Losing My Virginity At 18

I was a senior in high school. Both my parents worked second shift so I had the house to myself at night. Typically at night I’d sit on the couch wearing just a shirt and my tighty whities and masturbate before showering and going to bed.

At 18 I didn’t look up porn online. I typically watched a few dvds my dad had or a few vhs tapes he had of 80s porn. Then I stumbled across Craigslists causal encounters.

March of my senior year a guy messaged me after seeing my ad on Craigslist. He lived really close by. A 57 year old divorced dad. After a few emails back and forth I found out his daughters went to the same school as me and the one was in my class.

So we planned to meet at his place but on a Friday night when his daughters were at a sports game at a different school.

I rolled up to his place. Very nervous but my dick was rock hard in my tighty whities. He opened the door. Turns out I recognized him right away and he recognized me since he pulled the marching band trailer often! I was in band. He invited me in.

After the first few awkward minutes and promising each other to keep it a secret he took me to his bedroom. Instantly his jeans came off and he was standing in tighty whities. Then he took his shirt off. Excellent dad bod he had.

Then he came to me and took my shirt off then helped me remove my pants. I was already rock hard in my tighty whities and he said someone is ready. He then told me to get on the bed. He walked into his closet. He came back out with lube. He took off his whities before getting on the bed. Such a fat hairy soft cock!

Things moved fast from there. He took my underwear off then gave me my first bj. That alone almost made me cum. Then he instructed me to give him a bj. As I’m sucking him he’s feeling up my butt. Then he tells me to lay on the bed on my back.

He gets down and starts eating my butthole. I couldn’t believe how good it felt. He moved to sliding a finger in me. I was so tight. As he’s fingering me he asks if I’m ready to get my cherry popped.

He puts my ass on the edge of the bed. Grabs the lube. Put a huge glob on his fingers and rubs it on my hole. Then puts a huge glob on his cock. He grabs his cock by the head then lines it up with my butthole. Slowly he presses on my hole. After about a minute of pressing his head pops in me! I let out a moan in pain. He holds his dick in place telling me to breathe and relax. The first penetration is gonna hurt since your a virgin. After a few minutes I was completely relaxed and all the pain went away. He slowly slide in

He was balls deep. He had a slightly above average dick. Then he began to fuck me. He instructed me to jerk my dick. I came really quick. Minutes later he blew a big load deep in my butt. As he’s mid orgasm he’s moaning. And he’s saying congratulations your not a virgin anymore. We both laugh.

This happened on a Friday night around 7 pm. Once he pulls out he says I should take a shower to clean up. He tells me to not worry about the cum in me. It will eventually leak out out come out with my next bowel movement.

After I shower I’m getting dressed and cum starts dripping out. I tell him and he laughs. He said good thing you wear briefs.

Every time I talked to his daughter after that I always wondered If she knew. He became my hookup for the next 4 months. Then I moved away for awhile. But recently in the last few months we ran into each other and began having sex again. Nothing has changed with him too. Still a hairy dick in his tighty whities. He a,so hasn’t had much sex so he’s loving using my ass