Pantyhose Stockings Office Girl

Certain things change as you get older, like learning to appreciate solitude, being all about your career, then accepting these things as normal. I'm 47 years old and taking a solo vacation in a Caribbean beach resort. Trust me, this isn't my idea. I'd much rather be in the office. I'm a creative director at a big advertising firm and we're busy with different clients.

Right now we're testing a cameras-on approach for the updated work-from-home policy. It's basically leaving cameras activated for longer periods of time, even while doing nominal tasks. Management wants to see if this boosts productivity. That's why my boss kicked me out of the office for the week, booking a short vacation on the company dime. He also claimed to be doing me a favor.

After a morning swim in the ocean, I'm inside a small beachside bungalow, towel drying my hair. Tshirt, sarong, barefeet. I take a few moments to become presentable for work. After preparing coffee I log into my Zoom account and connect with my team. People smile, we say our 'hellos,' then I set the agenda.

It's the second day of this experiment to make work-from-home more effective, and I'll admit, watching everyone on their webcams has become an odd hobby. It's incredibly voyeuristic to see into each other's place of living, how they dress at home, their stuff in the background, even the snacks they eat.

One thing about the advertising field is that it's mostly women. My team reflects that, many of whom are Gen Z that I've personally hired, and I'm the oldest of the group. You hear a lot of horror stories about the work ethic of the younger generation, but I enjoy working with them.

Allow me to make a confession. There's a girl named Annie who's the most interesting to watch on my screen. 26 years old, light experience but she's bursting with ideas, and she's able to sit there for hours on end. She's the kind of girl who bakes cookies at home, brings them to the office, and beams with pride when you accept one.

In the office she's well-mannered and charming. Soft spoken. Everything is always neat. But on webcam it's the small details which gives me different insight into her.

You know that pose where business men lean back and put their feet on a desk? Imagine a young woman doing that, but instead of dress shoes, she's wearing stockings or pantyhose. And having a smaller frame, her body would be curled. Sometimes she'll put one leg on the table -- always with legwear -- while typing normally.

Whenever I'm talking she'll sit upright and give her undivided attention. It's only during quieter periods when she thinks no one is paying attention, that she'll give a flash of pantyhose or stockings. Only for a few moments at a time. It's like she doesn't realize what she's doing. At times she'll rub her foot while reading something on her screen, a small, unconscious gesture that hints at a deeper level of relaxation.

To be honest, it arouses me. I've never done anything with a subordinate or even a colleague or boss. Never even been with a woman. I've been faithfully married for over ten years. When that ended, romance became the last thing on my mind and I've been focused on my career. Why these feelings for her? I don't know. Maybe it's the voyeurism of seeing a forbidden side to her. And I say 'forbidden' because young women like Annie aren't the kind to show off their hosiery.

I go for a swim at noon and it's blazing hot. Afterward I remain in my bathing suit and have lunch at this place along the beach, sitting at a solo table under a large umbrella, and order fried fish with rice and beans. The fresh squeezed juice hits the spot.

Returning to my bungalow, I strip off my bathing suit to hang on a rack. I put on undergarments along with appropriate clothing. When I sit in front of my laptop, many of the cams are turned off, or there are empty chairs while people have their break. One person is working, one person is having lunch.

I'm typing an email and movement on the screen catches my attention. Annie is walking around her webcam and it looks like she's had a shower with her face bare and her long hair free. She's picking things up around her living room. I should be working, but I love watching her.

She's wearing a loose black tshirt which touches her thighs, a punk rock band on front, braless from the shape of things. No pants, not even a skirt. Most of her legs are visible and she's wearing stockings. As she mulls around her living space, arranging things, she stops to think for a moment. When she bends over to pick something up, it's clear that she's not wearing panties either. The bottom of her labia is showing and there's some pubic hair.

Poor girl has no idea she's being watched. She thinks no one is paying attention. She leaves the screen and I'm disappointed, but at the same time I'm glad that she's sparing herself worse humiliation if anyone catches this. Should I email her privately and tell her to be mindful of the webcam? As the manager, I should

A few minutes later, she returns to her computer with an appropriate top and a bra underneath, light makeup and her hair is tied. But as she sits down, I notice her bottom is the same. Stockings. And I didn't see anything else on her legs. Is she even wearing panties? The thought of Annie sitting like that makes me melt inside. She looks at her computer screen and puts on thick frame glasses and starts typing.

Is this how she always dresses off-screen during work conferences from home? She has a clear affinity for legwear. She's the only person I've ever seen to wear that on a home camera, much less on a consistent basis.

Others return to work and activate their cams. We have another session before calling it a day. Does it beat the office experience? Depends who you ask. We're hammering ideas and finalizing plans for a new sports drink. Dmitri is sharing images of graphic designs he's made and we're discussing them as a group.

Part of my responsibility is to gauge the rest of the team, so I keep a close eye on everyone. It's important that we're all on the same page. Is anyone confused? Does anyone have questions? That sort of thing. Without that, this online thing doesn't work.

I notice Annie's right hand below her desk. Zhara, our main copywriter, is speaking and giving feedback on the designs. It's a productive conversation but half my attention is focused on what Annie's hand might be doing. I'm not sure anyone else notices. Why would they? No one else knows that Annie is pantyless except for me.

Her lips curl. Her jaw moves ever so slightly, a secret indulgence? The girl is so brazen about masturbating because no one ever suspects her. She doesn't look like the type, if there ever was one. And make no mistake about it, that's exactly what she's doing. Her shoulder moves and her facial expressions struggle to remain 'normal.'

When we've gotten enough out of this workday, I thank everyone and wrap this meeting. It makes me feel like a school teacher, but whatever. People enjoy working in the comfort of their own home once in a while. Everyone smiles and waves to the camera, while Annie has this relaxed expression on her face.

She remains the last person on the webcam because she takes a moment to wipe her hand with a tissue. To anyone else, it looks like she's cleaning her hand after having a snack, but I know what she did. We make eye contact on the screen. She freezes, having this sneaking suspicion that I'm on to her.

Then she blushes.

"Bye," she says.

"See you tomorrow, Annie."

I'll be honest with you, if I ever suspected a man of doing that, I'd tell him to stand. If he was naked from the waist down, I'd fire him on the spot. Simple as that. He'd be gone. A grown man jacking off during a Zoom call is more offensive than a younger woman doing it. Nonetheless, it's inappropriate and I can't run the risk of creating a scandal.

I compose a new message to email her. My fingers hover over the keyboard, thinking of how I should handle the situation. What gives me pause is knowing how HR departments and employment law works. The fact is, I don't have a single shred of proof that Annie did anything wrong and no one else noticed it. Plus sending an email like this feels gross.

So I close the email, choosing to ignore it -- for now. Everyone has that secret side, but I wonder what made her do it. Exhibitionism? The risk of getting caught is alluring to a lot of people. Her always wearing legwear must be a factor.

I'm scrolling through her social media pages. There's a particular selfie on her Facebook page from almost a year ago. The caption reads, 'Getting ready for work!' and there are congratulations in the comment section, family and friends wishing her luck. In the picture she's smiling and I can see her bedroom.

In the background of that selfie I notice an open drawer with an assortment of undergarments. Not completely obvious, but obvious enough to an observant eye. A regular person looking at that picture wouldn't have noticed, but I'm looking with a different frame of mind.

The more I think about it, the more I believe she did it on purpose. That she put that open drawer in the background to say something to the world. A subtle wink to the people in her life that she's more than just a wholesome girl.

I make the picture full-screen and I lean back and slip my hand below. My fingers help me achieve relief, going deeper and deeper. I study every detail of her face, her bedroom, those undergarments. My orgasm is shameless. What happens in the Caribbean stays here, right?

xxx

Two days later and I'm in the local spa. The hot Caribbean sun has already warmed my skin and I need soothing. It's 9 in the morning and my appointment for a full body massage is about to begin. The room exudes island charm, with wooden walls, the scent of exotic oils, and the sound of waves crashing outside.

I strip naked and hang my swimwear on a hook by the wall. As I prepare for the massage table, the door opens and a woman enters. Maritza, an Afro-Latina employee, a few years younger than me, early 40's I'm guessing. Hardly a professional masseuse by my guess. She has this hard edge about her, a stoic face, years of physical labor will do that.

Maritza doesn't bat an eye when she sees the front of my body as I lay on the massage table, putting my head in the face rest. She doesn't immediately put a towel over my bare backside. Instead she gives her hands a quick rinse in the sink and towels them dry. No greetings. No questions. Nothing. She's all business, which I can respect.

After tossing a towel over my butt and thighs, she rubs oil on her hands and starts working my back. Let me tell you, these are the strongest hands I've ever felt. Her fingers dig along my spine and neck, then around the ribs when she gets to my side. There's a sharp pain with each press, along with a magical release.

This goes on for several minutes, agony and bliss. Her hands go lower and lower, brushing against the towel, touching the top of my butt cheeks, which I don't mind. I accidentally moan when she presses deep into the small of my back.

"You know, you real fine. Maybe we do more than massage, eh?"

The comment makes the hairs on my neck stand.

"What do you mean?" I ask. "Your hands are already working magic."

"I can make sure you leave feelin' even better."

She pulls the towel down and half of my butt is exposed, to which she rubs, pressing deeply, digging her fingers inside. At one point she presses so hard that I wonder if she can see between my cheeks. I should turn this down, but those fingers, her touch...

"How would that work?"

"Extra hundred on your tab," she says.

Maritza pulls the towel covering my body and I listen to her folding it. I'm naked on the table. Before we can discuss this any further, she places a hand between my butt cheeks and slides two fingers down. Her grip is strong, perhaps the strongest I've ever been grabbed down there, but at the same time there's a feminine warmth.

All I can do is focus on my breathing. Pain and pleasure. I've never paid for sexual services before and I never thought it would be in the cards. When I cum, Maritza doesn't flinch. She keeps going with wet fingers until I'm drained, moaning, and my body goes limp.

"You know, I gotta say, you a wild one."

She grabs a small cloth and dries the mess between my legs. My body is still trembling. She goes to the sink and spends a few seconds washing her hands, no soap, then dries with a paper towel. I stand and get dressed, she takes a glance at my naked body before cleaning the massage table, her face stoic as ever.

"Thank was... interesting," I say. "Thank you."

"Come back any time. Tip $200 and see what happens."

I give a forced smile when putting on my swimsuit and thank her again, making a quick exit.

An hour later I'm sitting in front of my laptop dressed in something work appropriate. We have a short workday when it comes to being on-camera. I lead a discussion on where the project is headed and we have an open dialogue on what to do next.

My mood is lighter today, I'm usually a bit sharp tongued. I think my team can sense that on cam, more people are smiling and a few people make jokes. The orgasm paid off and I hope nobody made that connection, that I'd just had a tryst with someone at a resort.

I thank everyone for being productive. As the host and manager, I wait until everyone leaves the chat before logging out, because sometimes people have last minute questions. This time it's Annie who's last on cam. She paces around her apartment, then she bends over her desk trying to log off.

From the way she's standing in that bent over position, I'm able to see down her large white blouse. She lingers in front of her laptop. No bra. Her nipple is exposed. Large and pink. I wonder if she's doing this on purpose, but more likely, based on the calmness of her face, she's oblivious to what she's showing.

"Annie?"

She looks into the cam. "Yes?"

"Your top."

She stands back and uses her hand to press her blouse.

"Oh, sorry. Today's conference call was going to be short, so..."

"So you decided not to wear a bra?"

Her face turns beet red. "Sorry."

"Can you sit down for a moment?"

Annie sits in front of her laptop with formal posture, then tosses her hair back. She takes a deep breath, the kind people give when they're about to be reprimanded.

"Were you touching yourself on cam the other day?" I ask.

Her jaw hangs, her eyes have this wide expression and it's too late to deny anything.

"I didn't think anyone would notice," she says. "Which, I know, isn't an excuse. I'm sorry."

"You don't have to keep apologizing all the time. Just be mindful. And please, be sure to wear a bra."

"Absolutely, thank you."

"What's the reason you're always wearing legwear? I can't think of a single woman who wears stockings or pantyhose when working from home."

She tames her smile, not wanting to go overboard.

"You wouldn't want to hear this," she says.

"I've got time if you're willing to enlighten me."

"This is embarrassing, but it started with a part-time job I got after finishing high school. Sure you want to hear this?"

"You're piquing my interest."

She makes a gulping noise. "Well, I worked at a shoe store, a nice one near downtown. We had a lot of corporate women coming in. I got used to kneeling and providing service. Oftentimes they'd come right after work, they'd still be in their stockings. That's what made me want to join the corporate world. I was envious of that look. You know, that kind of stature and way of dressing. Like I said, super embarrassing."

"You don't have to be embarrassed about your fetishes... I mean... you know what I meant."

We both share nervous laughter over my rare slip of the tongue. 'Fetishes?' How could I have been so careless as to say that? When the mood settles, she looks at me with adoring eyes, as if I understand her, which I do.

"Do you have a preference for what I should be wearing?" she asks. "A dress? A blouse?"

I know exactly what she's doing. I shouldn't play her game, I really shouldn't...

"A dress sounds nice," I say.

"Hang on, I've got just the thing."

When she leaves the camera frame, I regret having said that. Telling an employee what to wear, much less a young woman her age, is flirting with disaster. I'm still buzzing from Maritza giving me an orgasm and I make a mental note to never cum before work again.

Annie returns with a purple dress in hand. She moves her laptop around so that there's space behind her and she stands in the living room. She holds the purple dress against her body, it's form fitting, goes down to her knees, and would bear most of her arms.

I should tell her to stop, but I don't.

"How about this for the office?" she asks. "I'll wear it next week."

"That would be great, Annie, it's a beautiful dress, but I shouldn't be telling you what to wear. Let's be clear about that."

"Our secret. I've been wanting to update my wardrobe. So I'm grateful for any feedback."

"Whatever keeps your nipples from showing in the office."

She blushes. "Never."

When her face turns red we both laugh. I'd love to keep talking to her, but I shouldn't, not in the direction where I know she's pushing this.

"It was nice speaking with you. I'm glad we cleared up any issues."

"Thanks for being merciful. Are you headed back to the beach?"

"A perk of being sent to the islands, right? Yeah, I'm headed back to the beach, this time under an umbrella with a book in hand."

"What are you reading?"

"Seven Husbands of Evelyn Hugo."

"Awesome, I've read that," she says.

"I love it so far. Great characters, sublime writing."

"What are you going to wear?"

"Let's not go there."

"You're right, you're right. Sorry about that."

There's something about Annie holding that dress and seeing her legwear that gets to me. And again, I'm still buzzed from what happened in that spa, so whatever I do can't be held against me, right?

"Do you want to see my swimwear?" I ask. "Something between us, nothing work related."

"Please, that would be awesome."

"Give me a sec. Real quick, then I have to go."

My swimsuit has already dried on the rack. I step out of the camera frame, then strip off my clothes, and it dawns on me that Annie can hear the sound of my undressing. Something about that is a different form of exhibitionism. The listening. Her knowing that my clothes are coming off, then being naked.

By 'accident' a glimpse of my backside makes its way into frame. I'm sure she can see my ass. I step into the swimwear one foot at a time, showing my legs. Putting on the rest, I turn so that my nipples could potentially be seen.

I take a deep breath before facing Annie on the webcam. Perhaps I've made the biggest mistake of my career.

When I face the screen, Annie is looking at me with the most charming smile. It's almost like she's impressed, more than anything else, that I had the guts to go full nude for her, even for those few seconds. She nods like we're on the same page. I can tell she wants to say something smart, but she holds it in.

An hour later I'm on the beach, underneath an umbrella, and my mind wavers between the book and the Annie situation. There are a few topless or nude women on this beach. Some around my age. A few around Annie's age. One young woman kind of looks like her. Light skin with pink nipples, that wholesome appeal.

I put the book down and slip my right hand below. I'm touching my flesh, the same spot where the masseuse had made me cum. During my time here, I've seen plenty of nude bodies, but I'd never seen anyone masturbating or having sex in the open. Will anyone notice me? Maybe if I'm fast enough it'll be okay. I rub myself hoping no one is looking. Or maybe a part of me wants to get caught.