29, 30, 31, 32, 33, 34, 35.
Missy’s bottom was now bright pink and, I’m sure, tender to the touch. That was just fine. Four days when she was at the outdoor market she had seriously disobeyed our agreed upon rules. She’d purchased pastries, over stayed her allotted time by 35 minutes (hence the 35 spankings), and bought three bags worth of products which is very difficult for her to comfortably carry home. I’d purposely waited until today, her next assigned trip to the market, before administering her punishment. She hadn’t been allowed to wear panties since her return, not so much as punishment, but for my pleasure and her humiliation. She always dripped wetness when I forced her to do something which embarrassed her. She both hated and loved being humiliated and I was pleased to provide this. I looked down at her pink ass and felt myself harden. Her hands were clasped behind her back and even though I could hear her snuffling, she hadn’t moved. She was far to well trained for that. She’s probably thinking she’s finished with her punishment, but she’s wrong. I have something special planned. I reached for the lube and touched her anus. She jumped and whimpered. This was perhaps her worst humiliation. I worked the lube inside of her, using my fingers to stretch her.
“You’re going to remember the rules,” I said softly. During a punishment, Missy isn’t allowed to speak unless it’s to say her safe word.
I pressed the tip of a wide anal plug against her loosened hole and pushed slowly, allowing her body to accommodate the width. Her panting became faster and again, I heard her muffled sob. It was hard to ignore my cock pressing painfully against the zippers of my jeans, but ignore it I would. At least for a few more minutes. Finally, the plug settled into place. Yes, she’d be uncomfortable, but that was fine by me. By the time she got home – on time I’d bet – she’d be dripping and begging me to fuck her.
“I know you worry about the plug coming out when you are in public, so I’ve gotten you a little gift. Stand up while I put this on you. Her eyes widened when she saw the chastity bet. I grinned. “This will serve several purposes, Missy. First, it will keep that plug right where it should be. Second, it will remind you that you’re mine. Third, and most importantly, it will keep you safe. Now, get on your knees and take care of me before you go.”
She looked up at me with wide, astonished eyes, wiped away a tear, and did as she was told. Still, she didn’t speak, for which I was mildly disappointed. I would have LOVED to have punished her for that! With her hot mouth on my engorged cock, it took no more that two minutes for me to come in her mouth. I helped her to her feet, slid her dress over her body, and gave her a not so gentle pat on her bottom.
“Follow the rules, Missy, and if you’re good, I’ll take off your belt tonight. But know this, my love, you will be wearing that belt and keeping that plug in for the next few hours. You should also know that this is your new Marketing Plug. Until I decide otherwise, you’ll wear this each and every time you go to Market. You may speak.”
“I hate this, Sir. I really do,” she said quietly then raised her eyes to me, her cheeks painted with a pink blush.”But you’re right. I need this reminder and deserve this punishment. Thank you, Sir.”