This is elias, m28. Since my first encounter with a woman notably older than me, I have not been able to not daydream of my experience. While looking for online sexting partners, I wrote down my true story and I’m happy I did. I hope you can find some joy in it.
So, my daydreaming of having sex with female strangers truly started here. Some two years ago I was “picked up” at the grocery store. An attractive lady, on the taller side (I’m 1m87 and she was maybe 10-12cm shorter), brunette and in her early fifties, glanced at me while we lined up for the cashier. She paid and exited quickly, but she did clearly wait for me outside. Our eyes met again and out of nowhere I grew the confidence to introduce myself. We were both notably nervous, but also very much aware of why we introduced ourselves. We talked a bit and decided to go for a coffee.
Not two hours later was I undressing in her living room. I was rather very fit back then, as I competed internationally, but I’ve always been shy. So my confidence grew quite much as she bit her lower lip giving me the affirmation that she liked what she saw.