The Dirty and the Dirtiest Pt. 02

In 2017, I was visiting Melbourne for a conference and reconnected with an old flame that would take the mantle as the dirtiest woman I had ever met. However, on that same visit, I was to get lucky with my fiesty property manager.

The conference finally wrapped up at lunchtime on Friday; Tracy and I had scheduled to meet at my townhouse at 3 PM. The day was glorious, with full sun on my face as I exited the train. Walking towards the Racecourse Hotel, I decided to kill time in the beer garden and soak up some rays.

At the appointed time, I walked the short distance to my townhouse, and not having the entry code, I leaned against the wall and waited for Tracy. She presently arrived, and we hugged tightly.

Following the inspection, which was satisfactory, I asked Tracy what she was doing next.

"Go back to the office, I guess," She said, expectation brimming from her beautiful face, "Most of my colleagues have gone home already."

"Well, why don't you go home," I said, about to make my move, "Or come and have a drink with me."

"I really shouldn't mix business with pleasure, but...." Tracy smiled, with feigned resistance, and followed my lead as we strolled towards the Racecourse Hotel.

Minutes later, we sat opposite each other in the sun, drinks in hand, watching the traffic roar by and the trams make their ponderous way to and from St. Kilda Beach.

"Do you enjoy your job?" I asked, minutes after some small talk was exchanged.

"It's all right, but it's full-on," Tracy replied, "I manage over 100 properties."

"That's a lot," I admitted, "Glad you have the time and energy to look after my place."

"Aside from those last tenants, your place is a doddle."

"It was the first property I bought," I said, "And it means a lot to me."

"I can tell," Tracy smiled after taking a sip, "I see that you love that place."

We talked about a wide range of subjects over two rounds. Still, Tracy's body language had an underlying sense of mischievousness, as if there was an unspoken question that she desperately needed an answer to.

"I'm single," I said, after a pregnant pause where the two of us stared at the other with either side of Tracy's mouth slightly upturned, "And you?"

"Same," She smiled broadly, chest rising and falling, "So, what are two singles to do on a Friday evening."

"Dinner and take it from there?" I said, grabbing the menu that was on our table.

"Sounds wonderful," Grinned Tracy, who took the second menu.

We enjoyed our meal, and there was some spicy banter. However, the western sun was sinking lower toward the horizon.

"What will you do for the rest of the night?" Asked Tracy as she pushed the plate away from her, full from the large meal.

"No plans of any note," I replied, "Perhaps a few more drinks, maybe go to the cinema."

"What about an offer to enjoy some wine and a movie," Proffered Tracy, clearly nervous, "At my place."

"That's a most generous and welcome offer," I beamed, assuaging her anxiety.

Tracy was immediately relieved of rejection and pleased at my acceptance of her most generous proposal.

"Where did you park?" I asked as we got up to leave the Racecourse Hotel.

"At the Coles Carpark," She replied.

We entered Tracy's Subaru Outback in less than five minutes and cruised towards her Ashburton home. She lived in an ordinary apartment block on High Street within easy reach of trams traveling to the city.

Upon entering the second-story unit, I was struck by Tracy's house pride. The home was immaculate and tastefully decorated in a minimalist setting. The space smelled sweet of lavender, and the sun shone generously, illuminating all rooms with unlimited light, despite the light fading to the west.

Tracy asked me if I wanted to watch "Netflix" and chill. I had never heard of Netflix before, so rather than appear ignorant, I answered in the affirmative.

"What would you like to drink?" She asked, "I have Pinot Noir or Chardonnay."

"Both sound great," I replied, "Choose for me."

Tracy giggled and selected a bottle from the fridge. She popped the cork and brought two glasses to the couch. Placing the glasses on the coffee table, Tracy perfectly poured ice-cold wine, proffered me a drink, and toasted us a cheer.

We watched a movie that Tracy chose, which I had little to no interest in, only hoping my patience would be rewarded in the long run.

"What did you think?" Tracy asked after the mediocre movie ended.

"There were several plot holes," I replied evasively, which was not untruthful.

We entered into a friendly discussion about the movie, debating the plusses and negatives and concluding that it was mediocre at best.

There was an uncomfortable silence, with some unresolved sexual tension between us. I had learned long ago that it was best for the woman to resolve such an awkward moment.

"Hmm, the wine is empty," Tracy clumsily uttered, after faking the finishing of the bottle, "Shall I get the second bottle?"

"I think I have had enough," I confessed.

"If not more wine," stammered a very nervous Tracy, "Then what?"

"A kiss?"

A visible draining of tension drained from Tracy's countenance, but her cheeks crimsoned, and the room temperature rose several degrees.

We melted together, and our lips quickly found each. Time stood still as we kissed for an eternity. The longer our lips locked, the more Tracy and I became aroused. As expected, Tracy's stimulation caused her to explore my body, beginning with my knee before moving across my leg towards my crotch.

"Fuck," I hissed as Tracy squeezed my bulge.

She clumsily tried to undo my belt and seemed frustrated that my hands were not engaged in busy work across her body. Shortly, Tracy placed my hand on her breast and encouraged me to massage.

"Let's go to bed," Tracy breathed.

We stood from the couch, and Tracy led me to her tidy bedroom. She pushed me onto the mattress and wrestled my jeans from my body. Once I was naked from the waist down, Tracy expertly grabbed my quivering shaft and jerked it several times before I encouraged her to swallow me.

"You're leaking," Tracy joked.

"That's your fault!"

"You think I'm sexy?" Asked Tracy rhetorically, breathing soft breaths against the purple head of my hardened cock.

Without waiting for a response, Tracy opened her mouth and swallowed me. She squealed in delight as my body spasmed in electrified pleasure.

"Fuck, yes!"

"Mmm."

After several minutes of head, Tracy begged me to go down on her. It was not a necessary request because I was seeking an opportunity to do just that. The aroma emanating from Tracy's pussy was unmistakable in the cloying atmosphere of her bedroom.

Tracy tasted fantastic; one of the best women that I have eaten. She had superb flavour, and Tracy came quickly and easily before begging me to fuck her.

Vaginally, we fucked in numerous positions, beginning with cowboy and ending in sidesaddle.

"Fuck," She thundered, "I'm coming again!"

With that encouragement, I slammed into her as hard as possible until her body shuddered with uncommon violence.

Tracy collapsed onto the sweat-ladened sheets, breathing with some difficulty. Her skin had a flushed and pink complexion. Neither spoke for several minutes, and I wondered what the following action might entail.

"You want to fuck my arse?" Tracy asked after recovering from her orgasm, chest heaving mightily.

"You're into anal?" I asked, hardly daring to believe my luck.

"Anal sex is cool!" She replied, kneading her breasts.

"It certainly is," I said, trying not to sound too excited at the prospect of playing with my property manager's sumptuous behind.

"I take it that's a yes?" She asked with a smile.

As soon as I nodded, Tracy reached into the table and grabbed a battle-hardened bottle of Durex lubricant. Popping the lid, she squeezed a generous dollop of personal oil into the palm of her hand, rubbed it into both palms, and used one hand to grease up my pulsating pole.

Once satisfied, Tracy quickly got on her hands and knees, reached around, and smeared excess lubricant across her dark, wrinkly anus.

"Stick a finger inside," I asked, loving the show.

Tracy giggled and complied. Her index finger disappeared inside, tentatively and first, but with growing confidence with my verbal encouragement.

"It's so sensitive," Hissed Tracy after taking a sharp intake of breath, "My behind, that is."

I reached in and spat a generous amount of spit onto Tracy's twitching O-ring between digital insertions.

"Looks so fucking good," I drooled while gently stroking my greasy cock.

"It's so narrow back there," Giggled Tracy as she prepared her hole for my cock, "And there are so many nerve endings that there are enough for ten vaginal and clitoral orgasms."

"So, you're going to come harder than before?"

"Depends how you work me," Tracy teased, "But I'm confident that I will."

After another thirty seconds of fingering her most intimate hole, Tracy told me she was ready. I moved into position, but before satisfying our desires, I grabbed her fingers and jammed her slimy fingers down my throat. The funkiness of her backdoor overwhelmed the sweetness of the lubrication.

"Tastes amazing!"

"You're a dirty little man," Giggled Tracy, eyes wide with lust.

"Are you ready?"

"Fuck my peach!"

I positioned my sheathed cock head at Tracy's greased-up pucker and pushed. Surprisingly, the digital preparation and generous lubrication coating eased my shaft inside her backdoor.

"Correction," Tracy murmured, "You're not 'little'!"

"You okay?" I asked, a little concerned as I continued invading my way inside.

"More than okay," She moaned, "I feel like a goddess."

I gave Tracy several moments to adjust to the intrusion, and she began bucking her hips against me, impatient with my caution.

Grabbing both hips firmly, I thrust Tracy's dirt box gently at first but with increasing firmness as she became increasingly vocal, her head firmly planted in a pillow, arms prostrate.

Tracy's anus was indeed "narrow," but it also emanated a heat like a blacksmith's furnace. With continuing thrusting, I felt her O-ring loosen.

"I bet you thought I was a 'good girl,'" Groaned Tracy, egging me on.

"I didn't think you were this 'good'!"

"I knew as soon as I met you that you'd not decline my bubble butt."

"Feels so good," I moaned, eyes shut tightly with my head back.

Tracy bucked and thrashed several times as her anus bowled one orgasm after another down her brown pitch, hitting the middle stump every time.

Given my good fortune and Tracy's skill, ability, and unrestrained lust, I knew my balls had little fight left in them. I wanted to see how Tracy gaped, but pulling out of her sumptuous buttocks was impossible.

"I'm going to come soon," I hissed, wondering what sort of finish I could expect.

"Come inside me," She squealed.

Disappointed that Tracy did not demand I explode on her face, breasts, or in her mouth, I nevertheless cupped her breasts and tweaked her dark brown nipples. The moment they began growing between my fingers was enough to tip me over the edge.

I grabbed Tracy's hips and slammed balls deep inside her delicate rose. My balls erupted, and I lost my grip on reality as my nerves exploded in a chain reaction of seismic pleasure.

"Fuck!" Yelled Tracy through gritted teeth, her body taut, her head thrown back, and her eyes bulging, "That's so fucking deep!"

She tried to get away from my grip, clearly uncomfortable, or possibly in some discomfort, at how deep I forced my pulsating prick up her anus at the moment of orgasm.

As my ten seconds of pleasure subsided, Tracy relaxed and began laughing. Sweat was cascading from my brow, and when I opened my eyes, a film of work covered Tracy's tanned skin.

Suddenly, new sensations assaulted my brain. Tracy was actively exercising her rosebud, which strangled my rapidly deflating cock. She had such control over her rectum muscle that Tracy quickly eased me out, and I collapsed on the bed.

"Let me see," Puffed Tracy, rising on her haunches, "Let me see!"

"See what?

"How much you came, of course."

She laid on her back with her hands, spreading her ass cheeks. In the dim light, I could see Tracy exercising her anal muscle, and seconds later, a funky string of white fluid erupted from her arsehole and pooled on the sheet.

"Oh, yeah!" She moaned as my jism fell out from her arse.

What Tracy did next defied belief. She launched onto her knees, located the wet patch, and knelt to scoop up the funky cocktail without hesitation.

Playing with my vicious man seed, Tracy let excess come spill over the edges of her tongue, where it landed on her brown nipples. Tracy tipped her head back slightly, and my sperm rolled down her tongue into the back of her throat. I closed her mouth and saw her throat jerk as she swallowed the contents.

"Mm, yummy!"

"I would have happily come inside your mouth," I said, my spent cock twitching at the visuals.

"Then I would have missed out on the biggest orgasm of all," Was Tracy's reply.

"How's that?"

"When a guy comes inside my butt, it's the deepest thrust of all," Tracy said, massaging several droplets of sperm across her sensitive nipples, "That second of vulnerability, the submission, and the pain of that last thrust launches me into the stratosphere!"

"Seems like we both had amazing orgasms!"

"Look," Tracy exclaimed jubilantly, pointing to the doona cover, "You made me leak."

Sure enough, there was a small, dark patch on the fabric.

"Does that happen often?" I asked after examining the dampness.

"Not as often as I'd like," Tracy smiled, lying back on the bed, nipples pointing toward the ceiling, "Those orgasms are super strong."

Later that night, as we rested from the night's exertions, I asked Tracy what she liked about anal sex.

"It's a separate thrill and completely different physical sensations," She replied.

When pressed further, Tracy confirmed that the feeling of defenselessness and submission to how a man might perform back there was incredibly erotic.

"It's a buzz for the 'bad girl,'" She continued, "Doing something that many consider taboo."

"It is becoming more mainstream," I observed, noting the growing abundance of anal porn.

"Anal sex not only opens up truly new horizons of pleasure," Tracy giggled, "But also makes relationships much closer and more trusting."

"You always let guys fuck your arse on a first date?"

"No, but I wanted you to look at it."

We eventually drifted off to sleep. The next day, Tracy's alarm buzzed at the ungodly hour of 7 AM.

"I've got to work until 12," She breathed into my ear, following an anal-heavy sex session, "Can we meet up later?"

"I'd like to, but I've got plans to meet with friends," I replied to a crestfallen Tracy, "How about tomorrow afternoon?"

"Sounds great," Smiled Tracy leaping from the bed, "You want to shower after me?"

"Nah," I said, picking up clothes from the bedroom floor, "I'll bathe at the hotel."

About half an hour later, Tracy drove to her real estate office, and I walked a short distance to the city tram stop.

To my ultimate shame, the intensely erotic and personal encounter with Tracy was soon forgotten by the anticipation of a round two with the filthiest slut of all, Amanda.