God, this plug is so fucking heavy.
She shifted in her seat for the 300th time since climbing into the passenger seat. She'd already been wearing it for half an hour and she could only be grateful that he hadn't tasked her to do something like grocery shopping with the plug the plug in...again. But sitting on it for this long wasn't much more comfortable.
"Prissy, be still. You're only making it worse for yourself. Breathe."
Prissy. He loved to call her Prissy. Short for Priscilla but also a reference to the little digs he made at her while they were still getting to know each other. He made fun of her private education, table manners, posture from years of ballet training and yoga practice. He even went so far as to call her princess on their first date and the pet name stuck.
Their relationship shifted into a very special one. With him, she had discovered things about herself she either never knew or had dedicated herself to repressing. Her uptight upbringing stressed propriety at every turn and some of the things she and her Sir got into these days were way south of proper.
Sitting in her seat, her focus turned to the puckering and repuckering of her asshole. She knew the purpose of his training was to improve her tolerance for anal play but the metal one he had gotten her was different than the glass ones she had played with before. Firstly, it was cold as fuck. And secondly, when she walked, she could feel it weighing down on her anus. As a result, there was a fear that was two-fold: that her anal training was going so well that the plug itself would just fall out or she wouldn't be able to handle and would have to beg to take it out. She loved begging for some things but not when it seemed she would fail at a task. Not just because she was ultra competitive, as she had been her whole life, but when Sir asked something of her, she wanted to get it done. She loved hearing him say, "I'm proud of you, princess" so complying with the task was always as much for her as it was for him, if not more.
She pouted, letting her brat peek out and shine a little. He spied her pronounced lower lip and smiled. "You've done such a good job. Just 20 more minutes...maybe 25." He smiled again, enjoying her indulgence.
She added a loud sigh to her pout and crossed her arms across her chest.
He held out his hand for hers. When she surrendered it to him, he lifted her open palm to his lips and planted a soft kiss on it. "Do you require a distraction? Would that help you pass the time?"
Her pout turned in a smile and she nodded. "Yes, please!"
He briefly looked into her eyes and then back to the road. His hand guided hers to his crotch and she anticipated he would instruct her to provide a little road head until they arrived at their destination. Immediately her other hand reached for the presumed objective.
His hand reached out and lightly slapped her other hand away. "No, no, no," he said, wagging a finger in her face, "Listen to instructions first. If you do well, maybe you can enjoy a taste."
The pout returned but she placed her right hand behind her and under her butt, the feeling of the plug becoming pronounced once again.
"What I want you to practice is...unbuckling my belt, undoing my pants, and liberating my cock...but all with your left hand and with your eyes closed."
Priscilla was not left-handed.
"It's going to take some concentration of your part and if you do it quickly enough, and without hurting me, you may receive a treat at the end."
He wasn't joking. She wasn't used to doing things with her left-hand and it was a good 15 minutes of fumbling with the belt buckle and the fasteners on his pants, complicated on their own and not helped by him refusing to move or adjust himself in any way. Once she had gotten to the part of lowering his zipper, he guided her so as not to catch his skin in anyway. She made sure to slide her fingers between the zipper and his crotch to prevent any accidents.
"You are such a good girl, princess. We're about two exits away from where we need to get off and I have one more task for you..."
