Here's one that isn't from my college days. I had taken some time off from school to just be on my own for a while. I had moved to a new city and taken the first lame job I could find. This was back in the day when you could still reliably meet people online, before the bots moved in and sex workers took over all the forums. I didn't really know anyone and was just browsing ads to find anyone to hang out with.

I found a post from a woman who was looking for people to smoke with, in a similar situation of just looking for friends. I sent her a message and we chatted a bit before she invited me to come smoke at her place. She was 6 years older than me, not exactly a cougar but at the time it felt like a big deal to me.

When I get there, maybe to your surprise, she actually was who she said she was. She was a cute and thicc brunette with kind of a nerdy/punk vibe. She invites me in and we chill in her living room. We put on a movie and light up and just kind of chat and hang out. At first everything is just platonic as we hang. But I'm a handsy guy and as we are hanging out I cuddle up with her a bit, rubbing her shoulders and her legs. It's flirtatious but low key.

As I'm getting more bold and my hands are roaming further up her legs she asks me what I'm doing. I apologize and ask if I'm being too forward and she says "it's fine, just don't expect anything to happen." Since she doesn't want me to stop I decide to keep pushing it and see where it goes. I pull her a bit closer to me so she can hang one of her legs over mine and I can rub her inner thigh. Her breathing is getting heavier so I decide to try and reach under her shirt and massage her big tits at which point she decides to take off her bra.

She's still acting like this isn't going to go anywhere, but she hasn't turned down a single one of my advances so I know I'm good to go. As I mentioned, we'd been smoking and I have no idea how much time has passed, but before long we're making out and she's maybe half dressed. When she climbs onto my lap to straddle me she feels my hardon and asks what I have in my pocket. "Just my keys" I tell her and she reaches down to feel the shape of it in my jeans. "That's not your dick" she says in that way that's not quite a question, just a little doubtful. I nod to her and she just says "get those jeans off."

She hops off me and is kneeling in front of me while I sit on the couch. I unbuckle and start to slide my jeans off but she takes over and pulls my underwear off with them and tosses the bundle to the side. She takes me in her hands and as she's inspecting me says "now that's a biiiigggg fat dick."

I ask her if that's a problem and she says "no, it's great, I've just never been with anyone close to your size." She starts to kiss it and tries to give me a blowjob but it's obvious she has no idea what she's doing. She apologizes for not being better at giving head, but I don't really care, I'm having fun anyway.

She decides to give up on the blowjob and apologizes again but leads me to her bedroom. She asks me to lay down and climbs ontop to ride me. She's squeezing her eyes shut as she eases herself down onto my cock saying "fuuuuck that's good." We fuck like that for a little bit but she's getting overwhelmed so we switch positions to doggy.

She has her face down in the pillows and I grab hold of her nice big ass as I pound her. She's absolutely screaming into her pillows in this string of obscenities and how much she loves my huge cock.

We end up going at it a few times and afterwards she tells me "Well I wasn't expecting any of that" which says a lot about how different meeting people from the internet was back then. We "date" for several months after that. I say "date" because our relationship was one where she would pick me up from my shit job and take me back to her place, she'd make us dinner, we'd split a bottle of wine and smoke up, and then would fuck until we both literally passed out. Then she'd drop me back off at work the next day and repeat.

The only part about it that I didn't like was how she would occassionally show me off to her friends in the strangest way. She'd bring me to one of her friends' apartments to introduce us. I'll call myself John here (obv not my real name). We'd swing by their place and go in and she'd just introduce me by saying "THIS is John" and it was clear they already knew everything about me. If it was a girl they'd give me this flirty knowing look or check me out, which was fun. But she would also do this to introduce me to her guy friends, which just lead to the most awkward moments of them giving me that flat unamused look that said "cool, so this is the guy with the horse dick." And that was it, then we would leave, the only reason we stopped by their place was so she could show me off. We didn't hang out with them, we still just went back to hers for our usual dinner "date."