The Playful Babysitter Page 3

As luck would have it, I was due for a haircut.

  Scheduling the appointment was surprisingly easy; I’d have guessed that her calendar would be booked for months, but as her victory issue hadn’t yet hit the stands, that wasn’t the case. The hard part was mustering the nerve to sit nonchalantly while this young vixen snipped at my hair, all the while covertly tracking her movements in the mirror. I made the appointment for a Friday night right after work, not sure exactly what I hoped would happen.

  You see, I’m a married man. Thirty-eight years old and in reasonable shape, but with the onset of a bulging gut and early stages of male pattern baldness. A freelance writer by trade, I support a comfortable lifestyle for my family but am far from rich. Beautiful women like Ashley Blake typically had no reason to pay attention to men like me. Unless, that is, we came in as a paying customer.

  When Friday came, I decided to play it cool. No doubt she had a great many clients come in to meet Miss Loaded, but I wouldn’t be one of them. I’d play the part of the casual guy who just needed a stylish cut, and who’d heard something, somewhere, but beyond that would let her decide what, if anything, to say on the subject.

  The sight that greeted me when I walked in the salon quickly emblazoned itself on my brain. Having studied the newspaper photo and another online, the mere act of walking into Ashley Blake’s day-to-day terrain was akin to running into a long-admired celebrity. Here she was, in the living flesh! It was like bumping into Miss America in the frozen food section of the grocery store. You can’t fully prepare for that.

  Ashley was decked out in skin-tight black pants, black spike heeled boots and a glittery, sleeveless top that would delightfully display her underarms every time she reached over my head. Her blond tresses were in a tight pony tail, and she wore a beret-like cap. Clearly, she had plans immediately after work, perhaps with some guy.

  We quickly dispensed with greetings and talked about my hair. I told her to style it however she thought it would look good. Hey, how could I go wrong with a Perfect Ten choosing my hairstyle?

  As she set about first washing – a sublime experience in itself – then actually cutting, I noticed the magazine photos of herself taped up at her workstation. The images were from the current issue, in which she was named a finalist. This girl certainly wasn’t shy.

  “Hey, how’d you make out in that magazine contest? It was Endurance, wasn’t it?” I feigned ignorance.

  She smiled demurely. I thought I caught a bit of modesty. “It was Loaded, actually...and, well, I won.”

  I congratulated her sincerely, and we continued talking about her new obligations, lifestyle, and what she hoped to do now that her modeling career got this very public boost.

  All the while, she maneuvered over and around my head. Despite my best efforts, the combination of her beauty, revealed underarms and perfume – not to mention her two rather attractive co-workers – had me becoming erect. I could only hope the smock would hide the bulge, but a glance down indicated I’d have no such luck. She paused to say something to one of her co-workers. I couldn’t hear anything she said, but their tittering was clearly audible. I had no doubt she was sharing her observation with her sexy haircutting partner.

  She cleared her throat, and got back to work on my hair. I sat up straighter in the chair, trying to affect a dignified posture.

  “Ashley, I’m a freelance writer, and I think you’d make a terrific subject for an article in a local magazine,” I said, fishing out my business card. “Why don’t you give it some thought?”

  She finished me up and gave me her card, accompanied by a coy smile. “Yeah, that sounds good. Call me and we’ll talk.”

  Had it really been that simple? An invitation to call from a woman that hundreds of thousands of men would be drooling over in a few weeks. I virtually bounced out of the salon, without even thinking to scrutinize my new haircut.

  Three days later, I called. I told her I prefer to conduct interviews in person. So that she’d feel “at home,” I suggested we meet Saturday night at a restaurant/bar at a nearby mall that she frequented. She agreed. Truthfully, I was stunned – and delighted – that Miss Loaded had nothing to do on a Saturday night after work. Little did I know she did, in fact, have plans, and I’d soon find out they were contingent on me.

  We met at the appointed time, me waiting for her at the bar. Every male head in the place turned as she strutted in. She was dressed in tight black pants that stopped just above her ankles, a fuzzy pink sweater, and three-inch black heels with ankle straps. Her hair was in a tight ponytail. I called out to her, and felt like a million bucks as she sidled up on the barstool next to me. The other men in the joint must have been wondering who the heck I was.

  After pleasantries, I whipped out a notepad and began asking her questions, keeping up the appearance of an interview – I really was planning to write a story – while trying hard not to stare at her breasts, which were stretching the fabric of the sweater. The bartender recognized her from the magazine, and said he’d voted for her.

  After 45 minutes of chat at the bar, we were seated for dinner. I had a chicken entrée; she surprised me by ordering a cheeseburger. The conversation flowed, but I got a nagging sense this was more a business obligation for her than a social meeting. Still, just being with her, smelling her perfume, made my head spin.

  Too soon, the meal was over, the interview complete, and the check paid – on me, of course. It was early.

  “Hey, there’s a great ice cream place on the other side of the mall. I’d like to buy you a cone,” I offered.

  “Uh, I’m meeting a couple of girlfriends – we’re gonna go shopping.”

  “Oh,” I said. “Maybe I could tag along.” Then, in a desperate attempt to salvage the evening: “I’d like to buy you something.”

  A pause, then a response that was unnervingly businesslike. “Maybe, but since I’ll be with my friends, you’ll have to buy us each something. It’s only fair.”

  If those were her terms for spending more of the evening in this goddess’ presence, then I was in. “Yes, uh, sure. I’d be happy to.”

  Ashley sexily arched an eyebrow. “Yeah, I thought you might.”

  I trailed her out of the restaurant, admiring the view from behind, again noticing the straining male necks and enjoying the click of her heels on the terra cotta tile floor. Minutes later, she rendezvoused with two knockouts, a blond and a redhead, whom I inferred were named Tess and Julie, respectively. “Inferred” because there were no introductions. Both girls looked quizzically at me, vaguely acknowledged my smile in greeting, before turning their attention fully to their newly famous friend. Ashley could’ve been walking her dog for all the attention I received. They turned and headed down the concourse, talking as friends do, with me keeping pace behind.

  It appeared Tess, the blond, was Ashley’s best friend. She was wearing a tight, black one-piece dress with frilly hem, which stopped several inches above her knees, and a pair of fashionable shoes with sensible two-inch heels. Julie wore tight low-riding blue jeans, a red top and three-inch patent black pumps. A sliver of purple underwear peaked out from her waistline, and a Victoria’s Secret label was visible.

  As they walked, Ashley leaned into Tess and said something. Both Tess and Julie glanced back toward me and giggled. My dick quivered at the sound. Many men would’ve gracefully bowed out at that point, seeing there was no hope of getting any action and maybe retaining some dignity in the process. But I was quite literally entranced by this gleeful threesome.

  “Hey, I hope you brought your credit card,” said Julie, looking at me over her shoulder. Her eyes angled downward, and she giggled. She elbowed Tess, and I heard one of them say “Oh my god.” They all glanced back now, making me very self-conscious. My manhood stirred some more.

  The girls stopped short in front of a popular shoe boutique, known for its diversity of vampish styles and hefty prices. “I think we’ll shop here,” sang Julie. Then, turning to Ashley, “He did offer to bu
y us something, right?”

  “Yeah, anything you want. Isn’t that right, Gray?”

  “Umm, yes, that’s right,” I sputtered apprehensively, beginning to follow them into the store.

  Ashley stopped short. “No, Gray, this is a ladies shoe boutique. You’ll be much more comfortable outside.”

  I found a bench with a direct line of sight into the store. For the next 45 minutes, I watched all three women slip out of their shoes and try on several pairs of heels, prancing around in front of mirrors and testing for fit. As much as I strained, however, I couldn’t fully enjoy the show from my position outside, particularly as they displayed their pampered feet between fittings. I longed to be sitting beside them, to have the privilege of helping them on with the disposable peds and the shoes themselves.

  My state of reverie was interrupted by Ashley’s voice, and her hand in front of my face. “Cough up the plastic, Gray. I think we’re ready.”

  I fumbled in my pocket for the Visa card, and mindlessly placed it in the model’s upturned palm. She spun around without a word and went to pay for their purchases.

  Minutes later she presented me the receipt, along with the card. My eyes almost bugged out when I saw the cost of the shoes. I could’ve hired an escort for the whole night for less than what they charged to my card! And how would I pay this down while keeping the whole thing a secret from my wife? I must have groaned audibly in disgust.

  “Oh, hey, let’s show him what we bought.” Tess looked at me. “That’ll make it better, won’t it,” she sang, opening a shoe box. Inside was a lovely pair of black designer heels with silver studs and crisscross straps in front. They were nice, and no doubt would look sensational on Tess. Julie and Ashley showed off their choices, a pair of espadrilles with four-inch wedge heel and ankle strap – the kind I’ve always liked that lace up to the top of the calf – and a pair of silver open-toed slingbacks with three-inch heels. Ashley actually took one of those shoes out and rubbed the sole against my cheek.

  “You like, don’t you?” she purred. My knees nearly buckled in reply.

  “Hey, Ashley, don’t forget the surprise,” reminded Tess.

  My heart raced. Surprise??

  “Oh, right. We didn’t forget about you completely,” cooed Ashley as her piercing green eyes looked right into mine. “It was so nice of you to buy us the shoes, so we brought you these...”

  What the hell could they have gotten me in a ladies’ shoe store, I wondered. My question was answered as Ashley pulled some kind of wad out of her handbag. “Open wide,” she whispered.

  What the – ? Then something soft against my face. Their used peds!

  My shocked reaction caused the other women to giggle. Despite my strong fetish for all things foot-related, not to mention my rapture with these three women in particular, my consternation at this turn of events caused me to purse my lips tightly. We were in the middle of a shopping mall, for heaven’s sake!

  “Shhhh, shhhh,” Ashley hushed. Then, with her left hand, she very deliberately pinched my nose. Meanwhile, Julie’s hand snaked from behind to my crotch, her fingers lightly caressing my ever-growing cock. My resistance was broken. My mouth opened.

  Ashley stuffed what had to be at least eight pairs of nylon peds into my mouth, and once I sensed their redolent taste, I accepted them eagerly. If any passersby saw what was going on, I didn’t notice, nor did I give a damn at this point. By sheer will, these three goddesses had completed transforming me into their compliant pet.

  “Suck good,” Julie urged, loud enough for just about anyone nearby to hear. I did as instructed and, despite myself, felt my erection swell more.

  “Ooh, you were right, Ashley. The little wimp likes them,” Julie said, privy to knowledge the others didn’t possess at that moment. She continued to rub and lightly scratch my hard on through my pants. As she did so, she stared intently at my face, as if waiting for some sign to confirm her hypothesis. Something to reveal to the trio that I was, in fact, enamored with the idea of sucking used nylon peds in front of three gorgeous women and a mall full of strangers. A bead of sweat broke out on my forehead, and I let out a quiet moan.

  “See, he’s loving this...arentcha?”

  She had seen through me, though I was considerably less than opaque at that moment. The peds had picked up the perfume of each girl, and those scents now mingled near my palate. Together with the humiliation in this most public of venues, I was feeling a light tickling sensation in that nether region between my navel and groin, a feeling well-known to anyone who found themselves in helplessly embarrassing circumstances.

  “Listen, peckerhead,” Ashley said, leaning in close to my face. “I know your ‘interview’ was just a scam to see me again, since you don’t have the balls to approach me like a real man.” She pouted her luscious lips, looking little like the tasteful photo in the newspaper but for all the world like the woman who would soon be occupying the masturbatory fantasies of men all across the country.

  “So here’s the deal. You’re going to keep those in your mouth while we finish shopping. And you’re going to open your mouth on command. If you’re a good boy, we’ll make sure you get what you were looking for before the mall closes. But it may not be exactly the way you saw it in your dreams.”

  What could I do but agree to her terms? I was already too far in, had spent too much dough, and was way too horny, so the mere mention of a reward at the end was enough to have me practically panting through the peds in my mouth. My will was no longer my own. I would have followed these three women into Dante’s Inferno at this point. A spot of precum formed on the front of my pants.

  Julie suddenly whisked her well-manicured hand away. “Oh my god, he is such a sicko!” said Tess, interrupting my thoughts. “But this will be fun. I actually need a new outfit for an engagement party I’m going to tomorrow.”

  “Oh, hey,” said Julie. “Victoria’s Secret is having a sale. I’d like to get some thongs and stockings.”

  Ashley flashed me a sideways glance, accompanied by an evil smirk. “I’m sure Gray here will be happy to escort us.” Then, to me, “I hope you’re not approaching your credit limit.” They all giggled, and the beautiful sound reverberated below my belt.

  “Oh, hey, it’s OK,” she continued soothingly. “That’s just the price of dating a model. Besides, if you weren’t loving every minute of it you wouldn’t be sporting a woody, ha ha!”

  I couldn’t speak and my mouth was dry with the nylons bulging my cheeks. I just looked at the women imploringly, wondering how I let myself get into this position. The phrase, “be careful what you wish for” came to mind.

  The girls handed me their shoe store bags, and set off in a new direction, their heels clicking delightfully on the concourse floor.

  “Anyone else feel like a latte?” Ashley asked.

  “Good idea,” Julie responded. “The barista at the coffee place in the food court always super sizes me for no extra charge.”

  “You mean the one with that stud in her nose and big tattoo on her shoulder?”

  “Yeah, that’s her. Hey, maybe if peckerhead here asks real nice she’ll squirt some whipped cream in his mouth!” A new round of laughter, causing other shoppers to look in our direction.

  I could only groan helplessly through the damp peds.

  The Playful Babysitter Returns

  Richard Landon lay spread eagled on the bed, his wrists and ankles tied tight with his wife’s used nylons. His penis was semi-hard; Becky had been playfully teasing it a few minutes before. But her attentions were just that – a tease, a little reminder of who controlled things.

  Now, he strained his neck upward to watch her slip into a form fitting black dress with plunging neckline. And he had to twist his neck to the side to see Stephanie, Becky’s best friend, as she slipped on her ankle-strap black heels, touched up her makeup in the mirror and assessed herself in the full-length mirror. Or was she flaunting herself for his benefit?

  The sun was lo
w in the sky, and its rays streamed through the bedroom blinds. Somehow, it was even more disconcerting that they’d be leaving him like this while it was still light outside. He would be in for a long evening of frustration.

  “We’ll be leaving in a few minutes, dear. Stef and I are going to dinner, and some clubs afterward,” Becky said softly, matter-of-factly. She came over to him. With one hand, she gently tickled the corona of his penis with her red nails, causing his cock to more fully inflate. Her other reached inside his wallet for his credit card.

  Things had changed drastically in Richard Landon’s life in the past six months, ever since that fateful and humiliating night when Amber, their 18-year-old babysitter, let him have his way with her feet in the car. She’d taken a picture of the proceedings with her cell phone camera, which she sent to her friend Lauren. She, in turn, had posted it on her Facebook page. It was only up a couple of days before someone reported it as lewd and the site removed it, but in that time, several of her friends had a chance to see it, as word spread quickly.