“Wow, Uncle Henry, Mason really went to town on your ass with the cane last night, didn’t he?”, said my niece through marriage, Daphne, as she tightened the laces on my corset.
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“Yes, Miss Daphne.” I stood up straight, in my seamed, black, thigh high stockings and high heels, my garters framing my nearly bare buttocks (as my thong panties covered little) for Daphne to admire Mason’s handiwork.
“I guess you will do a better job of ironing his pants in the future.”
“I thought I had been very careful, Miss Daphne.”
“Well, not careful enough, obviously. Otherwise, your ass wouldn’t look like the American flag – without the stars, of course. But I’m guessing you probably saw stars when he tore into you,” Daphne snickered, amused at her own joke.
“Indeed, Miss Daphne.”
She gently rubbed her hand over the welts on my bottom, seemingly intrigued with the texture. “Does it still hurt a lot?”
Daphne is a very attractive 18 year-old woman, one I watched grow up. I must have been quite an intimidating authority figure to her until fairly recently. Even though I was not then facing her, knowledge of her beauty and of our radically altered relationship with each other caused my cock to twitch convulsively in its pink chastity cage at her touch.
“Yes, Miss Daphne. It is a constant throbbing pain now.” Indeed, two parts of my nether regions were now throbbing simultaneously, thanks to my inquisitive niece.
“Well, that throbbing should help you remember not to fuck up next time.”
“Yes, Miss Daphne.” I winced slightly, as she pulled the laces still tighter.
“I wonder if the welts will heal by Thanksgiving. That’s only two weeks from now.”
“Usually they heal in about a week, Miss Daphne. Unless, Master Mason is particularly cross with me.”
I was hoping that she might offer to rub aloe vera cream onto my bottom like she had once a month earlier (after a particularly brutal chastisement by Mason), but no such offer was forthcoming that November afternoon. I certainly would not be so foolish as to request her to do so, as it was not my place, and Daphne could be mercurial at times. Perhaps it was just as well, as the soothing effect of the cream was tempered by the pain of my cock swelling against its prison for 20 minutes on that previous occasion, as I lay across her bare thighs.
“That’s assuming you don’t fuck up again before then. Stand still!”, she said, firmly.
“My sincere apologies, Miss Daphne. Ah,” I gasped. “That is ever so tight. It’s getting difficult for me to breathe, Miss.”
“Aunt Natalie said for me to ignore your complaints. Corset training is a process, she said, and you will adjust to the greater restriction.”
“Yes, Miss.”
“I’m so excited that Ryan is coming home for the holidays! He hasn’t been back in the states since last Christmas. A lot has certainly changed since then, hasn’t it, Uncle Henry?”
“Indeed, Miss. A great deal has changed.”
“Are you as excited to see him as I am?”, she giggled. “He is your son after all.”
“In truth, I am exceedingly nervous about seeing him, Miss Daphne.”
“I’ll bet,” she said. “If I were you, I would be too. I’d be shaking in my heels,” she laughed.
Let me try to provide some context. My legal name is Henry Hathaway, although these days I am more commonly called Henrietta or, simply, maid. Until March of this year, I was a highly successful partner and senior portfolio manager – a master of the universe (yes, articles were published, as recently as nine months ago, that described me as precisely that) – at a premier macro hedge fund. That was until my biggest rival at my firm, Mason Draper, discovered and documented multiple instances of insider trading and securities fraud on my part, probably enough to send me to prison for 20 years (with good behavior). These are serious federal crimes, and long gone are the days when white collar criminals were sent to minimum security prisons that were more like spartan country clubs. No, the public tide has turned and white collar criminals now serve their time in some of the most notorious penal institutions in the country, where they are at the very bottom of the food chain (with the possible exception of child sexual predators). It is that harsh reality that was decisive in me accepting the conditions laid out by Mason – well, in reality, by Mason and my wife, Natalie – in exchange for his silence. The terms of my unconditional surrender. Why did I do this, you may ask? Why commit fraud to make millions when you were already a billionaire? Greed is the simple answer. Greed and power. An ill-concieved attempt to elevate my status in the firm even higher, to position myself as its next CEO. To achieve the ultimate triumph over Mason. Instead, I achieved the polar opposite.
It is not a good feeling to be caught red handed in an illegal activity by anyone. But especially not by someone with whom you have competed bitterly for over a decade, someone who you have humiliated professionally on numerous occasions, someone who is sleeping with your wife. Although, I wasn’t aware of Mason’s relationship with Natalie until after he caught me. After that, they no longer felt the need to hide their affair. In fact, rubbing it in my face in the most degrading ways possible became the name of the game. It’s fairly difficult, on the humiliation scale, to top enslaving the cuckolded husband in his own (well, former) home, in front of his family, friends and former colleagues (as well as any number of strangers) and turning him into a sissy maid. Nevertheless, Mason and Natalie continue to try their best to do so on a nearly daily basis.
I am 44 years old, and at 5’ 8” and 155 lbs, I’m a Caucasian male of slightly below average stature. I have lost 10 pounds over the last six months with what I will charitably call Mason’s and Natalie’s “encouragement.” I’m reasonably fit, as I used to work out regularly with a personal trainer before my radical change in circumstances in March. My trainer, a young woman, did not believe in bulking me up (nor was that the look I aspired to), so she favored cardiovascular exercise and light weight training. I no longer work out in the gym, but now get more exercise than ever before, as my days typically begin at 6 AM and end at 9 PM, often far later on weekends. I work seven days a week, except for the very occasional day off. I have always been a hard worker, but whereas my career in financial services was almost all mental labor (much of it at a desk in front of a computer screen), my life now is almost entirely menial physical labor. Domestic drudgery.
It is not easy being almost solely responsible for the upkeep of a 17,700 square-foot mansion in New Canaan, Connecticut. I was quite proud of this home, one that I had filled with expensive original artwork by famous contemporary and deceased artists. In April, in the presence of two top tier estate attorneys retained by Natalie and Mason (I declined my own representation), I signed over all of my assets – the mansion, the artwork, my brokerage and savings accounts, our homes in the Hamptons, and on Fisher Island in Florida, and Cap d’Antibes, France, my collection of sports cars, etc. – to Natalie. Natalie is 40 years old, with shoulder length, dark brown hair, a still sexy, firm body and legs that don’t end (she is two inches taller than me); she somewhat resembles the singer St. Vincent. Let’s just say that Natalie didn’t marry me for my body. Did I marry her for hers? Probably, at least in part. Although her irreverence, her love of fine art and her wicked sense of humor were also strong attractions. Being the target of her wicked sense of humor, as I frequently am today, is less desirable.
The decision to resign my position at the firm, to transfer all of my assets to my wife, to agree to live my remaining days as an emasculated servant to her and her lover – to essentially go from being a master of the universe to a slave in my former home over a period of 48 hours – was more straightforward than it may seem. It was really a simply a question of statistical analysis and game theory, tools I had used to great effect in running one of the most successful long-short hedge funds in history. Gaming things out, I came to the conclusion that my odds of of survival were much better outside of prison than inside. True, I would be facing staggering humiliation and emasculation in either scenario, but in prison, as the probable prison bitch of a hardened inmate (or, worse yet, multiple inmates), I was facing the prospect of being routinely raped. While I could not know precisely what Mason and Natalie had in store for me – I doubt that they knew themselves at that point – I thought that the probability of me being sexually violated by them on a routine basis to be relatively low. It was a bit of the case of the devil you know.
Natalie and I have one child together, Ryan, who turned 18 last month. Or at least we raised him together. Having learned of Natalie’s infidelity with Mason, and given our lack of resemblance to one another (both physically and temperamentally), I have now come to doubt that Ryan is my biological son. To be honest, I probably had doubts before, but suppressed them. Under different circumstances, I would demand genetic testing. Now, however, I am in no position to make any demands from anyone. Perhaps given all that has happened over the last six months, Ryan will choose to do his own genetic testing. For how could he possibly want to be the son of what I have become? Especially since his inheritance is secure.
You see, he has been attending boarding school in the UK for the last four years. I have seen him exactly twice during that time; during the second time, last Christmas, we barely exchanged a word. We are essentially estranged. He remains very close to his mother – who flies across the pond to see him frequently – but Ryan and I have had a very rocky relationship since he entered his early teenage years. Even before, to some extent. I spanked him three times when he was around 10, once when he broke a sculpture I had recently purchased for $30,000. I was so angry that I forced him to stand in the corner afterwards and to go to bed without dinner. Clichéd, yes, but no less humiliating for him. Perhaps he never forgave me for that. As a preteen and teenager, he was always headstrong and contrarian, especially with me. I used to think it was simply some Freudian Oedipal thing. But, in retrospect, I think it was more than that. I think it’s because we are so fundamentally different. At age 14, he was already as tall me (when he came home last Christmas, he towered over me) and is a natural athlete. An MIT economics graduate with a focus in statistical analysis, I don’t have an athletic bone in my body. Not only can’t I play sports, I have virtually no interest in them. I am completely inept when it comes to fixing or building things or doing other things with my hands, activities of innate interest to Ryan. So we missed the common opportunities for father-son bonding when he was young. I was so focused on my career, I was rarely even around, in fact. Despite me becoming a self-made billionaire, Ryan never respected me as a man. I can only imagine what he will think when he lays eyes on me now.
I will not be spared that indignity. Natalie’s contempt for me – especially for having jeopardized everything with my illegal activities – knows no bounds. The thought of seeing Ryan again in my present ignominious state fills me with dread, to be honest, not simply the nervousness I confessed to his cousin.
Him going away to a top boarding school in the UK was a compromise, brokered by Natalie, because Ryan and I had gotten to the point that we couldn’t stand each other. I sensed and deeply resented his undisguised lack of respect for me during his teenage years and was quite hard on him in reaction. When he was 12, I stopped buying things for him upon request (the expensive video games, personal electronics, apparel, sneakers, etc that all of his wealthy friends and classmates possessed in abundance) and instead gave him a paltry allowance – one that I made him earn, through hard work, such as mowing our 5 acres of land with a push mower. We had riding mowers, of course, but I argued that he was too young to ride one, and I thought the hard physical labor might teach him a lesson to treat me with more respect. It decidedly did not, having the opposite effect, if anything.
When he was 13 and 14, I insisted he do other things around the house to earn his allowance, such as repair the stone wall that separated our mansion from the street, clean the ten car garage, shovel snow, etc. After a particularly nasty argument, I actually started making him clean all the bathrooms in the mansion. “We can give the maid a break,” I argued to Natalie. “It will teach him responsibility and humility. I wasn’t above doing chores when I was a kid. It’s one of the reasons I became so successful.” In reality, I was being incredibly hypocritical, as I certainly did not do any kind of hard or unduly unpleasant physical labor when I was his age (or any age, for that matter, until the last six months, that is). Natalie and I had terrible arguments about my approach, but I was stubborn and basically had the attitude that since I earned the money, I made the rules.
Things reached their lowest point shortly after his 14th birthday when I caught Ryan rooting around in my office after I mistakenly left the door unlocked one summer weekend. My office was my refuge, it was sacrosanct, and I made it clear than no one – not Ryan, not Natalie, not the maid – was permitted there; I cleaned that room myself. That’s because I kept very private things – comprising things – there. Like what, you may ask? Well, occasionally I liked to dress up. In soft, sensual, frilly things. I was not a full-on transvestite. Not even close. But I did like to wear panties, tights and pantyhose. I loved the sensual feeling of the nylon against my skin, against my cock. Natalie and I were having sex very infrequently by that point, as she had seemed to lose interest. I now have a better idea of why, as her and Mason’s affair had already started by then. When we did have sex, it was perfunctory and she seemed bored. Being under endowed (just shy of four inches fully erect, with below average girth and balls), I had always been insecure about my ability to please her in the sack. In the early years of our marriage, she at least feigned interest, but that ceased to be the case. I’m sure that the tensions with Ryan and my obsession with work didn’t help.
So, increasingly, I found solace in my masturbatory sessions, wearing nylons and nipple clamps to stimulate my sensitive nipples. Often I would jack off to stories on Fictionmania and Literotica, gravitating to those featuring feminized, humiliated men. Was I a beta male? Well, yes and no. I had always been of the opinion that there are two types of men who are attracted to these kind of stories: the true betas who are submissive in all areas of their lives; and the men who hold positions of power and authority in most areas of their lives, including their careers, and who llike to play the submissive role from time to time as a form of escapism, a way to blow off steam, to temporarily shed the burden of always being in charge, of always being responsible. The former are the true betas, I believed; the latter are more like cosplayers. I was decidedly one of the latter. Or, at least, that’s what I told myself. Over the last six months, I have had the time and impetus to reevaluate many of my core assumptions, that one included.
In any case, when I caught Ryan snooping around my office that day, I lost my mind. There were no signs that he had found anything incriminating (I kept my stash of clothes locked in my bottom desk drawer and the key well hidden in my top desk drawer), but that wasn’t the point. How dare he do what I had expressly, unequivocally forbidden him to do? As punishment, I grounded him for three weeks. He protested vociferously about missing baseball games and tennis matches with his friends, missing other social events, but his protests and Natalie’s protests on his behalf were futile. I would not budge. From that day forward, he looked at me with outright contempt (sometimes causing me to wonder if he had in fact seen something in my office) and communication between us basically shut down. By the fall, it was determined that he would go to the UK for boarding school, rather than to Choate as originally planned.
These thoughts ran through my head that afternoon as Daphne continued to manipulate the tension of my corset.
Another tug of the laces proved to be too much. “Please, Miss Daphne, it is more than I can bear. Perhaps you could save some tightening for next time? I beg you.” I dropped to my knees at her feet in supplication.
Looking down on me imperiously, she said, “Well, since you are my favorite uncle – my only uncle, actually, ha ha – perhaps we can work something out. Three of my girlfriends and I are having a little get together next week at my house. Maybe I can ask Aunt Natalie if I can borrow you for the evening. You can serve us drinks and snacks. Perhaps I could ask each of them to bring over a few pairs of their favorite shoes for you to clean and polish while we watch a movie or hang out? Of course, I won’t say anything to Aunt Natalie about cutting you any slack. Quite literally.” She giggled. “What do you think?”
“I think that is an excellent idea, Miss Daphne, and very kind of you. Thank you.” I thought quite differently, in fact, but was desperate to halt any further tight lacing torture. I placed a gentle kiss on the toe of her sneaker, as I had been taught to do in such situations.
She motioned for me to stand with her finger and loosened the laces somewhat. I exhaled gratefully.
“You’re welcome. Now put on your scullery maid uniform. Aunt Natalie and Mason want you to scrub down the entire kitchen before you start practicing your cooking for Thanksgiving dinner.”
“Right away, Miss Daphne.”
As I changed before her, she said, “I know it must be pretty difficult for you, having never cooked in your life before until recently. Imagine, a 15 dish meal! That’s a lot more challenging than the three or four course meals you’ve been cooking.”
“Yes, Miss Daphne, you are correct.”
I now stood before her in my long blue maid’s uniform, white bib-apron and white cap, still wearing my black stockings and heels. Beneath my uniform, the same corset oppressed my waist.
“You’d better practice hard. The bar is going to be very high, with Ryan here, as well as my mom and dad and Mason and his daughter. What is that, seven guests?”
“Yes, Miss.”
“You certainly wouldn’t want to fuck up that meal. If you do, Mason will whip you so hard that you won’t be able to sit down until Christmas. Wait, I have an idea! You can cook a few of the dishes for me and my girlfriends for practice when you serve us next week. The mushroom soup, kale salad and brussels sprouts. We can then review your dishes. It will be great practice for you.”
“You are too kind, Miss Daphne.”
“I really am, right? Now run along and get busy, uncle dear. Chop chop.”
I curtsied to her, and hurried off to the kitchen.