Roxanne Queen of Anal by Dazman
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.