r/DirtyConfession•
CRK_76

My supervisor and her friends tied me up and tried to guess my dick size.

NSFW

This is a game I played with my girlfriend many times. Last night me and my girlfriend were over my supervisor Shannon's house along with four of her girlfriends. As my girlfriend was getting drunk, she was talking about my dick, saying it was a nice size. Then she wanted everyone else to guess how big it was. I thought this would be a lot of fun. Everybody wanted to play.

She wanted me to get naked. She would make sure that I was hard. And then everyone else had to guess how big I was. The winner would give me a blow job. Before we started gf gave me a safe word.

Then she took off my clothes. She didn't have to touch me. I was already rock hard. Shannon and her four friends guessed. One of her friends, a cute brunette, guessed correctly - 8 inches. I sat on the edge of the couch, waiting for my blow job, but everybody decided that I should be tied up to a chair. I agreed.

After being tied up, Shannon's friend grabbed my dick with both hands and started stroking me for a few minutes. She was really teasing me. She said she wanted me to beg for the blow job. After a while, I was going crazy and I begged her to suck my dick. She started blowing me, and I was so horny that I came in a few minutes. She swallowed my load.

I thought I would be untied, But she started stroking my dick again, and I got hard again in a few minutes. She started sucking my dick. It felt amazing. I lasted a lot longer. I held out for as long as I could. I came a second time and she swallowed me again. She won the bet but I got drunk and got two blow jobs so I definitely won too.

Posted Jun 10, 2026, 4:24 PM UTC

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