Bosslady85

The best part of my day was when she'd leave the office. Not that I wanted to see her go, but that was the only time I was afforded a glimpse of her as she'd make her way down from the 30th floor and past my security desk. I saw plenty of executives every day, but something about her was different. She exuded power, from her always-neat pixie cut to the outfits that showed off her toned arms and calves. Surely, she could have any man she wanted, and on her terms.

So imagine my surprise when I came across a dead ringer for her on an adult dating website, right down to the username: bosslady85. Nah, couldn't be her. Still, the resemblance... the next day, I took note of the beauty mark on her left cheek and checked the site again... wow, it was her, alright. So now I'm ogling her in person AND online.

After a few too many scotches on a dull evening, I decided to hit her up. Would I tell her who I was at first? I asked myself far too many questions that didn't need to be answered as she didn't respond anyway. Of course, imagine how many messages a woman who looks like that must get on a weekly or even daily basis. The light of day revealed the silliness of my attempt, and I continued my role as a spectator, trying my best not to cross the line into stalker territory.

I'd all but forgotten about trying to contact her when one day I see a comment from her on one of my posts, complimenting my writing. I try to contain my excitement and thank her like a normal, non-infatuated adult, making note that the story leans heavily toward female submission.

Some time goes by, a few more stories, a few more comments, and I decide to try her again. This time she responds. We get to know each other a little, but as I explore any sort of d/s themes, she shuts me down. "I love your words, but I could never give up that kind of control." We continue our correspondence, but she still never looks my way when she walks past my desk. I'm not wearing my uniform in my pics, but it's still clearly me. My heart races even more than before each day she leaves. Waiting for the day she turns her head in my direction and the jig (if that's what you can call it) is up.

I begin to write all my stories with her in mind, some I post and some I send just to her. She admits to touching herself while she reads my words. She says it's as if I'm reading her mind and showing her fantasies she never knew she had.

She sends me some private photos and when I volunteer to reciprocate, she declines, then explains: She likes the idea of not knowing for sure if she'd recognize me in person, calls me her Mystery Man. She likes the thought of being watched.

"I didn't think you liked the idea of giving up control," I reply.

"I don't."

"Some might associate voyeurism with submission."

She follows with a simple "hmm" that makes me back off but also helps me realize the seed has been planted.

As more time passes, she shares more fantasies and asks me to write them. Most notably, her getting taken in her office late at night, but sighs in frustration. "Nobody has access, so it's not like anyone could just break in. Besides, nobody would dare."

I send her a nice story about being bent over her desk and fucked in her office and she responds with a pic of her in bra and panties, thanking me for making her cum harder than she has in a long while. It's getting so I have to take care of my own business before I know she's about to leave in order to keep my composure.

A few nights later, she pops up on chat with a simple: "So... how would you do it?"

"How would I do what?" I know what she's going to say, but I want to hear her say it.

"How would you... take control?"

"How would I dominate you?"

She pauses, then... "Yes."

"If you're asking that question, then it's already started."

Another pause. "Yes, it has."

"I'd only touch you in the context of you being submissive. Make your body associate the pleasure with relinquishing control."

"Yes."

"And I'd ask you... I'd TELL you to do things for me."

"What... what kind of things?"

"Are you wearing a skirt to work tomorrow?"

"I can."

"Do it. A short one. And check your messages at lunch."

A long night goes by, and I man my post as best as I can without spending too much time checking my phone. She's never online during the day with her busy schedule, but at lunchtime, there she is. I try to imagine her reaction to my message telling her to go to the restroom, remove her panties, and keep them off for the rest of the day.

Suddenly, I'm taken by surprise at the unexpected sight of her passing my desk; she never leaves for lunch. I can see the shape of her bare ass as she walks out in the sunlight. Jesus. I get another treat as she returns and shortly thereafter, a message. She was so excited at taking my orders, she had to go to her car to please herself.

I can't take it anymore... for better or worse, it has to end today. I can find another job if I have to.

Several torturous hours and a mid-sunset later, she makes her expected appearance to leave for the day. I can still see her panties are off as I watch her leave, and it's the shift of power that makes me speak to her for the first time in person.

"Good night..."

She manages a half-wave as she pushes the door...

"...bosslady85."

...and stops dead in her tracks.