisting that I pay them back for all the lessons in feminine deportment they have provided, and the prissy tight curly perms they keep me coifed with, by acting as an assistant in their hair salon when I am not at my own office.

As such I find myself bedecked each Saturday morning in some flimsy little dress, always pastel and often quite juvenile, usually accessorized with a puffy slip and shiny Mary Janes, for the express purpose of being used as their go-for/shampoo-girl.

As their shop is only a few towns over from my own business, and is visited by many residents of the community, this can be very stressful. However no where near as bad as the ordeal I now face each weekday at my own office.

You see to keep me in the proper frame of mind for my weekend moonlighting, Lisa has also altered my work-a-day office attire to include very chic business suits, many in pastel shades of polyester, with nipped waistcoats and very billowy wide legged slacks. These are accessorized by patent leather flats and obviously feminine blouses, utilizing silky scarves for ties.

On occasion they'll even trade off the girlish pants for a colorful skirt, under the excuse that they're helping me express my Scottish heritage. However the 'kilts' they provide for me to wear are not anything like the real deal, which I have worn for years at family and clan gatherings, but rather just a slightly shorter wool skirt, whose pleats running the full circumference pronounce it for what it really is, a girl's dance kilt.

Sadly (well somewhat) all of these recent adjustments to my persona fly in the face of my historic visage. While I had dabbled in softer undergarments, if you will, my entire life and enjoyed occasionally mixing them with my family kilt, I have always been a rugged type of guy, who enjoys soccer and baseball and the kind of macho men who participate in them. I used to even teach kickboxing and had a reputation as a man's man. All of which has changed gratis of my two 'mistresses' machinations.

 

These dramatic changes from my former manly ensembles, which constantly provide my office staff with many a good laugh at my expense, have certainly eroded my stance in the community as well. The only good thing is that our business is not one frequented by many visitors, however as my appearance has changed so has the perspective of the very people whom I pay. I have even found myself sometimes functioning as my secretary's secretary, as my somewhat ditzy attire has not only altered their perspectives, but it has affected my performance as well. Such that where I had previously been resolute in my control, I now find myself relying more and more on Mary, my secretary's helping influence, in the midst of one of my more frequent 'blond' moments,

As I write this letter to you I find myself literally chained to my office chair. My own punishment panties are quite pronounced as they are afforded no covering by the gossamer baby doll nightie, whose short length and petite puffy sleeves do nothing to hide my hairless arms and legs. Accenting the perky pot of curls gracing the top of my cringing head is bobby pinned a sicky sweet, pink, satin bow, which matches the smaller one on the waistband of my lacy rumba panties.

Loose panties, which are further ballooned out by the raging hard-on nestled in their soft silky folds. Like yourself however this is more of an affliction then an affection, as it is engendered by a matching pink satin bow, tied in an excruciatingly taut knot around my smooth hairless scrotum.

 

Between that and the large vibrator wedged into my backside, which is pushed unmercifully hard against my prostate by my own seated form, I find myself in an engorged state with no relief in sight.

With that as a background I put to paper this overview of my past. While the story 'Dresses and Tresses' which you have already read is just an individual segment from my personal history, this missive is more of an encapsulation of the entire scenario, although the story I'm working on that I mentioned in my previous script will be much more definitive. Nevertheless I hope you enjoy hearing this little ditty, as much as my leering mistress enjoys promoting the telling.

As I look back I guess one would have to say, that while my current predicaments are of an unrequested nature, I realize that they were in truth birthed in my own effeminate soul. In so doing I come back to warm memories of early times spent in my mom's forties and fifties June Cleaver like outfits. Although truth be known I think I was a little bit peculiar, in that when so attired instead of playing house, like I've heard so many other vestment challenged young men would do, I instead would slip out the back door and go for swishing phantasmagorical walks in the nearby woods, or even stranger yet, go out back and play baseball by myself. I guess I just couldn't decide whether I wanted to be a mix of Denis the Menace and Davy Crocket, or pretend I was a prim and proper Our Miss Brooks, catholic school girl. This later coming courtesy of me and my sister being quite similar in size, so that I was able to 'borrow' and fit into, her pleated St. Mary's uniform skirts and jumpers.

An idea which was germinated in my head whilst I was in the fifth grade. That year one of the nuns decided that a suitable punishment for boys who were disrespectful of any girl, but especially of proper St. Mary's girls, was to give them a taste of their own medicine. To that end the rowdy culprit would get to spend one to three days seated in a chair located right next to the good sister's desk while bedecked in the female version of the school uniform. This in light of the many young hooligans who found it sporting to flick up the back of the girl's skirts whenever they were bent over, especially in front of their lockers while under the observation of multiple viewers. All for the purpose of a humiliating panty exposition.

This corrective action seemed to have an immediate sobering effect upon any young man so punished, but for some strange reason, which the nuns never could understand, young Gregory was quite recalcitrant and needed to be so chastised on several occasions. I think the only thing that kept it from becoming a somewhat permanent state of affair was the subsequent beating with a belt, which my dad gave to any one of his kids who got in trouble and brought dishonor to the family name.

From that inspiration however I developed one of my favorite pastimes, which was to put on one of my twin sister's school uniforms early each Sunday morning, and steal away to 5:30 AM mass. It consisted of a checkered navy blue and white kilted skirt, along with a white rayon blouse and the matching plaid school bow tie. This was finished off with her white nylon knee socks and my own black and white patent leather saddleshoes, which were my pride and joy.

I'd then walk the one mile plus through town to the parish church, with no one the wiser to my knowledge, thanks to the cover of my Robert Hall's black raincoat, which hung down almost to my ankles. This would leave only my Buster Brown cordovan brogues and a hint of sock showing below its hem.

One of my biggest thrills came from sauntering along in the breeze, as it would push apart the flaps of the coat and stir the pleats of the skirt around my youthfully smooth thighs. I would add to my effeminate joy, and make myself feel extra girlish, by wearing my sister's perky navy blue school beanie on my head, right up to the edge of the parking lot of the church.

As the only other people who regularly went to that early service were the elderly widows in town, I was usually able to go there and get back home before the rest of my family was even up, typically without so much as a comment along the way. The only time that I even came close to having a problem came while I was kneeling in one of the pews. Coming along one of the good sisters questioned why she could see my socks and not my pant's cuffs.

I quickly told her that I was wearing shorts, as my mother hadn't done the wash yet. I remember well the sudden fear I felt at the possibility of having gotten caught, as a look of suspicion crossed her face, however she only reprimanded me with a painful twist of the ear, whilst admonishing me not to be so irreverently attired in God's house.

 

I guess it was this early boldness which eventually led to my getting in over my head a few years ago, not to mention the sudden demise of my marriage and my subsequent outing at my wife's hands, as reflected in the subsequent events. A montage of the various times my ex-darling has made a show and tell nightmare out of my duel nature.

We first met in college, where we shared an attitude of enjoying good times and being free spirits, albeit Lisa's was not so unchained as my own. Along the way Lisa learned of my previous dalliances in skirts from my sister Patty, who had finally caught me one day while slipping in the back door. An event which when repeated a month gave my sister the hidden ammo she needed to bribe many a favor.

Unlike my sister, with whom she had become a good friend, Lisa just chucked up my skirted soirees as a passing youthful phase, never addressing the true disdain she felt over such matters until it came to a head several years later.

After some early wild years, in which we tried just about everything, we finally settled down to a fairly mundane existence. Throughout most of that time I kept my preference for the softer things in life a secret, having noticed the way Lisa would visibly bristle whenever something of that nature came up around us, be it in real life or on the silver screen. It was almost as if she felt challenged over the whole issue and that she was daring me to wax nostalgic about the one college faux pas, (as she would reference it), which I had during that period of time.

This was a brief experiment on my part with a friend, and fellow soccer teammate, who similar to myself, liked to 'skirt the issue' as we would say. We had first discovered each other's interest in non-bifurcated clothing at a Highland Games event the summer before, at which time each of us had on the kilt of our respective clan's tartan.

Nothing really came of this however until the following fall when I spotted the hint of something lacy caught in the zipper of his team travel bag. Managing to get us assigned a room together for a three-day, two-game, university away trip the following weekend I planned to check out my suspicions.

I was able to ascertain that very first night, via a clandestine investigation of his bag whilst he was in the bathroom, that what I suspected was true. A short time later I confronted him with an, 'I'll show you mine if you show me yours' type scenario, courtesy of my own little nightie which I had stored away for just such an incase.

Before the night was over we had become the closest of friends in every sense of the word, although our relationship became purely plutonic once the little Mrs. caught wind of the issue. While she never had any proof positive of our sexual tete-a-tete, she did her best to keep us separated, whilst suddenly blessing me with an overabundance of her own passionate charms to keep me on the straight and narrow.

For that short period of time before hand however Billy and I became like a pair of randy lesbians, frolicking together in our sundry silk and chiffon finery, whilst exploring each others budding femininity.

I never thought of myself at the time as being gay, although the two of us would kiddingly refer to one another as flaming faggots, whenever either of us would say or do something unmanly. All in all it was one of the most liberating periods of my life, which in hindsight, sadly came to an end all too soon.

The same could not be said of my relationship with Lisa however, for in the years since that time, her propensity for rewarding my wayward nature with her passionate pleasures waned, but her constricting control over my personal dress code never wavered. She construed the definition of acceptable attire for me to best reflect the image she had created for her own persona. She even went so far as to refuse to get together with the members of my family if it was going to be a clan event.

Unfortunately for me, some might say, my libido kicked into hyper-drive a few years back and I felt it was high time I started exercising my inalienable rights to dress the way I chose, especially in the privacy of my own home. A point of view however, that the usually liberal Lisa had a very staunch conservative perspective of.

This led to the two of us fighting tooth and nail over the issue whenever it was brought up. She would question my manhood, while I would question her once free spirit. Each time it would end with me pushing the envelope by my expressing myself around the house in some feminine way, courtesy of a sequestered makeshift wardrobe compiled from Goodwill, Sears and Filenes' Basement.

Finally, in the face of my renewed youthful boldness and my more frequent taking of liberties in my choice of attire around the house, Lisa seemed somewhat compelled to capitulate on the matter. Although I should have been warned to the contrary by the smoldering glances she would afford me with her eyes each time I did so.

Why I didn't realize from past experience that she could be a fury to behold, and that in actuality I was in the calm before the storm, I'll never know. For in truth hurricane Lisa was about to blow.

It culminated late one afternoon, whilst the two of us sat together in our favorite watering hole with her sister Cindy, that Lisa in an apparent about-face seemed intent on bringing the whole matter to a head. After a heated round of conversations in which it appeared I had acquitted myself quite admirably, to the point of even gaining an apparent ally in Cindy based on her favorable comments over the matter of men in skirts and dresses, Lisa was visibly livid. With all of her points of view seeming to have come up short she then played the integrity card. She sarcastically questioned why, if I really was the rugged manly individual I claimed to be, I didn't express my new found fashion freedom wherever I went, instead of just subjecting her to my whims.

Without really thinking about how I was putting it I answered it was only her reticence about how I appeared to others, and how it might reflect upon her, which kept me from being myself and dressing whichever way I wanted, and certainly not any inherent fear on my part.

This was all said with the thought in mind of wearing my kilt more often or maybe even being a little more daring with other unisex type apparel, never thinking in terms of publicly exhibiting the more frilly or diaphanous items I had worn of late at home. I was to quickly learn the hard way however, that what I intended as subtle expressions of my second nature, Lisa would fully exploit for her own purposes of revenge, but not before she put her hooks in my jaw so to speak.

After much further ado on the issue, in which it appeared Lisa was going to continue to be resolute, a.k.a. pig-headed over the matter, she did an abrupt about face. She only requested that if I was going to proceed with my little bouts of 'dress up' as she put it, that she at least be allowed to guide me on how I put things together, so as to keep me from embarrassing myself, and her along with it.

Thinking that I had finally won, whilst inadvertently ignoring the implications that 'embarrassing myself' implied, I jumped at the chance and exclaimed that any assistance in helping me pull things together would be more then welcome. To that end the two sisters, who are hair stylists and cosmetologists by profession, offered to give me some pointers and a trial makeover.

Thinking only in the terms of my own plans, I let the drinks I had been imbibing do my talking for me, as I excitedly agreed to let them have as much say in the matter as could possibly help. I guess in the back of my mind it went without saying, that any flamboyant or effeminate expressions of myself would be discretely limited to the privacy of our home. An assumption which all too soon, as the saying goes, was to make an ass out of me.

After another round to seal the deal, albeit coke for designated driver Lisa, we headed home for dinner. As we went to leave the two sisters excused themselves for a moment to use the lady's room and have a quick private girl-talk. Unfortunately for me I failed to notice the evil grin the two shared upon returning as they thought of the diabolical plan they had just hatched.

Along the way over to drop off Cindy, as we came up to where their salon was, Lisa, running her hand up my leg, suggested that it being Friday night that her and Cindy give me a taste of what I might expect.

Thinking only in terms of my possibly having a frolicking good weekend at home, I said, 'Why not'.

Those two words in the long run have harshly closed some doors for me and joyously opened others, as the girl's makeover that night was anything but subtle. Radical would more likely be the word, as the earlier ideas discussed for minor hair styling alterations and the proposed light facial makeover, became life-altering changes instead.

By the time I left their shop that night, the suggested slight trim of my ragged split ends, along with some soft curly waves being added to my pin straight hair, gratis of a few large rollers and a curling iron, had denigrated instead into a short sassy-do. For while I had drunkenly stumbled in with shoulder length straight hair, I shyly walked out an hour and a half later with tight little curls bouncing like a shimmering halo around the edges of my ears.

What had once been one length hair now sloped into a distinct tight V high on my neck, trailing back from the narrow school boy whitewalls clippered in around each ear, while the front was now graced with prissy bangs, the likes of which I had never had before. A feminine row of short wispy looking curlicues sitting high atop my forehead, making for an overly effeminate Caesar cut, which puffed up with every movement of air.

In addition to Lisa's radical changes to the style of my hair, thanks to the strong alkaline Toni permanent she had applied to the tight rows of small yellow and tiny red rods with which she had covered the crown of my head, Cindy had wrought some changes of her own to my face.

Besides the obligatory lip gloss and powder any makeup makeover might include, Cindy had unbeknownst to me taken the liberty of reshaping my once thick eyebrows into two very dramatic thin arches, which bobbed up and down in a surprised looking expression every time I blinked my eyes.

Along with all of these other demeaning alterations, performed without my consent whilst I dozed from my earlier libations, Lisa had clippered off my distinctive pride and joy sideburns. Where once refined lean facial hair trailed to a sharp point down each side of my face, ending at my jawbone, now prissy looking little spit curls fluttered in front of each crimson tipped ear.

Whilst my feminizing siesta continued, my wife and sister in law had quietly removed the tee shirt and jeans I had started the evening dressed in, by cutting them off my body in small little sections.

Coming to, as the one sister struggled to run a white frilly blouse over my outstretched left arm, while the other wrestled to draw a silky blue short pleated skirt up my legs, I just sat there in a dazed state.

Gazing down I noticed that they had already placed a silky white teddy-type slip over my head. Its straight-line bodice draped down my body to where its short flared skirt formed a puddle about my panty-clad waist, just waiting for me to stand up so that it might swish down and about my loins.

In addition, as my bleary eyes focused, I noticed there were a pair of blue and white schoolgirl saddleshoes of all things, along with juvenile looking tulip shaped ankle socks, adorning my feet.

Most disconcerting of all however was the fact that the space between the frilly cuffs of the socks and the swaying hem of the pleated skirt, which tickled my suddenly shaking knees, was filled by smooth hairless legs. A depilatory enhanced condition replicated on the section of my arm now coming forth from the puffy short sleeve of the sheer blouse I was being helped into.

Hearing my low moan as I tried to clear my head, they hustled me to my feet and quickly finished playing maids-in-waiting, as they buttoned me up the back and zipped me at the waist. While Lisa took measures to smooth my pleats in place, her sister reaching from behind, tied a navy blue silk sash into a floppy bow tie, which she positioned under the Peter Pan collar of the blouse.

All the while the two kept themselves positioned in such a way as to block the view between myself and the full length mirrors on either wall. As a result I still had no idea of the extent of their makeover, but the soft feel of the skirt and slip swishing high on my thighs told me the skirt was not kiltish in nature. Lisa then reached over and turned off the light switch, at the same time Cindy showed me to the door with a gentle nudge to my fanny accompanied by a whispered 'Off we go sweetie!' in my ear.

As Cindy locked the door behind us a shiver ran up my spine, albeit one of fear more so then from a chill, as I realized from the warm temperature reading on the bank clock across the street. As if in answer to my need however, Lisa draped a cropped white sweater in a soft plush angora over my shoulders, stopping but for a second to fasten one of its pearl buttons at my neck.

When I inquired as to the whereabouts of my leather bomber jacket Cindy responded with a slight giggle and a wave of dismissal as she said, "Oh don't worry, you won't be needing that old thing anymore."

Once again ignoring a telltale phrase, which should have concerned me ('anymore'), I moved over to the car. As I did so I found myself moving in tight steps, as I went slowly along in an attempt to keep the short skirt from flaring out and possibly exposing my privates. The girls shared a knowing smile between themselves, as they watched me attune myself to my new clothes, for unbeknownst to me I had quickly shed my usual manly saunter for a more effeminate swishing mince.

As the night air wafted the fragrance of the sweet perfume they had liberally sprayed me with past my nose I noticed an additional smell which seemed quite acrid in nature. Unbeknownst to me at the time, that was the lingering scent of the perm, which they had used to turn my boyish hair oh so prissy, and my manly looks effeminately dainty.

As I approached the car a chivalrous Cindy opened the door for me, albeit the rear one, which I in my historical position of manly control had never used before. With a pronounced sweep of my skirt she settled me in and closed the door. As she did so I heard the distinct sound of the child safety lock click into place.

As the car took off I realized that the back seat sat so low, that I couldn't see over the two girls in front to tell where we were going, but in my typical controlling fashion I just assumed that we must be headed home. Boy was I mistaken!

As I sat there still encumbered by a slight alcoholic fog, I remained obtuse to all that the girls had done, although I started to appreciate what I could see. Or more specifically what I could feel. Especially the way the soft loose skirts, floating over the even softer billowing panties, made Mr. Happy jump for joy.

I quickly lost all track of time and direction, as I kept tracing my finger over the turgid knob of my pansy wand through the dreamy nylon sheath caressing it, in anticipation of the sexual thrills Lisa and I would soon be sharing in the warm confines of our bedroom. A mindset that was moments later dashed to pieces.

For when the car finally came to a halt, and Lisa jumped out to once more open my door, I looked out not on the confines of our sleepy little neighborhood, but upon the same brightly lit parking lot we had left just a couple of hours earlier. I shivered with trepidation as I realized we were back at the bar. As I just sat there with a stunned look on my face, shaking my head no, Lisa grabbed at my hand, while doing a fairly good imitation of myself.

"It's all about your reticence not mine." "There's no reason I man can't wear a dress if he wants to." Adding, "I'm not afraid to be seen in anything that I chose to wear," with a fair impression of my own voice.

She then sneered in my face, while asking me if my hesitance was due to my suddenly not being a man anymore, as it certainly couldn't be the choice of outfits, seeing as it was one that I had bought for myself. As the words came out of her mouth and my eyes focused I realized that this was indeed one of my own recent procurements. A swishy little ensemble that I thought I had secretly stashed away for one of my bedroom fantasies. A boudoir dream which was about to become a nightmare of a public spectacle.

When I continued to balk at leaving the car, and tried to dig my heels in so to speak, I found Cindy, who had come in from the other side, pushing me from behind.

Try as I could to remain in place the sheen of the skirt afforded little friction, and between there combined motivation, I quickly found myself tumbling out on to the ground. By the time I regained my footing the door was locked and the two girls were heading for the entrance of the lounge with a departing wave in my direction.

A quick survey of the situation said I could either walk home through several very rough neighborhoods or I could catch up with them so that I didn't have to go in alone. If I couldn't get them to change their minds I hoped at the very least to slip in with them unnoticed, although with them in jeans the only skirt I might hide behind would be my own.

Drunkenly confused as to my true appearance I tried looking on the upside, foolishly figuring if I showed enough moxie I could pull this off and convince everyone that this was a nouveau-style.

As we turned the corner to go into the main lounge however my progress was arrested tout de suite, as for the first time I got a good look at myself, courtesy of the full-length mirror on the other side of the dance floor. The unintended high-pitched gasp and foolish shocked expression which spread across my face, only succeeded in drawing people's attention all the quicker to the new me. I had always been considered athletic and swarthy, with rugged good looks, but while the diminutive looking pixie staring back might be called 'cute', it would have to be added, 'in a pale and frail sort of way'. Although the state of my pallor might well be attributed to the fear which now gripped my soul as all thoughts of chutzpa and bravado went mincing out the door.

Also unintended, my startled thoughts bubbled forth from my painted lips in a mousy squeal before my limp bent wrist could be brought up to cover my mouth. To my horror and chagrin the words, "Oh My God what have they done to me?" clearly carried across the crowded room.

Two hours earlier I had left this bar the cock of the walk, everyone's friend, and an admired member of the bar's softball team. A charming rogue, whose peccadilloes and peculiarities had always been considered noteworthy. However it was plainly obvious, with just one look at the new sissified me which I had been turned me into, that all those accolades would soon become a fleeting thing of the past.

Fast forward two hours and I now presented a persona that would surely be any nerd's worst self-nightmare.

For not only must I now be seen as a wimp and a nancy, but judging from the way my uncontrollably excited penis continued to show a mind of its own as it tented out my panties, a flaming tinkerbell as well. As I stood there dumbfounded with my mouth hanging open the sudden stoppage of music allowed me to tune into the background murmuring my appearance was generating.

The nasty comments and snickering slurs, which wafted in my ears, brought tears to my eyes and crimsoned my cheeks. For although the girls had done a good job at creating a new me, it was still obvious to all who knew me, who it was who stood there. In addition my rendition of the feminine gender wasn't like anything usually seen in these parts, as all the local girl's eschewed silk and lace in this honky-tonk atmosphere.

I had thought their righteous concern about any possible embarrassment had been their motive for helping me in the first place. However in light of the way I now looked, I realized their only true consideration was to make spitefully sure that I was totally shamed.

While they quickly moved out into the room and blended in, I was left hung out to dry, looking anything but passable. Even an ugly girl or a campy drag queen would have been an improvement over this picture of a dainty sissified pansy-boy which I presented. An image that it would seemingly appear to those gathered about that I must longingly desire to affect, for why else would I willingly show up so attired. An observation that was not lost on the leather and denim regulars in the bar.

As I struggled to get through the milling crowd, most of who's groping fingers or patting hands told me they weren't interested in leaving me be, I became dismayed at the 'liberty' my actions had brought upon me. By the time I reached the relative security of the table the girls had chosen I was doing something I hadn't done in years. I was crying. Crying like a child. My doe like eyes quickly turning into twin bubbling pools.

A situation made all the worse due to the fact that they had picked a table with only two chairs, so that I was forced to beg another from a nearby table. Even that generated peels of laughter as I was asked if it wasn't too heavy and did the little miss need a helping hand.

When I finally did get seated I determined that I wouldn't move from the spot for the rest of the night no matter what. Unfortunately the girls had a different scenario in mind, as between Lisa's love of dancing and Cindy's excitement for billiards, I soon found myself, due to my known enjoyment for both of these activities, on a constant migration about the club. By the end of the evening I couldn't decide which I now hated worse.

The pool table on the one hand, put me in constant proximity to the kind of macho denizens, of which I once was one. Guys who tried to balance a cue stick and a bottle of beer in one hand, while goosing the nearest little filly with the other. The fact that I had a cock between my legs garnered me no deference however, for as I heard one rowdy put it as he piped up in a loud chortle, 'any sissy that sassy must be planning to cut it off anyway'.

The chagrin that ripped at me upon hearing those words was biting. Where I had earlier thought in terms of expressing my manhood via being on the cutting edge, a bon vivant of fashion if you will, I now found myself faced with the fact that in the minds of many clothes make the man. Or as in my case, they make for one helpless little ninny who couldn't decide if he was a mincing prince or a princess of swish.

Either way it was determined in their mind's eye that I was open season. For they saw me as neither a fair lady nor a gallant gentleman, but rather a foolish fop who didn't know which end was up. One, who based on my saucy pouty lips and sassy sissy swish, had a port of call at both ends no matter which way the wind blew.

Conversely on the other hand the dance floor proved no rescue shelter either, as within its tight confines gender lost its definition and I became a mobile maypole for everyone to do their favorite dance around.

Whilst one would fling my skirt up from behind and twist and shout in a randy manner against my panties, another would take me by my curl kissed ears and shimmy around my down turned face.

The resulting jig gave new meaning to the term triple meter, and that was just with the mademoiselles. For the esprit de corps of the male swingers took it even one step further, as their actions gave new meaning to the expression dirty dancing.

In-between fencing off rowdy pool jocks chalking their cue sticks in the crack of my pantied butt whenever I bent over the table to take my turn, and having to fend off the shorter, yet more insistent thrusts of male woodies on the dance floor, I was relegated to being the girl's golfer. While at first becoming their personal cocktail waitress, I soon found myself running …err… mincing for several of the tables around us.

This in turn garnered me more than a couple of gooses to my pantied ass in lieu of a tip, along with many a withering glare of displeasure from the regular server for our area.

Most humiliating of all was being told to make sure I made a show of ordering Shirley Temples for myself, although the non-alcoholic drinks helped me keep my wits about me. In addition I was able to maintain some standard of morals and not do anything overtly sluttish. Well almost.

The moment finally arrived that I had been dreading since my first sip of the sugary drinks. The need to use the restroom. The two girls insisted on accompanying me, which to my relief I figured meant using the lady's room, and avoiding the inherent shame of using the other.

An assumption which became doubly embarrassing when the two trousered vixens not only pushed me through the door marked M, but then followed along behind me. An act that engendered wondrous looks from the three guys gathered before the sinks, but which just as quickly became wolfish gleams.

My attempt to enter one of the stalls was arrested however as the two girls, courtesy of a pair of elbow guiding grasps, prompted me over to a vacant urinal.

"Come now Ms. Gregory and Auntie Cindy and I will help you with you potty," Lisa called out in a stage whisper for all to hear, as they made a show of prodded me along.

Once there, between Lisa's helping hands lifting my wispy skirts up over my hips, and Cindy's equally willing fingers pulling out on the waistband of my panties, before slowly drawing them down my creamy quivering legs, I found myself exposed to do my duty. Exhibited however might be a more proper term, as I stood there trembling with my baby smooth genitalia jiggling about.

Meanwhile my penis still pointed outward in a semi erect state from the recent gloved silken administrations of the shorn satiny panties. Whilst tears of humiliation made it near impossible to see, nevertheless glancing in the large wall mirror before me I took ahold of myself.

The blurred image of a helpless, curly topped, hairless, skirted pansy being toilet trained by a couple of sexy vixens before a group of his peers would have been a hysterical one indeed except for the fact that the scared looking sissy gazing back was me!

To the joint cacophony of the gathered young men's lewd boisterous comments, and the sarcastic cooing words of encouragement from a snickering Lisa, I was left to struggle with my attempts to control the flow of my golden stream, as it spurted forth disjointedly from my now rigid cock. For instead of shrinking in shame at my distraught situation, my manhood inexplicably rose to the occasion in the limp grasp of my shaking fingers.

Upon completion, instead of a lowering of my skirts I found Lisa whispering new directions in my ear. Horrific words, which gripped my heart and seized my loins in an icy clutch, as she commanded me to finish the job in hand of relieving myself.

I tried to form words of denial even as my head began to turn side to side, but to my macho remorse my right hand as if with a mind of its own began sliding back and forth, gratis of the encouraging fanny pats of Cindy's free hand. As I did so an excited Mr. Happy leapt to the occasion.

" Oh look," Cindy chirped forth, with a girlish giggle of her own, "Our little sissy boy here has a little dolly to play with!"

"Yeah but the way he's fondling it so tightly the pansy is going to make the poor thing throw up," one of the trio of real men observed with a randy candor.

"Just make sure you get it in that bowl," a second observed, "we don't want that sissy spew all over the floor."

To wit the third chimed in, "Oh that would be okay because we'll just force him down to lick it up and while he's down there feasting on pansy pudding he could top it off with some warm whipped cream fresh from the can." This last delivered with a lewd self grope of his crotch.

"I'm sure our little pantywaist here would just love a taste of real manhood, as he's never had any of his own," Lisa viciously spit forth with a derisive chortle.

Whilst I helplessly stroked myself to this mixed bag of Lisa's biting commentary and the other men's scoffing derision, my own lips uttered a series of girlish moans of delight. Soft utterances, which quickly turned to guttural groans, as my wagging tongue slurped forth from my mouth, further glistening my already glossy lips.

As I continued to whimper and mewl, all around me raucous encouragement continued to rain down upon me from every side.

"That's it my macho missy," Lisa jibed. "Show these other men what kind of sissy stud you really are."

Seeing the contrasting looks of lust and loathing in my darting eyes, one of the other weeknight regulars put forth a cutting rejoinder.

"Is this what you meant Greg when you bragged about getting into all those girl's panties and getting your rocks off."

While the others once more joined in this bawdy roast of my manhood, and Lisa verbally reaffirmed all my supposed effeminate desires, Cindy added to my woes. Maintaining her fanny fraternization with one hand, she brought the mouth of an open beer bottle up against the crack of my ass with the second, all the while blowing her own castrating words in my other ear.

" Here is your sugar daddy sweetheart. The kind of cold hard prick you once said every man should be. His name is Bud and this ones for you!"

At the same time she breathed this message of scorn, the young lioness delivered a payload of beer up my ass. Although the ice cold fluid chilled my loins, the mouth of the bottle kissing my prostate, timed with the downward stroke of my own twitching hand, elicited a mighty eruption from the head of my cock, even as I pitched to my knees.

The downward motion pulled my skirts from Lisa's clutches, freeing her to clap for joy at my spectacle of shame. Although the skirts floated down about my hips, my Benedict Arnold of a penis remained in view, as it continued to cream polish my come fuck me pumps'.

Listening to the litany of cutting comments my performance engendered, I didn't need to look up to see the scathing looks of scorn which I knew would greet me from this day forth. Hearing some of their plans for the next time Mr. Greg showed his face at the bar, Missy Greg realized he might be hiding behind his own skirts for a long time to come.

Keeping my tear glazed eyes glued to the floor, I quickly scooted my lowered panties back up around my hips and rushed out of the bathroom without so much as a backwards glance. Eyes that didn't gaze up either as I headed back to our table until a familiar voice arrested my attention. For there to greet me upon my return from my toilet exhibition was Bob, the owner. An old friend and fellow jock, who came up to inquire as to my change from earlier, confused by the abrupt difference.

He jokingly asked if Halloween was coming early this year, to which a following Lisa sarcastically responded for me, with an accompanying finger flick of my short skirts, which flamboyantly displayed my tented panties.

"No, but July Fourth has come late this year, or at least for Greg it has, as he has declared his independence from manhood with the raising of his panty flag. The big difference is that this George Washington is wearing Betsy Ross' petticoats not waving them."

With a look of astonishment, this man who had been like a brother to me, via a withering gaze and a disgusted snort, which said, you pathetic pansy, turned from me and departed mumbling to himself, "How could you do this to me."

It wasn't the only relationship I lost that night, but conversely by the time the night was over I had discovered a whole bunch of guys whose manly limb swung both ways and who wanted their newest little friend to swing on it. Knowing this, when I once more had to take a wicked leak, I eschewed a visit to the restroom and helplessly piddled my panties instead.

By the time last call was announced, my nerves were shot and frayed, as I found myself jumping at shadows. Not surprising to see, several 'gentlemen' and a couple of butch looking women asked if I couldn't come home with them. Fortunately, albeit cryptically, Lisa made my excuses for me, saying, "Maybe another time, but for tonight our sissified little darling must come with us as he has a very busy day of work tomorrow."

Although confused, because my business was closed on Saturdays, I was nonetheless grateful for the unexpected reprieve. Unexpected, in that all night long it had seemed Lisa was more then willing to sell, barter or even give my services away to whoever wanted to use me.

Fifteen minutes later when we pulled into Cindy's, remembering her conniving words in my betrayal, I wanted to curse her soul. But seeing Lisa's malicious glare, I instead closed my eyes in shame and wished her a sullen goodnight, unable to have her depart quickly enough.

However when I didn't hear Lisa restart the car to head home, I opened my eyes just in time to see her turn off the headlights and open her door, as she pronounced we would be spending the night there.

Too tired and distraught to question or worry, I slunk into the house behind the two of them. I didn't even attempt to offer an argument about the frilly baby-doll nightie I was given to wear nor the old couch chosen for my sleeping arrangements.

Left standing there emotionally crushed in a flimsy chiffon little nothing, all I could do was watch as the two sister's wandered off hand in hand to repose in the comfy of Cindy's huge king size bed. I wanted to yell out and scream my anger but instead I licked my wounds and I contented myself with the thought that come morning the worm would surely turn. However half way through the night, when I awoke myself with ecstatic moans of pleasure from stroking myself to fruition in my soft panties, I found myself second-guessing my supposed manly resolve.

Nevertheless that next morning, with my mind now clear and my nerves steeled, I determined nothing would stand in my way of once again setting my own destiny. Unbeknownst to me however the Fates had already crossed my path and there was little I was going to do about it.

The Fates, three vixen goddesses who control the destinies of men and sissies alike. Clotho, read that Lisa, to spin the thread of life, Lachesis, a.k.a. Cindy, to decide its length and Atropos to sever it. Just when I thought I might right the ship of my life and set sail on a new destiny, there at the breakfast table sat my Atropos, my 'loving' sister Patty.

Miss Patty who in our youth had more than once made life miserable for me, when she had discovered my misuse of her skirts, sat there with a big shit-eating grin on her face. Well I remember her disparaging words that fate-filled morning as she set out to cut any remaining ties to my manly existence.

"Well hello little sister. I see you've finally had a reality check and recognized what kind of man you really are. The pantywaist kind who'd steal his sister's school uniform and traipse all over town in it. Well now you're finally going to get several all your own…uniforms that is… for your new part time job at Cindy's Hair Palace."

Seeing the bewildered look on my face, she went on to tell me it was the least that I could do to pay back her two friends for all the free services they had provided me last night. "Not to mention this pretty little frock they've got for you to wear today," she added, dangling it before my eyes.

To my chagrin I found myself on the verge of being mesmerized as my fingers began to twitch and my eyes started to dance at just how pretty it was. So very pretty.

Catching my breath I lowered my eyes and hesitantly mentioned that I had my own clothing to wear. To wit she just tisk-tisked and inquired if I meant the skirt and blouse she had graciously taken to the cleaners for me earlier that morning or the tattered jeans still out in the trunk of the car.

"So you see you can either walk home nude or you can join the girls at the shop as their newest rinse girl."

Feeling my life going down the tubes I was lost for words, so I did the only thing I could. Reaching out I took hold of the proffered dress, along with a bag of accessories, and wrote the check for it with my new life. A life that appeared headed for what I had secretly always desired, but in the past wasn't man enough to grasp. A life in little girl dresses and tight curly tresses.

When I returned from changing, my attire said it all. While Lisa and Cindy looked perky and stylish in their tailored Claiborne slacks and sleeveless tops, accented by kicky go-go boots, I stood there once again looking for all the world like a lost little school girl.

I found myself attired in a short and swirly lightweight silken frock, with puffy short sleeves, and a sash that tied in a big bow in back. Its slightly loose bodice dropped to a high waistline, which started just below the ribs and then flared out to mid thigh on the wings of the petticoat slip that I wore underneath it.

Like the dress the slip was full length, albeit one with frilly lace trimmed straps which came down to an equally high pinched waist, before flaring out on a sea of dreamy chiffon. Not quite a ball gown petticoat, its smaller yardage while allowing some fluff, also allowed the dresses' flowing skirt to have a full range of motion. One with which it swished the billowy pink panties provided me seductively around my swelling cock.

Bobbing up and down the two skirts contended with each other to see which one would ride up higher on my thighs. Once again the socks were lacy, with tulip shaped cuffs spiraling around my ankles, whilst the shoes were red patent leather Mary Janes to offset the embroidered hearts which played all over the dresses' pale pink background.

Knowing their assured intentions, I had taken the liberty of rouging my cheeks and tinting my lips a soft pink, utilizing the cosmetic supplies in the upstairs bathroom. All in preparation for my return to the salon of doom.

All in all the entire outfit must have cost a pretty penny. One which would take me more than a little while to reimburse. Especially when one factored in the cost of their makeover. My Saturdays would not be free for quite some time to come, as I would be working my girlish ass off…literally…in an attempt to pay back my femme debt.

It was during that very first Saturday whilst I was performing the task of washing one woman's feet in preparation for her pedicure that I learned not all my chores would be so mundane. Licentious and libertine might be better suited as a job description, for I next found a privacy screen drawn across so that I might provide oral restitution as well to this member of their elite clientele.

While Lisa first worked on Miss Snoot's fingertips I found myself down on my knees dividing my time between their two vaginal divides. Demeaned at first, at being so used by these Sapphic socialites, I quickly changed my opinion however when I noticed the size of the tip my service garnered.

While touching up my lipstick I reflected on the positive side of being the salon slut. An opinion that evaporated however when I discovered that some of their rich clients, who got their hair cut there, were also male. A few of which that got their nails manicured also. Such that later that same day I found cock sucking added to my resume. A job function for which I had no training, but one that I took to quite quickly as I added man-juice to my new diet.

My job had suddenly become quite exotic, however for the most part my typical functions there, while servile, were also quite simplistic. I picked up the little nuances that went along with being a receptionist/shampoo girl fairly easily, along with each customer's idiosyncrasies, although it was weeks before I finished meeting the entire client base.

This meant a whole new sea of faces each week to sail my sissified self before, although to my increasing humiliation I learned that many of the well-to-do were weekly customers.

When all was said and done, Patty had a new sister whom she was proud of, Cindy had the most popular shampoo girl in town and I had a whole new group of friends. Ones with which I could discuss either style or sports, as afternoons on the seventh day of the week quickly became men's day, or as they liked to call it Sissy Saturday. Many was the day where my tips exceeded those of the stylists, however that in part was due to the array of unique services which I found myself providing.

Unfortunately while my pay would often surpass that which my own regular job brought in, much of it was squandered on additional hair and nail services for myself along with the new outfit it seemed I needed each week. Within two months my wardrobe of party frocks spanned the colors of the rainbow, more than enough to cover every day of the week if need be. It wasn't long before I noticed that the feminine side of my bedroom closet was slowly trespassing onto its counterpart's space.

Everyone seemed to like the new Greg including a few of the women from my plant that had learned of my moonlighting. Fortunately they were willing to trade off their insider knowledge and the mentioning thereof, for some considerations on the job. Perks which were intended to maintain my little secret. Special benefits, which were soon to become antiquated however, thanks to the continuing 'gratitude' of my precious Lisa.

While Patty was pleased with her new sibling and Cindy considered me her best employee, my darling Lisa was still peeved over my ongoing faux pas as her man. So much so that she determined that if she couldn't have my undivided services, as the man which suited her needs, than no one would have him at all.

With that in mind she planned to turn my one-day a week misadventure into a full time situation. Resolved that if her latest ploy failed to reeducate me, by shamefully parading me around in front of everyone I know in full sissy regalia, she would institute a lifetime career change instead, thus effectively castrating me from society.

To facilitate this further subjugation of me to her will she secretly started keeping a photo journal of all my voyages in skirts. One that unbeknownst to me she was planning to go public with.

To that end she had even set up a web page dedicated to my fall from masculine grace. Intended as a means to keep me in line even after I submitted to her will, it was a vivid reminder of how even the most macho of men were just a frilly frock and prissy perm away from being the feminized plaything of a resourceful mistress.

When I later saw it for myself I was truly surprised at the variety of different ensembles she had clandestinely photo'd me in over the past couple of years. A montage which bespoke as much about the voyeur in her as it did about the nancy in me.

What she had failed to realize however was that while she conceived and brought forth her further strategies, my old and new lives were happily melding together, as

I was slowly becoming the woman of my dreams.

Meanwhile this bizarre melodrama that had become my life rolled on, as nothing much else really changed until my annual trip to corporate in Philadelphia a month later. A rather stodgy affair, which left me honestly thinking that a few more Saturdays each week might not be such a bad thing. Still in all I wasn't prepared for the radical changes Lisa had prepared for my homecoming.

For upon my return I found out that while I was gone Lisa had gotten rid of all my male clothing, and that while I wasn't left pantless, it was only because almost all of my suits were now women's designer pieces. I say almost all, in that she had picked out a few with skirts also, to give me that career woman look.

With their pinched waist jackets and billowy slacks they left no doubt as to their intended gender. Made from a combination of polyester and rayon, with just a hint of spandex for shape, their soft styling gave me a distinctly feminine silhouette. Especially around the office when put in juxtaposition to the background of the other men's boxy suits.

Tight to the shoulders, the form-fitting jacket with its distinctly feminine single button closure, nipped in at the waist giving me a defined hourglass shape. While at the same time the loose fitting pants, draping down from the waist with their billowy pleated front and smooth butt clinging backside, courtesy of no visible pockets anywhere, dropped into wide flowing legs giving me a chic graceful look. A look rendered ever so much more dainty when one of the crisp pleated skirts took their place.

These were coupled with the trendy patent leather loafers and sheer nylon sock hose, with which Lisa had replaced my old footwear, along with silk ascots and flouncy bow ties, which now finished off my soft pastel blouses, most of which buttoned up the back. It was no wonder that I looked more suited for the secretarial pool then the boardroom.

In addition I was to discover my new wardrobe gave a whole new meaning to relaxed Fridays, as the array of choices were astounding, as long as one wanted to look totally effeminate. The range went from a sweater and kilt set, done in a pink and lavender plaid, that looked more lassie then laddie, to knickers and a blouse which appeared like it had stepped right out from the Great Gatsby's wardrobe. Mrs. Gatsby's that is.

In-between there were short-suit sets, some with culottes which had a distinct skirt look to them, ranging on down to a little sailor outfit with button on suspenders and a blue and white sheer silk jersey with a matching scarf tied around the neck. Many of the tops were so form fitting, as to give my lithe figure a very androgynous look.

In staying with a motif geared toward presenting my as a prissy plastic pansy, rather than a genuine gilded lily, none of my she-boy attires were hindered by even a hint of the mascara and blush that the girls insisted I wear at the salon for the purpose of looking femininely seductive.

Instead, with the exception of an occasional overtly sissified bow, bobby pinned in my curly locks to accent my humiliation, I was left to look foolish as there could be no doubt that I obviously was a very effeminate male.

A role I played well, as I would helplessly fawn and simper like a sycophant dandy whenever so attired, to the point of even dropping a confused curtsey on occasion to a staff member whose commanding performance left me thinking of them as the boss and me their ditzy underling.

After awhile my appearance became so uncomfortable for several of the guys that two of them left for other jobs, while one transferred to another office. This just left me prissy Jimmy, the up and coming wonder-kid, as the only other full time male in the office. A true boy-toy who had learned well the art of kissing up to the boss. So much so that he soon was shopping for himself at the same big girl boutiques as my Lisa did for me.

In addition there was Joe Blase, the part time accountant and office nerd, who specialized in being Mr. Cellophane Man to such an extent, that I expected someday to find out that he had moved his desk into a mouse hole. He whose Walter Mitty persona gave new meaning to the word ninny.

 

Thanks to these changes the office took on a very feminine mystique all its own, as employee Macho Greg had been relegated to the dead letter file. For although I was still the boss, I more importantly was one of the girls.

Even with all that however Lisa was not content and wouldn't be until she broke me in the eyes of the whole town. What she failed to see was that with each change I was not only becoming a better boss, who was well thought of, but also a better person who was loved throughout the community despite all my foibles.

Thus when she put her final solution in play, while it proved a little unsettling at first, it failed to engender the wrath she had hoped for. She had hoped for a humiliated upset male. What she got instead was a contented sissy who knew his proper place in the world of women.

Her plan had been diabolical in its simplicity and yet it failed. So poorly that she wanted a divorce and hoped to push me into it via blackmail, for although we were separated, she was still controlling major parts of my life via long distance.

To wit after showing me some of her more juicy photos with a bedroom theme, in which I was both femininely scanty and effeminately occupied, she threatened to go public with them if I didn't report to her shop each day for my daily dressing and photo op. Outfits which ranged the gamut from girlishly giddy in their adolescent motif to outright outrageous representations of cheerleaders, ballerinas and French maids.

In addition she impounded my car, which had been purchased under her name, and forced me to use public transportation in its stead. A daily event she had intended to break my spirit completely, but which instead I found exciting and exhilarating, as I revisited those Sunday morning jaunts of my youth.

First it was billowy pleated skirts and frilly blouses dripping in lace, in everything from satiny pokka-dots to flowery patterns emblazoned on the softest silk. This quickly escalated upward in the flounce of the material, and downward in the age of the styling, so that by the end of my second week, relaxed Fridays had taken on the air of a little girl's birthday party.

Each day the outfits became a little more brazenly sluttish and each day the staff became closer. Kind words became helping hands and willing service. Instead of dividing us, Lisa was uniting us in the bonds of skirts and dresses.

So much so that a week later, when the staff threw me a surprise birthday party, several of the ladies had dressed in a very youthful fashion to make me feel apropos. Meanwhile Jimmy showed up in a perky party frock which matched my own in style, albeit a pale sherbet in hue to my classic Little Miss Pink.

Just about the time the party was in full swing Lisa's entrance coincided with the timing of several of the ladies giving me my skirts-up, panty-whacking birthday spanks, while at the same time Jimmy was giving me a tongue fencing birthday kiss.

Needless to say Lisa was distraught, beside herself over the lack of animosity she had expected to witness, but even more so upon seeing the loving kindness which seemed to be in bloom.

Realizing that all her plans were going for naught, the following Monday she filled for a divorce. And while she still hoped to get everything from me by holding me over a barrel, my lawyer assured me at the time that in the eyes of the court that wasn't going to happen. They wouldn't take kindly to her subterfuge, he said, besides which the loving wife, (that would be me), usually gets everything.

Fortunately she has since taken the high road in this matter, and whilst we are no longer husband and wife, she has dropped her attempts to remake me into the man of her dreams. Instead we have developed a more tolerable mistress/sissy servant relationship between us. A triumverant if you will, as along with my sister Patty, the new 'Mr.' Roberts in Lisa's life, the two of them still maintain a controlling interest in my daily affairs. This right up to the point of still selecting my attire most days even though we live separately.

And so I end this little tale. One in which I went from a fey and callow fellow to a frail and dainty missy. I had simply wanted to express myself in a small way, but instead found myself living a big dream.

PS: Believe what you will, but each day I find little blessings that make my world a softer, prettier place to live. Thank you for your lovely letters. Your friend, Greg, a.k.a. Sissy Gray.

  

  

  

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