Yes

You try to imagine it - Bob in a dress, covered in your silver sperm - it would be a fucking fresco. You start to grow hard again.

"Yeah, lets do it!"

"Yes! Alright, let's go online now to order it!" He sounds just as excited as you. He doesn't really imagine he'll win, does he? Maybe he's just so eager to fulfill his sissy fantasy, you laugh to yourself.

You both spend a few minutes together browsing Amazon, reading the reviews and comparing products, but you soon run out of patience.

"Let's just pick one already. Who the fuck cares if it's made from polyester?"

You leave Bob and grab a beer from the fridge. By the time you come back he says he's done and there's an awkward silence as you both realize that you still have the whole day left to spend. You hang out and order some pizza but after a few hours it's clear Bob doesn't want you around anymore, and frankly, you want some time to yourself as well. You drive home and do some chores before heading to your room to relax, but you can't get tomorrow out of your head.

You need to jerk off, but you can't cum. You want a sure win tomorrow, and you'll have to cum as quick as possible. You decide to go on imagefap and find some sissy captions to jerk off to.

'Sissies like alpha cock' Like mine.

'Be a good beta and serve your master' Get down on your knees, Bob.

'Good boys lock up' Oh FUCK. That's so hot, you can't wait to emasculate Bob into chastity.

'Real men don't wear panties' OH YEAH, Bob, you shouldn't be wearing panties you dirty slut. You're gonna make me cum you whore. Ah! Yeah! I'm cumming!

Shit! You weren't supposed to do that! Fuck!

Well, no use getting upset. You've won 3 out of 4, you're sure you'll win again. No problem.