Chapter 3

Steaming hot coffee is on my desk while I check emails and prepare for the work day. I wonder if Annie is going to wear stockings or pantyhose. I’ve masturbated thinking of her a few times and I’m sure she’s done that with me.

Through the open blinds of my office, I see Annie going to her desk, putting her stuff down and making small talk with people around her. I can’t hear what they’re saying, but I’m sure they’re catching up after working remote for the last week, and I can see her smiling. Her long hair is pulled back behind her shoulders. She’s wearing the purple dress she showed me on cam last week. It’s form-fitting, the perfect size, and it highlights her slim figure.

My heart beats faster when she walks to my office. She smiles when she sees me. Tucks her hair behind her ears.

“Can we talk?” she says.

“Absolutely. I’ve been meaning to have a word with you.”

She closes the door and then shuts the blinds. The move sets off alarm bells in my head, but it won’t for anyone else on the office floor. In an advertising agency it’s normal to close blinds when showing image projections. But she doesn’t have anything to present other than her new outfit.

When she approaches my desk there’s this nervous tension around her, that wry smile on her lips she has when aroused, and I can see the pantyhose hugging her calves.

“This is how I look wearing the dress,” she says. “Nice, right? Don’t worry, I’m wearing a bra. I won’t make that mistake again. I won’t do anything risky. Privacy is the top priority.”

In subtle movements, Annie lets her hands roam, going lower and lower. She rubs the hem of skirt and grazes her pantyhose. She lifts the front and her pantyhose is crotchless. She’s not wearing any panties. Her bare vagina is right there. When the front of the skirt falls and covers her private area, I look at her, she’s nervous about how I’d react.

I don’t say anything. I’m at a loss for words.

“There’s more to my story,” she says. “From last week. The shoe store.”

“How could I forget? Tell me, if you’d like.”

Annie gets on her knees, right between my legs, beside my desk. I should tell her to stand but she’s already made up her mind. She undoes my shoes, putting them neatly on the floor, side by side. She strokes my bare calves. Am I uncomfortable? Very. But I can’t bring myself to stop her, I’m too curious about what she’s doing, and I’m too aroused.

“I’ve never shared this with anyone, but I wanted to tell you. So you can have a better idea of where I’m coming from. When I worked at the shoe store, I was enamored by professionally dressed women. And they were enamored with me. They thought I was pretty. My boss noticed the glances, the subtle flirtations, and she encouraged me to flirt back because it would help business.

She continues, “My boss was strict on me. Very demanding. We had conversations about my job training and learning what’s best for business. That was when I first learned to please a woman. And how to please. And what I liked. In the backrooms I gave oral to the most loyal clients. My hands were on their pantyhose while it happened. Or stockings. This one customer taught me how to wear them, what brands to buy, she even gave me hers after a long day at work.”

She continues, “Does it make sense now? That’s the reason I wear pantyhose all the time, because that’s how I was taught. It became part of my sexuality, going down on a well-dressed woman, with my fingers grazing that fabric. I love my job here and I want to keep working for you. So I figured it would be best if I were honest about myself.”

Annie looks me in the eyes and lifts my right foot. Then she kisses my bare toes and slathers her tongue in between. No one has ever done this to me before and the sensation feels ticklish. Pleasant. And it’s an erogenous zone I’ve never explored.

Being her boss, I should stop this. Parts of my brain are screaming to stop this. But I’m aching between my legs. The door is unlocked and this is the hour when people arrive. All it would take is one person to open that door without knocking to ruin my career.

My phone beeps. The sound captures Annie’s attention and she looks at me.

“Answer it,” she says. “Being discreet is a talent of mine.”

I hesitate for a few seconds as the phone beeps, and when I pick up the phone and answer the call, Annie’s eyes sparkle as she goes back to sucking my toes. I speak with Richard, the brand manager for the sports drink, and he’s making a last minute request that we expand the target demographic to include the older hispanic market.

“Got it… right… right… Yeah we can do that. I’ll speak with Kimberly about this, I think she’s already here… right… got it… Thank you, talk to you soon.”

Annie hums and moans when the call ends. The girl is having the time of her life in such a submissive posture, her hands stroking up and down my calves. My big toe in her mouth.

“You can stop now,” I say. “There’s work to be done. They want to expand their demographics after one of their athletes got signed to a boxing promotion yesterday.”

When she pulls her mouth away, parts of me feel disappointed, but I’ll never admit that. A trail of saliva hangs from her lips and she wipes it away. She kisses my ankles, calves, then wipes the saliva on my toes using her forearm. She puts my feet inside my shoes after.

I expect her to straighten her dress after she stands, given that she’s always presentable in public, instead she lifts the front of her skirt and holds it. That crotchless pantyhose. That hairless pussy. Unlike the webcam situation and her flashing a few minutes ago, this time I’m unashamed with looking. I stare straight at it. Her dark labia, the intricate folds, those lips. She’s wet. Drooling almost. That’s why she wants to show me.

Her breathing becomes heavy. She’s still holding the hem of her skirt. She wants something more and won’t stop until she gets it. I take a deep breath. Can I give it to her in my office of all places? I kiss her mound and she moans. I part her labia with my tongue, savoring her taste. The girl is dripping. Giving me oral service had done something to her. Maybe I’ll never understand it, maybe I’ll explore it deeper, but for now I push my tongue further and she runs her fingers through my hair.

My first time licking pussy puts her on edge after several tongue strokes. She’s primed to explode and she has an orgasm in my mouth, holding my head in place and not letting me pull away. I’m no longer her boss, I’m the one serving her. I’ve never felt subordinate to an employee before, but I’m glad it’s with her.

After her orgasm, Annie takes a step back and pulls her skirt down, her cheeks flushed and her breathing still heavy. She looks flustered, like she’s come to her senses. The exhibitionist young woman has vanished, and the shy girl has returned, which is what I want to see. Will we do this again? I don’t know.

I must look like a fool with her fluids glistening around my mouth, which I wipe with the back of my hand. She apologizes again, still flustered, then opens the blinds and leaves my office.

Two weeks later I’m stepping out of the office bathroom, and when it’s clear, I give Annie the signal to leave behind me. We have different lunch appointments. She’s with her colleagues. I have a lunch meeting with clients. We’re not on the same level, which is part of the appeal I suppose. She loves the taboo of eating out her boss, and I enjoy doing the same with a subordinate. The main difference is her fetish for my feet.

Annie is wearing an office dress that I helped pick for her. At night she’d send me links for wardrobe and I’d give my thoughts. She chooses her own stockings and pantyhose. Her wardrobe game has been updated in the last week. Especially after I emailed her a $500 Amazon gift card. Sometimes she’ll wear crotchless pantyhose in the office and those are the days when she tends to smile more. When her spirit seems uplifted.

We step into the elevator together with two other men from a different floor. We’re pretending like we hadn’t just gone down on each other. I squirted in her mouth. She squirted in mine. The weight of this secret presses down on me like a physical force. It’s a tightrope of potential ruin, but the fact is, Annie is a fearless spirit that I can’t resist.

I’ve surrendered to her world, a universe of stockings and nylon. I’m addicted. I find myself looking at her legs through my open office blinds. During meetings with my team, I’ll wonder about the state of her pussy, if she’s gone crotchless beneath her dress, or what kind of panties she’s wearing beneath her pants. She never goes braless though. That’s too much of a giveaway. What she enjoys is the secret down below around her legs.

The men in suits work for a different company in the same building and they’re talking about random things. They’re standing near the elevator door and I can’t focus on them. I’m standing next to Annie and extend my hand. That’s all I want to do, hold her hand after that epic orgasm she gave me, and I gave her. She has a different idea, or maybe she misunderstood.

She lifts her skirt and rubs my hand across her nylon. It does wicked things to my nipples and sends a tremble down my spine, even post orgasm. She pulls my hand to her bare crotch, with that crotchless pantyhose she’s wearing. I finger her, touching my dried saliva, then deeper into her cunt. She doesn’t moan because neither of us want those guys looking in our direction. Instead she arches her back and her lips quiver. Silent.

When the elevator door opens upon reaching the lobby, I pull my hand away and lick my fingers. Annie fixes her dress to make herself presentable in the public eye, more specifically to the corporate types that surround us. She’s meeting up with colleagues for a burger, I’m going to a French bistro. The corporate world, I realize, is far more nuanced than I had ever imagined.

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