Mystery Texter

Mystery Texter

Summary: Teacher receives a surprise invitation for a night of wild sex.

Note 1: This is a Valentine's 2023 Contest Story.

Note 2: Thanks to NylonKitten for generously allowing me to use her photos for this story, as well as for a previous story called Jasmine Fantasies: Nylon Seduction. She is a complete beauty, and if you are not following her on Twitter, Instagram or other online platforms, then shame on you. Also, the story is a showcase of the amazing NylonKitten and a foot fetish fan's dream... I hope.

Note 3: Also, thanks to a stud who wants to remain anonymous, for the use of a couple of impressive crotch pictures.

Note 4: Thanks to Tex Beethoven for editing, as always.

A text from a number I didn't recognize popped up while I was taking my lunch break: What are you doing for dinner tonight?

I responded, curious to know who this was, and assuming it was a wrong number: I think you have the wrong number. Who are you looking for?

The response came back quickly: Is this Dean?

I was surprised. This was for me. Unlikely the accident was the wrong Dean, which seemed much less likely. I responded: Yeah, it is.

She responded, I assumed it was a she: The Dean who teaches American history?

Definitely not being mistaken for someone else. I responded: That is definitely me.

She texted: So are you free tonight?

I responded, this mystery becoming a little intriguing and a little cloak-and-dagger-ish, since I still didn't know who my correspondent was: On Valentine's Day?

She responded: Yes. I know you have wanted me for some time. A change in my circumstances has made that remote possibility into an imminent reality, if you haven't changed your mind.

Now I was super curious... but also slightly worried this might be some student trying to hoodwink me, which could easily get me into some major trouble.

I was a pretty good-looking guy, a teacher at a private secondary school, and some of the girls were often quite brazen about communicating what they would like to do to me. It was flattering... and occasionally tempting... but I loved my job, and I didn't want to be sued by some rich daddy, or to get blackballed from my teaching career. Plus, teenage girls might look like utter temptresses, but they lacked the true sexuality a man like myself was looking for... since I preferred older women. I was far more likely to fuck a student's Mom than the student herself. In truth, at a previous school, that had happened twice. Once with a woman who was divorced, and although I'm not overly proud of my actions, with another woman who was allegedly happily married with three kids... allegedly happily, since for three months she regularly came to my apartment to suck my cock and to take it in the ass... in her mind it wasn't cheating if I didn't fuck her pussy. Strange, but true.

I responded: Who is this?

She responded: I want that to be a surprise for now, but I know what makes your dick hard.

What the fuck? This was surreal. If this was a student, I had to end this dialogue right now. So instead of responding, even while my dick was getting hard, I waited to see if she'd give me any more info.

It was a few minutes later when she did. Knowing you, you are worried I'm a student. I promise I am not. But I do know some of your fantasies.

What the fuck?

This was getting complicated! A mystery of a surreal nature.

I responded: And I know you?

She responded: You used to.

Someone from my past?

These clues were not helping me to make any headway towards solving this mystery... which by now had gotten my dick hard.

I asked: Did we date?

She responded: Sadly, no. I was married, and you had a serious girlfriend.

This newest clue only added more complexity... thus widening the scope of the puzzle, instead of narrowing it down at all.

I asked, recalling her earlier mention of knowing what made my dick hard: Then what do you think turns me on?

Instead of her responding with words, a picture popped up a moment later. It showed a pair of nylon-clad feet, in bright red heels, with purple painted toenails subtly visible through her stockings. It was also outdoors, but since the scenery hinted at someone's garden, it could be anywhere. But on the other hand, if this person was inviting me to dinner, it would need to be somewhere local.

Did she think it was heels that turned me on, or the nylon-covered feet... since one of those choices was spot on.

Then another picture arrived, this time with words: Although I would wager you prefer this image.

Oh my God... long legs in shining... almost glowing... pantyhose!

Instantly my cock ached.

Yep, whoever this was knew my kryptonite. One of the reasons I admired older women... they tended to wear nylons and lingerie, and they put some effort into their appearance, in more ways than just throwing on some slutty attire.

Sheer nylons!

Feet, especially!

She asked, as I stared at the perfectly manicured toes: Am I right, or am I right?

I responded, curious how she knew that: How could you know that?

She responded: Does it matter? Or do you prefer this shot instead?

Another photo popped up, tantalizing me with a long pair of legs clad in nylons.

Sexy, shiny nylons, that were usually worn only by celebrities or porn stars, yet they were so fucking sexy!

I responded, trying to place these legs. It was obvious she knew me, therefore I must know her: Great legs!

Her response: Only great?

I quickly replied: Fantastic! Amazing! Cock hardening!

I pressed Send, and then realized what I'd just said. I quickly attempted some damage control for my third exclamation: Please ignore the last crude response.

She responded: Why should I? Didn't the sight of my legs in those stockings make your cock hard?

Shit! Who was this? So fucking sexy! Wears nylons. Has a wicked tongue. She seemed too good to be true.

I responded, yet continued keeping my responses conservative, in case the wrong person intercepted this exchange: I certainly didn't intend to say anything like that.

Her response: Then what did you intend to say?

Shit. She was pushing me to come right out into the open!

By now confident this wasn't some sort of student prank or someone trying to get me fired, I responded frankly this time, my hard cock doing all my thinking anyway: Yes, these pictures of your legs have made me really hard!

She responded: I bet you have a big cock.

My eyes went wide.

Before I could respond, she sent another photo with the words: Although I know what really turns you on is nylon clad feet. Am I right, Dean?

Shit! Shit! Shit!

The soles of a nylon-clad foot always drove me wild.

As did a woman's toes, especially painted, all decked out in sheer nylons.

But how the fuck would this woman know that?

I asked: How do you know the nuances of what I do and don't like?

She responded: I'm very observant. Here are some Valentine's Day colours for you.

As I admired... or more accurately, drooled over her pink soles... imagining myself licking them... massaging them... fucking them... another photo arrived, with another message: Or perhaps you're in the mood for black.

This time she was showing me more of herself... and I could see some of her long hair... that looked red... or perhaps brownish red.

But who was she???

I responded, trying to be casual, but mainly to solicit even more photos: Actually if you must know, I prefer mocha or beige nylons.

She responded immediately with three pictures in a row, as if she'd anticipated my response. So like this?

Or this?

Was she a brunette?

Or how about this?

Now she was a blonde?

My head was spinning.

Who was she?

I couldn't place her... except she also seemed vaguely familiar.

Was she a substitute teacher?

The Mom of a student from my past?

And fuck... check out that ass!

I now responded with all my lust hanging out: First, wow, just wow! Second, exactly what I like! Third, what a great ass! And fourth, wow, just wow!

She responded a moment later: Thank you, you are very kind. But you never confirmed or denied my very important assumption.

I asked: What assumption?

She responded generously, with yet another picture: Do you have a big dick?

I pondered my response. I did indeed have a big dick. Eight inches. In fact, some women found me too big. I knew I wasn't some porn star horse cock, but I also knew I was substantially bigger than the average man, and from personal experience, I knew my equipment was greatly appreciated, and sometimes even revered by older women.

I responded while I continued trying to place this woman... as she kept showing me a bit more and more of her body and face: I'm told I am quite well endowed.

She responded: I bet you are. Any chance of a sneak peek? You wearing just boxers, perhaps. Here is what I will be doing tonight if you don't agree to go out for dinner, then maybe a movie, perhaps followed by some one-on-one fun. In case it needs saying, I am no longer married, and I'm reasonably certain you're not currently in a relationship. Although that latter might change tonight.

Jesus!

She had been pretty forward and brazen since the first photo... but this was really getting wild.

I responded: Well, I am bigger than that. Although I don't vibrate. : )

I then rummaged around in my phone and pulled up a photo I had used on occasion when chatting with women online. It was a pretty safe picture, and certainly anonymous, but it also outlined my impressive package pretty clearly.

She responded a moment later: Shit, I knew you would have a big fucking cock. Now we have to meet tonight. Recognize me yet?

Fuck! Who was this?

And in spite of her disclaimer, that was a wedding ring on her finger.

Although who knew how old these photos were?

I responded: I know I should know you, but I don't... yet. But I have to go and teach... although I'm not sure I can move away from my desk without attracting some unfortunate attention.

She asked: Have you figured out who I am yet? Here is one more tease.

I responded, my mouth watering: Sadly, no... but I can't imagine not remembering you!!!

She responded: I was saving this one for last. The perfect colour for you. The perfect pose. And... I imagine enough of my face for you to recognize me.

As the bell rang... I stared at the photo.

It was Mrs. Ferguson!

My Mom ran a bridal shoppe (yes, that's how she insisted on spelling it), and Mrs. Ferguson was her accountant!

The woman I always drooled over at Christmas parties, had jerked off to many times....

Oh my God!

I responded: I'll text you right after my next two classes, Mrs. Ferguson.

She responded: It's Emma, and I'm not Mrs. anyone anymore. This is the face I hope to be making tonight when you're balls deep inside my pussy.

Kids started streaming into my classroom while I gawked at the provocative picture and her blunt, promising words. I wanted to respond, but I needed to calm down and put my phone away. I'd designated my classroom as a no cellphone zone whenever class was in session, and that rule applied to me too.

As I did, I processed that my Mom's ex-accountant... she'd gotten divorced and decided to open her own accounting firm, if I recalled correctly... clearly wanted to fuck me.

I tried to focus on my students during the next two hours, but it was hard... pun not intended...

It wasn't until the end of the day, two excruciating classes later, that I checked my phone and saw that she'd sent a few more pics.

With the first one she asked: Do you think I could pass as a teacher?

Next one: Or perhaps as one of your students you need to keep after school for some one-on-one tutoring?

Another hot pic: Do you like stockings with seams?

They just kept coming: Or do you prefer sexy lingerie with white stockings?

Yet another wicked one: Or do you want a Mommy Mistress to teach her bad boy who got too full of himself... wink wink... a lesson?

My hard cock was aching again.

Then as I was scrolling through all these pictures for a second time, another new one arrived: What would you do to me in this position?

Jesus!

I responded, deciding just to be blunt, since she certainly wasn't beating around the bush... except perhaps literally... Sorry, my classes for the day just ended, so I was scrolling through all your teasing pics. I would suck all ten of your toes one by one, lick the sweet sweat off of your soles, grab your ankles, spread your legs, and I'd eat your pussy through your pantyhose. Then I'd rip them open at the crotch, and fuck the shit out of you.

She responded: These soles? I have been wearing these stockings all day!!!

She added: P.S. I will hold you to every word you just said. I have booked The Deep Dive for 5:30. I expect to see you there. Dress shirt, jacket, tie and slacks. Be prompt.

I replied, definitely not rejecting her life-changing offer: Dressy it is. I will be there. Promptly at 5:30. Which meant I needed to get a move on... it was already 4:00. Fortunately, I didn't live very far from the high school.

She responded: Show me your hard cock in your underwear right now.

I responded, rubbing my cock under my desk: You want to see what you are doing to me?

She answered, as always with another picture of temptation: Yes, I want to see your big, fat cock all hard because of me. P.S. If you play your cards right, you may find yourself shoving that big cock inside all three of my holes.

Fuck! Fuck! Fuck yeah!

I responded, as I went and locked my classroom door: I don't think you could handle my fat cock in that sexy ass of yours.

She responded: I'll be your submissive slut tonight Dean, so that will be your call. Have you ever wanted to have your own personal older woman fuck toy who will fawn all over you and do anything you want?

As I got back to my desk, I responded: Jesus, Emma! I may come in my pants right here at my desk!

She responded: Please save that big load for me, Master. Maybe a sexy foot job?

I pulled my pants down to my knees and quickly took an up-close and personal photo of my raging hard-on in my boxers. I then sent it: If you keep sending me pics, I don't know if I can last.

She responded: Mmmmmm, fuck, do I want that cock. You've got my nipples hard!!! See?