The Playful Babysitter Read online

  Alas, things don’t always go according to plan. I guess they’re called bankers’ hours for a reason as, once again, Liz was not in the office.

  I’d first noticed Liz – or more precisely, her legs and footwear – during a prior visit. She was heading out of the branch as I was going in, and I held the door for her. She wore a Fleet Bank lapel pin on her smartly tailored suit. As is my custom, I glanced downward, and was rewarded with a gorgeous pair of legs in nude hose, and a beautiful pair of multi-colored, three-inch heel pumps. We exchanged a courteous hello. It was a “fleeting” moment, but it stuck in my head.

  I found her name listed under Branch Manager on a sign in the bank’s lobby, and instantly committed it to memory. Liz was about 38, with dark, shoulder length hair, very modest make-up except for around the eyes, where she used a lot, and a finely shaped body, which I later found was almost always accented by fitted suits, pencil skirts, or pleated skirts. Once in awhile she wore a pantsuit. She wasn’t what I’d call gorgeous, but was…sultry, with a seasoned, world-wise look in her eyes. There was also a slight raspiness in her voice, which added to her overall sex appeal.

  But obviously, it was her finely sculpted stems that were her most memorable part, and her terrific taste in fashionable shoes. Although I’d missed her on this day, I soon began talking to her, asking for help with some banking issue or another, even inviting her to various business groups I was involved in – all in a ploy to soak in whatever she happened to be sheathing her legs and feet in that day. She was always pleasant, befitting her customer service role, as my attention drifted between her eyes and her feet. Sometimes she wore scalloped black pumps, or green or maroon snake skins. Often they were a palette of colors, or had sequins, as if she was going out straight from work. They all had three-inch spikes, and delightfully, many revealed a good helping of toe cleavage.

  Quickly enough, Liz began to populate my masturbatory fantasies. She’d catch me staring at her feet, putting me on the spot before taking pity and letting me kiss or lick them, laughing as I did so. I thought about how nice they’d look up close, how aromatic they’d smell, especially at the end of a long day.

  One day, after our friendship had developed a bit, she invited me out to lunch, to thank me for keeping her in the loop about local business events, and to talk about our respective jobs. She was married, and I was recently divorced. We dined at a little Italian restaurant she picked. She wore sheer black hose with patent black pumps and toe cleavage on display. Sadly, frustratingly, my angle and the table cloth didn’t allow me any opportunity to enjoy her display.

  While eating lunch, I finally got up the courage to share, discretely, some of my thoughts.

  “I have to confess something,” I began. “I had been noticing you for awhile when I came into the bank, particularly your great taste in shoes.”

  It wasn’t completely inappropriate. After all, as a long-time foot fetishist, I’d learned that most women are very flattered, even impressed, when a man compliments their footwear. She smiled, and muttered something about how she loves shoes.

  “Well, yours are always very nice,” I said. “And your legs show them off to great effect.” That launched into a conversation about where she shops for her shoes, the size of her collection, etc. I was maintaining a professional, conversational facade, but I was really thinking about worshipping her from the tips of her toes to the inside of her thighs. My fetish was out there now; from then on there’d be no doubt in her mind what I liked.

  A few months later, Liz left the bank for a competitor in the same town, and although I wasn’t a customer, I’d continue seeing her at the occasional business function, or stop in the branch when I was “passing by” to say hello. Once or twice when we’d be talking at the branch office, she’d begin slipping her foot in and out of her shoe, a subtle, amused smirk on her face. Her scarcity in my life didn’t mean she was less a part of my fantasies.

  One day when I stopped by the branch, I learned that she’d left the company and returned to Fleet Bank, managing a different branch that was about five miles from my home. This wasn’t a branch I’d ever banked in, because there were several closer ones, but I did drive past it from time to time. Upon learning she worked there, I stopped in to say hi.

  She was wearing a smart blue suit with skirt, nude hose, and navy pumps. She was in an informal, end-of-day meeting with her assistant manager, who she introduced as Lauren, and one of her service representatives, Betsy. Lauren, around 28, had a cute, slightly pudgy face, dark hair and pleasant smile. Of course, what I noticed was her attractive legs and open-toe black high heels. Betsy was about 32 and heavy-set but with a pleasant face and nicely dressed, with pants and black ballet flats.

  “Gray’s a great guy. He knows everybody,” Liz said, evoking polite smiles from her colleagues.

  We made a bit of small talk, she told me why she decided to return to Fleet, and after a few more moments of mostly staring at her legs, I said I’d leave them to finish their closing routine.

  “Oh, nonsense. Why don’t you hang out for a little while? We have to be here for another hour anyway.”

  The branch had emptied, the tellers gone. Only the drive-thru tellers in another part of the store remained. I suddenly became aware of the perfume one of them was wearing, but I couldn’t tell for sure whose it was.

  We continued to make small talk for a few minutes. Suddenly, Liz smiled and said, “What do you think of Lauren’s shoes, Gray?”

  The comment caught me off-guard. “They’re nice,” I said, trying to sound nonplussed.

  “Aww, just ‘nice’?” Liz prodded, as she uncrossed then re-crossed her stockinged legs.

  I became fixated on those legs, and felt a knot form in my lower abdomen, a not-unpleasant feeling that I get when I find myself becoming embarrassed.

  “Uhhh…”

  Then, by way of explanation, “Gray is a connoisseur of women’s shoes. He says I have good taste.” A gleeful laugh followed.

  “Well I have good taste too, don’t I?” said Lauren.

  “Uh….sure you do,” I said innocently. “Open toe pumps are very nice…they complement your legs well.”

  “He is sweet, Liz,” Lauren affirmed, without taking her eyes off of my face.

  “Take them off, Lauren,” Liz instructed. She slowly slipped her right shoe off her heel, and momentarily dangled it from her toes before letting it drop to the floor.

  “And her feet, Gray? Do you like her feet too?”

  Oh god, I’ve been exposed as the foot lover I am. This was going from bad to worse. The tingling that I’d felt in my groin was supplanted by my inflating cock. Without being offered a seat, I could only shift my own feet and hope the fall of my khakis wouldn’t make the bulge obvious.

  “Um, yes, Lauren…I do,” I stammered. Delighted, Lauren wiggled her toes.

  “Wow, it’s really nice to hear that from a guy,” she said. “I’m so self conscious about my feet.”

  I couldn’t turn my eyes away from Lauren’s flexing toes…until my peripheral vision caught Liz’s manicured hand slowly pulling off her left pump. I’d known Liz for about a year, but I’d never seen her foot completely nude before, only fantasized about it while jerking. The thought that this Holy Grail was about to be revealed caused a full-fledged hard-on, which no one would be able to miss. I looked unabashedly down at her foot, a bead of sweat forming on my brow. Liz paused, then slipped the shoe back on, a sly grin forming on her mouth.

  “And Betsy’s. What do you think of Betsy’s feet?”

  On cue, Betsy wiggled her thick toes out of her black flats. Pale and unmanicured, they weren’t exactly my thing. I hesitated.

  “Uhh…they’re nice,” I said politely.

  “They are, aren’t they?” Liz replied, smiling at Betsy. “You know, I think you should get up close and tell them personally.”

  A knot formed in my stomach. That pleasant tingling of embarrassment was being replaced by a nauseous feeling of hum
iliation. “Umm…I…don’t…”

  Liz knew the power she wielded over me. Maybe it was stupid to tell her of my attraction to her legs and shoes. Now she was using that information to – what? – test me? Or was she just getting a thrill out of this? “Get down, Gray.”

  My free will no longer free, I sank to my knees, my face just inches from Betsy’s dogs. “Tell them,” Liz repeated.

  “Umm…your feet are very nice, Betsy,” I managed.

  “No, Gray, tell THEM,” Liz smiled up at Lauren as she said it.

  I sighed deeply. “You are very nice feet,” I said, feeling ridiculous, and not meaning a word of it. All three women giggled, none louder than Betsy herself.

  “Hmmm…I don’t think he means it,” said Betsy.

  “Gray, kiss them to show them you mean it,” Liz instructed.

  My cheeks flushed, and I felt lightheaded. Betsy’s toes wiggled in front of my face. Would there be a reward for this ordeal, I wondered?

  Slowly, and obviously reluctantly, I leaned in and kissed the tops of both of Betsy’s feet. Their smell was not unpleasant. Although the humiliation was intense, and despite finding Betsy’s feet rather unappealing, I felt my penis betraying these feelings. I found it an incredible turn on to be ordered into this submissive position by my “friend” Liz, and it didn’t go unnoticed, as I heard more laughter.

  Liz’s manicured hand reached again for her right pump.

  “Betsy’s feet are pretty, but these…these are the feet you’re really interested in, aren’t they?” Liz cooed in that raspy voice, as she began to remove the shoe. “Hmmm?”

  More sweat formed on my forehead.

  “Come over for a closer look.”

  My head swam. My body was on autopilot as I shuffled in front of her. By the time I stopped moving, she was cradling her navy pump in her right hand. There were more giggles, but they barely registered in my brain.

  My eyes were focused on her glorious right foot. It was as lovely as I’d imagined it, with perfectly painted, dark red toenails showing through her gossamer hosiery. A little toe wiggle sent a shiver up my spine.

  The view was short-lived as Liz brought the shoe to my face. Oh my god, oh my god, ohmygod, I thought. Her left hand reached around the back of my head, and pulled it tight against the pump, the toe area directly over my nose. She knew it’s what I wanted, what I was longing for, and that resistance was futile.

  “Breathe deeply,” she purred.

  For all intents and purposes, Lauren was no longer in the office, and Betsy, well, she might as well not have been born for all the attention I paid to her. My world came down to the inside of Liz’s pump.

  I swooned, and my penis swelled.

  “Oh my, you’re really enjoying this, aren’t you? That is too funny!”

  I couldn’t answer, as my nose and mouth were enveloped by the lovely scent of her foot, sweat mixed with well-worn leather.

  “Do you like the way my shoe smells?” I could only groan. My eyes locked on her face. She pursed her lips sexily and arched an eyebrow, smug in the knowledge that I did.

  “If you like that, you’re really going to like this…”

  I felt her left foot snake its way onto the bulge in my pants. As much as this scenario was fueling my hard on, I didn’t anticipate this development, nor did I really want to lose it in front of three bank employees, not to mention two others working the drive-through 40 feet away. Who were they? I briefly wondered. Were they also females? And how soon would their shift be ending?

  Still on my knees, I began to push my groin forward, basically humping that delightful foot. Paradoxically, I sought more pressure, even as I dreaded the inevitable outcome of getting it. Yet the scent working its way into my brain goaded me on. A moan escaped.

  “Awww…you’re going to mess your pants right here in the bank, aren’t you? Well, there’s probably nothing you can do about it now, so you may as well just enjoy it.” With that, Liz planted her right foot on top of my cotton-covered ball sack, and pressed forcefully. At the same time, she threw her hair back out of her eyes and laughed.

  “I like you, Gray, I’m doing this for you. I knew ever since we had lunch how much this would mean to you.”

  Yes, it means everything to me, my mind screamed silently. I heard more chuckling, as Liz’s foot continued its sweet assault on my grateful erection.

  Whatever dignity I had left escaped me at that moment, what with a manicured feminine hand controlling two of my senses, my hips oscillating of their own volition to build up pressure against my aching penis, and three women looking on with a mixture of approval and mischievousness.

  “Oh, look what time it is!” Lauren cried out. “The drive-through is closing now.” Then, in a reproaching tone of voice she said, “You might want to hurry up, Gray…surely you don’t want to spurt in front of five women, do you?”

  My penis quivered, which unfortunately didn’t go unnoticed by Liz’s silken toes.

  “Hmmm…judging from his reaction, he does. Could that be your true wish, Gray? Hmmm?”

  I shook my head No to the extent Liz’s sexy pump would allow. My embarrassment fueled my lust, and incredibly, my hard-on grew just a bit more.

  Sensing this, Liz slowed her foot movement. I was close to shooting a large load, but this backed me off just enough to prolong the humiliating torment.

  “Please, Liz…” I groaned through the shoe.

  “Please what, Gray?”

  “Let me finish…”

  “In a minute…I want you to hold it,” she chuckled.

  Despite her command, my hips moved more emphatically. At that moment I heard more voices.

  “Liz, here are the drive-through drawers, we’re outta…oh my god!”

  Then, in as stern a voice I’ve ever heard from Liz: “Go for it, Gray.”

  The traffic light turned to full-on green, and my hips moved a notch faster.

  Though I couldn’t see the drive-thru employees at all, though it was incredibly debasing, and in spite of my fear of never being looked at the same way again by five bankers, I was primed to launch a load that would momentarily spread across the front of my khakis.

  “Ohhhhh…..” I grunted, my body shaking, my hips thrusting. Girlish laughing mingled with Liz’s shoe scent worked to overwhelm my brain cells.

  “Now, Betsy, now!” commanded Liz, pulling her pump away at the last moment.

  With laughter, Betsy rammed her pale foot past my lips. What the ---? I thought. My eyes still focused on Liz’s wiggling toes, but it was Betsy’s feet I would smell and taste, that I would forever associate with the moment of my release. What an awful turn of events! Why was Liz being so cruel as to deprive me of the heavenly scent of her shoe, and the feel of that broken-in leather against my face, at the moment of truth?

  As my back arched and my body quivered, as shot after shot of sperm flew up against the inside of my pants, I received the answer to my unasked question, as though Liz could read my mind.

  “You should’ve been nicer to Betsy’s feet, Gray,” she sang, to a humiliating chorus of laughter.

  Table of Contents

  The Adjunct Professor

  The Playful Babysitter

  Model Humiliation

  The Playful Babysitter Returns

  Foot Worship Scrabble

  A Matter of Discrimination

  Fleet Feet