The Playful Babysitter Page 2

  “Well, well, well, didn’t think the pencil dick had it in him, but not a bad show,” Becky said as she slipped her damp foot back into the red high heel, and buckled the thin strap. “Come on, Jasmine, lots of frat guys are waiting for us at the house – guys that can actually please girls our age.”

  The Professor vaguely heard their giggles and footsteps fade as they left the room. Just at that moment, he detected the rolling cart of the cleaning woman coming into the classroom...

  The Playful Babysitter

  Richard Landon always looked forward to his Saturday night “dates” with his wife. Sure, the dinner and movie routine was just that – routine – but they were always a nice respite from dealing with their two rambunctious kids. He looked forward to adult conversation, and he even enjoyed the sex when they got home, even though that, too, had become routine after 12 years of marriage.

  But there was another reason he anticipated Saturday nights with great enthusiasm, and it was the most important reason of all. That was the night he got to see Amber, their regular babysitter.

  “She’s great, and very pretty too,” his wife had said after interviewing Amber soon after they’d moved to the neighborhood, before he’d met her. A week later, he discovered his wife was right. She was very cute, in a girl-about-to-bloom kind of way. The high school senior, a few weeks shy of her 18th birthday, had straight blond hair that she usually wore in a high ponytail. Thin lips, expectant green eyes and slightly upward-pointing nose gave her the appearance of someone ready to meet the world and shape it to fit her needs. But he had another first impression: she seemed very...clean.

  Yes, he’d definitely classify her as pretty, but he was nonetheless indifferent toward her early on. She was a service provider, who allowed him a night out with his wife once in awhile. The fact she hadn’t yet received her driver’s license, and he had to drive her home at the end of the evening, was more of an inconvenience than anything else early on.

  But then his thoughts changed. Sharply.

  If pressed, Richard would probably say that it happened the night she wore tight fitting cotton pants, the words “Spoil Me” emblazoned on her derriere. It was the first time he’d noticed her back end. He even stammered something about the billboard he saw there, before saying something about not being in the habit of staring at girls’ rear ends. His wife was present at the time, and they had a friendly chuckle. Good recovery.

  Then, the following week, he came downstairs soon after she’d been dropped off for her evening gig and he saw her leather moccasins sitting neatly in the foyer. Looking closer, he could see toe imprints in the well-worn shoes. He greeted her in the kitchen, and his eyes were drawn to her feet. She was wearing sheer black peds, translucent enough to see very nicely shaped toes. She had on dark pink toenail polish.

  Richard had always had “a thing” for feet, which had intensified over the past few years. He was usually drawn to high heels, stockings, the occasional boot – the usual fetish objects – but before that night he never considered how sexy a pair of dirty moccasins could be. He took his wife out as planned, but couldn’t get the thought of those shoes and peds out of his mind. When he drove Amber the two miles home, he noticed how nice they looked on her.

  In ensuing weeks, Richard would make sure no one was around, then steal a few whiffs of those moccasins before heading out. The very faint foot odor was overwhelmed by the smell of leather, but the effect was to make him want more.

  About a month after he first saw the peds, knowingly or not, she upped the ante.

  She’d arrived on schedule. As they were getting ready to leave, he saw her crouch down to look at something his daughter had drawn, and caught his breath at the sight that greeted his eyes. Peeking out of her pants was a purple thong. His wife elsewhere in the house, he let his eyes linger. Now this was unexpected, especially given that Amber had always seemed very conservative. She had no visible tattoos, no piercings other than her ears. Yet she wore a thong to a babysitting appointment.

  He drove her home at the end of the night, as usual. They made small talk about the kids, the movie they’d seen, then she thanked him for the ride. He glommed another look at the thong as she maneuvered out of the car. He came very intensely when he made love to his wife later.

  Then, some good fortune.

  His wife had a rare evening business engagement, so Amber was watching the kids already when Richard arrived home from work. He walked in the house, saw the moccasins, and heard Amber and the kids in a heated air hockey tournament in the basement. The clackety-clack of the puck reassured him he’d be undisturbed for awhile – no one had even heard him come in – so he picked up the worn shoes and examined them carefully. The dark toe imprints, the soles. He noted a small wad of dried gum on the sole of one, and was tempted to remove it simply because he felt she shouldn’t be walking around in such soiled shoes. But he refrained. Instead, he inhaled deeply of the insides. He stuck out his tongue and tasted those imprints.

  Getting more and more aroused, he unzipped his pants and pulled out his semi-hard cock, then began rubbing it inside one of the moccasins. A small drop of pre-cum mingled with the moisture left by his tongue. He dared not go further. She’d be leaving soon, but he doubted she’d notice anything. Was she barefoot tonight, he wondered?

  As it turned out, she was wearing ankle socks, so his indiscretion would go unnoticed.

  Several weeks went by and Richard took note of everything Amber wore, and began noticing her pert breasts, usually accentuated by a tight-fitting T-shirt or sweater of some kind. As the weather began to get warmer, she’d show up wearing flip-flops, her nicely manicured toes on proud display. And she frequently wore the thong panties.

  At the end of their drives home, he began giving her monetary tips of $5 or so, even though his wife had already paid her. “For being so reliable,” or “for coming on such short notice,” he’d say. She always politely smiled and thanked him.

  He wondered whether she was making the connection between the thong underwear and the tips. Whether she even gave conscious thought to why he was paying her extra, and doing so covertly. He even wondered if, when talking to friends in school that week, she told them about the “secret” gratuities from the odd, probably horny, but pleasant 40-year-old guy she sat for.

  In Richard’s mind, he was rewarding her for the after-image that stayed with him for the week. He thought of it as some kind of unspoken, prostitution-light relationship, in which only one party was aware of what was happening. In any case, he was happy to contribute the extra cash toward her clothing, makeup, savings for a car...whatever.

  About six weeks after her 18th birthday, a date which Richard had marked on his mental calendar, he drove her home as usual. She was wearing the moccasins. He noted how nice she smelled – a clean, earthy scent – and decided it was time to lay it all on the line.

  As he handed her a $5 bill he said, almost jokingly, “I’ll – I’ll give you another $10 for your moccasins.” He could hardly believe he actually said it, and his voice cracked as he did.

  “Excuse me?” was her response. Did he detect a tinge of anger?

  Richard cleared his throat. “I’ll give you an extra ten bucks for those ratty moccasins. You can use it toward a new pair.”

  Amber made a face, considering the offer. “I like these shoes...they’re the most comfortable ones I own. Besides, what do you want a pair of my old mocca.....Oh.”

  Realization washed over her face, along with a smile. She giggled, then: “I do really like these. But I’ll tell you what, Mr. Landon. For $20, I’ll let you kiss my feet. How’s that sound?” She arched her eyebrow, then smirked. “And for an extra $10, I won’t even tell Mrs. Landon.”

  Had he just heard what he thought he did? His cock rose up unbidden in his slacks. Conflicting thoughts ran through his head. This girl was more mercenary than he ever thought, and far more savvy. Was she actually blackmailing him with her counter-offer?

  He didn’
t respond for more than 30 seconds, except for a gulp. “How about it?” she prodded. “You know it’s what you really want to do.”

  Wow, it didn’t take her long to get inside his head, Richard thought.

  “Um...yeah...OK,” he stammered as he reached for his wallet, pulling out a twenty and a ten. His hand was shaking as he gave the bills to her.

  “Not in front of the house. Drive to the duck pond,” Amber instructed. When they arrived in the desolate parking area, she maneuvered so her back was against the passenger door. Slowly, she lifted her right foot out of the leather shoe and brought it in front of his face. Her toenails glistened in the moonlight, and Richard detected a slight hint of perfume. It was all he could do to keep from swooning.

  “Enjoy,” she said, giggling.

  He found that he had to lean forward to reach her toes, and he figured that was by design. It would’ve been nothing for Amber to bring her foot three inches closer; she apparently wanted to see him strain for the privilege.

  And a privilege it was. He planted a servile kiss on her big toe, then the ball of her foot. His head spun with the reality of doing something he’d been thinking about for weeks. Without asking her permission, he began to lick.

  “Ooh, Dickie, that feels good,” Amber said imperiously. “Get between my toes, too.” His ears stung at the sudden informality, but he could hardly tell her it was “Mr. Landon” or even “Richard” while his dignity was going to shreds before his taunting seductress’ eyes. All he could do was spear his tongue between her toes. His cock was nearly bursting his pants. The slight salty taste, combined with the mild perfume and light leather scent, manifested themselves physically below his belt. He involuntarily groaned, and she slid her first two toes into his mouth. He accepted them eagerly.

  “Mmmm....just like that,” Amber cooed.

  Richard slurped at her toes lasciviously, hardly noticing her left foot moving toward his crotch. He sucked in his breath the moment it came to rest on his hardness. Her delicate heel began to slide up and down. His head swam.

  Suddenly, inexplicably, he heard the music of Coldplay. What the—? It took a moment to realize it was Amber’s cell phone.

  “Hi, Lauren,” she said, flipping it open.

  “What’s up? We getting together?”

  Richard realized she had the phone on speaker. He paused, but Amber snapped her finger and pointed down at her foot. He continued his joyous sucking, if a bit more self conscious.

  “Yeah. I just finished babysitting. What do you want to do?”

  “We could rent a movie, or – hey, what’s that sound?”

  A conspiratorial giggle. “You know that guy that I sit for? The guy I said is always looking at me? Right now, he’s licking and sucking my toes.”

  A new wave of shame coursed through Richard’s veins. His head throbbed, and he had no doubt his face was beet red. But at the same time, his cock throbbed, and Amber seemed to detect it under her other foot. She smirked again, in the way one uses exaggerated facial expressions to communicate with someone in the room while engaging in a phone conversation.

  “Get out of here!” said the disembodied voice. “Stop putting me on.”

  “No, really, he is. And guess what – he’s enjoying himself. He can’t hide it – if you get my meaning. Hee hee.”

  “Bullshit. Just get over here.”

  “Really!” Then she paused, sexily biting her lower lip. “Wait a second, I’ll prove it.”

  With a giggle, she held up the cell phone at arm’s length. No, she wouldn’t, Richard thought. She would.

  “Say ‘toe cheese,’” Amber sang. Then a flash as she used her cell phone camera to photograph him. The scene absorbed by its lens, then instantly transmitted via cellular tower to the cell phone in the manicured hand of her best friend Lauren, and no doubt those belonging to other girlfriends in the course of the week, was this:

  A forty-year-old man (though both girls might debate whether he was a man at all), three girl toes stuffed into his mouth, his face a deep shade of red, his eyes helplessly locked on the smirk of his 18-year-old tormentress, and a very large – and very obvious bulge in his groin area.

  His shame welled up, but she felt his cock grow under her now-wiggling toes. This only encouraged her more. No longer could Richard deny that he was loving this.

  “Eeoow!” came the voice on the cell phone. “He is such a loser! Why would he want to suck your toes? They stink!”

  She giggled. “He doesn’t care. Probably the stinkier the better, as far as he’s concerned.” More laughter.

  “What?”

  “He paid me to do this. Apparently, he likes girl feet.”

  Richard’s shame now bordered on physical illness. Yet he couldn’t bring himself to stop sucking Amber’s lovely toes despite the intense humiliation. Even if he did have any pangs of dignity, the heavenly movement of her other foot beneath his belt assured his compliance.

  He felt an ejaculation coming – his crotch was already damp with pre-cum – but he feared that it would happen while she was on the phone. No! He couldn’t allow that. Even now, even with this goddess taking control of him, there were limits.

  Laughter came from the phone. “Gawd! You sure can pick ‘em, Amber.” A pause. “Hey, am I on speaker?”

  Amber chuckled. “Yeah, he can hear everything.”

  “Oh, how sweet is that! Hey, Mr. Toe Sucker, or whatever the fuck your name is – leave my friend Amber’s feet alone!”

  Richard’s cock swelled even more upon hearing Lauren address him. His head was swimming...and he felt like he was outside of himself. But his tongue continued swirling around Amber’s big toe, and he let out a moan.

  “Uugghhhh,” mimicked Lauren, disdain dripping from her voice. “Listen, loser, we just made plans for tonight, so do whatever it is you perverts do and finish up.” Richard could practically hear the sneer in the teen’s voice.

  Amber picked up on the cue. “Come on, Dickie,” she cooed, the ball of her foot sliding up and down his bulge. “Shoot for the babysitter.”

  He groaned again. The thought of cumming in his pants, while being heard on the cell phone no less, was absolutely mortifying. It would be hard to hide the stain from his wife. Yet there was little he could do to prevent it. The toes in his mouth and on his cock coaxed him on; the smirk on Amber’s face hypnotized him.

  “It’s okay...” she whispered soothingly.

  Richard’s body seized, and he had to release Amber’s toes from his mouth to avoid biting down on them. He fumbled for his fly, vainly trying to release his penis before staining his pants, but Amber’s foot held firm, impeding his efforts. He could only grunt in helpless rapture.

  “Oh my god! Lauren, he’s cumming in his pants! My foot’s all wet. You should see this!” She looked straight at him, sucking in her cheeks and arching one brow in a strange mix of admonition and approval.

  “Quick, take a picture!”

  “Smile, Dickey.” The cell phone flashed.

  His shame was complete as he heard Lauren’s voice calling him a loser. Amber’s foot kept massaging his rod, summoning all the cum he had.

  “Ooh, poor baby messed his pants,” Amber cooed. “Might be a problem with wifey.”

  His wife! Richard’s mind raced as he thought about how he could hide the growing stain. Maybe she’ll have the bedroom light off by the time he returns...

  “Oh my gosh, this picture is hilarious,” said Lauren. “Look at his face! This definitely goes on my Facebook page tomorrow.”

  Richard was too exhausted, too humiliated to respond. How could he even look at Amber in the face again, let alone drive her home after a night out.

  “When...when do you get your driver’s license?” he plaintively mumbled.

  “Hey Dickie, news flash – she got her license eight months ago!” came the voice on the cell phone. His ears rang with sexy, girlish laughter.

  Model Humiliation

  I first saw her picture in the
daily newspaper. The gist of the story was “local girl makes good,” but it wasn’t the text that drew my attention. The black and white photo staring out at me sucked my breath away. Large, gorgeous eyes, shoulder-length blond hair in a tasteful wave, and a small, self-aware smile that practically said “I know what I’m doing to you.” It was the first time I would learn of Ashley Blake.

  The 21-year-old, the story said, had been selected as the first Miss Loaded, and for the next year would carry the banner of the popular men’s interest magazine known for its bikini-clad babes and irreverent look at life from a horny male’s perspective. She’d won by popular vote among visitors to the magazine’s website, beating out 63 other beauties from across the country. Remarkably, despite her new-found fame, Ashley Blake remained employed in a local men’s hair salon.