The Art of Anal Pt. 01

The Art of Anal Part 1

After indulging in some depraved antics with the sexually complex Mark, I cooled my heels at my favourite pub, the Broken Hill Hotel in Victoria Park. I sat at the bar with a pint of Guinness and read a book when from the corner of my eye, I noticed with a young woman dressed in a black tunic with gold piping.

She was of middling height, solid with Marilyn Munro curves and jet black hair. Her cheekbones were high, and she sported ab angular jaw and nose. I placed her in her mid-twenties.

Two characteristics defined her nature. One was a massive set of tits, and the other was her high-powered spectacles. To describe the latter as jam-jarred glasses was cliched but she sure was short-sighted.

She elbowed her way to the bar and ordered a drink. Leaning into me, she asked me about the book. I offered it to her, and she flicked through the pages and lingered on the photos in the centre. Believing the subject matter to be of no interest, the British conquest of Canada in 1759, she took the time to read the captions as the barkeep made up the cocktail.

"Looks interesting," She said, handing the book back with a smile, "Is it any good?"

"I've read better," I replied, placing the book on the bar top.

"Is this an interest of yours?"

"I'm kind of an amateur history nerd," Which was an understatement. In between searching for the most depraved sex available, I spent the rest of my leisure time reading Old World history.

As we conversed, I saw a name on her left breast, Ella Bache. Ah, so she was studying at the beauty college across the road from the pub. Looking over her shoulder, I saw three of her fellow students drinking cocktails and gesticulating wildly.

"My name's Mandy," She offered.

"Jason, nice to meet you."

We awkwardly shook hands, and she flashed me a smile. Mandy was attractive, but for the super-strength glasses, but she seemed comfortable in her skin.

When the cocktail came, we clinked drinks and took a sip.

"That good, eh?" I asked when Mandy winced after swallowing.

She offered me the straw, but I politely declined.

"Would you like to catch up sometime?" Mandy asked after chatting benignly for a few minutes.

"Sure," I replied, smiling, "I'd like that."

We exchanged numbers before Mandy kissed me on the mouth and grabbed my crotch while our lips lingered. Such action today would constitute a sexual assault, but a decade ago, people were adventurous.

Then she rejoined her fellow students with her back to me.

About ten minutes later, Mandy's group had left the pub.

Further in the evening, I sent her a text saying 'Hi' and to let me know when she wanted to catch up but did not receive a reply.

The next week saw me engage in an uncomfortable threesome with Mark and Grace, followed immediately by an anal-heavy solo session with Grace at my place.

Pulling out of Grace's gaping arsehole, I whipped off the condom and was about to spray my load over Grace's face when my phone screen lit up and pinged several times.

"Oh, fuck!" I yelled as my cock pumped out watery jism in wide aimless arc.

"Oh yeah!" breathed Grace trying to catch as much of my sperm in her mouth.

She loved drinking down bodily fluids from the head of a penis, and I enjoyed distending her skinny stomach with piss and sperm.

After Grace departed, I took a shower and fixed myself a drink. Remembering the phone pinging, I grabbed it from the bedroom, sat down on the couch and fired up the X-Box.

Ah, two texts from Mandy.

The first one simply said 'Hi'.

The second one asked me what I was doing and when I was free.

I replied and suggested dinner at a local Italian restaurant, but no response to that suggestion came back.

****

The following Wednesday, I received Mandy's reply at lunchtime that dinner would be nice and could I do it tonight. Sure, easy. So, I made the necessary arrangements.

At 7 pm, I was seated at my booked table, sipping a glass of Shiraz.

Mandy sent a text announcing she was running about 15 minutes late. I rolled my eyes in cynical surrender. Hopefully, she was dolling herself up.

It was not to be. When she arrived, Mandy dressed in a simple combination of jeans and a top that vainly attempted to hide her massive chest. She wore no makeup and overdid it with the perfume. In some respects, Mandy's approach to casual dining was not unlike many Perth-dwelling females her age. They competed for the skimpiest and fashionable bikinis in the summer but rarely made much of an effort at dressing up in the evening. At least she was not attired in a football jersey as many women that live in Brisbane are want to do when hitting the town.

We ordered our meals and chatted. I noticed that Mandy was throwing back the wine with unbounded enthusiasm which was lucky because I brought two bottles with me.

Initially, it seemed to me that there was not much chemistry between us and the ten years plus age difference appeared not to help. However, throughout dinner and wine, Mandy opened up. We had several intersecting interests, such as gaming and reading. Her taste in literature was fantasy fiction, and she had in-depth knowledge and appreciation of Lord of the Rings and, of course, Harry Potter. I had little interest in fiction but appreciated Mandy's enjoyment of that genre.

"So, are you single?" Asked Mandy, blindsiding me with the change of subject.

Technically, I was single but had a few casual fuck buddies, and I was not averse to adding another.

"What about you?"

"Been single for a while now," Mandy replied, gulping Shiraz.

I refilled both glasses and noticed that her cheeks were flushed and assumed the alcohol was loosening her up.

"How long?"

"About a year," Was her overly loud response, "He was a fucking prick!"

"Shush," I cautioned, noting a diner from a close-by table shot us a black look.

For the midweek, this restaurant was making a brisk trade. We had a table by the window that looked out onto the Albany Highway which runs for an unbroken 600 kilometres and terminates at the south coast town of Albany. Reminding myself that I used to live there about thirteen years ago caused me to shudder.

"Sorry," Giggled Mandy looking around sheepishly.

My last relationship in which contained some elements of commitment was with an older lady which lasted about 18 months and ended amicably. Since that time, I chased sexual experiences with casual partners of both sexes, which satisfied me for the time being, but I did not disclose this information to Mandy.

"I miss getting fucked though," Mandy exclaimed in a hushed tone.

"You could get it anytime you want," I replied.

"Sure, but I kind of want a connection with someone before boning them."

Mandy was direct, brash and a little low brow.

Given her age and relative lack of life experience, I speculated that her intimate skill would not be all that mature, but that was pure speculation at that point in our date.

"Plus, I'm pretty shy and find it difficult to approach guys," Mandy continued.

"You approached me," I replied, reminding her about our encounter at the Broken Hill Hotel.

"I'd been drinking."

"Oh, gee. Thanks," I said with mock indignation.

"No, it's not like that," Mandy reassured me earnestly, "I only noticed you when I reached the bar. I saw your book, and you and I liked what I saw."

"So, if you hadn't had a few cocktails, you wouldn't have introduced yourself?"

"Probably not," She laughed gulping down more Shiraz.

"Lucky me," I smiled uncertainly and took a sip straight after Mandy, "I'm glad you did."

"Yeah, me too," She flashed me a genuine smile, "But I was terrified next morning."

"How come?" I asked, puzzled after swallowing some linguini.

"I'm so shy," And probably self-conscious given her vision disability and her massive chest, "But my friends encouraged me to answer."

"Are you happy you did?"

"I am, thank you."

We finished our meal, and I paid the bill before walking out to the street.

"You fancy a cocktail?" I asked.

"Nah," Mandy replied, "Another wine would be nice.

The restaurant was located between two pubs, and I gave her a choice, and, thankfully, she chose the Broken Hill Hotel, my favourite watering hole. It was also a location that was close to my home in Lathlain.

"Do you live around here?" I asked as we walked the short distance to the pub.

"Yes, in Hordern Street."

"Unit, house?"

"Renting a unit."

"Ah, okay," I said, "I'm in Saleham Street."

"Where's that?"

"Just across the railway line, maybe five minutes from the Broken Hill."

"That's convenient," Mandy said, edging closer to me, "Is that why you go to the Broken Hill?"

"Yes, but I think it's the best pub along the strip," I answered, "It's where the beautiful people go."

"Like you and me?" Laughed Mandy who took told of my hand.

"Of course,"

We walked inside the pub and ordered a bottle of wine.

"Inside or out?" I asked.

"Outside."

The western sun had dipped below the horizon, and the pub's bottom courtyard was bathed in long shadows with landing light providing a cosy and intimate vibe. There was not a lot of custom in the yard, so there was little chance of being noticed.

"Cheers," I offered when I poured two glasses of deep red grape juice.

We clinked glasses, and Mandy took a huge gulp.

"Nervous?" I asked half-joking.

"Not anymore," Mandy replied and placed her glass on the table before reaching in and kissing me on the lips.

Dutch courage was purchased for the cost of an Italian meal and three bottles of wine which was nt a bad bargain in the grand scheme of the universe.

Our kiss lasted some time. Our lips synced smoothly, and tongues danced in each other's mouths teasing us. Kissing always gets me hard and tonight was no exception.

"That was nice," Mandy huffed when we disengaged.

It was. I expected Mandy to be a poorly trained poodle, but our kiss was about as perfect as they can be. Perhaps, she might not be that inexperienced, after all?

We kissed a lot more while devouring that bottle of wine, but precious little else which was fine because bar staff were always buzzing by our location.

"Can I walk you home?"

"I'd like that."

We walked together, embraced, and kissed like teenagers in dark places, the short distance to her unit. Mandy rented a small 1970s-style apartment in a small block of eight. The location was great, only minutes to the river foreshore.

Mandy opened the front door, turned around and kissed for the last time that evening. There was a look of internal struggle on her face, as she wanted me but needed to hold back. I was happy to wait because I found Mandy intriguing, and I really wanted to unbox her.

"Have the confidence to contact me tomorrow," I said as she stepped across the threshold.

I walked back to the pub for a nightcap before returning home and almost passing out in my spa.

****

Two days later, on Friday, I finished work and headed to the pub. True to her word, Mandy was in contact, almost always, over the past 48 hours. She was keen, and some of our chat bordered on the racy.

We arranged to catch up at the Broken Hill Hotel, but there was a catch. I had to watch her interact with her fellow students as they consume cocktails. Mandy kept shooting me alluring smiles while trying not to be noticed.

About 90 minutes in, the group of beauty students, including Mandy, left the pub. A minute later, Mandy came back in through the rear entrance and placed her hands on my eyes.

"Guess who?" She leaned in and kissed me.

"You look good," I said, admiring her black two-piece tunic uniform.

Dressed as she was, Mandy had a fantastic curvy figure that would look great in a corset. Sure, there was some baby fat, but she was not chubby or BBW. Her frame was what it was because it needed to support an above-average chest size.

I had relationships with two overly endowed anal-loving beauties in the nineties. Both said their backs hurt supporting such breast meat, and one of them had a breast reduction in her early thirties to relieve the pain. Basically, their bust cup sizes were at the lower end of the alphabet, but they loved receiving meat in the backdoor, so for a pervert like me, both women were prized assets.

"Cocktail or wine?" I asked, grabbing a fifty-dollar note from my wallet.

"Cocktail please."

With our drinks of choice purchased, we sat down and enjoyed each other's company.

"You want to have sex after this?"

If I had Guinness in my mouth at the time, I would have spat it out over the table, and probably escorted off the premises for my outrageous conduct.

"Ur, sure," I replied.

Mandy laughed and said that she had been thinking of me since Wednesday and became horny.

"Did you act on that?"

"You mean DIY?"

"Yep."

"That's all I've been doing for the last year," Mandy laughed, "It's kind of lost its appeal, but I still indulge religiously."

"You have toys?"

"Only two," She replied, looking directly at me with her magnified eyes.

"So, did you use them on Wednesday?"

"Wednesday and Thursday and this morning," Mandy confirmed, "Is that wrong?"

"It's nasty and sexy!"

Mandy, in her inebriated state that boosted her confidence, seemed pleased.

"Did you play with your cock?"

"I haven't actually," Which was true.

"Oh, full balls," Tittered Mandy, enjoying the banter.

"Fuller," I confirmed knowing that I had a cheeky wank at work the previous Wednesday morning before our dinner date.

"I love playing with myself," Mandy confessed.

"All your holes?"

Mandy shot me a quizzical glance before telling me that she only had two holes.

Anal virgin, then? Or anal prude?

"Most of the time, I film myself doing it."

"Oh, yes?" Now, I was really interested.

"I watch them, then do myself again," She laughed.

"I would love to watch them," I said, "Or better yet, watch a live-action show."

Mandy laughed and raised an eyebrow.

Minutes later, we were walking towards Mandy's unit. This time there was no hesitancy at the front door, and we ascended the stairs to her mid-level apartment.

The unit itself was dated in terms of features and fittings. There was a balcony that had a slight view of the river if your craned your head sufficiently, but the vista basically looked across the street toward another block of units.

Mandy had the basics of furniture, but the unit was sparse, which gave it a sense of space and openness. Cleanliness and neatness were not hallmarks of Mandy's residency, but the mess was subjective, and it did not bother me.

Before the lights were on, Mandy and I were furiously kissing, and her hands were all over my body. I kept up the facade of restraint because the boobs were the first things I wanted to maul. Tonight, was Mandy's gig, so I let her direct the action.

Mandy was rapidly unbuttoning my work shirt and began kissing my nipples. I let her do what she wanted, even though my nipples give me no pleasure at all. There was an urgency in Mandy's action, a need to vent pent-up sexual frustration and the lack of confidence to engage with the male species.

Her passion was intoxicating, and she quickly had my blood flowing with my nerves tingling all over. Mandy's breathing was shallow, and she whimpered continuously as she kissed my chest and abdomen.

"Let's go to the bedroom," Mandy suggested, just before I expected her to unbutton my trousers.

I was pushed onto the bed in the darkness. Mandy straddled me, and we kissed with furious passion. She ground her volcanic mound against my crotch, and I even received a hickey on the side of my neck, such was her overwhelming desire, and lack of maturity.

"I want to suck your cock," Mandy breathed when she released my lips from hers.

"Go right ahead," I answered, happy to be on the receiving end of Mandy's newfound sexual exuberance.

Everyone appreciates that sex under the influence of alcohol, and some drugs, dulls the pleasure, somewhat. Still, it usually has a hand in breaking the ice, giving men and women the confidence to engage with each other. I suspected that Mandy had more drink in her system than me, and this released her inner animal. If we have further rounds in the future, I wanted an encounter without mind-inducing substances.

In the meantime, Mandy had deftly removed my trousers, boxer shorts, shoes, and socks. Now I was naked, and she had me at her mercy.

As expected, Mandy's technique was clumsy but not unpleasant, and her enthusiasm was unrivalled. She took my raging cock in her mouth and bobbed her head up and down. Unlike other, more experienced, partners, Mandy failed to use her throat to coat my pole with saliva.

Mandy also went nowhere near my balls or arsehole.

Never mind, these are skills to be taught in the future. As will the art of anal sex with the first lesson happening tonight.

Minutes later, Mandy announced her need to be fucked. She stood up and began unbuttoning her tunic. The room was dark, the only ambient light came from the street, and I suspected that she retained a certain lack of confidence in her body shape.

Her silhouetted figure against the streetlight looked incredible as she did the unboxing that I desperately wanted to do. She removed her black trousers and straddled me again. I felt a pair of lacy knickers and matching bra press against me as Mandy pressed her lips to mine.

I rolled her over. My hard cock pressed against her fabric-enclosed mound and her massive chest rocked violently inside the bra.

"Let's get these off," I said.

I pulled her white lacy knickers down her thighs which she propped herself us to remove the bra. While shrouded in darkness, Mandy's breasts were magnificent, firm, perky and topped with large areolas.

Her pussy was hairy but not offensively so, and it emanated a heat and aroma that was intoxicating. Without asking, I went down on Mandy and ate her juicy lady parts. Employing my usual technique of circling clit and diving deep inside her pinkness, I brought Mandy off in a couple of minutes. She had an odd taste, quite bitter like stale piss.

"Oh, wow!" Heaved Mandy, "No one's ever done that before."

"What?" I asked, "Eaten you out?"

"Made me come."

"Perhaps you haven't had a real man in your life?"

"Maybe," Mandy replied, "But that was great."

"Rollover," I ordered, wiping the slime from my face.

Mandy got on her hands and knees.

Spreading her arse cheeks apart, I furiously started rimming her young pucker while stroking her clit with my fingers.

"Whoa, whoa, whoa," Exclaimed Mandy uncertain about my motives, "What are you doing?"

"Don't you know?" I said, coming up for air.

"You're...licking...my butt?

"It's great, isn't it?"

"You like it?" She asked her voiced dripping in scepticism.

"I love it!" I confirmed before resuming tonguing Mandy's 25-year old pucker.

"Never knew it was a thing," Mandy said, confused.

"Indulge me and enjoy it."

Mandy buried her head back on the blankets and let me do my thing.

Rubbing her clit and stabbing her O-ring with my tongue soon brought the results I knew were coming (pardon the pun).

"What's happening?" I heard Mandy moan as my tongue plumbed greater depths of her forbidden zone.

I did not answer but doubled my effort. Sure enough, Mandy's body shook as it did before, but this time with more violence as a second orgasm in as many minutes struck her.

"What was that?" She breathed.

"An anal orgasm."

"What?"

"Coming from receiving pleasure from your backdoor," I explained.

"I always thought anal sex was taboo," Mandy replied, wiping her brow.

"Can be pleasurable when done right," I said.

"Huh," Answered the short-sighted, boob merchant, "A conversation for another day."