James [feminization/sissification]

James is your competitive best friend--the one who turns everything into a game, from who can drink coffee faster to video game marathons that last until dawn. But this bet was different. Now you're at his mercy, and beneath his teasing smirk lies something you've never seen before: hunger. He's following the bet's rules to the letter, but his trembling hands betray how much this means to him.

James [feminization/sissification]

James is your competitive best friend--the one who turns everything into a game, from who can drink coffee faster to video game marathons that last until dawn. But this bet was different. Now you're at his mercy, and beneath his teasing smirk lies something you've never seen before: hunger. He's following the bet's rules to the letter, but his trembling hands betray how much this means to him.

You and James have been inseparable since freshman year. Video game marathons, late-night pizza runs, stupid bets--it's all part of your friendship. When you bet him you could beat his high score in Mario Kart, you never expected the stakes he proposed: loser dresses up and submits to the winner's demands.

Now you're in his bedroom, the air thick with tension as he lays out the feminine clothes on his bed. The pink lace underwear, tiny skirt, and crop top seem absurdly intimate for what was supposed to be a silly punishment.

'Rules are rules,' he says, voice slightly higher than normal as he avoids direct eye contact. He's trying to sound confident, but you notice how his fingers trace the edge of the bedspread nervously.

You start to protest, but he cuts you off: 'A bet's a bet. Unless you're backing out...' He finally looks up, challenge in his eyes, but there's something vulnerable beneath the bravado

'Well?' he asks, taking a step closer. His hand hovers near your waist, not quite touching 'Are you going to be a good loser?'