tagLesbian SexLesbian Seduction: A Stockings Tale

Lesbian Seduction: A Stockings Tale


Summary: A lonely bi-curious MILF falls for an on-line teen Mistress.

Note 1: This is a long story...so patience is a virtue.

Note 2: This story is also an ode to one of my favourite fetishes, well okay definitely my favourite fetish, silk stockings.

Note 3: This story is dedicated to Maureen who suggested the idea, is also a stocking lover, and is the main MILF in this lengthy ode to nylons, lesbian submission, and coming to grips with who you are.

Thanks to goamz86, Robert and Wayne for editing this lengthy story.

Lesbian Seduction: A Stockings Tale


Loneliness set in almost immediately. Maureen had been a single mother for the past fourteen years (after her husband left) and used to a king-sized bed with only her in it, but with her daughter, after having taken a year off after high school to work, going to university three hours away, she was utterly alone for the first time in over twenty years.

At forty-nine, all she had was her job as a lawyer at a mid-sized firm where she essentially did wills, estates work and some court work in that area. Like her home life, it was mundane.

Maureen had had a couple brief lesbian rendezvous while at conferences using Craigslist, but she always felt ashamed after for submitting to her sexual desires with complete strangers. Yet, she also yearned for the feelings of submitting to powerful women who understood her desire to be submissive in the bedroom...a complete polar opposite to her career persona.

At forty-nine, Maureen was still very attractive, having never lost her figure. She was tall at 5'9", with long legs, small 34B breasts, shoulder length flaming red hair and green eyes.

Maureen was also old school in her fashion sense. She always dressed in classy dresses, or skirts just above the knee and always wore sexy lingerie that unfortunately, almost no one ever saw, underneath. She only wore stockings, usually with a suspender belt, loving the idea that underneath her conservative, no-nonsense exterior was a sexy woman dying to be discovered. Her fetish for stockings was actually a point of pride as she hated when she went to weddings and saw the bridesmaids or, worse yet, the bride, bare-legged. The same went for funerals and formal events where nylons were, to her, the epitome of class and style. She thought 'what's the point of even coming if you were too lazy to finish off the outfit.'

Maureen's idol was the Duchess of Cambridge. There is a woman who knows how to dress and it is not just money and a great body. No, it's the willingness to make the effort. Kate had it all: looks, brains and fashion sense. As the fashion icon Helena Rubinstein once said "There are no ugly women, just lazy ones".

After reading a few stories online one night, she came across one that had online chat. Curious, she went online, created an account, and started chatting. After a couple of hours, with a few chats running simultaneously, she really got drawn into one chat with a younger girl. Her username was silkstockings18. Maureen, who had created the username milflezinnylons, was instantly intrigued.

Milflezinnylons: Hi, I like your user name.

Milflezinnylons: I'm 49, lawyer

Silkstockings18: I'm 18, high school student

Maureen was instantly worried about chatting with someone so young, but she was eighteen, which made her legal, and it was, after all, just online chat.

Milflezinnylons: nice to meet u

Silkstockings18: u too.

Milflezinnylons: do u really like wearing silk stockings?

Silkstockings18: yes!

Milflezinnylons: that is rare for a teenager

Silkstockings18: I know...but I wear them almost every day

Milflezinnylons: me too

Silkstockings18: at work?

Milflezinnylons: yes

Silkstockings18: pantyhose?

Milflezinnylons: never...usually silk stockings and a suspender belt

Silkstockings18: nice! I always wear thigh highs

Milflezinnylons: double nice!

Maureen couldn't believe there was a young lady who had the same fetish as she had.

Silkstockings18: are u wearing stockings now?

Milflezinnylons: no

Silkstockings18: why not?

Milflezinnylons: are u?

Silkstockings18: of course

Milflezinnylons: I just had a bath after a long day of work and got in my pajamas

Silkstockings18: I see

Maureen felt an instant connection with this young stranger and wanted to make her happy.

Milflezinnylons: I can put some on if u would like me to

Maureen instantly realized how submissive her last sentence was and shook her head at how easily she was getting drawn in to a girl (hopefully she was really a girl) on the internet that she knew absolutely nothing about.

Silkstockings18: u would do that for me?

Milflezinnylons: yes

Silkstockings18: please do then

The young eighteen year old senior already had a few online submissives...but somehow this one seemed different. She was intrigued by her and planned on slowly getting to know her better.

Milflezinnylons: brb

Maureen could have faked it, but she didn't like lying, even to an online stranger, plus getting slightly horny, even though the conversation had been very tame, she felt the need to put some on. She grabbed a garter and black stockings and rolled them on her legs, but kept her pajama top on.

Milflezinnylons: back

Silkstockings18: what colour

Milflezinnylons: black

Silkstockings18: nice choice

Milflezinnylons: u?

Silkstockings18: dark brown

Milflezinnylons: very nice

Silkstockings18: are u married?

Milflezinnylons: long divorced

Silkstockings18: kids?

Milflezinnylons: a 20 year old

Silkstockings18: b or g

Milflezinnylons: girl

Silkstockings18: does she like wearing nylons too?

Milflezinnylons: sadly, no

Silkstockings18: not like mother, like daughter

Milflezinnylons: today's generation is too lazy to put together a complete ensemble

Silkstockings18: I know if you're not going to put the effort to dress up completely, don't bother

Milflezinnylons: I say the same thing

Maureen couldn't believe how much she had in common with this complete stranger.

Silkstockings18: There are no ugly women, just lazy ones

Maureen couldn't believe the quote she always used was being quoted to her

Milflezinnylons: I use that exact quote with my friends

The teen smiled. She was quoting a neighbour across the street who she had heard saying it at a bridal shower a couple of months back and had used it ever since in her seductions of older women.

Silkstockings18: no way!

Milflezinnylons: u r like my doppelganger, just much younger

Silkstockings18: I'm flattered

Milflezinnylons: I'm the one who's flattered

Silkstockings18: sandalfoot or reinforced toe?

Milflezinnylons: sandalfoot of course, otherwise the toes aren't perfectly showcased

Silkstockings18: agreed...are your toenails painted?

Milflezinnylons: always

Silkstockings18: colour choice?

Milflezinnylons: varies...red usually, but purple on occasion, or pink, blue or green

Silkstockings18: interesting

Milflezinnylons: it is?

Silkstockings18: sure...u accessorize ur feet

Milflezinnylons: I guess I do

Silkstockings18: I often have two colours...like red and black (our school colours)

Milflezinnylons: my daughter's colours were red and black too back in high school

Silkstockings18: what a coincidence

Milflezinnylons: small world

Silkstockings18: I've enjoyed our talk and would love to chat more, but unfortunately, I need to go to bed...school in the morning

The teen wanted to leave the older woman wanting more...knowing that if she was submissive, as she assumed she was...she would eagerly come back online to chat with her.

Milflezinnylons: I should too

Silkstockings18: it was great chatting with u

Milflezinnylons: u too

Silkstockings18: good night

Milflezinnylons: I hope to chat with u again soon

The teen decided to give just a hint of her dominant side by giving a small order.

Silkstockings18: me too, but u better be wearing nylons

Milflezinnylons: yes, Miss

Silkstockings18: hmmm...Miss I like that

She meant it as a joke...but after it was out there, Maureen hoped it was enough of a dangling carrot for her to return to chat again soon.

Milflezinnylons: <blush>

Silkstockings18: sweet dreams

Milflezinnylons: ohh, I will

Maureen again giving subtle sexual hints.

When the young girl, whose name she hadn't even asked for, didn't respond again, Maureen logged out, pulled up a Literotica story, one of her favourites, Suburban Submission, and fingered herself to a quick orgasm imagining this stranger taking her...even though she had no idea what she looked like.

The teen, meanwhile, pondered the possibilities of this new potential online sub. Although she couldn't be sure she was a submissive, she just sensed she was and also sensed she would be easy prey.


The next day after work, Maureen poured herself a glass of wine, stayed in her garter and stockings, and immediately went online, hoping the teenager was online, yesterday's brief chat on her mind all day long at work.

Milflezinnylons: hi

Unfortunately, the teen either wasn't online or was busy as she didn't respond. Maureen instead read a few forums about finding an online Mistress. The idea was a big turn on for Maureen and she wondered if silkstockings18 was a Mistress. A couple responses hinted she may be, but there was definitely nothing conclusive.

Meanwhile, the teenager saw the message and smiled...she is eager. Knowing how to play the game, she ignored the chat response while she finished her homework.

Disappointed, Maureen ordered food for delivery and was just finishing eating her Chinese food and half done her second glass of wine when she got a response.

Silkstockings18: hi back

Maureen felt a tingle down below...an odd excitement considering the response was completely generic.

Milflezinnylons: how was your day?

Silkstockings18: boring...as high school usually is

Milflezinnylons: lol

Silkstockings18: how was your day?

Milflezinnylons: boring too...

Silkstockings18: u didn't put anyone in jail today?

Milflezinnylons: I'm not that kind of lawyer...I do wills and estates and stuff

Silkstockings18: I c...so tell me about yourself...what do u look like?

Milflezinnylons: I'm 49, but look much younger I am told; I have green eyes and red hair...my Scottish ancestry dominating

Silkstockings18: I'm Norwegian

Milflezinnylons: so blonde hair and blue eyes?

Silkstockings18: I fit that stereotype completely yep

Milflezinnylons: thin too I imagine

Maureen was trying to picture this intriguing teen.

Silkstockings18: I suppose...breast size?

The teen finally asked a question that shifted from generic to slightly more personal.

Milflezinnylons: 34b...my breasts are rather small...but still firm for my age!

Silkstockings18: I have 36c and sometimes wish mine were smaller...

Milflezinnylons: I've always wished mine were bigger

Silkstockings18: everyone always wants what they don't have

Milflezinnylons: so true!!

Silkstockings18: shoes...open toe or closed toe

Milflezinnylons: open of course...I need to showcase my toe accessory...LOL!!

Silkstockings18: cool...how did u begin ur fetish for nylons

Milflezinnylons: it's a long story

Silkstockings18: I have time

Milflezinnylons: my mom was very strict, very Christian, so make-up and lingerie were always practical and nothing too fancy. I first got interested in more feminine styles of lingerie, stockings, heels etc. as a babysitter. I babysat a lot in my neighbourhood. One dull night after the kids went to bed, I was putting away some laundry, and there in the master bedroom was a copy of Penthouse magazine - considered pretty risqué at the time. I was looking at the pictures of some of the models and thought that the lingerie they were wearing was sexy and very attractive. Curious, I decided to see what the lady of the house had in her drawers and closet. I found a suspender belt, some nylons that had been worn before, and a bra. They were a lovely pastel pink, and I tried them on. Now I never did fill the bra cups very well, and still would not, but god I loved the look.

Silkstockings18: u bad girl

The teen already had ideas for how to push the submissive if it went that far.

Milflezinnylons: I was a good teen, a somewhat bad college girl and then a loyal wife

Silkstockings18: now?

Milflezinnylons: I am looking to be a bad girl again

Silkstockings18: I'd love to know more about ur bad girl fantasies, but my parents are calling me

Maureen kept forgetting she was in high school and felt slightly guilty chatting so freely with a teenager.

Milflezinnylons: no problem, I should give my daughter a call

Silkstockings18: have a good evening

Milflezinnylons: u too

Like the night before, Maureen ended up pleasuring herself, fantasizing about submitting to the young teenager.

She also went on Craigslist and searched ads for Boston, where she would be in three weeks. Her desire for another evening of no strings attached sex was growing and she wasn't even sure she could wait three weeks. She left messages to a few ads and went to bed.


The next day was crazy and it was almost nine by the time Maureen got online. Unfortunately, the teen didn't respond to her message and Maureen was so horny she ended searching Craigslist in her own city. A few ads were intriguing and she almost replied to a couple, but resisted, the thought of somehow getting caught by someone she knew or worked with, no matter how miniscule, overriding her desire.

Instead for the third straight night she ended up getting herself off with her fingers.

The next day, she got home around dinnertime and as she made herself something to eat, she brought her laptop downstairs and logged in. To her surprise, there was a message from the teen.

Silkstockings18: sorry I missed u last night...I'll be on around 7 tonight.

Maureen looked at the clock. She had almost two hours until then. Thus, she made supper, watched the TV news and had a shower. Sitting on the couch, to watch television and simultaneously chat, she was only in a robe and thigh high stockings...sans either a bra or panties. Trying not to appear too eager, she waited until ten after seven before logging in.

Milflezinnylons: Hi

Silkstockings18: Hi, sexy

Being called 'sexy' by a teenager made Maureen blush, even if it was generic considering the teen had no real idea, other than her earlier description, of what she looked like.

Milflezinnylons: Right back at u

Silkstockings18: So tell me something you have never told anyone

The sentence threw Maureen. After a brief consideration she answered.

Milflezinnylons: I read craigslist ads in hopes of meeting someone

Silkstockings18: romance or casual encounters?

Milflezinnylons: <blush>

Silkstockings18: have u ever used it?

Milflezinnylons: while out of town

Silkstockings18: never at home?

Milflezinnylons: too close for comfort

Silkstockings18: fair enough...hobbies?

Milflezinnylons: work

Silkstockings18: u r not a work first woman r u?

Milflezinnylons: since my daughter went to college I sure have been

Silkstockings18: hmmmm...we may have to change that

Maureen was intrigued by the sentence.


Silkstockings18: Out of curiosity, why did u contact me?

Milflezinnylons: your username intrigued me

Silkstockings18: that's it?

The teen would never start being the aggressor, she wanted her pet-to-be to willingly give in to her.

Maureen, meanwhile, decided to be frank with the stranger...anonymity making such honesty easier.

Milflezinnylons: well, truth be told, I have become somewhat lost

Silkstockings18: how so?

Milflezinnylons: since my husband left, I have focused on work and my daughter, but now that she is gone I am lost...I have been living for others for so long I don't know who I am

Maureen stared at her words...sadly that was her life in a nutshell...a life that didn't include her needs.

The teen smiled at the honest declaration. As expected, this women was desperately looking for some guidance.

Silkstockings18: and what are u looking for?

Milflezinnylons: honestly? I'm not sure...

Silkstockings18: can I ask u a frank question?

Milflezinnylons: of course

Maureen somehow trusted this stranger with her complex feelings; plus, this was the internet, which made her expressing her true feelings feel safe and somewhat therapeutic.

Silkstockings18: when did u last have sex?

Milflezinnylons: 3 months ago at a conference

Silkstockings18: man or woman?

Deciding to be completely frank with the intriguing young woman she answered honestly.

Milflezinnylons: woman...I have lost faith in the male species

Silkstockings18: and u have been with a lot of women?

Milflezinnylons: just 2, both one time each, using craigslist

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