I worked as a courier/delivery driver for a company that shall remain nameless.
I had always had encounters with women in bathrobes, without bras etc. but one day I went to the door of a middle aged woman (around 45). I'm 26.
I knocked on the door and was about to leave the package in her mailbox (we're instructed to do this if they fit). As I turned to walk away from the house, this woman opened the door. Easily the most attractive older woman I've ever seen.
She said, "Hey, where are you going?" and I turned around and saw her. Gorgeous red hair and and the roundest most perfect cleavage, peppered with freckles. As I saw her, I started to get hard immediately. I had always hoped a situation like this would happen but even in that moment, I didn't think it actually would.
She pulled the package out of her mailbox and said to me in the sexiest voice I've ever heard, "Don'tcha wanna know what I ordered?"
I was so enthralled with her beauty, I let out a timid "Yeah, of course". So she starts unboxing the package right there in her open doorway.
It's a vibrator. My cock is throbbing at this point and I can't hide my erection. So she says "Mmmm, you look happy to see me." and I said "I absolutely am" or something equally stupid.
She invites me in and it's clear to me this is her fantasy as much as it is mine. She undoes her purple, silk robe and her perfect tits just stay in place. I've never seen tits like this again, they must have been fake but they were unbelievable. She was completely waxed except a faint strip of red pubic hair and the most gorgeous cameltoe, which was already dripping wet.
She grabbed my hand and placed it on her pussy. I felt like I was going to cum in my pants. I start to rub her pusy and my hand is getting soaked. She starts to unbutton my pants, just slightly feeling my dick.
My throbbing cock pops out from behind my boxers and she gets down on her knees. She gives me the slowest, most sensual blowjob I've ever felt, just completely sucking on the tip of my dick like its a popsicle.
She stands up, while stroking my cock with her hand and she walks me over to her dining room table. She grabs a condom out of a drawer in the table and I think "wow, she's done this before".
She puts the condom on my ever expanding penis and opens up her pussy lips. She guides my cock in and moans so incredibly, that I nearly burst right there. I plunge into her and I just look at her gorgeous face and unbelievable freckled tits and I can't help it anymore. I tell her I'm going to cum and she tells me, "I want that cum on my tits".
So I pull out, and take off the condom. She wets my dick with her hand and starts stroking it against her tits, I explode all over her tits and neck and she scoops it up and licks it.
She then asked if I wanted to use the vibrator to finish her off but I said no, "I want to eat your pussy" and so I did.
I ended up getting a letter of reprimand for missing so many deliveries that day but I can say without a doubt it was the greatest day of my life.