Lady Boss Ch. 01

I can still remember the day, it was nearly six years ago when I gave my first speech to the New York office. I can't remember exactly what I said as I looked out at the hundred-plus faces for the first time but what I recall the most was wanting to scream, "FUCK YOU." Not at my staff you understand, I love them all, but at the corporate bullshit that had tried its hardest to stop me from succeeding as a woman. Yet there I was at 42, standing in front of my own office as 'the boss'.

I should have got the promotion back home in Houston, but it was considered a 'plum' job. It was accepted therefore, that it had to go to the right 'man' in the company. I think they were almost surprised when I moved to New York, halfway across the country but I was determined to succeed whatever the cost.

Part of that price was my marriage which to be honest wasn't so much a loss, but more of a mercy killing of a wounded animal. John and I had been limping along for a few years, living pretty much separate lives. He stayed and I left, moving into an apartment in Manhattan that had the most stunning views across the city. The one thing that kept running through my head was that somehow, I had failed.

Turning to the group I looked into their faces, determined I would never fail anyone of them. Fixing a smile to my face, I started my speech.

*****

I seemed to settle in fairly well as the office started to buzz with both productivity and happiness as people became more settled in their work. The previous boss had been very stand-offish, whereas I wanted to create a more family feeling. I told everyone that if my door was open, they were to walk in and I would be happy to talk. Likewise, if it was closed then I wasn't to be disturbed. I did my best to make sure it was open as often as possible.

I encouraged staff social and sporting events, and helped set up a women's basketball team as I played a bit back in college and insisted that on the court, I was Janice, not the boss. It was there that I met Kayla and my life changed.

*****

"You look so nice in business attire, boss, not only in basketball gear."

I looked up to see the smiling face of Kayla who was leaning casually against the door frame. She was one of the rising stars in the office and also a damn good basketball player. A little younger than me, perhaps in her early 30s, but like me tall and athletic.

I could see on her face she was nervous, so I laughed, "How many times do I have to tell you Kayla call me Janice." I was casual but a bit surprised at her words, so without thought I followed with, "Did you think I looked good in basketball gear?"

"Oh! I thought you saw my admiring looks."

Then she blushed, before putting down the papers she had bought and left. As she walked away it suddenly dawned on me that she was flirting with me, something that hadn't happened in many years. My head was spinning as she was a woman like me. I didn't think I gave off any gay vibes, maybe it was being divorced, who knows? What I did know was it made me feel good.

*****

A few weeks later the game was cancelled so I decided to stay late in the office as didn't have any urgent reason to go back to the apartment. As I sat at the desk my phone buzzed with a text message. Looking down I saw it was from Kayla.

"Game cancelled. Do you fancy a drink? xx"

I stared at the text for a few minutes considering what it meant. Was I seeing something that wasn't there? Just because another woman asks you for a drink does that make her a lesbian? Was I misreading signals? I tried to remember when we changed after a game, did she look at me in the showers?

To buy time I texted back, "Who else is going?"

Her response was quick, "Just you and me xx"

There it was, the xx again. Were they kisses or was I being stupid? I had been straight all my life and never even looked at another woman sideways unless it was to check her out as competition.

In the end, I took the coward's way out and texted back, "Sorry too much to do in the office," then as an afterthought I deleted the xx I was going to add.

Her response was simple, "🙁"

For the rest of the evening, I tried to focus on my work but found myself picking up the phone and looking at the message, wondering if I had been too hasty.

A few days later, as I was leaving work, we rode the same elevator.

"It's Friday night so what are your plans for the evening? "I said trying to sound friendly but not flirty.

"Chinese evening in front of the TV," then she said, "I would have invited you but you will say no."

Was she coming on to me or just being friendly, I decided there was only one way to find out as I said..."Well...invite me then."

She had an interesting look on her face as she said with a loud laugh, "Only if you bring wine, and it had better be expensive."

The whole conversation was confusing and mixed. Although I was not naive by any means, I had never dealt with women like this and had certainly not dealt with flirtation in many long years.

"Sure, ma'am" I replied putting on a Southern drawl.

*****

The question ran through my head, "What do you wear to a date that is not a date, with someone where you are their boss?"

In the office, I always wore conservative and professional clothes, so it was a relief to change into something lighter and more relaxed. As it was summer I decided on a short flourish dress that with its floral pattern I felt it gave me a sense of freedom and less formality. The way the light material of the dress floated I thought made my legs look attractive. I wore lipstick and some light perfume, and I even thought about wearing sexy underwear. Then I mentally chastised myself for perhaps seeing something that wasn't even there. I was going for a drink with a work colleague not going on a date. The chances are that she was just trying to impress the boss and any lesbian thoughts were in my imagination and fantasy.

She had given me her address and told me I was welcome any time after seven, so I wanted to be on time but also perhaps a fraction late, so I didn't look too keen. On the way I stopped at the store and bought a $50 bottle of red and for the first time in ages I was conscious that I had drawn some stares from the men around me.

When Kayla opened the door, she was dressed very casually in jean shorts, a t-shirt and bare feet. I was pretty certain she wasn't wearing a bra but felt myself colouring up in case she caught me checking her out. She was full of energy, talking a lot as she walked around the place, whistling softly when she took the wine.

Then she paused before she looked at me as she said, "Hope you like it hot and spicy."

My brain went into overdrive, "Was she coming on to me already, how should I respond?" but before I could formulate my response she went on, "I have ordered for us both so have done a mixture of tastes."

At that exact moment, the doorbell chimes and she went to collect the food, again leaving me wondering if I was just imagining things.

As we ate, I kept admiring her long legs that were toned and muscular and she would switch from having them tucked under her, to on the floor.

The topics ranged from how I was finding New York, through to my marriage, muttering sympathetic sounds when I mentioned it had ended when I moved. She asked me casually if I had made any friends since I had moved, and in the back of my head, I wondered what sort of friends she was enquiring about. I casually mentioned how all my time was focused on the office.

It was at that point she casually passed a comment that confirmed what I had suspected.

"Yes, moving can cause problems. When I moved here from San Francisco I split with my girlfriend at the time. We keep in touch but it's just Christmas cards now."

So, she is a lesbian I thought to myself but was then racked with doubt, "But does that mean she fancies me, what should I do if she does?"

"You aren't originally from San Francisco though are you," trying to act nonchalant about the fact she had a girlfriend, though what I wanted to ask her was whether she had hooked up with anyone else.

"Nope, originally a northern girl from Minnesota," she laughed in a way that was natural and confident.

"Ah that explains the tall figure, Ms Viking," I said smiling at her. I thought I was tall at 5' 10" but she was a good 4 or 5 inches taller than me in her bare feet.

"It's all in the genes and thinking of genes that must explain the beauty of this southern belle," as she looked me straight in the eyes.

It was like being hit by an electric shock as I stared into her pretty face and beautiful blue eyes. I knew she must be hitting on me and for the first time with another woman I wanted her to continue.

If she had kissed me at that moment, I would have happily let her but to my surprise she leapt to her feet, "This bottle is nearly empty, let me get another. It won't be as good but should be OK."

As she vanished into the kitchen I was wondering if I had done something wrong, or perhaps misread the signals. I was asking myself, "How will this go? What am I stepping into?" She is openly gay and I was straight, well at least I thought I was, but I didn't know what to do next.

Almost as if there was a change of tack Kayla talked about the office, about basketball but didn't seem to pursue her flirtations, which had me feeling a little disappointed.

It was about 11 when my phone buzzed to tell me my ride was here.

"My ride is here," I said as I got to my feet, "time for me to go but I have enjoyed this evening. Next time it's my treat."

She looked at me and smiled, "I would love to Janice. It has been such fun getting to know you better."

"Please kiss me," my brain was screaming but she just gave me a sisterly hug.

As I rode down in the elevator, I kept asking myself over and over, "Where was this going?" I wasn't sure but knew I wanted to stay on to see the ride all the way to the end.

*****

The office is big, so I barely saw her over the next few days during work. I had a lot of mixed feelings after the dinner at her place. Part of me wanted it to happen but then again, another part of me was screaming no way. I found myself looking for her, hoping to bump into her at the coffee station then moving away telling myself off for acting like a lovesick teenager. I couldn't understand what was happening to me, it wasn't even like she had made a move on me, but something was nagging away at my brain.

Then on Wednesday evening, we bumped into each other in the changing room for our weekly basketball game. Her greeting wasn't cold, warm or even effusive it was simply perfunctory. I found myself distracted by how great she looked, her legs muscles, her arms and I found myself sitting out as I didn't play well, I was so distracted. What made it worse was she looked like she didn't pay any more attention to me than she did to anyone else.

I found myself trying to talk to her, just me and her, I wasn't sure if I had done something wrong. I thought my chance had come when a couple of the girls wanted to go for a drink, but she did not. I went for a drink with the others as I didn't want to show any special signs related to Kayla.

In the bar, I texted her to check if all was ok, but her reply was just "yeah" and nothing more. That night felt odd, as although there was noise and laughter around me, I was focused on my thoughts as to why was I that much occupied by Kayla and her actions.

Then one of the girls who went with us to the bar joked, "Kayla must be fucking the hell outta some pussy...that's why she is not with us." The rest of them fell about laughing and exchanged a few knowing nods and winks.

When I got back to my apartment I couldn't decide if I was hurt, angry or just plain jealous. I got changed into my silk robe and poured myself a hefty glass of bourbon, grabbing my laptop. Normally at night, I check for email but even though I hovered over the mail icon my heart wasn't in it. All I could think of was Kayla 'fucking the hell out of some pussy.' Pulling up a search engine I did something I had never done before, I searched for lesbian porn.

Sure I had looked at porn before, I wasn't a nun, but this was the first time I had looked specifically for lesbian porn. Normally when two women played with each other on-screen it would also have the addition of a number of cocks they were fawning over together. I found myself looking at how the scenes appeared differently. Without realising it, I started to identify with the women on the screen.

It was the scene where one woman was being seduced for the first time that started to get my pulse racing. I hadn't even realised that I had slipped my hand inside the top of my robe and was rolling my nipple between my finger and thumb. Undoing my belt, I let the robe fall open as I parted my thighs, shocked at how wet I was. As I ran my fingertip up and down my pussy lips gently dipping inside all I could think of was it being Kayla's finger.

With a start, I sat upright and slammed the lid shut. I was being stupid. I was Kayla's boss, 10 years her senior, what on earth was I thinking that she might even remotely fancy me? Pulling my robe around myself I drained the glass and walked into the bedroom muttering, "You need to get laid girl; it's been far too long."

*****

The next day I felt guilty and had to mentally shake myself out of it. Having inappropriate thoughts about a co-worker was only wrong if someone acted on it, but I found myself looking for her. In the end, I knew I had to bring matters to some form of conclusion, so I texted her.

"Hey if you are free do you fancy dinner Friday?"

My finger hovered over the send button for a moment and then I tried not to hold my breath as I waited for her reply. The three dots appeared, "Kayla is typing," then went, then appeared again. This went on a few times before her reply came through.

"Sorry can't."

I was so unsure what was happening but one of the reasons I have been so successful in my career is critical path analysis. Pulling a pad of paper to me and grabbing a pencil I wrote across the top, "Why?" and underlined it. Then I wrote a set of bullet points,

"1. She is having second thoughts about trying to seduce me. 2. I am her boss, so she is worried about the implications. 3. She is trying to lure me in like a spider to a fly."

I looked at the list and considered each one in turn. There was no reason to suspect number one, we seemed to get along fine, so I drew a line through it. Number two seemed to have some merit but I could only reassure her if I was with her out of work. Number three seemed farfetched though I knew that Kayla did very little without a reason. If it was number three, then to be honest, she could snare me all day long.

When I got to Friday night, I tried to distract myself that evening, but just couldn't as the number two reason on my pad seemed to be paramount to resolve, so I found myself texting her.

"I had an early dinner with a friend so was wondering if you wanted to share a bottle of wine?"

I waited for her reply which seemed to come through fairly quickly,

"I am a little tired...but, if you want to come over, I will have a drink with you."

My heart leapt with joy and I quickly replied, "Or two 😉" but she didn't respond.

I bought a more expensive bottle of wine, and if I am honest with myself, I wanted to impress her. When I got there, she was in a cut-t-shirt, short shorts, bare feet with her killer abs and legs on display. Be cool I told myself as I walked in and went to the kitchen. I opened the wine and poured two glasses before walking back into the living room while she sat and stretched her long legs on her chaise lounge.

There was a huge difference in her behaviour between the two evenings. The first time she was full on energy, now she seemed much more guarded and cautious, almost distancing herself from me.

"Is there something wrong Kayla?"

"No."

"It feels different, you seem distant, have I upset you in some way?"

"Look... you are an amazing woman... and I like you...a lot," she paused while she considered her next words, I could feel the blood pumping in my ear, "but...this could get complex... you are my boss."

She is super smart and every move is measured as I learned more and more about her. It was clear she wanted to make sure I initiated things or give my clear approval for her to proceed. I found myself saying, "You are an amazing woman yourself, Kayla. Please, don't think of me as your boss...think of me as just a southern belle."

As soon as the words were out of my mouth, I couldn't believe I had said that, but I felt like a young girl wanting to be taken.

She looked me in the eyes and said in a low husky voice, "Come here."

I got up, walked to the chaise sat next to her, my heart beating in my breasts like a caged bird. She brushed her hand on my arm and then kissed me with a soft kiss... then a longer one...and another.

She brought me close to her and I moved to sit in her lap, straddling her legs as we kept kissing. Her hands were touching me, undressing me, and my breasts were exposed, in her mouth. Before I knew it her hands were touching me everywhere. I felt one of her big hands on my ass and the other on my back before she slipped it to my mound.

I was moaning but then I felt her power. I am not a little woman, but she flipped me from sitting on her to sitting on the chaise. Then she was over me so swiftly, pulling my panties up my legs. She was kissing my calves as she did it and was looking into my eyes as she pulled them off of my ankles. Then she dove into my pussy.

She licked me...ate me...fingered me....it felt like she did it forever. I had never had anyone go down on me like this. I arched up to her mouth in pure joy as I came but she kept licking, not stopping but tormenting my very soul as she kept me on a peak of sexual bliss.

She then hugged me and kissed me as she asked, "Do you feel good?"

"That was amazing. I loved it but I am worried that as I have never eaten pussy before, and it will be poor for you. But I will at least try to give you back a small fraction of the pleasure you have just given me."

She just smiled, "All in good time. I have more to give first. Do you want to go to my bedroom or prefer to stay here on the chaise?"

"Well, you are still in her shorts and t-shirt."

"That's easily fixed, "she laughed as she started to throw her clothes off, I love your pussy and I want to fuck you and take you to heaven."

I had no idea what she meant other than she was going to go down on me again. I watched her strong naked body go into her bedroom and when she came back, she had a skin-coloured strap on around her waist, and now I understood what she meant.

"It's a high-quality one, lady boss, don't you worry," she said with a wink.

All I could think of was how sexy it looked on her, so natural and perfect as she walked to me. She sat next to me, her strong hands pushing on my shoulders, and I realised what that meant. Dropping to my knees next to the chaise I took the plastic cock in my mouth.

This wasn't the first cock I had sucked but was the first plastic one. I sucked on it like it was real as I felt her hips pushing into my mouth. Whether it was for me to make it wet, which seemed pointless as I was soaked already, or to prove her superiority over me I am not sure. Honestly I didn't care less.

After a minute or two of sucking she used her strong hands again to get me up and lay me on the chaise on my back. I felt her hands on my calves opening my legs before she leaned forward. I felt the head of her cock inside me and we locked eyes as she pushed in deeper and deeper. When she filled me completely, she pulled out, then pushed in again, with long slow deliberate strokes. She folded her legs, so her ass was resting on her feet. My thighs were draped over hers. As she did long slow thrusts in and out she then leaned forward, putting her feet on the floor as she started picking up the pace.