Master Garret Ch. 04

Garret's hand left him then almost immediately returned, massaging in a cool substance with his finger. The coolness caused Jonathan to twitch, but it soon warmed. He recognized the slickness as lube. That helped him relax further. Garret's massaging finger began to feel good, and Jonathan found himself pushing back unconsciously. Garret chuckled and took a firm hold on one ass cheek to keep his submissive still. He added more lube to his finger, then slowly pushed in.

Jonathan gasped and made to move away but Garret held him firm. Garret stopped when he had just the first knuckle in.

"Relax," he murmured. "Just breathe and relax, trust me."

Jonathan took a deep breath and made himself relax, muscle by muscle. Garret's finger inside him didn't hurt it just...felt strange.

As soon as Garret felt Jonathan relax, he slid his finger in to the second knuckle. Jonathan instantly clenched around him and softly moaned. Garret's other hand soothingly caressed Jonathan's back as he let his submissive get used to this new intrusion, then once again pushed in to the last knuckle.

Jonathan trembled at the new sensations. It felt...good yet so very strange and wrong all together. Then Garret started to move, and Jonathan turned into a whimpering mess. Every nerve seemed hyper sensitive, a live wire coursing through him. Garret kept a steady, slow pace, drawing his finger out to the very tip before pushing all the way back in. Once Jonathan's soft little whimpers changed to deep moans, he withdrew and added more lube, then began pushing in a second finger.

Jonathan clenched his hands into fists and let out a long, drawn out moan as Garret eased two fingers inside him. It felt so big to Jonathan, hitting even more overly sensitive nerves. Garret just continued the same, slow, in and out motion. Not seeming to be listening to Jonathan. Then his hand was gone again. Jonathan breathed in deep and relaxed at this respite, until he felt something cold pressing into him.

He had forgotten about the butt plug.

The tapered bulb was a little wider than Garret's fingers, and Jonathan felt every inch of it as it slid in. He twitched as Garret pushed it all the way in and his hole closed around the smaller base, flared to keep the plug in place. He jumped when Garret tapped the flared end, the sensation reverberating through his rear.

"I don't think you'll be able to forget that's there anytime soon," Garret whispered to him. "I wonder how long before it drives you crazy, you are so very sensitive there."

Jonathan moaned as Garret wiggled the plug, his own hips wriggling in response. He gasped as he suddenly felt Garret's weight on top of him, draped over his back, spooning his hips. With his hands on either side of Jonathan's shoulders, Garret leaned close to his ear.

"You will not be cumming today, not even if you beg oh so prettily. If you find yourself getting close you will tell me immediately or your punishment will be twice as worse and go on even longer. Is that clear?" He flexed his hips against Jonathan, causing Jonathan to moan as he felt his Dominant's hard length push against the plug.

"Yeeees," he groaned out through clenched teeth.

Garret seized him by the hair and pulled him back so he was pressed tight against him.

"Yes, what, pet?" Garret growled.

"Yes, Sir!"

Garret released him and stood, walking over to a table where he had laid out a few things.

"Stand and come here."

Jonathan shakily pushed up to his feet and faltered when he felt the plug shift. He drew in a deep breath and walked the few steps to the table, his focus on the sensations caused by the plug. The items on the table brought him back to the present, laid out carefully for him to view.

Lined up in a neat row from left to right lay; a leather paddle, a wooden paddle with holes, a black leather belt, a flogger, a crop, and a thin cane.

"This will be the painful part of your punishment," Garret said seriously. "Choose which one you want me to use on you, and I will choose one as well. Choose based on the severity of your own punishment, what do you think you deserve to be spanked with?"

Jonathan looked sharply at Garret, then back to the instruments on the table. How badly did he deserve to be punished?

'Pretty bad,' he thought to himself. 'I fucked up big time.'

The cane was his first thought. He knew how much pain that could bring and it fit with how badly he had messed up. But it also scared him. Same with the belt, it would cause some thick, slightly raised marks on him, but it scared him too. If he was honest with himself, all of these instruments scared him to some degree. He would much rather have Garret just use his hand for his first ever spanking.

He half admired Garret for this method of punishment, making him pick his own torture. It was brilliant and really got into his own head. The other half was whimpering.

With a deep breath, he made his decision and placed his hand on the cane.

Garret paused for a second before picking it up. Jonathan's choice had surprised him. He also picked up the small leather covered paddle. With the cane he indicated a raised bench. The bench was generously padded, leather, at a slight angle and was in two levels. Jonathan had seen it in use before. The big part of the bench, the center, was to be laid on, and the thinner lower level of the bench were to be knelt on elbows and knees. Cuffs were attached to the side to secure thighs and biceps, and more cuffs attached to the lower level of the bench for ankles and wrists. More straps were attached to the center to keep squirming submissives still to take their punishments.

Jonathan had never been secured to a bondage horse before, and looking at it made him shiver. He climbed onto it, not exactly sure what to do, but he rested his torso onto the center and knelt on hands and knees. The center held his body weight, the lower level of the bench just there to support his arms and legs, and he was grateful he wouldn't have to hold himself up for what was to come.

Garret started to bind him. He moved Jonathan's legs into the proper spot and and secured his thighs with the straps. Jonathan turned his head to the side and rested his cheek against the cool leather as he watched his Dom work. Surprisingly, Garret didn't secure any of the center straps, though Jonathan was absolutely unable to go anywhere as he was currently bound.

"Head up," Garret commanded as he moved to stand at the head of the bondage horse.

Jonathan did as he was told and his gaze zeroed in on the ball gag Garret dangled from his fingers. Garret took the straps firmly in hand and brought the gag closer to Jonathan. Without being asked, Jonathan obediently opened his mouth and let his Dominant put the gag in place. He felt the ball settle in behind his teeth and he worked his mouth around it to get used to the feel as Garret buckled the straps behind his head.

Garret looked down at his bound submissive and felt a mixture of pride and...almost pity. Jonathan had obeyed without protest or hesitation, and looked up at him with trust in those beautiful blue eyes. Garret gently stroked his hair and down his cheek. He pressed a small bell into Jonathan's hand.

"That's your safeword now," he whispered. "Drop it the moment you feel it's too much, I'll hear it fall." He held up the cane. "Six with this, three on each side." He set that down then held up the paddle. "Twenty-four with this. That's thirty all together, and you'll be feeling that thirty for a few days to come." He picked up the cane again and looked intently into Jonathan's eyes. "Are you ready?"

Jonathan nodded once, then lowered his head to rest on the bench, his hand tightening around the little bell.

Garret stood behind Jonathan, holding the cane in both hands, calculating. He didn't want to cause long lasting welts. The paddle would tap the small welts he caused each of the twenty-four times it came down, that would do. Without warning he expertly flicked the cane and it snapped against Jonathan's left cheek.

Jonathan's whole body tensed against the restraints and he groaned against the gag. The blow had stung far more than he had expected. Before he had time to recover he felt the sharp sting on his other cheek. He couldn't help but pull against the bindings. The other four came in quick succession. Two to each side, each sting landing in a different spot than the ones before. He clenched his teeth against the gag and let out a muffled cry, tears threatening at his eyes. Then Garret's hands were there, soothing the sting they had just caused.

"Just twenty-four to go," he murmured as he stepped back and brandished the leather paddle.

The impact of the paddle was less sharp, but still left a sting. Its bite heavier than the one from the cane. Jonathan counted each stroke in his head. His body wound so tight and tense, he couldn't help the cries that escaped from his forced open mouth. The impacts shifted the plug in his ass each time and that added arousal to the pain, but the pain was greater. At halfway through the sting began to burn. He imagined his ass had turned a fiery, angry red, and he wouldn't be able to sit right for a week. The tears at his eyes fell, and for a moment he contemplated dropping the bell. That's all he had to do, just drop the bell. Garret would set the paddle down and free him, it would all be over.

No.

Only six more to go.

He had seen worse punishments than this, had admired those submissives for their strength and enduring the pain.

No.

Four.

He could do this, he could take it.

Two.

Fuck, it hurt.

Zero.

Garret immediately set to releasing Jonathan from straps and cuffs. Jonathan simply lay there, exhausted and stinging. He unconsciously let the bell fall as Garret removed the gag.

Garret's arms were under his chest, lifting him away from the bondage horse. He was gathered into the man's arms and held close. He hissed as his raw bottom brushed against fabric when Garret eased him down onto a bed of soft cushions.

"Sir," Jonathan said hoarsely, his throat dry. One of his hands gripped Garret's shirt as he was tightly held. "Sir, I'm sorry."

"I know, Jonathan," Garret murmured and stroked his submissive's hair. "I know, lad. All is forgiven. Just relax now."

Garret gave him water and gently massaged a blissfully cold, soothing cream into his burning backside. The coolness and whatever was in the lotion helped ease the stinging pain.

"I don't know what happened, Sir, I...I just got so carried away. I didn't mean to drink so much it just...it just happened."

Garret just held Jonathan and soothingly stroked his back as he listened to the apology.

"I won't go out to the bars again."

"No," Garret finally spoke. "No you just need to learn some self control. I will help with that, I trust that this will not happen again."

"What if it does?" Jonathan asked softly.

Garret looked down at the submissive clutching at him in his arms.

"Then I'll add four more with the cane, and another ten with the paddle," he said seriously. "I'll keep you twice as long in the rope, and edge you the entire time you're suspended." He fixed a level look at Jonathan. "Is it going to happen again?"

Jonathan swallowed the lump in his throat.

"I will try my best, Sir," he said quietly.

Garret nodded, "That's all I ask." He tapped the end of the plug still lodged firmly within Jonathan, grinning when his submissive stiffened and moaned on his lap.

"Now, your punishment is done, you are forgiven, but this stays in until I take it out. You won't be cumming for at least a week, and I will play with that ass of yours every day."

Jonathan groaned and buried his face against Garret's chest.

"Yes, Sir," he said, almost forlornly. "But, Sir?"

"Yes, pet?"

"You lied."

Garret raised a very surprised eyebrow, "How so?"

"You promised me that I would not enjoy today. Well...I did enjoy some of it."

Garret threw back his head, and laughed.