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r/Bestof I'm 19 and Dating a 40-year-old MILF

2025-09-07 Comedy
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rSlash
rSlash
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Description

Podcast: https://open.spotify.com/show/3hJo9o8qFqrblXu1Plkv8L Patreon: https://www.patreon.com/rslash Discord: https://discord.com/invite/VD6eYD3 0:00 Intro 0:08 Older woman 7:41 Obsessed "Sneaky Snitch" Kevin MacLeod (incompetech.com) License: CC By Attribution 3.0

Top Comments (10)

@cheesepuffs-zp7ye 2025-09-07

A nearly 40 year old pursuing a literal teenager then harassing them constantly when broken up with is nothing short of a predator.

782 34 replies
@alissonvonderlane862 2025-09-07

6:02 Wow! The audacity to tell a 19yr old they're immature while you can't accept 'no' as an answer! 🙄

762 5 replies
@HobieInTheBox 2025-09-07

People need to stop s*xualising young men being pursued by older women. I hate this argument but if the roles were reversed this would be a serious problem. What the hell is wrong with people not understanding it the other way around.

690 42 replies
@Ezekiel_23_19 2025-09-07

First story: Just imagine if this was a 19 year old woman and a 39 year old guy. It would be obvious how unhealthy and controlling the relationship is.

639 30 replies
@xKCAZxLEADER 2025-09-07

First Story: Geez, I wonder how her marriage ended. Sarcasm aside, I found it ironic she called OP immature and not ready for a real woman when she went bat-shit crazy over a rejection. Also, it's weird and creepy she went for someone not even in their 20s yet. OP dodged a bullet with this nutcase. Also, I found it hilarious she claim she never wanted to see OP again....but stalked him and cornered him 3 times before OP got the cops and security involved

374 10 replies
@Raven74947 2025-09-07

Calling your brother "my love" and caressing his bare chest... That's not even in the f'ing realm of normal. I've always been close to my sister, but if she ever did that shit I would absolutely freak out.

359 11 replies
@Xolivas1 2025-09-07

Story 2: It's already bad enough that the sister has some sort of incestuous brother complex for OP's fiance...but the fact that her parents are enabling it, is somehow worse. "Blood is thicker than water" my ass!

198 7 replies
@deadchannel726 2025-09-07

The whole "older woman" fetish thing is batshit insane. It's not even cute in anyway. If a guy did this with a 19 yr old girl it's creepy. But when it's turned around the whole thing is okay?

143 12 replies
@sanctuns5279 2025-09-07

S1: Well... at least now we know why that woman is divorced. Something tells me she was the one who got served the papers.

118 2 replies
@Dphantomfan369 2025-09-07

Story 1: even putting aside the insane age gap. This whole thing started with a boss, making sexual advances on one of her interns. On top of the 20 year age gap and the fact that OP is barely legal. And OP needs to talk to his parents or professor on taking some safety precautions. Because he used to work for her, meaning she probably has some of his personal information to stock him. Maybe even try to sabotage him professionally.

90 1 replies

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