NOTES: This story features my recurring “Oz Beach Boy” character Matt in his slightly younger years, and includes CFNM, female-of-male body worship, and anal sex. All of the characters are over eighteen. This is a complete work of fiction. I am endeavouring to gradually write a CFNM “Oz Beach Boy” story in every Literotica category. This, ahem, entry: “Anal”.

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It was a wet, dreary autumn day in Sydney, Australia. 30-year-old Ruby Sanderson quickly straightened her black blouse over her big, full breasts, and then knocked firmly on the door of the run-down old house in front of her.

When Ruby heard sound and movement coming from inside, she smoothed back her curly blonde hair, and let her pretty face settle into the easiest, friendliest smile she could muster. Ruby heard the lock and handle move on the other side of the door.

“Hi,” said a smiling young man as he opened the door, and Ruby’s jaw nearly dropped open comically. “Can I help you?”

Dramatically handsome with long, straight, sandy-brown hair that hung way past his broad shoulders, the young man was clad in just a pair of light grey sweatpants.

His body was lean, muscular, and slicked with sweat. A thick smattering of hair covered his marbled pecs, ran down his rock-hard abs, and then continued sexily into the top of his pants.

“Oh, hello, yes,” Ruby said, desperately trying to collect herself, not just at the joyous sight of the young man’s chiselled, model-like face, but also at the wonders of his muscled torso.

“Are you a friend of Paolo’s?” the young man asked with a smile. “Or Cecile’s?”

“No, no,” Ruby smiled. “I’m Ruby Sanderson from Urban Data Analytics. We’re door knocking on behalf of Transport NSW as part of a comprehensive survey on public transport in this area.”

“Oh, right,” the young man said, and ran his fingers suggestively down his corrugated abs. “How can I help?”

“Are you over eighteen?” Ruby asked quickly. “Do you use public transport in this area?”

“I’m 21,” the long-haired young man cheekily smiled, and then hooked his thumb into the top of his sweatpants, the weight of his hand pushing them down just enough so some of his thick spread of light brown pubic hair was clearly visible. “And yes, I catch buses around here all the time. I’m saving up for a car at the moment.”

“Okay, great…would you like to do the survey?” Ruby smiled. “It’ll take about ten minutes.”

“Yeah, sure, why not?” the young man smiled warmly. “I’m not busy. Come in.”

“We could just chat here in the doorway,” Ruby suggested, following the safety policies of Urban Data Analytics. “It’s just ten minutes of your time.”

“It’s raining a little bit,” the man smiled naughtily. “And I’m getting a bit cool just wearing these sweatpants out here with no shirt. Come on in…it’ll be fine.”

Ruby pondered the situation for a few moments. When she started with Urban Data Analytics two months previously, her supervisor had made it clear that entering the premises of survey participants was not advised.

“If you go inside,” Ruby’s hilariously brusque boss, Patricia, had barked at her, “these blokes will have their pants down and their joysticks out before you can ask the first question. There are a lot of perves out there. Some might flash their dicks in the doorway, but at least you can take off. You’re a pretty young thing, and you’ve got a big set on you too, so you need to be careful.”

Ruby was supplied with a press-button safety beacon, which sent a message back to the Urban Data Analytics offices if she was in any sort of trouble. In her two months of survey taking, only one man had acted suspiciously.

Likely aged in his fifties, the man came to the door wearing just a towel and a smarmy grin. Ruby instantly noticed that he was unimpressively erect underneath the towel.

At the sight of his lurid smile and flabby body, Ruby excused herself immediately and briskly walked off down the street with the older man’s sleazy laughter ringing in her ears.

“Where are you going, love?” the man called out. “You’re the one that knocked on my door!”

The experience with this older man had been unsettling and unpleasant, but it certainly wasn’t enough to turn Ruby off survey work, which she had been enjoying.

Ruby would have been quite happy, however, for this handsome young man to drop his pants and display himself for her. She guiltily imagined his penis and testicles to be just as gorgeous as his face and body.

And his butt…oh, my god, his butt… Ruby could barely control herself while she briefly fantasised about how wonderfully taut and toned his derriere must be under those flimsy sweatpants. God, how she wanted to see it.

“Come in,” the man smiled. “Get in out of the rain, Ruby.”

“Okay,” the 30-year-old said after a brief pause. “That would probably be more comfortable.”

“I’m Matt,” the long-haired young man said, and then turned to walk into the house. “Follow me, Ruby Sanderson.”

Ruby shuddered with excitement as she watched the muscles in Matt’s back and shoulders stretch and undulate as he walked casually down a narrow hallway and towards a small kitchen. His long hair tumbled down his back and swayed sexily from side to side as he walked.

With a naughty smile, Ruby imagined pulling Matt’s flimsy sweatpants down right there and then, and rubbing her hands all over his freshly exposed butt. She almost giggled at the wondered, and then tried to keep her objectification of this handsome younger man in check.

“Have a seat at the kitchen table,” Matt smiled, and pointed to a cheap looking chair next to an equally cheap looking dining table. “Sorry, the place is a dump…Paolo and Cecile are backpackers from overseas, and I’m basically broke. We don’t have much, and what we do have is cheap.”

“Are you a student?” Ruby asked warmly. “Or unemployed?”

“I’m doing a few IT courses right now, and I’m working different jobs…I’m just trying to make ends meet, you know?” Matt explained. “I’m trying to get my shit together.”

“Have you thought of modelling?” Ruby asked, and then instantly regretted asking such an inappropriate question…but she’d already gone there, so the 30-year-old simply pushed on. “You’re very handsome, if you don’t mind me saying…and you have a wonderful physique.”

“Oh, thank you,” Matt smiled. “That’s very nice of you. You’re very pretty too, Ruby. I hope you don’t mind me being so under dressed…I was just working out.”

“Oh, no, that’s fine,” Ruby said. “Make yourself comfortable…we’re in your home.”

Ruby was thoroughly enjoying flirting with the very handsome Matt, who was shamelessly playing up his sexy young coquette status, just stopping short of fluttering his eyelashes at the pretty older woman sitting in his kitchen.

As Ruby gazed at the shirtless young man, she started to fantasise once again about what she’d like to do to him…but even more profoundly about what she’d like him to do to her.

And as with all men that Ruby lusted after, that involved one thing: fucking her in the butt. Ruby loved having her pussy licked, and she loved traditional intercourse, but more than anything, she loved anal sex.

Ruby’s first serious boyfriend — a cool, caring guy called Dane Hocking — had told her that she had the most fuckable arse he’d ever encountered, and the then 22-year-old had tried to live up to that praise at every turn.

With her shoulder length curly blonde hair, big, round blue eyes, full red lips and perfectly straight white teeth, Ruby Sanderson was indeed a very attractive 30-year-old woman.

Ruby was short, but her body was literally built for sex. She had very big, incredibly fleshy but still firm breasts, a flat stomach, and a truly incredible butt.

Ruby’s backside was big, round and curvy, and it wobbled with extraordinary pneumatic sexiness when she walked and moved.

Though fleshy, Ruby’s butt was smooth and totally free of cellulite or any other blemishes. It was a large, gorgeous bubble butt, the kind that men liked to sink into and never leave.

The 30-year-old would often feel men’s eyes on her posterior when she walked down the street, and she had no issue with the attention. Ruby liked it when men looked at her, and especially when they looked at her butt…it made her feel sexy and in control.

“Your butt is fucking amazing,” Dane had told Ruby all those years ago. “When you’re not here, I jerk off thinking about it. I want to get up there. Have you done anal before, sweetheart?”

“No, never,” the 22-year-old replied, “but I’d like to try it. Take my arse, Dane…it’s all yours. Fuck me in the butt.”

Excited and aroused, Ruby and Dane then made passionate love on the lounge room floor of the small apartment they shared. With obvious relish, Dane lubed his girlfriend up and then took Ruby in the butt for the first time.

The feeling of fullness and violation turned the young woman on like nothing else. Wildly, uncontrollably aroused, she brought herself to a shuddering orgasm with her fingers while Dane worked on her from behind.

“I’ve never been in a butt-hole like yours before,” an exhausted Dane said breathlessly afterward. “It’s looser…it’s still tight, but it’s almost like you’ve got another pussy. I didn’t have to ram myself in there like I have with other girls. That was fucking amazing. Did you like it?”

“I loved it,” Ruby said sincerely. “It felt a bit weird, but I really, really loved it.”

When Dane first gloriously penetrated Ruby’s sweet, virginal butt-hole, it undeniably unlocked something in the then 22-year-old. It provoked physical sensations and emotional feelings that she’d never experienced before, and Ruby liked it.

Dane and Ruby enjoyed frequent anal sex during the remaining year of their relationship, and Ruby then encouraged all of her subsequent sexual partners to anally penetrate her as well.

Some were shocked when the sweet-natured Ruby suggested it, but none refused, and the sexually curious young woman grew to love it more and more.

Ruby took it from behind in all sorts of methods: on all fours like a salivating dog; bent over the back of sofas and across dining room tables; leaning against kitchen benches; and even with the top half of her naked body sprawled over the hood of a shiny Ford in a deserted beach-side car-park. Ruby Sanderson loved taking it in the arse. It was her thing.

“Okay, let’s get started on this survey, Matt,” Ruby smiled at Matt warmly. “Are you ready for a lot of questions about public transport?”

“Yep, go for it,” Matt replied. “Hit me…with your questions, that is.”

For the next ten minutes, Ruby asked Matt questions about bus frequency, reliability, need, and on-board comfort levels, and the young man answered seriously and thoughtfully, but also with a lot of good natured humour.

All the way through the survey, Ruby noticed Matt checking her out. The younger man looked sneakily down at her big breasts, and drank in the sexy squishiness of her big butt as it pressed lewdly against the chair she was so uncomfortably sitting on.

With a sexy shiver, Ruby also caught the younger man touching himself a few times. With a sly smile, Matt lightly pushed and grabbed at his penis through the thin fabric of his sweatpants, making no secret of what he was doing.

Ruby checked Matt out too, fascinated not just by his muscular physique, but also by the thick, swirling, extremely manly hair that covered his chest and mid-section.

With his long hair billowing past his strong shoulders and settling on his bare chest, Matt almost looked like Tarzan or some sexy barbarian out of a fantasy movie. Ruby was experiencing true lust in the presence of this hot younger man.

With just a few more survey questions remaining, Matt slowly stood up and smiled. Ruby paused before asking her next question, and once again took in the sight of his gorgeous body.

“Ruby, would you mind if I took these sweatpants off?” Matt asked quietly. “I’m really hot and sweaty from my workout, and they’re a bit uncomfortable. Would that be okay?”

“Um, yeah, that’s fine,” Ruby said in stunned disbelief. “This is your house, Matt…whatever makes you comfortable.”

With that, Matt quickly slid his flimsy sweatpants down over his muscular thighs and calves, and then casually stepped out of them.

Matt ducked into a small room near the kitchen which Ruby assumed was the laundry, and then returned empty-handed, his discarded pants presumably dropped in a laundry basket.

“Ah, that’s better,” Matt smiled, and quickly tugged at his cock again. “Much better…”

Ruby delighted in the sight of Matt in just a tight, cheap-looking pair of horribly patterned fitted boxer briefs. For such a sexy guy, Matt’s inexpensive, worn-out, style-free underpants were undeniably a major disappointment.

His legs, however, were appealingly taut, tanned and toned, while his gorgeously shaped butt looked to be rock hard beneath the thin, tattered fabric of his underwear.

The 30-year-old woman’s eyes really settled, however, on the huge bulge in the front of Matt’s underwear. The handsome younger man’s penis appeared to be almost freakish in size, and Ruby had trouble looking away.

Matt smiled naughtily at Ruby, and thoughtfully answered the rest of her survey questions while clad just in his underpants.

The older woman noticed him constantly flexing his muscles and spreading his legs to give her an even better look at his impressive bulge. Matt was really playing it up for her.

“Well, that’s it,” Ruby said after her final question. “Thanks for your time, Matt, I really appreciate it.”

“That’s okay,” Matt smiled. “I’m happy to help.”

“Great answers,” Ruby said and looked Matt up and down, not even trying to hide it this time. “Thanks for being so thoughtful.”

“My pleasure,” Matt smiled mischievously. “Ruby, I’m just going to take a shower. Would you mind if I took these pants off and dumped them in the laundry over there? Then I can see you out on my way to the bathroom down the hall…”

“Oh…um,” Ruby replied uncertainly, but with obvious excitement and amusement. “Aaah…”

“It might mean you’ll catch a glimpse of me in the nude,” Matt smiled. “Is that alright?”

“Okay,” Ruby giggled. “That’s fine with me.”

“Cool,” Matt smiled cheekily and then ducked back into the laundry.

When the younger man returned, Ruby gasped in shock. A near perfect male specimen, Matt was completely, shamelessly nude.

His penis hung down almost to his knees. It was big, thick, veiny, ropey and uncircumcised. Ruby had never seen anything like it before.

Matt’s thick, tangled patch of pubic hair, meanwhile, was wild and ungroomed, winding down to his inner thighs in dark, heavy twirls.

“Oh, Matt,” Ruby whispered. “That is most impressive…oh, Matt.”

“Yeah, it’s big, isn’t it?” Matt smiled and looked down at his penis. “Most women laugh when they see it. Some have screamed…one even cried.”

“It’s beautiful,” Ruby said quietly, instantly turned on by the sight of Matt’s nude body and exposed penis. “It’s amazing…can I touch it?”

“Yes, of course,” Matt replied. “Play with it as much as you like.”

Ruby moved toward Matt with a slight sense of uncertainty. She was still in shock not just about this handsome 21-year-old’s casual nudity, but in her wholly salacious response to it.

No man had ever stripped so shamelessly and provocatively before her like this. Matt used his sexuality wantonly, almost like a gorgeous woman does, and Ruby was incredibly turned on. She could already feel herself starting to get wet.

With some hesitancy but more excitement, Ruby reached her slightly shaking right hand out toward Matt’s monstrously dangling penis.

“I can’t believe you just got naked in front of me like that,” Ruby smiled. “I guess most women see that thing and then just drop their panties for you?”

“I don’t know about that,” Matt said, with just a hint of apparent nervousness. “I really like being naked in front of women, especially when they’ve still got their clothes on. I don’t know why…it turns me on…I know it’s strange, but it just gets me really hot.”

As Matt spoke, Ruby looked down and saw his penis starting to swell and thicken. She gasped in surprise at its increased size.

“You weren’t worried that I’d be scared or shocked by seeing you naked?” Ruby asked. “That I’d scream?”

“You’ve been practically licking your lips looking at me,” Matt smiled. “You were staring at my cock the whole way through the survey. I didn’t think you’d mind me being naked. It was worth the risk.”

“Well, you were right,” Ruby smiled. “I’m sorry for staring at you. You’re very sexy, Matt.”

“Thanks, Ruby, so are you,” the younger man said.

Ruby then took hold of Matt’s partially erect penis gently. The older woman peeled back Matt’s foreskin slowly, revealing his dick’s big, purple, swollen head.

Matt closed his eyes and moaned with pleasure as Ruby slowly stroked his penis back and forth. The younger man got instantly, enormously hard.

Matt’s monstrous erection raged and pulsed in the shocked survey taker’s hand. She still couldn’t believe how big it was. She still couldn’t believe this was actually happening.

Ruby took a few more strokes and then stopped, disappointingly realising that she wouldn’t be able to drag this arousing experience out for as long as she would have liked. The 30-year-old sighed and then looked Matt right in the eye.

“Matt, I’ve logged in with Urban Data Analytics…I can’t be here for much longer,” Ruby said. “I’ll get in trouble. I’m only allotted a certain amount of time for each survey. We don’t have long…”

“Oh, really?” Matt said with obvious disappointment. “We can’t fuck or anything?”

“We’ve got enough time for one thing,” Ruby said. “There’s something I’d really like you to do for me…”

“You want me to go down on you?” the appealingly willing Matt asked quickly. “I’ll lick you out…I love doing that. I’ve been told I’m good at it.”

“No, Matt,” Ruby said with a salacious, suggestive smile. “No…I want you to fuck me in the butt.”

“Whoa,” Matt giggled immaturely. “Really? Anal? Um…ah…I’ve actually never done that before. Wow! If that’s what you want though, I’ll do it…I just don’t have any experience.”

“That’s okay,” Ruby smiled and gave Matt’s stiff dick another gentle tug. “I’ll talk you through it. I really want that thing in my arse. I want to feel you in there.”

“Okay, what should I do?” Matt asked.

“Well, first, let’s get you naked,” Ruby said with a serious look on her face. “Oh, wait a minute, you’re already naked! We can skip that part!”

Matt laughed, his stiff dick comically swinging as he clearly responded to Ruby’s efforts to break the tension that had built up since she boldly asked to be fucked in the butt.

“Sweetie, do you have some lubricant?” Ruby asked quietly. “I need you to really, really slick me up back there. We need more than just spit, you know?”

“Right, right…I’m pretty sure there’s some in Paolo and Cecile’s room,” Matt said helpfully. “They’re always fucking the shit out of each other. Fucking loud too…he probably jams her in the butt all the time.”

“Now, Matt…what about Paolo and Cecile?” Ruby asked. “They’re not going to walk into the kitchen and find you with your penis up my bottom, are they?”

“No, no,” Matt laughed. “They’ve gone up to The Central Coast for a few days. Nobody will be walking in on us, I promise.”

“Okay, good…Matt, you go and have a look for that lube, and I’ll take off my slacks and panties,” Ruby smiled. “Okay?”

“Um, can you undo your blouse too?” Matt asked. “So I can see your bra? You’re really hot, Ruby. I’d love a peek at you.”

“Yeah, sure,” Ruby said quickly. “Just get the lube, sweetie.”

“Okay, okay,” Matt said and then ducked off down the hall, his erect penis swaying ridiculously up and down, and from side to side as he moved.