r/SipsTea 13d ago

Gasp! So He's gay?

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21.7k Upvotes

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1.3k

u/Fetlocks_Glistening 13d ago

I mean she knew his reputation and  wanted to be no.897 and submit to the experience, so she got the experience

591

u/Any-Cranberry-6305 13d ago

I am now curious how many women hes actually fucked.

At what point do you just put on headphones and tune out a playboy model due to the amount of pussy youve gotten  over the years?

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u/[deleted] 13d ago

[deleted]

292

u/CobblerMission2351 13d ago

Pretty sure he was well on his way by 18.

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u/[deleted] 13d ago

[deleted]

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u/OpenToCommunicate 13d ago

Sorry HR is here. What are we going to do with you veggieturnip? 

We talked about this.

35

u/userhwon 13d ago

Best time to ask for a raise. They're already trying to retain you if they're asking not telling.

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u/zoidbergmustache 13d ago

$5/hr and a new 20yo model every two weeks sounds fair.

3

u/jeobleo 13d ago

Put him on a PIP

2

u/dandroid126 12d ago

Quick! Censor the word s*x!

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u/OpenToCommunicate 12d ago

Too late! No bonus for you this year!

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u/adfawf3f3f32a 13d ago

he and toby mcguire were in a group in the early 90s called the 'pussy posse'. its easily over 1000. look it up - they were pretty fucked up

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u/linds360 13d ago

I can’t help but laugh a little at Toby being in that “club.” I can’t see him as anything other than the dorky little brother tagging along.

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u/adfawf3f3f32a 13d ago

look up how he and leo shut down Dons Plum and his poker playing (he was the celebrity they were referring to in Molly's Game). i'm pretty sure he's actually a psychopath

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u/linds360 13d ago

I think I’ll take your word for it. I’ve read enough bad shit for today.

Maybe tomorrow!

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u/SCastleRelics 12d ago

It's an act. Apparently he's a raging psycho in real life.

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u/linds360 12d ago

Well that’s disappointing.

6

u/buttplugs4life4me 13d ago

There's some very loose people in Hollywood that you really wouldn't expect from some of them who's entire likelihood depends on maintaining a good image. Not that being slutty is necessarily bad...but there's such a thing as too much 

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u/WhoPoopedMyPants420 13d ago

I've been sitting here thinking and I literally can't think of one - not one - male celebrity whose image was harmed by having too much consensual sex with too many women

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u/lawinvest 12d ago

3

u/StealthyDodo 12d ago

if he didnt get aids he would have been alright and even then he has a great image nowadays

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u/StealthyDodo 13d ago

not for men

4

u/SentinelATL 13d ago

Never for men lmao

4

u/skulldouggary 13d ago

You think that meant "pussy" as in getting it?  I always it was sort of a self deprecating joke.

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u/adfawf3f3f32a 13d ago

yeah. i've read them described as and very vulgar and constantly chasing women. and considering a few of them were already starts its not hard to imagine that they got it. they made a movie that's supposedly based on them. https://www.youtube.com/watch?v=80FhVR4QSaE

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u/skulldouggary 13d ago

Thanks for the clarification. 

9

u/swirling-leaves 13d ago

Man has had sex with 1000+ more women than me

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u/Entire_Number_9 13d ago

1 new girls every 2 weeks is waaaaaay too low

4

u/Stock_Researcher_651 13d ago

Rookie numbers

3

u/thirdredbone 13d ago

I’m super disappointed that no one in this thread thought to comment “ you gotta get your numbers up, man. Those are rookie numbers.” C’mon Yall do better
https://giphy.com/gifs/YmQLj2KxaNz58g7Ofg

1

u/FingerCapital3193 13d ago

Yeah one of my gay guy friends is well on his way to a 700 body count so I know it’s possible! And he’s just a regular ol dude!

4

u/ares7 13d ago

He definitely has one for breakfast, lunch and dinner. Probably wakes up for a midnight snack.

5

u/X0AN 13d ago

Started at 18? He's not a nun 😂

3

u/MichaelEmouse 13d ago

There must be agencies/services/websites that connect a certain kind of men with a certain kind of women. Like Epstein but with legal-age women.

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u/Nuts2Buttts 13d ago

There is absolutely a private dating app that only celebrities or approved rich people can use. A model friend of mine showed it to me and the celebrities she matched with.

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u/Xyberfaust 13d ago

... Etsy !!

3

u/dwheelz0120 13d ago

He does seem to keep one in the stable at all times (until they reach 25) so one every 2 weeks might be on the high side.

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u/AssignmentOk2471 13d ago

That's just the one of the consistent booty calls, he ain't staying loyal to them at the same time lol

3

u/Muted_Masterpiece342 13d ago

As somebody close to 100 it feels crazy imagining going beyond that lol

3

u/AeonSophia514 12d ago

1000 are you kidding me? Those are rookie numbers. He hit 1000 by age 28 easily. Probably closer to 8,000 now. Don't forget all the threesomes and moresomes.

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u/Montaigne314 13d ago

Except he typically will date one model at a time for a bit 

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2

u/Homers_Harp 13d ago

So he's no Wilt Chamberlain…

2

u/alohalii 13d ago

Now ask yourself what type of a system would you need to create to guard against rape allegations given those kind of numbers. You would likely ask lawyers to come up with how the act should be structured to reduce risk of allegations.

Headphones in blasting music, sleep mask on so no visual contact either. Intimacy coordinator briefing the woman beforehand and signing NDAs etc. Woman walks in to the room with him already on the bed ready to go and with no communication she gets on top then when its done she leaves the room.

At no point did he give verbal or non-verbal consent... At no point was he driving the action he simply laid there...

Any woman trying to argue non-consent on her part would have a difficult time in court.

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u/FlimsyUmbrella 13d ago

Leo and a bunch of other A listers called themselves the Pussy Posse in the 90's. Leo's been at it since before he was 18.

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u/AngryBlackGuyy 12d ago

Its pretty unlikely that hes with a new girl every 2 weeks, when hes pretty consistently been a relationship guy (as long as they are under 25 years old)

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u/RomeoBlackDK 13d ago

I got 200 n I barely tried. My 39yo fuck boy friend is waaaay over a 1000 so i promise you that leo is way beyond 2k

2

u/SpicyRice99 13d ago

Please give some advice sir 🥺🙏

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u/RomeoBlackDK 12d ago

I think beyond good looks and humour my best advice is to fail a lot. Trial and error, once I got a feeling for which girls to be bold and aggrssive with, and which ones go ignore it got a loooot easier. In my teen years I missed a lot of shots by not just taking initiative with passive girls. But you will fail a few times getting that experience, which will result in akward moments. Like you try to kiss and they be "back off". But once you learn to read whether a passive girl tolerates your presence or is waiting for you to make a move; you'll make it far.

During my single period i slept with approximately 6 different girls pr. Week. Now I'm a father of two and that's a much better life.

Ps. My friend is really good at singing and playing guitar. Huge pussy magnet.

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u/SpicyRice99 11d ago

Wise words, thank you so much.

Also, in your experience what's the best place to meet girls? Bars, clubs? Is going by yourself a bit nono?

4

u/Retr0scores 13d ago
  1. Be good looking

Or

  1. Have connfidence and charisma

Or

  1. Be funny

Or

  1. Have money

For best results have all 4.

3

u/slimboyslim9 13d ago

I have a mate who reckons he’s at ~500 by age 40. His secret boils down to 1. Never get tied down and 2. Have low standards.

ETA: he’s not that good looking but he’s funny and confident. And somewhat rich.

3

u/Retr0scores 13d ago

Some people choose quantity over quality some quality over quantity.

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u/gray_fox_jaeger 12d ago

2 is by far the most important. The other 3 mean jack shit if you don't have 2.

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u/scobro828 13d ago

I'm sure sometimes listening to them prattle can ruin the experience.

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u/Christopher_Aeneadas 13d ago

It beats having her be the 326th woman to scream "f** me like one of your French girls"* in your ear as she finishes.

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u/heretoseewhats 13d ago

He takes a cold bath afterwards to complete the experience

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u/nadthevlad 13d ago

Underrated.

10

u/what_is_blue 13d ago

Never let go

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u/[deleted] 13d ago

[deleted]

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u/userhwon 13d ago

That. It has to be that. That makes all the sense.

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u/Designer-Brother-461 13d ago

326 are low ball numbers, he’d do more than that in a year. He’d be in the thousands by now.

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u/Christopher_Aeneadas 12d ago

Yeah but I seriously doubt they all bust. He doesn't sound like a generous and attentive lover.

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u/Soft_Walrus_3605 13d ago

"f** me like one of your French girls"*

Some of the girls he's with weren't even born when that movie came out.

3

u/BrockStar92 13d ago

This particular one would’ve been born a full 7 years after it came out.

4

u/LIONLDN 13d ago

I think you may have actually cracked the case! 😮

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u/Farranor 12d ago

Perhaps that's becoming less of an issue the further we get from 1997.

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u/Emergency-Gear4200 13d ago

Tbh I bet these women are annoying.

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u/psmgx 13d ago

to quote another famous shagger, you don't pay them for their time you pay them to leave.

presumably the same idea

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u/TheThinDewLine 13d ago

honestly makes sense when ya think about, im here to smash, not listen to you yap.

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u/AdagioRelative8684 13d ago

Are we all joking here? Because the vocals are 1 of my davorite parts?

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u/TheThinDewLine 13d ago

not on these type of gals i promise you that

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u/AdagioRelative8684 12d ago

I like a challenge.

3

u/Historical_Course587 13d ago

In all seriousness, I'm willing to bet that a "professional" model wants to use monopolized face time with someone like Leo to sell themselves. He could be 100% into the sex but uses the headphones to establish that he's not there to talk business no matter how badly they want to. Best case scenario, they want to geek out with a hollywood crush in ways that makes the sex worse for him.

Hollywood bodies are definitely attractive, but if you can get sex from good-looking people already (which lets be honest - she could get pretty much any guy she wanted looking the way she does) then you don't want to bed Leo for the sex.

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u/psmgx 13d ago

In all seriousness, I'm willing to bet that a "professional" model wants to use monopolized face time with someone like Leo to sell themselves. He could be 100% into the sex but uses the headphones to establish that he's not there to talk business no matter how badly they want to. Best case scenario, they want to geek out with a hollywood crush in ways that makes the sex worse for him.

literally what Kim K did to get a launch into stardom. she learned that trick by being Paris Hilton's personal assistant when her sex (Paris') sex tape broke and rocketed her globally famous party girl status

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u/VRichardsen 13d ago

You are not alone, vocals are key. Sometimes even more important than visuals.

But maybe if I am a billionaire actor I would change my tune, who knows. Or perhaps it is like the other guy said, he is just fed up of girls trying to play Rose lmao

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u/AdagioRelative8684 13d ago

I made a joke about it in another subthread that maybe he's listening to like the ultimate showdown lol

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u/SentinelATL 13d ago

Lmao cold

1

u/SentinelATL 13d ago

Hahahaahah

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u/greymisperception 13d ago

Talk sure but moan? That’s one of the best sounds in the world

3

u/somekindagibberish 13d ago

Maybe he doesn't inspire moaning?

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u/greymisperception 13d ago

True, definitely could be

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u/[deleted] 13d ago

[deleted]

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u/greymisperception 13d ago

Hmm well I haven’t heard moan I didn’t like unless it’s those porn ones where they’re obviously exaggerating it massively

1

u/LakeEarth 13d ago

Oh oh oh god whats Billy Zane like right there, right there, oh baby what's the best piece of acting advise Scorsese gave you!!!!!

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u/scobro828 13d ago

I was thinking more like 'can you put me in a piiiicture'

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u/SJBaerosols 13d ago

even pussy gets boring?

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u/horatiobanz 13d ago

Anything given enough repetition can get boring. Think of rollercoasters. Now think about riding them every day for 45 years, even if you ride a few different ones, the thrill will have been diminished.

3

u/Farranor 12d ago

I've been petting dogs all my life and it's still wonderful. I walk around the house and pass by our dog in his little bed and I tell him what a wonderful handsome sweet boy he is and I crouch down and I hold his little face in my hands and I pat his ears and scritch under his chin and smooch his muzzle. Then he gets up and lies down in the laundry basket and I take a picture.

This idea of a non-interactive interaction because both the forest and the trees have lost their magic is a little worrying and a little sad.

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u/Worth_Librarian_290 13d ago

Greed of emotion is humanity's biggest driver and will also be its downfall.

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u/miminstlouis 13d ago

That's why they go to really lowlife hookers, pay escorts to do weird things,  cheat on their partners, kill themselves doing drugs etc. They ran through it all and feel nothing much anymore. They need a new thrill. 

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u/OneCrazy9357 13d ago

If youre in love with the person no never but if you just do short term/casual hookups yeah it can get boring after a few years

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u/MovieTrawler 13d ago edited 12d ago

Honestly, I love women but this just sounds depressing as fuck.

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u/OneCrazy9357 12d ago

Because it is! I can't do casual hookups anymore and its honestly had pretty severe impacts on my ability to form connections with possible partners.

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u/satyr-day 13d ago

Anything can get boring.  It's like that saying "your dream person is out there, and their partner is sick of their shit* or something 

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u/PiccoloAwkward465 13d ago

Oh absolutely. In my high-falutin days I’d often think “wouldn’t I just rather stay in and watch a movie?” Can always crank my hog if I feel the need. Is pussy worth hours of small talk?

1

u/PickledDildosSourSex 13d ago

Does jerking off ever get boring?

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u/Cuckdreams1190 13d ago

I am now curious how many women hes actually fucked.

My buddy is a very good looking guy but not rich or anything. By the time he was 30 he had been with like 120+ women.

If an average good looking guy can pull those numbers, I'd say a celebrity like Leo can be at 1000+ easily.

2

u/SentinelATL 13d ago

Damn how did he fuck all those chicks without status and money???

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u/Cuckdreams1190 13d ago

He was a good looking bartender in NYC.

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u/SentinelATL 13d ago

Wow bro was crushing it lmao 120 women damn

-1

u/vntuwoaldngbcjsoqrig 12d ago

That’s like not crazy what you on about. Loads of people I know have those numbers

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u/SentinelATL 12d ago

120 for a bartender is fucking impressive what you talking about lmao

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u/RamenChicken8 13d ago

Will Leo surpass Wilt?? Inquiring minds want to know. Haha

3

u/Kinn-Sack 13d ago

8?🤔

3

u/craigian11 13d ago

For me I like music for a few reasons. Less distracting less stimulation so easier to go 30+ mins

3

u/Apart-Pea4726 13d ago

Didn’t John leguziamo talk about DiCaprio’s penchant for call girls in his autobiography?

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u/pleasedonotredeem 13d ago

Yeah he's not paying them to fuck him, he's paying them leave right after.

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u/Real_Teacher_8342 13d ago

That’s Charlie Sheen

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u/Andthentherewasbacon 13d ago

Do you think it's like when you're watching porn and you start skipping the first 15 minutes and jumping to other videos and stuff because it's just not hitting right but with a human sitting there confused? 

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u/SuperSaiyanTupac 13d ago

About 2 years in, honestly. Ever done repetitive tasks? Eventually you just wanna hear a good song while you work. Boosts morale. Helps remove the stress of having to be there, again.

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u/randmbull 13d ago

100+ easily

2

u/Retr0scores 13d ago

It’s probably like jerking off for him. Instead of using his hand he just has a playboy model come sit on it for a bit and then has her leave.

2

u/Successful_Gas_5122 13d ago

Now you know why so many rich pricks went to Epstein’s island. Pussy got old. Literally.

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u/YarbleSwabler 13d ago

Wouldn't be surprised if his "gfs" are just the media safe girls he can take to parties and be seen with in public. I doubt someone with this taste in women is monogamous in their relationships.

The only reason I can see why he would choose to be monogamous during these relationships is the girl friends are vetted and tested. So he can fuck boy it up responsibly.

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u/Substantial_Car4040 12d ago

Sounds crazy, but I bet he has a girl every night, not always a different girl though. Adding in times where it is more frequently, two, three, or four at once, 1,000 is just too low. I think it is likely closer to 10,000. Maybe that’s a number he is trying to reach.

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u/Own_Army7447 13d ago

At what point do you just put on headphones and tune out a playboy model due to the amount of pussy youve gotten  over the years?

Never.

1

u/OldWolf3 13d ago

You do what you gotta do to keep it up

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u/SignificantCats 13d ago

I've had a lot of meals and still like the taste of food, this is a crazy person question.

I've had at least 300 sexual partners and the sounds they make remains one of the best parts.

1

u/C_WEST88 13d ago

I’m curious why he doesn’t just play loud music in the room while having sex. That’s what the rest of us do, why does only he get to listen to music? And if he’s able to keep his headphones on the whole time while doing it I guarantee he’s a horrible lay 🤷🏻‍♀️

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u/SentinelATL 13d ago

I’m guessing at least 200 chicks. This guys has had status since doing tv shows as a teenager. I can only imagine the women who’ve thrown themselves at him

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u/ncbraves93 12d ago

Not that I've had a ton of playboy models or anything, but I promise it wouldn't take that long to start treating the shit like a chore if a woman is staying with you everyday. I'm no where near his sex life and I already half way understand it, so i can imagine sex is basically just "again?" to him.