Chapter 2

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.

She looks into the cam. “Yes?”

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.

Sitting in my office is a welcomed return to normal life. Waking up early in my apartment, showering, getting dressed, then coming to the 34th floor of the downtown building. That’s always been the story of my adult life. The bustling city atmosphere is what drives me. I thrive on that.

People ask about my tan, which to be honest, is something I try to avoid. It makes me feel unprofessional since I’d gone on vacation in the midst of an important project. Speaking of unprofessional, when I sit behind my desk at this early hour, I think about how I’ll be seeing Annie later. Our webcam escapade was never resolved, there was never closure.

At the end of last week, when Annie and I were the only ones left on the conference call, she pulled her pantyhose down and showed me her labia. No warning, nothing. She just stood up and put her crotch to the camera and did it. I could barely look, to tell you the truth. It was like the sun shining in your direction. More specifically, it was the wrongness of it. My role and responsibilities mean everything to me, I want the status that comes with it, and no sexual act ever feels worth the risk.