Lost Bet (GenderPlay Quicky) Crossdressing Story (Patreon)

Jimmy stands anxiously in Hope’s room. Having lost the bet, his fate for the evening is sealed.

“This is going to be so much fun,” Hope giggles, stepping over piles of her clothing left on the floor. “Any idea what you want to wear?”

“I dunno,” Jimmy replies, feeling like a lost sheep. “My own clothes would be preferable”

“No way!” Hope answers with a cheeky grin. “You lost the best and that means you’re mine to dress up for the party. I’m thinking heels and one of my short dresses.”

“Hope, please…,” Jimmy pleas, watching her pull out several pairs of stilettos “Be nice—nothing too girly.”

“Nothing too girly he says…!” Hope teases, picking up a bright red dress from the floor. “What about this one?”

Hope holds the thin red dress against Jimmy’s body and looks him up and down. “Do you think you’d fit into this?”

“Erm…,” Jimmy mumbles, unsure how to answer.

“Nah,” Hope says, tossing the dress to the floor. “We need something that will make your hips look wider than your shoulders.”

Jimmy rolls his eyes and Hope begins digging around again for clothes.

“Yes!” she calls out triumphantly, holding up a pale puffy tulle skirt. “This is perfect!”

“That...?” Jimmy questions dismissively. “Looks like something a ballerina would wear.”

Hope stops and puts a hand on her hip. “Shame I don’t have a ballerina’s outfit. That would have been perfect!”

Holding out the skirt for Jimmy to hold, she starts looking for more.

“I have the perfect top to go with that!” she cheers.

Seconds later she lifts the top into the air like she’s won a trophy “This one is perfect for you! It’s going to look so cute!”

Jimmy looks at the sparkly top and frowns.

“Turn the frown upside down!” Hope teases, holding the top up to Jimmy’s chest.

“Try being in my position…,” Jimmy replies, folding his arms to stop her from holding the top to his chest. “Would you be excited about this if you were me?”

“Err yes!” Hope answers sarcastically. “I’d be thrilled about wearing such a cute outfit and showing off my sexy little body.”

“Are you saying I’m sexy?” Jimmy asks, not knowing if he should or happy or sad.

Hope tilts her head and then looks past Jimmy to her private bathroom. “Just get in there and shave all your hair off, will you.”

Knowing he wouldn’t hear the end of it, Jimmy does exactly that. Hoping into Hope’s shower, he’s handed lotions and a razor, and he gets to work

Exiting the shower, Jimmy pats himself dry and notices some female underwear on the countertop.

“Hope,” He calls out, picking up the lacey white push-up bra. “Are you wanting me to wear this bra?”

“Yes,” Hope answers back through the closed door. “Hurry up, I’ve still gotta do your makeup!”

Awkwardly sliding up the matching briefs, Jimmy attempts to put on the bra. Struggling, he eventually gets it hooked up.

“Jimmy,” Hope whines! “Hurry up!”

Now standing in Hope’s bathroom in just her underwear, Jimmy is afraid to come out. “I don’t want you to see me in your underwear!”

Jimmy hears movement from outside and before he knows it, Hope has thrown open the door and is staring directly at him.

Hopes face lights up. “Aww…,” she teases, passing him the puffy tulle skirt. “Aren’t you cute!”

“Yeah yeah…,” Jimmy mutters, snatching the skirt.

As Jimmy gladly hides his shame by stepping into the skirt, Hope passes him the sparkly top. Helping him into it, Hope adjusts the fit and is pleased with her outfit selection.

Feeling like a fool as he feels wafts of cold air against his bare legs, Hope sits him down and places a long black wig on his head.

“Sit still,” Hope commands.

Like a woman on a mission, Hope brushes out the wig and styles it. Before Jimmy can even react, Hope is slapping makeup on his face at lightning speed.

Finishing with lipstick, Hope steps back and smiles.

“Best I can do with the time!” she admits, closing the lipstick.

Jimmy is stunned as he looks at his reflection in the mirror. He barely recognizes it has him.

“Best you can do?” Jimmy asks sarcastically. “I don’t see me in the mirror anymore Hope! I see a girl.

“Flattery won’t get you out of this one,” Hope laughs, now applying her own makeup.

Standing up from Hope’s vanity mirror, Jimmy sees the pale high heels Hope has picked out for him. He picks them up and shakes his head. “No way am I going to be able to walk in these.”

Hope stops doing her mascara and looks around. “Yes, yes you are.”

Rolling his eyes, Jimmy tucks his now long black hair behind his ears and sets the heels down in front of him. Stepping one foot in and then the other, he stands taller but much less stable.

“Wow,” he complains. “These don’t half pinch.”

“Yeah sorry,” Hope replies, doing her lipstick. “Was the closest I had to your size.”

Taking a single step, Jimmy looks at himself in the mirror. The girl he sees glaring back at him is slender, pretty, and charming. He can’t believe it’s him!

“This is humiliating!” he groans, fighting with his long hair. “How was I supposed to know you play basketball so well? You cheated me!”

Hope grins as she brushes out her hair. “Teach you to underestimate a girl again…won’t it!”

“Yeah…,” Jimmy sighs. “Learning my lesson now…aren’t I?”

“Yup!” Hope laughs, joining him at the mirror. “Still, you do make one cute little Hunny.”

“I tell you what,” Hope grins mischievously. “How about double or nothing? I dare you that I can get a straight man to kiss you tonight.”

“What if you can’t,” Jimmy asks, getting worried about what she has planned.

“Then I will shave my head,” Hope is quick to answer.

“Ain’t no man going to kiss this,” Jimmy laughs showing himself to her. “You’re on!”