XXXMAS Day Twenty-Six - Crossdressing

Story by ThatDarnDodo on SoFurry

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#26 of XXXMAS

Summary: Gus wins a one on one session with his favourite cam boy. They have a heart to heart and then the dildo comes out.

So, what is XXXMAS? For every day of the month of December I will post a short story, each featuring a different kink that was randomly chosen by several kink generators I found online. I'm doing this as a sort of writing challenge, test my skills with the help of some very different kinks and themes, as well as to build up a sort of writing portfolio. Each story is completely unrelated so you can skip whichever ones aren't your cup of tea.

I don't have much to say this time other than I am tired and so happy we're coming to the end of this challenge. I cannot believe I actually got this far.


Gus was a man's man. He was athletic, worked as a mechanic and enjoyed a beer with his mates on the weekend while watching rugby. All in all, he was a masculine guy that enjoyed masculine things. At least, for the most part. You see, Gus the husky had a secret, one that would earn him much ridicule from those around him. He was gay. He was as gay as a purple unicorn riding a rainbow while singing Dolly Parton's greatest hits. Sure, there wasn't anything stereotypically gay about him but not a day went by where he didn't imagine what it would be like to have a dick in his mouth which, sadly, had never happened.

Living in a religious small town, he'd had to hide who he was by dating women, his dreams of being with a man having to be shoved aside only to live in his imagination, never in person. But even if he couldn't be with an actual man then at the very least he had his porn.

He loved watching cam boys, one man in particular, a Siamese femboy by the handle of CutieKitty. Cutie was a slender thing, always decked out in the nicest lingerie and the most flattering makeup. Gus watched his cam shows whenever he could, always giving him a little tip when he could afford it.

It was the black and white husky's dream to have a private show with him but he just didn't have the money for it. Cutie was a popular guy and his cam shows ran for more than Gus could really afford to give on his salary. It seemed that having a one on one session with his dream boy would be just that, a dream. At least, it was until Cutie decided to have a raffle. He'd pick one of his subscribers at random to have a private show with and, wouldn't you know it, Gus won. He'd finally get to have a private session with his dream guy.

Gus sat cross-legged on his bed in nothing but his blue boxer briefs, wondering if maybe he shouldn't have worn something more. What was the etiquette for something like this? He wasn't under dressed, was he? He was going to jerk off in front of the guy so less was more, right? Gus groaned as he scratched the back of his head. He'd never done this before and he was terrified of looking like an idiot in front of a guy he, admittedly, had something of a crush on. Yes, catching feelings for porn stars was stupid but he couldn't help himself. CutieKitty was gorgeous and really friendly, always wearing a smile and shooting the camera a wink that made his heart melt.

Gus' heart jumped into his throat when he saw the notification for an invite to a private session popped up onto his laptop screen. He clicked accept and held his breath.

A slender Siamese popped into view. He wore purple and white knee length striped socks, a black skirt, a tiny purple bikini top that barely covered his nipples, along with black lipstick and purple eye shadow. He was going for a bit of a gothic-light thing that day and Gus had to admit he was digging it.

"Hey, you're HungryHound123, right?" he said in an androgenous sounding voice that could be mistaken for a woman's by those not in the know.

"Y-yeah! That's me. Uh, hi, huge fan." He chuckle nervously. "I can't believe I actually won. I've always wanted to have a private session with you but, you know, money and all that."

Cutie giggled, "You're cute. And no need to be nervous, big guy. We're all about having fun here."

Gus' cheeks had turned a lovely shade of crimson at being called cute. "Sorry, I'm just really nervous," he said as he looked downward, too embarrassed to looked Cutie in the eye.

"Aw, don't be. I promise I don't bite." He shot Gus a wink. "If you want, we can talk for a bit first. Get to know each other before we get to the real fun stuff. Think that'll calm you down?"

"Uh, maybe? What should we talk about?"

"Well, tell me a bit about you. Do you work out? You look pretty buff."

"Oh, uh, sometimes," he said with a nervous chuckle. "Okay, a lot, actually. I live in a pretty small town and there's not much to do around here so I often go the gym the next town over."

"Your town doesn't even have a gym?"

"Honestly, it feels more like a village than a proper town. That small. The only fun thing is the local pub and this nearby large field where we play soccer."

"No offence, but that sounds terrible."

With a laugh, Gus said, "None taken. It does get pretty boring."

"Is it one of those everyone knows everyone kind of places?"

"Yeah and, well, it can be nice, it can also be pretty shitty. Everyone knows everyone else's business and all that. Kind of hard to have a private life. Especially when you're in the closet," Gus said with a sigh.

"You're still not out?" Cutie asked.

"Oh, um, yeah, kind of hard to be. This place isn't exactly the most inclusive. Was saying I'm in the closet TMI?"

Cutie giggled, a sound that made Gus' heart skip a beat. "Honey, I'm gonna show you my dick later. There's no such thing as TMI here." He then gave him a sincere smile as he added, "I can't imagine how hard it must be for you. I grew up in a big city and went to a pretty liberal school. Things weren't always easy but I had a community."

"Community." Gus gave a sad smile as his gaze seemed to look off into the distance. "Sounds nice." He shook his head as he added, "Damn, I'm making things depressing, aren't I?"

Cutie shot him a gentle smile. "You wouldn't be the first guy to open up during a private session. I get it, sometimes you want someone to vent to who gets it. Sure, I never lived in a small town but being gay is hard wherever you are. It wasn't all sunshine and rainbows for me either, especially with how I look."

"You mean drop dead gorgeous?"

Cutie laughed. "My, aren't you the flatterer?" With a smile that looked a little pained he added, "Being so feminine made me an easy target for bullies growing up. Everyone wants to beat up on the girly boy. But I suppose it hasn't been all bad. My lovely legs and slender hips now help pay for my pretty bitchin' apartment. Who's laughing now, high school bullies?"

Gus couldn't help but laugh as well. "The best form of revenge is living successfully, huh?"

"You know it, handsome," Cutie said, shooting him a wink.

"Damn, I wish I had your confidence to be as open about all of this as you are."

"Don't worry, honey, I'm sure you'll get there one day. I used to be a bit of a shy one myself as a kitten. It took years to grow into my fabulous and outgoing ways. Don't worry, you'll get there one day."

Gus had to admit that CutieKitty's words were making his heart swell. With a nervous chuckle, he said, "Aren't I supposed to be jerking off or something? Can't believe I'm getting a pep talk instead. But, damn, it actually is pretty nice to talk to someone who gets it."

"Totally. Although," Cutie leaned against his bed's headboard, legs spread wide as he lifted his skirt to reveal he was wearing a purple thong underneath. "We can totally get to the jerking off part whenever you want."

Gus felt his cock twitch at the sight. "I'm okay with that," he said as he stared at the cat's groin in a daze.

"What would you like me to do, handsome?"

"Oh, um, let me think," Gus said as he scratched the bad of his head in thought. Over the months he'd been watching him in his public sessions, he'd had so many ideas about just what he'd want him to do if they ever had a private chat. He had him now and all previous ideas had been thrown out the window. He couldn't remember a single thing he'd wanted. So, doing his best to try and think up something, he blurted out, "Chest! Do, uh, something with your chest. Take off your top or something?"

"If that's what you want, handsome," CutieKitty said as he removed his bikini top, tossing it somewhere off screen.

Cutie's nipples were dark against his light fur, like a lovely little pair of bullseyes. "Like what you see?" the asked when he caught the dog staring.

"Sorry, it's just different from your public sessions. Knowing it's for me and me only is, well..."

Cutie giggled. "No need to apologise, handsome. Giving you a good time is what I'm here for, after all. Anything specific you want me to do or should I just wing it?"

"Um, wing it, I guess?"

"All righty, honey, just tell me if you think up anything naughty for me to do. And, remember, I've got plenty of toys to use, too." He bit his lip as he shot Gus another wink, the dog's mouth growing dry as Cutie decided, seeing as the bikini top was gone, why not have a little fun with his nipples first?

He placed a delicate hand on his flat belly, slowly sliding it up until he reached a pec. He pinched a nipple between his index finger as his thumb, rolling it between the digits, all the while not breaking eye contact with Gus. The husky was already feeling a tent building in his underwear and just that sight, unable to help the little whimper that escaped his throat.

"Aw, what's wrong? My little doggy thirsty already? I know what would wet those lips of yours," Cutie said as he made sure his skirt was pulled up far enough so that Gus could see the lovely little bulge pressed up against his purple thong. He then proceeded to take off said thong, tossing it to join wherever the bikini top had landed.

"Holy shit," Gus groaned at the sight of Cutie's flaccid member, barely able to contain his excitement at seeing it grow as he played with his nipples.

"You like what you see, doggy?" Cutie said with a mischievous smile, Gus nodding vigorously in response. The cat curled his fingers around the base, slowly pumping himself while his eyes were still trained on Gus. "Wish you could lick it?"

"Oh, God, yes," Gus moaned. Unable to take it anymore, he pulled down his boxer briefs enough so that his hardening cock flopped out, earning him an impressive hum from CutieKitty in return.

"Looks like our little doggy's packing. Well, not that little," the cat giggled.

The cam boy's words helped in giving Gus that little extra bit of confidence he needed to actually participate, him managing to stutter out a, "Y-you like that, huh?"

"What can I say? I've always had a thing for bigger guys. You seen me use my toys, right? They're not exactly small."

Images of past memories involving seeing Cutie using his various dildos and vibrators ran through Gus' mind, causing him to groan and for his dick to twitch like crazy in his hand. "Could you, um," he tried to say, his embarrassment over the whole situation flooding back. Then, with a deep breath, he managed to bring himself to say, "Could you play with your arse? I want to see you fingering yourself while stroking your cock."

"That can be arranged," Cutie said as he let himself go to reach over to his nearby nightstand, pulling out a little clear bottle of liquid from the drawer. He coated a healthy amount over both hands, absolutely covering himself in what Gus had to guess was lube. He put the bottle away and then wrapped one hand around his base while the other moved towards his entrance. He slid is index finger in with ease, giving it a few pumps before quickly adding another. The guy had experience, so two fingers at once weren't exactly going to hurt.

CutieKitty continued to finger himself while he pumped his cock, both hands going achingly slow. Gus' fingers, now wrapped around his own cock, was moving in time with Cutie's strokes, imagining it was his hand on him. "Could you go a little faster?"

"Impatient, are we?" With a sultry smile he did as he asked, his fingers in him and around his dick picking up pace, Gus moving faster along with him.

"Fuck, you're hot, you know that?" Gus said with his eyes glued to the cat's cock.

"You're not so bad yourself, doggy," Cutie shot back.

Gus relaxed into his pillows, simply enjoying the sound of lubed up fingers against skin and the soft sighs of pleasure Cutie was letting out that was music to his ears.

It wasn't long until it just wasn't enough anymore and Gus couldn't take it anymore as he said, "I want to see you use a toy. Make sure it's as close to my size as possible."

"Little doggy getting bold and giving orders now? Me like."

Cutie stood up and moved off the screen somewhere, Gus hearing what sounded like the opening and closing of drawers before the cat flopped back down onto the bed, a purple phallic shaped toy now in his hand. "I'd say this looks about the right size," Cutie said as he wiggled the toy in hand.

CutieKitty spread his legs and wasted no time in pressing the tip of the toy against his lubed up and stretched hole. With a lick of his lips he pressed in harder until it was half way in, Gus' hand stopping halfway like the dildo did. Cutie pulled it out, Gus following along with it. Then, he shoved it in all the way to the base in one go, groaning along the way. He'd seen the cat take bigger in one go so him being able to handle it shouldn't have shocked him. Still didn't stop him from sitting there slack-jawed.

"You really know how to take it, don't you?" Gus said without thinking.

"Wouldn't be good at my job if I couldn't."

As if to emphasis his point, he pulled the dildo out until only the tip remained before slamming it all the way back in with such force it left the man a quivering mess.

"Went a little too hard there, babe?" Gus said with a chuckle.

"As if," Cutie said with a huff and a smirk before he pulled the toy out and, a little slower than before, pushed it back in.

CutieKitty continued to fuck himself with the toy as Gus pumped his cock, eager eyes latched onto the femboy. "Shit," Gus gasped as his hand's actions grew erratic, already feeling himself close.

"Almost there, doggy?" Cutie said with a lick of his lips.

Gus let out a growl as his cum shot out his tip to splatter all over his laptop screen. With a low moan, Cutie was soon also shooting his load.

The two sat their in silence for a moment before Gus grumbled as he saw the state of his laptop, "Seriously? Shit, I hope it doesn't get into my keyboard or anything. That would not be a fun conversation to have with the computer repair folks."

"My H key keeps getting stuck before I got jizz in it. Think you can fix it?" Cutie said in a voice imitating Gus.

Gus couldn't help laughing. "Oh, God, that would be awful." Then, awkwardly rubbing the back of his head, he added, "And, um, thanks. For earlier, I mean. I can't believe I spent half our session opening up like that."

"Hey, no problem, handsome," Cutie said with a wink. Then, with a genuine smile, he said, "You know, I really like you. If you want, how about I give you my personal email and we can chat some more?"

"Y-your personal email? Not the email you have posted on your profile?"

"No, that's for work," Cutie said with a wave of his hand. "Like I said, I like you and I wouldn't mind having more personal chats. If you want to, that is."

"Hell yeah I do!"

Cutie laughed and, with one final wink that made Gus' heart flutter, he said, "And my real name is Skylar, by the way."