Tales of Transwomen Tops Ch. 05

A/N - Hello everyone. If you've read the first four short stories of this series, I wrote them with at least a slightly romantic edge and I hope that's what you were left thinking or feeling too. The next couple of stories I have ready to upload will probably lack that romantic edge, at least compared to those first four short stories, and will instead be more about a man enjoying the company of more than one dominant transwoman.

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I'm sure many of you have read stories about men like me. We were not blessed with big muscles, towering height or a massive cock. That's not to say I didn't have some positives. I wasn't called handsome though plenty of people called me cute. And despite having been what they'd call a 'nerd' back in high school, and not exactly being blessed with the social skills of an extrovert, I was usually everyone's friend.

As I approached the age of thirty, my career had gone from strength to strength. I made great money and was perched in a position within an international organisation that I hoped would lead to some sort of directorship. The bosses already had their eye on me, and I knew if I continued to impress, I'd make my way onto the board. And from what I'd been told, I'd be one of the youngest to make the board in the company's history.

But while my career was going great, my love life was anything but successful. I'd had one or two relationships, but they'd mostly fizzled out. It was partly my fault as I did work a lot. The position I was in required me to be available all the time, and I didn't mind that simply due to the wage I was bringing in. Most women don't like playing second fiddle like that.

There was also another reason why, which I can admit to you fine people reading my story. I've never been attracted to men, I can say that with absolute certainty. I can easily think a man is handsome and that's it. No desire for anything else.

But transwomen? My god, I'm probably a little obsessed with them. It all started somewhat innocently enough by discovering them on the internet, though in the days before social media and when things like pronouns were not on everyone's email signature, and terms like 'shemale' and 'tranny' were not considered as derogatory as they are today... Not saying they were not then, but times change.

Anyway, I absolutely love transwomen. My first fixation was with ladyboys from Asia. They were usually diminutive, with small breasts and cocks, and it was rare to see them topping men. A couple of friends shared the same interests and, as younger men, we'd enjoy finding pictures and videos for our collection.

Then we discovered transwomen from Latin and South America. They're usually tall, with big tits and even bigger cocks, and I'll admit I found myself drooling over them. The three of us agreed that we absolutely adored them, and we'd get together after school a couple of times a week to watch a couple of new videos.

Yes, we'd jerk off together but never touch each other. My eyes were focused only on the television.

It started by just videos of transwomen being fucked by men, but then we discovered transwomen who would fuck men and that was it. My obsession was pretty much complete. The only problem I faced was two-fold.

One was that I thought I was fetishising them, which in truth might have been partly true, though I knew I wanted to meet a transwoman and perhaps form a relationship. Two was that I was rather clueless about where to meet them. In many regards, I was still innocent about such things when I was eighteen. Silly old me, who knew what LGBT stood for, didn't put two and two together and figured I'd perhaps find transwomen in certain areas of the city.

I also knew porn wasn't reality. I might watch transwomen fuck men hard on video, but I did my research and knew many had dysphoria, hated having a penis, and there were many reasons why they were starring in porn. During my time at university, I did partake in certain groups to learn more about trans issues, but even then, not too long ago, it still wasn't a subject in the public eye.

"Ready for your big trip?"

Looking up from my laptop, it was the director who I reported to. A great guy to work for and he gave me plenty of opportunities to show I was capable of taking the next big step. "I'm not sure if this is a work holiday or just a holiday," I replied, "I mean, you're sending me to half a dozen places before I finish in Brazil, where I'm spending a week for the conference."

"You know your stuff, Mark. The CEO, the COO and the CFO all have faith that you'll deliver the goods. If you close the three deals on the table, you're guaranteed a big fat cheque and a seat at the big table."

"Can I have that in writing?"

He chuckled before walking towards my desk, sliding a manila folder across. Meeting his eyes, I glanced at the blank cover before opening it up to see what looked like a new contract. "When you get home, all you'll need to do is hand the signed copy towards me, and you'll have a new office come the next Monday. Your PA can go with you, but you're going to have even more people working for you."

"I'll give it a once over during my flight."

"You have plenty of time, Mark. It's a big decision but you've continued to impress the big three."

Finishing for the day, I returned home to my modern but empty apartment. My last relationship was in the distant past though I didn't feel alone. The friends who I shared my interests during my formative years were still as interested as myself. I knew both my friends had visited trans escorts to get their fix. Paying for sex had never interested me. I wanted to make a connection with a woman first, and part of me still hoped I'd meet the sort of woman I thought I truly wanted...

The weekend before I left, my two friends visited, bringing a couple of new videos to watch. The three of us sat back with a beer as we watched a series of scenes, most involving a dominant transwoman or two with a man. The final scene had me rock hard as it was a five transwomen gangbang of a man. I couldn't resist jerking off, not surprised my two friends joined in. My eyes were purely focused on the screen as I eventually erupted all over myself.

"You think you'll meet a girl like that on your trips?" Steven asked me once we'd cleaned ourselves up.

"No idea. I wouldn't even know where to start anyway."

"I'm still tempted to just go to Bangkok and find myself a beautiful ladyboy," John suggested, "I mean, that's where our interest started, and I still think they're beyond beautiful."

"But Mark wants his girl to have a big cock to fuck him," Steven stated, both giving me a look at I blushed.

"I've always known what I liked, but I also know what we've just watched isn't reality. Porn is not real life," I retorted.

"But maybe it could be?" John wondered.

"Well, if it could be, I wouldn't turn down the chance," I replied.

"Want to watch the other one?" Steven asked.

"What's the title?"

"It's just the sort of movie Mark will love, John. The Best of Monsters of Shemale Cock. Nothing but big cocked trans beauties fucking men."

"You got it just for me, didn't you?" I joked.

"John and I know what you like, Mark. And we thought this would be a good going away present."

Taking off a few days later, I spent most of my time in the first five countries focused on work and making sure I had everything in place to ensure the deals I wanted were completed. But it would be in Brazil where the biggest deals would be sealed. I enjoyed my time in the other countries, though I didn't get much opportunity to do any sightseeing.

My final stop in Brazil would be in the capital, Brasilia. I felt a slight sense of disappointment that the conference wasn't in Rio, but from what I'd learned, the movers and shakers across the globe in our business would be present, and the company I represented had a presence in Asia, North, Latin and South America, so having it the Brazilian capital did make sense.

The flight I was on did travel from Argentina and did need to swap in Sao Paulo to get the domestic connection to the Brazilian capital. Arriving the day before the conference started, the city was absolutely heaving with foreign visitors. Checking into the hotel I would be spending the week at, it wasn't far from the conference centre, greeted with a warm smile and a friendly welcome. My room was one of the best around, offering fantastic views of the city.

Walking into the conference centre the next morning, it was already full to bursting, hearing numerous languages being spoken and there was a sense of utter confusion at times. Finding a desk that could provide me with what I needed, it was a busy day of meetings and signing agreements, including something that made me smile, and want to celebrate, as one of the three main deals I wanted was signed with barely any further discussion.

During that first day, though, I found myself distracted by quite a few beautiful women. That wasn't a particular surprise, being in South America, and not far from Central America and the Caribbean, where it was universally agreed that millions of beautiful women came from the region. But as I strolled along the busy corridors, I couldn't help but almost stare at one or two women that walked by, and when they noticed my glance and they immediately smiled at me, how I didn't trip over my own feet was sheer luck.

Sitting at the bar at the end of the day, I was a little tired and was just going to have dinner, a beer or two, before heading back to my room. I'd brought along my personal laptop that was just full of the sort of porn I'd enjoy watching, my room coming with an enormous television that I could connect to my laptop. After eating dinner at the bar, I was sitting on a stool, nursing a last beer, when the stools to either side of me were taken by a trio of utterly beautiful women.

And I recognised them as three of the women who had captured my attention during the day. Glancing from side to side, the three all smiled at me as I felt myself blushing. The raven-haired woman on the stool to my right ordered drinks in Portuguese, or that's what I thought it was, three cocktails appeared in front of her and the two brunettes to my left.

"Are the three of you local?" I finally asked.

The question made them giggle, in a good way. "No," the raven-haired woman replied, "I'm Kalena. I'm what you call a local. The woman next to you is Luana, she's from Argentina. And next to her is Fernanda, she's from Colombia."

"Nice to meet you all. I'm Mark."

"Oh, we know who you are. We were in the conference meeting you held after lunchtime. I'm surprised you didn't notice us."

Managing a smile, I replied, "When I'm in the zone, I don't focus on anyone. I'm too busy remembering all the facts and figures. I hate working from notes or anything like that."

"You know your stuff, at least," Luana said, her accent not too thick but English was clearly her second tongue.

"What do you think of Brazil so far?" Kalena wondered.

"Well, I've been to a few other places in South America, though I didn't do any sightseeing. One or two days at most, meeting after meeting. As for Brazil, I flew here via Rio, so I saw the airport. Brasilia seems nice if not a little quiet."

"Where are you from?" Fernanda asked.

"Other side of the Pacific. It's a long old flight getting here."

The three finished their cocktails rather quickly, and I was rather surprised they seemed keen to keep me company. When I offered to buy a round of drinks, I found arms wrapped around me and soft lips on my cheek, whispered words of thanks in my ear, all of it making my cheeks feel rather warm. Moving onto more cheerful topics, they didn't seem to give too much away about themselves, but they were full of questions about me. I'd rarely if ever had so much interest from one woman, let alone three. I wasn't fooling myself into thinking any of them would actually go back to my room...

"Why don't we buy a bottle of wine or two, or maybe a bottle spirit, and we head upstairs to your room?" Kalena asked after a third cocktail.

"Huh?" The three giggled as I probably grinned like an idiot. Then I made them smile in return when I added, "I have more than just a room. I'm near the top."

After placing an order for a bottle of wine, and a bottle of champagne to be sent to my room, I slid off my stool and waited for the three girls to join me. Only then did I realise how tall they were. All three were in heels and were easily over six-foot. All wore different styles black dresses that were tight to their bodies, their toned arms bare. The three had large and what looked like fake breasts, and all three were long-legged, surprised that the three seemed to be wearing thigh-highs.

Escorting them to the lifts, they seemed to get rather excited the higher we travelled, stepping out into the hallway where there was only a door at either end. Opening the door, I stood to the side as they walked by, hearing them gasp as they took in the sheer size of the suite. The design was modern but simple, the furnishing luxurious, and the bed alone was enormous. It was certainly big enough for two people...

The three girls stepped out onto the balcony, watching them take in the view, as there was a knock at the door, accepting the buckets of ice with bottles inside, glad they were already chilling. There were plenty of glasses in the kitchen, opening the bottle of champagne, the girls hearing the cork pop and walking inside as I was pouring four glasses for us.

Handing out the glasses, I received a kiss on the cheek from each of them before we wandered out onto the balcony, leaning against the railing as we continued to make small talk. The girls took their time sipping at their drinks. I'd been drinking beer and didn't particularly want to mix, so I was sipping at mine as well.

"Fernanda, I need the bathroom. Come with me," Luana said. I laughed as it was typical for two women to head together, though that was usually at a pub or a club.

Sipping at my glass, I was focused on the view so didn't realise Kalena had moved until I felt a body pressing into mine from behind. Being taller than me, I glanced left and right to see her hands gripping the railing. When her breasts pressed into my back, and I felt hot breath by my cheek, I couldn't stop the shudder that flowed through my body.

"Did you invite us up here hoping to have some fun?" she whispered into my ear.

"I didn't think you'd say yes, if I'm being completely honest."

"Why wouldn't we? I think the three of us agree that you're very cute. There's a reason why we sat with you at the bar. There's no doubting you're young, intelligent and ambitious, but we also thought you were rather attractive." Kissing my cheek, she pressed hard into my body, and I almost thought I felt something poking me, but dismissed it as imagining things. One of her arms wrapped around my body and she kissed my other cheek. "We came with you hoping to have a lot of fun with you, not just tonight, but the entire time we're here."

"You're serious?" I asked, voice barely a whisper.

"I think you're going to love our company for the next few nights, Mark."

Her presence against my body disappeared, turning around to see her smiling at me, draining her glass before offering her hand. Leading me inside, Luana and Fernanda were sitting back on one of the lounges, sipping at a new glass of champagne, glancing in my direction with a smile. Neither wore their dress any longer, sheer black bras showing off tanned breasts and dark nipples, their legs crossed though I could see the band of what I assumed were panties, and thigh high stockings with heels on their feet.

"Oh," was all I managed to say.

Kalena stopped and turned to face me, running her fingers down my cheek before lifting my chin, leaning down to leave a soft kiss on my lips. Just her soft lips against mine sent my cock from six to twelve o'clock in an instant.

"The zipper to my dress is to the right. Want to help me take it off?"

Fairly sure my jaw dropped first before I managed an eager nod, earning a giggle as I ran my hands up her sides, finding the zipper and slowly lowering it down, Kalena leaning down to kiss me again as she shimmied out of her dress. Her sheer bra was black like her friends, and I could see dark and very hard nipples behind the thin fabric. Gazing down her body, she was incredibly toned, almost the outline of a six pack. Her black panties were also sheer and it was obvious that she shaved. Black thigh highs and heels also completed her look.

"Fuck," I murmured.

"Something wrong, baby?"

"Nothing's wrong. It's just... You're beautiful."

She pulled me into her body and kissed me hard, her tongue requesting and gaining entrance to my mouth in seconds. She would have felt my erection as I wrapped my arms around her, feeling the soft skin of her back, running my hands to feel what felt like an incredibly firm arse. That made her smile as she leaned back.

"I have one more surprise for you, baby," she whispered, "And something tells me that you're going to love it."

Gently pushing me back a couple of steps, she unclasped her bra at the front, the clasp between the cups, revealing a large pair of what were obviously fake but, to be honest, absolutely perfect breasts. She smiled at the reaction on my face, my imagination running wild with what I would do to those. Her hands moved down her toned body to the fabric of her panties, smiling as she turned around but glanced back as she bent forward, showing off her perfect arse as she lowered her panties.

"Show off!" Luana stated from the couch, giggling away with Fernanda.

"We know you have a perfect butt, Kalena," Fernanda added.

Kalena stood tall and glanced back at me over her shoulder. "Like what you see, baby?" Nodding rather dumbly, as I wasn't capable of speech, she smiled and slowly turned around...

To reveal a hard, long and very thick cock.

I almost wept at the revelation as she was exactly what I'd always wanted. And it must have appeared on my face as she stepped forward, running her fingers around the back of my head before she kissed me again. Completing the embrace, I felt her cock press into me as the kiss turned hot and heavy very quickly. Moving back just enough, I didn't hesitate in wrapping my fingers gently around her cock, barely able to close my fingers around the thick shaft. She smiled as she shuddered from my touch.

"You like my cock, baby?"

"You're everything I've ever hoped and wished for, Kalena."

"You like girls with big cocks?"

"I do. I've wanted to meet a girl like you for so long... But I know you're more than just your cock. You're... You're beautiful, Kalena."

"And you're rather cute right now. Your cheeks are very red."

"A million thoughts are running through my mind right now."

"Such as?"

Taking a deep breath, I met her eyes. "I get the feeling you might be a little... um... dominant?"

She smiled as Fernanda and Luana giggled on the couch. "You're more astute than you give yourself credit, Mark. I've been imagining you on your knees before me, your lips wrapped around my cock, sucking me until I came down your throat. Then we'd head into your room where I'd happily fuck you the rest of the night."

Glancing at Luana and Fernanda, they smiled at me as I asked, "And our friends?"

"Girls, I think you need to show him..."

The other two girls drained their glasses before standing up, placing the glasses on the table, before they took off each other's bras, revealing a pair of absolutely perfect breasts, before they did the same as Kalena, turning their backs and lowering their panties to the floor, before turning around to reveal their own cocks. Luana was incredibly thick but perhaps not as long as Kalena, while Fernanda was just... massive in both length and girth. Fairly sure my eyes bugged out for a few seconds, earning giggles from the pair.