Full Rigor Pt. 07

(SPOILER ALERT: This strange story is getting progressively stranger, so please be prepared, and remember this warning before you comment! Michelle Harkins, MILF nurse and mother of two college kids, persuaded her lawyer husband Rich to allow her to live out her lifelong submissive fantasy by self-indenturing herself, spending over a year as a legal sex worker/slave. Encouraged by their dominant friend, surgeon Shirley Holmes, Rich decided to enact his own version of that same fantasy once Michelle finished her term of servitude. As a plastic surgeon, Shirley gave Rich breast and butt implants to make him into a hermaphrodite "sissy." Please note that this is NOT intended in any way to reflect the psychology of true male to female transgenders; Rich had no doubt that he was fundamentally male, but had chosen to become a feminized slave (preferably serving women rather than men) as the ultimate form of helpless submission. After training at the Pearson Pussy Ranch to perform as such, "Sissy Rikki" went to a specialized slave market where his six-month contract of servitude, offered by Michelle as his owner, was bought by Laura Simmons, a successful lawyer who had previously "trained" the man who was now her masculine husband Dan in the same feminized manner (See the story "Adjusting My Attitude.") Laura expected her new slave to act as a para-legal at her law firm.)

(Rich or Rikki Harkins' perspective)

Mistress Laura worked incredibly long hours, and yet she didn't want me around her office during daytime business hours--for reasons that will become apparent below. So, after buying me some (female) business attire, she had established an Uber account for me and given me a cell phone to arrange my own transportation, telling me to get to the law offices about 4:30 p.m. on the first day I was to work for her.

I presented as a female office worker, with (silicon implant) 40C boobs and (again implanted) shelf-like butt, not to mention shoulder-length hair, daytime makeup, a modest collar on my neck, and a skirt hem stopping just above the knee. I could see the Uber driver checking me out in the mirror, and he tried to strike up a conversation; Most free people equate wearing a collar with being a slut, simply because the slave has to perform sexually at the direction of his/her owner. Yeah, that's what thrilled me about slavery, but it DIDN'T mean I was permitted to have sex with everyone I met. I was respectful to the driver but tried to avoid saying too much. He was only the first hurdle I had to face, and I knew that much more of a challenge awaited me at the law offices of Harriman, Kingsley, and Gaylen, a major partnership.

Mistress Laura had explained it quite bluntly: about ten years earlier, the partners had decided to solve two problems at once. On the one hand, their secretaries and para-legals were overworked and tended to quit, so the firm needed affordable and reliable administrative help, performing routine tasks to retain those it already had. On the other hand, too many of the (mostly male) attorneys in the firm thought with their little heads instead of their big ones--if the firm didn't do something about sexual harassment, it would lose even more of its skilled female assistants and get a public relations black eye about MeToo and equal rights. Their solution was practical but hardly ethical: they started a policy of deliberately purchasing feminized sissies to work in the office, with the unspoken corollary that, since slaves could not refuse sex to a free person who controlled them, the testosterone-driven male attorneys could get away with groping the sissies and demanding sexual favors from them. (Hell, before I had self-indentured, Mistress Laura's husband Dan had told me that, while working there as a feminized slave, he'd had to give the managing partner a blowjob--after which that partner had tried to buy him from Laura!) Mistress Laura told me that some of these slaves were indeed genetic women, others were transgendered but had reluctantly sold themselves to pay for the medical transition, and still others were, like me, males who enjoyed being dressed and dominated AS IF they were submissive women. (No, I don't assume that all women are "naturally" submissive; I'd been fortunate to encounter several, like Dr. Shirley Holmes and Mistress Laura, who were VERY self-confident and assertive, not to mention smart and drop-dead gorgeous--MY kind of woman, at least when I was in submissive mode.) Most of the attorneys at Harriman, Kingsley, and Gaylen were equal-opportunity harassers; as long as their target wore a collar and looked attractive in a skirt, the guys were eager to take advantage of her or him. I found out gradually that my possession of fully-functional male genitalia wasn't much of a consideration to these clowns; they were still happy to fondle my butt and boobs and if I didn't have a cunt they would simply shift to stuffing my mouth and anus for their pleasure. Since a lot of their enjoyment came from the power trip of forcing themselves on another person for their own pleasure, and since slaves were by definition unable to resist such use, sodomizing one of the feminized office assistants was a match made in chauvinist/sexist heaven.

To be honest, I was conflicted about that. I still thought of myself as a heterosexual male, but I knew when I had implant surgery and self-indentured as a "sissy" that I was actively INVITING this kind of use and abuse, and both Shirley and the Pearson Pussy Ranch had made sure I was prepared to give such males a "fun ride" even if I didn't enjoy it. Resistance would only "out" me as a male and might end up costing me additional years of servitude. Laura made it clear that she was taking me to the office for my legal mind, not to indulge her "juvenile" male colleagues, but I might still have to put up and put out for them.

*****

The first few days, because I arrived in the late afternoon, I was lucky. Most of the people working at that hour--and often well into the evening--were trying to get their work done, not their rocks off. So as long as I hid in the two offices belonging to Mistress Laura and her daytime, free citizen paralegal, Jenny Powell, I didn't encounter much harassment. Of course, there was always the occasional crude comment, swat on the fanny, or squeeze of a boob on my way to and from the (ladies) restroom.

Jenny was a marvellous administrator and computer whiz who had worked with my owner so long that she could anticipate Mistress Laura's needs. Find a precedent, proofread a contract, and pick up the boss's best suit from the cleaners before a negotiation--all were in a day's work for her. But Jenny had two growing children who needed her to be home in the evenings and weekends, which is when much of the serious work gets done in a law firm. So she was overjoyed to see me and especially to learn (although I didn't explain my background) that I knew a lot about legal work, allowing her to leave at 4 p.m. every day with a clear conscience. She insisted that I address her as "Jenny," telling me that servitude didn't matter when we were working together--"We're all galley slaves in here, just keep stroking!" [As you'll see, "stroking" had a double meaning.) Occasionally she would compare me, favorably, to another "sissy slave" named Danielle that her boss had brought in a few years earlier. I realized that she at least PRETENDED not to recognize that "Sissy Danielle" and her boss's businessman husband Dan were one and the same person. She never even winked when mentioning him or on the rare occasions when he telephoned or visited the office. In other words, Jenny was a model of discretion and efficiency, a Mary Poppins of Paralegals and Personal Assistants--Practically Perfect in Every Way.

Which made her a really hard act to follow, even if my dick wasn't distracting me by trying to get HARD inside my chastity belt. I worked flat out for several weeks, being the second shift paralegal in the office and the eager housemaid at home. For years, skilled paralegals had made my job as an attorney easy, but now it was payback time. Most of the time, I was simply happy to please Mistress Laura and frankly enjoyed being dressed as a woman and serving in a subordinate role. She was a good boss who encouraged me with the four C's--Courtesy, Compliments, and (occasionally) free time with my Cock released from the Chastity Belt. In my previous (free) existence I had become jaded and frustrated by the never-ending stream of irritating little issues that clutter an attorney's life, so serving in a different, sexy role in a different law firm actually made it FUN to go to work.

Then, on my second Saturday as Mistress Laura's collared office companion, I encountered the same hazard that had humiliated Dan--the managing partner, Bill Kingsley.

Objectively speaking, he was a rather handsome, distinguished-looking guy--about 60 years old with silver hair and a body he apparently kept in tune with frequent racquet ball and tennis matches. In other words, the perfect aura for a senior attorney--but not someone I ever wanted intimacy with.

It being a weekend, my owner was dressed informally in burgundy-colored jeans, a pretty blouse, and pink sneakers with her hair in a pony tail and minimal makeup--she still looked like a million bucks, making me understand again why Dan Martinson had gone to the extreme of self-indenture to woo her; if I didn't already love Michelle it would have been easy to develop an (inappropriate) crush on Laura, and I certainly looked forward to the rare occasions when she got me off in order to give herself pleasure.

I was dressed much more formally--by social convention, slaves only wear clothing for safety or to blend into the environment where they labor, so, even though the law offices were half-empty on a weekend, I had to look like an administrator or secretary. Everything was in different hues of blue--light blue skirt and blouse, dark blue thigh-highs, low heels in Navy, and a tight belt to exaggerate my waistline. Maintaining the fiction that I was a female office worker, I wore muted daytime makeup. (OK, some of that clothing felt very sexy, but I dressed that way because my temporary owner wanted me to blend in. Honest!)

I was aware of a few other people working in the office that Saturday, but everything was so quiet and low key that I felt relaxed, much less threatened than when surrounded by would-be legal wolves during the week. But, I knew immediately that my luck had run out when Mr. Kingsley entered Laura's office. He asked to "borrow" me to "help" him for a few minutes. Out of courtesy, Mistress Laura had to agree, although she rolled her eyes at us and found a way to gently tell him that I was her personal house slave and not part of the firm's "sissy pool." This sounded EXACTLY like the situation when Dan had been used, which put me on my guard.

Kingsley walked me back to his office with his hand firmly cupping my right buttock, making idle conversation about how long I had belonged to "Mizz Simmons," what legal experience I had (he didn't seem to recognize me even though we were once on opposing sides in a major contract dispute, so I fudged the truth and said I'd started law school a long time ago), did I like this work, and so on. Once we entered his large office, going past an empty assistant's desk to his inner sanctum, he just swung the door shut, sat down in his swivel chair, and casually directed me to "kneel . . . mouth." No surprise, but also no way out, so I followed directions, using my tongue, lips, and hands in an effort to bring him off and end this encounter as quickly as possible.

But Kingsley was too smart--or perhaps too experienced at exploiting slaves--for that. I repeat that I was not and am not trolling for homosexual sex, but his dick was impressively large and so I got some kind of submissive thrill out of the situation. In less than four minutes, his shaft was rigidly ready for action, standing out from a bed of silver curlies. When my nose made contact with that hair, I was bracing myself for the (literally) distasteful requirement to swallow his cum. Then he abruptly pulled out, stood up, and ordered me to do likewise. He directed me to turn around and face the desk, at which point he rucked my skirt up and pushed my panties down to my knees, leaving my rear end uncovered. In an instant, that large, wet dick was pressed against my bare butt while his hands came around my body to maul and manipulate my tits. Having a mind (or at least sensations) of their own, my nipples both stood up as did my own cock--betrayed by my own submissive sexual arousal, damnit.

"Bend over the desk, sweetheart," came a gruff command, along with a firm push on my shoulder. This is one of the many situations when slavery allows nothing but complete obedience. Once I had complied, I wasn't surprised when his next direction was "reach back and spread your cheeks--show me your boi pussy." Crap--here it comes, or should I say "cums?"

He had one more preparation, though. "What does a good slave say in a situation like this? What's the mantra?"

Get it over with, I thought to myself. Cringing and trying very hard NOT to clench my teeth, I used a soft, girly voice to dutifully repeat, "Master, please shove your monster cock up my boi pussy." That was the LAST thing I wanted at the moment, but there was no way out. I never dreamed I would be thanking Pearson's Pussy Ranch because it had trained my colon to handle such intrusions, but damn, he had to be at least eight inches long and heaven only knows how much around, I thought, willing my muscles to pretend they were defecating in order to ease the entry I couldn't prevent or resist.

"Goood Slut," he said, as if I were a dog that had just performed a trick correctly. Confirming that image, he even patted my head! Then I heard a desk drawer open and my rectum got flooded with something liquid, probably lube. This guy is a regular Boy Scout, I thought grimly--always prepared! I was struggling not to laugh out loud when I felt the head of that impressive dick push past my slippery sphincter. Truth to tell, the combination of the lube and my previous training made the entry almost painless, but I knew what he would expect--what I would expect if a woman permitted me to sodomize her, so I let out a quiet, almost happy groan. Get it over with, I kept telling myself.

"Feels good, doesn't it, Sissy?"

"Yes, Master." That was an exaggeration, of course, but when someone is violating your ass, it's wise not to antagonize him!

"OK, slut, let go of your butt cheeks and reach across the desk to grasp the far side." I could barely reach that far across his executive furniture but holding onto the desk seemed to stretch me out, helping me handle his invading prong.

In the space of less than three minutes, his shallow but rapid thrusts opened me up until I felt his belt-buckle pressed against my bare back--as the saying goes, he was balls deep inside me, and I was laboring mentally to adjust physically--I didn't even want to THINK about being his bitch! Once well inside me, he paused for what seemed like a full minute before he began pumping again, gradually increasing the depth and speed of each penetration until my body and indeed the desk was shaking with each forward thrust.

Now I was REALLY conflicted. On the one hand, I would MUCH rather have any kind of intimacy, even plastic pegging my butt, with a woman, especially one I respected like Laura. On the other, I had to admit that this felt kinda nice, stimulating my nerve endings and my prostrate in a way that caused my own dick to erect. You couldn't get much farther down the power transfer graph: Six months before, I had been a successful MALE partner in a large law firm, sitting behind my own massive desk while I directed a battery of attorneys and others in a complex negotiation. Now, I was pinned helpless across the desk of another successful attorney, my breasts pressed into the plexiglass cover of the desk while "Master Bill's" hands held my shoulders down and his hips sawed a dick in and out of my anus and he kept mumbling inarticulately about "nice, tight ass." This was professional courtesy at its finest, one attorney reaming another's ass and not even charging him for it; I wondered how Master Bill could put that down as billable hours! Probably something about "FUNDAMENTal exploration of an opportunity." A random thought caused me to chuckle quietly; too late, I attempted to suppress the sound.

"What are you giggling about, Sissy?" came the calm male voice from above and behind me while he panted very quietly, exhaling in a rhythm with his outward strokes.

"I'm sorry, Master--no disrespect, but I was just thinking that it's true what people say about attorneys."

"What do they say?" came the immediate reply although he must have had a good idea where I was going.

"That you should never turn your back on a lawyer or he'll end by butt-fucking you. UMPH! Sorry, Master."

"No, don't apologize," Bill replied, and I could hear amusement in his voice. "You're absolutely correct. And in YOUR case, it's a nice, tight sissy slut butt at that. WHAT a hot piece of ass!" That statement was accompanied by another SLAM! into my rectum. His words reminded me of my training, so I immediately began to flex my muscles, causing my colon to contract around his shaft in hopes of bringing this invasion to an end. Startled, he groaned.

Then I heard him pick up his phone receiver off the desk, punch four numbers, and speak to whoever answered his call. "Jim? Bill. Do you have a few minutes to come into my office and help me finish something? Thanks."

As he hung up softly, he told me that my "smart mouth" needed something to keep it occupied. A minute later, in walked another older guy in a suit, a guy whom I had already learned was James Harriman, one of the founding partners of the firm. At Master Bill's invitation, he unzipped, whipping out a fairly large dick, and plugged my mouth with it. The two of them soon established a rhythm that made me feel as if I were sliding back and forth along a long, fleshy shaft--as Bill thrust in, his partner pulled out and vice versa. I had to focus on just breathing around Harriman's aging dick. While physically uncomfortable, I had to admit that the sensation of my body being completely controlled and occupied by two other human beings was submissive nirvana for me. And they clearly enjoyed using my entrances as receptacles for their dicks, climaxing within seconds of each other (my sissy dick also shot off, fortunately leaking onto the carpet rather than the desk.) Even though I knew that I was fundamentally male, at that moment I could have hummed along with Shania Twain, "Man, I feel like a woman." Or at least a submissive slut in the role of a woman.

Moments later, Harriman freed his prick from my mouth, zipped up, nodded when I displayed his goo on my tongue, and walked back out of the office as if nothing had happened and no one else was there. Master Bill was more winded, leaning on top of me for a minute while his questing hands slipped underneath me to squeeze my breasts as if they were sacks of mashed potatoes. But then he stood up--I felt that shaft withdraw from my well-stretched starfish and heard his pants zipper closing. "Nice, tight, sissy ass," he said for at least the tenth time as he slapped my right buttock HARD--apparently that was all the thanks and praise that a slave slut could expect after helping upper management get off at the end of a long day.

Once I caught my breath, I pulled down my skirt and staggered out of his office. I met Mistress Laura in the hallway--she had a worried look on her face and my purse in her hand, and she supported me walking (more like staggering) to the nearest ladies' room. In addition to lipstick and makeup, she had insisted that my purse always contain a travel bottle of mouthwash and several tampons. Now, I found out that the latter were not just intended to support the thin fiction that I was a woman--I actually used them to absorb all the lube and jism that would otherwise have leaked out of my rectum for the next several hours, staining my clothing. Craning my head to look at my butt in the bathroom mirror, I saw the large, pink handprint where Bill had slapped my rear end.