Ironic, right? Her name was VIRGINia.

My best friend from Bear Creek, a boy named Thomas, had a little sister two years younger than me. I wanted her even when I was around 12, and she was turning 11. She had the nicest *** I'd ever seen.

So one day, I was 16 and she was 15, we were sitting next to each other on the couch during a movie that her brother, his girl and another few people were watching.

I began to stroke Virginia's stomach and she didn't stop me. When I felt her C-cup breasts, she still didn't stop me. I even grabbed her ***. Then, I got up, hoping she'd follow me to my friend's bedroom. She didn't, but I beckoned to her about coming up. Then she did.

We were in the bedroom, kissing, when I produced a condom and she had her shirt, bra and pants off. I asked her if she was ready, and she sat for a moment before saying she thought she was. I told her I'd be extra gentle and she smiled and pulled her underwear off.

Her *** was AMAZING. Round, big, beautiful. I imagined my penis inside it, but I'd hold off because it was her first time.

So I undressed, and she *********** until she was a bit moist. I looked her in the eye, and with the condom on, I pushed inside her. She exhaled tensely, and I withdrew instantly. I asked if she was okay. She said yes, but she suggested we try anal.

This surprised me; she was a virgin. And it would be my first anal, so I was a bit surprised but she had a nice, round *** that I reached for with my hard penis.

I poured water on it first to act like a lubricant. I knew it wouldn't fully substitute, but it did make things easier.

When my penis went inside her ***, she gasped. It must have been painful but she told me not to stop as I drilled her.

It was great for me, but I was mainly worried about her. It wasn't great for her, and we never had sex again.
SethHudson11 SethHudson11
26-30, M
Sep 6, 2012