Underneath Every Office Skirt

These black high heels will look good with a cream-colored blouse and my long red hair. That's the first thing that comes to mind when opening the present that sits on my desk. It seems like an inappropriate gift in the current political climate, but these are the latest Jimmy Choo heels worth a thousand dollars.

It's night and I'm taking a tour of my new office in the downtown law firm. Other employees have gone home and the cleaning people are vacuuming in the other rooms. My office is everything I hoped for. It's newly furnished and I can smell the scents of plastic and leather.

People have different reasons for becoming a lawyer. For me, I love giving assistance and being relevant for major events. And if I'm being honest, I want the downtown office. I want the title and prestige. Even the pens and notepads with the law firm logo makes me happy.

In case you're wondering, I'm newly hired as an Associate lawyer, which is a job that'll keep me busy. My specialty is banking and commercial lending, with an emphasis on commercial real estate and asset-based transactions. It's complex and wonky, but I enjoy this kind of work.

At first I thought this law firm was persistent in hiring me because of the new gender quotas that are going into effect. My contract is above what I expected, I was courted heavily, and I'm told that if I do a good job I can become Partner within a year.

It's after my first week at this firm that I find out the real reason:

There are a slew of new laws being enacted at the start of the new year. Changes to the tax code, regulations, and other policy matters. The firm sees this as a gold mine with soliciting past clients for new business. From the firm's perspective, it's easy money.

By the second week of employment, I'm entrusted with more tasks. I've already made personal connections with colleagues and have a grip on how this firm operates. Their style is professional, fast, and client oriented. I've never seen clients treated so well.

That's when I notice a pattern. When our firm sends a team to personally solicit past clients, they always include a woman, who's either a lawyer or paralegal. The woman always wears heels and an office skirt.

When I arrive at my office in the morning, I see an unmarked box from a department store, and it makes me think of the Jimmy Choo heels I was given (and often wear). I open the box and I'm startled by what I see.

Silk stockings with a garter belt. No note attached. No one claiming responsibility for this -- dare I say -- gift? But what kind of gift is this? Who does this in the year 2021? Truth be told, no one ever claimed credit for the high heels either, but that was a more reasonable gesture.

I put the box under my desk because I won't dignify it. I'm still the new person in the law firm and my friendship with everyone is still budding. There's no reason to ruffle any feathers by complaining. So I decide to keep this to myself and hope that someone will explain that it's a bad joke.

My first solicitation assignment is for a lunch meeting with past clients of the firm. I'll be accompanied by two male lawyers and it's my job to explain how to navigate the new laws, while the men have a good time catching up, I'm assuming.

Before the meeting I'm called into Richard's office. I'm nervous about the lunch appointment and I assume Richard is going to offer advice on how to deal with these clients. He's a law Partner, by the way, the one who hired me for this job and promised me a promotion if I do well.

We make small talk in his office and he tells me to close the door. There's an unmarked box from a department store sitting on his desk. He gestures to it, signaling it's for me.

"So you're the mystery man," I say.

I smile and open the box, expecting another harmless piece of undergarment. This is borderline sexual harassment, but oh well. This job means a lot to me and we have a good personal and professional relationship.

Lifting the lid, I see a container that has three metallic objects (shaped like small cones) and a clear bottle with 'lubrication' marked on the label.

"Are these..." I let my voice trail, so he can finish for me.

"Butt plugs. To keep your anus ready when it's needed."

This is beyond a joke and Richard isn't even laughing. I know he's serious. And it confirms the suspicion I had. It explains why there's always a woman that travels with male lawyers whenever there's a meeting with clients.

Sex in the workplace is nothing new. From my general perception, it usually involves a woman giving head because it's quick and easy.

Anal sex? That's a new one. I still wonder if this is a joke because I'm new here, but Richard doesn't budge. I look at the objects that range in size. The smallest is two inches. The biggest is about 5 inches. Ouch.

"I can report you for this."

"You won't," he says, dismissing me.

"How do you know?"

"A feeling. I know how to read women. You're sexy, ambitious, and you have a dark side somewhere inside you."

"That's being presumptuous," I say.

Richard is correct. I'm not going to report this. I have too much to lose. I know what would happen to my legal career. And as a lawyer, I know what a prolonged legal battle would entail. I'd have to give sworn statements about how I'm wearing high heels that were given to me. How I kept the silk stockings under my desk.

Worse, I'd have to give sworn statements about how I'm looking at three butt plugs and a bottle of ass lubrication. I'd also have to throw the professional women of this law firm under the bus, with my assumption that they're being slutty.

Not a great way to spend a year of my life.

"What's your point?" I ask. "Do you think I'm just going to shove that in my asshole? Why are you doing this?"

"Stephanie, take a look at the firm. Tell me what you see."

I turn and look at the open space law firm through the window and blinds. It's a beautiful layout. I see sharply dressed lawyers, paralegals, and secretaries working with diligence. It's my dream job and I don't want to leave this firm.

"This is a great place to work," I say with admiration.

"Underneath every office skirt is a butt plug. Women are required to wear it."

"Liar," I say.

"What makes you say that?"

"Butt plugs? With high heels? I've never done it, but I'd guess you'd need the leg strength of an athlete to be able to walk seamlessly."

"So you think you can tell if a woman is wearing a plug?" he asks.

"If they're wearing heels, probably."

I'm confident in my answer, but so is Richard. He picks up the phone and summons the secretary, who's sitting outside at her desk.

The secretary enters, a rail thin biracial woman (half Korean) named Kimmie, who I estimate is in her late 20's. She wears glasses and appears booksmart and shy. Everything about her presentation is formal and she's always polite.

I don't know what to expect, but Kimmie is wearing an office skirt. It's my first time noticing that her heels are equally as expensive as mine.

"Yes, sir?"

"Kimmie, how's your morning going?" Richard asks the secretary.

"It's going well. I'm confirming upcoming appointments and making arrangements for your court appearance next..."

He waves his hand. "Can you do me a favor? Walk back and forth."

As ordered, the secretary walks back and forth, pacing in the office. The form is composed like a model working the runway at a fashion show. Is she wearing a butt plug as Richard suggests? It's hard to say. Before, I would have doubted it. But I'm not sure anymore.

"You can stop now," Richard says. "Can you do me a favor and bend over? Spread yourself so Stephanie can see what you have underneath."

"Yes, sir."

Although compliant, I can see the secretary blush. She's embarrassed and her lips purse together and her muscles tighten. There's a faint hint of arousal. Does she enjoy being used in this manner? Some women like it. For some women, being degraded and used is their thing.

Kimmie turns, and when she bends over and tosses her office skirt aside, I see a bare butt. No panties. Just her naked ass with skinny legs.

When she spreads her flat cheeks, I see a silver shine in her puckered hole. Oh god, a butt plug.

"How big is it?" I ask.

"Kimmie, show the woman," Richard says.

The secretary pulls the plug out of her anus. It's a slow pull because it's a delicate region of the body. I watch it slide out. I see the lubrication on the metallic surface of the sex toy. It's longer than I expected. The moment it's out, I catch a glimpse of Kimmie's pinkish-red rectum before it closes.

"Four inches," Kimmie says, holding it straight up.

I marvel that such a thing was hidden in her butt while she worked. As a skinny girl she's able to walk like a breeze. How had I missed it? Looking at her thin legs, I see the toned muscles in her calves. She must have been doing this for years to have that level of rectal control.

"Thank you," Richard says. "Put it back, then go to your desk."

"Yes, sir."

I wonder if the secretary feels shame. She does a half-squat and guides the lubed plug underneath her office skirt, towards her anus. She struggles pushing it inside. Her pretty face winces and her toes curl. Eventually it goes in and she walks effortlessly out of the office, back to her desk.

"You've trained her well," I gulp.

"Like I said before, I know how to read women. I hired Kimmie because she's a great secretary, and because I know her true potential."

"Are you fucking her?" I ask.

In all my years doing legal work -- as an intern, paralegal, then lawyer -- I've never discussed sex with a superior. Only with friends once we're outside of the building. This kind of talk could lead to problems in today's climate. But after everything I've seen, the question feels appropriate.

"Sometimes," he replies. "Sometimes the other Partners have a turn. Often the clients."

My jaw hangs. "Everyone is fucking her?"

"Not the associate lawyers," he grins. "They haven't earned the rights to Kimmie's bottom."

"The female lawyers and paralegals. When they go with the male lawyers to solicit past clients..."

I leave the sentence incomplete because I know Richard will understand. It's such a lewd question. It feels like slander against the women I'm becoming friends with.

"Welcome to the big leagues," he says. "You want major clients? You have to put in the work."

I want to scream at him. I'm close, but I refrain. Richard sees that I'm about to go ballistic and he gives me space to do so. Again, I refrain. I control my temper and take deep breaths to calm myself.

"Aren't there hookers in this city?" I say as calmly as possible.

"Nothing beats a sexy lawyer. It's a power play."

"All the women that work here... the lawyers... they go around giving head and ass? Just like that?"

"Correct," he says.

I clench my fists. "And me? The lunch meeting today? Was I expected to give someone head in the bathroom? I mean, what the fuck?"

"This gift is for you," he says, gesturing to the box on the table. "Feel free to give anyone head, but if you want to become Partner, these plugs go inside your ass."

"Unbelievable."

"I like you, Stephanie, that's why I hired you. Your red hair, your brains, those legs. We need a female Partner and I've selected you."

"You expect me to let some client fuck me in the ass?"

"If you're not ready, bring the secretary," he says. "Either way, it has to get done."

"I can't. I can't. Don't worry though, I'm not going to tell anyone."

"That's fine, I'll send Kimmie with you. All I ask is that you watch and learn. Talk business, do your thing, then learn. Okay?"

It's more than a question. It's a demand. A promotion is dangling in front of my face and Richard knows I want it. Do I want to become a Partner of this firm enough to give up my ass? I honestly don't have the answer.

This changes the mood at lunch because I know what the clients expect. All of us meet at a French restaurant a few blocks away. It's me, a law Partner (not Richard, someone else) and another lawyer. Kimmie also comes along.

As expected, the men laugh and make jokes. I do my best to talk about what our firm can do for them, but in the back of my mind, all I can think about is sex. That's what they're interested in. Their eyes roam my long red hair and drift down to my body.

Our firm pays for lunch after desserts and a client excuses himself to use the bathroom. Kimmie follows, saying she needs to use the bathroom as well. There's a feeling of humor amongst the men, as if they all know the secret. They talk about the meal and other things, instead of what's really on their minds.

For me it's a slow torture. I feel protective of Kimmie because I'm older than her. Eventually I have enough. As the men talk, I toss my table napkin onto my bowl of finished chocolate mousse, not caring that it looks rude.

Then I get up and look for them. It had already been five minutes since they left. Walking through the crowded restaurant, I feel my heart pound, curious about what I may find. Getting head? Sex? Ass fucking? Or maybe they're having an innocent conversation?

The women's bathroom has two women in the stalls. No sign of Kimmie. I barge into the men's room and see a guy taking a piss. He's shocked to see me, but I ignore him. I hear the sounds of ruffling and short grunts. I walk towards the stalls.

Kimmie's heels are pointed towards the toilet inside the stall. The client is behind her, pants down. I can only see their shoes as they're having sex. The sound of my heels make clicking noises on the tile floor, but they don't stop. They continue their muffled and suppressed sexual activities.

I peek through the slim opening of the stall door and see the client's bare butt as he fucks the secretary. This arouses me, although the power imbalance between them is disturbing. Kimmie is a young woman who's shy and impressionable. The client is a powerful older businessman.

This doesn't feel right. It's my first time seeing a woman sodomized. I don't actually see the penetration, but I can hear it. It sounds different than vaginal sex. I can hear the lubrication. I can hear the squishing sound.

Faster they move. Louder are the muffles. I know the client is having an orgasm based on the grunts he makes. I wonder if he's using a condom, or if he's filling that tiny anus. I wonder if Kimmie will clean herself, or put the butt plug back inside with the mess.

Eventually they stop. They're done fucking and I can hear the cock plop out of her asshole. Their clothes ruffle and toilet paper is pulled to clean their mess.

Instead of confronting them, I leave.

While my boss is in court handling a litigation, I'm in the office, finalizing the annual year-end party. We always rent space at a country club so that members of the firm can unwind and mingle with other legal professionals. Clients are often invited to keep business flowing in the right direction.

Stephanie returns from a coffee break and I have an envelope for her that Richard prepared. Our relationship has been awkward since she saw the bathroom encounter, but we're both working professionals.

"This is for you," I say, handing her the envelope.

She accepts it. "Thank you."

We return to our duties. Stephanie is an attractive woman. She leaves her long hair down and I'm sure she knows that every man wants to fuck her. When she started working here, sometimes she'd wear pants. Now she exclusively wears office skirts, just like every other woman.

I think she's preparing herself for the inevitable. A test run.

The envelope I handed Stephanie contains a handwritten letter from Richard along with a contract, promising her a role as Partner, if she complies. I helped prepare the contract, but I'm unsure what's on the handwritten letter.

An hour later, while I'm doing things at my desk, Stephanie approaches me. I'll always be mesmerized by the sight of her red hair and the sway of her hips. Especially as she wears those high heels. By the way, I'm the one that buys the heels for her. Richard gives me his credit card, and I do the shopping.

She's holding the envelope in hand, which is torn at the top. There's a slight redness in her eyes and some smearing around her mascara. Whatever was in the letter made her think deeply.

"I've signed it," she says, putting the envelope on my desk.

"Thank you. I'll give this to Richard when he returns from court."

"You're supposed to do something for me."

"Am I?"

Stephanie's face changes. She's mortified because now it's her obligation to explain things. I remain silent and let her decide how to proceed. I'm capable of doing anything Richard requests. I'm well trained for this job.

After a few seconds, she turns to the side and puts her hands on my desk. She spreads her legs. Her butt is sticking out and it's near my face. Without any words exchanged, I know what I'm expected to do.

I lift the bottom of Stephanie's office skirt. Her muscles tense when her bare butt is exposed. No panties. Exactly as I thought, or maybe she removed her panties before coming to me. I'm in awe of the shape of her butt. It's curved and the muscles are firm.

"Yoga? Pilates?" I ask.

"Running and squats. Let's get this over with."

I apologize for saying anything extra because it's not my place to comment on her physical appearance. My job is to support my boss however possible, and now, that includes preparing Stephanie for a greater role in this law firm.

There's lubrication and butt plugs in my desk drawer. Stephanie remains unmoved when she hears the sound of it opening. I put everything I need on my desk.

First I 'prime' her butt, which is how I was taught. I massage her flesh and her butt flexes whenever her anus threatens to be exposed. With glimpses, I can see that the ring of her anus is light brown and pink inside. It's a delicate area and I wonder if she's a virgin there. I don't ask.

However, her anus is my business. I spread her butt with one hand, then pour the lubrication inside. She flinches from the cool temperature and slippery texture. But she's a strong woman and she can handle herself.

Holding one side open, I pick up the butt plug -- three inches long -- and press the curved tip against her anus and push. I avoid being condescending or patronizing about this, so I don't give her any pep talk. I just do it.

The three-inch butt plug slides into her rectum. Based on her gasps, the clenching of her hands on the desk, and her standing on tip-toes, I'm almost certain she's an anal virgin. It's an odd thrill taking a beautiful lawyer's anal virginity, which is something I'll always remember.

When it's firmly in place, I release my hold, letting her butt close. Stephanie stands upright and I see the discomfort on her face and body language. She pulls her office skirt down and smooths the fabric so that she looks neat.

"How does that feel?" I ask.

"Does it matter? Make sure Richard gets my signature on that contract."

She turns and walks away, but it's far from a cool exit. Her movements are clumsy compared to her normal confident self. Being able to walk gracefully in heels is a skill. Doing it with a butt plug is something that takes precision and body conditioning.

I think she'll be fine in a few weeks.

My prediction is correct when I notice her moving better in the following days. There's still a hitch in each step. A stump in her stride. Otherwise she's her normal composed self. Sometimes when I'm at my desk, I can hear Stephanie screaming at Richard when the door is closed. Sometimes I can hear the sound of spanking.

Once I noticed Stephanie leaving the boss's office with her heels removed so she could walk easier, going barefoot on the carpet. Red marks were on the back of her thighs as she wore a small skirt that day. She got spanked. Lucky woman.