Diary of Ms. Pennington's Assistant

"Am I moving to fast? Would you like to talk for a bit longer?" I asked, holding her hand.

"No. It's alright. I like what you are doing. I'm just a little nervous." Elena replied.

"Why are you nervous?"

"I... I don't do this. I never do this, and I'm not as experienced, as good, as you are used to." She said.

"Look I never do this either, but you're pretty and sweet." I tried to put her at ease.

She cracked a smile. It was understandable. For all she knew, I was a gigolo. The ironic truth was, fingering Pennington aside, I was far from a gigolo.

"Look, I'm not going to judge you. Just relax, enjoy, and let me know if you want to stop." I cupped her face between my palms softly. "Close your eyes, take a deep breath, and let it out slowly."

I guided her back into a chair, and began to rub her neck and shoulders to help her relax and to, hopefully, put her in the mood. "Is this OK?" I asked by gently leaning over and whispering the question in her ear.

"It is fantastic." She replied.

"I don't want to wrinkle your dress, may I unzip it?"

"Yes. Please."

I unzipped the zipper to the bottom until I could see the elastic band of the top of her red panties. I continued to massage her back trying to be gentle but to use acupressure to loosen the muscles beside her spine and around her shoulder blades. I swept her hair over the other shoulder so that it hung down over her chest as I worked on the other side of her neck and back. I ran my fingers in a light claw into her hair and massaged her scalp a little. Only after rubbing her back for some time did I ease the dress over her shoulders so that it fell down in a bunch around her waist. A red silk bra was the sole remaining barrier to toplessness. The bra seemed more a polite convention dutifully followed than a supportive undergarment. Elena was slight and not so well developed in the chest that the bra would be essential. I moved around to the front of the chair.

"How about if we continue the back rub on the bed? It may be a little more comfortable." I took her hands to help her to a standing position. I caught the dress as it fell away and held it so that she could step out of it. "If you lay down on your stomach on the bed, I'll finish what I started."

She complied, and I put her dress over the chair, and then took advantage of the opportunity to shed my clothing down to boxers. I then just rubbed Elena's back. I was not kneading her muscles as I previously had been. I straddled her by kneeling outside of either side of her hips. Her svelte figure accommodated my doing this without putting any weight on her. I leaned down putting my bare chest on her back, which was bare except for the band of the bra strap. "Is everything alright? Do you have any requests?" I again whispered in her ear. My stiff member aligned itself naturally in the dipping cleft in her panties between her butt cheeks. The two shear layers of fabric served to keep things in playful check

"It is great. Please keep going. Thank you." She said.

I massaged her butt cheeks, the backs of her thighs, her calves, and spend a great deal of time on the soles of her feel. As I kneaded the soles of her feet she stifled a moan. Gradually, I worked my way back to my previous position laying over her and I kissed along the back and side of her neck and the tops of her shoulders. After a time, I bid her to turn onto her side, and we kissed for several minutes before I reached around and unhooked the bra.

I had to say, in spite of the torment, being in Pennington's employ had made me a great deal more patient. I often got insanely horny in the mornings during bath time, but could never do anything about it until at least nine o'clock at night. I wasn't allowed to touch myself in Ms. Pennington's presence, and when we got to the office it was all business.

I rolled Elena onto her back and straddled her hips. I continued to kiss her as I cupped one of her tiny mounds in my hand and, with the lightest of touch, began to excite the skin from the outside gradually working toward the areola. I only slowly increased the intensity of this manual stimulation. Elena cooed when I finally placed one of her nipples in my mouth and began to suck it and stimulate it with flicks of my tongue. I caressed her face, and brushed the hair off her face gently as I gave attention to her breasts. I raked my fingertips and nails all over her body to excite the flesh. At one point as I ran my fingers over her thigh and to the inside of her knee, her knees parted wide. It was like a flower blossoming at my touch. I let my forearm glide over the crotch of her panties everso lightly, and when my fingers got there I let them linger. I could feel the moist heat on the other side of the thin layer of silk. Elena arched her hips to press into my hand. Perhaps it was involuntary; so eager was she for relief. I denied her. The night was still young.

I held her wrists lightly above her head and kissed her face, neck, and shoulders. It was my intention to let the tension build a little. I dropped over onto my back, and peeled my boxers off. My erection bounced when it escaped confinement. Elena touched it tentatively and tenderly in a reflexive attempt to return the pleasure she had been receiving. She rubbed a coating of the slick clear pre-cum over the head of my cock, and I eased her hand away. I craved giving her the night of her life, and wanted to take her to a point at which she could no longer bear any alternative other than to be taken passionately. I hooked my fingers into the waistband of her panties and drew them off her. Once again her knees opened invitingly once the panties were down around her ankles. Ironically, given her petite frame, she had about the thickest clitoris I'd ever seen, or so it seemed anyway. I moved down between her legs and sucked the clit into my mouth using pressure with the tip of my tongue to manipulate the sensitive area directly under the hood. She was moaning now, apparently, involuntarily. Her hands moved randomly over her chest and stomach, seemingly more driven by a giddy raw live energy that filled her than by conscious thought about caressing herself.

"Should I stop?" I asked coyly.

With efforts to regain her breath, she replied. "Oh, don't stop. Please, Please, don't stop."

She had so given in to the moment that I gladly complied. Soon her hips began to bounce spastically on the mattress like a basketball being dribbled. I tried to maintain my mouth on her clit, but my face could not keep up with the erratic motions of her orgasmic form. I reveled in her warm sauce as it covered my face. She seemed to have little bodily control. It was a good first orgasm of the night. I didn't know if I could top it, but I intended to try.

After the spasms had subsided into tremors, and the tremors into near complete flaccidity, I lay beside Elena gently tracing along the outline of her breasts with a finger.

"I'm sorry." Elena said.

"For what?" I asked.

"For cumming so soon."

"Don't worry; you don't get off that easily. That was what, in a restaurant, you would call an appetizer." I said.

It was true. After a brief respite during which we sought the warmth under the covers, we were again locked in an embrace.

"You've got quite the sweet little body." She was now straddling me as I lay on my back. I was not inside her, but rather she had just mounted me like a jockey onto a race horse. I complimented Elena as I put my hands around her narrow waist.

"Thanks. You're kind, but I wish I had breasts like Bea's." She said.

This confused me. I ignorantly asked "Do bees have breasts? If so, they must be tiny."

She laughed. "No, Beatrice... Beatrice Pennington."

I guess I was aware that Ms. Pennington's name was Beatrice, but I didn't know anyone who called her Bea. Certainly, I would never have dared such informality, and, hence, I did not make the connection. "You don't need them, you look great without them. And think of the back-aches that lady must get."

"That's true." She said before changing the subject. "Lay back, I want to do something." She then threw off the covers, and then crawled over to the night stand and came back with what I could only assume was one of the aforementioned condoms. She moved back into a position straddling my legs. After installing protection, an action simplified by my extreme turgidity even for her amateurish hands, Elena took my rigid member in her mouth. She started slowly and then her head began to bob with increasing vigor. The warmth of her mouth through the latex was pleasant to say the least. Elena proved surprisingly skilled with her mouth for a woman that had seemed so nervous and tentative earlier. She looked up at me and no doubt saw euphoria personified. It had been months since I'd been with a woman - not counting Pennington, which I didn't for obvious reasons- and, despite my new found discipline, it was only a few minutes before I was in danger of explosively shooting my load. Exercising a level of restraint that I was surprised I could manage, I sat up and extracted my member from Elena's willing mouth. I put some pillows against the headboard, and leaned back against them. I then ushered Elena into a position with her back to my chest sitting between my legs. I put my arms around her and, with one hand massaged one of her pert tits while the other hand draped across her midsection so that I could manually massage her engorged clit. As I did this, I was sucking on the side of her neck and the top of her shoulder.

Perhaps it was becoming an engrained impulse with me to make the process about servicing the woman. Maybe, I would have to thank Pennington for the "training" because I was having a great time.

My chin rested on the top of her shoulder, and I could conveniently whisper in her ear messages that helped to excite and arouse her as well as keeping me engorged. Although with my cock pinned flat against the small of her back, her subtle wriggling also contributed to my continued rigidity. I told her how beautiful I found her and how I longed to be inside her. I could feel her wetness grow, and her heart race faster. She moaned and squirmed in delight.

Finally, she called out in a high-pitched breathless tone. "Oh, please take me, please fuck me." As she did so she leaned forward to extract herself from my embrace. Displaying limberness, she quickly got her knees under herself such that she was on her hands and knees.

I got up to my knees, stroking myself to verify the protection was still soundly positioned. I put my cock between her legs with the front of my pelvis against her buttocks, and then backed it off down her slit until I felt the subtle dip of her vaginal opening. I pushed gently to breach her pussy and took a few slow strokes gradually increasing in depth to get the condom slick with her lubricant. It was a pleasant in a way I cannot adequately put words to. I had never felt a pussy so tight, at least not since I had been a seventeen year old boy with a seventeen year old girl, but those memories were blurred not just by the passage of time since then but also the limited passage of time during the act. After taking long slow strokes for a minute or two I began to get into a faster rhythm. Elena moaned and I frequently found myself having to use every trick in the book to slow myself down. However, I now knew the joy of making things last far more than did the version of me from a decade ago.

I pulled out and eased Elena over onto her back. I re-entered her in the missionary position and resumed vigorous fucking. This allowed us to kiss, and to engage in eye contact. I cupped the side of her neck in my palm as I fucked her. Elena's hips began to tremble and she began to cry out more loudly than before - forgetting to censor her volume to account for the fact that we were in a hotel and a classy one at that. Her orgasmic contractions sent me into a blissful state beyond which I had no capacity to resist or control the geyser-like ejaculation that was checked by the condom. My eruption continued for longer than I had yet ever experienced and involved the release of more of my seed than I thought I was capable of producing. I was almost thankful for the involuntary celibacy of sorts that Pennington had imposed on me.

I fell over to my side next to an Elena who was still regaining her breath. We fell asleep that way with our legs still entangled together. Elena fell asleep first as I was brushing her hair out of her face and then pulling the cover over us. It was about midnight. I thought briefly about whether I should extract myself and leave, but I fell asleep in the deliberation process.

September 3, 2000:

I awoke to see Elena laying on her side on the bed with eyes wide open looking at me. Unlike me, she was on top of the bedspread and fully dressed in jeans and a college sweatshirt. It was definitely morning judging from the light shining in through the balcony door, but the shafts of light did not penetrate so deeply into the room as to shine on us in the bed. We just looked into each other's eyes for a moment.

I broke the silence. "Sorry, I fell asleep."

She then spoke. "Thank you for not leaving."

"Do you mind if I take a shower? But if you're in a hurry I can go." I asked, but then realized I might be imposing and she might need to be somewhere.

"Not at all. I have to be checked out in an hour, and then I've got somewhere to be at 12:00 noon. But you've got plenty of time for a shower." Elena said.

I got out of bed briskly and went into the bathroom half shutting the door behind me. I didn't know what the intimacy protocol was with someone with whom you had just spent the night. It seemed silly to be too uptight about privacy given that we had not only seen each other naked, but engaged in the most intimate of activities. I started the shower and then emptied my bladder.

The shower helped to re-invigorate me. The pounding spray of steaming hot water cleared my head greatly. I came out of the shower in a towel out of force of habit. I found my clothing, and, dropping the towel, put back on my clothing from the night before.

"Well, I guess I should be going so that you can get on about your day. Have a safe trip back to Delaware." I grabbed a piece of paper off the little hotel stationary pad on the desk, and jotted off my cell-phone number. "Here is my number, when you are back in town please let me know."

"Yes, I'd like to do that. I guess as long as you work for Bea, we'll see each other around." I thought I discerned a little tremor in her voice, but didn't want to embarrass either of us by bringing it to the fore.

"Even if I don't still work for her, you can call me." As I was almost in a constant state of ambivalence about continuing to work for Pennington, I didn't want the ability to get to know Elena to hinge on maintaining my present job.

It was then that a tragic moment transpired. It was certainly sad for me, but I couldn't look past my own feelings of the moment. It wasn't until later, when I began to write my thoughts down that night, that I considered the possible influence on Elena. Elena approached and I raised my hands to waist height in anticipation of a hug and a goodbye peck. Instead, Elena put something in one of my outstretched hands. It was a crisp folded $100 bill.

"I know Bea pays you, and she said this was on her, but I thought a tip would be in order." Elena said, not looking up at me but rather down at my feet.

I felt dejected on two levels. On the one hand, the tip was a reminder of how Elena really saw me. This created a hollow lonely feeling. Was the feeling of a deeper connection between us just an illusion on my part? On the other hand, this was my Rubicon. Up until now, I could reason that I was the personal assistant of an extremely peculiar woman. I could even rationalize fingering Pennington as assisting the boss through the application of stress reduction techniques. Once that money hit my pocket, I was officially a whore; though not just a whore, but the kind of whore that gets passed around to her friends.

Later, after I left and was alone, I wondered if it was a sad moment for Elena as well. If one had an instant's thought that one was developing a personal intimate connection with another person, then believing you were just a commercial transaction for the other person would be a demoralizing proposition. If I had been certain that she felt that way, I would have handed her the bill back and told her that I would gladly and freely spend evenings like that with her, and that, beyond that, I wanted to know who she was as a person. As I teetered on the brink of doing just that, I thought about the possibility of a rejection more personally humiliating than anything Pennington could put me through. Another part of me said: "Hey, maybe you are just a man-whore to her. Maybe she was just looking for a physical release with no strings attached. Despite the lack of a ring, maybe she was married with two kids, and was just making up for an inadequate home sex life." Given the limits of my self-esteem, caution reined over courage, and I put the bill in my pocket, said thanks, turned, and left briskly. It is amazing how quickly one's confidence can crumble under changing conditions.

I got a call at 12:30 in the afternoon from Juanita. She said that Pennington was insisting I come in as soon as possible. While part of me bemoaned the loss of the rest of my weekend, part was glad for a distraction from the lonely wake from the previous night.

I arrived at about 1:00pm, but by the time I had stripped, stowed my clothing, and crossed through the house it was 1:10pm as I entered Ms. Pennington's bed chamber. The sight I saw upon entering the room stole my breath. Pennington was lying on her back with her knees bent and spread, and Elena was on hands and elbows between my employer's legs sucking her off.

Pennington looked over and motioned me to her side with a brisk wave of the hand. I had not even realized that I came to a complete stop. Elena looked up and seemed caught off guard when she saw me naked but for the livestock collar. Her moment of shock was cut short when Pennington sat up, put her hand on the back of Elena's neck, and pulled my previous evenings date's face back into her crotch. As I got to the edge of the bed, Pennington cupped the breast closest to me and lifted the heavy orb toward me. This was enough of an indication to know that I was supposed to do something with it. I lay on my side on the edge of the bed, and popped the nipple into my mouth. In the corner of my eye I saw motion. Without breaking suction, I looked over with a subtle head turn and eye movement to see Juanita, in her maid uniform, following the action with a small hand-held video camera. I had no idea from Juanita's blank stare if she was disgusted, aroused, or indifferent.

As both Elena's mouth and mine were occupied, Pennington did the talking. "Elena came over and was telling me what a good night she had with you last night. I had Juanita call you over because I wanted to see it for myself. It's quite a thrilling prospect to get my two best bitches together at one time. I wonder if Elena told you that she gave herself to me when we were roommates in that god-awful women's college. I always preferred the men, you know, but necessity can be the mother of bisexuality. Elena was my first. If you think she is shy now, she was as timid and skittish as a baby bunny back then. Her loneliness made her extremely willing to please. I think the two of you have that in common. I'll say this though, she learned to suck a mean pussy." Pennington's speech transmogrified into moans and cries as she submitted the pleasure.

I switched the tit I was servicing with my mouth and used my hand to stimulate the nipple of the first breast I had pleasured while beginning to suck on the other one. It was odd hearing Pennington speak about Elena as she spoke about me, which was in pet-like terms.