“Well, Anthony, it seems like you're in this office almost every day to get punished for talking in class or some other silly offense. I don't know what's the matter.
"You're just a little busybody, a real talker. Isn't that so?”
“Yes, sir.”
“Well, since you act like a little girl, maybe I should dress you like one?”
“Please, sir. Oh, no. Please, no!”
  “It seems like we've struck a sensitive cord with you, my little talky-talky boy.”
“Please, Mr. Hillman. I'll be good. I really will. I'll never talk in class again. I promise.”
  "No, I think a little panty punishment is just the thing.”
“Not that, sir. Please, sir. No.”
Anthony tried to continue protesting, but Mr. Hillman held his hand up and made a motion to be quiet. Then, he pointed to the bottom drawer of his desk.
“Open the drawer, Anthony, and tell me what you find in there.”
He pulled open the drawer and stared into it through his tear-blurred vision.
“Well, Anthony. What are they?”
“They're ah, girls, girls' things, sir.”
“Girls' what? You know what those are, boy. Now, tell me what are they?”
“Sir, ah, they're girls', ah, p-panties, sir.”
“And they're pretty ones aren't they, Anthony?”
“Sir. Yes, sir.”
“Now, pick them up.”
The boy reached into the drawer and slowly pulled out the pair of pink panties that were right on top. They had a huge frill of dark pink lace around each leg elastic and a big white lace rosette on the left hip.
At this point, the probing, humiliating questions became too much for him, and he started to cry.
“Don't worry, Anthony. It's okay if you like silky panties and other girls' things. I understand some boys just can't help it. They just love all the pretty clothes only little girls get to wear.”
He reached forward and tugged down Anthony's shorts and underwear as he continued talking, “Now, let's take these down so you can step into your new panties.”
“Please, sir. I . . .”
“Anthony, get into those pretty panties right now, or I'll give you another caning, and it will be the hardest caning I've ever given to you.”
His ass still stung from the caning he had received just minutes before, he was sure he couldn't stand another assault to his pain-scorched bottom.
Anthony held open the soft, smooth, silken pink panties — took a deep breath and then slowly stepped into them.
He started to pull them up his legs, but he didn't do it fast enough for the impatient Mr. Hillman, who pushed the boy's hands away and himself teasingly drew the lace panties up the kid's scrawny legs until they were high around the boy's slender waist. He stroked the soft fabric over the kid's large hips and ass. He boldly adjusted the boy's private parts until he was satisfied with how they were cupped in the neatly stretchy nylon. All of the intimate handling caused the boy's cock to surge to life in the soft nylon. Mr. Hillman smiled.
"Getting a boner in our girlie panties, are we?
"My God, what a pantywaist you are.
"Seems like you are really enjoying this, boy! — Or should I say 'girl!'"
Mr. Hillman put the boy over his lap and positioned him so his big pink pantied butt arched high in the air directly in front of his lecherous gaze.
The old man picked up his cane.
"I think I should do your father a favor and work on curing you of this attraction you have for girls' panties. He must be embarrassed to have such a sissyboy for a son.
"A hard-on, really! What would your father say?"
Crack!
"O-o-o-o-o-o! Please, sir. Don't tell him!"
"But you're a sissy, aren't you?"
"Uh-uh, yeah, . . . yes, sir!"
"Good. Glad you admit it."
Crack!
"Ah-h-h-h-h-!"
"Anthony! Your cock is still very hard. I can feel it in my lap! Well, I better tell him. I mean, then I'd just be doing my job. Right?"
"Ye-e-e-eah-th, th-th-sir!"
"You're still quite hard. I can feel it throbbing. I better stop before you make a mess in your sweet little panties . . . and all over me. Pull yourself together and go!
"Leave the panties on! If you take them off, I'll really give you a lesson in sissy clothes. Stay dressed as you are. I'll check on you later.”