The Cougar and the Milf Pt. 02

The Cougar and the MILF: Part 2

Oreillan the cougar, a real anal aficionado, planned her next surprise for me -- because she was full of them. I was introduced to her best friend.

Fast forward a month or two, from the events described in the first chapter, and summer was on the cusp. Oreillan and I were socialising together with friends on both sides. One of her long-time friends was a well-built MILF with long, flowing dark hair by the name of Denise, or Dee for short. She shared similar physical characteristics to Oreillan: both girls were stacked up top although Dee tended to obscure her puppies; both had hour-glass figures; neither were skinny-minis but nor were they chubby instead they had meat on their bones, and both girls were divorced. Dee had kids, though while Oreillan did not.

There was a lot of affection, kisses and hugs and touching, between them, whenever they met, and I suspected that there was some past or current, sexual connection. This affection was a product of their long friendship. They met at High School and carried it forward ever since.

For the time Oreillan and I started hanging out, she gave off no sign that she might swing with the same sex. There was none of this affection with her other female, or male, friends that I noticed.

For the 2007 Melbourne Cup, Oreillan and Co. had booked a table at the Mount Hawthorn Tavern to 'watch the race that stops a nation'. Given that Perth is three hours behind Melbourne, the actual race took place at noon local time. For us, Western Australians that means drinking starts well before midday and we are usually out of the game not long afterwards. Luckily, booking a table meant we had food to line our stomachs.

Melbourne Cup was also an opportunity to get dressed up in one's finest, and boy, did Oreillan go to town. The night before the race, I stayed over at her house and brought a fine suit with me. On the morning of the race, we began the day without sex but with a champagne breakfast. Oreillan had bought six bottles of actual French champagne!

By 10 am, I was already buzzing as the taxi pulled up outside Oreillan's house. The lady of the hour, propped up by a pair of savage stilettoes with thinnest of heels, appeared. She looked stunning! Dressed in a delicate, canary yellow dress with one shoulder strap that so finely contoured her MILF body. Her hair was done up, and she wore a wide-brimmed jazz-style straw hat with a matching canary yellow bow. Oreillan smelled divine with a generous dose of perfume.

The journey to the tavern was short and sweet, and already the crowd was growing. Our table afforded us a view of the big screen, and we took our seats. Our entire party had made the effort in the fashion stakes, but none held a candle to Oreillan.

However, Dee came close. Frocked out in a pink, polka dot dress that accentuated every imperfect curve, Dee's MILF body was on full display with her full and chunky tits on display for the first time since I met her. I always suspected their size was impressive, but today I had my expectations subverted. All dolled up, Dee looked sensational. Mind you; every woman did that day.

The day was an absolute cracker all round. I did not win on any horses, but that is not what the day is all about. During the afternoon, I kept catching glimpses of Oreillan and Dee in conversation, exchanged furtive glances and checking me out. In my alcoholic fog, my brain kept telling me that Dee was sizing me up. There was something more to their friendship? Today would I find out?

Thankfully, the afternoon fizzled out around 3 pm. We all said our goodbyes, as, one-by-one, our taxis arrived. Back at Oreillan's, we took the opportunity to change into our standard 'civvies' while drinking champers and nibbling finger food.

Oreillan lived in a generously proportioned townhouse with a view of Perth CBD. Her upstairs deck was privately screened, and she had a queen-sized outdoor bed stationed there. Many a night, we sat there enjoying different whiskeys, chatting, and fucking (when it was warm enough, and we had enough mosquito repellent).

On this afternoon, we sat there gazing at the city, taking sips of champagne, and eating from a grazing plate. Oreillan seemed distracted, continually looking at her watch.

"What's wrong?"

"Nothing, honey," Beamed Oreillan, "Nothing."

Sometime between 4.30 and 5 pm, Oreillan's front door buzzer went off. I wondered who that could be? Sure enough, it was Dee, in her 'civvies,' carrying more food and wine, and she seemed tipsy, very tipsy.

"Hi Jason," She giggled as Oreillan led her upstairs, hand in hand.

"Hi Dee," I replied and took the proffered bags to the kitchen and unloaded them. Great, more champagne, that will lubricate the night. It was not a stretch to believe that an impending FMF threesome was in the offing.

I refilled everyone's glass, and the three of us took generous sips. Around that time, the sun was beginning to pass overhead bathing Oreillan's impressive deck in warmth and light.

"Let's go and get changed," Giggled Dee, grabbing something from her bag and walking to the bathroom with Oreillan in tow.

The Cougar and the MILF were bunkered in there for what seemed like an eternity. Curious, I sidled up to the door to listen in on their conversation, but they were speaking in hushed tones, punctuated every few seconds by guffaws of laughter. I heard running water often, but whether it came from the bath, shower, or vanity basis, I could not tell. Then there was another sound that I could not make out with any clarity. In all honesty, the sound resembled a fart which was then followed by eruptions of laughter that confirmed my suspicion. What were they doing in the bathroom?

Eventually, Oreillan and Dee came out dressed in their bikinis, sporting impressive racks and walking towards the kitchen like supermodels, shaking their fleshy booties. From the aroma they were giving off, both had rubbed in coconut sunscreen.

With refreshed glasses and some racy banter, the three of us retired to the sun lounger with the two girls on each side and me in the middle at the opposite end, soaking up everything the sun had to offer. No-one spoke much, but we all enjoyed the heat on our bodies and the cold drinks in our hands.

Eventually, the alcohol and the sun's brilliance made us all tired, and I dozed off. Before doing so, however, I looked at the two girls; I thought I caught Dee eyeing me up, but that might have been a reflection or a hopeful invention on my part.

I awoke slowly from my slumber as the sun passed overhead, bathing our toasted bodies in lengthening shadows as day gave way to a balmy evening. I grabbed the warming beer that I nestled between my legs before my impromptu nap and took a swig.

Yuck! I ought to grab a chilled one from the fridge, but I was sandwiched between two exquisitely sexy and well-built older ladies napping. So, not wanting to disturb the serenity, I sipped my warm beer, wincing with every swallow.

But then I discerned signs of life.

At first, Oreillan's feet began lightly twitching against the side of my stomach. There was no facial expression, and nor could I see her eyes behind her sunglasses, but she was awake, and in the mood to play.

I placed a hand on her silky, smooth leg and gently stroked her skin.

Still no reaction.

But I did not have long to wait.

Dee flashed me a smile and had been watching my interaction with Oreillan with interest.

Then Dee mimicked her friend, and so I had both girls rubbing their feet against me.

Stripped down her basics, Dee's physique was mightily impressive. The thought of these two going at it, or going on me, resulting in a stir within my shorts.

Given the implied consent, I began stroking Dee's legs coordinated with Oreillan's.

The two of them had concocted some sort of plan for this afternoon's post-race activity, so it was only a matter for me to show some patience and let the action develop organically. Luckily, the alcohol imbibed earlier led naturally to some degree of sexual forbearance.

"You want to get nasty?" Asked Oreillan, eventually after both girls had received prolonged foot massages.

"You think he's ready for it?" Replied Dee.

"If he doesn't spurt in his shorts then we're not doing our job!"

With a few giggles at my expense, the girls leaned in and kissed. Slowly at first but with more intensity as the passion rose.

"Move your legs," Snapped Oreillan when her lips broke from Dee's, "Sit on the edge of the bed."

"And no playing," Chimed in Dee.

I shuffled down to my allotted position, which allowed Oreillan and Dee to embrace and resume kissing passionately.

I rose to new heights of stiffness, watching these sexy older girls make out.

As they kissed, it was clear their passion was real, deep and had a history. That these girls were lovers or 'friends with benefits' or 'fuck buddies', or however they identified, their relationship went back a long time. For when they broke their kisses, they looked longingly and lovingly into each other's eyes. I felt blessed that Oreillan deemed me worthy enough to be present.

That, or she was pissed out of her mind and was not in control of her mental faculties.

Ditto with Dee.

In any case, who cared?

Not me.

After another round of sensuous kissing and stroking, Dee broke off and placed a hand on one of Oreillan's meaty tits. She said something I did not catch before Dee replied that she loved sucking on 'those' giving the breast in her grip a squeeze.

Dee kissed and tongued Oreillan's sensitive boob, which elicited the usual reaction when that happened. They kissed some more, exchanged some other words, but all I caught was the three of us were going to have so much fun.

Both girls shot me slutty smiles before kissing some more.

Dee reached around and undid the string of her bikini top while Oreillan grabbed hold of a boob. Unlike Oreillan's boobs that had little if any sag, Dee's were larger and showed the effect of rearing children but regardless they looked terrific; topped with dark brown nipples that were severely erect.

"Mm, gorgeous tits," Breathed Oreillan as she took that nipple in her mouth.

The passion was rising between these two, and I began rubbing my cock through my shorts.

Oreillan was sharing her of Dee's rack equally, while her friend moaned quietly and spread her legs. There was no sign of any wetness yet against her bikini bottoms, but I imagined the signs would appear shortly.

As her breasts were being gently nuzzled on, Dee deftly removed Oreillan's top, discarding over the side of the bed with a giggle.

"Look at that fucking arse," Said Oreillan, giving Dee's peach a playful slap.

Dee immediately reached over and twerked one of Oreillan's globes.

"Remember how we used to play with these as roommates?" Asked Dee before kissing Oreillan.

"I know!"

They were kissing harder and more urgently now, caressing each other's tanned skin, tongues dancing and moans increasing in pitch and tempo.

Oreillan broke the kiss and ran her tongue up Dee's thigh before flicking a nipple.

"Oh, that's giving me goosebumps," Exclaimed Dee.

Oreillan rose grabbed an arse cheek, pulled it apart before slapping several times to much snickering. Then she began biting and licking the flesh.

"Mm, you taste so good," Referring to the coconut sun cream they applied to each other in the bathroom earlier.

Using her teeth, Oreillan tugged at the string of Dee's bikini attempting to pull it off, but both girls used their hands to completely remove it, again tossing it over the bed's edge.

They kissed some more and exchanged some dialogue I was not privy to before Dee rolled onto her back and opened her legs. Oreillan positioned herself between them and began kissing down her inner thigh.

While Oreillan's bikini-clad booty was directly in my face (and what a perfect sight it was), I caught several glimpses of what lay between Dee's legs. She looked shaven (later confirmed), and as she used fingers to lightly stimulate her clit, I could tell she was wet.

Without warning, Oreillan playfully slapped Dee's hand away from her pussy.

"Standoff!" Exclaimed Oreillan as her head descended to Dee's box.

"What?" Came laughter, "I can't work my own pussy?"

"That's my job."

"You're so controlling!" Replied Dee, "That hasn't changed."

Oreillan laughed and started working on Dee's cunt while cupping a breast in her hand.

"Oh, yeah!" Breathed Dee, as Oreillan's tongue danced across her pussy and clit, "Mm."

Several minutes of what looked and sounded like expert cunnilingus in which much saliva was applied, Oreillan made it clear that this afternoon's fun was not about pussies at all.

"You know what I really miss?" Asked Oreillan looking up towards Dee's flushed face.

"What?"

"Eating your arsehole!"

"Dirty slut," Replied Dee as she rolled over to assume the doggy position revealing a yin & yang tramp stamp on her lower back, "Drink up then honey."

Smiling, Dee thrust her thick booty towards the sun. Oreillan initially began by kissing Dee's back with such eroticism before making her way up to her friend's face.

"You know I love your pussy," Breathed Oreillan as she kissed Dee, "but..."

"But you like my arsehole more." Replied Dee with a smack of the lips before both girls giggled in sexual delight.

"I'm a whore!" Confessed Oreillan to no-one's surprise, "And never once have you complained when I bury my face between your cheeks."

And with that simple statement of truth, Oreillan spread Dee's butt cheeks and dove into her arsehole with practised accuracy.

Dee purred in delight, long and deep sighs of pleasure, her eyes closed and her ample chest heaving mightily.

Seconds later, a hand appeared underneath and began massaging Dee's clit while Oreillan's hands kept Dee's cheeks wide apart as her juicy tongue enthusiastically worked that stink hole.

"Oh, your arsehole nice and wet and kind of open too."

Dee laughed and continued pleasuring her clit.

"I remember the first time you took it in the arse."

More giggling from Dee as Oreillan used one of her painted fingers to massage saliva across that spasming hole.

"Total natural!" Beamed Dee, looking directly at me with a wink.

Pack of sluts, these two!

And their filthy dialogue was a huge turn-on.

"Oh, that's so good," Moaned Dee, "I love your tongue in my arsehole."

Oreillan was getting into the action with pleasure, spasming each time her tongue lapped at Dee's experienced pucker.

"Very natural," Agreed Oreillan as she playfully slapped a thick cheek before sucking on Dee's hole with her entire mouth.

"You're making me so excited to take Jason's big cock."

I know, right," Replied Oreillan, "His cock is amazing."

They were acting and talking as if I were not present, but I suspected that this was not their first threesome and they were putting on an unforgettable show.

Back to the intense lesbian anal rimming to Dee's intense pleasure.

"It's time for the toy," Announced the recipient after another minute of Oreillan's expert tongue work.

Both girls stood on their knees, erect, tits jiggling, while Dee reached under the pillow and pulled out a slender, pink and rubber butt plug.

"You're so naughty," Teased Oreillan, "Let me lick it."

Dee brought the toy to Oreillan's lips, and the two of them engaged in a three-way kiss, lubing the toy with saliva.

"Turn around," Dee said to Oreillan, "Give me that booty."

Initially, I thought the butt plug was destined for Dee's freshly tongued anus, but Dee had other ideas.

Oreillan dropped on her hands, thrusting her arse towards Dee who went ahead to relieve her of bikini bottoms.

"Let's get these off," She said, "You don't need them."

From my vantage point, I could easily see the dark wrinkle of Oreillan's shitter without any need to part her globes. Her anus looked ready for action.

"Yummy!" Remarked Dee and she prepared to insert the toy.

But before she did, and to my delight, Dee ran her tongue across the sensitive hole. Her long brown hair cascaded across Oreillan's right butt cheek and swaying gently in the breeze, and a meaty breast squashed against the other cheek.

"Ready?" Asked Dee, positioning the tip of the toy against the puckered orifice, her pussy lips tightly clench and dry.

"I'm ready," Replied Oreillan with baited anticipation.

Dee looked directly at me as she forced the tip of the toy through the resistance. She took a sharp intake of breath as Oreillan's arsehole surrendered and took the toy, quickly I might add.

"You did it!" Exclaimed Dee and slapped Oreillan's right cheek in satisfaction, who, in turn, squealed in delight.

"So pretty!" Exclaimed Dee with a big smile and jiggled Oreillan's meaty globes for a minute or two.

"Can't wait to take his cock." Mumbled Oreillan, whose face was firmly stuffed in the cushion.

Dee looked at me and said the same.

I could barely hold my sexual rage and longed for the signal to bugger their arseholes.

Looking directly at me, Dee pulled the toy completely out of Oreillan's hole and stuffed it in her mouth in the act of provocative sluttiness. Oreillan took a sharp intake of breath.

Dee began rimming her girlfriend.

"Oh, shit!" Gasped Oreillan, as her pucker reacted to Dee's tongue.

Dee was not as enthusiastic for rimming as Oreillan. Her tongue danced lightly on the O-ring while Oreillan, by contrast, sought to lick the surface, use hocked-up spitballs to aid lubrication and force her tongue inside aggressively.

For the next several minutes, Dee teased her friend by inserting, then removing the toy and letting her tongue flick across Oreillan's dark opening to murmurs of pleasure subdued by the cushion.

"How do you like my arse, Jason?"

"Sensational!" Was all I could say, my cock groaning under the visual and aural stimulation.

"You're going to love Dee's as well," Replied Oreillan, "She's as dirty and nasty as I am."

"I don't know whether I can handle Jason's big dick in my arse," Dee said, smiling, before reaching over to me, "But I'm willing to try."

Dee turned to me, evidently satisfied with the rim job, and undid the clasp of my shorts, easing them off me. My jap's eye was leaking pre-cum, and my nerves were taut from the "pre-match entertainment."

How long would I last?

As soon as Dee's lips gripped my quivering spear, I did not think it would be too long.

While staying power was not an issue for me, and I could recharge quickly between orgasms, this moment, with these two girls, was lightning in a bottle, and I swore to perform accordingly.

Oreillan resumed rimming Dee's rosebud as I received an expert and sloppy blow job from her sexy, proportioned friend. All three of us were moaning in delight.

Dee was a committed, enthusiastic, and talented cocksucker, using her lips and tongue to give me pleasure, slurping and drooling constantly.

"Oh, God!" I moaned, "Feels so good."

"You're going to enjoy her," Replied Oreillan from the deep cavity of Dee's arsehole.

I tentatively placed a hand on the back of Dee's head as it bobbed up and down on my glistening pole. Oreillan watched intently as her tongue worked its magic on her friend's rosebud.

Following several seconds of brutal, saliva-drenched throat fucking, Dee offered Oreillan my cock.

"Honey, do you want to share this dick with me?"

"Sure," Oreillan replaced the butt plug in Dee's back door before sidling over to me.

"You've got such a great cock, Jason," Beamed Dee wiping saliva from her face as Oreillan effortlessly took me down her well-worn throat.

"Hasn't he?" Replied Oreillan.

Now, the two of them shared my pole; throating, licking and sucking my cock and ball sack. Taking turns and sharing loving glances, their joint technique brought previously newfound heights of hardness.