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TIFU by realizing the older woman I’ve been sleeping with for months is my coworkers mom.

Throwaway account, this literally happened like an hour ago. So I (M25) have been involved with an older woman (F44) lately.

It started a few months ago with the onset of Coronavirus, I was on Tinder trying to find someone to hook up with during quarantine so as to stay safe and also kill some time. I saw this very attractive older woman and decided to swipe right because you know, it’s every 20-something year olds dream to hook up with a Milf. A few days go by and I get a notification that I have a new match. Wahoo! I open up the app and lo and behold it’s the fine ass cougar I was hoping for.

We start chatting and flirting, it’s going really well. Out of nowhere she messages me and says “I’m not sure how this app works, do we just meet to have sex or do we go on a date first?” I was drinking coffee at the time and promptly shot it out both nostrils. My chance had come. I replied back that people generally just meet up to go to the Bone Zone together but I’m easy either way. She replies “well good because I hate formalities” I nearly shit my pants in excitement. She sends me her address and tells me she’s free on Friday and to bring wine. The rest of that whole week was a complete blur of anxiety. I could not fuck this up.

So Friday comes, I show up with wine, she looks fucking smoking hot. Better in person. We talk about music and travelling and all that, not many personal details (which would come back to haunt me) just sort of arts & culture talk. A few glasses of wine later and were full blown going at it like rabbits on the middle of her living room floor. I left a little while later feeling like I’m the king of the entire universe and go to sleep.

The next day she texts me saying how she had a great time, and it made her feel young again and blah blah blah. She says she’s off every Friday and Saturday and that next week we should do the same.

This has been going on for roughly 3 months, we meet up once or twice a week, fuck like animals, and then go on our merry way until one of us gets horny again. Sweet deal right? Wrong.

I messaged her yesterday saying that I had today off of work and asked if she wanted to meet up, she said her son was taking her out to lunch, and that I could come over at 3pm. She had mentioned she had a son before but didn’t go any further and I didn’t really care to ask.

So 3pm comes and I’m almost at her house when she messages me that she’s running late; no problem. I park on the road and sort of just wait in my car because her car wasn’t in the driveway yet. I’m sitting there listening to the radio when an oddly familiar SUV pulls into the drive. I sorta looked at it funny and then I immediately realized where I knew it from. My coworker(M23) jumps out of the front seat, goes around to her side of the vehicle, gives her a kiss on the cheek and a hug and then jumps back in the car. My jaw was on the ground.

He reversed out of the driveway and stupid me is sitting like a deer in the headlights in plain sight. He turns around and is literally 10 feet in front of my car and staring directly at me. My face goes bright red and I feel like I’m going to vomit. Me and this guy work together every single day and I consider him a friend of mine, I even trained him when he started at my company. And the kicker is I’ve been telling him (in detail) about this older lady and he’s been giving me immense kudos about it saying that it’s “his dream”.

He pulls up beside me and looks very confused, asks me what I’m doing and how funny it was we ran into each other. I panic completely and stumble over my words and pretend like I’m on the wrong street and trying to find my cousins house. He looked skeptical but sort of shrugged it off. The whole time his mother is standing there watching us through the curtains. He directs me where to go and I pull off and then circle back once he’s gone.

Needless to say I went inside and told her what was up, and we both sort of sat there in silence before I left. No boom boom today.

I am now panicking, there’s no way he’s not going to know right? And he’s gonna realize all these wild escapades with this she devil night mistress I’ve been telling him about is actually his mom? Fuck. I already called in sick for work tomorrow because I cannot look him in the eye.

Will update if anything happens.

Pray for my soul Reddit.

UPDATE: she just texted me and says that we should tell him and come clean because it’s the right thing to do. WHAT THE FUCK. How do I politely explain that I’ve told her son in detail about our escapades including the time I dripped candle wax on her butthole? (she a freak)

UPDATE 2: she’s adamant about telling him, even after I informed her about the explicit details I’ve been sharing since we started doing this. What is wrong w this woman. I’m seriously debating quitting my job, I know her son well and he’s gonna want to fucking kill me. She keeps insisting that “he’s a grown up and he should realize that his mother is a person too with desires like any other person” THATS NOT THE POINTTTTTT. Fuck. I’m fucked bro’s.

UPDATE 3: she said regardless of what I say she’s telling him tomorrow, because she can’t “live with the guilt and deceit” she won’t answer my calls at all. Not going over to her house because she’s out somewhere. I’m fucked, will update again. Let my tombstone read “died doing what he loved best”.

TLDR; banging hot older woman for a few months, go to meet with her. Coworker drops her off and I learn that she’s his mother. He sees me waiting and seems skeptical about my lie as to what I was doing. My world crushes. RIP Me.

Edit; fix spelling / grammar

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Names have been changed to protect privacy

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