All Day Detention

Tom awoke sore, skin raw. A portion of the face cloth material stuck to his chest and face where her secretion had soaked through and dried. Pulling his face away, slight tearing noise, he muttered to quietly himself, “Rode hard and put away wet.” He paused and chuckled to himself before peeling himself free. He touched his lower lip with his fingers before testing it with his tongue. Opening and closing his mouth, his jaw ached and the muscles beneath his sensitive skin screamed agony. Looking out through the clear plastic wall of his prison, he guessed he was in her bedroom, red digital numbers, slightly distorted through the plastic telling him it was still only 3:27 am.

He chuckled nervously to himself. Dragging him into that other room and fucking him the way she did in front of all those fairy figures. Weird. Did she fancy herself their queen? He didn’t know. She was bonkers, like Annie Wilkes loopy.

Reaching up, he attempted to run fingers though his hair, though couldn’t because it was matted and clumped. He couldn’t believe she just put him in the container all gross like that. At least there was no hairbrush he consoled himself. Yet. He paused, mind churning. She would probably tie him to a fairy wand or something.

He wondered how pissed Tess would be, didn’t matter, even if she was in a killing mood, he sure wished it was her face next he saw when the container was opened, but he knew that was a pipe dream. Miss Addison seemed to have all the angles covered and after her handling of him the night before, he dreaded to think of what other things she might have planned to come.

He watched the minutes bleed away.

She roused before the alarm sounded, clicking on her bedside lamp and sitting up, arms outstretched overhead. Getting out of bed, she turned and made it before vanishing and taking a shower. Returning to the bedroom, she dressed while he watched. When finally she came to the container, she pried the lid off and looked in. “You are in deplorable condition this morning Thomas,” she said, shaking her head, frowning.

He remained quiet and did his best not to glower. Carrying him to the bathroom, she scrubbed him down again, using a fingernail brush, the sharp bristles roughly scratching his already hyper sensitive skin. Clenching his aching jaw, he grit his teeth and was determined not to cry out.

Finished scrubbing, she rolled him over in her hand and inspected him. “You will be spending the balance of the day confined in my underpants. Your task today will to be keep me stimulated, a nice constant slow simmering boil. Not too much, you’re far too impulsive and in need of some restraint,” she stated. Setting the brush down, she took him out to the kitchen and placed him on the counter. Taking a box of Cheerios out of the cupboard, she put it on the counter and got some 1% milk out of the refrigerator. Setting the milk beside the cereal, she looked around, spying an empty diet 7up bottle in the sink. Unscrewing the cap off the empty soda bottle, she returned to him, placing a single Cheerio in the cap and adding a little milk before pushing it in front of him.

“Now eat, you will require your strength. This is also a test of endurance,” she instructed.

He ate ravenously, it had been awhile since last he had food.

She frowned, “Don’t gobble down your food, chew,” she stated as she watched on impassively while he devoured his meal.

When he was finished, he swiped an arm across the milk slobbering down his chin and looked up at her.

Hiking her skirt up over her hips, revealing clean white cotton panties, she pulled out the elastic and slipped him inside over her mons, getting him properly situated and orientated, feet down, front against her genitals before releasing the waistband and smoothing down her skirt. Touching the front of her skirt, “You may begin,” she stated, feeling him begin to move around.

A small smile played on her lips, enjoying the thought of standing before a class of Tom’s friends and peers, while he labored to please her, and them oblivious to the fact that the boy all the little girls creamed about was right there, trapped in her panties, lapping away at her juice.

Cleaning up her kitchen, she departed for school, an extra bounce in her step as walked.

Tom could feel her walking, the rubbery flesh around him moving in rhythm with her stride. He found he was able to get his hands into her groove and slowly knead and massage the flesh, her skin getting significantly warmly in response to his actions.

The last thing he wanted to do was make her come, no way did he want to spend the day glued in that mess again. Slow and steady. He wondered at the possibility of trying to escape at the school, but realistically understood the improbability of such and the Pandora’s Box of complications and hazards associated with it. He chuckled to himself, Pandora’s Box. A heck of a name for a vagina.

Aside from his tinkering around in his grandfather’s shop which brought about his condition, it was his pursuit of the idealized Janine that had set him down this path, so achingly beautiful, but so incredibly dangerous.

He felt kind of bad for Tess, weird he thought, thinking about your sister while you’re mashed up against another woman’s Pandora. She would think he ducked out, even though she expressly forbade it. Through it all, she had been there for him, even going along with his hair-brained plan of sneaking him into the party. He felt a little like a heel reflecting back. Was she in Miss Addison class today? Was she sitting out there, worried, while he was stuck here?

He felt a firm pat through the fabric, he must have slacked off as his mind meandered. With renewed effort, he resumed his chore.