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LR  2nd ever lay with MILF/Cougar on my birthday today

770

Space Monkey
space monkey
Joined
May 27, 2025
Messages
19
More like a vent than actually educational.

Just turned 24, had birthday sex with a milf/cougar. She's 40 and looks around 30 since she's extremely fit, never had kids, and Asian. I admit I wanted to try her because of the age gap being a turn on, but she's also elegant and attractive in a way I can't exactly pinpoint. She just turns me on and I don't know why exactly. If I had to say it's her cuteness, maturity, and grace. She just dresses young and has a soft sweet voice with an slight Chinese accent. Her smile is sexy. But she's obviously not conventionally pretty or anything, she kind of looks like the girl next door except obviously older looking. Probably like a 6/10, maybe the shitty sex makes me biased towards lower but idk.

Here's why I have mixed feelings, I mean this is the first woman I've been with since my ex, who I was with for 3-4 years and was a HB8. The milf wasn't as excited to fuck me as my ex was nor was she as tight (obviously she is more experienced), I would get hard and then get limp while fucking her. I think mainly it's because I didn't feel that she felt much pleasure and that was kind of turn off. She didn't look that hot when she was turned on like me ex was (and doesn't really look hot in general). I admit I did masturbate earlier in the day because I was so horny thinking about fucking the milf. My sex game is probably pretty fucking bad but idk. I did get kind of sad and self-conscious about the fact that my ex was way hotter (might have contributed to limp dick), yet I am kind of confused because I also find this woman pretty attractive in the right moments, though it's more like searching for it compared to my ex who when I first fucked her at 18 was probably 9/10.

This lady has a lot of turn-offs (not very expressive in and out of the bed, pretty shy and pessimistic personality. But maybe these will change) and unique turn-ons that aren't present in younger girls (listed before but an additional one is how she's willing to submit to me despite being way older), not really sure what to do think she's down to keep it casual and I don't mind seeing her again. Maybe once we properly fuck and I don't have performance anxiety / stop watching porn it will help.

In the mean time, I'll keep trucking with other girls, still can't figure out if this should be a confidence booster or not in my head. I'm just waiting for the moment when I get a real stunning babe that blows me out of the water and finally get the ghost of my ex off my back. But this lady isn't half bad, the idea of her with me is still kind of enticing, just for the novelty, I mean she is truly different than girls my age. She does feel like a true woman but yea... idk.

Besides that, I quit my software engineering job to focus on dating and travelling, but haven't gotten to the travelling part yet. Sometimes I feel insecure about quitting everything to focus on seduction, but if I don't do it I'll never find a woman who eclipses my ex. So fuck it...

I would write a report on the time before the lay but honestly I think she was kind of DTF as long as I didn't act abnormal. From what I understand I'm the youngest guy she's dated but idk if she's lying LOL. Though I think she was plesantly surprised by the hand holding and my cuteness on the first date, as well as my interest in art apparently. At least she opened up some possibilities for me in my head about getting older girls. Maybe I'll write the pre-lay stuff later for my own purposes.
 
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orkie123

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Feb 21, 2023
Messages
225
Congrats on taking the step to focus on seduction. Society likes to tunnel vision us which can make us feel guilty for straying outside, but all the stories you will make travelling and dating will be worth it.

I also sometimes have ED problems. Porn doesn't help, but a major factor is whether I can feel that the girl is feeling pleasure herself like you said. Some girls are just more quiet even if they enjoy it, but if they are not good at expressing their pleasure and I cannot guide them to get there, then I often lose interest. I'm sure sometimes it's my fault and they probably like something different, but some girls really are just not the expressive/active type during sex.
 
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the right date makes getting her back home a piece of cake
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