You’ll lick the cupcake

After hearing your options, the cupcake sounded like the easiest chance for a win. And though you’d never had sex with a Femboy before, as long as you won it felt like it wouldn’t matter. You ask Penny if you can have a go at him, to which she responds “of course! Here, we have their profile loaded, take a look while I go let them know.”

Penny hands you a tablet with the Cupcake’s profile, stats, and record. His profile pic was a cute if androgynous person,, wearing pastel colored sports bra on a flat chest, tight bikini bottoms over a small bulge, and a metallic collar locked around his throat.

He was actually your height and weight too, and may have looked more like you except the feminine hair cut and slight makeup. His record showed 3 wins and 8 losses, with the last 3 matches as losses against feminine opponents. Oh, it looks like he has had multiple appearance on the multiple other sites as well, from the public humiliation site to the Femdom and Futa sites. After seeing all this, you were fairly certain you had this win in the bag!

Just as you finish looking over her profile, Penny comes back. “Good news,” she says as she grabs the tablet from you. “The Cupcake is all set to go, even picked out what site to send you to if they pull out a win. They do want to know if you’d like to up the ante, specifically if they win they not only want you on a site, but to feminize you as their sissy until then. If you are willing to risk it you can propose your own ante as well.”