My boss ( updated) many new pictures

[paintman990]

mmmmmmmm,she is nice!

[Sheepdawg]

What is your fantasy for this hot ass milf. What would you do to her if you had the chance? I'd love to hear it. Great photos!

Wow...I have so many fantasies about her, you have no idea. But one fantasy I have, is that she one day confronted me when I was taking candids of her. She would ask me why I take pictures of her, and what do I do with them pictures. I would tell her that I'm sorry, but that I couldn't help myself because I think that she is one of the most gorgeous women I've ever seen. And that I feel very much attracted to her...so much that its hard for me to work when she's around. In my fantasy, she would be flattered when she heard me say that. After a couple of days...she would would say " hey listen..I've been thinking a lot of what you said to me. The way you confessed everything for me. No man has ever said anything like that to me before. My boyfriend is such a douche to.me.....and you really seems like a nice guy. I've known you for many years...so....lets go out on a date. What do you say? But don't tell anybody. I dont want people here at work to know. Is that ok? It can be our little secret". I agree. Couple of days later...we start to text each other...and she tells me what I want her to wear on our date. I tell her.. to dress up really nicely because I'm taking her to this really nice and expensive restaurant. I want her to dress elegant. With stiletto heels. I was very specific about her shoes. She tells me why I'm so interested in shoes? And then I confess my fetish for womes shoes and feet. And her mind is blown...she has never ever heard about this kind of fetish before. She's done all kinds of different types of sex, but never have met a guy who's into womens feet. She's interested about this topic and wants to know more.
Anyway, now its Saturday and time for our date. I pick her up in my car. She's wearing this amazing, sexy, tight and revealing blue dress. Nails are done, hair and makeup is perfect. And the heels...wow! She's chosen a pair of black elegant strappy stiletto shoes with a very long and sharp heel. Iam ready to cum inside my pants when I see her but I hold it. I give her a hug and then I open the car door for her. She's happy to see me. And she appreciate that iam being such a gentleman. "You like my shoes? Is this the kind of shoes you wanted to see me in"? she asks me. I said that they look amazing...that I couldn't be more happy. She's pleased that iam so satisfied with her outfit. She also gives me compliments about my clothes as well and she's very friendly.
During dinner, people watch her. Rich old men are staring at her and thinking how the hell is this stunning milf with a guy who is at least 25 years younger than her? They are jealous. I can see it in their eyes. My boss also noticed it,but she's having such a great time with me that she doesn't care about them. We are enjoying each others company and we are both getting more comfortable with eachother. After a couple of glasses of wine, my boss starts to get real flirty with me. She giggles, smiles, and asking me personal questions. She then touches my feet with her heels under the table. And then slowly moves her left foot into my crotch area. She is chocked when she felt that my cock was hard. She quickly removes her foot. "Is everything okay? Did I make you this hard?" She whispers. "Yes...I'm sorry..." I said. "No worries! Oh...you poor man..."she says.
After dinner, when we were walking to my car, she felt guilty about her teasing me when I was so hard. She said that she wanted to make it up to me. So she invited me to her home. We sat down in her sofa, and started kissing. She had her heels on. She hadn't even touched my cock yet, but I told her that I couldn't hold for much longer, that I was about to cum. She was a bit chocked, because we were both fully clothed and we just had kissed eachother. But at the same time she was flattered that I already wanted to cum because of her. "Oh, its alright, dont worry. I understand. Where do you want to cum then?" she asks me. "Is it okay if I cum on your heels and feet? Would that be wierd? Is it okay? " I said.
"You know what, i kind of guessed that you wanted to cum on them. Its totally okay! I know you've been staring at them the whole night. I want you to feel free. Just relax and cum on my shoes. Its totally fine, trust me" She said.
I pulled down my pants, and then I pulled out my rock hard cock. My precum was dripping all over her wooden floor. She just sat there in front of me, watching me and smiling. After a couple of seconds, I ejaculated the biggest load she's ever seen all over her heels. I was moaning so loud. She was chocked and overwhelmed but at the same time impressed. I couldn't stand up anymore, I was exhausted, so I threw myself on the sofa besides her. She just sat there, and was looking at the mess I made. "Wooooow...you know what...I've done a lot of stuff in my life with different men...but this was one of the hottest things I've experienced. And we didn't even have sex?!" She said. I told her that next time I would try my best to not cum so quickly. She was fine with it. She then took her heels off, and my load was dripping down. She got some of my cum on her hand, and licked it up. "Now I know what you taste like" she said smiling. "This was a great experience, didn't see this coming. But it was very different and fun. Thank you so much for everything. If you are free next week, let's do something else then..like...having sex! I'll promise I'll keep my heels on for you. What do you say?" She said. I said I'll be very glad to see her again. Then I went home with the biggest smile on my face.


This is not my boss
..but this is a picture of how I fantasised she would dress like.

[Sheepdawg]

I bet she thinks you are taking pics of her and have a crush as well. How big of a boss is she in that company?

Agree. It's obvious if you see some of my candids! How couldn't she know? I mean, she looked right at me when I was pretending playing games on my phone and smiled!
Maybe she likes the attention she gets from me?
She's she CEO at my job.

[BullAndy]

Simply a good boss

[olallacd]

what a hottie and sexy boss, i love her booty into jeans. You should cum over her face !!!!

[Sheepdawg]

what a hottie and sexy boss, i love her booty into jeans. You should cum over her face !!!!

Glad you liked her! I have cummed to pictures of her face more than I can remember. I'll update soon.

[bill45215]

Awesome

[Sheepdawg]

A little update.

My boss has taken a couple of days off from work. She will be back soon. So Instead of her, we have another boss temporarily. And everybody hates her. Her name is Olga and she's originally from Russia. I've never ever met anyone who is so impolite like her. She's bisexual, changes her haircut more often than I change my underwear, and she hates her job. But..she is quite sexy. Especially when she's not in her work clothes. Here's some pictures of her

[Sheepdawg]

And some from her Facebook

[sh03s]

Did she ever come back?