Roxanne Queen of Anal

After moving from Melbourne to Sydney in the latter half of 2014, I reestablished my online dating presence. One Sunday evening, while hanging out in the chatroom, a woman sent me a private message, to my surprise. She also checked my profile, and while accepting her invitation, I looked at her summary, which contained scant personal detail.

As her name turned out, Roxanne began the conversation claiming to know me from somewhere based on my face. Unlike her profile, mine contained numerous photos of me in various locations and indulging in various outdoor activities. This album was curated from multiple sites across Australia and over a long time. So I naturally wondered if Roxanne was a skeleton from my past.

As we started chatting, it became less likely that we knew each other previously, and when she sent through a photo, I was confident we had never met before.

"Hm, weird," She tapped, "You look so familiar, and your profile really stands out."

Unlike Roxanne's, which was like 90 per cent of the female profiles on internet dating sites. The prevailing attitude is that they don't need to put the effort to describe themselves or their ideal partners in any significant detail to get the men to make contact.

We quickly migrated from the online chatroom to WhatsApp during the evening and learned more about each other. We messaged each other constantly each day after that, and by the time Friday rolled around, I asked her out for a drink after work. Roxanne accepted.

We met at a cocktail bar in Surry Hills, just outside the CBD and close to the train station because we lived in the suburbs on the same line, a couple of stops from each other.

I arrived fashionably early, and the cocktail bar had a respectable clientele even though most offices had not yet quit for the weekend. I secured two stools at the bar, ordered a drink and patiently waited.

Roxanne joined me maybe twenty minutes later, pecked me on the cheek and sat on the stool next to mine. After the usual pleasantries, I ordered her a drink, and we settled down to eye each other off.

Despite being five years older than me, Roxanne carried her age well. She was as tall as me, slim, busty, with long dirty blonde hair worn straight and loose. Roxanne oozed professionalism and confidence, dressed in body-hugging office attire and carrying an enormous designer handbag. What struck me most was her face. Roxanne had manicured eyebrows and pronounced eyelashes. Her eyelids were painted with a liberal amount of mascara, and her eyes were a piercing malachite green. Her nose was thin and straight, and her pouty lips, when smiling, stretched almost the entire length of her face.

At first, the conversation was nervous, even mundane, but she opened up more as Roxanne became more comfortable. After another drink or two, I steered the discussion into more racy territory.

"I consider myself an adventurous girl," Roxanne giggled, "I'm into most things."

"What's the most out-there sexual adventure you've been on?"

"Gangbang with three guys a couple of times," Roxanne replied casually.

"DP, spit roast, airtight?"

"All of those," She laughed, "Especially DP."

"So, you like anal then?" I asked.

"Love anal," Roxanne said decisively, "Can't get enough of it."

"Can you tell me about your very first time?" I said with salacious anticipation, my cock stirring in my pants.

"Oh, yeah!" Said Roxanne, suddenly engulfed with arousal, "My very first time was in the back of a ute in the middle of a field."

"Classic!" I responded, "How was that?"

"Well," Smiled Roxanne, "It was pretty wild, like, we tried anal first because I wanted to keep my pussy. I was not really experienced with it, so he convinced me to try real intercourse, and that was fantastic."

"So, anal was your first ever sex act?"

"No," Laughed Roxanne, "Technically, anal came after some mutual oral sex beforehand."

"On that night?"

"On that night."

"Did you experience an orgasm?" I asked.

"Oh yes!"

"And I'm guessing he did?"

"All over my chest!"

Excellent choice! I may have followed suit because Roxanne appeared to possess a great rack featuring C-cup tits whose nipples began poking through the material of her blouse as our conversation heated up.

"So, you're an anal aficionado?"

"Oh, yeah!" Roxanne began, "As soon as I experienced lubrication, learnt how to lube up my arse, I enjoy anal sex."

"You must have a sensitive arse!" I concluded.

"Orgasm every time," She said proudly, "Especially for guys with small cocks. Instead of putting them in my pussy, it feels terrific when they are in my arse."

"What about guys with big cocks?"

"They feel good in both holes."

"Shit!" I said, slightly worried that Roxanne might be a size queen and I might not cut the mustard.

"I never turn a cock away, big or small," Laughed Roxanne at the slight look of worry on my face.

"Size doesn't matter?" I asked, raising a questioning eyebrow.

"They all give me pleasure," Roxanne replied, "In one way or another."

We exchanged furtive laughs while nursing our drinks.

"What about you?" Roxanne asked, "What wild shenanigans have you gotten up to?"

"Well," I began, wondering how candid I should be on our first date, "I've done a couple of threesomes; MMF and FMF."

I had participated in MMM bisexual and FMT threesomes but decided against mentioning those experiences.

"Nice," Said Roxanne, nodding her head in approval, "Which one was best?"

"They were both great in separate ways," I replied after thinking for a moment, "Tie for first place, really."

"Okay, when was the most recent?"

"Of the two," I responded, pretending to think, "It was the MFM, six or seven years ago."

"Was the lucky woman sandwiched between your meat?" Roxanne asked lewdly, her nipples groaning to break out of their cloth prisons.

"Indeed, she was," I confirmed, "That experience was a first for the three of us. We were work colleagues."

"Oh, that's a dangerous liaison."

"It worked for a while, and all of us had some great sexual experiences together but was never sustainable," I agreed.

"How many threesomes did you enjoy?"

"Just the one," I laughed, "Peter, the other guy, was married and felt guilty about fucking another woman afterwards."

Although, he had no trouble with his conscience when chasing gay and bisexual encounters. He only curbed his enthusiasm after his wife almost discovered his secret life.

"You weren't cheating with anyone at this time?" Asked Roxanne, twirling the straw in her glass.

"Jacinta and I were both single, and we hooked up together often," I said, "In the office, in public and at our houses."

"Those first two places would be risky?" Roxanne opined.

"Nah, they were after hours or late-night bouts of fun, away from prying eyes."

"Give me examples of a public place that you've fucked in?"

"Public toilets and parks."

"And you've never been caught?"

"Almost, onetime, my girlfriend and I were getting frisky in one of the stalls of the female toilets at the bus terminal in Perth," I laughed, "When some revellers burst in and almost rumbled us."

"How far into the deed were you?" Chuckled Roxanne, wide-eyed now.

"Halfway," I replied with a smile, "Let's just say our near discovery was a deflating experience."

"I bet it was! I've never done anything like that."

"Do you want to?" I asked, wanting to gauge her level of interest.

"I'd be too worried about getting caught," She chuckled.

"Fair enough," I said before finishing my drink.

Roxanne excused herself and forced her way to the bathroom. I wondered about the state of her panties after we discussed each other's sexual exploits. Looking around the bar, many more office workers had filed in, and the ambient noise had increased. There was no chance that anyone close by could hear our spicy conversation. Even the bar staff fliting by desperately seeking to fill eager drink orders could not catch a snippet of what passed between us.

When she returned to the bar, Roxanne squeezed onto the barstool with some difficulty given the jostling patronage yelling to be heard or waving to be noticed. I asked her if she fancied another drink, and she nodded in the affirmative. I placed $50 on my empty glass as a signal to the bar staff when they got around to me.

"That was a challenge," Roxanne said.

"What was?"

"The bathroom," She said playfully, "I almost slid off the seat."

"Ah," I responded, knowingly, "Bit wet, are you?"

"Flooding!"

"Well," I said smiling, "Our spicy chat got a rise out of me."

"Better get that under control before you need the bathroom," Laughed Roxanne, "You might miss the bowl!"

"That would be unfortunate," I agreed.

"I'm assuming that you're into anal sex?"

"Giving or receiving?" I half-joked.

"Oh," Roxanne's eyes widened at my unexpected reply, "Both."

"I love eating and fucking a beautiful female butt," I said, "I get off when a woman rims my hole."

"What about a woman finger you or uses toys?" Roxanne asked.

"Haven't experienced that in a few years, but I remember enjoying it," I answered honestly.

Roxanne's eyes sparkled at my revelation.

"I love pleasuring a man's bottom with my fingers and tongue," Roxanne shivered, "But not too many men are willing."

"Their loss," I said dismissively, "But what specifically do you like about anal sex?"

"Everything!" She answered immediately, "Every nerve in my body tingles and, when I orgasm, which is always, my brain goes off like a fireworks display."

"I've heard a lot of women speak in similar terms."

"Sounds like you've arse fucked a lot of women," Roxanne gently chided.

"Not everyone woman was into anal sex," I observed.

"Then they're missed out," Roxanne said derisively, "But, you're going to get it tonight."

Hers was one of the most direct invitations I have received ever, a testament to how horny she was.

"Your place or mine?"

We settled on Roxanne's as she lived alone despite being further away on the train. Before leaving, I grabbed my money just as I was about to be served and vacated the seats, which were taken up immediately.

Roxanne rented a modest two-bedroom unit in a small block off the main road that was tastefully furnished and tidy.

"I'm going to freshen up," She said, "There is wine in the fridge if you fancy any."

Both suggestions had merit, so I took the opportunity to wash my genitals as they were no doubt funky from a full day at the office. That done, I helped myself to the offered win and sat down on the couch.

After a time, I heard the bedroom door open and the bathroom door close. No doubt, Roxanne was preparing her body for what was likely to be a heavy anal session.

When she flitted into the lounge room, my jaw dropped to the floor. Roxanne had dressed in a white-bordered pink string bikini, frilly ankle socks, and black high-heeled shoes. Some thought had been put into tonight's activities.

"Wow," I stammered as Roxanne twirled around for my delight.

My cock was instantly hard.

Roxanne's body was amazing. Not muscular but toned from working out three times a week and a careful diet.

I was on her the moment she sat next to me, kissing furiously and running my hands over her incredible body.

"So, I'm going to fuck your arsehole tonight?" I asked when our lips broke.

Roxanne leaned back and spread her legs.

"Look," She said, pulling back her G-string and parting her swollen pink pussy lips, "My pussy is so wet.

With a dainty finger inserted for a second, she showed it to me with a thick fluid dripping from the end.

"That is not lube; it's all-natural," Roxanne observed before licking the finger clean, "And tasty too."

"Stand up and let me see your arse."

Roxanne stood up, stood in front of me and turned around. The G-string rode high up between her wobbly cheeks. She placed both hands on her cheeks and jiggled the flesh.

"That's a big arse," I marvelled.

"Round arse."

I reached up, placed my hand between those fleshy globes and lightly brushed a fingernail across Roxanne's pucker. She immediately shuddered and let out a moan.

"You okay?" I asked, pulling my hand away.

"Definitely okay," Said Roxanne, who cocked her head to me with a big smile, "You want to see my arsehole?"

"Yeah, let me see it."

Roxanne pulled down and discarded the G-string before bending over. She pulled her cheeks apart to reveal a slightly discoloured disc of skin and an almost triangular rosette.

"You can lick it if you want, play with it, do anything with it?" She said, "I love it all."

"I will but first, do you like to suck cock?"

"I love to suck dick," Roxanne replied as she made a blowjob motion with her hand and mouth.

"Will you suck mine?"

"Yeah," She teased with a lascivious grin, "Why not?"

"Oh, you're nice."

Roxanne knelt between my legs and helped me out of my clothes. My cock stood rigid like a tentpole and, without comment about it, grabbed the base and immediately and vigorously began throating my shaft, staring intensely into my eyes.

"Oh, yeah, that's so good," I groaned, enjoying her technique of synchronising her mouth and hand to jerk my cock hard.

Roxanne blew me to heaven for several minutes while I pawed her incredibly augmented tits, their nipples standing to full attention.

Without prompting, Roxanne took my cock from her mouth, spat on some fingers and began ticking my pucker as she resumed sucking on my pole.

"That feels good, baby!" I encouraged, "You can go further if you want."

I felt oddly relaxed from the alcohol and Roxanne's superbly slimy oral skills that I was ready to accept her digits in my sensitive hole. When she penetrated, Roxanne threw her head back and let out a long and satisfying hiss. Was that an orgasmic expression?

Placing a hand on her head, I forced Roxanne to take more meat down her throat. Her stimulating fingers appeared to make me harder than I already was.

"Fuck, that's amazing," I moaned as my bell end tickled her tonsils and her fingers danced across my prostate, "You're one sexy bitch!"

She continued this almost unbearable assault on my pleasure zones for several minutes before I begged her to stop because I was in danger of orgasming too soon. Roxanne spat my shaft out with a smack of the lips and a deep exhale.

"Let's get you bent over on this couch!"

With Roxanne prostrate, her bubble cheeks parted naturally, and I buried my face in that newly formed canyon and eagerly began lapping at her bung. Initially, she tasted soapy, indicating that she had taken the time to douche before activities commenced, enabling me to coin the title anal queen.

Before long, we were both moaning in pleasure while Roxanne shivered each time my tongue danced across her sensitive hole.

"Oh, that's so good," Roxanne repeated.

"That's one tasty fucking arsehole, babe!"

Occasionally, when taking an oral break from rimming her arsehole, I dipped fingers into Roxanne's lava-like pussy that was in full flood and rubbed her clit, but it was her O-ring that captured the bulk of my attention.

The two of us could not get enough of my tongue. Each time I spread Roxanne's cheeks to the extreme, the more expansive Roxanne's aperture became. Clearly, she was as relaxed as I was.

"Let me do it to you," She begged several minutes later.

I stood on the couch with my knees resting against the backrest cushions, arms resting on the headrest. Roxanne was on me within seconds, furiously rimming my shitter. The pleasure was unbelievable because she knew what she was doing.

"Jerk my cock at the same time," I implored, "Not too fast, though."

Roxanne was as good as her word, gently stroking me and poking her tongue between the edges of my hole. She spat several loads of saliva between my cheeks and delicately inserted two fingers into my bung.

"Fuck, that's tight," I hissed.

"You like it?" She asked.

"I love it."

Roxanne alternated between fingering and rimming my arse but kept a constant wanking motion on my shaft. Her actions were immensely pleasurable, and I could tell that she was getting off on it too. Both of us were purring contently.

"You're relaxing now," She said smoothly.

It was true, her fingers did not feel as uncomfortable as they initially did, and they were sliding in and out easily.

Next, I could feel Roxanne position a finger from each hand at each side of the O-ring and gently apply pressure. My hole reluctantly but inevitably opened further.

"Wow!" Exclaimed Roxanne with genuine surprise, "Fuck, look at that!"

"I can't," I gasped, struggling with the twin elements of pleasure and pain.

"You're fucking gaping," She marvelled, "I've never made a man gape before."

Next, she tried inserting four fingers in my arse, but even though I was jerking my cock to offset the torment, it was a stretch too far for me.

"That's the furthest I've been with any man!"

I collapsed on the couch with one leg resting on the headrest and the other spread on the floor.

"Suck my cock!"

Roxanne throated me with one hand on my shaft and the other stimulating her steaming box. She kept looking into my eyes all the time to gauge the pleasure I was deriving from her talented mouth.

"Oh my god, that's good!" I moaned continually.

Then, Roxanne motioned me to pull back my legs so that she could lick my sore hole, taint and rapidly tightening ball sack.

"Let me see those pretty eyes!"

Roxanne applied generous amounts of throat juice to my erogenous zone while I jerked my shaft before she took over. She aggressively blew my cock, hard and deep with eyes tightly shut before returning to my arsehole for the next moment in time.

"Yeah, tongue fuck that arsehole," I encouraged as Roxanne's tongue stabbed at the opening.

"Come and fuck me," She demanded, rising to her feet and helping me to mine.

Roxanne got on all fours on the couch again, pucker winking and guided my cock inside her volcanic but tight pussy.

As I worked her cunt, Roxanne would occasionally reach around and force two fingers into her arsehole, setting off a mini orgasm.

I stood up on the couch and straddled Roxanne, achieving the maximum penetration angle.

"Fuck, that's deep," She grunted.

After a few minutes of doggy-style pussy drilling, I withdrew the gleaming shaft and ordered Roxanne to clean it up.

"Please, just do it," She begged with a smile after licking up her slimy juice, "Put it in my arse."

Roxanne got down on the floor with her arse high up. I grabbed the bottle of lubrication from the side table, rubbing a small dollop on my shaft and in her winking arsehole. Straddling her wobbling cheeks, I positioned my helmet at the centre of her opening and pressed. Roxanne took my meat easily, and I quickly sank until I was balls deep inside her arsehole.

"Oh, yeah!" She sighed in a guttural voice.

As I began thrusting my engorged prick in and out of her backdoor, Roxanne let out long and deep groans of pleasure.

Despite being relaxed, Roxanne's bung was still plenty tight. I relentlessly barraged her with missives about how good it was to fuck her in the arse, to which she responded with, "I love it!" each time.

I started teasing her by threatening to withdraw my cock from her funky butthole, but Roxanne would wiggle her cheeks and beg me not to.

"Pull your cheeks apart," I demanded, "Hold your arsehole open."

With both hands pulling those globes apart, I pulled out for the gape shot. Sure enough, one was there, small and round about the size of the ten-cent coin. I would thrust my cock head in and withdraw it in quick succession, and each time there was a satisfying pop, and the O-ring flexed.

"Fuck, my cock feels good up your arsehole!"

"Can we change positions?" Roxanne asked after several more minutes of savage doggy-style sodomy.