Hollywood's Hot Cougars 02: JenCourt

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Jennifer Aniston, Courteney Cox have one last threesome.
7.7k words
4.35
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Part 2 of the 9 part series

Updated 10/03/2022
Created 09/24/2014
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Robertdoc
Robertdoc
769 Followers

September 21, 2014

Tomorrow, much of the TV loving world would be divided between remembering the 10'th anniversary of the Lost pilot, and the 20'th anniversary of the Friends pilot. With a sprinkling of 15'th anniversary West Wing pilot memories buried within.

I for one was buried in Friends memories that day. And in two of the friends the previous night. But we'll get to that. We need a lot of setup first - much like a pilot, really.

Let's start by establishing that I was six years old when the Friends pilot premiered. Let's further explain that 20 years later, I was serving people in an LA coffee shop. And no, it wasn't Friends based - despite how both Jennifer Aniston and Courteney Cox drank there. That's the important thing since that's how I knew them.

Sometimes I served them separately, other times they came together. It was less frequently together during a stretch in the first half of 2014. According to the tabloids, they were feuding while in the midst of their separate engagements - and from what they later told me, it wasn't that far from the truth. Yet by June, I started seeing them come in together again.

Even as Jennifer's wedding neared and Courteney's engagement started that summer, they kept going to my shop just by themselves. It happened again on the afternoon of September 21, 2014 - right before Friends anniversary day, if your short term memory works.

I overheard them saying that since Courteney had an interview on Jimmy Kimmel on anniversary night, they would celebrate it tonight at Jennifer's house, without their fiancés or Courteney's daughter around. Or rather, they told me that to my face.

After they asked me what tomorrow was, and they needed to tell me it was Friends anniversary day. And after I said I hadn't seen much of the show, or the pilot, despite seeing them so often.

It's not like I didn't know every little detail, big event or running gag anyway. It was one of the shows big enough that you don't actually have to watch to know everything about. I was in the middle of explaining that when Jennifer and Courteney shared a look, and then suggested I should see the pilot anyway.

At Jennifer's house. With them. In the same room.

I was on autopilot for the next few hours after that. Somehow, I still followed the directions I got to the house, and got there at the time they instructed - when no one else would be there and no one would see me coming.

I should have suspected what else was coming right then. But we'll get to that too. There's still some more pilot-y exposition to get through.

Let's fast forward to after I looked around the house, got myself to comfortably sit in between Jennifer and Courteney, and watched the pilot on the Season 1 DVD. It was after a few easy laughs about how they looked and acted back then - though not easy enough to include a Rachel hairstyle joke - that I brought up just how young I was when this first aired.

"So back then I was about five times older than you. Now it's just less than half," Courteney did the math. "I feel younger after all."

"I was just four times older back then, so there you go," Jennifer pointed out. "Ah, things really were simpler then, though. Even in those first few years. The work, the laughs, the days when no one had Twitter, TMZ or iClouds..." She then did a kind of sitcom-y pause, as if waiting for some bigger punchline.

"And the threeways," Courteney delivered. It was more of a sucker punch than a punchline, really.

"Right, right," Jennifer agreed, as if I wasn't even listening. "Boy, we all know there were times we really needed those! All the times we really needed to get our minds off things. And onto different cocks. And people attached who were too grateful to blab about it."

"But then again, the pre-TMZ days really limited their options," Courteney went on. She looked at me once in a while, yet it was still hard to believe they were really talking to me. As if this was such a casual thing to talk about, like they would in thousands of interviews.

"We slowed down when our love lives and Twitter stock took off. And when we...had a rough patch or two," Courteney admitted. "But now we got past it at just the right time."

"She's right. We're both getting married soon, and we made it through 20 years of friendship. And the tabloid and sex stuff to go with it," Jennifer said. "If ever there was a time to be nostalgic for those old days...and recapture them one more time before we try settling down again...this is the best night possible."

"Hold on," I accidentally said out loud. But I was too busy putting the pieces together to take note. All this scandalous talk, inviting me over when no one else was around, making sure I arrived when everyone was long gone...the very premise of inviting a near stranger to a movie star/TV icon's home with her TV icon best friend...

"Oh," I let out. I knew I should have done better than that. But to buy time, I asked, "Why me? Luck of being on the right shift?"

"That, fitting and filling out the criteria, the novelty of someone who's still barely watched our show. A mix of that," Courteney answered somewhat.

"I watch Cougar Town, though," I informed Courteney. "Does that count for or against me?" I wondered. I hoped her laughter was a good sign. Wait, so now I was hoping for...

"You were already ahead, don't worry," Jennifer assured. "I mean, if this was 15 years ago, you'd be a dime a dozen. But after all these years, all the wear and tear...to still get guys just like you interested, who don't even know us best from Friends...that's a confidence builder to recapture old times with if there ever was one."

"And...what makes you think I'm interested like that?" I found myself asking. I barely had time to take this in or think this over, so her answer stood to be helpful.

"You're still here, aren't you?" Jennifer noted. "It's getting obvious how much you want to be here," she went on, her eyes gazing down at me. I looked down at myself and saw the proof growing underneath my pants.

"Well...it still might not be for the right reasons," I babbled. Perhaps this was a poor attempt to be playful, even if it sounded like I was trying to talk her out of it. "With your offer, I could be like this no matter who you guys are. Or what age you are. Or what I know you from."

Jennifer just smiled, which shut up all my objections, serious or not. Since she wasn't talking and I had shut up, I just looked at her. The way she looked at me, and the way she sat next to me in her white shirt and tight blue jeans was...cute, pretty and sexy all at the same time. It made sense.

I didn't know if Hollywood touchups - by makeup people or other specialists - were more responsible than her for making her still look fit and hot in those We're The Millers strip scenes. But it seemed to match up with the most recent bikini shots of her I could remember.

For whatever reason, she was in her mid-40s with about the same round breasts, rounded ass, trim figure and slender legs. Stuff she was offering to me...which she had apparently used in many threesomes before...which she must have gotten really good at with the practice...

Once I looked back up at her face, it clicked. There was no more need for jokes, exposition or adding. Jennifer and Courteney wanted to celebrate this big day for them with me...and with each other too, apparently. So be it.

But me and Jennifer were going first.

Jennifer's lips quickly landed on mine, and before long, her hands landed onto my chest as well. I indulged myself in that before reaching down to start lifting my shirt off, and she then got on my lap before doing the same.

While I was bare chested, she still revealed a purple bra underneath. It still revealed and pushed up her enduring chest pretty well. Below, I put my hands on her waist and started rubbing her smooth, still taut skin, until I went down to the top of her pants.

"On it," Jennifer stated, getting on her feet to start working on her pants. Once she was able to slide them down, I could see a matching pair of pink panties before I focused more on her exposed legs. She stepped out of the pants and then went right back on my lap, feeling just how impressed I was now.

I felt an aroused growl bubbling in my throat, as Jennifer's figure was fully exposed and starting to grind on me. But I wanted her to feel even more.

Without warning, I put my right hand above her underwear and carefully moved to dip my fingers in. When Jennifer didn't tell or signal me to stop, I dipped them deeper, brushed past her hair and went lower to brush her center. At the same time, my left hand went onto her bra and cupped her covered, soft left breast before reaching over to the back.

I let my right finger glide over Jennifer's lower lips, just enough to make her moan as I pulled my hand out. I needed it to help unfasten her bra, and when I got the hooks off, Jennifer took my hand and put it back down.

It reached its destination as Jennifer shook off her bra, showing her breasts in full. They had to be on the borderline of a C-cup, even now. Either way, I latched my mouth onto her stiff right nipple, as my right hand rubbed her pussy deeper and my left hand went down her back.

I was feeling up her pussy and ass and sucking her breasts by the time I heard a groan nearby. It helped me remember Courteney was there too. But she made herself harder to forget when I saw how her hand was down her skirt.

"Don't stop on my account. Don't you fucking dare," Courteney told me, before gasping out her next few sounds. She was playing with herself harder while I was playing with Jennifer at the same speed.

Well, if I was putting on a show, it had to be worth the admission.

I stopped and had Jennifer go back on the couch, then I kneeled down in front of it and her. She then had to lift her hips up so I could take her panties down, leaving her completely naked. Seeing a naked Jennifer Aniston naked and hungry for me only made me spread her legs and dig in harder.

It helped me ignore the uncomfortable hardness in my much more confining jeans. It did seem unfair that she was the only one exposed like this so far. Maybe Courteney would have to take things off before long as she pleasured herself to us. At the rate I was going, she'd have to hurry up.

My right fingers switched back and forth between rubbing Jennifer's pussy, fingering it and teasing her up above. My left hand mainly worked on her nipples, however. Combined with my tongue on her, and how I sucked on her a few other times, it didn't matter.

"Oh yeah...oh, fuck me...so eager...even back then they didn't..." Jennifer couldn't finish in words after I tongued her clit.

"No they didn't...mmm, I can't wait...you were right, Jen," I heard Courteney groan next to me. So this was Jennifer's idea first, then...as if I needed more incentive to dive my tongue in deeper.

"Oh, shit! Does happen once in a while, Court! God, it's gonna happen real soon..." Jennifer gritted out. "Come on, I've been ready all day...fuck me right now..."

"You mean with this?" I asked, lifting my head up and inserting my right index finger. "Or..."

"No! Just that'll do," Courteney answered for Jennifer. "I may not finish before her, but you're not finishing early either. Not till I get a chance to make you," she teased. "But first, I want to see her cum again...make her cum and set the bar for me. On both of you."

If she put it that way, then I'd really have to lift that bar.

I tried by sitting up and letting Courteney see me insert two fingers into Jennifer - who clearly saw it too. They watched and both groaned, for different reasons, while I wiggled and fucked my fingers inside of Jen. In addition, my left hand took its time cupping and massaging underneath her bouncing breasts.

"Oh damn, look at her...just as I remember," Courteney got out. She then stood up and got her skirt down, showing us both her black panties underneath - which she shoved her right hand into. "Jen..." she moaned as she and I moved our fingers faster.

"Court..." Jennifer cried out. To make sure she didn't forget me, I bent down to deeply suck and nibble her left breast, as I curled my fingers. "Oh, Goddamnit..." She reacted.

Her hips rose up and thrust against my fingers, even as I pressed against her and tongued her nipple. I looked back and forth between Jennifer and a still standing up, still masturbating Courteney, just as Jennifer kept looking between us. One of them would have to go off first from all these combined sights, sounds and feels.

I had one last ditch effort to make sure it was Jennifer. It involved quickly kissing and sucking both breasts, then dipping back down, fucking her harder with my fingers, and then putting my mouth back on her. After several seconds of rapid tongue and lip work, it paid off.

"Oh fuck, here I...fuck!" Jennifer cursed, sounding too hot for must see TV. Her cumming on my mouth wouldn't have gotten by the censors anyway, even in pre Janet Jackson nipple-gate days. Neither would Courteney bending down and fingering herself harder at the sight of it.

In the middle of licking Jennifer clean, I turned my eyes to see Courteney gazing down at me. She saw how wet my mouth was with her friend - then promptly leaned down to kiss me and taste for herself.

Her tongue went all over my lips and dipped past them, all while she moaned on my mouth - probably from tasting Jennifer and from still fingering herself. But she broke off and took her hands off herself soon after, before standing up and reaching a hand out for me.

I took it and then promptly felt that hand, and the wet finger it contained, brush my lips. I got to taste a bit of Courteney this time before she pulled it away and said, "I guess I didn't really taste you back there. Let's go upstairs and fix that."

"Okay..." I said in a daze before remembering something. "Wait, did you...get to where Jennifer did?"

"Not quite. Jen, whenever you're ready, come up and help me the rest of the way. You started it, you should help end it," Courteney said. "By that logic, you should help end his first round too, but I called dibs."

I briefly saw Jennifer nod while catching her breath, until Courteney picked her skirt and my shirt up and took my hand. She led me over to Jennifer's staircase, up it and then down the hall to what I assumed was Jennifer's bedroom.

Just as I sat down on the front of the bed, Courteney had already dropped our clothes in a pile, and thrown her shirt right onto it. Like Jennifer, she had a matching bra and panty set, only hers was black. And at 50 years old, she too revealed a body that many half her age would have killed for and spent a lot of money on.

Between her impressive breasts and cleavage, svelte figure, sexy legs, big smile and piercing blue eyes, I knew I couldn't keep my pants on any longer. She made her way over to me as I finished unbuckling them, but she got me to lie down before she finished lowering them for me.

Once my cock finally popped out, Courteney wasted no time getting a hand on it. I still got myself to back up so Courteney could get on the bed, then she laid herself in front of me. Putting a hand back on my cock, she settled down and slowly licked up to my underside, which she quickly pressed her lips against.

Courteney's mouth slowly consumed my head, while mine was gritted tight as I tried to hold on. But Courteney sure as hell wasn't helping - not with the way she sucked me in deeper and glided her tongue over my shaft.

She came off and slowly kissed and licked down my cock, making a visual show of it. My hips involuntarily went up, a sure sign I would be going off pretty soon. However, Courteney put her hand on my balls and tugged them just right enough to make me come off the edge, without cumming.

"I still got time to kill before Jennifer gets up here. I want us occupied the entire time," Courteney told me, then went on to take me back in her mouth.

"Me too..." I hissed, now better able to lean back and just enjoy Courteney Cox sucking my cock.

She sucked me deeply, then just used her tongue over my head and tip. She started stroking me as she came off, stuck her tongue out and let me see it work my head. After that, she bent down to take my balls into her mouth while her fingers stroked my head - but her other hand soon went back on my sack to keep it under control.

I breathed heavily and watched her work, particularly when her pleased, deep eyes looked up at me. I then heard footsteps and saw Courteney's eyes darken, an extra clue to what - who - was coming after recovering from cumming.

Jennifer dropped her clothes from her arms, then walked over to us, fully naked right next to a naked Courteney. She sat up on the bed, put her hand into Courteney's hair, and helped guide it down my cock even further.

"Good, I still get to see you take his cum," Jennifer said. "And while I'm at it..."

Jennifer went behind Courteney and pulled the back of her panties down, giving her room to insert her fingers behind her. Her audible reaction went right on my cock, and she gripped my balls perhaps a bit too well.

Once things got pleasurable again, Jennifer finger-fucked Courteney as she sank her mouth deeper down my shaft. When Jennifer guided Courteney's head down harder, I carefully put my hips up to start pumping inside her.

Courteney was being fucked from both ends now, which had to get her closer than I was on my end. It just had to. Especially since me and Jennifer did inspire her to get a head start, after all.

She started quick and then finally finished quick, as she popped off me and groaned long and hard. Jennifer sunk her fingers in all the way as her friend came around them. all while Courteney squeezed my cock with her right hand.

Courteney breathed heavily on me, which still wasn't quite enough. Her grip loosened, then came off altogether - only for Jennifer to take its place. After she licked her right hand clean, of course.

She put her left hand back on Courteney's head as it went down on me again, sucking my head as Jennifer pumped my shaft. But Jennifer let go long enough for Courteney to sink her mouth all the way down.

"Fuck, fuck, fuck," I repeated as Courteney gave me the deep throating of my life. She slowly slid her mouth up and made sure my cock was nice, wet and just about set to pop. When she came off and caught her breath, Jennifer used Courteney's saliva to help her pump me the rest of the way.

Breathless, I couldn't even warn them as Courteney's mouth went back on my head. She licked my head and tip, then opened her mouth to catch the first spurts of my cum. Jennifer stopped pumping and watched me shoot into Courteney's open mouth, which caught each shot from my cannon.

We watched her drink it down, right when I couldn't keep my head up any longer. I felt Jennifer let go and felt Courteney no longer breathing on me, hearing nothing but panting.

Once I heard Courteney sit up, I looked up in time to see something that certain fans must have imagined for 20 years. But apparently, Jennifer and Courteney making out was nothing really new. In fact, it might not have been the first time Jennifer devoured Courteney's mouth after it swallowed someone's cum.

But she swallowed my cum. And I was the one seeing this. Maybe I wasn't the first ever to see it, and maybe some would argue I'd have been more turned on 10 or 15 years ago. But I was seeing it now, and it was plenty hot now.

I rolled out of the way as Jennifer got Courteney on her back. "Jesus, it's even better..." Jennifer trailed off, not clearing up what it was. It could probably be so many hot things.

The hottest thing of the moment was Jennifer getting Courteney's bra off, then going down on her left breast. I gaped at Courteney's tits and Jennifer's oral work, at least enough for Jennifer to notice and wave me over. "Go on," she said, muffled by the breast in her mouth.

Robertdoc
Robertdoc
769 Followers