So, I just found this sub, and thought I'd tell a story that happened to me as a delivery boy, when I was 16.
I used to deliver pizza for the local place as a teenager, which was actually quite well-known in town. I usually worked the night shift. So, one day, at around 22:00 (my shift ended at 22:30), a woman called, and made an order. Every other guy was already busy, so I took it. I grabbed the pizza off the counter, and off I went.
So, I climb a couple of steps, and knock on the door, since there was no bell to ring. An older woman (early-to-mid-40s) opened the door, wearing a see-through bathrobe. She asked me to put the pizza on the table, and wait there for her to grab some cash. I agreed, and waited.
She came back, and was naked. No underwear, nothing. She asked me if she could pay with "something else", smiling seductively. Me, being a clueless, nervous 16yo, still didn't understand what was going on. Plus, I'm gay, so it really didn't do much for me.
"What?" I asked nervous and low-key confused.
She walked towards me and put my hand on her breast. As she did that, it hit me. "Oh shit" I thought, "this lady is trying to get in my pants!". I quickly took it off her.
"M'am, if you can just pay me… I'm gonna leave" I told her.
She asked if I didn't wanna "have some fun", to which I refused again, by telling her I was gay.
"Ok, fine" she answered, kind of upset. The order was $15, but she gave me $2. I told her to please give me the rest, because if she didn't, I would have to pay it off of my own money. She ignored me and started walking towards her room.
"M'am, please pay me", I said as I followed her into her bedroom. Now I realise she was trying to lead me on, but at the time, I just wanted her to GIVE ME THE FUCKING MONEY. I had already been there for 10 minutes, this woman was naked, going around the house, not paying me, and I was starting to get annoyed.
Anyways, I was standing close to her bed as she looked for cash in her wallet. She suddenly just dropped the wallet on the floor and literally threw me on the bed. She climbed on top of me, and started grinding against my crotch. When she started making out with me, I instantly got a boner, so she noticed. Well, she unzipped my pants, and I let her ride me. I had no condom, so I finished off inside her.
She got off of me, and told me to "come back for more if I wanted to", and then just giving me a mouthful kiss. Needless to say, I never did lmao. I grabbed my clothes, and left.