Finn's Punishment [Male version] (Pixiv Fanbox)

I met Finn as he was leaving the bathroom, after just finishing up administering his part of Emily's punishment. I decided it was time to have a little man-to-man conversation. I asked him about his crossdressing and his livestreaming business, but to my surprise he acknowledged that he wasn't making money off it at all. Now I don't know a lot about streamer culture, but I'm pretty sure the only reason to dress up for a bunch of strangers on the internet is to suck a mad amount of money out of their pockets. So, I asked him to show me his streaming setup.

While his girly clothes and wig were cute, I could see where he was going wrong: Not nearly enough sex appeal. He tried to protest, saying that his streams weren't sexual in nature at all. Well, no wonder you're broke. Your mother is useless and your family can't live off government handouts for the rest of your life. It's time to start earning your keep.

I ordered him to take off his clothes. And even though his lingerie was cute and erotic, I didn't think it was going to be good enough.

So, he stripped that off too. Timidly, he showed me the plug he was wearing in his ass. Apparently he had it inside almost all of the time, as it helped him concentrate during the streaming process. That gave me an idea. He was on the right track, but it's just that his body needed some more stimulation.

I tied him up and exchanged his tiny, flimsy toy for a more substantial one. He protested at first, but quickly succumbed to the pleasure of the new toy rubbing against his prostate. I left him to his own devices, and decided to visit Emily to see how she was doing.

After emptying my bladder and an hour of two of enjoying Emily's body, I returned to find Finn completely meek and unable to resist. His pale, hairless body was stained with his own semen as the toy in his ass had made him orgasm over and over again. Now, he was definitely ready to start his first new stream.

I carried him over to the new streaming setup I'd made for him, and changed up his bondage. As the camera went live, viewers started pouring in immediately.

The setup was easy: I'd leave him in this state, constantly being tormented by toys and the stares of the viewers, as long as they kept donating. It didn't take long for the first donations to arrive. At $50 an hour, it took him just a few hours to accrue several weeks of nonstop streaming. Now, with the family's monetary future secure, it was time for me to focus on the remaining two deadbeats.