Chapter 235: Tales of *r*nswomen Tops Ch. 05 by UltimateSin
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 Kayla. I'm what you call a local. The woman next to you is Lillian, she's from Argentina. And next to her is Sarah, 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," Lillian said, her accent not too thick but English was clearly her second tongue.
"What do you think of Brazil so far?" Kayla 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?" Sarah 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?" Kayla 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.
"Sarah, I need the bathroom. Come with me," Lillian 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 Kayla 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, Lillian and Sarah 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.
Kayla 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, Kayla 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!" Lillian stated from the couch, giggling away with Sarah.
"We know you have a perfect butt, Kayla," Sarah added.
Kayla 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, Kayla."
"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, Kayla."
"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 Sarah and Lillian 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 Lillian and Sarah, 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 Kayla, turning their backs and lowering their panties to the floor, before turning around to reveal their own cocks. Lillian was incredibly thick but perhaps not as long as Kayla, while Sarah was just... massive in both length and girth. Fairly sure my eyes bugged out for a few seconds, earning giggles from the pair.
I found myself naked rather quickly as the three leapt on me, their hands all over their body, Kayla eager to kiss me but I had my first kiss with Lillian next, before Sarah proved rather aggressive just kissing me, so was left thinking that, if she was as aggressive in bed, I was going to be tender afterwards. Once I was naked, I had to resist covering my groin area as I was nowhere near their size. I wasn't small, being average like most men, and my body had some definition, but compared to them...
"Can we keep him?" Lillian asked, "He's quite fit but just too damned cute, Kayla."
Blushing again, Kayla hugged me to her body, feeling her cock press into me. I felt mine throbbing with excitement as it rested against her. Sarah almost made me moan as she pressed into me from behind. "Well, I'm not sure about keeping him permanently, but we can certainly keep him company while he's here..." She met my eyes as she asked, "If that's what he wants?"
"More than anything," I whispered.
Leading me to the couch, the three girls sat down, Kayla in the middle, Lillian to her left, Sarah to her right. I knew my place, getting down onto my knees between Kayla's legs. I must have looked a little unsure, as although I'd see men give blowjobs to beautiful women like her, all I had was theory. I'd never put it into practice.
"You have lube?" she asked. Almost blushing again, I nodded and quickly hurried off to the bedroom, returning with a tube of the stuff. The three returned knowing looks. "Just get me nice and slick with your hand first. Once you're ready, just do what you think will feel good. I'll tell you what feels good too."
Lubing up her cock, I wrapped my hand around it again and slowly started to stroke her, gazing into her eyes the entire time. After only a couple of minutes, I was ready to do far more than that, running my tongue up and down her thick shaft with my fingers around the base. She moaned softly, her fingers running through my hair, as I licked her cock like an ice cream to start before running my tongue around the thick head.
"Someone seems to know what they're doing," she whispered.
"And he looks so happy," Lillian added, "Fantasy come true, Mark?"
Wrapping my lips around Kayla's cock, I glanced at Lillian and nodded before returning my eyes to Kayla. Hers gazed down at me in return as I slowly took more of her cock in my mouth until it hit the back of my throat. With her hand on the back of my head, I started to bob up and down, using one hand to stroke the rest of her cock while my other was fondling her balls.
Slowly moving my mouth up and down her cock, Lillian and Sarah had lubed their cocks and were stroking themselves off at the same time. Kayla ran her fingers through my hair, slightly moving her hips but leaving me in control, trying to take more and more of her cock with each bob. Her cock was now coated in my spit and drool, in addition to lube, and I knew already that I'd want to do this again and again.
"That's it, baby," Kayla cooed, her fingers stroking my cheek, "You like my big cock in your mouth?" My eyes had barely averted from hers, so I could smile and nod without stopping. "You're definitely going to make me cum. Will you swallow it all?" Nodding as my head continued to bob up and down, she smiled as her fingers continued to graze my cheek.
Hearing that she wanted to cum, I bobbed faster, worked the rest of her cock with my hand while fondling her balls more. She started to move her hips more, Lillian and Sarah now watching with interest, their bodies turned as they were eager to see me make her cum too. Kayla moaned more than once, warning me she was getting closer and closer to orgasm.
"Oh fuck!" she cried out, her fingers gripping my hair to keep me in place, "Gonna cum, baby! Gonna cum!"
Sealing my lips tight around her shaft, I waited to feel that first spurt of hot cum spurt into my mouth. When I did, she whimpered and I couldn't help moan, taking a moment to savour the taste before I swallowed it down in preparation for the next spurt. I learned that Kayla came hard, and she came in what seemed to be buckets as spurt after spurt filled my mouth, swallowing as fast as she filled my mouth. Her cum was thick and not as bitter as I'd been told it could be.
"Fuck yes, baby," she moaned, as I cleaned her cock, "Sure that was your first time sucking a girl's big cock?"
"I've watched a lot of porn," I admitted.
The three girls giggled. "And I can take a guess what you like to watch," Sarah stated, leaning over to kiss my cheek, "Girls with big dicks being naughty with men like you?"
"Mostly..."
Moving her lips to my ear, she whispered, "I think you should suck off Lillian next and enjoy her creamy load. Then I want to see those soft lips of yours around my cock."
"Once you make Sarah cum, we'll move to the bedroom," Kayla added, lifting my chin with a finger as she leaned forward to kiss me, "Would you like to feel my big cock inside you, Mark?"
"More than anything."
"We'll be gentle with you tonight... Girls, I'm thinking we just take turns and leave threesomes until tomorrow night."
"I just want to get my big cock in what is obviously a delightfully tight little butt," Sarah stated, giggling to herself.
Moving across to sit in front of Lillian, she leaned forward to kiss me first, her tongue exploring my mouth before I kissed down her firm body, arriving at her incredibly thick cock. I wondered how I was going to get my mouth around it, then thought if I struggled with her, I had no idea how I'd handle Sarah. Then again, Lillian wasn't too much thicker than Kayla, but there was a difference.
Teasing her to start, I ran my tongue up and down her shaft, over the thick head, and down to her smooth balls, all three girls being completely bare around their groin. Finally wrapping my lips around the thick head, I teased her to start before finally lowering my mouth as far as it could go without making myself gag. When Lillian moaned loudly, I smiled to myself as I started to work her shaft with mouth, tongue and hand.
Figuring out what she liked didn't take too long, and like my own cock, the underside near the tip seemed to be her most sensitive part. She moaned as I used my tongue there while continuing to bob up and down, making myself gag a couple of times but I could see she was thoroughly enjoying what I was doing. Kayla moved to sit on her knees next to me, giving me encouragement to take more and more of her cock.
"You love her cock too, baby?" she whispered into my ear. Meeting her eyes, I nodded as I continued to bob up and down. "We love watching a cute young man going down on us." She paused before kissing my cheek. "It's actually been a while for all of us."
"We're very selective," Sarah added, sliding closer to sit next to Lillian.
Glancing into Lillian's eyes, she met mine before they closed, and she moaned again. I felt her cock throb and I knew she was probably getting closer to her own orgasm. "That's it, baby," Kayla stated, "Suck her deep and make her cum too."
"Then you can suck me before Kayla makes love to you," Sarah added. That phrase brought me to a temporary halt, feeling Kayla nuzzle into me.
"As I said, I'll be very gentle, but it's obvious the three of us are attracted to you," she whispered, "I just want to wrap you up already and take you home with me."
Feeling myself blush, I bobbed faster and faster on Lillian's cock until she finally cried out, Kayla helping keep my head in place as I felt that first blast of hot cum explode into my mouth. Lillian moaned with each heavy spurt, eventually having to remove my mouth and letting a couple just fire into my face, which I didn't mind.
"Holy shit," Lillian stated, "Wow..."
"Not bad for a first timer, right?" Kayla asked her.
"I've had guys who have claimed to suck a million dicks not blow me that well."
Kayla and Sarah both used their fingers to clean my face, feeding me Lillian's cum, before I turned to kiss Kayla again. She smiled when we broke apart, her face lighting up, as I turned to face Lillian, who leaned forward to kiss me too, whispering her thanks for such a great blowjob. Moving to sit in front of Sarah, I took her thick, long cock in hand and simply marvelled at the size of it.
"Fucking hell," I murmured, "And you're going to stick that inside me later?"
"I'll be gentle. I promise," she replied, "I don't like hurting my lovers... unless that's what they want." Leaning forward to kiss me, her lips softer than I thought, she smiled before asking, "You want to suck my cock, baby?"
"Yes," I whispered, "But you're even thicker than Lillian."
"It'll feel so good inside your arse later, Mark. I promise."
Kayla had moved to sit behind me, feeling her hard cock pressing against me, her lips on my cheek again. "We're going to have so much fun this week, Mark," she added, "So much fun that you won't want to go home."
"I'm already thinking that, and we haven't made love yet."
Sarah smiled down at me as I ran my tongue up and down her cock. I still marvelled at the sheer size of it and wondered how many men she'd actually been with. If not men, then maybe she was also interested in women. After coating the shaft in plenty of spit, I lifted myself up enough to wrap my lips around the head and slowly work as far down her cock as I could manage.
"We'll teach you to deepthroat during the week," Kayla stated softly into my ear, feeling her rub her cock against me, "But we want to see you savour Sarah's massive cock. It's big, isn't it?" Moaning as the head of the thick cock continually hit the back of my throat, Kayla pushed her cock harder into my body, "You're already thinking about the three of us fucking you, aren't you?" Moaning around Sarah's cock, the three girls giggled. "As soon as you make Sarah cum, we'll get you nice and ready so I can slide my cock inside you."
"He can't wait," Lillian stated, "He's living out his dream. You can see it in his eyes."
"He's just far too cute for his own good," Sarah added, her fingers running through my hair, "Loving my big cock, baby?" Meeting her eyes, I managed to nod as I bobbed up and down on her cock, "I'd love to see you ride me later, just watching every inch slide inside you as you work your way down my shaft."
Each girl had a slightly different taste, particularly their cum. I'd already learned that their cum was actually rather pleasant and I knew I'd happily suck them off and swallow their cum whenever they wanted. Sarah was leaking plenty of pre-cum and I was already loving her taste, both her hand on my head as she moved her hips in time with my head.
Kayla finally helped me out as I felt her fingers wrap around my cock. I was nowhere near the size of the three girls, but she whispered into my ear that she already loved my cock and wanted to play with it later while we made love and wanted nothing more than to make me cum while she was inside me. I nearly came after just a few strokes from her.
Sarah was quite obviously loving what I was doing, my hand working her shaft faster and faster as I was swallowing as much as I could with each bob of my head. Her eyes were alive with her lust and desire, Kayla rubbing her cock against me, and I just wanted to yell out for her to slide it inside me, Lillian sat next to Sarah, stroking her cock which had remained hard even after her orgasm.
She started to babble in Spanish, a language of which I only knew a few words and phrases, so I didn't really understand what she was saying, but as she moved her hips faster, and I started to gag more often, I knew she was getting close.
"Oh my god, baby," she finally cried, her fingers gripping my hair tightly.
"Make her cum, baby," Kayla murmured into my ear, "Swallow her delicious gift."
Sarah moaned and groaned a couple more times before she held my head in place as her cock throbbed then exploded. She came so much, in such heavy amounts with each spurt, I simply wasn't capable of swallowing it all, eventually removing my mouth as her cock throbbed and bobbed, thick white cum firing everywhere over my face and her own body.
Once she stopped firing, I cleaned up her cock, running my tongue up and down her shaft to savour the taste, spreading her legs so I could give her balls some attention with my tongue as well. "Oh, that's it, baby. Give them a good lick too," she murmured.
Sitting back against Kayla, her lips moved up and down my neck and cheek before I turned so I could kiss her properly, smiling as her hand moved back to my cock. She smiled in return as I broke the kiss and simply gazed into her eyes for a few seconds. Rising to her feet, she offered her hand and led me towards the bedroom.
"Get on the bed, on all fours, sweetie," she whispered, doing as she asked, chuckling as she found the lube on the nightstand. Lillian and Sarah followed in and sat on the bed behind me, their hands exploring my arse, giving me plenty of compliments about my physique. Kayla eventually joined them, feeling her lean forward, whispering for me to relax and rest my head on a couple of pillows.
Feeling her spread my cheeks, I shuddered when I felt her tongue run over my rosebud. Lillian moved around to sit in front of me, offering me her cock to suck while Kayla got me ready, though she told Lillian there'd be no blowjobs while I was being fucked. Still, I wrapped my lips around her cock and enjoyed tasting her again as Kayla seemed to rather eagerly eat my arse. Moaning around Lillian's cock had her giggling while I felt Kayla move away and a new tongue lick me instead.
"Enjoying having your arse licked, baby?" Kayla asked. Moaning around the cock that was in my mouth, Sarah licked me for a couple of minutes before her tongue moved away and I felt a finger start to prod me. And then, without teasing me too much, I felt her slide a finger inside me.
"How tight is he?" Sarah asked.
"We're going to have fun stretching him out, Sarah," Kayla replied, "But we remain gentle tonight. Okay? No just pounding him like it's a pussy."
"You think I want to hurt this sweet thing? The three of us are going to make love to him, Kayla." She paused before growling, "Well, for the first couple of nights before he's used to taking a couple of big cocks."
One finger turned into two as Kayla positioned herself behind me again, feeling her leave a trail of soft kisses up my spine, ensuring her fingers were as deep as possible as her head ended up on my shoulder, slowly fucking me with her fingers as I kept sucking on Lillian's cock. Two fingers turned into three, earning even louder moans.
Feeling her pull them out, Lillian pulled her cock away, earning a whimper of disappointment, the three girls giggling as I was rolled onto my back. Kayla sat on her knees, her cock swaying as she lubed herself up as my legs were spread nice and wide, a pillow under my arse as she applied some more lube to me. Leaning forward, she kissed me softly, far more passionate and tender than any other kiss we'd shared until then, the head of her cock pressing against me.
"I'll be gentle, baby," she whispered, Lillian and Sarah lying to either side of us, "You're going to love this. I'm guessing this is the moment you've dreamed of."
"I've always wanted a girl like you..."
A sweet smile formed. "A girl with a nice big cock who will make love to you with it?" Blushing and nodding, all three of them kissed me. "Good thing we adore men just like you in return. The three of us think you're so sweet already."
"I try..."
Kissing me softly for a moment, she pulled back and kept her eyes on mine as I felt her press the head of her cock against me again, causing me to gasp when it ever so slowly started to spread me, and I felt her start to slide inside me. I whimpered at how good it felt, though I won't lie and say it was pain free. I'd had a finger or two up my bum when masturbating.
Kayla kissed me again as I felt hands caressing my chest, moaning as the head of her cock finally slipped inside me. I moaned loudly, Kayla smiling as she kissed my cheek. "And it's only going to feel better," she whispered, feeling her slide a little more length inside me, "You're so tight, baby."
Slowly, ever so slowly, we moaned almost in unison as she buried her thick cock inside me. I whimpered more than once, and I'll be honest, I had to keep my emotions in check, particularly once she'd buried her entire length and I kissed her hard. Kayla seemed to realise how big a moment it was, caressing my face as she started to gently thrust into me, my eyes closing occasionally as I savoured the feeling of her big cock inside me.
"Fuck, baby," Kayla groaned as she thrust a little faster, "I'm not going to last long this first time."
Running my hands down the smooth skin of her back to her arse, she smiled and kissed me again. "I want to feel you cum in me," I whispered.
Kissing me hard, she pumped me a little faster and harder. It hurt a little bit, but the pleasure was overwhelming, sensations flowing from my core to the tips of my fingers and toes. Kayla pumped me faster and faster, her lips rarely leaving mine as my fingers ran up and down her back, savouring the feeling of her thick cock pumping me. It was everything I'd hoped and spent years dreaming about. And I knew now that I'd never want anything else.
Feeling her cock start to throb, I felt a new sensation as she came inside me. Her orgasm was so powerful, I was fairly sure I felt every spurt of cum that erupted from her cock, Kayla continuing to pump me for a couple of minutes after her orgasm was clearly over before she stopped, leaving her cock buried, her eyes alive before she kissed me softly.
"How was that, baby?"
"Exactly what I've been waiting for."
Sitting back on her knees, her cock remained inside me as her body glistened with sweat, despite the air conditioning that kept cool air flowing throughout the suit. To her side was Lillian, lubing up her rock-hard cock. Kayla finally pulled out, leaving me feeling empty, though Lillian was in position rather quickly and her cock slid inside me quite quickly as I was slick from both lube and full of Kayla's cum.
Leaning forward, Lillian kissed me softly as she pressed the head of her thicker cock against me, smiling as she slid into me perhaps a little easier than other men that she might have been fucking for the first time. Still moaned like hell as she slid inside me as she was a little thicker than Kayla, and I still had Sarah to make love to me next.
Thankfully, she was as gentle as Kayla until she was buried entirely, looking at me with a satisfied grin as I shuddered. "How does it feel, baby?"
"Different but just as nice as Kayla." Looking at her, I added, "Sorry I didn't cum while you were fucking me."
Giggling, she was lying next to me, turning my head to kiss her. "Baby, I got to cum in you. You can cum whenever you want. Now, Lillian, make love to our new friend."
With my hands running up and down her back, Lillian started to slowly pump me, though she quickly had one of her hands wrapped around my cock, whispering that she wanted me to cum in preparation for when Sarah finally fucked me. As I moaned and my entire body seemed to shake, I knew my orgasm wasn't going to take long in arriving, Lillian kissing me hard, making me grunt when she picked up the pace rather quickly.
"Fuck him, Lillian!" Sarah cheered.
"You can make him cum, but he's going to cum with my cock inside him later," Kayla added, "I want to see him cum too."
"Cum for us, Mark," Lillian groaned, pumping my arse with her cock, "You've made us all cum already."
Lillian's eyes sparkled as she leaned back, still fucking me but focusing on stroking my cock. Sarah turned my head so I could kiss her, and with all the attention now on me and my orgasm, it didn't take long until I erupted all over my bare chest. What I didn't expect was for Lillian to stop moving, leaving her cock buried, as Kayla eventually leaned over and started to lick my chest.
"Mmmm. Tasty," she murmured, "Okay, Lillian, time for you to fill him up too."
Leaning forward, she lifted my arse slightly, one of my legs over her shoulder, as she resumed thrusting. Now that I'd cum, I could just lie back, move my hips in time to her thrusts, and just focus on how wonderful it felt having a big girl dick sliding into me. Thrusting faster and faster, I could almost sense that she was getting close to an orgasm.
"Fuck yes," Lauan groaned, driving faster and faster, "Going to fill you with even more cum, Mark."
"Fill him up, Lillian!" Kayla cheered.
Lillian did just that a couple of minutes later, her cock so thick in my tight arse that I felt each pulse. Lillian's face was a picture of delight as she kept driving until she was done, kissing me softly before she slowly pulled out, feeling my arse gaping for a few seconds as I was giving a couple of minutes to relax and catch my breath.
"Want a different position?" Sarah wondered.
"Honestly, I've always wondered what it would be like to be fucked from behind," I replied.
"Up on your knees, baby. Kayla, I know we said no..."
"Want my cock again, baby?" Kayla asked. Nodding eagerly, she giggled as the three of us got into position, Kayla relaxing in front of me as I felt Sarah get into position behind me, resting her cock between my cheeks, leaning forward to leave a trail of kisses up my spine until her lips were by my ear. "Good thing you have plenty of cum already inside you as lube," she whispered, "Are you sure you want to try, sweetie?"
"Sarah, I've always fantasised about a girl like you with what is simply an enormous cock making love with me..."
"Okay, baby," she whispered, "I'll be gentle to start but I might get a little worked up once I'm inside you."
"Suck on my cock as a distraction if it starts to hurt," Kayla added, leaning forward to kiss me softly, "But I know you're going to absolutely love it when Sarah does start to slam her big cock deep."
I waited until Sarah was pressing against me, glancing back to see her beautiful smile, as the head of her incredibly thick cock started to spread me even wider than Kayla and Lillian. I gripped the sheets tightly as Kayla sat up and kissed me on the cheek as I groaned loudly. "Holy shit," I whispered.
"It's okay, baby," Sarah murmured, rubbing my back affectionately, "The first insertion always hurts, no matter what."
I grit my teeth as the head slowly slid inside me, Sarah giving me a few seconds to get used to it being inside me before sliding the rest of her length. Honestly, it felt like she was rearranging my guts as inch after inch slid inside me, Kayla gently stroking my face with her fingers, Lillian sitting beside her, watching her friends look after me.
When I felt Sarah's body bump into my arse, knowing her entire cock was inside me, I released a deep breath as I felt completely and utterly full. "Good boy," Sarah whispered, "I'll start slow, baby, but I really want to fuck you, allow you to really enjoy my big cock."
Feeling her pull back until only the head, she slid back inside me until her cock was buried once again. Pushing my arse lower, I felt her lean forward with her large breasts pressing into my back as she slowly started to fuck my arse. Though there was still lingering pain, the good vibes passing through my body, left thinking I might just have another orgasm.
To distract myself, I lowered my mouth around Kayla's cock, loving the soft moan she released as her fingers immediately started to move through my hair as Sarah thrust a little faster but keeping it as gentle as possible. Moaning around Kayla's cock seemed to please her, her whispered words in Portuguese sounding rather affectionate. When I glanced up, the look in her eye's suggested feelings were already developing. Might sound strange, given I was being fucked by someone else, but I'd felt that spark the moment she sat down next to me at the bar.
"So tight," Sarah moaned, "Girls, we have to spend as much time with him as possible."
"Maybe a night alone too?" Lillian added, glancing to see her stroking her cock.
"I'll be happy just to have him suck me off all night," Kayla groaned.
I spent most of my time teasing Kayla and her delicious cock as Sarah fucked me. I was surprised at how quickly I got used to have her incredibly thick cock inside me, reaching underneath to stroke myself at the same time, my cock almost achingly hard as Sarah's cock was touching everywhere inside me that would no doubt set me off.
Feeling her lean back, she grabbed a shoulder and started to fuck me harder. Wrapping my lips around Kayla's cock, it was a good distraction, but no-one would have forgotten about being fucked by Sarah and her enormous cock.
"That's it, baby," Sarah moaned, her hand squeezing my shoulder, "Loving my big cock?"
Moaning around Kayla's cock, my head bobbing faster and faster, the three of them giggled. "I think he's loving it, Sarah," Luisa suggested, "As much as Kayla is loving that talented mouth again."
With both hands on my shoulders, I lifted my mouth from Kayla's cock and glanced back at Sarah. I knew it was probably going to hurt but part of me couldn't resist meeting her eyes, seeing her smile at me as I moaned, "Fuck me, Sarah."
"You sure, baby?"
Nodding, I replied, "I want to feel you cum too."
As she started to pump me, she moaned, "And I cum in buckets. You'll be dripping with our cum all night."
Resting my head on Kayla's lap, Sarah had her hands at my hips as she really started to drive me, one of her hands eventually moving to my lower back, pushing me lower to the bed as she leaned forward again. This time, she started to really drive her cock home, grunting and groaning with every hard thrust. The pleasure was overwhelming, but it also hurt at the same time. Kayla stroked my cheek and whispered encouraging words, Sarah leaning down to kiss my cheek at the same time.
"I'm close, baby," she finally moaned, "Going to fill your arse up!"
"Do it!" I whimpered, "Cum in me too!"
Sarah grunted a couple of times before I finally felt her unload inside me. Her cock was so thick, I easily felt each pulse of it as she unloaded. I didn't even bother counting how many spurts of cum she deposited inside me, her hands gripping my shoulders tightly while she came hard. When her cock finally stopped throbbing, she left it buried though did half-slump onto my back while I couldn't help taking Kayla's cock back in my mouth for a couple of minutes.
Feeling Sarah sit up then pull out, she grabbed my cheeks and spread them wide, hearing her giggle. "That is one well fucked and full of cum type of arse I love to see," she stated, giving each cheek a gentle slap, "How are you feeling, Mark?"
"Properly well fucked."
Lying on my back, Sarah sat on her knees between my legs, stroking her semi-hard cock, Kayla and Luisa to either side of me, a hand each creasing my cheek. When I yawned, Kayla asked if I was tired. Having been properly fucked by the three of them, I admitted to feeling rather tender and in need of a rest.
The suite came with an enormous bathroom, including the sort of shower cubicle that had two heads and more than large enough for the four of us. The three took great pleasure in washing me up and down, fingers probing my arse as I was leaking plenty of cum, Kayla eventually taking the nozzle to give me a rather good clean.
After drying off, we sat in the living room and enjoyed another glass of wine, making small talk, thankfully not awkward considering I'd just blown and then been fucked by the three of them. Luisa eventually suggested it was time to go, she and Sarah getting ready, but Kayla didn't make a move. I had a feeling what was up, so once they were dressed, I escorted them both to the door. Hugging me tightly together, they kissed my cheek, thanked me for a great night, and promised they'd catch up with me the next day.
Closing the door after they'd gone, I turned around to see Kayla barely a couple of paces away. Without hesitation, she was all over me, forcing me back against the door as her tongue was in my mouth, her hard cock pressing against me again. "Want to ride me?" she asked, "I don't want to sleep just yet, but I wanted to be selfish and have you to myself."
"Kayla... You can stay all week..."
"Really?"
"I would have asked all three of you but..."
When she blushed, I knew something else was coming. Taking my hand, she led me back to the bedroom, lying on her back as she gestured for me to straddle her lap. Feeling her cock underneath me, I leaned down and kissed her again, chuckling as her fingers ran up and down my back. When I pulled away, I don't think anything could have wiped away the smile.
"I saw you first, to be honest, and I was attracted immediately. I might have followed you round, making sure I was in any conference or meeting you were attending. I saw you giving advice and helping people out, so I learned not only are you very well informed but so willing to help others. Add to that you're just unbelievably cute and I just had to take a chance..."
"I'm glad you did. This has been the best night of my life."
That earned a lovely smile as she caressed my cheek. "Want to ride me nice and slow?"
"I'd love to!"
After applying lube where it was required, I held the base of her cock and my arse was still ready and willing to take her cock. Once I'd slid my way down her entire length, we moaned in unison as her hands moved to my hips as I started to rock myself on her cock while stroking mine at the same time. Kayla started to move, bending her knees so she could thrust up into me. I felt her cock hitting my prostate, and I knew I might be able to cum without touching myself for much longer.
"I might cum if we switch," I moaned.
"I'm loving watching you, but you think from behind?" Nodding eagerly, we quickly repositioned so I was on my knees, moaning together again once she was behind and inside me, making sure I was almost lying flat on the bed as she started to pump my arse hard. It felt absolutely fantastic. I loved feeling her hot breath on my neck. Her soft moans in my ear. But her cock slamming my arse?
I came hard, whimpering and moaning as I soaked the bedsheets in my spunk. Squeezing her cock during my orgasm urged her on to fuck me harder. "You're mine all week, Mark," she groaned into my ear.
"How about longer?"
She was silent before she left her cock buried inside me. "You mean that?"
"I can take a holiday... Maybe stay a little longer?"
I ended up on my back, legs wrapped around her as she resumed fucking me, her eyes a conflict of emotion. "Please stay," she whispered before kissing me, "Even if it's only a couple of weeks..."
"What about your friends? I wouldn't want to hurt them."
She giggled while fucking me. "They'll have fun while we're here. But if you come home with me..." A smirk formed before she kissed me, "Well, I have a lot of friends who'd love to meet you. But you'd be in my bed every single night."
We fell silent as I focused on Kayla's thick cock burying itself deep inside me and she focused on how great my tight arse felt. Making out constantly, running my fingers through her long dark hair, we chuckled as we moaned together time and again, my legs tight around her body as I didn't want her to finish anywhere except inside me.
"Every... single... night," I moaned as she pumped me harder, feeling how close she likely was to orgasm.
"Your arse is ours while we're here," she grunted, slamming her cock harder, knowing she was on the brink, "But when I take you home, your arse is mine unless I loan you out for a few hours."
"Fill me again, Kayla."
"I'm going to keep you full all week, baby. You're going to be addicted to my cum by the end of this week."
Feeling her cum inside me again, I clutched at her body as I felt what was already a familiar sensation of a girl leaving another load of her warm, thick cum deep inside me arse. She moaned softly and hugged me back, neither of us wanting to let go, and I kept moving my hips as she kept slowly thrusting long after her orgasm finished.
"Fuck," she finally moaned, "I haven't felt like this about anyone I've met in so long."
Lifting her head, she kissed me again before leaning up enough to meet my eyes. We exchanged smiles as she pulled out, her cock glistening in the light of the lamp to either side of the bed. Lying on her side, I turned onto my side to face her, enjoying it when she wrapped an arm around me and pulled me closer.
"Okay, now I'm tired," she stated, "You tired, baby?"
"I was tired before, but I really wanted to just have time with you alone."
"I wanted that too."
Spooning back against her, I giggled as her cock was still hard somehow. Feeling her arm around me, her, I snuggled backwards, feeling her breasts against my back, her cock poking my lower back. I'd always wanted to be the little spoon in the arms of a strong woman. To say it was one of the best nights sleep I could remember wasn't an understatement.
Waking Kayla the next morning with a blowjob had her smiling before she exploded, gulping down her cum. Licking her cock clean afterwards, she gazed down at me with a dreamy smile on her face. "If you want to wake me up like that every morning..."
"I'll consider it my morning dose of protein..."
I had another protein injection in the shower later as I always had two types of lube with me, one for using in the bedroom, another to use in the shower. As we showered together in preparation for the day, we were both still rather horny and she ended up fucking me against the tiled wall, bending forward to rest my head against the cool tiles as her cock slammed me nice and hard, lasting quite a while thanks to my blowjob before eventually leaving a load inside me.
I dressed immediately afterwards, making her giggle when I added that I planned to carry around her load all day. "And if I added a fresh batch at lunchtime?" she wondered.
"Kayla, just let me know where you want to meet. I'll suck your cock or bend over and beg you to fuck me."
She blushed and glanced away as we ate breakfast together on the balcony. Taking her hand, her eyes moved back to mine. "I've never met a man like you before... I'm not feeling used here..."
"I'm not getting ahead of myself, Kayla. We're from different countries, and long distance..."
"You'd like to try that?"
"We've only spent one night together, but I'm willing to go with you to wherever you live after this and see how we get along."
Walking towards the conference centre a few minutes later, Lillian and Sarah were waiting at the entrance we were approaching, greeting both of us with a kiss on each cheek. Both of them smiled at Kayla, noticing how she was holding my hand. "Really like him, do you?"
"I do but we're going to share him the rest of the week, as agreed."
Sarah looked at me. "I'm thinking we have some proper threesomes and... maybe we could even try double anal later this week?"
"To be honest, I'm willing to try anything with you girls except one or two I'm hoping obvious things."
"Baby, as long as you suck my cock and love being fucked, you'll find I'm a rather easy girl to get along with," Sarah stated.
"The only fetish I have that would be considered a kink is peeing," Lillian admitted.
Shrugging, I replied, "As I said, there are only one or two obvious things."
The three of us looked at Kayla, "And you, sweetheart?" Sarah wondered.
"I'm looking to fall in love with someone." Squeezing my hand, she kissed my cheek. "Ask any girl and all they'll tell you is they want a man with a good heart... and a tight arse."
Laughing away, we entered the conference centre to resume our work. It was just the start of a fantastic week together with three beautiful women, before I joined Kayla in her home city for two weeks of sun, sea, sand and endless amounts of sex. The sort of fortnight with a woman that would change my life for the better.