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‘Tis the Season to be Servile, Ch. 08
Note: All characters are at least 18 years old. Similar to Lawyer2Maid (with a more seasonal focus), this is another story about an arrogant, highly successful man experiencing a brutal social downgrade — including being cuckolded and emasculated and becoming a sissified maid to his own family and former colleagues. If this is not your cup of tea, please read no further. If you are of the opinion that for a story to have value, it must be realistic, please read no further. Constructive criticism is always appreciated, but it is not constructive if the reader inherently dislikes or disapproves of the subject matter — especially if he/she continues to criticize the story several chapters in rather than simply stop reading it. Otherwise, please enjoy!
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I found it difficult to sit down the entire last weekend of November, following my brutal Thanksgiving Day punishment. This time, it was Lorena who took some pity on me and rubbed aloe vera lotion into my welts on Friday morning. Or, was it truly pity? Because, unlike Daphne, who had me lie across her knees to apply the balm, Lorena secured my arms above my head to a pulley Mason recently had installed on the ceiling of my maid’s quarters. I was dressed in white thigh high stockings with satin bows at the top and a white corset, which contrasted dramatically with the only other thing I wore: the black DOMINIX chastity cage. Lorena pulled the ropes securing my arms through the pulley sufficiently taut that I had to stand on my tippy toes. She next tightened my corset, and then rubbed her hand lightly across the welts on my ass and upper thighs. With her other hand, she reached around and squeezed my still tender right nipple. She was so close to me I could smell the shampoo on her hair and felt its silky touch on my right shoulder. She didn’t speak a word to me the entire time.
I had molested Lorena with my eyes multiple times while she worked as a maid around the mansion when I was still its master, but I had never physically molested her (well, perhaps I “accidentally” brushed my hand against her bottom a couple of times when she picked up my plate from the table or put a drink down next to me while I worked at my desk, but the contact was minimal). Nevertheless, she seemed more bold in her willingness to grab and grope me with each passing day. Still, when I felt the cold cream on her fingers touch my bottom, it was quite unexpected and it was difficult for me to feel anything other than grateful to her. I made a somewhat high pitched gasp of surprise when she first touched me; I was embarrassed by the effeminate nature of my exclamation, even before I heard her giggle. I was so thankful for the relief (and, honestly, for a gentle touch of any kind) that I couldn’t even feel much resentment when, after finishing applying the cream, she left me standing on my toes for another 20 minutes or so while she did god knows what in some other room. As Natalie pointed out, my toes had gotten quite strong by then.
True to her word, Natalie took Ryan to see her horse breeder friend later that morning, along with Mason. When I served them tea later that afternoon, it was clear that they believed they had found a good horse for Ryan. He planned to return to the breeder in a couple of days to ride the horse again before deciding for sure.
“I think you’ve found a beautiful horse, honey. Tomorrow afternoon, we’ll all go to the saddlery together. I’m friendly with the daughter of the owner, so I booked a private appointment at 2pm so she and her assistant can help you and Mason get all the gear and clothes you need. They have a tremendous inventory, everything top of the line.,” said Natalie.
“You’re friendly with the equestrian shop owner, too! Geez, Mom, you’re sure friendly with a lot horsey people for someone who doesn’t ride often,” said Ryan.
“Owner’s daughter. Her name is Suzanne. She’s a fascinating young woman. I think you’ll both really enjoy meeting her. But I love horses, so it shouldn’t surprise you that I know a lot of people in the community,” said Natalie.
“Your mother is friends with tons of people, in many different communities. Artists, actors, writers, tennis players. The list goes on and on. It never ceases to amaze me,” said Mason.
This is true. It never ceased to amaze me either when Natalie and I were together. A natural extrovert, she is charismatic, funny and confident, with varied interests. I always resented how easily she made friends with people when it was always such a struggle for me. I’m sure some would argue that my social struggles were mainly due to my arrogance, but it’s really not that simple. I had always been socially awkward, even as a kid, and I believe that my arrogance was, to some extent at least, a defense mechanism. It’s all academic now; the social skills of an indentured domestic servant are irrelevant.
“I happen to love talking escort bursa to talented, interesting people, that’s all. When I said that we’ll all go to the saddlery together tomorrow, I mean your father too,” Natalie said to Ryan, shockingly.
“Excuse me, Mistress. May I have permission to speak?” I asked.
“You may,” she said, before taking a bite of a scone.
“Why…why would you want me to come with you?” I asked, nervously.
“Having you present will be helpful for Mason and Ryan to visualize things when they select their ridding crops. They have such a large selection. Also, who knows, they might have some interesting clothing or accessories for the grooms. It’ll also do you good to get out for a change, Henrietta. You can’t hide away in the house all the time.”
“But…but…how will I dress, Mistress?”
“Don’t worry. We won’t make you go out in your maid’s uniform. Not yet, at least. You can wear those leggings I bought you last month — the hot pink ones — with one of the t-shirts you wear to do yard work and your Converse All Star sneakers. We really should buy you some pink Converse sneakers,” Natalie replied.
“Thank you, Mistress,” I replied, insincerely.
I now dreaded going out in public under any circumstances — but doing so for the purpose of helping my wife’s lover and my son choose implements with which to whip me was particularly upsetting. As if seeing my ass next to this crop or that one might somehow influence their choice of which one to purchase. Ridiculous. The real purpose of having me accompany them was to further my humiliation (one might reasonably wonder if that were even possible, but knowing Mason and Natalie as I do, I did not doubt it for even a second) by making it increasingly public. They had been hinting for a couple of months now that they planned to make my altered status much more widely known in the coming year; why not get an early start? Nevertheless, I was at least relieved that they wouldn’t be trotting me out in my maid’s uniform for the time being.
Still, the nylon/spandex, pink leggings — absurdly marketed as “activewear” — were plenty humiliating themselves. They were a deep, neon pink color, and while not transparent, it was possible to see the outlines of my underwear — that is, my panties — beneath them. I could not for the life of me imagine how any man other than one who is flamboyantly gay (or, possibly, a heterosexual male far, far more secure in his masculinity than I had ever been) would ever purchase such an article of clothing. And, of course, the bulk of my chastity cage was readily apparent beneath the leggings as well. Natalie had instructed Lorena to switch out the DOMINIX for the Perverse Pink CB-6000 (her whole color coordination fixation again) when she supervised me dressing on Saturday for my big trip outside of the mansion. I wore the leggings with an old, tight black t-shirt and my ratty, black Converse All-Star sneakers. Lorena also affixed a plain black choker around my neck; at least, it wasn’t the rhinestone-studded, pink collar. I was also spared the corset, for a change. This was a real treat, as I had spent most of my waking hours over the last several weeks tight laced.
When I regarded myself in the mirror, I was ashamed of how preposterous I looked. Although, I do have to say, my ass looked pretty damn good in the leggings — firm, shapely. My strict diet and nearly incessant physical activity while not asleep were having the desired effect, I suppose. Perhaps that it is why lately Lorena has been spending more and more time rubbing my ass with her hands when she helps dress me or restrains me. That Saturday, she rubbed my bottom for a minute or so through the leggings and then reached down to stroke (and gently squeeze) my balls through the nylon from behind, causing my cock to throb helplessly in its silicone prison. She even swatted me on the ass — I would say “playfully,” but nothing felt playful given the still sorry state of my bottom, even three days after my caning. But I had a troubling thought: if Lorena found my ass attractive, what about men? Was it possible that I was being viewed as a sexual object by men? And, if so, how should I feel about that? I found the thought incredibly humiliating…and yet, there is something…exciting, I guess (is that the right word?) about it as well. Is this simply another aspect of what Natalie meant by me surrendering to my humiliation?
It was an unseasonably warm day, and the short hoodie I wore with my ensemble left my ass fully exposed. When Ryan saw me, he laughed contemptuously. Was he looking at my ass? Please, god, no.
Of course, the contrast of how I was dressed compared to my wife and son and Mason made my appearance all the more mortifying. Natalie wore a short plaid skirt with black tights and black leather boots and a tight red blouse. Ryan and Mason were also both smartly dressed in khakis, polo shirts and leather shoes (black ankle boots for Mason and brown görükle escort loafers for my son). Try to imagine how the four of us appeared as we walked through the parking lot and into the main part of the store, what is best described as an equestrian superstore, with me remaining three respectful steps behind the others, my head bowed submissively. The room was huge and moderately crowded. We got lots of double takes and lingering stares, including from a group of girls in their late teens (probably a high school equestrian team). It was hard to determine, looking at them, whether they were more focused on Ryan or on me, but the juxtaposition of me with the others certainly must have been arresting. I heard a few of them giggle, and two in particular met my eyes with a derisive smirk. I tried to turn away to prevent them from seeing my face, or the bulk of my chastity cage through my leggings; but in doing so, I of course gave them an unobstructed view of my ass. I can only imagine what they must have been thinking about this unusual foursome (although, whatever it was, it no doubt paled in comparison to the reality of the situation).
Though my appearance was much changed, especially with my long hair, I was always fearful that I would be recognized while out in public. I had tried to keep a low profile when at my old firm, but one does not become a billionaire with a 17,000 square-foot mansion and a famous private art collection without having some photos taken of, and stories written about, you. While I’m sure that there were news reports about my sudden resignation from the firm, Natalie assures me that my transformation into her and Mason’s feminized servant was not yet part of the public record. Yet.
The three of us were led by one of the shop attendants into a large, separate back room with a couch, a couple of chairs and a coffee table. Along the right wall hung various riding paraphernalia: saddles, bridles, bits, halters, reins, saddle pads, boots, etc. On the opposite wall, there was dizzying array of riding crops, whisks, lunge whips, jumping bats and dressage whips. How could there possibly be so many different kinds?
After a few minutes, an attractive blonde woman, about 30 years old, entered the room followed by a slightly chubby man of similar age. She was dressed in tight, tan riding breeches and shiny, black boots with a white shirt and black shadbelly. The man, quite remarkably, was dressed in a jacket and tie, with short olive shorts and knee socks, and black shoes, much like a traditional British schoolboy. Except his shorts were shorter than most schoolboy uniforms, exposing much of his thighs, where red marks were plainly visible. It may have been an unseasonably warm outside, but certainly not warm enough to wear shorts. This was a new experience for me. Since the start of my subjugation in March, I had not yet laid eyes on another individual who was seemingly also in a state of subservience. The two of us briefly made eye contact.
The woman said, “Natalie, it’s so great to see you again!” embracing her warmly.
“You, too, Suzanne!”
Turning to Mason, Ryan and me, Suzanne said, “You must be Natalie’s three men. Well, two and a half, anyhow. Welcome to Jordan’s Equestrian. Then, smiling at each of us individually, she said, “Let me guess. You must be Mason. You are Ryan, obviously. And, you,” (and here her smile shifted from warm to mocking) “you, must be Henrietta, of course. You’re all exactly as Natalie described you.” She shook Mason’s hand and then Ryan’s. I was afraid to extend my hand, so it was easy for her to ignore me.
Suzanne continued, indicating the man in shorts: “This is my husband, Robbie. He’ll be assisting you today.”
“Hi, it’s nice to meet you all,” Robbie said, shyly.
“Ask them if the they want anything to drink, rocket scientist,” Suzanne said to him sharply.
“Yes, ma’am, sorry. Would any of you like tea or coffee or a soda or anything?” he asked awkwardly.
I would have loved a Coke, but remained silent as the others put in their requests. Once Mason, Natalie, and Ryan sat down to talk with Suzanne, Natalie said to her, “Perhaps Robbie can show Henrietta some of the grooming and stable cleaning supplies while we talk. We’re going to need more of everything with three horses.”
Robbie took me back out to the main part of the store, where the equestrian club girls and other shoppers got another opportunity to stare and speculate.
Robbie whispered to me, “Suzanne told me a bit about you. You’re a cuck husband, like me. Your wife is beautiful.”
“Thanks, I guess. Yours too.”
“I’m assuming the guy named Mason is her lover?”
“Yes.”
“Is he your master?”
“Yes. How did you know?”
“Well, first of all, my wife’s lover is my master. Second, looking at him and at you, and how you’re both dressed, it isn’t hard to figure out.”
“I guess you’re right.”
“Suzanne said he’s shopping for riding crops. To discipline you, I imagine?”
“He has a horse, too.”
“Many of the crops and dressage whips we sell are dual use, so to speak. My master fancies himself a real cowboy. He whipped me yesterday with the same dressage whip he’s probably using on his horse this very minute. Of course, he uses it very gently with his horse. I’ll tell you a little secret: I’ll bet close to a third of the crops and whips sold in this store are used primarily or exclusively on humans. Suzanne is in the scene, you see.”
“The scene?”
“The BDSM scene, of course.”
“Oh.”
“You’re really quite naïve, aren’t you?”
“I suppose I am.”
“I think Suzanne and your wife are going to be discussing Suzanne’s business proposition this afternoon.”
“What do you mean?”
“I really shouldn’t say too much. Who is the other person in your party? The young man?”
“He is…my…my son.”
“Your’e kidding?”
“No. I wish I was.”
“Wow, and I thought I had it rough. Look, I’d better show you the grooming tools and muck forks. I don’t want Suzanne to think we’ve been dawdling. Or, worse yet, talking.”
When we returned to the private room about 20 minutes later, Ryan was dressed in a polo uniform, including long, brown leather boots, a white jersey, white jeans and a black helmet. The jeans were somewhat loose fitting.
Natalie said, “Looking good, honey! But you won’t just be riding to play polo. You’ll be riding with Mason and me for fun and at other times, too, I’m sure. And equestrian attire can be fashionable even when not riding. Besides what you’re now wearing, I think you need to buy some black boots, some short, black jackets and least one long dressage jacket. I’ll bet that double-breasted French one we saw when we came in would look great on you. And you’ll need several pairs of jodhpurs, both tan and white — the tight ones, honey. Believe me, that’s what gets the attention of the young ladies.”
“Mom!”
“Don’t be shy, honey. Suzanne is a professional. And you’ve worked very hard in the gym. You shouldn’t be afraid to show off your hard work, as well as your natural gifts. Mason certainly isn’t, are you darling?”
“Hell no. If you’ve got it, flaunt it, I always say,” Mason answered, unsurprisingly.
When Ryan returned 20 minutes later, after further shopping in the main store, he was classically attired in skin tight white jodhpurs, nearly knee-high black boots and a double-breasted black dressage jacket with a tailcoat. He looked…formidable.
“Now we’re talking,” said Natalie, staring at our son proudly. “You should get at least two pairs of black boots in addition to your brown polo boots. You know how muddy they get, especially at this time of year.”
“The bootblack is going to be very busy,” Mason chuckled, looking at me.
“Speaking of the boot boy, it’s time my two men pick out their new riding crops. Suzanne, perhaps, you can suggest a few of your favorites, for various purposes,” said Natalie, with a smirk.
“I’d be happy to,” Suzanne replied. She pulled down four riding crops and two dressage whips from where they were being displayed on the wall.
“This dressage whip and this riding crop are my favorites to use in training and riding horses. They are quite gentle, as whips go, and a light tap is more than sufficient to encourage the behavior you want. These two crops, on the other hand,” — and here she started flexing and swishing one in the air — “are very versatile. You might use them to prod your stallion or mare to go a bit faster, but they’re also very useful — with the application of greater force, naturally — in training that special submissive or servant in your life. Let me demonstrate. Robbie, get your ass over here and into position.”
Robbie hurried over next to his wife, and bent fully over, touching his toes. He was surprisingly limber for a chubby guy (then again, he was still fairly young and probably had a lot of practice touching his toes with this martinet as his wife). She swished the crop in the air a few times (canes are not the only implements capable of producing that exquisitely foreboding sound), before bringing it down a few times smartly across Robbie’s bottom, which fortunately for him, was still covered by his shorts. Despite my empathy for my fellow submissive, I couldn’t deny that it was a very erotic sight watching this sexy woman in boots and skin tight clothing whip her husband in his juvenile get-up; there was a part of me that wanted her to bare his bottom and hit him with much greater force, but this was a demonstration rather than a punishment, of course.
“Jessie, my boyfriend, likes to use this to train Robbie in the gym. Although, as you can tell by looking at his fat ass, he needs a hell of a lot more training.” Natalie and Ryan both chuckled.
Suzanne then put down that crop, and picked up another one. “This Snowbee Horse and Pony Dressage Pro Whip, despite its name, I don’t recommend for use on any four-legged beast,” she said, again swishing it through the air. “No, this is best used to discipline our ill behaved two-legged beasts. I’ll show you.” Here, she brought it down harshly on poor Robbie’s bare upper thigh, causing him to cry out.
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