Tales of Transwomen Tops Ch. 01

Hello! I'm fairly sure the title of this series will give it away. If you're not interested in sexually dominant / aggressive (but not rape-y) transwomen, this won't be for you. This is nothing short of pure fantasy. I have other stories featuring transwomen that are far more realistic. But if you like to watch a little bit of transgender porn, a popular sub-genre is of transwomen topping guys.

And that's what this series is about. As I said above, pure fantasy stories about beautiful women. Big tits. Big dicks. And the sort of women love to fuck guys. Other stories in this series might visit upon other topics such as interracial (black / Asian women), group sex, gangbangs and whatever else that comes to mind. Some stories might have a romantic edge, others will be more about two people just wanting to fuck each other.

Usual caveats. All editing and reviewing done by the author with Microsoft Word. Spelling is usually spot on. Australian / British English. Definitely the occasional typo. Grammar can be ropey at times, but it's been a long time since I sat in a classroom. All mistakes owned up to by the author. Please remember this is only fantasy and I'm an amateur.

Comments and feedback appreciated as always.

*****

Being stuck in the office late on a Friday always sucked. While I noticed subordinates and colleagues leaving the building upon the clock hitting five o'clock, some of them stopping at the door to my office to politely wish me a good weekend, my mind was still focused on solving the last major problem of the day before I could finally escape.

It took another ninety minutes, two phone calls and more emails than I would care to count before I finally sighed, slammed the laptop shut and figured anything else could just wait until Monday. Grabbing my suit jacket, I put that on before turning off the lights and locking my office door. Walking towards the elevators, the place was practically deserted. No real surprise for a Friday evening. Everyone clock watched on a Friday, desperate for the weekend to start and two days of freedom.

The lights were turned down low as always, but as I walked towards the elevators, I noticed light from one of the cubicles. They were not the typical high walls that kept everyone isolated, so I could see a woman still typing away, the screen shining brighter than the lights now dimmed over her heads. I was surprised to see anyone else still at work.

Walking towards her, she was concentrating on whatever was on her screen, but seemed to sense my presence. Turning towards me, she almost leapt out of her seat and squealed, earning a smile from me as she immediately started to blush. Her long blonde hair had covered a pair of earphones, so she hadn't heard me approaching.

"Sorry to startle you," I stated once she'd taken them out of her ears, "But what are you still doing here?"

She didn't reply immediately, removing her narrow black framed glasses to give her blue eyes a quick rub. "There's just so much work..."

"Is it nothing that can't wait until Monday? It's Friday night..." She shrugged and seemed to almost blush again. "Come on, I won't have anyone else stuck here working on a Friday night after I leave."

Glancing at her screen, she placed her glasses back on her nose and quickly saved and closed whatever she was working on. "I guess it can wait until Monday," she offered once the screen turned black.

I stepped back as she stood up and I was momentarily surprised at how tall she was. I was around six foot myself, but glancing down towards her feet, noticing a small pair of heels, she would have been as tall as me without them. With heels, she stood taller. Admittedly, I didn't recognise her as she wasn't one of my subordinates, and though I recognised faces...

"How long have you worked here?" I asked.

"I only started a month ago," she replied, grabbing her handbag, smiling as I gestured toward the hall where the elevators were, "I'm Kelli. With an I."

"I'm Michael. Most just call me Mike."

She shook my hand, and I was surprised by the firm grip, though her hands were still wonderfully soft. Meeting my eyes, she smiled again as our hands remain clasped for a couple of seconds longer than normal. It was amusing that I had to raise my chin to meet her eyes, stepping onto the elevator and standing side by side, three sides being mirrors so we could see our reflections.

"Are you enjoying it?" I wondered, "Who's your boss?"

"I work for Amanda Reilly."

"Mandy? You've landed an excellent boss with her."

"Yeah. She's really nice. Made me feel very welcome immediately. Figured out she's demanding and wants results, but I have the support to make sure I can meet those deadlines."

"So being late in the office tonight?"

She glanced and smiled at me. "I guess I just like to be on the front foot when arriving on a Monday."

The elevator dinged as we made it to the ground floor. Walking through the darkened lobby, we both wished the pair of security guards good evening, aware they'd be stuck there until early the next morning. After walking through the glass revolving doors, we stood together for a few seconds. I didn't drive into the city, preferring to catch a train then walking home to my apartment.

Something about Kelli interested me though. Being honest, she was bloody gorgeous. And considering I was single, and had been since been splitting with my last ex-girlfriend... "Want to get a drink?"

"Huh?"

Meeting her blue eyes again, she seemed to be rather shocked at my question. "I asked if you wanted to go get a drink?"

"You'd like to get a drink with me?"

Meeting her eyes, I felt another smile form. "Well, of course. Why wouldn't I?"

Remaining silent for a few seconds, no doubt in thought, she eventually returned my smile. "Sure. I'd love to get a drink with you, Mike."

Being the CBD, there were numerous bars and pubs dotted about, most of them full of office workers getting started on their weekends rather early. Walking by a few, you could hear the loud conversations and laughter from within, the clink of glasses and the occasional breaking of a glass hitting the floor, usually followed by a shout and more laughter.

I managed to find us a bar that was slightly quieter though we still couldn't find a seat, having to make do with standing in an area near the bar. I ordered a schooner of beer, Kelli asking for a glass of wine, something I was happy to buy for her. The bar wasn't too loud, so we were able to make some small talk, sticking to general topics.

Despite the position I held at the company, I still called the western suburbs of the city home, remaining relatively close to my parents and sister. Kelli lived further to the south-west, an area considered more deprived and rougher than many other areas of the city. We'd both attended university and finished with good degrees.

"Single?" I finally had to ask.

"I have been for a while. Just can't find the right type of guy. There are one or two ways in which I'm an acquired taste."

Ordering a second round of drinks, I pondered what she could have meant. I know many men would probably be intimidated by her height alone. Looking her over again, she certainly had a fantastic chest on her, the blouse she was wearing tight to what I assumed was a toned body. If she was wearing a bra, it was certainly lifting them. Or they were fake. Either way, there was no missing her father long legs, her skirt down to her knees, the rest of her legs in stockings.

Handing her a second glass, she took a sip of wine. I watched her eyes look me up and down in return. "How do you mean?" I wondered, curiosity getting the better of me.

Looking thoughtful, she finally smiled at me. It lit up her face, accentuating her lovely cheekbones and her rather pretty eyes. "Maybe next time, Mike. It's something I would need to share but I have to feel comfortable first." Taking another sip, she added, "Though how are you when it comes to a dominant partner, for example?"

"You mean a woman who wants to take control?"

"Something like that."

"I think a lot of men would like a woman who knows what she wants in bed. Men also want a woman who participates and doesn't just lie there. Though I guess there are many ideas as to what 'dominant' would mean." Sipping my beer, I chuckled. "Got sexual rather quickly."

"We're just talking, Mike. And I'm not blind to your immediate interest in me."

"Self-confidence is a good thing."

"Took a long time to get to this place. I might seem a little unsure to start with, as despite the confidence, I still have to be wary. I think most women are."

We finished our drinks and decided to call it a night. Walking together towards the train station, we travelled west as far as a station where she needed to change. Before leaving the seat that we were sharing, she leaned over and kissed my cheek. Leaning as close as she was, I got a good whiff of her perfume, her lips soft on my stubbled cheek.

"See you on Monday, Mike. I'll make sure I keep an eye out for you."

"I have a feeling you're going to be rather unmissable from now on, Kelli."

"Like what you see?"

"I'm usually rather guarded around colleagues, but I think I might just have to make an exception this time."

Kissing my cheek again, she got up and walked towards the doors, glancing back a final time and smiling. Arriving home half an hour or so later, I called my sister as I usually did ever Friday night, agreeing to go and visit our parents on the weekend for lunch. My sister was a couple of years older, happily married, three kids. I'm sure my parents were hoping I'd be married and starting a family, particularly as I was approaching thirty, but though I'd dated and had relationships, I was focused on making money at the same time, hoping to retire earlier than most.

When she mentioned the fact that I was calling a little later than normal, I knew I was in trouble when she immediately asked questions when replying I was out for drinks with a colleague. Thankfully, my sister didn't interfere in my love life too often. She'd set me up on a date three times with one of her friends. Only the second friend went somewhere, and it didn't last all that long. The other two, there was absolutely no chemistry, left wondering why my sister had bothered at all.

Word got to my parents, as I'd barely stepped through the front door on Sunday when my mother was inundating me with questions about my date on Friday. "It wasn't a date. I left work late on Friday night, only Kelli was still there, and I thought we'd just have a drink before going home separately."

That didn't work, of course. My sister smirked away as our mother interrogated me in regard to Kelli. When I told her that I actually didn't know all that much about her, Mum suggested that I should do just that. Get to know her better. I had to admit, our conversation had flowed rather easily. She was attractive. Intelligent. And she seemed to like me in return.

Returning to the office on Monday morning, I wasn't one of the first to arrive, many of the office staff getting in to prepare themselves for the day, some enjoying a coffee in the canteen before heading to their desks. Walking past Kelli's desk, she was already in her seat, typing away at her keyboard. Lifting her eyes for a moment, the immediate smile that formed made me stop, feeling my own smile form in return.

"Morning, Kelli."

"Morning, Mike."

"Enjoy the rest of your weekend?"

"Spend Saturday night with some girlfriends, but otherwise, nothing much. You?"

"I learned to never mention to my sister or parents that I spent any free time with a woman."

Kelli giggled at the exasperated tone in my voice. "Setting up our wedding already?"

"Something like that," I muttered, "But I did enjoy your company, even if it was only for an hour or so."

"The question is whether you'd like my company again, Mike?"

The sultry tone had my eyes widen as I saw her in a new light. She was smiling at me, but there was a look in her eyes that told me that she was quite interested in me. Maybe she'd just needed time to think. Maybe she'd mentioned me to her girlfriends. Or maybe, like me, she was a little tired of being single. Perhaps not the best of reasons to get into a relationship, but I'd felt a spark while we'd been drinking.

"Maybe we can go grab lunch and coffee during the week?"

"And perhaps something a little more substantial this weekend?" she countered.

I felt my cheeks start to grow warm at how forward she was now being. "Sure, we can talk about it during lunch."

"Today?"

"Sure. I usually take lunch after 12:30."

"I'll come knocking on your door to make sure you eat."

Managing to concentrate on my job was surprisingly difficult as I found myself thinking about Kelli. She hadn't been shy or nervous, but the change in demeanour so quickly did surprise me. She turned up at the door to my office not long after 12:30. Walking around my desk, she grasped my shoulder and ensured I was looking up at her.

"Lunchtime, Mike. Come on, you promised me coffee."

Standing up, I nearly bumped into her large rack as she stepped back just in time. Putting on my jacket, she then took my hand and somewhat dragged me forward through the office towards the elevators. Walking outside once we reached the lobby; she led me towards a small diner located on a side street. Taking a seat at one of the tables, a waitress approached and seemed to know Kelli rather well.

"And who is this handsome gentleman?"

"This is Mike, Simone. He's one of the top dogs at the company I've recently started working."

"I'm an operations manager," I added, glancing at Simone, "There are plenty of people I report to."

"He's being modest, Simone."

"Modest in addition to handsome. Might be onto a winner with this one, Kelli."

I felt my cheeks growing warm again. "I'll just have my usual, Simone. What would you like, Mike?"

"All day breakfast looks good. Coffee on the side."

We made more small talk as we waited for our food. The coffee was the sort you'd get in this sort of place. No soy latte's and mappa-frappa-crappacucinos. Just strong black coffee with a dash of milk, cream and a sugar or two if desired. When the food arrived, it smelled delicious, and it tasted even better. Kelli's meal looked just as good, enjoying the moans she made as she shovelled another forkful of food into her mouth.

"That was good," she said once her plate was cleared, "If you're wondering where it goes, I do go to the gym nearly every day. Can't look this good without some exercise."

Returning to the office, I did wonder if people had noticed us leave and return together. I'd never been one for office gossip though I knew how it worked. There were no rules against office romances, though I knew Human Resources would eventually involve themselves. Not getting ahead of myself here, but I had to consider such things, as although not a direct subordinate, I was still in management.

That lunchtime started something as we ended up sharing our breaks every early afternoon that week. The conversation remained light without getting too personal, learning minor things such as how big our families were, where we'd grown up and gone to school, perhaps stories about friends and adventures. We didn't talk about past loves or our love lives though we'd both been single for a while.

During our shared lunchtime on Friday, I finished my meal and gazed at her across the small table. She eventually noticed me looking, wiping her mouth with a napkin and smiling. "What's on your mind?"

"Want to do something together this weekend?"

"I can think of a few things we could do together, Mike. Depends on what your idea is."

"Dinner, drinks and, I don't know, maybe dancing or something."

"Can you dance, Mike?"

"Not really, but when you're holding a beautiful woman in your arms, it doesn't really matter."

She giggled, a sound I'd grown used to and already really liked. "Smooth, Mike. Sure, you mean Saturday night?"

"Yeah."

"Give me your phone." Handing it over, she put her number in it then messaged herself. "There we go, now you can message me whenever you want. Surprised you didn't ask for it already."

"I'll admit, I wasn't sure what this would turn out to be."

"Mike, I'll be blunt. I'm looking to start dating again... Make of that what you want."

To my delight, she knocked on my office door a little after five o'clock that afternoon and practically ordered me to join her for a drink. We ended up in a different bar, just as busy as the first one we'd visited last week, managed to get stools at the bar. She crossed her legs as we sipped at our drinks, more small-talk, and I was treated to a great view of a toned leg, the split in her skirt riding up her thigh.

Aware we'd be enjoying each other's company the next day, we only stayed for an hour or so before walking to the nearest train station. Before she stepped off to change to her train home, she left a soft kiss on my cheek again, greeted by another fragrance, assuming she wore different perfumes.

"I'll pick you up at your place tomorrow," I told her, "Say around mid-afternoon."

"Just send me a text when I should start getting ready."

I was sitting back on the couch at home, sipping at another beer while watching a little television, when my phone buzzed. Seeing it was a message from Kelli, my eyes certainly widened as she'd sent me a selfie. It wasn't a nude, but it was certainly provocative. Bare shoulders and a plenty of cleavage, blowing me a kiss as she looked into the mirror.

That wasn't the only photo sent. The last one was later that night when I was in bed, a simple photo of her in bed. That was the only photo she added a message, stating she was naked underneath the sheets and was contemplating masturbating.

M: And what will you be thinking about while doing that?

K: Maybe this rather handsome man who works at my office. I find myself quite drawn to him.

M: Do I know him?

K: Maybe... I've warned him what I'm like. I think he's interested in me, at least.

M: If I know him, then I reckon he's very interested.

K: Good to know. Maybe if we do really like each other, we'll end up being compatible in more ways than one.

Waking up in a good mood the next morning, I focused on some chores, so I didn't have to worry about them on Sunday. Thinking about my date later that day certainly had me smiling, exchanging messages with a few friends, all of them hoping that it would go well tonight as I was the only single man left in our friend group.

Letting Kelli know I was getting ready, she replied immediately that she'd already started, a mixture of excitement and nerves as she hadn't been on a date in a few months. She did ask what to wear. I suggested a simple dress or something with a skirt. It was a warm day, and we would be walking around the city, sticking near the harbour and perhaps heading towards the eastern suburbs.

Despite where Kelli lived, her apartment building was one of the many new towers springing up across the city. Buzzing me up, the door was already open. Knocking before walking in, Kelli shouted out for me to come in, finding her waiting for me in the living room. I stopped and felt my jaw drop. The red dress she wore clung to her toned body and curves. Her shoulders were bare, so she was likely not wearing a bra. The hem of the dress only made it halfway down her thigh, and she was wearing what I assumed were thigh high stockings. She had gone with comfortable shoes, at least. Even without heels she was still as tall as me. Maybe an inch taller.

"Wow," I finally stated.

"I'm glad you approve, Mike."

Walking hand in hand to the train station, we didn't have to wait long for the next service into the city. Sitting side by side, she sat close to me, her leg rubbing against mine, ensuring she was holding my hand the entire way. Stepping off at Circular Quay, we wandered up into The Rocks, strolling around, enjoying the sunshine and warmth, thankful it wasn't too hot under the clear blue sky.