MILF for Christmas

Summary: Lucky guy gets kinky romantic encounter with hot teacher.

Note: This is a 2018 Holiday Story so please vote.

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

MILF for Christmas

Being a brand-new high school teacher, I was overwhelmed by all the minutia of duties and student counseling they hadn't taught me in college. Not that I was officially a counselor, but in addition to their questions about classroom subjects, both the boys and girls were constantly coming into my office to ask for my advice about their life problems, as if I were an expert on them.

The semester had flown by, and I'd survived in large part because of Danielle. She was a student services teacher who helped me create the individual programming many of my modified students required.

There sure is a lot they don't teach you at Teacher College.

In addition to her being an amazing help, she was also a constant distraction to me. She wore pantyhose every day. They were clearly expensive pantyhose, always in my favourite mocha colour, with a sexy shimmer to them.

I also found it distracting when she dangled her heel from her toes, as if trying to hypnotize me with the pendulum-like motion of her footwear. She did this often, and I frequently wondered whether she realized the impact she was having on me.

And just to make things almost unbearable, for the past month she'd begun walking around her small office in her stocking-clad feet, which was my ultimate weird obsession: feet in nylons.

I got turned on by seeing toes in nylons.

I got turned on by seeing painted toes in nylons.

I got turned on by seeing the sole of a foot in nylons.

I got turned on by seeing a heel in nylons.

I got turned on by seeing the entire assembly of a foot in nylons.

Conversely, and unexplainably, those same presentations not wrapped in nylon did absolutely nothing to me. Nada! Zippo! Zilch!

Through the wonderful world of the Internet, I learned that foot fetishes are quite common.

Nylon-only foot fetishes are a lot less so... not even close to some of the particularly strange other fetishes I'd discovered online, such as furry play (dressing up in animal costumes and having fuzzy sex) or infantilism (dressing up as and being treated like a baby).

So whenever she dangled her shoe, or wiggled her toes, or just sauntered around in her stockinged feet, I was completely captivated.

She also was very touchy feely, gently but persistently grabbing my upper or lower arm and giving it a squeeze whenever she was talking to me.

That said, she was married and twice my age, so she was completely off limits.

But then one day she wasn't... wasn't married, that is... but she was still twice my age.

She didn't talk about her breakup, never mentioned it, the only clue was her email signature being changed from Walsh to Campbell.

In December she added to her fuck-am-I-going-to-drive-you-nuts actions by almost always having a candy cane in her mouth. She didn't suck on it like it was a cock or anything, but just seeing her lips wrapped around the small shaft had my mind picturing wicked images of a thicker, different-coloured shaft encircled by those perfect lips.

On Thursday, the second to last day of school before the Christmas holidays were to begin, just as I was packing up to go home, she walked into my classroom, sauntered was more like it in her nylon-clad feet, which was the first time I'd seen that outside her office, and asked me, "Jimmy, are you available around five?" It was already past four-thirty.

"I think so, why?" I answered, my eyes helplessly scanning her legs and feet. God, whatever pantyhose she purchased, I needed to find, for whenever I got a new girlfriend. Most girls I dated found my pantyhose fetish weird or outright inconvenient, one of them even angrily called it sexist, but some wore them for me... as had the majority of the MILFs I'd scored during my college adventures.

"I need someone to play Santa at a fundraiser this evening," she explained, sounding a bit desperate, wiggling her toes in front of me as if knowing that would encourage me to say yes.

I stared at those toes way too long before breaking the hypnotic pull they had over me and joked, "You think I have the physique to play Santa? Thanks!"

She laughed as she looked me over, "God no, you hunk, but we have padding available to give you that Santa look."

She casually placed a foot up on a student's desk seat and adjusted her nylon: toe to top.

My eyes went wide: not at what she was doing, although perversely I found it hot, but because to my surprise, I now knew she wasn't wearing pantyhose as I'd always assumed, but thigh highs. I could see part of the stocking top... just barely... but enough to let me know.

Although I liked pantyhose, I loved thigh highs or a garter-belt and stockings... you know, for the obvious convenience reasons.

A pantyhose-enhanced ass was sexy as fuck.

But a pair of sexy-looking thigh highs could remain in place while I had my face buried between a woman's legs or had my cock sliding into her pussy, and when she wrapped those silky-clad legs around me, it felt like pure heaven.

"Deal," I decided before adding, "but you'll owe me."

"Anything you like," she said easily, placing her foot back down on the floor.

I chuckled, "'Anything' is a pretty wide-open spectrum."

"Okay then," she renegotiated, wiggling her toes again as if knowing I was obsessed by them, "almost anything."

"Already changing the deal?" I joked.

"You think I'm trying to weasel?" she asked as she walked towards the door. She turned back and added with what I could only read as playful flirtation, "then we're back to 'anything you like'. Sky's the limit, Santa."

Before my brain could unfry itself enough for any witty banter or follow-up, she'd strutted away.

I adjusted my hard, excited cock and thought to myself, What just happened?

I then realized I had no idea where I was supposed to be going.

I finished packing up my briefcase; there was no way I was doing any more work after that encounter, and I grabbed it and hurried down the hall to her office.

She was putting on her winter boots, this time with her entire other thigh high stocking and even a tiny bit of bare leg in clear view, when I walked in.

"Mrs. Robinson," I smiled playfully, as she was in a very similar pose to the classic movie, "Are you trying to seduce me?"

She smiled, letting her leg remain up a little longer than necessary, and answered, "Trust me Benjamin, if I were seducing you, there would be no trying."

I was speechless.

"What can I do for you?" she asked me a moment later as she put her leg back down as if she hadn't just rocked my world.

"Where is this event?" I asked.

"Oh right," she said, shaking her head. "I got distracted."

I wondered what had distracted her. Was it me? She wouldn't be the first MILF who had tried (and succeeded) to seduce me.

I knew what was distracting me. I joked, continuing a sly flirtation that could be taken as such, or just as harmless banter, "I'm told I do that to a lot of the ladies."

"I know. That's what your students say," she informed me.

"Pardon?" I asked, not knowing what she meant.

"Surely you know that half of your female students have a crush on you, and likely a few of the boys?" she pointed out.

"They do?" I asked, having never noticed any such thing. Sure, I knew a few students checked me out, but I hadn't given it much significance. It was true they were only five years younger than I, but to me that seemed like a large gap, because of their universally superficial personalities. I just saw them as immature kids, and even though I found some of the girls undeniably attractive physically, they had no impact on me. Thankfully none of them wore nylons (except for Allison, who was more nerdy than sexy), since that might have changed my perceptions.

When you came down to it, my thing had always been for older women.

I lost my virginity during a football summer camp to the woman I was boarding with. I'd frequented a club during college that was famous for hosting cougars, where I scored many hot conquests.

Older women didn't want to talk.

Older women didn't want to be wined and dined.

Older women didn't want to cuddle afterwards.

Older women did want to fuck.

On top of that, they had experience.

My best blow jobs were always given by cougars.

My best fucks were always with MILFs.

Plus, they were way more likely to wear nylons.

They were also much more likely to do things girls my own age refused to do: swallow, take facials, take it in the ass, talk nasty, etc.

Although I couldn't fathom Danielle doing any of those things, I had learned early on that looks could be deceiving. My mom's best friend was a mother of four who had seduced me during the summer between my freshman and sophomore year of college. She'd sucked me in her living room while her kids were outside in the pool; I'd fucked her ass in the kitchen while her husband was in the bedroom taking a nap. She loved being treated like a slut, and it was a great summer, when I'd discovered the power of a big cock and of stamina.

"You're adorable," Danielle said.

"Most men don't consider that a compliment," I pointed out.

"How about cute?"

"I loved hearing that when I was six."

"Handsome?" she tried, walking towards me.

"Getting better," I smiled.

Now standing right in front of me she said, her tone a little sultrier, but maybe just because I wanted to hear it that way, "Sexy."

Deciding to flirt back, I suavely responded, long used to these subtle cat and mouse games, "So we're switching the subject of these adjectives to you?"

"You're quite the charmer," she smiled, turning away and swaying out of her office as my cock raged.

"I still don't know where I'm going," I called after her.

"Just follow me," she ordered.

I did, enjoying the view of her ass swaying, all the way out of the school building and across the dimly lit parking lot. The almost-winter sun had already set, and the sky was in twilight.

"Try to keep up," she said, as she got into her car.

"I've never had a problem with that," I responded, my reply a not-so-subtle come on.

"Good to know," she said, as I climbed into my own car.

I followed her for a few minutes to a community hall.

She waited for me to park and said when I climbed out, "I really appreciate your doing this so last minute. Our original Santa called just an hour ago to say he has the flu."

"No problem," I shrugged, as we headed into the hall. "Plus, I've been given a coupon for some sort of anything."

"Some sort?" she asked, raising an eyebrow.

"Exactly," I answered, not giving away any of my cards, yet encouraging her to take my innuendo as far as she wished.

"Well, that coupon means what I said," she reaffirmed. This time her tone definitely changing into sultry as she stressed each word, "I... mean... anything."

"I'll keep you to that," I promised, my cock having flinched with each of her breathy words.

"You'd better," she purred, her tone and look ones I'd encountered many times before from horny MILFs. I think she was even about to reach out and squeeze my cock, but we were interrupted.

"Mrs. Walsh, did you find a Santa?" A woman asked frantically as she rushed towards us.

"It's Ms. Campbell now," Danielle corrected her, but giving me a telling look, as if emphasizing to me she was single and looking.

"Sorry, right. I'm so sorry about that," the woman apologized.

"Oh, it was a blessing in disguise," Danielle forgave her with another sizzling look at me. I wasn't one hundred percent certain, but I was a good ninety percent sure she was giving me a wide-open offer.

"So... is this guy our Santa?" the woman asked.

"He is," Danielle nodded.

"Come with me," the woman ordered brusquely, without even asking my name or telling me hers. "There's already a lineup for you."

"Duty calls," I shrugged at Danielle and I was led into a small room where I got dressed in the red and white outfit. With plenty of padding.

Once it was on, the unintroduced woman led me out, and I spent the next two hours in what can only be described as a holly jolly event worse than hell. I mean I already knew I didn't ever want to teach younger kids, but that antipathy was confirmed times infinity as I dealt with endless whining, crying, selfish, obnoxious kids who wanted unreasonable things. For instance, what was I supposed to do when an eight-year-old burst into loud wails when I wouldn't promise to bring him a swimming pool? Fortunately for me, Danielle whispered into my ear to trust her and just agree, then while the squalling brat was calming down, she quietly suggested to his mom that she get him a little plastic wading pool.

The only positive aspect to the ordeal was that Danielle was there the entire time, having dressed up as Mrs. Claus.

Even better, the entire time she kept walking around Santa's Workshop in her stocking-clad feet, which kept my cock hard throughout the nightmare of endless little kids.

Thankfully, after surviving two hours, it was over.

The place was almost empty, and cleanup mostly done, as I stood up for the first time in over two hours... my hard-on poking out slightly, as once again I admired Danielle's nylon-clad legs and feet.

"Santa looks like he enjoyed himself," Danielle smiled, gazing directly at my crotch.

"There was a kind lady providing some visual stimulants that I sorely needed to keep me going," I replied, staring directly at her feet. Unfortunately, we were interrupted before she could respond to my rather bold compliment.

"You can go change, Santa," a pretty, chubby redhead offered me. "You're likely all sweaty under there."

"Let's get a picture with our Santa first," Danielle suggested to her, before I could agree to leave.

"Why not?" the pretty redhead agreed.

My cock, which had taken a beating the past two hours, having gotten sacked at least a dozen times, twitched as I sat back down.

Danielle walked over and sat on my left knee. The redhead sat on my right.

"You survived," Danielle said.

"The jury is still out on that," I responded.

"I owe you big time," she said, turning to face the camera.

"You have no idea," I said, before also posing for the camera, both of us seeming to be implying the same thing.

A couple photos were taken, the place was almost a ghost town by now other than a couple of older women heading out, and the photographer who had already packed up before needing to take his camera back out so he could take the last minute photos of us. As the redhead stood up, Danielle asked her, "Can you go back to the dressing room and grab my phone from my purse? No offense, but I want a picture with just Santa and me."

"Sure," the redhead agreed. "We should get one of Mr. and Mrs. Claus for our Facebook page, too.

As the redhead walked away, Danielle raised a sprig of mistletoe over my head and asked, "Do you know what this means?"

"Gawrsh, no, ma'am," I answered, grinning while playing dumb.

"It's the getting-our-toes-wet step of my doing 'anything'," she answered as she leaned in and kissed me.

I kissed her back for just a few seconds, long enough to make it clear this wasn't just some generic mistletoe kiss, before she surprised me once again by placing her hand directly onto my hard cock, "Oh my, this is one big candy cane, Santa. I just hope it doesn't have barber pole stripes."

"Oh wow," I moaned, surprised by her sudden aggressive touch, even though I'd already become pretty confident I could score this beautiful woman if I played my cards right. Apparently, Danielle was ready to place all her cards on the table right away.

"Hard, too," she added, giving it a firm squeeze.

"I thought it might have been broken forever after today," I said.

"It seemed to have stayed pretty hard all evening," she said, "I was monitoring it."

"That was because of your nylon clad feet," I pointed out, figuring since we'd gone this far, I may as well throw my fetish out there once and for all.

"Oh, I've been aware of your nylon fetish since late August," she said, surprising me a bit, as she looked furtively around before doing something that astonished me completely.

She unzipped me, fished out my cock, raised her dress, repositioned herself and lowered herself onto my cock, all in a single fluid motion. It seemed either she hadn't worn any panties today, or she'd removed them sometime during the evening. Either of these possibilities only added to the hotness of her act.

"Ohhh," I groaned, this time with pleasure instead of pain.

"This is just a test run: I need to make sure it still works in case we need it later," she quipped as her pussy engulfed my cock.

"You may need to really work on it to make sure no structural damage was done by those kids," I invited her, getting a rush from this naughty exhibitionistic moment. The redhead could return with Danielle's phone any second!

I'd once had a woman suck me off under a table at a nightclub; In college I'd fucked a reporter in a bathroom at halftime, and I'd banged a coach's wife in a closet at a year-end party... but this joining almost onstage trumped them all.

"Like this?" she asked, as she slowly muscled her pussy around on my cock.

"It's a nice start," I agreed, with a soft moan.

"A very nice start," she moaned, just before the redhead returned.

"Comfortable?" she asked, as Danielle stopped her sly, teasing movements but remained sitting on my lap with my cock inside her, hopefully unbeknownst to her redheaded friend.

"Definitely," Danielle answered, as she leaned back and extended her legs forward, placing her feet on full display for the camera... although it made me moan.

"You two look absolutely adorable," the redhead said perhaps obliviously, perhaps not, as she raised Danielle's phone to take a photo.

"How about this?" Danielle asked, reaching her right hand around my over-padded belly.

"Great," the redhead agreed as she took a couple of photos.

"Or this?" Danielle suggested, turning her body to me, rotating on my cock, so she was looking into my eyes. She leaned in so her lips were just a couple of inches from mine.

"Amazing," the redhead agreed as she stepped around to the side of us, as I thought the exact same word.

"Or this?" Danielle added, draping both her feet over my right thigh, her skirt hiked up high enough that I worried about the particularly intimate portion of our embrace being revealed. I stopped worrying when I considered how hot it would be if we were caught out, and I decided just to relax and go along with wherever Danielle wanted to take this.

"Definitely not Facebook tame, that's pretty sexy," the redhead said, smiling as she seemed to catch on to how amorous we were being.

"A few risqué pictures are permitted for my own slide shows," Danielle said. "I am single again, after all."

"Likely not for long, if you post these," the redhead teased.

"Let me see," Danielle said.

The redhead handed her the phone and asked, "Do you need anything else? I need to get going."

"No, I'll make sure Santa is taken care of," Danielle said, somehow tightening her pussy around my cock without moving anything visible.

"I bet you will," the redhead smiled, taking Danielle's comment the exact same way I did.

"Veronica, I'm shocked you would imply such a scandalous thing," Danielle mock gasped, "I'm just in the giving spirit."

"You appear to be in the getting spirit too," Veronica said, now that I knew her name. And although I had no idea why, I felt her name suited her.