Tyler grinned back and led her to the room. “You wait right here while I go and get costumes. We are going to have fun with this.”
Tammy went into the room and felt the trepidation building, but tried to talk to herself and calm down. She kept reminding herself that Tyler wouldn’t hurt her and that he was going to make this fun. Deep breaths, she told herself. Keep calm.
Tyler was gone only a few minutes when he returned with a school girl’s outfit for her to wear. “Here, put these on and sit at the desk to wait. I’m going to the men’s locker room to change and will be right back.” He handed her the clothes and planted a kiss on her lips. Then he headed out the door and said, “I’m locking this and marking it in use so no one walks in on you. If you need to get out for some reason here’s the code.” He handed her a piece of paper with several numbers on it. He never locked anyone in a room without a way to get out if there was an emergency.
Tammy looked at the clothes he had given her. A white button down the front shirt, and a short plaid skirt. There was a red ribbon neck tie and a pair of white bobbie socks. That was it, no underwear. Now knowing not to make the same mistake she did earlier, she stripped everything she was wearing off and put on only what Tyler had given her. Wanting the look to be complete, she found some red ribbon in the desk drawer and tied her long blonde hair up in pig tails. When she was done, she could easily pass for eighteen. Wishing for a piece of gum, she looked again in the drawer. Wonderful, she thought as she found some, putting three pieces in her mouth she quickly started chewing. She wanted to be a bubble blowing, hair twirling teenager when Tyler walked in. Now if he had the paddle with the holes in it she remembered from school, everything would be perfect.
Snapping her gum and playing wi
th her hair, she tried to look contrite while waiting for Tyler. After a few seconds, she decided defiant would be better than contrite and propped one leg up on the desk, making sure everything was exposed and plastered a wide eyed innocent look on her face. Much better. The best defense was always a good offense and she wanted to catch him off guard.
Tyler checked in quickly with Link and let him know it was cool to lock up, that he and Tammy were going to be staying in one of the suites, telling him what had happened.
Changing into the headmaster’s suit, he practically ran back to his girl. This was going to be a blast. He had wanted to play this fantasy for a long time. He had the perfect paddle and a nice wooden ruler. There was also a pointer that would leave a couple nice stripes on her ass. Punishment time.
Walking into the classroom, he was shocked. Tammy sat at the desk, one leg propped up on it, her pussy spread wide open for his viewing pleasure. This changed the plan a little.
“Ms. Masterson, I see you disobeyed the school rule and chose to not wear underwear again.” Shaking his head as if in disbelief.
Popping her gum and playing with her hair, Tammy answered, “I did. I must have forgotten to put them on this morning, Tyler.” Emphasizing the use of his first name and spreading her leg wider. She was having fun with this.
“Yes, Ms. Masterson, and I see you have broken several more rules. There is no gum chewing on campus, your hair is not regulation and I believe there is a hygiene rule requiring all girls to shave down there.” He said, his voice dripping with disdain, and trying not to laugh. “And you need to address me as Mr. Thomas. Students are not allowed to use any school official’s first name.”
“Well, Tyler, is there anything I can do to get me out of this mess? My family will pay any amount of money. You know they have it.”
“Are you trying to bribe me, Ms. Masterson?”
“I don’t know. Did it work?”
“That’s about enough, young lady.” Taking a paper towel from the principle’s desk he walked over to her, holding it out, “Gum,” he stated firmly.
Tammy defiantly spit her gum into his towel-covered hand and stuck her lower lip out in a pout. She put her leg down and crossed her arms over her chest, playing the hurt school girl part to the hilt.
“Mr. Thomas, what can I do to get out of this? My family will be so upset if I get expelled. Isn’t there something I can do?” She let a tear fall and tried to give him her best little girl look.
“Ms. Masterson, there is a thing or two, but I’m not sure you would be comfortable doing those things.”
“Anything rather than shame my family. Anything,” she answered excitedly.
“You would have to accept punishment.”
“Yes, sir.”
“And I may need something else from you, dear.” He wiggled his eyebrows suggestively.
Not totally faking the anxiety in her voice, she answered, “Sir?”
“Let’s proceed with your punishment, Ms. Masterson, and see what happens from there. I want you to stand and remove all your clothes. You are to fold them neatly and place them on the desk.” He instructed her.
“All my clothes, sir?” she asked with a tremble in her voice.
“Yes, my dear, all of them. Leave your shoes and socks for last and bend over when you remove them.”
“Okay.” Tammy started with the tie slowly pulling it around her neck before folding in and laying it on the desk. Then slowly, one by one, she unbuttoned the shirt. It fell open before she shrugged it from her shoulders. Running her hands over her body, she cupped each breast offering them to him, before moving to her skirt. Shimmying to lower it on her hips, she turned her back to him and bent from the waste to pull it down over her feet, making sure to wiggle her ass in the process. Then she removed the shoes and socks. When she was done she turned to face him and crossed her hands protectively over her body.
“Hands at your sides, Ms. Masterson,” he said, walking around her, inspecting her. He pinched a nipple and pulled it towards him, then reached down to the hair between her legs, shaking his head.
“This must go.”