Diary of Ms. Pennington's Assistant

"Yes." She awoke and looked up at me. She seemed startled for an instant. She had most certainly come out of a sound sleep to notice a man whom she was not familiar with waking her. I had had similar experiences waking up in a hotel room, and not being sure where on earth I was. Pennington fairly quickly began to climb out of bed. I was happy about this. I was afraid if she dawdled, the tub and coffee would be cold.

Once she was out the king-size bed and standing, she raised both arms skyward. By now her ways were old hat, and I did not hesitate. The logical thought would have been that she was stretching. Instead, I knew that her action was my cue to pull the nightgown off over her head. Due to specialization of labor I could just throw the gown on the bed. Juanita, in her own words, was happy to pick up after me in exchange for not having to do my chores.

"Well." I had let Ms. Pennington go into the bathroom alone, and now she was calling out.

My first thought was that I had not stoppered the tub properly and it had run empty. I walked into the master bath expecting to see Ms. Pennington standing next to the tub angry and getting cold. Instead, she was in the warm water and soap suds to her armpits with her head laid comfortably back onto a padded head-rest. I looked at her a moment before I figured out that she actually expected me to bath her. I had assumed that bathing was one of those things like putting her hair up that she did on her own. At most I figured I would have to contend with the awkward act of toweling her dry, before taking on the same chores that I had done the previous day.

"Sorry, Ms. Pennington." I grabbed a washcloth, walked over to the tub, and sat on one of the steps at the tub's edge. I began to get the cloth wet and soapy. I washed her face with the soapy cloth and then rinsed from a pitcher of water Juanita recommended I put next to the tub. I preceded downward washing one arm at a time from shoulder to finger tips, and rinsing each in turn in the tub. I cupped water in my curved palms to rinse her shoulders because they lay above the water line. I then got to a seemingly intimate part of the process as I had to soap around and under her breasts in order to ensure the cleanliness of her heavy round orbs. Despite my willingness to adjust to what was expected of me, I was still self-conscious about this process. Based on the previous day's experience, washing her breasts too daintily might result in being accused of finding them ugly or of being a wussy, but spending too much time on them, on the other hand, could result in being called a pervert. I didn't try to guess what the middle ground was, but, rather, just tried to not miss anything without getting too engrossed in the task. Her stomach and ribs gave respite from concern. I washed her legs one at a time from the outside hip down to the toes. She lifted the legs to facilitate this so that I could get into the crook of her knee. I was left uncertain about how to negotiate the remainder of the bath.

"You missed my pussy. You need to pay more attention." Pennington said when I paused to consider my approach.

In truth, I hadn't missed it. It was, in fact, front and center in my mind. If this woman had boundaries, certainly they would reside between her legs, but apparently not. I kneeled at the tub's edge, and reached into the water self-consciously. I used the rag to wash the small mound of pubic hair. Then I worked back over her thick clitoris, inside and outside of the labia, and the perineum. I could not tell whether she was indifferent or enjoying herself. She continued to lay back with her eyes shut.

She then moved forward in the tub and leaned over the opposite edge so that I could wash her back and butt. Growing more confident, I washed her anal sphincter and ass cleft without a trace of shyness.

Then I drained the tub, and, as the water level fell with surprising rapidity, I took the hand-held showerhead in hand. I tested the water temperature on my own skin, and then began to rinse suds away with the showerhead in one hand while using my other hand to squeegee any soap residue off her body and toward the drain. When I was done, she stood and stepped out of the shower taking my supporting hand in her own to make sure she maintained good footing on the potentially slippery surfaces. She stood on a towel that I had prepositioned on the floor, and stretched her arms out wide.

This time it was quite clear that I was expected to towel her dry, but I had a bit of a problem. I had become fully engorged in, what was for me, the rather titillating process of bathing my attractive and curvaceous employer. By the time I realized my dilemma, I could not will myself flaccid.

"Do you want me to catch a cold here?" Pennington had dropped her arms and now had her hands on her hips as she looked back at me with a mild form of exasperation.

"Could I have a minute?" I inquired.

"For what? Unless you are physically ill I suggest you get over here and do your job." She replied.

I stood, and there was no way of not noticing the severe tenting in my trousers.

"Is that what this is about? You're embarrassed because you got wood giving me a bath?"

I was silent as I thought about how to respond.

"Well?... There are only two ways to answer the question. Either you got turned on by touching my naked body, or you were so disinterested in doing your job that you were having a sexual fantasy about an altogether different woman... or man... or animal - whatever you are into. So which is it?" She relentlessly continued the interrogation.

"The first." I admitted.

"Which one is 'the first'?" She was going to make me say it.

"Giving you a bath gave me an erection." I clarified.

As I was making my admission I had grabbed a towel and begun to towel off Pennington. Again I began with her face and worked my way down. I lifted her heavy tits with one hand and toweled under them with the other. I squatted to dry her pubic patch and legs, and then I helped her into her robe in a gentlemanly fashion.

"It's time for my shampoo." Pennington said. She had a styling salon type set-up for this with a chair that tilted back over a sink with a rounded "U"-shaped notch to accommodate her neck. I used the hand-held facet to rinse her hair out thoroughly, while running my fingers through it to expedite getting it wet throughout. Her hair was thick and full of body, and it took a while to get it completely rinsed. I shampooed her hair, rinsed, and repeated the process.

The rest of the day was pretty much like yesterday with the day being much less remarkable once we reached the office ...

August 21, 2000:

When I arrived this morning, Juanita had a box for me from Ms. Pennington that had a folded note taped to it. As Pennington did not seem like the gift giving type, particularly not for modest anniversaries like two weeks of employment, I had no idea what to expect. Even after such a short time in her employ, it should have occurred to me that she would capitalize on her latest breakthrough in humiliation. On Friday she had required me to drop my trousers and boxers. This was in response to my attempt to cover up the development of another boner. She called it was punishment for my attempt to be duplicitous. She proceeded to engage in some mild ridicule of my member, calling it "insubstantial." At any rate, I pulled the note off the box and unfolded it.

"This is your new uniform to be worn exclusively for all work on the estate grounds." This was all it said.

I now had a rough idea of what to expect was in the box. At least I knew enough to know it would be revealing and humiliating. I winced as I looked into the box. It was a simple stiff brown leather collar with a couple stainless steel D-rings sewn into it. It looked like something that had been purchased at a farm supply store rather than an adult toy store. I got the feeling that Juanita was suppressing a smile, but when I looked up she turned away. I thought about walking out, but I didn't.

Before I went to draw Pennington's bath, I put on the collar and stripped off my clothes, stowing them in the pantry. Juanita glanced at me as I walked through the kitchen. I couldn't tell if she was checking me out or was shocked by the nature of her work environment. I suspected Juanita didn't see many naked men of my age and relatively athletic physique, except, perhaps, Pennington's previous assistants. I moved quickly to minimize my exposure. Being nude in front of Pennington was one thing, I had more than seen her naked and she seemed unfazed by nudity. However, it seemed a little odd being undressed in front of Juanita, she seemed like such a conservative older woman.

When I entered Pennington's bedroom, she was already awake but not up. She lay on her side curled up in a big duvet and surrounded by pillows of various sizes. She seemed to be staring at an Orientalist painting on the wall that depicted a harem at rest. When I came in she followed me with her eyes as I walked to the master bath and conducted my duties. As usual, I had no idea what she was thinking.

When I turned around from kneeling beside the tub, Pennington was standing in the doorframe. "That suits you. I think it will work. You can wear one of Juanita's aprons when you work in the kitchen. I wouldn't want you to get scalded making coffee. Otherwise, I think we'll stick with this." As I approached, she reached out and looped her index finger through one of the D-rings and gave a few sharp tugs as if to make certain it was secure.

"Yes, Ms. Pennington." I said subserviently. I had been worn down from any resistance. Each victory I let her have was further enervating to my pride.

"It's better if I can tell whether you are having naughty thoughts, isn't it? If there is any hope of training you to be a proper servant, you must not be able to keep secrets." She inquired.

"Yes, Ms. Pennington." ...

August 30, 2000:

...Bathing Pennington proved an interesting experience this morning. When I got to her nether region, she took the washcloth from my hand and told me to continue until told to stop. As any pretext of my actions being about cleanliness was eliminated, I began to message her clit. Even in the water I could feel her natural lubricant begin to flow as I worked down from her clit to the rim of her vaginal opening. For the first few minutes, she just leaned back placidly. However, she even eventually began to subtly writhe her hips, and her breath would periodically catch.

"Ms. Pennington, would you like me to drain the water. I could rinse you with the massage head." I asked.

"Certainly, that would be nice, my little boy whore." She agreed.

I rinsed down the rest of her body before returning to my appointed task. I did linger a little longer on her breasts than usual, but she did not seem to mind. Her nipples were thick and pointy, and the skin of her areola was tightly wrinkled.

Before resuming manually stimulating her, I used the pulse setting on the handheld shower head to pummel her pussy with the spray. She pushed her hips forward into the chop of water. I then began to massage her clit between my thumb and index finger. When she seemed to be approaching climax, I directed the pulse of the shower onto her tightly puckered anal sphincter. She exploded. I sensed that she had been restraining herself earlier. She had not made much in the way of moaning sounds. However, now her whole body was wracked with spasms, and she produced a prolonged moan that I suspect Juanita could hear on the other side of the mansion. When she finished her orgasm, she just lay back as if looking up at the ceiling, but her eyes were closed.

I gave her a couple minutes to recover and then spoke. "Ma'am, would you like me to towel you off?"

"Yes, Reggie." She said after a pause. I was back to "Reggie" for a minute. While I didn't particularly like the nickname, it was certainly not derogatory like the terms she had often taken to calling me such as "bitch-slave", "bitch-boy", "boy-slave", or just "bitch".

"My friend Elena is in town this weekend, and needs some companionship. I told her you could help her Saturday afternoon or evening. I trust that won't be a problem." Pennington inquired without really asking.

"Yes, Ma'am." I said. I really didn't have any plans, and, while I was not eager to give up my precious free time, I wanted to keep my limited number of "get out of jail free" cards for when I really needed them....

September 2, 2000:

Juanita passed on a message that I was supposed to meet this Elena Petrovskaya at a restaurant called "Ratzi's" at 8:30 Saturday evening. I was not certain what to expect after Pennington told me I was to "help out" her friend as necessary. Did she need furniture moved? Something fixed? Who knew? ...

I arrived at Ratzi's a little before 8:30, and told the Maître d' I would be meeting Petrovskaya and that I thought there were reservations in her name. I was surprised when the Maître d' said that Ms. Petrovskaya had already arrived and was seated. This was a surprise. I assumed that any friend of Pennington's would likely make me wait just as a power play to assert her dominance.

The woman's punctuality became less of a surprise as I was directed to her table by a waiter. Almost as soon as I entered the restaurant's elegant dining room I noticed the single solitary woman. I observed her throughout my negotiations of the narrow spaces between tables. She seemed to be the anti-Pennington. Her long dark hair had a slightly disheveled quality to it as it flowed down to about the middle of her back. She was a thin woman without the voluptuous curves of Pennington. Beyond physical appearance, her demeanor seemed shy and diffident. She was looking down at a spoon as she twisted it between her thumb and forefinger, and did not notice my approach. When she did become aware of me in her peripheral vision, she looked up, and seemed to have a mild moment of panic. She half rose up to greet me - apparently realizing part of the way to a standing position that, as the woman, she was not expected to do so. This resulted in her standing in the kinked fashion of one who has to pee badly. In this awkward process, she extended the hand that had had the spoon in it to shake my hand and appeared to forget to set it down. The spoon hit the edge of the table and flipped to the floor clattering on the tile with a resounding echo that drew the attention of several of the patrons. Where Pennington was all confidence and control, this woman was awkward and timid.

I reasoned that the anti-Pennington couldn't be all bad. It should be noted that there were some superficial similarities between he two women. For one, they were both, in fact, women, and seemed to be of approximately the same age. They both had attractive faces, but in quite different ways. Pennington's face was -ironically - cherubic; whereas Petrovskaya looked like a slightly gaunter version of Uma Thurman.

We greeted and sat down. Both my curiosity and the convenience of it as an ice-breaker made me first ask how Elena knew Pennington. She said they had been roommates in their freshmen and sophomore years at a small women's liberal arts college in New England. Pennington had been a double major in Pre-Law and Business Administration, and Petrovskaya studied Chemistry. They stayed in touch even though Pennington moved out of the dorms in her junior year, and, thereafter, Pennington went to Stanford Law while Petrovskaya moved to Urbana-Champaign, Illinois to do her PhD in Chemistry. Petrovskaya now lived in Delaware; she had never been married (another thing she seemed to have in common with Pennington - but I suspect the "why" behind each lady's solitary existence was entirely different); and she worked for a major chemical manufacturer in Delaware.

I directed the conversation by asking questions and occasionally volunteering little bits of information about myself to round out the dialogue. However, Petrovskaya did seem to progressively warm up throughout the conversation, and was occasionally asking questions herself by the time the dessert, a delectable tiramisu, was delivered. She did not drink wine, so her growing confidence was not alcohol induced.

After dessert, Elena excused herself to go to the lady's room. The check happened to arrive in her absence, and the waiter set it down at Elena's vacated place setting. I thought this odd given that I was the man and the only one at the table at the moment, but figured Elena must have prearranged to get the check. My curiosity brimming, I asked the waiter if Petrovskaya had asked him to deliver the check to her.

Embarrassed, he said. "Oh, no... I just assumed... usually...." Flustered, he picked the check back up and began to hand it to me.

I said. "No. That's alright. It's fine where it is."

The waiter looked at me dumbfounded, probably thinking I was the biggest ass alive, and then turned away to resume his business. I came to the realization that he knew my situation better than I did myself. The violin music in my ears and the taste of espresso in my mouth were all part of the illusion of a date. However, to confuse my condition with that of a date was to invite embarrassment.

Elena returned in her floral print sundress that was out of place in this restaurant, but was nonetheless pretty and somehow endearing. She rooted around her purse, found a credit card in a brimming leather pocketbook, and stuck it in the little folding leather check valet. The waiter picked it up in an impressive show of multi-tasking as he was delivering two plates to another table.

After a moment or two in silence, I said. "You didn't have to buy me dinner, you know."

"Uhh... I know, but if feels more... normal... this way." She said.

The waiter soon delivered the check in need of signature. Elena swiftly added in a tip and signed it. Then she paused to finish her drink, and I suspected she was dragging her feet out of nervousness. She just sat quietly.

"Madame." I extended my hand across the table. As weird as this had become for me- starting when I made my little revelation- I saw little reason to not make it easier for the painfully shy, but quite likable, Elena.

Elena took my hand and stood, and I looked her in the eyes a moment before ushering her toward the exit. "What hotel are you staying at?" I asked.

"The Astor Arms." Elena replied.

"That's convenient." I noted. And it was, in more ways than one. For one thing, it was only about a block away, but a further benefit was that there was a pharmacy on the corner. Because of a combination of naiveté and a stunning inability to recognize that Pennington had no boundaries, I hadn't prepared adequately ahead of time by stopping at a drugstore before the dinner.

I asked Elena how she liked Delaware, and she said it was alright. She added that it was reasonably convenient to get away, as she was now doing. That was a telling statement.

"Mind if I run into the pharmacy real quick? I forgot something. I'll be right back." I asked.

"Certainly, but if you're going to get condoms, I already have some back in my room." Ironically, after the word "condoms" she realized what she was saying and halved the volume of her speaking voice to a whisper while looking around to see if anyone had heard the first half of her statement. Her awkwardness was so very likeable, and made me smile.

"Well, alright then. Let's proceed." I felt no need to continue the ruse.

Once in the room, I embraced Elena around the waist, brushed her long hair over her right shoulder, and began to kiss the left side of her neck. It began with a brief kiss on the neck, then working up to her cheek, and then to her lower lip. I took my time without pressing to enter her mouth. Elena was nervous. I could tell by a feint tremor in her voice, a slight tremble in her hands, and a general indecisiveness about how to respond. There was a sweetness about her nature, and her endearing awkwardness gave me impulse to be soft and gentle in my approach. Perhaps, I was enjoying the rare condition of being the more confident one in the partnering. Somehow finding myself in the position of gigolo emboldened me by eliminating all the usual guess work.