tagLesbian SexFall of a MILF: A Submissive Tale

Fall of a MILF: A Submissive Tale

bysilkstockingslover©

Summary: A lonely MILF discovers her surprising lesbian side online.

Note 1: Thanks to Tex Beethoven, Robert, David, and Wayne for editing.

FALL OF A MILF: A Submissive Tale

I was home getting dinner started when I heard the front door open, then slam shut. That was all the warning I needed; Hailey hadn't had a good day at school. She barged headlong into the kitchen, slammed her back-pack onto the table in front of her and suddenly ran out of energy. She slumped into a chair, fell forward, burying her face into the bag, and began muttering incoherently against the fabric.

"That good a day, huh, Hailey?" I asked.

She didn't even raise her head to reply, just turned it sideways to gaze up at me miserably, tears welling in her eyes, gave me a fake laugh and replied listlessly, sarcasm dripping in her voice, "Oh yeah, it was just swell."

"You wanna tell me what happened?" I asked, even though it was likely the same as always... some cheerleader or other making Hailey's life a nightmare.

Tears streamed down her face as she blabbered, "The cheerleaders were picking on me again. This time they were mocking my appearance, calling me trellis-face."

Now Hailey was a pretty girl, not with the beauty of a classic model, but more in the girl next door sort of way. Braces were an unfortunate senior year distraction from her lovely smile... when she even had a smile, which hadn't been often since the beginning of the school year.

"Hailey, you know those insults they toss at you are nothing but jealousy. You shouldn't be concerned by a word they say," I suggested, remembering from my own experience that high school could be hell.

"I know, Mom, I try not to care. But the constant teasing and ridicule is exhausting me, and no one stands up for me because they don't want to be targets too," she said, clearly upset. She finally summoned the energy to push herself to an upright sitting position.

I sighed, "I understand honey. I was picked on in high school too."

"You were?" she asked, looking up at me.

"Yes, I was picked on because my chest developed so early," I said, recalling the girls calling me a slut because I had a huge chest.

"Well, unfortunately I didn't inherit that trait," she said, looking down at her own, rather flat, chest, which I thought looked lovely on her ultra-slender body.

"Trust me," I said, "I wish I hadn't. My boobs are much more a burden than a perk."

"How?" she asked.

"They're heavy to carry around all day, which is why I have back problems," I said.

"But all the cheerleaders have big breasts," she said.

"Well, don't worry, they'll be paying for life for that high school popularity privilege," I said, as I moved behind her and gave her a shoulder massage.

"I guess," she said, my predictions of the future not making her present feel any better.

I said, "Look Hailey, you're a beautiful girl inside and out. If these girls are teasing you then it's because they know you're better than they are. They pick on you, trying to increase their own self-esteem. So you shouldn't hate them, you should pity them for being so shallow."

She stood up and nodded, "Yeah, you're right Mom, and you usually are."

"I'm always right," I joked, giving her a big hug, even as I saw the insecurity in her eyes.

.....

The next day, I decided to meet Kim right after school. I would confront these cheerleader bitches and put them in their place. I left my law office early, and reached the school a couple minutes after the final bell.

I sighed, knowing I would have to park a couple blocks away and walk which wasn't a big deal other than that I was in four inch heels and my usual lawyer attire.

As I walked, I could feel the eyes of horny teenage boys checking me out which, I have to admit, I kind of enjoyed. I felt like I'd been single a long time, burying my life in my work and my daughter, after my husband had died of a heart attack at work three years ago.

As I reached the school I saw Hailey waiting near the bus stop, and three cheerleaders, all blonde and gorgeous (so stereotypically cheerleaders it was ridiculous) chatting with her.

Well, 'chatting' would be a charitable description. As I got closer, I could see the one talking to Hailey was slightly taller than her and that Hailey was looking down to avoid eye contact as the blonde literally talked down at her.

I walked faster, wanting to stop this right here and now.

Reaching them, I said, trying to be pleasant, managing not to glare at the blonde bitches, "Hi, Hailey, who are your friends?"

The blonde looked surprised for a brief moment, before she introduced herself, all sweet and genuine all of a sudden, "Hi, I'm Megan and you must be Mrs. Foster."

"I am," I nodded, having kept the 'Mrs.' even though it had been a few years since my husband's untimely passing.

"We were just suggesting your daughter consider joining the cheerleader squad," Megan said, smiling in a way that I knew from my years of experience was as fake as they get.

"Is that so?" I asked, seeing through the fake smile and my tone signalling that.

"Yes, we would love to have her," Megan continued, her smile on full charm.

"Well, I'm sure she will consider it," I said, before turning to my daughter and asking, "Are you ready to go?"

Hailey just nodded and I turned and walked away even as Megan called out, her tone strange, "It was a pleasure to meet you, Heather." I flinched at the unwelcome familiarity of using my first name, but decided not to make a scene.

I turned back, even though I shouldn't have given her the attention, and the blonde waved at me. I maintained polite control and waved back, and once we'd progressed far enough on the sidewalk toward the car I remarked, "She is quite the charmer."

Hailey scoffed, "Yeah, she did ask me to join the team today. To be their towel girl. As you were coming up, she was explaining that a loser like me wouldn't get a better offer from anybody."

"Oh honey," I said, seeing how hurt she was yet again, "Don't let them get to you. They're enjoying their brief time at the top of the food chain, but at the ten year reunion they'll all be fat and married to losers."

"There is no way I'm going to a reunion," Hailey said.

"Oh, you may change your mind when you become a successful lawyer, with a hot husband and adorably cute kids," I joked, even though I knew she hadn't yet decided to follow in my footsteps and study law.

"Maybe I can show up in court to prosecute them and put them all in jail one day," Hailey joked, finally smiling.

"That would be awesome," I laughed as we reached the car. "Do you want to go out for pizza?"

"Sure," she nodded, pizza being her favourite food.

.....

It was two days later, when something, seemingly trivial at first, forever changed my life.

I was at work, just getting ready to shut down my laptop for the day, when I got an email that was entitled MUST READ. I didn't recognize the email address (QueenM), but since our firm had amazing junk protection I assumed it was important. I was also curious by both the name QueenM and the heading.

I clicked on the email and read it.



If you're reading this then your curiosity got the better of you.

'It was weird how she knew that,' I thought to myself before proceeding to read the rest of the message.

I want you to open up a chat (at the link below) and message me so we can talk easily. If you're still curious, and I know you are, you'll message me NOW!!!



QueenM

I reread it twice and for some reason I was curious and it's not like I was busy. Hailey had debate club practice after school and wouldn't be home until six.

So I closed out my email and opened up the chat, had to create a profile which took a couple of minutes (I thought online chat had died when Yahoo changed). Once done, I searched for QueenM and hit enter.



ProudMom: QueenM?

I waited a few minutes, just long enough that I began getting ready to leave when I got a message back.

QueenM: Very good :)

Curious who I was talking to, my first question was obvious.

ProudMom: Who are you?

QueenM: That isn't important. What is important is that you need me. Think of me as your Fairy Godmother.

Already I was intrigued by this person, even as alarm bells went off all over the place.

ProudMom: Fairy Godmother?

QueenM: I want to know if you are bored with your life.

I read her question and pondered it. The question was as simplistic as it comes and yet the answer was as complex as they come.

ProudMom: I'm fine.

QueenM: FINE!!! Fine is the word that never means fine. It means you're bored, or bitter, or lonely... you are in desperate need of a change.

I sighed. The truth was, she was right. My life was boring. Since David had died my life was 100% routine. Get up, work out, shower, make breakfast, chat briefly with Hailey, go to work, come home, make supper, chat with Hailey a bit more, watch some television, read a book, do any work that needed to be done for upcoming cases and go to bed. Christ, I hadn't even bothered to masturbate in a couple of months. I hadn't had sex in over two years and hadn't come from sex since before David died (I had indulged in a single one night stand a year after David died, but guilt had riddled me for so long afterwards I had sworn off men ever since).

Yet, suddenly, I was worried. Who could this be? A co-worker? An ex-client?

ProudMom: How do I know you?

QueenM: You don't. But I know you. You live your life for other people, never for yourself.

That was true. Yet how could she know that? Worried that this conversation was happening at work, as well as with someone I didn't know, I knew I needed to put an end to it.

ProudMom: I have to go.

QueenM: It's alright. I understand. You're scared. That is natural. You are free to continue your boring, humdrum life! Ta ta!

I stared at the words for a couple of minutes... words that sank into me like daggers. It wasn't until the words were thrown at me that I realized the banality of my job.

I was a lawyer, yes.

But I was a corporate lawyer.

And my job was indeed almost always boring.

I should have closed the chat and headed home, but I didn't.

ProudMom: How do you know I have a humdrum life?

I waited a couple minutes, just staring at the screen waiting for a response.

QueenM: 99% of women have a humdrum life. They have a boring job, they live with a man they used to love, they have sex once a month, and they either reminisce about when they were young and carefree, or they bury their lives in their work and children... never really living for themselves.

A chill went up my spine. She had nailed me precisely, other than the husband part, which wasn't true. When he was alive our sex life was still very passionate. He knew my needs and desires. He knew that at work I was a no-nonsense lawyer who was always in charge and had to be very assertive in a still mainly boys' club.

Yet in the bedroom, I wanted him to be in charge. I liked being used as a slut... I craved being called names and fucked hard and rough.

My panties dampened as I reminisced about David treating me like a complete slut just a couple days before he died. That day he'd made me wear a schoolgirl uniform and he played the teacher. He fucked my face while holding both pigtails, he then bent me over my desk and pounded my ass while talking dirty to me.

I came three times.

I hadn't come from sex since.

ProudMom: And how do you know this?

QueenM: Psychology class and experience.

ProudMom: How old are you?

QueenM: 18

Oh, God. I was talking to someone the same age as my daughter.

QueenM: But I'm wise beyond my years.

ProudMom: Why did you email me?

QueemM: Fate.

What a strange answer.

ProudMom: Fate???

QueenM: I just typed an email address in randomly and sent the message.

No way? This is all a coincidence?



ProudMom: Really?

QueenM: I don't even know where you live.



ProudMom: Where do you live?

QueenM: Canada.

I lived in Boston.

QueenM: So... are you bored with the same thing day in and day out?

If you would have asked me fifteen minutes ago I would have said no.

Yet somehow, this weird conversation with a complete stranger was stirring my thoughts in areas I never thought about, had me questioning that.

ProudMom: Well, I never really thought about it but I kinda am.

I was wondering where this was going.

QueenM: Well, my dear, that's why I'm here. I'd like to fix that and help make your everyday life fun again.

Having an 18-year-old calling me 'dear' was strange.

Having an 18-year-old complete stranger tell me she could make my life fun again was even stranger.

Curiosity getting the better part of me again, I responded.

ProudMom: How would you do that?

QueenM: It's quite simple. I'll give you daily tasks to do and if you complete them I'll give you a reward. If you fail, you'll be punished.

Now after that message I knew I should have clicked the exit button. Yet, I hadn't been punished since before David died. He'd always loved to push my limits... a butt plug in a court room, a vibrating egg at a Christmas party, coating my face with cum and making me parade it around in public when we were in Europe. Each of these were humiliating, yet doubly stimulating and eventually built to my most intense climaxes.

ProudMom: You have me curious.

QueenM: I know I do.

ProudMom: So what kind of punishments?

QueenM: Interesting you ask that first.

ProudMom: I like to know what I'm getting myself into.

QueenM: Intense orgasms... if you're a good girl. Intense orgasms in public if you're bad.

I froze. The innuendo had been there.... But there it was... out in the open. I was having a sexual conversation with an 18-year-old.

Even though my pussy was leaking slightly in my panties and this was the most excited I'd been sexually since before David died, I knew I had to end this now.

ProudMom: I need to go now.

QueenM: This is a one-time offer. If you're interested, which we both know you are, I expect to see you online at 9 o'clock your time. THIS IS AN ORDER! If not, I'll find another lonely housewife to give my attention to.

Before I could respond she signed out.

My head was spinning and being horny, I closed my eyes and slid my fingers inside my panties.

In a couple of minutes I came... hard.

Once I recovered, I shook my head. Shit, I really needed to get laid.

No longer horny, I told myself I had no intention of ever going back online.

That night, I asked my daughter, "So how was your day?"

"Strange," Hailey answered.

"How so?" I asked, thinking it couldn't be as strange as mine.

"Megan complimented me," she said.

"How?"

"Said she liked my skirt and told me she was impressed that I put in the effort to wear pantyhose."

"That is weird," I said, even though I had always promoted wearing hosiery. For Hailey I suggested sheer pantyhose as they were soft, sexy and showcased her legs... while also disguising how pale her skin was... like me she didn't tan, she burned. I, on the other hand, wore only thigh high stockings or a garter-belt and stockings for a couple of reasons: David had had a silk stocking fetish and insisted my cunt always be easily accessible (his words) and I loved the secret rebellion that underneath my conservative business woman attire I was dressed sexy in lacy bras, thongs and thigh high stockings. I didn't even own anything you could call sensible underwear.

"I know," she nodded. "She and the other cheerleaders were super nice."

"Maybe they finally saw the real you."

"Maybe," she shrugged, clearly not convinced.

"Well, today was a good day, then," I said.

We had dinner, talked about the debate tournament she was competing in in a couple of weeks and chatted about different colleges and which ones she was leaning towards for next fall.

It was weird that in a few months I would be utterly alone.

I felt depressed.

For the next couple hours I pondered my future... alone. Hailey was definitely going to a school far from home on a full scholarship. Academically she was assured of a very bright future.

Soon I would be home alone.

Suddenly, the strange and surreal chat session with a stranger from Canada intrigued me. Suddenly it was something that I could hold on to once Hailey was gone.

It was a few minutes before nine when I grabbed my laptop and logged in.

ProudMom: Hi.

I waited for fifteen minutes, watching the end of The Goldbergs and reminiscing about the eighties when life was so much easier.

Finally she responded.

QueenM: Sorry I was late... I was training a new pet.

A new 'pet'. The term sent a chill up my spine.

ProudMom: Oh.

QueenM: I knew you would make it.

ProudMom: That makes one of us.

QueenM: Why did you choose to?

ProudMom: I don't know.

QueenM: That is not a real answer.



ProudMom: Curiosity.

QueenM: What are u curious about?

ProudMom: U!!!

QueenM: Well every time you obey a task I will answer one question you have.

ProudMom: What kind of tasks?

QueenM: Oh, a wide range.



ProudMom: Like?

QueenM: First off, I want you to describe yourself to me.

I thought about lying, but I had the feeling she'd know I was lying to her... somehow.

ProudMom: I'm 5'5", blue eyes, red hair, I usually wear it up, but when down it reaches to the center of my back.

QueenM: Mmmmm, you sound pretty hot.

All of a sudden I was blushing. It had been years, back when my husband was alive, since I'd been complimented like that (although that was partly my fault as I avoided any sort of intimacy, even in conversation). It took me a while to realize she'd sent another message.

QueenM: You didn't tell me your cup size.

I didn't feel comfortable telling her that, but then she added....

QueenM: I know you might not wanna tell me, but if you obey I'll reward you for being a good girl.

As I read the words I felt a little surge of electricity go through me and the reward had me super curious as I remembered, and even became the submissive I used to be... something I had controlled and ignored the past couple of years.

Figuring talking to a girl in another country was a rather casual way to pull myself back into my submissive past I figured why not answer.



ProudMom: I'm a 30E.

QueenM: You're shitting me!

I smiled. My breasts had always been an asset. Although the last couple years I had hidden their size with my choice of business outerwear.

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