Punishment 2058

"Please, please Mistress", she heard him mumble around the gag.

Please she thought, it was always the same begging when it was time to take his punishment but did he listen when she asked something of him? No.

This session was a lesson, there was a time and place to push boundaries and test rules but he'd been taking the liberty of not testing her rules but flat out ignoring them and that just wouldn't do. She turned to look at him watching the machine slowly fuck his hole as she did.

"Please? Tell me pet, why do you defy me?" She knew the gag prevented him from answering but the question hung in the air as a reminder of why they were there, of why he was being denied.

Walking over to him she trailed her fingertips across his ribs watching her nails score small red marks across his skin as she did before moving to stand in front of him. Leaning forward she bent down to remove the gag, she watched him flex his mouth as it popped free from his lips before he settled, keeping his lips slightly parted.

"Please Mistress", he looked at her expectantly as he begged. He knew how she loved hearing him beg but he had become too accustomed to topping from the bottom.

"There's that word again, please, you repeat it as if it matters. Tell me pet, who do you owe your pleasure to? Who do you have to thank for filling your hole right now?" She said.

She'd never pushed him, never reminded him of their power play during a session before. She hadn't thought she'd needed to before but clearly they had both been making assumptions about the terms of their relationship and it was time to remedy that.

"Mistress?" He replied. Not a statement but a question, confusion apparent on his face as he looked at her unsure of where this was leading.

Turning, she walked to the machine's dial and turned up the momentum forcing the machine to fuck him faster before turning back to face him. He moaned, closing his eyes momentarily lost in pleasure. Turning away she privately smirked to herself as she reached for the strap and wand before returning to his side.

"Look at me," she commanded. Turning her palms to face him she showed him what she'd just retrieved.

"I alone give you the pleasure you feel in this room. You seem to have forgotten that fact. Pleasure or punishment, your actions outside of this room have real consequences here," she said.

She felt his eyes track her as she placed the wand tip to the head of his erection and strapped it into place, securing it before turning it on. His cock bobbing as the sudden burst of sensation ran across his skin.

Moving to his head she grabbed him by the jaw turning his face to hers, his eyes bright, mouth lax with pleasure.

"You will not cum without my permission," she said.

He just stared at her.

She smacked him across the chest.

"Do you understand me?," she prompted.

Sucking in a breath, his eyes darted to hers. She'd never struck him before. "Yes, Mistress." he replied.

"Good. If you disobey me that slap will be the least of your worries," she said.

Moving to the nearby couch she watched him. He was beautiful, bound, hard and filled with pleasure. She watched as his breathing increased and his cock dripped with need.

She wanted to go to him, to end this punishment before it really began instead she forced herself to sit there and watch him knowing it was about to end. When she saw his eyes squeeze shut and his back start to arch she got up and went to him, shutting off the wand and reducing the fuck machines speed to a punishingly slow but consistent rate. She clasp her hand around his shaft and slide her thumb through his precum circling it across the head of his cock as she did before releasing him.

She turned her eyes to his face as she said, "Ask pet, Ask your Mistress for more."

He looked up at her with doleful eyes. "Please Mistress," he said, "I need more."

She briefly turned and switched the wand back on letting the intense vibration shoot through him. She watched as his whole body jerked and heard him moan before flipping it back off.

"I didn't ask you what you needed", she said. "Do you think your Mistress doesn't already know your needs and how to tend to them? I told you to ask me for this pleasure." She playfully but firmly smacked him across his right peck.

He stayed silent. She wasn't sure if it was unwillingness that stopped him from asking or if he hesitated because this was a new layer of play for them. She waited a beat longer for his reply before switching the wand back on and increasing the speed of the machine fucking his hole.

"Fuck! Oh God," he bit out. "Please don't stop, please," he continued.

She silently counted to herself, a minute later she turned off the wand and stopped the fucking machine leaving the thick shaft in his ass as she did.

"Do you have something you want to say to your Mistress?" She prompted.

She watched his resolve crumple as he turned his head to face her and said, "Please Mistress, fuck me more. Please, let me cum."

She removed the strap and wand from his cock, discarding them to the side and closed her hand around him, pumping her first up and down his shaft twice before bending down to take him in her mouth. She took him deep working her throat around him as she enjoyed the weight of his cock across her tongue.

Releasing him from her mouth she placed a kiss across his chest between his pecs.

"Thank you Mistress," he said.

Surprised, she looked up at him and smiled. She felt his eyes on her as she walked to the front of the machine and loosened it, removing the cold shaft from his ass. Reaching for the nearby lube she spread it across her right palm and fingers. The machine had kept him open for her, she slid her four fingers in smoothing them across his prostate. In a short pattern she slowly worked her hand, inching it in a little at a time until the base of her thumb was against his ass. A steady stream of precum dripped from the tip of his cock, she loved milking him.

He'd never thanked her for anything before, not before, during or after. Hearing him thank her had pushed her to want to give him more, to push his limits and give him something new.

She withdrew her hand completely and applied more lube this time making sure to cover her hand up and over her wrist. With her other hand she stroked his cock as she started to slide her fist into his tight hole. She'd been working on stretching him but they'd only taken it this far once before and never to completion. She continued to work her fist into his hungry ass, slowly filling and fucking his tight hole as she did.

When he'd taken all of her she looked at him and said, "You have my permission to cum my pet."

And then she fucked him fast, fisting him and stretching his hole.

His legs tightened in their straps, his back arched as he spiraled closer to his release lost in need.

"Fuck," he moaned. "More, fuck me more, stretch me," he quietly begged.

She let herself go and fisted him hard and fast.

"Oh God!," he cried out as his cock jerked, shooting his hot cum onto his belly minutes later.

She removed her fist and wiped her hands before grabbing a towel and cleaning him up. As she walked around him removing the straps from his wrists and legs she said, "You should thank me more often my pet, we can have more fun like this when you please me."