My First

I lost my virginity to my boss who was my dad's friend and deacon at the church.

I'll call him W because that's the first letter of his last name. It was my first job after I graduated and was waiting to start college. He was my dad's age, so twice mine at least. He had a son a year younger than me. I'd known him all my life and it seemed nice of him to offer me a job answering phones at his business.

I was young, but not totally dumb. I definitely knew what it meant when he started flirting with me. I'd been so protected though, that honestly I was flattered and excited by the attention. My parents hadn't even allowed me to so much as date. I'm sure dad thought I was safe with his good friend W.

One night he asked me to stay late and I kinda thought he was up to no good where I was concerned. No, I wasn't really attracted, but he was a man and my hormones were wild. I went to his office knowing I'd give everything up if he asked.

He must have said something. I must have too. I honestly can't remember. I remember the locked door and drawn blinds. I remember his hands on my body, testing my receptiveness before we both ended up on the floor. I remember the feel of industrial carpet on my skin. Hands squeezing my breasts, lips on my nipples. It's amazing that I didn't cum right there.

He took off his pants. I'd never seen a dick before, let alone a hard one. He took my hand, showed me how to stroke it. Clear fluid seeped out and made it slick to the touch. I can't remember when my panties came off. I felt a moment of panic that this was happening when he got between my legs.

I wasn't prepared for how it would feel when he got in. Yeah, it hurt. It was a sharp, cutting kind of pain, but there was a deep, dull pain too that felt good in a weird way. I focused on that. I felt the pain throb with every thrust, felt myself getting wetter and hotter. The pain began to feel like pleasure and there was simply no turning back for me.

He pulled out when he came, shooting his loaf on my stomach. I hadn't reached orgasm but I didn't care. I was too wild, too high with excitement. I didn't cum the next time either, but I did on the third. My parents never found out and neither did his wife.

It ended when I left for college and never happened again. I did have a lot of fantastic sex with guys close to my age though. That first experience gave me a weakness for older men though.