The Right Side of the Hill

(c) 2005 by Penelope Street

There it was again. For the fourth consecutive week the same ad had appeared in the personals section of

The Scene

, a local rag dedicated to the seedier edge of society. I routinely perused the personals. Once in a while, I stumbled upon an arousing one. Most often though, I found the racy little blurbs amusing instead of exciting.

I had initially thought the same of this one:

~~~

SWF, 53

Looking for a master. I would like to be a slave. A sex slave. I expect to be disciplined if I do not please my master.

~~~

That was the first week. The next week it was still there, but had moved down as the newer ads appeared above it. By then, it wasn't really funny anymore. Like most men, I suppose, the idea of having a slave girl as a sexual toy had its appeal. But I still shook my head; convinced that sometime well before fifty women ceased being sensual and turned into old ladies.

When the third week arrived, I even considered not picking up the free publication. The thought that the poor woman was out there, being ignored by everyone, had begun to trouble me. And that it troubled me, well, that troubled me even more.

I hoped I wouldn't see the ad the fourth week, but it was there anyway, at the bottom of the list. It was far from funny at that point.

My eyes dropped as these thoughts crossed my mind. I felt guilty for judging this anonymous person so, but I couldn't shake the vision from my head: a grey-haired woman on her knees in a collar, looking more like a pallid raisin than an object of desire.

I brought my index finger to my right ear, scouring the furrows of more grime than I expected to encounter.

What does she really look like?

I wondered.

And why does it matter?

I snorted my amusement, realizing no man had ever found an answer to that latter question, and none ever would. But the first question, it had an answer. Somewhere. Yes, I mused with a nod.

What an interesting question. She's old enough to be your mother. What makes her think she's still got it?

In spite of my giving the issue due consideration, it was still a question without an answer as my day ended. Nothing had changed in that regard when I arose the next morning. Wiping the sleep from my eyes, I decided the poor old woman deserved at least one response for her troubles. I wandered to my computer and created a new e-mail address. Five minutes later I was back on my bed, phone in my shaking hand, dialing the toll number on the back of the rag.

I flipped back through the pages of the publication rapidly as the line rang, searching for the ad. I need not have hurried, there was a slow voice and a list of options- just to drive the price up, I'm sure. Several minutes later at two bucks per, I finally reached the woman's messaging inbox.

"Hi. I'm Benjamin. I'm interested in seeing you. And, uh, learning more about you. You can e-mail me at swf53lover at hotmail dot com. Look forward to hearing from you. Bye."

Slamming the receiver down, I wondered if that was the worst ten dollars I had ever spent. Then I considered the concession prices at any major sporting event and decided it couldn't possibly be.

As the day passed, I caught myself checking my dedicated e-mail address so often I lost track of the number of times. The sun had long departed and a good portion of my hope with it when my heart skipped a beat, maybe two; my inbox was no longer empty!

I passed a large breath before I moved my quivering fingers to my mouse and opened the message.

~~~

Dear SWF53Lover,

What a clever name. I'm flattered. You've already scored more points than the rest of the applicants combined. But what makes you think yourself worthy to be my master?

Yours, *maybe*,

SWF 53

~~~

I glanced to the reply address and smiled:

swf53@hotmail.com

. Over the next several hours, I read the brief message over and over again, trying with each pass to pluck new information from the words. The confident, almost cocky, reply was not at all what I had anticipated from an aspiring submissive.

Pacing trails in the carpet of my apartment, I mulled over the possible replies.

What makes me think I'm worthy? How dare you take that tone with me, you worthless slut! You'll be lucky...

No, I decided, shaking my head.

She doesn't need luck. She has lots of interest. Lots more than I imagined. That won't do. No. Something else, but what? Dearest Lady, Here are my list of qualifications...

A half-snort, half-chortle terminated that overly pretentious option. I leaned back in my chair and brought my index finger to graze my lower lip. With a smile I surged forward. A second later my fingers were bouncing along the keyboard:

~~~

Dear SWF53,

I have what you want.

Benjamin

~~~

With a smile I proofread the single sentence, pressed the 'send' button, and then went to bed. Nine and a half hours of sound sleep later I awoke to find the reply waiting:

~~~

Dear Ben,

Do you have what I want? Perhaps we should find out. Can you be at Martin's Cafe tomorrow, say 6:30? Tell the hostess you are there to meet Alexandra.

Alex

~~~

I leaned back in my chair, sighed, and read the message again. Who was this alleged submissive that saw fit to question my worthiness and then give me directions? I decided whoever she was; she must be a very interesting woman indeed. I wanted to know more. Had she ever been married? If not, why not? If so, what had happened? Did she have children? Did her marriage fail due to this bondage fetish?

My eyes narrowed.

Or does she seek a slave?

My head began to move in a slow nod as I pondered the likelihood.

Am I being reeled in here like some pathetic trout after a shiny new lure? Or, in this case, perhaps a shiny old lure?

I knew there was only one way to find out; and I would find out, if nothing else. I looked again to the message still upon my computer screen.

Martin's Cafe?

I clamped my lips tight as my head moved in a shallow but steady bob.

Pretty ritzy place. Bet she expects me to pay. This better not be some old broad's clever scheme to get a free dinner date.

* * *

Regardless of the possibilities of failure, and embarrassment, the appointed hour found me at the hostess's podium of Martin's.

"I'm here to meet someone; her name is Alexandra."

"Would you be Benjamin?"

I started to say, "Yes," but found my mouth dry. I swallowed and nodded instead.

The young lady smiled. "Right this way, sir." She turned and led me into a side room, along the row of booths adjacent to the wall until she reached the last such enclosure.

"Here you go, sir."

I inhaled a sharp gasp as I beheld the siren that awaited me. She was anything but what I expected: young, maybe thirty; lovely raven colored tresses flowing straight onto a crimson dress that she filled to perfection. The black of her hair and the emerald of her eyes contrasted with the pallor of her flesh in the most captivating and classy of fashions.

Could the ad possibly have read 5'3 instead of 53?

I wondered, searching my memory.

Yes, that would be about the right height. Still, this can't be her? She's too pretty. Or maybe she really is looking for a slave. Wow. I could be that! Yes, I could lick her pussy, her foot, whatever. Hell, I could lick her anywhere, if that's what she...

"Ben?"

I shuddered as I snapped from my stupor. "Yes. Alexandra?"

The brunette smiled. "Call me Alex."

"I'm sorry," I offered. "I didn't mean to stare. It's just I was expecting someone..."

"Older?"

My head moved in a brisk nod. "Yes. Not that I'm disappointed!"

"Not yet anyway." The woman laughed through a smile and motioned across the table. "Do have a seat."

How could I ever be disappointed in you?

I wondered, sliding into the booth.

Alexandra leaned across the table, asking in a soft, clear voice, "So you are in the market for a slave?"

"Yes," I nodded, scarcely willing to believe such a goddess would be interested in serving an admittedly average guy like myself.

"I'm here on behalf of my mother," the woman continued.

In that instant it was as though the pressure in the room had been halved, sucking the air from my lungs. I tongued my lips and tried not to appear shocked, to little avail.

"Disappointed yet?"

I moved my head in a brisk, if dishonest, shake. "No."

Alex smiled. "Good. Mother asked me to meet all her prospective masters and choose one for her. She doesn't believe it would be a proper start to the relationship if she were to have any say in who her new master is."

"I see." I nodded, admitting even to myself there was some twisted logic to the woman's words. Still, in the back of my mind, I refused to surrender all hope that the mother angle might be just a ruse.

"Can I get you a drink, sir?"

I jumped, snapping my gaze to the waitress that had appeared from nowhere. "Uh, yes, please," I stammered. "Tea will be fine, thank you."

"I'll be right back with that and to take your order," the young lady declared before she turned to depart.

Alexandra winked at me as I looked back across the table. "

Please

and

Thank you?

Not what I expected from an aspiring master."

My gaze wavered. My lips formed a circular channel for my extended exhale as I considered what might be the best response. "Yes," I said after a few seconds, "but then the waitress isn't my slave, is she?"

Alex flashed a quick smile. "No, she isn't." With that, she flipped open a small, well-worn, notepad. "Now let's get down to business, shall we?"

I felt my throat flex, passing another dry swallow. "Yes, let's."

The brunette's smile was gone as she looked up from her notes. "Do you expect my mother to live with you as a full time slave?"

My eyes wandered for a moment or two before I nodded "Yes, I suppose a slave should live with her master." I tried not to laugh as I considered how truly ludicrous my words sounded.

"And what would be her duties?"

"Why, whatever I had in mind, of course." I smiled at what I thought was a clever answer for all of the half-second it took me to notice my companion's expression was unchanged.

"Such as?"

I tilted my head to the right before responding, "You know, cleaning, cooking..."

"What about sex?"

I had only anticipated meeting an older woman, satisfying my curiosity and wishing her the best in her search for, well, for what ever she was seeking. My mouth fell as I grasped the woman intended this meeting to be an interview of sorts, and a prying one at that. Still, this was not the first time I had been forced to think on my feet when tossed a proverbial curve.

"Yes, that too," I affirmed with a nod.

Alex's laser-like green orbs remained steady as she tilted the head that contained them. I felt as those she was somehow peering into my very soul. "Her duties must include sex."

"The ad did mention that," I noted with some haste.

"I want to be clear. It is a non-negotiable issue. She is to be

more

than a maid. And I'm not talking once per month. You must use her sexually at least once daily."

"I see." My head move in a far shallower, slower nod, wondering if the mother might be so hideous that no one wanted her. Looking across at her daughter, that seemed most unlikely.

But that's only if Alex is her daughter

, I reminded myself.

"Very good," Alexandra continued. "Now, can you tell me..." She stopped and looked abruptly away from me as the waitress returned. "We'd like two filets, medium-rare. Fresh vegetables and the soup of the day, please."

The waitress gave a curt nod. "Very good, ma'am. Anything else?"

"No." Alex snapped her focus back as our server departed. "Where were we? Oh, yes; elaborate please on exactly what sexual duties you envision my mother performing."

I tongued my lips. My common sense begged me to simply withdraw my alleged interest. The rest of me, however, was more intrigued than ever. "Well, that would, uh, depend...

"Pretend time stops," Alex interjected, "for everyone but me and you. The entire world is in some sort of stasis and I'm your slave for the next half-hour. I'll do whatever you want. Even I won't remember it. What would you have me do?"

"Right now?" I queried.

"Right now."

This question was even more vexing. Did she really expect me to tell her the truth? I hoped she did. "Blowjob," I said. "While I eat my steak."

"Your steak isn't here yet."

"You know what I mean."

"I suppose I do," Alex agreed. "Do I have to swallow?"

I tongued my lips, hoping this was anything but a hypothetical quiz. "Sure."

"So mother will have to as well?"

I shifted in my seat, trying to adjust in an inconspicuous manner the physical manifestations of my growing interest. "Yes, of course."

"How often?"

"Most every day. Probably twice even."

"Excellent," Alex hissed through a smile. "That would take care of the once per day sex requirement?"

"I suppose."

"Will you ever fuck her normally?"

"Yes."

"Will you expect her to clean your cock for you after you fill her pussy?"

My eyebrows leapt into my forehead as I leaned an inch or two closer to my companion. "What, uh, you mean, well, with her mouth?"

"Of course."

My eyes dropped a few degrees to the ruby lips that managed to verbalize such base inquiries in the most matter-of-fact tones. I could feel the force of my own heartbeat as my eyes lingered on my companion's mouth. "I hadn't thought about that, but now that you've brought it up, the idea does have its appeal."

"What about anal sex?"

"Excuse me?" I snapped. It was but a reflex; she had spoken clearly enough.

"Are you going to butt-fuck her too?"

I snapped my head over my shoulder, wondering who might be in the next booth and how far my companion's voice could carry. Settling back into my seat and directing my attention again across the table, I considered the woman's question.

Would I? I've always been curious. If she's really my slave, why wouldn't I?

I sent a single massive exhale through my pursed lips before I replied, "Yes. I would do that. At least once, just to see if I like it."

Alex's eyebrows bounced upward. "If? So you haven't done this before?"

"No." I admitted with a quick shake of my head.

"Good. Neither has she. What about ass to mouth?"

"What?" I gasped.

"Will you expect mother to suck your cock straight from her ass, or clean it afterward, like you said you would after you fucked her pussy?"

I dropped my brow and shifted in my seat, the flesh of my nose twisting in disgust as I recoiled. "No," I concluded, my head pivoting in a trio of brisk shivers. "That's just- well, wrong."

For the first time since our greeting, the corners of Alex's mouth floated upward, but just. "Does the same go for watersports?"

"You mean, uh, urination?"

"That's right," Alex said. "Pissing. On her. Or in her. Is that part of her duties?"

"No."

"Rimming?"

"What?"

"Does she have to lick your asshole?"

My spine stiffened. "No!"

Alexandra leaned across the table. "Just so we are clear," she began in a stern whisper, "you are correct; none of that is sex so far as my mother is concerned. I haven't even asked her about that sort of sick shit and I never will. I already know it's too far; she'd never enjoy that. She wants to be a concubine, not a fucking toilet. You even try any of that perverted crap on her and I'll see you find out what it's like to be a shit-siphoning sissy slave. That's a promise, young man."

I shivered, even though I did not fully understand the full meaning of the threat. I was rather certain I really didn't want to. "Worry not," I assured. "We are of a mind on this matter."

"Good. Will you make her have sex with other men?"

I paused to consider the issue, my eyes wandering as I deliberated. "I hadn't thought about it," I admitted several seconds later. "Is that also not allowed?"

"I don't think she would mind. She might even be flattered. However, you would be responsible for her safety. That includes safe sex."

"I see." My head began to bob. "I really don't see myself renting her out or anything."

"Whatever you do, you will be responsible for

all

aspects of her safety. If something happens to her, something worse is happening to you. Are we clear?"

"Sure. We're clear."

Alexandra withdrew to her normal sitting position and wiggled her shoulders. Her dress dropped a bit and my eyes followed its descent as another fraction of an inch of cleavage sprang into view. "Tell me about yourself," she demanded.

My eyes snapped back to her face. "Well," I began, shifting again in my seat. "I'm Ben..."

Alex stiffened, then held aloft her index finger. I followed her gaze to the waitress arriving with our soup. As soon as the help was gone, my companion stared back at me. "Ok. Go on."

"I'm Benjamin Miller, attorney. I'm twenty-four, I grad..."

"A lawyer?"

"Yes."

"Is that not a fairly stable profession?"

"I suppose. Why?"

"You're so much younger than anyone else that has responded. What does a young lawyer want with a fifty year old slave?"

I chewed my lower lips as I asked myself the same question. "Entry level lawyers put in tons of hours. I don't have time for anything resembling a real relationship."

"That's it? Convenience?"

"Well, If she looks anything like you, what young lawyer wouldn't want her?"

I hoped the implied compliment would draw at least a grin, but Alex's expression was unchanged. "So it's about appearance and convenience?"

I closed my eyes and counted to three before I responded. "I'm not sure what it's about," I confessed, forcing my eyes to hers. "I've asked myself the same question and I can't say what it is about this situation I find so intriguing."

To my surprise, Alex flashed the slightest of grins. "Do you like being a lawyer?"

I shook my head. "Not really."

"Then why'd you become one?"

"Oh," I began with a shrug, "I always loved courtroom dramas. I had this grand vision of myself saving innocent men from the gallows and the like. It didn't turn out that way, and I doubt it ever will."

"What makes you say that?"

I dropped my brow as I considered how much I should share. "When you're looking for work there are too many lawyers, but as soon as you land a position, there aren't enough. So I work fifty to sixty hours a week, yet I don't know that I could find a better position even if I have time to look for one.

"Still, You think I'd be doing some good, right? But I work for a firm that defends corporations in workman's compensation cases. So guess what I spend my precious time doing? Combing volumes of legal gibberish seeking loopholes so that huge companies don't have to fork over the money some poor bastard needs.

"That might not be so bad if we were specifically trying to avoid paying the fraudulent claims, but we fight them all, tooth and nail. It's not about justice; it's about money. I guess that's the way the alleged legal system has always worked. I just didn't realize it until I was part of it."

"So why are you part of it?" Alex queried.

"Because I've four years of college and a debt to go with it."

Alex nodded. "How much debt?"

I cocked my head. "About 40K."

"Forty thousand?" Alexandra gasped. "Where did you go to school?"

"Mitchell Hawthorne."

The brunette pursed her lips. Her brow leapt upward. "Oh. Very prestigious. I'm impressed. Your family is rich then?"

"Hardly, or I wouldn't have such a debt."

"So you're rather stuck?"

"Yeah," I grunted. "I've pretty much screwed myself. I think I'd have been happier delivering pizzas. Hell, come to think of it, I was"

Alex nodded. "I see. Speaking of screwed, you mentioned you haven't had anal sex. Surely you're not still a virgin?"