Nylon Tease: A Front Seat Fucking

Summary: Young teacher is seduced by MILF colleague.

Note 1: This is a 2017 Holiday Season Contest Story so please vote.

Note 2: Thanks to Tex Beethoven, Robert, thor_p, and Wayne for editing.

Nylon Tease: A Front Seat Fucking

"Can you give me a ride to the city this Friday?" Collette asked.

I was barely listening as I had watched her walk into my classroom and up to my desk... staring at her mocha clad silk stocking legs... my utter weakness... nylons.

Pantyhose, stockings, thigh highs, tights all had my cock instantly hard and ready for action.

And although I liked all colours, mocha or coffee, a dark brown, was my favourite.

I answered, trying to look into her eyes and avoid looking like the creepy colleague I was, "S-sure."

"You okay?" she asked, as she slipped her left foot out of her heel to reveal alternating red and green seasonal painted toenails... my cock flinching in my pants.

Although nylons were my fetish, sandal-foot style with the clear toe was my kryptonite. I couldn't explain it, but feet and toes in unobstructed translucent nylons were my biggest visual turn-on... more than tits, ass, eyes, hair, pussy or whatever else was more conventional.

Completely distracted, as I watched her wiggle her toenails as if giving me a subtle wave, I said, "Um, yeah, just distracted."

"By what?" My British MILF colleague asked, moving her foot back inside her shoe... hiding the tempting toes.

Breaking my trance, I looked back up, sheepishly, trying to be suave while also indicating my obsession, "Those are some seasonal toenails."

She slipped her foot back out and wiggled her toes again, "You think so? It was my daughter's idea."

Her daughter Bethany was in my English class, and was a knockout like her mother. Also like her mother she was the only student in school who regularly wore nylons. And, still like her mother, she had an affinity for slipping her feet in and out of her shoes... creating her unique version of a hypnotist's watch as I would spend the entire hour when she wore nylons checking out her legs and her feet.

Am I a pervert? Yes.

Is my fetish weird? Yes.

Was she of legal age? Yes. Moving from England when she was nine, she'd ended up a year behind her peers and was closer to nineteen than eighteen.

I broke free from my perversion to acknowledge her reply, "Yes, I think it's very festive."

"You're so sweet," she said warmly in her sexy English accent, giving my arm a squeeze, "My husband never even mentioned my toenails."

She appeared to be giving me just the slightest sexual innuendo with that, as if I were in a competition with her husband for her favour and I'd just scored a point. Although I was a first-year teacher here, Mrs. Jones (or Collette, as I was now privileged to call her) and I went way back. She'd been my English teacher in this very high school eight years ago and I'd had a mammoth crush on her back then... okay, and a sexual fixation too if you must know... and I'd been fantasizing about her off and on ever since. I'd gone through college on a full ride football scholarship even though I was an English major if you can believe that, then after graduation I'd played three years of professional ball, mostly as a linebacker on special teams, before returning here to my alma mater. Now I was an English teacher and football coach here, and as if she'd been waiting faithfully for me, my hot teacher Mrs. Jones had become my friendly and hot colleague Collette.

Failing to find a snappy comeback, I settled for, "Oh, well it's the time for giving."

Furthering her secret innuendo (if it was one) she quipped, "And receiving."

"Well, of course," I agreed, glancing again at her nylon-clad foot and her adorable perfectly pedicured toes.

She wiggled her toes one more time before slipping her foot back into its leather prison and said, "Well, I'll be fully in the giving mood when we head out on Friday."

Her tone and words seemed to be to be dripping with innuendo, but I couldn't be sure. I mean she was almost twice my age, my former teacher and married. Yet, if she were my age and single I'd be turning on the charm in hopes of scoring; and actually if she wasn't my colleague I would be doing the full court press. Yet, not wanting to let that go unanswered in case she was flirting (okay she was definitely flirting, but in case it was more than flirting, she wouldn't be the first married women to hit on me (I fucked my college coach's wife my entire senior year and have fucked more married women than women my age)), I said, "Well, 'tis the season."

She pulled her foot out of her heel again and wiggled her toes purposely, drawing my quick-trigger gaze instantly back to the floor. "That it is."

She just as quickly hid her foot back out of sight as I repeated, hinting at my fetish, "I do love those seasonal painted toenails."

"Good to know," she turned with a wink and nodding her head, she walked out of my room. No doubt that was a wink. No doubt she was flirting. Yet lots of doubt about her intent.

That was Tuesday.

The next three days were excruciating.

On Wednesday, ugly Christmas sweater day, Collette walked into my room wearing a hideous sweater, a plaid skirt and mocha nylons... and... as if deliberately tempting me... no shoes... her nylon-clad feet in full view. She admonished, looking at my sweater, "That isn't much of an ugly sweater."

I didn't have an ugly Christmas sweater and was too cheap to buy one, so I was just wearing a ski sweater. I countered, "I think yours is outrageous enough for two."

"You don't like my festive attire?" she pouted, giving a pose.

"I think you look very festive and likeable," I said, my eyes being pulled like magnets to her red and green painted toes... showcased so perfectly in the dark coloured hosiery.

"I love Christmas," she said, before adding again with a tone that crossed the line to extreme flirting, "I love giving and receiving, especially with people I like."

"I do too," I replied, thinking the naughty Christmas elves were really testing me here. God, I'd love to fuck her.

In truth I've always preferred older women, especially married older women (I know that makes me an asshole, but I can't resist them) for a few reasons:

1. The obvious, they are more experienced.

2. They are often neglected by their husbands and desperate for attention.

3. They love my big barrel and my ability to reload very quickly.

4. They don't want a relationship or to talk... they want to fuck.

5. They do the things girls my age often won't (swallowing, facials, anal).

6. They call me when they need a booty call and are genuinely appreciative when I come (and then come).

7. They are usually nasty and verbal (so many girls today are boring in the bedroom, not all mind you, but more than are not).

8. They like to share (I've had referrals from one MILF to her friends on a couple of occasions. And had even had my first threesome with two best friends who had never done anything lesbian with each other until I suggested it).

9. Older women wear nylons more than younger girls today (a nylon sighting on a younger girl is almost as rare as a politician telling the truth).

10. They can go for hours... treating each night with me as if it is their last fuck before going to the sexual guillotine.

"Do you have the Hamlet DVD?" she asked, bringing me back to reality.

"Aaaah, Yeah, sure," I nodded, going to my DVD player as I'd finished watching the epic Kenneth Branagh version, the sword throwing part both brilliant and hilarious.

"The others are showing the Mel Gibson version," she said with contempt.

"I know," I said, my tone slightly disgusted. "There are no redeeming lessons in that one."

"I couldn't agree more."

"Mel should've made Lethal Weapon Five instead," I joked, as I handed her the DVD, once again glancing down to her seasonal pedicure.

She disagreed, "They should have stopped that series after part two."

I laughed, "You didn't like Joe Pesci?"

"In My Cousin Vinny yes, in Lethal Weapon no. They turned it from a gritty cop series to a formula comedy," she responded seriously.

"Fair enough," I nodded, although I could have argued he plays pretty much the same character in both.

"Thanks," she smiled, as the bell rang.

"No problem," I said, as I glanced back down again to get one last look at the nylon-clad feet I wanted to feel in my hands, to feel stroking my cock, to feel wrapped around my legs, or to feel her toes in my mouth.

"Looking forward to the weekend," she finished, somewhat sing-song, as if an English assessment conference was a good time.

"Me too," I said, although my reason was a fantasy of fucking this hot MILF.

A couple hours later Bethany arrived in my classroom, thankfully in jeans and thus I wasn't distracted all during class. The only thing hotter than fucking a MILF was the idea of fucking a mom and daughter, something I had yet to do. I had fucked a mom and a daughter separately, but never together, my biggest fantasy not yet fulfilled.

That night I jerked off while visions of Collette dropping to her knees under my desk and giving me a blow job danced through my head. Somehow I just knew she would give great head. Her lips were sensual and just looked like great cock sucking lips.

Thursday I only saw her in passing, in a black skirt and black pantyhose.

Her daughter on the other hand, was in a plaid skirt similar to the one her mother had worn the day before, with similar mocha nylons, and as she wrote her Hamlet test, she slipped her feet out of her shoes and literally moved her feet up and down her legs all class... the most erotic fidgeting I had ever witnessed.

My cock was hard the entire hour and I had to readjust behind my desk before doing my walking tour or to go to the whiteboard to answer a question.

Thursday night I jerked off to the fantasy of Bethany using those sexy, cute feet for stroking my cock.

Then came Friday.

Did I expect anything to actually happen?

Not really, but a guy can fantasize.

My hope dwindled when I saw Collette and she was in jeans. I mean it was casual Friday and she usually wore jeans on Friday (yes, I paid attention), but she usually still wore heels and nylons with her jeans, something that was incredibly rare. But today she was wearing runners.

Her daughter was gone for a basketball tournament, thus it was a no nylon day.

The day went by uneventfully and as I was packing up and grabbing my suitcase, which I'd brought in so my clothes wouldn't be frozen as it was bitterly cold outside, Collette walked in and asked, "Ready to go?"

"Suuuuuuure," I answered, turning around, shocked to see she was no longer in jeans, but wearing a very unpractical blue skirt, mocha nylons and boots with a massive heel... a jacket covering whatever blouse or shirt she was wearing. Why would she possibly change into something less comfortable for a two-and-a-half-hour drive? Not that I was complaining!

For the first time really, other than silly teenage fantasies, I thought maybe she was into me. There was no logical reason to change out of comfortable travel attire and into something that was definitely not comfortable travel attire for a two-hour drive, especially on a day that was way minus 18 Celsius outside (not including the wind chill).

She laughed, "Are you okay?"

"Yeah, yeah," I nodded. "Just looking forward to getting on the road."

"Great, me too," she nodded, and we headed out to my car talking about the week and generic stuff, which continued for the first hour of the drive... as I tried to focus on the road as much as possible and not her mocha-clad knees and lower thighs.

Like most women, just under half way to our destination she uttered the dreaded words, "Can we stop soon? I need to pee."

"Sure," I said, hiding my usual annoyance. I hated stopping when on a drive. I made sure I had a bottle of water, I made sure I had a full tank of gas and I made sure I went piss before I left. But, she didn't need to know this. Plus, we were making pretty good time.

Five minutes later we pulled into a truck stop just outside a small town and she scurried out. I went inside and grabbed a chocolate bar, a Mr. Big, and was back in my car before she was done with her washroom break.

She came back in and sat back down and saw me taking a bite out of my Mr. Big chocolate bar. She smiled and asked, "Is that advertising?"

I laughed, trying to act suave, "I've never had any complaints."

She smiled and hung something on my mirror. She said, as I realized it was mistletoe, "To make your car a little more festive."

"That and your toes and we're in a Christmas wonderland," I joked.

She said, "Um, do you not know how mistletoe works?"

"What?" I asked.

"When a woman is under the mistletoe you're supposed to kiss her," she replied, as I realized she had indeed put her head under the mistletoe.

I nodded, "Oh, right, I wasn't sure that rule applied to co-workers."

"Matthew, this weekend we are not co-workers," she replied, as she closed her eyes and puckered her lips.

I was completely bewildered as I stared at my biggest MILF fantasy waiting for a kiss. Did she want a peck? A kiss? A tongue down her throat?

I leaned in and kissed her lips; it was more than a peck, as I kissed her lips and lingered there while she kissed me back. It was only five seconds, no more, but more than a kiss between co-workers.

I leaned back to my seat and she leaned back to hers as she took my chocolate bar and took a bite. As I put the car into drive, she said, "I love Mr. Big."

"Me too," I said, and if hers was sexual innuendo, mine sure wasn't.

She said, returning to the conversation before the Mr. Big and mistletoe, "I've never done that before. I'm usually a red or off-red type of toenail girl."

"A classic choice," I agreed, red being my favourite colour of nail polish on a woman's foot. Red was classic, red was sexy.

A couple minutes of silence and she suddenly asked, "Do you mind if I take the boots off, it's too warm in here."

"Sure," I responded, perhaps a little too eagerly.

"Thanks," she replied, as she moved her foot onto my dashboard and unzipped her boot. I had to focus extra hard on the road, especially as I was passing a semi at the time. Hate to kill us both because I wanted to see her foot in sheer nylon.

"No problem," I replied. "I want my passenger to be as comfortable as possible."

"Well, aren't you a sweetheart," she said, her across-the-pond accent making it sound even sexier.

"I love making people happy," I said, trying to hint at something more sexual than the bland words I used.

She pulled her boot off and asked, "Why are you single then? You'd be a great boyfriend."

Deciding to push the envelope a little more, taking a lengthy look at her nylon-clad toes before she moved them down and out of sight, "Girls my age are exhausting."

As she moved her other boot onto the dashboard, she asked rather coyly, "Isn't that a good thing?"

I sighed, dramatically on purpose, "I wish." I then decided to be frank with her. "Young girls today are drama queens and, truthfully, the sex is rarely all that good."

"That wasn't the case when I was young," she said, unzipping her second boot.

"Today's generation," I joked.

She agreed, as she pulled her second boot off, "Yep, entitled and lazy. I'm disappointed to learn that even includes sex."

I was about to respond when she surprised me again by putting both her beautiful feet on my dashboard... suddenly all ten toes... five red and five green... were in clear sheer view.

I stared a moment, wishing I could somehow take a photo of her feet as I wanted to forever remember the picture-perfect pose. Deciding to continue to hint at my willingness to fuck her I revealed, "That's why I generally date older women."

"You do, do you?" she asked playfully, her tone and wicked smile dripping with playfulness. She then added, apparently knowing my reputation of fucking women and not dating them, "Is that what they call sex nowadays?"

I laughed, even as my cheeks went a bit red, "I was trying to be a gentleman."

She said, "We're not at work, you can be frank with me," she said, before she asked, or more like acknowledged, "You're a leg guy, right?" she assessed.

"I guess," I agreed, rather non-committal, as I reluctantly stopped staring at her perfect toes.

"It's pretty obvious," she continued.

"It is?" I asked, although that didn't surprise me since I couldn't ever resist staring at her feet at work or now. Thank God the roads were good today or I'd likely be in a ditch by now.

"Yeah, although I'm guessing you're even more a foot guy," she said, as she wiggled her toes and I automatically looked at them.

"Yeah, I am," I admitted, seeing no harm in admitting it since she already knew. I then added, "Since you've already busted me, I'm more a leg and foot in nylons with your gorgeous toes showing kind of guy."

"I figured," she nodded. "You drooled over my legs back when you were a student, didn't you?"

"Maybe," I answered trying to keep it casual, even though the truth was obvious.

"Be honest, did you have any fantasies about me when you were younger?" she asked, her toes constantly moving.

"Who didn't?" I answered. "You were hot and always dressed sexily."

"I was hot?" she questioned, with a pout.

"You're still very hot," I corrected myself.

"Do you fantasize about me now?" She asked, shocking me again.

"I plead the fifth," I chuckled, since it was obviously true.

"We're in Canada so that isn't an option," she pointed out, as she stretched her legs all the way out, her feet now pressing against my windshield.

I glanced down and gasped. Her nylons were stockings. I could see the tops of them being held up by a garter. The conversation, the bluntness, the kiss, and now the lingerie, and I was suddenly confident all the flirting was indeed leading to something more. I answered, even as I stared at her thighs and her skirt riding up, "Yes."

"Yes, what?" she asked.

"You want me to say it?" I questioned, excited but a bit overwhelmed. She was my original MILF fantasy.

"I do," she nodded, acting like she had no clue she was revealing a lot more leg than appropriate.

"Collette, you were my first TILF fantasy," I admitted, before adding "and my first MILF fantasy. Shit, you're likely the reason I'm a nylon fanatic."

"What's a TILF?" She asked.

"Teacher I'd like to...."I answered, avoiding the last word.

She smiled at me as she asked, knowing full well what the last word was, "Tell me what, Matthew, I'm a teacher you'd like to what?" As she asked this, she suddenly spun her body around and in one lightning move her feet were both on my crotch.

I groaned, as every last lingering doubt was suddenly gone. I answered bluntly, "A teacher I'd like to fuck..." I then added, with clear intent, as she moved her feet slowly around on my hard cock, "... hard."

This time she moaned, "It is indeed hard." She then asked, "So was I a teacher you wanted to fuck, or am I a teacher you want to fuck?"

I didn't hesitate as I noticed her past versus present tense question, "I would have fucked you in a heartbeat when I was a teenager."

"But not now?" she asked, the three words asked with a sultry seductiveness implying she already knew the answer, as she moved one foot up to my face and rubbed my cheek... which was erotic and rather distracting and dangerous.

Taking control, sensing she was looking for a man who knew what he wanted, who knew how to treat her like a slut for a night, I answered, "Now I'd fuck you all night and turn you into my personal slut for the entire weekend."

To my surprise and disappointment, she moved her feet away. I feared I'd pushed too hard by calling her a slut. Most older women loved being called names as I fucked them, but maybe Collette was different.