Diary of Ms. Pennington's Assistant

"Elena, show the boy-bitch how I like to get mouth serviced." Pennington commanded.

I moved down to join Elena between Pennington's quaking thighs. As Elena continued to pleasure Pennington, I swept her hair over her opposite shoulder so that I could see her, and so that I could kiss her cheek in greeting. I watched Elena as I massaged Pennington's feet, calves, and supporting Elena's oral ministrations with my own manual ones. We switched roles by means of Elena flipping over onto her back with the top of her head near Pennington's crotch, and I straddled Elena as I began to tongue fuck and then clit suck Pennington. Elena kissed my chest and furtively touched my cock.

"Elena, dear, fluff the boy-bitch's little pud. You remember how you used to when I brought boys back to the dorm. I need some cock, and he'll do." Pennington commanded.

Elena immediately scooted down until her mouth was below my crotch. She raised her head, and sucked my cockhead into her mouth. I was already erect, and did not need a fluffer girl, but neither I nor Elena protested. With great effort I maintained my concentration on Pennington's hot twat, which was drenched not only in her own slippery froth, but the mixed saliva of Elena and myself.

"Boy, I'm ready for some dick." Pennington said.

I crawled up and pushed my hard-on into Pennington's eager pussy. She was not tight like Elena, but it nonetheless felt immensely pleasurable. I was able to get a pussy pounding rhythm going in no time.

Pennington pulled me by the nipples down to a position on which my chest was smashing her plump breasts. Pulling her pillow under her head to raise it, she began to speak in my ear. "You'd better not cum before me. And when I am done you'd better pull out because my pussy isn't for your pleasure. Your dick is just a little dildo to make me cum."

Ironically, Pennington ordering me not to cum was not helping to achieve the stated objective. In fact, it nearly put me over the edge. I had to pause and tense up to avoid ejaculation. I managed to regain my composure and resumed. The next challenge came when Pennington summoned Elena to engage in a passionate round of French kissing with her. The two women's intimate moment aroused me greatly. Then Elena, following direction, repositioned herself so that she could massage Pennington's clit as I continued to fuck her. After a few minutes of this joint approach to Pennington's pleasure, our mistress began to uncontrollably quake on the verge of an intense orgasm. Following her command, I pulled out when she was on the downward slope of her orgasm, but, as I did, I lost control and shot a stream of my ejaculate across her stomach almost to her tits.

"One of you'd better lick that up immediately, I am not for you to be cumming upon!" Pennington commanded.

As I made the mess, humiliating as it would be, I would have done as Pennington require had Elena not beaten me to it. She ran her tongue from Pennington's black pubic patch to the end of the stream, slurping my essence up as she went.

"I have no more need of a cock today, so you are done here boy-bitch." I moved slowly away. I wanted to take advantage of the opportunity to talk to Elena. When I didn't move fast enough, Pennington clarified. "Get out, you little perv. I'm not here to put on a show so that you can whack your little pud." With that I left.

September 13, 2000:

...Then the day got weird. We didn't go in to the office after Pennington was bathed and dressed. She said she had some extremely important clients coming to visit at 10:00am. Pennington wanted some time alone, and I took advantage of the opportunity to edit some memos at Pennington's command.

I heard the bell, and knew when the clients had arrived.

Juanita soon came into the bedroom that I was working in across the hall from Pennington's bedroom. "Ms. Pennington would like to see you. Her guests have been seated in the white-room." Juanita and I had both become strangely comfortable with me being nude in her presence. I normally got dressed after I got Pennington ready, so that we could go to the office, but since we were not going in for an indeterminate time, I remained in my "house uniform", which is to say my collar.

I went to Pennington's room, and waited patiently for her to look up from what looked like a document that she was reviewing. "Sam and Jasmine are in the living room. Go ask them if you can get them coffee, tea, manual, or oral servicing." Pennington directed.

"What?"

"You heard me. I haven't finished reviewing this, and I need you to entertain them until I am ready. That is the only way you are fit to entertain. You can't juggle or tap dance, can you?" Pennington's tone was dripping with sarcasm.

This was the pinnacle of humiliation, and, like several times in the past, I considered telling her that I would quit before following that direction. She would, of course, fire me for such insubordination. She couldn't let me win even a small victory and maintain the level of dominance to which she was accustomed. I think that is what had happened to the number of previous assistants. They had all hit a wall beyond which they were unwilling to pass. When all was said and done, I didn't quit. I didn't like to admit the truth, that part of me was strangely addicted to the thrill of being forced to do things outside what I thought were my boundaries. I turned and did exactly as I was told. I reasoned that the worst that could happen probably would not. In my mind that worst involved the man wanting to be blown. I had no stomach for that. Would I do it? I didn't know as I marched from the residential wing of the mansion. How could I not know? I often didn't. On several occasions I had thought I wouldn't be willing to do something, and then I did. Each time, my illusions of personal boundaries became weaker.

I entered the stately pale living room with its white marble floor and fireplace, ornate moldings, and crystal candelabra. Almost immediately I felt the eyes on me. "Well, hello." There were two people sitting on a cream colored leather couch. The one speaking was clearly Jasmine. She had black hair cut in a bob, and wore a salmon colored dress that was made out of some sort of form fitting material that clung to her lithe figure. The man, Sam, was probably in his fifties, had gray close-cropped hair and a matching mustache. He wore a tweed sport coat, a solid white shirt, and brown slacks.

"Ms. Pennington will be a moment; can I interest you in some coffee, tea, or manual or oral servitude?" I managed to avoid choking on the latter words.

"Go ahead. You know you want to." It was Sam speaking to his wife Jasmine. "She's a bit of a nympho, and likes it rough."

"Oh, yeah. I'm ready." Jasmine said as she hiked the clingy dress up to her waist to reveal that she was without panties. With fierce speed she stood, approached, and kicked the back of my knee causing it to buckle. I fell to my knees with some assistance from her pulling down on my arm. She then pushed me over onto my side, and forced me onto my back as she sat roughly on my face. Pennington was demanding, but this woman was animalistic. She just wanted to mouth rape me, and the thought of it got her off with a quickness I'd never seen before in a woman. She pivoted her hips in a swift motion grinding her pussy over my face. I tried to suck and lick to pleasure her but she was so intense in smothering me with her pussy that half the time I was jus gasping for air.

"Suck it bitch." She said, and then loitered so that I could begin to concentrate my efforts on her clit. Despite my short hair she managed to get a grip with both hands and pull my face into her wanton pussy. "If you don't make me cum, I'm going to hurt you bitch. You like me rubbing Sammy's cum in your mouth. Are you a filthy little cum whore? Can't you get a woman off? Or are you just a little homo? If you don't make me cum, I'm going to have Sam ass rape you. No. That might be too enjoyable for you. Do you want a dick in your ass?" She continued getting increasingly vile with her sex talk and asking me questions that were apparently rhetorical - judging by the fact that my mouth was full at the time. The humiliating words seemed to be an aphrodisiac to her and brought her to ever heightened levels of arousal. Soon she succeeded in an intense orgasm. As her hips rolled and road across my face, I thought she might break by nose with the careless force of rubbing her pussy in my face.

"Lick the ass, bitch." Jasmine commanded while leaning back so that her bunghole was accessible. I rolled my tongue around the sphincter, and poked the tip of my tongue just barely into the tight hole as she finished her sex throes. When she got up my face was covered in a sheen of her sauce.

"Yeah, who's a good little whore; you're a good little whore." Jasmine said in a tone of voice typically reserved for speech to pets and babies.

As I sat, I saw a disconcerting sight. Sam had his cock out and in hand, and was lightly stroking it. I had no idea what he had in mind. Fortunately, Pennington entered just then and dismissed me...

[Those excerpts cover the highlights of my training period. For the next several years, the events that followed were pretty much in line with those described, and the excerpts provided are certainly enough to get the gist of the less mundane elements of my professional existence. During the most recent three years, things had gradually been changing. I have decreasingly been called upon to be nude, or to service Pennington's sexual needs. Pennington has been having quite regular appointments to which I do not accompany her. I only recently discovered the mysterious roots of these changes.]

December 22, 2009:

I entered Pennington's bedroom, and she was sitting at her little side table with a tumbler of Scotch in front of her and the bottle on the table. I had never seen her drink. Further disturbing was that her eyes were teary and bloodshot. I'd never seen her like this.

"I told you not to come in today. Get out. Go home." Pennington shouted despite her weakened condition.

"No."

"What did you say?"

"Look, I want to know what is going on with you, and I won't leave until I find out, or at least until you talk to someone else about it."

"You insolent son-of-a-bitch. You are fired."

"Fair enough. Now tell me what's wrong."

"Get out, or I will call the police."

"I doubt it. You don't know where the phone is, and I'm not sure you'd know how to use it if you did."

"Why are you doing this to me?" She was having trouble maintaining the façade of anger to camouflage her depression. Her front was cracking, and it was signaled by a subtle quaking in her voice and inability to look in my eye.

"Because I'm worried about you." I took a seat in the chair on the opposite side of the little table from where Pennington was sitting. The thought occurred to me that possibly no one had ever taken a seat in this chair before and it only existed for the purpose of attaining aesthetic symmetry. Alternatively, perhaps, they only sold such settings with two chairs.

"Why would you worry about me? I've been horrible to you."

"I'm not sure, and yet I'm here. May be it's because I don't know many people. Anyway, if I hated the way you treated me, I would surely have left."

She looked at me, took a deep breath, and blew it out. "I'm dying."

"What from?"

"Cancer."

"People survive cancer all the time. You've just got to fight."

"Apparently they do not survive this type, at least not when it is this advanced."

"I'm really sorry. Is there something I can do for you?"

"Thank you. You have every right to think of this as karma or whatever."

"Is that the kind of person you think I am?"

"No. It's an indictment of the type of person I am. You would be well within your rights. After a decade, it's a little late to say mea culpa."

"Maybe you don't need to. As I said, if some part of me didn't like this life, I would have left. That said, in general, I don't think that it's ever too late."

"OK. I'm sorry about how treated you."

"I accept your apology."

"Just like that?"

"Yep. I'm funny that way."

"Why did you let me treat you that way?" Pennington asked.

"I don't know? Maybe I'm a coward. Maybe I was good at it in a way that I wasn't good at anything else. Maybe I feel the need to be punished. Maybe I was evil in a previous life. Who knows?" I moved from the probable, to the wishful, to the absurd.

"I don't think you are a coward. You did, after all, just get yourself fired... By the way, you aren't really fired."

"Yes. I know, deary."

"How could you know? I didn't know myself until a moment ago?"

"That's so cute that you think you know yourself better than I do."

"How could you know me better than I know myself?"

"You didn't seem to know that you didn't really want to die alone, did you?"

"I do want to die alone."

"No you don't. You want to be holding someone's hand. I don't need to know you to know that, I just need to know myself. Being lonely sucks, but dying alone is an entirely different level of horrible. Maybe that's the real tie that binds us together."

"What's that?"

"A desire to not be alone, whatever the cost."

"You couldn't do better than an old bitch like myself?"

"Evidently not."

"You should have married Elena."

"Perhaps, but I lost my window."

"Hypocrite!"

"What?"

"Not but a few moments ago, you told me that it's never too late, did you not?"

"Touché."

"I'm tired."

"You should get some rest." I offered a hand to help Pennington to her feet. She took it, and I walked her over to her bed and threw back her covers. She sat down on the edge of the bed, and I brushed back her bangs off her forehead, and kissed her right in the middle of the forehead. "Sleep well."

"Will you stay a little bit, until I fall asleep?" Pennington asked in a manner more polite than I had ever heard her talk to anyone before.

"Yes, Ma'am." I kicked off my shoes and climbed in under the covers wrapping my arm over her and spooning her in a light embrace. She fell asleep shortly. I could tell by the subtle twitches and light snore that she went into a deep sleep.

Prologue:

Beatrice Pennington, partner in the law firm of Kale, Pennington, and Shipwright, passed away quietly in a hospital bed at Our Lady on January 27, 2010. I, Reginald Walcott, was with her in her hospital room when she took her last breath. Her siblings came only periodically to visit, and none were at her bedside when she died.

Her funeral was attended by 150 people, only two wept - myself and Elena Petrovskaya.