Undercover Mistress Pt. 01

Story Info
The intro to the series. Young man. Mysterious MILF. Feet.
1.4k words
3.72
10.6k
5

Part 1 of the 3 part series

Updated 06/09/2023
Created 10/31/2019
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It all began with a cigarette. My daily route was a balcony at my company's building. I used to smoke a couple of cigarettes per day, chill out, watch the outside traffic wondering about all the things that bugged me, or made me joy, and from time to time had a talk with people that all knew me as I knew them. Smokers. I always had something to talk about and this charisma of mine provided me smiles every day. It's kind of an art to have a small talk and not be intrusive. I had enough reserve to me mysterious, and enough looks to draw attention, so it was like playing a game for me.

There were so many old people there, and a few young. Some of the mature ladies were really pretty. I bet they were smoking hot when they were younger, not that I'm saying that they aren't anymore, but none of them drew my attention. Younger ones were dull. I never got a thought about making some move on them. Maybe it's because older ones were more sophisticated and exotic for me. I never had experience with an older woman, so this was something that I missed out, but I never thought about any of them until I met her. She was new, and she was a bomb. A dream of every kid that jerked off long enough to know what's a good MILF. She was wearing a different clothing combination every day, and every day she had some perverse high heels, inappropriate a bit, like she bought them in some sex shop.

Her legs were thin and ass was bubbly. I wondered if she had silicone tits for quite some time and one day I was sure, she had them. Her makeup was strong, drawn eyebrows, rough face. I suppose she smoked and drained a lot, or she still do. I assumed that by her a bit manly voice. Whiskey it would be. It gave her that touch. The words are a bit scattered, but I must mention some of the pieces to make a better picture. One day, small leather jacket with metal pins, under, some yellow T-shirt without a bra (if you look carefully you would notice), regular Texas pants, but on her ass and legs it looked awesome, really high high heels with covered toes, a black head bandage curled up with some modern hair style, a blonde hair, and that walk that says: I love to fuck!

Time passed and slowly I was having more and more words with her. When she sees me she comes by, we talk, smoke. Months passed. I had a chance to get to know her better. She was married to a guy that was a sportsman and she is now freshly divorced because of misunderstandings, but they stayed in good relations. She is single, have a kid that's already a grown up and studying abroad. Nice. She has some male energy in her. Don't get me wrong, she was 100% smoking hot woman, but she used slang, talked like a man sometimes. That was hot in unique way because I could be more opened in talk with her and not feel like I'm rude or something. She loved to laugh, so I was always trying to make her laugh, every day.

Cigarette became a ritual for me. I don't have to mention that I jerked off a lot thinking about her. That high heels... I had a thing for legs, heels and feet. The time that she wore shoes with toes opened up was the best time for me. She pedicured them often and the nail polish was always perfect. My favorite color was black in combination with mentioned leather jacket. Rockenrolla style. She was asking me about girls. Sometimes we talked about some adventures. She made fun of me because I was honest. I never told some story spiced too much. Usually I lie. A lot. But in this occasion I didn't. Fuck me if I know why.

One day she surprised me with a question. I forgot to tell in the beginning her wonderful name, Aurora, Aury for me.

She asked me: I noticed that you look down a lot when you see me. Do you have a thing for feet?

I was surprised and confused. Blushed, and she was smiling.

She continued: Its ok. Feel free to look. I like my feet. I think they look nice and I try hard to maintain them. I must confess. I like them to be pampered by men. Would you like to give them proper care?

I couldn't believe what I was hearing. She knew all the time perhaps.

I answered finally: I guess. Yes. Of course.

She gave me her number and we had a deal. It was Friday and I would call her when I finish my dinner after work. She invited me to her place for a party, if I can call it like that, a fetish party for me and her. Wow. I always wandered if life gives you this kind of chances to explore. This was the answer. I was excited so much that precum was oozing from my cock all the way back home. My boner was so stiff I could hang an elephant on it. My all time sexual fantasy will be fulfilled with a Playboy cover like MILF. How much cum I spilled fantasizing about something like that? Too much, too damn much.

But, every good thing has a catch. I never thought of that.

To cut the story short a bit. She opened the door of her 7th floor duplex apartment wearing a black latex robe that covered her whole body, haircut with Chinese sticks, a pale makeup that suited her perfectly. Her feet were put in a glass platform high heels. She was wearing black stockings. Her perfume was strong and alluring, and her crib was amazing. Spacey living room, with leather furniture, huge TV, glass table, a lot of big plants, a bar, kitchen, glass wall and behind it balcony with a great view. She was rich for sure. I suppose from her ex. We had a couple of drinks, watched some TV, she all the time in that strange robe. It was like hanging out with a buddy, but with a bulge in the pants. We were dunk a bit. The whiskey was strong and she sipped like we were drinking juice. In one moment we kissed passionately and when I tried to have my hands on her she backed off.

She told me: That's not how things work with me. Now we will go to other room to play and you must listen every word I say, or there will be no playing. Got that?

What could I say?

We entered a room at the same floor. I was stunned. It was a dungeon. Now the pieces were sewed together. She was a Mistress. I must admit that I had fantasies about BDSM, but I wasn't prepared for this. I was scared a bit and aroused so much that I would take up with anything she wants. And I sure did. She unmanteled the robe. Underneath were corset, stockings and garter belts. My brain became a pudding. She ordered me to remove my clothes and stand up in front of her. I quickly did all she wanted and was standing with a stiff cock in front of her. I looked with my heart pumping hard and with a smile on my face.

She told me: We have to improve your attitude. From this moment you will have to answer to my every command with yes mistress, and you will have to do anything I tell you. The smallest mistake, you will be punished. If that doesn't suit you, you know where the door is. Is that understood?

My pudding of brain still worked: Yes Mistress.

She: Spread you legs!

Me: Yes Mistress.

I was standing in front of her with my legs spread for quite some time. She circled around me. Gave her comments about my ass. Told me for how long she wanted to get me to that position, that she knew from the first day she saw me that I would be a perfect sub, that my drooling over her feet was noticeable from a plane, and so many more things. My mind was blown. Standing still was really hard. In a moment I moved my leg and she was pissed. She grabbed a whip and hit me really hard in my guts. The mark was red and bloody a bit. The pain so hard I almost broke my teeth as it kicked in. Wonderful colleague was ruthless behind the curtain. She yelled and I came back to the position. The game continued.

And this story is to be continued shortly...

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AnonymousAnonymousover 4 years ago
Lovely beginning

But ended MUCH too soon.

Waiting for something to happen.

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