u/Reasonable_Injury121

Another one from the archives. This is yet another seemingly lost story that I saved from cw’s old Yahoo Groups site (although I’ve seen parts of this one on the web in the past, so it may not be truly lost). It was written by David, the co-author of A Rare Gem, which I posted a few months back. David may not have been prolific, but he was damn good. In addition to the story, I have copied below a note accompanying one of the chapters from David to Whitedog. It is not strictly a “cuckold” story, in that the older, submissive protagonist is not married to (or has any pretense to any kind of romantic relationship with) the young dominant female, Miss Fiona. Yet, it is most definitely a femdom story and more, with the same ethos (voyeurism, a beta male dominated and degraded by an alpha couple, group humiliation, etc. ) as many of the stories on this wonderful subreddit. I plan to use AI to further illustrate this story on the r/cuckold_humiliationAI site as well. I hope you enjoy the story as much as I do (the first chapter is brief, mostly a set up for what follows).

Hello all!
In answer to Whitedog, yes I did write Ashtray Slave and I also cowrote A Rare Gem in the files section under Davids Stories.
Unfortunately, I am not what you would call prolific. I think I have written only two or three stories in twelve years! This is down to partly personal circumstances and also laziness. But I have become aware that there seems to be less and less GOOD stories around. By GOOD I mean the sort of themes Whitedog and C.W. write about. The boyfriend in these stories is just as active in tormenting the sub as the wife. For some reason this really appeals to me. Anyway I could go on, but I've added the second part of my little vignette of a subs life (just realised I haven't given the pig a name yet!)
Enjoy.
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Slave to Tyrants, Part 1

By David

So here I am, a 56 year old senior executive, overwieght and balding, about to start my weekly ritual. I have laid out the red carpet that leads from my front door to the sitting room, I have my "ugly tax" of $500 dollars in its usual manilla envelope and I prostrate myself on the hardwood floor by the side of the carpet, nose to the wood.

All that remains is for me to keep my nose pressed firmly to the floor and await the arrival of the young 19 year old couple who have such a tyranical hold over me and my lifestyle - Miss Fiona and Master Jason. Over a year ago I had approached this young couple with a view to paying them for humiliation, domination and intense degradation. Naturally there were slightly tentative at first, but they soon came to realise that I was a complete, utter and enthusiastic old pay pig who would gladly shell out big bucks simply to be treated like something they had stepped in!

Their abuse of me evolved from allowing me to lick their shoes clean before they went for a night out on the town at my expense, to corporal punishment and exhorbatant fines for slight or imagined misdeamors. Blisteringly hard canings for faling to address Jason as "Sir" at the start and end of every sentance, or being slow to offer Fiona and Jason a light for their cigarettes became so common that after a year of service my elderly fat backside has permanent white scars! It became common for me to have to carry around a wad of $20 dollar bills with me, and each and every time one of them entered the room I was in I would be required to peel off a bill and present it to them from my knees.

So I wait for f their arrival, my heart thumping in anticapation of the pain and abuse that will surely accompany their arrival. Sometimes they might arrive at house dressed up for an evening out and casually torture me for half an hour before leaving, $1000
dollars richer. Or perhaps I would be required to serve as a menial lackay as they dined from my larder and use my best china. Or perhaps they might use the bedroom I keep especially prepared for them for a night of passion on silk sheets while I spend the night in a cupboard under the sink. They may even bring round their friends to laugh at my degradation.

After a couple of hours waitng, knees becoming more and more tender as my kow tow position became more and more uncomfortable, I eventually heard the key in the door and my heart began to thump in anticipation as I became aware of the patent leather stiletos and loafers of my superiors on each side of my head.

A snap of fingers and I kneel bolt upright at attention, back straight and eyes looking forward, although I am careful to never directly look at my superiors in the face. I am aware though of the tight knee length pencil skirt of Miss Fiona, and her expensive black satin blouse as she extends her small dainty hand for my "ugly tax". A tax to be paid immediately upon their arrival for simply...well being ugly actually!

"And I must say, you really do look horrendously ugly today!" giggles Miss Fiona as she uses her finger and thumb to flick the end of my nose hard enough to make my eyes water.

"Yes Miss, sorry Miss, and sorry Sir for being ugly, and thank you for reminding me and allowing me to pay my fine,” I grovelled to them in return.

The flick from her fingers casued me to observe how much pleasure those same perfect fingers and hands could give to Jason, and how much pain and suffering they seemed to reserve especially for me. I have seen Jason lean back with his hands behind his head as Fiona's delicate fingers dance up and down the length of his cock, her French manicured nails teasing Jason’s cock head while her soft warm palm gently cups and carresses his balls. And I have also seen those same fingers playfully toy with the button of the remote control for my electric shock collar, turned up to maximum, while I wait in horror for the moment she giggles and decides to actually press the button for perhaps ten long seconds of intense electric shocks to my balls!
I have an intense fear of electric shocks and watching so intentely for the slightest movement of her taunting finger towards that button actually made me piss myself in fright.

So that was another nail in my coffin. Knowing how much I hated shocks and the dreaded collar, Fiona and Jason would routinely show me off to their friends and take turns in giving me degrading orders while they held that damn remote control knowing I would become panic stricken and frantic in my efforts to please!

The casual order from the person holding the remote of "Clean the ashtray piggy", would see me hold my head right back and tip a full ashtray into my mouth in one go while I tongue bathed the glass ashtray until it gleamed, simply to avoid another shock from Fiona, Jason or any of their hysterically laughing friends.

I could hear the sarcastic comments from them as Fiona remarked, “Do you know he's fluent in five languages?"

"Well thats all his tongue is good for now!" laughed Jason!

Or the times when Miss Fiona would go lingerie shopping on a Saturday afternoon while Jason would recline on the lazee-boy chair, dressed in a men’s silk kimono, with iced drinks and a packet of cigarettes by his side while he would direct me to do enforced exercises and agonising stress positions while he held the remote! I would end up a quivering, panting and sweating heap while he would blow a stream of smoke down in my face and casually order, “Give me another 20 push-ups, scum!"

Or I may have had to tightly hold a pencil, sharpened to a cruel point at both ends, between my thighs and waddle from one end of the room to another simply for his amusement. If the pencil drops then ZAAAP! I would end up in an agonising fetal position on the floor while his mocking laughter rang in my ears.

The alpha athletes, the cheerleaders, and the towel boy cucks. Everyone has their place and everyone has a job to do. The towel boy in the middle is performing one of his duties diligently. He has a huge crush on the cheerleader who is watching him, so this is not an easy task.

Brittany, the cheerleader, is a fashion design major. She volunteered for an important school project to redesign the uniform of the towel boys. She is quite pleased with the results.

Brittany dumped one of the two guys in this picture for the other. Can you guess which one she is sleeping with now?

I watch helplessly, the pain of my recent whipping at his hands radiating through my body. I now know without a doubt that I have lost her to him forever, and that I am destined to be his slave for my remaining years.

I’ve embarrassed my mistress with my poor dancing. That’s me in the middle, and I just practically tripped while trying to pirouette. My mistress gets quite competitive with the other mistresses who have enrolled their loser cuckold husbands and boyfriends in The Sissy Cuck Ballet troupe. I’ve let her down. So, now she’s asking her lover, Master Tyler, to cane me tonight when the three of us get home. He doesn’t fuck around. I better step it up indeed before the actual performance of Swan Lake next month, or I’ll never be able to sit down again.

Three members of the exclusive BNWO Ballet Company perform a recital to show the aspiring members, all seated on the floor next to their owners, the intense physical demands of being a member of the troupe. The psychological demands are equally – if not more – intense, but harder to demonstrate.

For my wife, licking the sweat off her lover’s chest, even his armpit, is sweet. She is addicted to his to his body – addicted to his scent. For me, licking the foul smelling, sweaty foot of this arrogant, cocky young bastard is the opposite of sweet. It is repellent. It is nauseating. And oh how he loves to emasculate me in front of her! Forcing me to wear pink panties or tights. Collaring me like his slave and pulling me around on a leash like his dog. Beating me in front of her with a whip or a cane or his belt or even his bare hand.

And yet, when I see how much she needs him, I cannot deny her. More than that, I know that if I were to force her to choose between us, she would obviously choose him. And I would be out in the cold. I would lose the woman I love so desperately. Her lover has plenty of other women, so I am no threat to him whatsoever. I’m here to foot the bills and serve as his errand boy (even though I’m 15 years older than he is). I’m here to be his and my wife’s aphrodisiac.

Because I see how much it arouses her to watch him humiliate me and emasculate me. And seeing my beautiful wife aroused, in turn arouses me. So even as I practically gag as I lick his feet, I feel my cock stiffen as I catch my wife’s eye – seeing her arousal, seeing her faint contempt for me as I abase myself at her lover’s feet. All for her! Sacrificing my dignity for her, like the good submissive cuckold I am.

Blast my wife, Deirdre!

She knows that Penelope is my favorite niece. She knows how beautiful I think Penelope is. She knows full well that Penelope used to look up to me when she was a girl.

But now that Penelope has turned 18, Deirdre has decided that it’s time for my lovely niece to be educated in the ways of the world. A crash course, one might say. She has decided to fully expose my perversion – my transvestism – and our decadent lifestyle to my niece, in dramatic fashion. Yes, Penelope has learned this afternoon that I am the feminized cuckold slave to my wife and her lover. The fact that her lover is fifteen years younger than me and the junior partner in our law practice only makes the situation more humiliating. More arousing, too, naturally but what’s an old sissy cuck to do?

Still, I will never forget the look of shock, followed by the look of amused contempt on Penelope's face when Billings – my junior partner – led me out by collar and lead into the middle of the living room, where my niece sat on the couch next to Deidre. Me wearing nothing but a wig, a pair of sheer pantyhose and high heels, Billings using the cane and the leash to parade me around the room like his pansy puppet. And just when I thought it was impossible to ever feel such intense shame, Billings brings the cane down on my nylon-clad buttocks, I feel my cock stiffen and tent out my pantyhose and I fleetingly make eye contact with my niece, seeing her cover her mouth to stifle her shocked, derisive laugh. I hear Deirdre point out my state of hopeless arousal to my niece, as if that was necessary. And it is at that moment that I realize that this is an education for me as well – I am learning that there are greater depths of humiliation than I ever thought possible.

Blast Deirdre! I see how much she is enjoying herself.

My 18 year-old niece, Ashley, and my 18 year-old nephew, Andrew, quite relish their respective roles as my instructor and my disciplinarian. My wife, Mistress Susan, has given them full authority over me. Mistress has provided clear instructions regarding how I am to greet her lover when I am presented to him this evening. I have been told very little about him, but do know that he is several years younger than me and that he used to work for me. The evening ahead promises to be an extraordinarily humiliating one for me – even by my standards. However, for the moment, I must diligently practice curtsying so as to give no one any easy excuse to cane me, either now during my practice sessions or during this evening when my new status becomes known to someone outside of family members. Someone who in all likelihood has a grudge against me. It is challenging to curtsy even slightly, let alone deeply, given how tightly my corset is laced. In fact, it is challenging even to walk, even to fully breathe. However, Mistress Susan believes strongly that with the combination of the strict diet I am now on and rigorous tight lacing, my body will, in due time, conform to her requirements.

————————————————————————————————————————————————————

After my wife, Sue (or, Mistress Susan, as I am now compelled to address her in private), caught me cross-dressing six months ago – with three videos captured from several well hidden, high resolution cameras she had installed – I suddenly found myself very much in her power. This was quite the abrupt role reversal, as I had always lorded it over her during our 30 years of marriage as the man of the house and the primary breadwinner (and a very successful one at that). A prominent local businessman and a pillar of my community, I certainly did not want evidence of my little hobby to become publicly known. It would destroy my career and my standing in the community – especially as I had carefully cultivated my reputation as a “tough as nails” boss at my company and sort of an all around macho prick – not someone to be fucked with. The humiliation of being seen prancing around in dresses, high heels and pantyhose by my friends, coworkers and extended family would be beyond devastating. Having behaved as a prick towards my wife for many years, I did not doubt for a moment that she would follow through on her threats to expose me if I did not agree to do everything she wants. Yes, public exposure of my perversion would’ve been damaging to her, too, but it would’ve been far more damaging to me and she would’ve gotten a lot of sympathy (not to mention, very likely, a damn good divorce settlement).

So, publicly, I remain a successful executive and a fearsome boss. However, behind the closed doors of our mansion, my life is radically different now. When I get home from the office, I immediately remove my suit, change into any number of maid’s uniforms Mistress Susan has had custom made for me and begin my second job. In addition to weekday evenings and mornings – performing cleaning chores and serving her breakfast before I head off for my long workday – I spend the majority of my weekends waiting on my wife hand and foot, as her humble, domestic servant. I no longer sleep in the master bedroom, of course, but rather in the basement, in a spartan room that has been converted from a large storage closet into my maid’s quarters. All that is in that claustrophobic, windowless room is an uncomfortable cot, a clothes rack to hold my maid’s uniforms, and a dresser to hold my panties, stockings, and other feminine accessories. And a mirror, of course, for me to check that I am properly attired, as imperfections (wrinkled clothes, smudges on the polish of my high heels, runs in my stockings and so forth) are scrupulously recorded, and later strictly punished (there is also room for several punishment canes, straps, and paddles to hang on the wall, a constant reminder to me to be fastidious and obedient). Fortunately, I have a small bathroom in the basement that I am able to use with a modicum of privacy. For the time being at least, I am permitted to keep my few remaining suits and other masculine clothes in my old closet in the master bedroom. Occasionally, I am granted permission to go out to go golfing with my buddies, to go to a basketball game or to attend other events to maintain my social status. Even though that status is a total charade and likely disintegrating. But more on that later… In any case, it is still necessary for me to retain some male clothes. 

Only a few people know about our altered lifestyle – people Sue can trust. Namely, her younger sister, Gail, and Gail’s two children, our 18 year-old niece, Ashley, and her twin brother, Andrew. Gail‘s husband, Alan, passed away a few years ago, so I am spared that indignity, at least…

But, believe me, the indignities I do endure on an a daily basis are manifold. Gail never liked me and was particularly resentful of the fact that I never wanted to have children with Sue. Sensing her dislike, I always behaved quite condescendingly towards my sister-in-law and her family. I used to like to rub it in to Alan that I made a lot more money than he did and was always rather dismissive of, and impatient with, Ashley and Andrew when they were younger. The truth is, I’ve never been fond of children. Ashley has turned out to be a quite beautiful young woman. I remarked upon this to Sue about a year ago. I suspect that’s partly why Sue has decided to put Ashley in charge of lacing my corset, overseeing my curtsying practice and ensuring that my maid’s quarters are in the proper order. In other words, Sue knew that I have the hots for Ashley and, therefore, knew that my shame in routinely being scrutinized by Ashley in my humiliating clothing, and having to follow her commands, would be particularly acute. 

And it is, no question! What surprises me, however, is that I find it even more humiliating (if that is possible) to be seen as I now am by my nephew, who is my chief disciplinarian. Like his twin sister, Andrew is also quite good looking. As Ashley pulls the laces of my corset (unreasonably tightly, if you ask my opinion – which no one does, of course) or critically supervises my curtsying or my walking in high heels while balancing a book on my head, it is Andrew who stands nearby with a wooden cane or a riding crop in hand, always ready to sharply strike my ass should I displease Ashley with my efforts. He regards me always either with a contemptuous smirk or with stern displeasure, confident in his utter power over me.  Naturally, he’s is the the one who administers my more extended punishments, including my weekly ritual maintenance spanking or caning (depending on how I behaved that week or simply depending on Mistress Susan’s whims). These sessions are always attended by Mistress Susan, Gail and Ashley. The three women all take great delight in watching the young, athletic Andrew order around his sissy uncle and then flay the skin off my buttocks, thighs, and even occasionally my back and the soles of my feet.

As Miss Ashley – as I now am required to address her – tightens the laces of the corset I will be wearing this fateful evening, I squirm in discomfort, watching the riding crop being wielded by Master Andrew carefully. Things have now reached a crossroads, and I am extremely anxious. You see, not surprisingly, Mistress Susan has taken a lover, and I am to meet him tonight. Well, “meet” is perhaps not the most accurate word, because Mistress Susan has explained to me that her lover is somebody already known to me. Specifically, he is someone who used to work for me for me at my company. The only other things I’ve been told about him by Mistress Susan is that he’s at least 10 years younger than me and extremely good looking. Oh, yes, and that he is “a real man“ – in stark contrast, obviously, to me.

Being the difficult boss that I am – or perhaps I should say “was,” as I have toned things down quite a bit at the office lately given what I now experience daily at home – I have driven away several employees over the years, so it is hard to know exactly who she’s talking about. I suspect it might be Lucas Corval. I believe I saw Sue flirting with Corval at the company Christmas party a couple of years back. He was a ruggedly handsome young man, probably about 15 years my junior or so, with dark, brown hair and an athletic build. Perhaps it was because he was so good looking that I was especially hard on him, eventually prompting him to angrily resign about a year ago and telling me at the time that “karma is a bitch” and that “I would get mine someday.” Hopefully, I’m wrong, because if it is indeed Lucas who is my wife’s new lover, it would not be good. But let’s be real, it’s not going to be good no matter who it is. 

I should know in about an hour… 

My live-in lover, Malik, and I are excited to pick up my husband, Robbie, after his intensive two week refresher course at The Sissy Maid Institute. Headmistress Edwards and her team of highly qualified female instructors and male disciplinarians take great pride in their work. It’s a nice touch for Ms. Edwards to personally deliver Robbie back into our possession. It‘s clear from the nearly flawless way that Robbie executes his deep curtsy to Malik and me, that the refresher course has been a success. I had no doubt, and look forward to discovering what other improvements have been made in Robbie’s deportment and domestic skills.

After my wife, Sue (or, Mistress Susan, as I am now compelled to address her in private), caught me cross-dressing six months ago – with three videos captured from several well hidden, high resolution cameras she had installed – I suddenly found myself very much in her power. This was quite the abrupt role reversal, as I had always lorded it over her during our 30 years of marriage as the man of the house and the primary breadwinner (and a very successful one at that). A prominent local businessman and a pillar of my community, I certainly did not want evidence of my little hobby to become publicly known. It would destroy my career and my standing in the community – especially as I had carefully cultivated my reputation as a “tough as nails” boss at my company and sort of an all around macho prick – not someone to be fucked with. The humiliation of being seen prancing around in dresses, high heels and pantyhose by my friends, coworkers and extended family would be beyond devastating. Having behaved as a prick towards my wife for many years, I did not doubt for a moment that she would follow through on her threats to expose me if I did not agree to do everything she wants. Yes, public exposure of my perversion would’ve been damaging to her, too, but it would’ve been far more damaging to me and she would’ve gotten a lot of sympathy (not to mention, very likely, a damn good divorce settlement).

So, publicly, I remain a successful executive and a fearsome boss. However, behind the closed doors of our mansion, my life is radically different now. When I get home from the office, I immediately remove my suit, change into any number of maid’s uniforms Mistress Susan has had custom made for me and begin my second job. In addition to weekday evenings and mornings – performing cleaning chores and serving her breakfast before I head off for my long workday – I spend the majority of my weekends waiting on my wife hand and foot, as her humble, domestic servant. I no longer sleep in the master bedroom, of course, but rather in the basement, in a spartan room that has been converted from a large storage closet into my maid’s quarters. All that is in that claustrophobic, windowless room is an uncomfortable cot, a clothes rack to hold my maid’s uniforms, and a dresser to hold my panties, stockings, and other feminine accessories. And a mirror, of course, for me to check that I am properly attired, as imperfections (wrinkled clothes, smudges on the polish of my high heels, runs in my stockings and so forth) are scrupulously recorded, and later strictly punished (there is also room for several punishment canes, straps and paddles to hang on the wall, a constant reminder to me to be fastidious and obedient). Fortunately, I have a small bathroom in the basement that I am able to use with a modicum of privacy. For the time being at least, I am permitted to keep my few remaining suits and other masculine clothes in my old closet in the master bedroom. Occasionally, I am granted permission to go out to go golfing with my buddies, to go to a basketball game or to attend other events to maintain my social status. Even though that status is a total charade and likely disintegrating. But more on that later… In any case, it is still necessary for me to retain some male clothes. 

Only a few people know about our altered lifestyle – people Sue can trust. Namely, her younger sister, Gail, and Gail’s two children, our 18 year-old niece, Ashley, and her twin brother, Andrew. Gail‘s husband, Alan, passed away a few years ago, so I am spared that indignity, at least…

But, believe me, the indignities I do endure on an a daily basis are manifold. Gail never liked me and was particularly resentful of the fact that I never wanted to have children with Sue. Sensing her dislike, I always behaved quite condescendingly towards my sister-in-law and her family. I used to like to rub it in to Alan that I made a lot more money than he did and was always rather dismissive of, and impatient with, Ashley and Andrew when they were younger. The truth is, I’ve never been fond of children. Ashley has turned out to be a quite beautiful young woman. I remarked upon this to Sue about a year ago. I suspect that’s partly why Sue has decided to put Ashley in charge of lacing my corset, overseeing my curtsying practice and ensuring that my maid’s quarters are in the proper order. In other words, Sue knew that I have the hots for Ashley and, therefore, knew that my shame in routinely being scrutinized by Ashley in my humiliating clothing, and having to follow her commands, would be particularly acute. 

And it is, no question! What surprises me, however, is that I find it even more humiliating (if that is possible) to be seen as I now am by my nephew, who is my chief disciplinarian. Like his twin sister, Andrew is also quite good looking. As Ashley pulls the laces of my corset (unreasonably tightly, if you ask my opinion – which no one does, of course) or critically supervises my curtsying or my walking in high heels while balancing a book on my head, it is Andrew who stands nearby with a wooden cane or a riding crop in hand, always ready to sharply strike my ass should I displease Ashley with my efforts. He regards me always either with a contemptuous smirk or with stern displeasure, confident in his utter power over me.  Naturally, he’s is the the one who administers my more extended punishments, including my weekly ritual maintenance spanking or caning (depending on how I behaved that week or simply depending on Mistress Susan’s whims). These sessions are always attended by Mistress Susan, Gail and Ashley. The three women all take great delight in watching the young, athletic Andrew order around his sissy uncle and then flay the skin off my buttocks, thighs, and even occasionally my back and the soles of my feet.

As Miss Ashley – as I now address her – tightens the laces of the corset I will be wearing this fateful evening, I squirm in discomfort, watching the riding crop being wielded by Master Andrew carefully. Things have now reached a crossroads, and I am extremely anxious. You see, not surprisingly, Mistress Susan has taken a lover, and I am to meet him tonight. Well, “meet” is perhaps not the most accurate word, because Mistress Susan has explained to me that her lover is somebody already known to me. Specifically, he is someone who used to work for me for me at my company. The only other things I’ve been told about him by Mistress Susan is that he’s at least 10 years younger than me and extremely good looking. Oh, yes, and that he is “a real man“ – in stark contrast, obviously, to me.

Being the difficult boss that I am – or perhaps I should say “was,” as I have toned things down quite a bit at the office lately given what I now experience daily at home – I have driven away several employees over the years, so it is hard to know exactly who she’s talking about. I suspect it might be Lucas Corval. I believe I saw Sue flirting with Corval at the company Christmas party a couple of years back. He was a ruggedly handsome young man, probably about 15 years my junior or so, with dark, brown hair and an athletic build. Perhaps it was because he was so good looking that I was especially hard on him, eventually prompting him to angrily resign about a year ago and telling me at the time that “karma is a bitch” and that “I would get mine someday.” Hopefully, I’m wrong, because if it is indeed Lucas who is my wife’s new lover, it would not be good. But let’s be real, it’s not going to be good no matter who it is. 

I should know in about an hour… 

After my wife, Sue (or, Mistress Susan, as I am now compelled to address her in private), caught me cross-dressing six months ago – with three videos captured from several well hidden, high resolution cameras she had installed – I suddenly found myself very much in her power. This was quite the abrupt role reversal, as I had always lorded it over her during our 30 years of marriage as the man of the house and the primary breadwinner (and a very successful one at that). A prominent local businessman and a pillar of my community, I certainly did not want evidence of my little hobby to become publicly known. It would destroy my career and my standing in the community – especially as I had carefully cultivated my reputation as a “tough as nails” boss at my company and sort of an all around macho prick – not someone to be fucked with. The humiliation of being seen prancing around in dresses, high heels and pantyhose by my friends, coworkers and extended family would be beyond devastating. Having behaved as a prick towards my wife for many years, I did not doubt for a moment that she would follow through on her threats to expose me if I did not agree to do everything she wants. Yes, public exposure of my perversion would’ve been damaging to her, too, but it would’ve been far more damaging to me and she would’ve gotten a lot of sympathy (not to mention, very likely, a damn good divorce settlement).

So, publicly, I remain a successful executive and a fearsome boss. However, behind the closed doors of our mansion, my life is radically different now. When I get home from the office, I immediately remove my suit, change into any number of maid’s uniforms Mistress Susan has had custom made for me and begin my second job. In addition to weekday evenings and mornings – performing cleaning chores and serving her breakfast before I head off for my long workday – I spend the majority of my weekends waiting on my wife hand and foot, as her humble, domestic servant. I no longer sleep in the master bedroom, of course, but rather in the basement, in a spartan room that has been converted from a large storage closet into my maid’s quarters. All that is in that claustrophobic, windowless room is an uncomfortable cot, a clothes rack to hold my maid’s uniforms, and a dresser to hold my panties, stockings, and other feminine accessories. And a mirror, of course, for me to check that I am properly attired, as imperfections (wrinkled clothes, smudges on the polish of my high heels, runs in my stockings and so forth) are scrupulously recorded, and later strictly punished (there is also room for several punishment canes, straps, and paddles to hang on the wall, a constant reminder to me to be fastidious and obedient). Fortunately, I have a small bathroom in the basement that I am able to use with a modicum of privacy. For the time being at least, I am permitted to keep my few remaining suits and other masculine clothes in my old closet in the master bedroom. Occasionally, I am granted permission to go out to go golfing with my buddies, to go to a basketball game or to attend other events to maintain my social status. Even though that status is a total charade and likely disintegrating. But more on that later… In any case, it is still necessary for me to retain some male clothes. 

Only a few people know about our altered lifestyle – people Sue can trust. Namely, her younger sister, Gail, and Gail’s two children, our 18 year-old niece, Ashley, and her twin brother, Andrew. Gail‘s husband, Alan, passed away a few years ago, so I am spared that indignity, at least…

But, believe me, the indignities I do endure on an a daily basis are manifold. Gail never liked me and was particularly resentful of the fact that I never wanted to have children with Sue. Sensing her dislike, I always behaved quite condescendingly towards my sister-in-law and her family. I used to like to rub it in to Alan that I made a lot more money than he did and was always rather dismissive of, and impatient with, Ashley and Andrew when they were younger. The truth is, I’ve never been fond of children. Ashley has turned out to be a quite beautiful young woman. I remarked upon this to Sue about a year ago. I suspect that’s partly why Sue has decided to put Ashley in charge of lacing my corset, overseeing my curtsying practice and ensuring that my maid’s quarters are in the proper order. In other words, Sue knew that I have the hots for Ashley and, therefore, knew that my shame in routinely being scrutinized by Ashley in my humiliating clothing, and having to follow her commands, would be particularly acute. 

And it is, no question! What surprises me, however, is that I find it even more humiliating (if that is possible) to be seen as I now am by my nephew, who is my chief disciplinarian. Like his twin sister, Andrew is also quite good looking. As Ashley pulls the laces of my corset (unreasonably tightly, if you ask my opinion – which no one does, of course) or critically supervises my curtsying or my walking in high heels while balancing a book on my head, it is Andrew who stands nearby with a wooden cane or a riding crop in hand, always ready to sharply strike my ass should I displease Ashley with my efforts. He regards me always either with a contemptuous smirk or with stern displeasure, confident in his utter power over me.  Naturally, he’s is the the one who administers my more extended punishments, including my weekly ritual maintenance spanking or caning (depending on how I behaved that week or simply depending on Mistress Susan’s whims). These sessions are always attended by Mistress Susan, Gail and Ashley. The three women all take great delight in watching the young, athletic Andrew order around his sissy uncle and then flay the skin off my buttocks, thighs, and even occasionally my back and the soles of my feet.

As Miss Ashley – as I now address her – tightens the laces of the corset I will be wearing this fateful evening, I squirm in discomfort, watching the riding crop being wielded by Master Andrew carefully. Things have now reached a crossroads, and I am extremely anxious. You see, not surprisingly, Mistress Susan has taken a lover, and I am to meet him tonight. Well, “meet” is perhaps not the most accurate word, because Mistress Susan has explained to me that her lover is somebody already known to me. Specifically, he is someone who used to work for me for me at my company. The only other things I’ve been told about him by Mistress Susan is that he’s at least 10 years younger than me and extremely good looking. Oh, yes, and that he is “a real man“ – in stark contrast, obviously, to me.

Being the difficult boss that I am – or perhaps I should say “was,” as I have toned things down quite a bit at the office lately given what I now experience daily at home – I have driven away several employees over the years, so it is hard to know exactly who she’s talking about. I suspect it might be Lucas Corval. I believe I saw Sue flirting with Corval at the company Christmas party a couple of years back. He was a ruggedly handsome young man, probably about 15 years my junior or so, with dark, brown hair and an athletic build. Perhaps it was because he was so good looking that I was especially hard on him, eventually prompting him to angrily resign about a year ago and telling me at the time that “karma is a bitch” and that “I would get mine someday.” Hopefully, I’m wrong, because if it is indeed Lucas who is my wife’s new lover, it would not be good. But let’s be real, it’s not going to be good no matter who it is. 

I should know in about an hour… 

Sister to the left: “They say you can’t teach an old dog new tricks. But that’s not entirely true. We’ve managed to teach this one a few.”

Sister to the right: “Yes, but instead of using treats to train him, all I have to do is push the spike of my heel into his ball sack. He then learns quickly.”