Personal Assistant Pt. 03

The following Monday Tom reported in for work and was told he no longer needed to use a butt plug, since he was now 'stretched enough to be useful.' Tom was thankful, but oddly let down at the same time.

"You know, Thomas, it occurs to me that we have had this... special relationship for -- what, two or three months now? I think it's time I finally met your family. Do you have any children?"

"No, sir. Our daughter Susan married months ago, so it's just Marge and me living there now."

"Well, I promised at the beginning I would protect your reputation, and I will continue to be on my best behavior. Would you and your wife consent to be my guests at Leonardo's this evening... or tomorrow evening, if that is more convenient. I don't intend to force her to be there, I offer as a gesture of goodwill for the excellent job you've been doing ever since the... incident."

"Are you sure, sir? Leonardo's... that's one of the priciest restaurants in town."

"As I said, you'd be my guests. Consider it a bonus for the fine work you've been doing for the firm, officially and unofficially."

"Thank you, sir. I'll check with her this morning and see what she says. Anything else, sir?"

"No, just be here at the usual time, dressed and ready for duty."

Within 30 minutes of returning to his desk, Tom was on the phone to his wife.

"Leonardo's? Oh, Tom, that's way out of our price range. Besides, I have nothing to wear, I'm in no shape to show up at a place like that!"

"Marge, Marge, relax. He's invited us to be his guests. if you feel you need to go shopping or get your hair done or whatever, we can afford it now. If it's too soon, he said tomorrow would do just as well. He simply wants to meet you and show his appreciation for all the extra hours I've been putting in."

"I really could use a new dress... and if I went to the salon in the morning... You say tomorrow is soon enough?"

"Yes, dear. Treat yourself to a spa day and some shopping -- within reason -- and I'll let Mr. Taylor know that we'll accept his invitation for tomorrow."

As Tom was stripping down and changing into the lingerie, he was able to tell his boss that the invitation for tomorrow night was accepted. Then he knelt in front of the other man and offered oral service for a minute or two, before being told to bend over the desk for a quick humping. He was slightly disappointed to not end up with a repeat of the huge orgasm of the previous rimming, but knew better than to complain about it.

That night, his wife was quite excited about the prospect of the following night's outing. She was a bit put out by Tom's lack of response to her displays of affection, but Tom plead fatigue from the long hours he had been putting in. (After all, he could hardly explain about the metal device surrounding his genitals, now could he? If only she knew how badly he wanted to provide her the pleasure she sought from him.)

The next day was back to the usual routine, ending with Taylor shooting a strong load of sperm-laden fluid down Tom's throat. Afterward, he said "The reservation tonight is for 7. Try not to be late."

"From her remarks last night, sir, I think Marge would skin me if I were even a minute late."

At 5 minutes before the appointed hour, Tom escorting Marge into the sumptuous surroundings of the city's premier dining establishment. He couldn't help thinking to himself that her time the last two days had been put to excellent use. From the stylish pumps on her feet, to the dress that perfectly showed off her figure to good advantage, to her tasteful makeup, to the new hairdo, she looked perfectly fabulous! Tom himself felt slightly under-dressed for the evening, but his wife looked like she was born to fit in with the monied crowd they were joining.

As the waiter led them to Mr. Taylor's table, Tom's boss spotted them and stood to greet them with a beaming smile on his face.

"Marge, this is my boss, Mr. Taylor."

"Thomas, we are not at the office, There's no need for such formality." He bowed slightly to kiss her hand. "I'm Jason, Mrs. Wilson, and I'm delighted to meet you. Thomas, you never told me you were married to such an exquisite creature!"

Marge felt herself blushing from the compliment. For her part, she was equally impressed by what she saw. Standing there holding her hand (for just a trifle too long) was a man about 6'1" who seemed to radiate confidence, competence and leadership. His chiseled good looks and perfectly groomed hair combined with an intense blue-eyed gaze that had her thinking of the trashy romance novels she had read as a teen. A second or two later, she manage to unlock her gaze from his and sit blushing (again) at the table, as the waiter handed them all menus. She and Tom looked, but couldn't bring themselves to order anything, especially after seeing the prices for everything.

Mr. Taylor -- Jason, she mentally corrected -- noticed their discomfort and came to the rescue. "I'm sorry, I'm being a terrible host. May I order for everyone? Yes? Jacques, we'll have the veal scallopini, and a bottle of Pinot Noir. Any recommendations on the vintage?"

"Perhaps the Chateau Margot, '57?"

"You still have a bottle? That sounds excellent."

"Oui, monsieur."

"Our meal will be awhile in coming. Would the two of you care to spend the time on the dance floor? The music is lovely, and it just seems like it's going to waste, with so few couples on the floor."

"Oh, I'm a terrible dancer, " said Tom.

"He really is, you know. Back when we were dating, I tried my best to get him to dance with me. The second time I succeeded, he nearly broke my foot. I've learned my lesson since then."

"Thomas, I'm nearly ashamed for you. However did you manage to win such a beautiful woman without being able to dance with her?"

"He had other charms back then, most of which he retains and shows off on occasion."

"You've been married how long, and no dancing?"

"Twenty years, next month. I've been keeping up my fitness classes, though. If I ever had a partner, I think I could hold my own."

"That sounds suspiciously like an invitation. If you won't dance with her, Thomas, do you mind if I do?"

"Not at all. This is her night, the two of you enjoy yourselves."

"Mrs. Wilson? I'm sorry that sounds so formal! Marge... that's almost worse. Marjorie, is it? Marjorie, will you do me the honor?"

Tom watched the two dancing and laughing together for what seemed like hours, but they returned to the table a minute or so before their waiter brought their order. The veal was exceptional, the light red wine complimented it perfectly, and the conversation was lively. Marge and Taylor -- that is, Marjorie and Jason -- tried repeated to draw him into their chat, but Tom felt like a fifth wheel as they discovered a mutual interest in the symphony, ballet and theater. By the end of the evening, Marjorie was positively glowing, and it was only with reluctance that she bid their host good night.

The next day, Jason -- Mr. Taylor -- was in an especially good mood. "Thomas, I am absolutely captivated by your bride! Her looks, her charm, her mind... I have never met a woman who so excited me. I was up half the night thinking about her. Even the sight of you reminds me of her, and I need to think a few things over carefully. Get to your office and get to work. I may have a request of you tonight, we'll see."

After a rather boring day, Tom reported to Mr. Taylor's office.

"Close the door and come here. No, don't bother to change, I need to talk to you. I've been thinking all day and I have a favor to ask of you. This is not a demand, but I really need to ask you for something... something I have no right to ask for. I know it's too soon after last night's dinner, but could you... perhaps.... possibly persuade your wife to invite me to dinner? Not tonight, obviously: as I say, it's too soon. But perhaps some time this week?

"If she declines, I won't hold it against you. I have no reason to hope that she would be the least bit interested. But if she is, I want desperately to meet with her again."

"I don't think you have to worry, sir. She seemed quite taken with you... she spoke of nothing else last night."

"Really?!? Then here, lets get that cage off you. You may need all your powers of persuasion. Before you go, though I really, really need you to suck me off so I can think straight!"

Tom knelt in front of his boss and opened his mouth to receive the already throbbing member, but was surprised that it was less than a minute before he was swallowing the large load of sperm that came spewing out of it.

Tom came in the next day and reported "I did as you asked, sir. She said she would think it over and call you directly when she reached a decision."

"Thank you, Thomas. That's all I could ask of you." At that moment, Taylor's phone rang and he answered immediately. "Hello? Oh, hello, Marjorie! How nice of you to call... Yes, I'm afraid I did Tom to ask you for an invitation... Tonight? I'd be delighted! No, no, I'm sure any meatloaf you make will be quite excellent. Can I bring anything? Alright. 6:30, you say? I'll be there. Thank you so much.

"Well, Thomas, it seems you were very persuasive. We'll forego your regular training tonight. Again, I want to assure you I'll be on my best behavior and will do nothing to disclose our arrangement or reveal your indiscretions. If you'll give me your address, I'll see you tonight at your home."

Promptly at 6:30 that evening, Jason Taylor was ringing the Wilson doorbell.

"Hello, Thomas. Marjorie, you have a lovely home... though not quite so lovely as yourself. I know you said not to bring anything, but I thought that even if it didn't go with your meal tonight, that you and Thomas might enjoy this pink Chablis I found the other day."

The meal and the conversation proceeded much as had that at Leonardo's two nights before. Easy laughter, pleasant conversation, personal anecdotes, and opinions on everything from movies to politics to favorite authors filled the room until the threee people moved into the living room.

"Marjorie, I'm sure you're wondering why I had this urgent need to see you so soon after our meeting earlier. Now, I have a confession to make, and you may find it a bit distasteful, so I beg you to hear me out before you have your husband toss me out of your beautiful home.

"Marjorie... I am smitten. I have never met a woman like you in my life. You are beautiful, charming, witty and intelligent. Thomas is a very lucky man to have found you and married you, and I only hope he has had the wit to tell you as much on a daily basis. I have become obsessed with you... with your looks, with your voice, with the smell of your hair as we danced, with every part of you. So obsessed, that what I am going to say next goes beyond anything I thought I would ever say, beyond any reasonable bounds of propriety or civilized behavior.

"Marjorie... dear God, how do I say this without offending you? Marjorie... I would love nothing more than to spend just one night with you, under any conditions you might set, for as long or short a time as you allow, so long as I might have the opportunity to share pleasure with you.

"There, I've said it. Tell me to leave and I will. Curse me for violating the sanctity of your home, and I'll accept it. Order me out of your presence, and you'll never see me again. But I had to let you know how I feel."

There were a few moments of absolute silence, then Marjorie asked, "And how would Mrs. Taylor feel about that?"

"What has my moth... oh. Oh, I see what you mean. There is no "Mrs. Taylor," there never has been. And that's the root of the problem.. When I said I have never met a woman like you, I meant that sincerely and literally. The dewy-eyed debutantes of my college years were fun to be with and fun to bed, but I could never be serious about them. As I grew successful, I was approached by dozens of women all filled with lust for the status or the money I could give them.

"But you... you are beautiful without using your beauty to entrap. You're charming without ulterior motive. You can just be yourself, and that allows me to just be myself.

"I have to say that I will not insult you by implying in any way that you might be bought. No matter what your decision, it will not affect your husband's job in any way. I won't offer you gifts or status or anything other than what pleasure I can bring you. I don't ask that you leave your husband, and in fact your loyalty to him is one of the things I find attractive about you. If you insist he be there with you while I intrude on your marriage bed, I readily agree.

"I don't want you to decide right now. Something this momentous demands careful thought and consideration. You and Thomas discuss it and once you reach a decision... whatever it is... let me know.

"I've said enough... or too much. And I've disturbed the tranquility of your home enough for one evening. I've meant every word I've said, Marjorie. And Tom, I hope you know that I'm being as frank as I can be. Whatever you decide, I adore you and respect you... and I hope that will be enough. Good night."

The next day when Tom went to work, his first action was to tell Mr. Taylor that Marge had not yet made a decision on his request.

"That's only to be expected, Thomas. She had no reason to expect anything like that from me and is no doubt trying to decide what she should do. I'll see you this evening as usual. Oh... and I'm sure you realize that what I said to her was true: no matter what she decides, it will have no bearing on our relationship."

After normal office hours, Tom changed into the nighty and went to kneel at his boss's feet.

"Thank you for being so prompt, Thomas. It has been a long and stressful week, and I think I'll need a little extra relief tonight. Open my pants and open your mouth, we need to get started."

Taylor was not to be rushed that evening. He made his 'personal assistant' lick his cock slowly, then forced the shaft deep into the open mouth and held it there until Tom started to gag, Then he pulled out only long enough for the kneeling man to catch his breath before taking two short strokes into the mouth and again holding the dick in place blocking Tom's breathing. Tom quickly lost track of time, but the session seemed to last for hours before Taylor instructed him to kneel on the chair beside the desk and bend over it with his ass in the air. With no further preparation or lubricant than Tom's own saliva, the CEO's hard phallus was thrust into Tom's anus brutally and repeatedly, banging away at the bowels within in an apparent attempt to beat them into submission. The junior had tears on his face by the time his superior finally thrust twice more and withdrew, leaving a thick wad of slime in Tom's gaping backside.

"Thank you, Thomas. That was quite satisfactory. But... hmm.. there seems to be something missing. Stop by Candy's on your way home and find a bra to match those panties... or better yet, get a matching set and bring it in tomorrow."

Sniffling, Tom used a tissue to wipe Mr. Taylor's cum from his butt, got dressed, and stopped by Candy's Bookstall on his way. While there, he quickly found a bikini set... but on impulse added an item he was not instructed to get.

The next day was Saturday, when most of the employees of Taylor/Durant were absent. When Tom went in to his boss's office and put away the bag from Candy's, he said, "I'm very sorry, sir, but Marge still hasn't reached a decision, or at least hasn't told me."

"You're 'very sorry'?! Come here," said Taylor, giving Tom a look that made him swallow nervously.

"Thomas, I don't know if that's the stupidest thing I have ever heard you say, or whether it is a lie used to tell me what you think I want to hear.. or both. If she had not reached a decision, then that means she is still considering it. She hasn't said 'no,' so she must think the proposal has some merit. She hasn't said 'yes,' which would indicate some loyalty either to you or to her marriage vows, or both. Her indecision means she is working hard to balance her desires with what she sees as the demands of society and her own moral standards...WHICH IS AS IT SHOULD BE! Since there are no staff in the immediate area, I'm going to give you a little reminder never to say anything -- especially concerning Marjorie -- without careful consideration. You are to place these binder clips on your nipples and leave them there until someone comes in, or until 15 minutes have passed. You are repeat this once every hour until 4:00, is that clear?"

"OW! Sir, that hurts!," Tom whined.

"IS THAT CLEAR!?!"

"Yes, sir." And with that, Tom went to his own desk and tried to focus on his accounting duties.

At 4:00, the accountant went in, stripped off his male clothing, put on the bra and panties as well as the baby-doll nighty, then added his extra purchase; a wig that very nearly matched Marge's ash-blond tresses.

Jason Taylor smiled. "That's a great improvement... and I like what you've done with you hair. Come here and sit on the corner of my desk."

Tom complied, and winced when Taylor ran his thumb over the now-bruised nipples inside the thin bra.

"One nice side benefit of your little lesson: it's made your nipples more prominent and more sensitive to my touch."

"Yes, sir."

"And I'm certain there will never be any need for a reminder, will there?"

"No, sir, there won't."

"Now, it almost seems a shame after you bought such a cute matching set of yellow underthings, but I don't think we'll need the panties tonight. Take them off, then lie back on the desk. Now hold your legs up... yes, just like that. Now comes the part you love: a nice coating of lube, and you can feel my cock slide home. Does that feel good, my dear?"

"Y-yes, sir," Tom lied. "Thank you, sir."

But although it was a lie, as Mr. Taylor continued to push slowly and gently into his submissive toy's butt, it soon became increasingly pleasurable. In and out the large organ pushed, in and out, with no rush or urgency to the movement. In and out, in and out, with the taller man occasionally brushing a very gentle, tender thumb over Tom's sensitive nipples. The soft pressure on his nipples sent electric chills down Tom's belly, and he started to moan. Still the slow, gentle, inexorable rhythm of the intruding hardness in his bowels rubbing against his prostate brought Tom closer and closer to what promised to be an overwhelming orgasm. On and on, and on the twin delights from above and below continued until, just moments before Taylor reached his own climax, Tom was startled to hear his own voice crying out, "OH... Jason!!" Then he passed out briefly, leaving hi belly coated with his own cum.

Taylor smiled.