She sat next to me in homeroom. She was new to town and did not know anyone. I smiled at her and introduced myself. She smiled back. I suggested that ...e have lunch together and said that I would introduce her to some of my friends. She said that would be fun.We had first period English class together so I sat next to her. Our teacher recognized that she was knew and asked her to introduce herself. She stood and acted shy and explained that her dad had gotten a transfer to a new job in town and. “ Here’s fifteen dollars. I’ll pay you back as soon as possible. Please don’t spank me.”“I accept your fifteen dollars, but I expect you to experience your first spanking right now. I will teach you how to submit to your weekly spankings until you pay me back. Also, I will add an additional spanking for every hour I spend reloading programs and restoring my data. Are you ready for your first spanking?”“This seems ridiculous for a grown man to be spanked for this, but I guess I agree.” I. Kissing the back of my neck, breathing into me."Can you guess what it is babe?" I asked playfully as Greg let out a dark chuckle. He started to slowly pump the plug inside me. I moaned and winced my face, bending down on all fours, sticking my ass up. Greg grabbed the bottle of lube from the bed side table, popped it open and began drizzling lube all up and down my ass, dripped warm lube over both cheeks, letting beads of lube drip down between my ass onto my ass and wet pussy. "Wanna open it?". "Besides, you won't be totally naked. I've fixed you something to put on."She tossed him a small roll of fabric. He opened it out. It looked like a handkerchief with two shoe laces tied to two of the corners. He glanced at her questioningly."I borrowed them off Jason. You can wear it as a pinafore." You're joking, I'm not wearing that!" Suit yourself, go naked instead. Now take your trunks off." Jackieeee!" He implored."Do it."She pursed her lips in amusement as she watched him peel his trunks.