I was chatting with a guy I’d met online. We were both hard, both jerking off. He suggested a game, a bet to make things more interesting. “Let’s measure,” he said, “If mine is smaller, I send you a picture of my mom. If your is, You will send me your sis.” I knew I was at a disadvantage, but the thrill of it, the taboo, the risk, it all made my cock throb. I agreed.
My heart was pounding as I measured, confirming my suspicion. My dick was tiny, even soft. I sent him the measurement, a mix of guilt and excitement churning in my stomach. He won, and I lost. I had to send him the pictures of my sister. I scrolled through my phone, found a few recent ones, and hit send. My cock was rock hard, leaking pre-cum as I imagined him looking at her, imagining what he wanted to do to her.
A few days later, I got a notification. He’d posted her pictures on a random porn site, calling me his “cuck brother with a small dick.” I felt a surge of shame, but also, to my surprise, a twist of arousal. I was a cuck, a pathetic little man with a small dick, and everyone could see it. My sister would never know, but I did, and that was enough. I jerked off to the thought, to the humiliation, and came harder than I had in years.
