The Cougar and the Milf Pt. 04

NOTE: This story explores themes of anal sex, enemas and golden showers. If these topics are not to your taste, then hit 'Back' on your browser and move along.

"That was fun," Oreillan said as we walked back inside the house, "I must get Dee involved."

Life came back to my cock at that suggestion and, as we shuffled to my bedroom, Oreillan's sphincter received some much-needed punishment before we both collapsed and passed out.

Over the next few weeks, including Christmas and New Year, Oreillan and I engaged in a lot of anal sex and golden showers.

"What have you, or when have you, planned our next threesome?" I asked Oreillan as we relaxed in the spa about a week after New Year's.

"We can tee something up for the long weekend, if you want?"

What not now?

"Sounds good," I replied, "Anything you want us to get up to?"

Oreillan reached around in the water and grabbed my prick and gently jerked my rapidly inflating shaft.

"Fun," She said simply, "Lots of orgasms."

Realising that such opportunities came along in a seldom manner, I wanted the second threesome to achieve some fantasies, and I began pondering what I wanted to get out of such an experience.

It was a pleasant surprise to receive a Skype call from my old lover, Thomas, one Saturday at home alone. I say 'old' because he settled into a monogamous relationship with a fellow student closer to his age. I was fine with his decision as I felt that together, Thomas and I had reached the limit of our sexual exploration. Thomas was gay where I was bisexual and tended strongly to women, so I was never going to satisfy his need for an exclusive relationship. We drifted apart but remained friends and chatted often but never physically met.

When we caught up online, the chat never became racy. Sometimes we reminisced about our adventures but that was as far as it went. Most of the time, we chatted about our mutual interest such as books, TV shows and movies.

"I ran into Bashir and Halima the other day," Thomas said, after the usual pleasantries had been exchanged.

"How are they doing?"

Bashir and Halima were a married couple from Somalia with whom Thomas and I enjoyed a one-off nasty anal-focused foursome some time ago.

"Yeah, good," Replied Thomas, "Bashir was picked up by the government science department and Halima is a nurse at Royal Perth Hospital."

"Nice one,"

"Yeah, they told me to pass on their regards."

That unique encounter together fulfilled a lot of fantasies that the four of us harboured including DP'ing Bashir who was bisexual like me but happily married.

"How's James?" I asked of Thomas' partner.

"He's okay," Said Thomas hesitantly, "Meeting up with him later."

I had no opinion about Thomas' partner. He was not my type by any means but the fact that he smoked was a huge turn off. As Thomas did not smoke either, I could not understand how he tolerated such a disgusting habit.

"Something wrong?" I asked, sensing all might not be well.

"It's just...He's just not as adventurous as I'd like," Sighed Thomas.

"In what way?"

"James just wants to be take it all the time," Thomas continued, "He doesn't want to give back."

"Oral, anal what?"

"Anal."

"He won't fuck you?" I asked with surprise.

"Says it doesn't turn him on."

How can giving anal, whether it be to a woman or a man, not be a turn-on?

In my recent foray in the world of bi-sexual encounters, I discovered that men divide themselves into to three categories: bottoms, who take anal; tops, who give anal; and switches, like me, who give and receive. While I occasionally switched with Thomas, I tended more towards a dominant top.

"So, you haven't had your arse fucked since hooking up with James?"

"Nope," Replied Thomas, "And I'm really craving it."

"Can't you pin him down, straddle him and ride him hard?"

"Believe me, I have tried," Said Thomas, laughing, "James doesn't want to fuck me."

"What about getting a dildo or a vibrator?"

"Suppose but it's a bit impersonal," Thomas replied, as if the thought had already been considered, "I want a proper cock to plough my dirt box."

This racy banter was making me hard and I wondered where Thomas was going. Was I about to be asked for a hook-up to satisfy his anal craving? Would he cheat on his partner to relieve some pent-up sexual tension? For that matter, would I agree? It had been nearly a year since I enjoyed some man-on-man action, and I was really having fun with women, even if they did not always give up their booties. The thought of getting some anal action did appeal.

"It's a shame that James isn't scratching your itch."

"If he did, I doubt it'd be anywhere near as good as you," Replied Thomas with a big grin.

"You have a nice fuckable anus."

"Nobody fucked it like you did," Thomas responded as he shuffled on his computer chair, "I loved it when you pinned me down with all your weight forcing your muscly prick deep inside me. God, I felt full."

Now, I was rock hard and stroking my cock beneath my shorts. I still was not convinced that I would accept an offer if Thomas made one, but I was certain that I would be wanking off as soon as the call ended.

"I enjoyed being balls deep inside you, gaping you, and using your arse pipe for my pleasure." I said, encouraging more banter.

"Sucking on your cock after it had been inside me was heaven," Said Thomas.

He had a hand below the table, and it was obvious that he was stroking his prick.

"Yeah, watching you lick off your own arse juice was a real sight."

"Oh, I miss doing that to you," Thomas replied with a hint of regret.

"You and I had a lot of fun together," I said.

"I loved those times when you put that kitchen funnel in my arse, pissed inside me then fucked it out."

"That was so fucking hot," I answered and gripped my cock harder.

"Shit, I really need to be fucked!"

There was a real sense of frustration in Thomas' voice and I wanted to help but I purposefully stopped short of propositioning him. If he wanted me, Thomas would have to ask.

"With this?" I was turned on by Thomas' reminiscences and knowing that he was playing with his cock, I decided to raise the stakes by standing up and dropping my shorts.

The reaction was instant. Thomas' mouth and his eyes bulged as he stared at my boner through the webcam.

"Fuck, yes!"

"Get your cock out!" I ordered.

Thomas completely discarded his clothes, and I saw that his cock was rock hard with precum glistening at the purple helmet. At that instant, I would have been straight over to his place to devour this young, gifted engineer, but I kept quiet.

"That's the gorgeous cock I need fucking me right now!"

"Show me where you want it," I said.

"In here," Thomas open his mouth and stuck out his tongue in front of the webcam.

My pumped pole jumped at the sight and the thought of his mouth administering one of his beautiful blow jobs.

"Then, when you're super hard, I want you here," He turned around, spread his arse cheeks and exposed his twitching pucker.

That action just made me want Thomas more. The tight and volcanic confines of his anal hole had the frequent ability to choke the life out of me and have me climaxing in no time at all.

"Stick two fingers inside your hole," I ordered.

Thomas, submissive when he wanted to be, complied.

"Now fuck your arse and work that pole," I said, enjoying the view.

"Fuck me Jason," Breathed Thomas, as his fingers work that criminally underused arse and his other hand wanked his cock.

"Just imagine me, behind you, hands gripping your hips as my veiny cock fucks your shitter."

Oh yes! Fuck it hard."

"My thick cock gaping you, opening you up!"

"Oh yes, make it hurt!"

For several minutes, I encouraged Thomas to greater heights of self-pleasure as he finger fucked his booty hole while jacking his cock.

I was getting close to an orgasm watching Thomas through the webcam, but I would wait until he came first.

"Take your fingers out and lick your arse off them," I ordered, "Think of my cock as you do so.

He did but Thomas did not show me cleaning his digits. When he stuck them back up his arse, I could clearly see the saliva on those fingers.

"Fuck yourself harder now and squirt your cream!"

He did so and the rapid finger fucking was a sight to behold.

"Go on Thomas, fuck yourself with my prick deep in your shit hole!"

"I'm nearly there, keep talking!"

Offering more words of encouragement, I could just see the furious wanking motion between his legs. Then, suddenly, his body started jerking as his orgasm crashed over him. Thomas continually moaned as his balls expelled rope after rope of sticky cum.

Slowly, Thomas pulled his fingers out of his twitching O-ring and he released the grip on his deflating penis.

All I could see was Thomas slumped over his computer chair, breathing heavily.

"Fucking hell, that was so strong!"

He seemed genuinely amazed at the strength of his orgasm.

Thomas turned around to face the camera and thanked me.

"That was the hardest orgasm I've had in a long time," He said with flushed cheeks.

"How do you normally come?" I asked.

"In James' mouth or arse," He replied, "But, as you know, I come harder with a cock up my arse."

"Yes, and when that happens, your twitching hole tips me over the edge."

"And then you spray the inside of my hole with your hot cream!"

"I enjoyed cream pies with you," I responded.

"You liked it when I played with that cream pie," Thomas said, acting all slutty in order to get me off, "Especially when I ate that cream pie!"

With that, he collected sperm that he shot onto his computer chair, brought the cum-smeared hand to the webcam, ate some of it and rubbed more over his face.

"Oh yeah, come on my face, Jason," He teased as I jerked my shaft, "Paint my face. Make me eat your seed."

I was so fucking close now. Thomas' play acting was next level in how it turned me on.

He returned to the chair and scooped up more jizm and sucked it from his fingers. The image was crystal clear and I saw the fluid on his tongue and watched as he swallowed it.

"Oh, fuck!" I screamed as my balls propelled arc after arc of semen all over my keyboard. In the blackness, my body erupted in pleasure bolts and I yanked my cock to climax.

Seconds later, I slumped back into the chair and the first image I saw when I opened my eyes was Thomas' beaming face.

"That looked so good!"

"Whoa," Was all I could manage.

I looked at the keyboard that had three parallel lines of viscous man cream that would take some cleaning.

"Look!" I brought the keyboard to the camera to show Thomas the mess I made.

"I would love to clean that up for you."

Really, I thought? Was that an offer?

"It'll have destroyed my keyboard by the time you get here," I replied with a smile.

"Too true," Said Thomas with a tinge of longing, "I better clean up because I have to meet James shortly."

"Now worries," I said, completely spent, "Thanks for calling. That was a lot of fun."

"Yeah, let's do it again soon. Next time in person. Ciao!"

Thomas killed the call and the camera feed, leaving me stunned. Did he want to rekindle our sexual connection? Time would tell.

However, the call with Thomas provided me with the means to do some nasty piss play with Oreillan.

The kitchen funnel.

When Australia Day rolled around, Oreillan engineered another threesome with Dee. This was the first since the Melbourne Cup, although the three of us had caught up many times between early November and late January the following year.

After being told of the threesome, I worked on some ideas and fantasies that, if executed as they played out in my mind, would top the first threesome. To that end, I purchased a cheap plastic kitchen funnel and an enema bottle from my local sex shop. I also left a bottle of milk warming up on the breakfast bar.

Just after 3 pm, the girls arrived at my place looking fabulous in summer dresses with plunging necklines and high cuts up the leg. Both brandished chiller bags containing multiple bottles of wine which were quickly deposited in the fridge.

Dee walked out on the patio and cast her gaze around my backyard.

"Jeez, you weren't kidding about the space," She said after taking a glass from Oreillan.

"Isn't it great!"

"You'll enjoy the spa," I said after grabbing a beer and joining the cougar and the MILF.

"Yes, Oreillan's told me about it."

"Care to try?"

"Yes please."

We collectively placed our drinks in the holders cut into the top edge of the spa and proceeded to remove our clothes. I slipped into the buddling water first and watched as the ladies climbed in. The sight of Dee's amazing MILF body had me instantly hard, and I noticed her nipples were standing to attention.

"Oh wow!" Said Dee as she settled into her seat, her face all animated at the sensation of the water against her tanned skin.

"It gets better," I grinned and reached the dial next to my beer.

Turning it activated the jets.

Dee let out a squeal from the unexpected sensation.

"That went right up my bum!"

Oreillan laughed as her friend jumped in surprise.

Won't be the last thing going up that sweet hole, I said to myself while wondering how I was going to enact my filthy plan.

"I bet the two of you have had some fun in here," Dee said, after taking a sip of wine.

"The odd bit," Replied Oreillan, shooting me an amused look.

We shared golden showers in the spa and I regularly bent her over the side and had my way with her pussy and arse. Not wanting to the attract the notice of my nosey neighbour, we had to muffle our orgasms.

"Be a darling and refill our glasses for us?" Oreillan asked after draining her wine.

I shuffled over to the steps and exited at the last moment in a vain attempt to conceal my boner. No such luck!

"Someone's excited," Teased Dee, to which Oreillan simply laughed.

Embarrassed slightly, I exited the spa, briefly toweled off before wrapping it around my waist.

Opening the fridge and grabbing the wine bottle, there would be enough to fill both glasses before it was empty.

With a replacement beer in hand, I rejoined the girls and topped up their glasses before placing the bottle and towel on the outdoor table.

As soon as my legs and straddled the spa's edge, Dee lunged and took my hard cock inside her mouth. Simultaneously, Oreillan used her hands to spread my arse cheeks and clumsily tried to get her tongue on my pucker.

The sensation was exactly what you imagine it would have been.

However, the position was all wrong.

Dropping my beer in the water, I stood erect and grabbed hold of the pergola beam for support. This semi-standing position gave the ladies much easier access to my cock and pucker.

I watched in fascination as Dee worked my shaft and cupped my balls, and reveled in the darts of pleasure coming from my arsehole.

"You sluts really know what you're doing," I moaned as they worked their magic on me.

"We need you at your hardest so that you can smash our holes," Replied Oreillan, coming up for air.

"Oh, I'll smash them alright," I replied, "But first I want to play a game."

"What game?" Asked Dee, looking up and smiling.

"The kink Olympics," I announced, pleased with the name I devised.

"The what?" Asked Oreillan incredulously.

"The kink Olympics consist of a series of competitions involving our arseholes, a kitchen funnel, and enema bottles, warm milk and, if you're up for it," I said addressing Dee specifically, "our bladders."

"Whoa!" Exclaimed Oreillan, "What shit have you been smoking?"

"Challenge accepted!" Dee replied with a smile.

"You?" I asked turning to Oreillan who was also smiling.

"Definitely," Came the answer I wanted, "Sounds like fun."

"Let me get my 'kit'," I said, climbing out of the spa.

The girls giggled before embracing and passionately kissing each other.

Grabbing the funnel, the enema bottle and the milk, I suddenly remembered lubricant.

I placed the implements on the table next to a black sharpie and an open notebook with three named columns ruled on the page to record the winner of each competition. Next, I grabbed two chairs and positioned them at the edge of the patio facing the lawn.

The ladies watched my preparations intently and drunk their wine.

I unscrewed the nozzle from the enema bottle and poured a serving of milk inside it. Next, I used the lubricant to grease up the nozzle and the shaft of the funnel.

"Impressive," Hollered Oreillan at my preparation.

Dee giggled like a child and offered similar encouragement.

"You ladies ready?"

"What's the first competition?" Asked Oreillan as she stepped out of the spa, water cascading down her curvy cougar body.

"The first heat is timing who orgasms first from my tongue," I said, pointing the ladies to the waiting chairs, "Just a warm-up."

The cougar and the MILF laughed in unison.

I grabbed a towel and placed it on the ground next to Oreillan, who sat in the chair with her legs in the air and exposed her delicious pussy.

"Grab my phone," I said to Dee, "Start the stopwatch after a 3-2-1."

"...and GO!" Giggled Dee.

And, I dived into Oreillan's sweet pussy.

The heat precluded the use of fingers. Tongue only.

Given that several months had elapsed since I met Oreillan, I knew how to use my tongue to bring her off. Clit, pussy and arsehole all need stimulating to bring her off. Not each orgasm took the same time and I knew that Oreillan could not be hurried.

Winning was not the issue.

It was all about the oral pleasure.

Oreillan orgasmed in 3m:14s according to Dee.

Standing up with sore jaw, Dee grabbed me by the hair and kissed my slimy face.

"Your turn," I grinned after finishing the kiss.

"Yay!"

Oreillan took the phone and reset the stopwatch.

I sank to my knees again, and marvelled to Dee's pussy which I've only eaten once before. During our first threesome, I ate her out, but I had no idea if I got her off.

"...and GO!"

Dee had a quite different flavour to her friend and reacted differently despite employing the same technique.

Grabbing my hair, again, and forcing my face onto her clit, Dee's body shuddered as she came on my face in 3m:39s.

"What's next?" Asked Oreillan, enthusiastically.

"It's time to see how far you can squirt from your holes," I replied, nodding towards the enema bottle, "Pussy first then your arse."

Both ladies said in the chair with their legs pulled back.

Starting with Oreillan, I inserted the nozzle inside her pussy and squeezed the rubber bottle. She initially had trouble holding it in and the leaks were numerous. The constant laughter did not help the milk retention.

"Hold it," I ordered as I refilled the bottle with warm milk for Dee, "Keep it in."

Dee was able to hold her dose in her pussy easier than Oreillan. I wondered if she done Kegel exercises following the birth of her children.

After administering the milk, I walked, naked, onto the lawn and stood facing two milk-leaking pussies.

"...and GO!"

Both ladies flexed their muscles and two white streams of milk shot out of their cunts and onto the grass.

Dee won that round easily, by a clear foot or more.

More laughter.

"Flip over!"

The ladies got on their knees with their booty holes in the air.

I refilled the enema bottle and lubed up the nozzle, but I couldn't help myself. Dropping to my knees, I buried my tongue in Oreillan's and Dee's inviting puckers and literally made love to those holes.

"Sorry about that," I said, not sorry for rimming two such perfect arseholes.

Oreillan's shitter took two bottles of milk in her luscious bung while Dee took about one and a half bottles.

"Oh, that's enough," She wailed at me as I squirted that liquid deep inside her O-ring.