Yes

Tom watched on, feeling slightly disappointed but not surprised that Miss Shelley was not going for it. Then he felt the bet energy surge.

“So, who won the bet Dennis?” asked Miss Shelley. Tom suddenly felt hope, the bet energy buzzing, and he understood. Miss Shelley is bound to the bet as teachers are responsible for their students.

Dennis eyes flicked to Tom, and Miss Shelley’s gaze followed. “ah so you are the lucky one Tom. Alright Dennis leave I will have a word with Tom.”

Dennis flees the classroom, as he does Tom can see the rest of his friends hovering at the door.

Lisa goes to leave as well, “Lisa, you should stay.” States Tom “Can you close the door, so no one can overhear, Thanks”

Lisa walks and shuts the door before turning back to watch Tom and Miss Shelley.

“Ok Tom, You have 5 minutes, what would you like me to wear”

Tom looks Miss Shelley up and down. As she sees Tom observe her, she feels naked and starts shuffling her feet.

“Miss Shelley, I got a few ideas in mind. I would like to run a few tests to check my ideas” Miss Shelley nods her head in acceptance.

Tom reaches forward and grabs the hem of her shirt. “This shirt looks nice, but I don’t think it is the right style.” He runs his hands along the hem, his thumbs on the outside with the back of his hand sliding up into her shirt rubbing a long her stomach.

“Jill what do you think about Miss Shelley in a shirt that only went to this length” asked Tom as he slowly slides her shirt up to display her belly button. Tom doesn’t wait for an answer. “or how about this length”

Tom continues to raise Miss Shelley’s shirt to just below her breasts. The back of his hands sliding up onto the cup of her bra. Jill walks over from the door to stand next to Tom watching him slowly undress their teacher.

Tom then pulls the hem of the shirt out and lifts it over the cups of Miss Shelley’s breasts and takes his hands away. Leaving Miss Shelley standing there with her shirt bunched across the top of her chest fully displaying her bra clad tits.

“I like this look, how about you Jill?”

Surprisingly Jill agrees “I do like it, but I don’t think the headmaster will allow it.”

“I know, this look could be improved a little as well” Tom then reaches forward and slides a hand into one of Miss Shelley’s bra cups, he firmly grabs and lifts her tit, while the other hand reaches forward to pull the cup down. He does the same to the other breast. Miss Shelley is now standing there with her tits exposed framed by her bunched up shirt and her pulled down bra.

“This look is perfect.” Tom then pulls out his phone and hands it to Jill. “Could you take some pictures, it will allow he to decide. She can’t dress like this all day but maybe this could be the look during lunch tomorrow”

“Now the skirt.” Tom walks around behind Miss Shelley and starts to feel her arse. “I feel the skirt should be tighter.”

After a minute he grabs the material at her thighs and raises it up to her hips “what about the length?”

He continues to raise the skirt and pause when the hem is above her knees, Then raises it to mid thigh, then he raises it just below the bottom of her arse. “I like this length” Then he raise the skirt to fully around her waist to expose her panties. “This is better, but again I don’t think the headmaster will like it.”

He turns her around so her back is facing Jill and the camera and runs his hands over Miss Shelley’s arse. “I Don’t like these panties to much” He grabs the edges and pulls them into the crack of her arse, then runs his hands over her exposed bum.

“Miss Shelley definitely needs to wear a thong tomorrow”

Knowing time is running out Tom steps back to take a good look at Miss Shelley. He cant believe she just stood there and let him mess with her clothes.

“Thanks Miss Shelley, I think I know what you should wear tomorrow. You can fix your clothes now.”

Miss Shelley fixes her panties and skirt and goes to fix her bra. “Hold a sec, one final thing I want to check” Tom reaches forwards and tweaks her nipples to make them hard, before he pulls her shirt down over her tits. He then rubs the pokies through her shirt “Yes this is a good look on you Miss Shelley”

Miss Shelley looks down at her chest and slightly nods before seeing that Tom was done, reaches under her shirt to fix her breasts back into her bra.

“Alright Miss Shelley, Here is my phone number. When you get home, Please text me pics of you modelling a couple of different sets of sexy underwear. I also need a couple of pics of you in different skirts that finish above the knee. And lastly some pictures of different blouse’s that button up.”

“Alright Tom, you better run along now, Lunch is half over.”