Personal Assistant Pt. 02

The month of June was a slow descent into a personal hell for Tom. It was never more than he could accommodate, but it was always more than he could really be comfortable with.

After the first day, Tom established a routine: wake up, go to work, spend 7-8 hours doing the endless grind of accounting, wait to discover what fresh humiliation was being piled on him, then go home and try to pretend that all was normal for the sake of his wife. As far as he could tell, he was successful in the last part. If Marge noticed that he was somewhat depressed, she didn't comment on it. She seemed happy for his 'promotion' and took everything in stride. Tom for his part felt less and less 'manly,' and their sex-life slipped another notch, going from about once a week to a perfunctory coupling on rare occasions.

Taylor maintained a friendly business-like behavior at all times, except for the mild, but increasingly degrading moments of what he called Tom's "attitude adjustment." Then, while there was never any anger or animosity displayed, the casual digs at Tom's self-image and manhood were relentless. Whether it was demanding that Tom accompany him to the executive men's room -- holding his penis while he urinated or wiping his ass after a bowel movement -- or fetching items from Candy's Bookstall (the local porn shop), it just kept getting worse and worse. Once, Mr. Taylor called Tom in at the beginning of the day and had him drop is pants and briefs. Casual nudity would have been bad enough, but that wasn't all the boss had in mind. Using the large bottle of lubricant Tom had purchased earlier, the senior executive lubed up Tom's anus and inserted a jeweled plug, insisting that Tom wear the plug for the rest of the day. It wasn't that the plug was overly large, but having to wear it and be aware of its presence for the whole day made Tom struggle to maintain his composure.

By the end of the month, Tom had progressed from holding his boss's cock and occasionally stroking it to climax, to kissing it and eventually to sucking it. The accountant often thought of quitting, but always realized that he lacked the moral courage to face prison and continued to follow orders, even when it meant returning to Candy's Bookstall and purchasing a portable DVD player with attached monitor, along with a DVD of male-on-male porn. Back at the office, Tom was made to watch the show with Taylor, while stroking his own cock until, against his own will, he ejaculated as the two men on the screen went about their own groping.

And of course, it didn't end there. First, it was having his head held while he was forced to take Taylor's cock deeper and deeper. Then it was having to take the whole 9" into his throat, gagging as it hit the back of his throat and spewed its load of semen directly into his stomach. Tom thought for a moment that he might suffocate on that load of cum, but thankfully his boss withdrew before it reached that point.

It was nearly mid-July when Mr. Taylor called him in and started asking some very personal questions.

"So, Thomas, how are you and Marge getting along these days? Are you still enjoying married life?"

"Sir?"

"Am I being too indirect? I want to know whether the two of you are still intimate. Do you share the same bed? How often do you have sex?"

"Sir, I..."

"Come now, Tom, don't be shy. Just tell me what I want to know."

"Yes, sir. Well, we do share the same bed, but the frequency of our love-making was decreasing even before this... this..."

"...this period of your devotion to me began?"

"Yes, sir. Since then, it's dropped even further."

"So when was the last time you actually fucked Marge?"

Tom blushed. "I'm not sure. Two weeks, three weeks ago?"

"I suspected something like that might be the case. So if you didn't fuck her for another week or two, she might not even notice?"

"No sir, probably not."

"Well, cheer up Tom. Tonight, you're going to pick up a package at Candy's and take it home with you. It's already paid for and will be waiting for you. I don't recommend you show it to Marge, but that's entirely up to you. You'll bring it with you when you come in tomorrow. Meanwhile, tonight I want you to go home and make a point of making love to your wife. If she's a bit reluctant, take her out to dinner or something, but don't fail to show her a good time, in AND out of bed. Is that clear?"

"So I'm allowed to have sex..."

"No, you are required to have sex with your wife tonight. Is that understood?"

"Yes, sir. Thank you, sir."

"Now go, make your wife happy."

Tom was only too willing to comply, and after making the required stop at the adult bookstore, he hurried home and found his wife in the kitchen. Walking up behind her, he kissed her lightly on the neck and murmured "Hello, love."

"My, what brought that on?"

"Only the fact that the new position has had me so busy and the realization that I've been neglecting you for far too long."

"Well, leave me alone for another hour or so, or there will be no dinner tonight."

"Would it ruin your plans if we ate out tonight? Or better still, if we were to order in from one of the better take-out places?"

"You *are* in a mood tonight, aren't you? You haven't been this affectionate since..."

"Yes, I know, and I want to make it up to you. I love my wife, and I haven't taken the time to show how much I appreciate her. There's nothing preventing a night in, is there?"

Nothing that can't wait until tomorrow. I certainly don't want to waste this opportunity."

Twenty minutes later, the two were dining on Beef Stroganoff on a bed of egg noodles with a side of snow peas and pearl onions, after which they retired to the living room to watch a romantic comedy Marge had been interested in seeing. They never finished the movie, however, as by mutual agreement they headed for their bedroom. There, Tom used all the skill and knowledge he had gained over 20 years of marriage to bring his wife to a very intense orgasm, with him climaxing within moments of her release.

The next day, Tom arrived at the office with renewed spirits. He was determined that, whatever happened that day, he would survive and continue until his obligation was complete. When he was called into Mr. Taylor's office, he delivered the package he had picked up, then waited to learn what new humiliation had been planned for him.

"So, Thomas, how was your night last night? Did you and your wife enjoy yourselves?"

"Yes, sir, very much. Thank you, sir."

"And your wife shares that opinion?"

"Yes, sir. In fact she commented on how much she liked the attention and wished that we could do that more often. She would almost certainly thank you herself, if she knew you were responsible for the fun she had."

"That's wonderful! Now, I take you for a pyjamas sort of guy. Am I right?"

"Sir?"

"Do you sleep raw, or do you wear PJs at night?"

"Oh, yes, I wear PJs. Why do you ask?"

"That's perfect. I feel certain you wouldn't want your wife to notice our next little adventure. Come around and stand by my chair, then open your pants. Do you know what this is?" Taylor held up an oddly-shaped metal device. "It's called a 'cock cage' or male chastity device. First you put on this piece, that goes over your dick and behind your nuts, a bit like a cock ring. Then this bit goes over your dick and fairly snug up against the first piece. You'll notice that it just barely leaves enough room for your balls to hang down between the two parts: that's to keep everything in place. And the last piece goes over the cock to join the first two. Now all I need to do is add this little lock, and the whole thing is securely locked in place. It's function, if you haven't already guessed, is to prevent you having any erections without my express permission.

"Here, let me show you how well it works." With that, Taylor pulled a vibrator out of his desk drawer and let it run against the metal of the cage. "Does that feel good?"

"Yes, sir... but... uh... my penis... it's trying to get hard, and the this thing won't let it. It.., ow... it's very uncomfortable, sir."

"That's just right then. Oh, and in case yo had some thought of perhaps picking the lock -- not too difficult, I would assume -- this version comes with a numbered mini zip-tie. If the parts should separate for any reason, the plastic breaks and I will know about it, thereby ending our special relationship."

"So the cage stays on..."

"Until I say otherwise, obviously. One more thing before you get to work today: here, I'm sure you recognize this little item."

"Yes, sir. It's a butt plug, a bit larger than the one you used before."

"Very good, Tom. You'll wear this all the time you're at work, being careful to clean and replace it any time you need to use the toilet. That's it, and I'll see you after office hours as usual."

The butt plug, a full inch in diameter, took some getting used to, but by the end of the day it had faded into the background of Tom's consciousness. It wasn't until it was removed prior to another deep-throat session that evening that it really became noticeable again. Tom had hopes that the session was the end of his torment for the day, but when he was sent home with the chastity cage still in place he realized that there was indeed a reason Mr. Taylor had asked about pyjamas. So long as he dressed and undressed in the bathroom, Marge would never notice anything out of the ordinary.

The rest of the week became fairly routine, with the butt plug being in place all day, the chastity staying locked on, and the occasional spanking and/or blowjob continuing all through the 6-day executive work week. The only difference on Monday was a change to a larger butt plug, this one about and inch and a half in diameter. By Saturday, Tom was wondering what else could possibly add to his degradation.

"Well, Thomas," Taylor said that evening; "it's been almost two weeks now since you started wearing you cage, hasn't it? I think it's time we celebrated. Here, I bought you a present. Since the building is pretty much empty, there's no reason not to try it on."

Tom took the small box and opened it to discover a 'baby-doll' nighty with matching panties inside.

"You want me to..."

"Strip everything else off and put these on, of course. I pretty sure I found the right size, but you can always exchange it at Candy's if you'd like a different size or color. You'll be wearing this gift every night after office hours, so it should be something you find flattering."

Tom did as directed, then went to kneel at his boss's feet.

"Oh no, dear. Before we do anything else, let's get that nasty plug out of there. I don't think you need that any more. Now come watch this video I got just for us. It's called 'The Making of a Sissy.' I'm sure you'll like it."

Taylor set the portable DVD player on top of his desk and turned it on. The screen showed a cross-dresser wearing very bad makeup approaching a man who began to caress and kiss 'her.' When it reached the part where sex was obviously about to happen, Taylor left his chair and helped Tom to stand and lean across the desk, moving the DVD player to where it could be viewed from this new position. Tom was scarcely surprised when Taylor moved behind him, grabbed his hips and inserted his hard, lubed shaft into Tom's receptive (if unwilling) backside.

Tom Was humiliated almost to the point of sobbing, but said nothing as the CEO thrust repeatedly into his ass. Then 10 or 15 minutes later, as the speed of the pounding increased, he noticed another sensation: his own penis was striving to escape the metal cage and become fully erect and... and... yes, he was cumming. Pulse after pulse of hot semen was dripping off the end of the chastity device onto the floor. If it hadn't been so humiliating in the extreme, it would have felt wonderful... one of the best orgasms of the accountant's life. Tom groaned in embarrassment and pleasure.

"Ugh.... ugh... AH-H-H... Thank you, my dear. That was impressive. Oh, and I see you enjoyed yourself, too. Now if you just learn to cook and clean, you'll make someone a good wife some day. Speaking of cleaning," Taylor said as he wiped the end of his own dick and Tom's ass with a tissue, "don't forget to clean up the mess you made on the floor. No, no, not with that... with your tongue. Don't want to leave any evidence around for anyone to see later."

As Tom got dressed and prepared to return home, he was quite certain he had reached the low point of his life, that things couldn't possibly get any worse.

He was wrong.