Bobby's Big Brea

Bobby waited uncertainly on his knees for Mistress to return, the dull pain on his ass niggling at him. He had not been told to follow her, so he reasoned she wanted him to say where he was. But what if she didn't? What if she expected him to follow her? Plagued with doubt, he bit his bottom lip resolved not to do anything until she specifically told him to. His wait was rewarded when five minutes later she returned with a glass of water which she handed to him.

'Drink this, and then put it down on the table there,' she said, pointing at the coffee table.

'Thank you Mistress,' he said and eagerly drank. The cool water was wonderfully refreshing. He hadn't realised how much the flogging had taken out of him, and now realised he was covered in a layer of sweat. As he drank, Mistress reached out with a finger and trailed it along his sweaty stomach, causing Bobby to almost choke. He watched as she admired the drop of sweat she had collected on her fingertip, holding it up to the light and curving her finger one way and then the other to better see it. She then closed her eyes and lowered her finger into her waiting mouth, sucking the sweat from her beautiful long pointer. Bobby groaned and clenched his glass tightly as he gazed at the finger being sucked in and out by her perfect mouth. Mistress removed her finger and her eyes came open in a flash, instantly zeroing in on him and fixing him with an accusatory glare.

'What was that?' she demanded.

Bobby hastily put the glass on a coaster on the coffee table, lowered his gaze and clasped his hands behind him.

'I groaned Mistress, ' he said in a soft voice. 'I couldn't help it. I'm sorry Mistress.'

He expected a sharp retort, or further punishment, but Mistress seemed in a forgiving mood. Or perhaps she was simply keeping score to be dealt with at a later time. Whatever the case, Bobby found himself gratefully merely to be standing in her presence once more.

She slipped out of his peripheral vision and he wondered with a start if he had missed an instruction, or if a punishment was about to begin again. The anticipation left him feeling jittery, and he felt a bead of sweat drip into his left eye. He wished he could wipe it away, but did not dare to move. There was still every possibility that Mistress would send him away, and he would not do anything to further jeopardize his chances of being permitted to stay.

He heard the rustling of fabric as it was cast to the floor and struggled as he fought his natural instinct to look up.

'Finally,' Mistress said after a few minutes, during which Bobby had successfully refrained from looking at her. 'It appears you are learning some discipline already. Maybe there is some hope for after all. Now, you may look.'

'Thank you Mistress,' he said with a gasp, and quickly raised his eyes to gaze upon whatever she had permitted him to see of her.

She stood in the doorway, the long red satin robe finally cast from her body to reveal a heavenly sight. Bobby's eyes were drawn instantly to her barely covered breasts, before sweeping quickly over the rest of her body, hardly knowing were to look first.

Mistress had chosen a naughty executive look which combined authority and sensuality. The short black jacket with a matching skirt would not have looked out of place on a high-powered business woman, if not for several factors. She was wearing no shirt underneath the jacket, which buttoned underneath her breasts. This in itself would ordinarily not be too revealing, however Mistress's jacket was at least two sizes too small to accommodate her D-cup breasts, causing all but the nipples to pop out from the confines of the taut material. Her soft creamy white breasts were beautifully contrasted by the jet black firm material of the jacket. The black skirt finished halfway to her knees and had splits running all the way up on both sides.

Bobby gazed at her long slender legs, her full luscious breasts and slim waist, and found himself begging for more. He longed to be able to free her breasts from the tight confines of the jacket, to run his hands up the splits of her skirt to discover if she was wearing anything underneath it. Mistress turned slowly, giving him a look at her perfectly rounded ass, before quickly bending over to reveal a pair of black thong panties hiding beneath the skirt. Before he could do much more than register this however, Mistress straightened up and turned to face him, the skirt falling back down her thighs.

'See what good boys get when they behave,' she whispered.

'Yes Mistress,' Bobby whispered back, vowing to be a very good boy.

'Come,' she called as she turned her back on him and exited the room.

Bobby's cock lead the way after her, pulsing in the air as he followed her barely covered ass down the hallway and up a flight of stairs, coming with a stop to the bedroom which seemed to cover most of the top floor. A few doors at the far end, Bobby reasoned, must have lead to a bathroom and closets. One look at this room and he trembled with excitement.

There were chains and harnesses hanging from hooks to one side of the room, a long table displayed an assortment of whips, floggers, ropes and collars. In front of all of this, and for now pulled open, was a deep red curtain, which could obviously be pulled across to hide Mistress's playthings from view if she so desired. A long leather couch sat in one corner, facing a large flat-screen TV which had been mounted on the wall. And taking up the majority of the room was Mistress's bed.

It was a thing of beauty in itself. Four-poster, king sized, and carved from mahogany, Bobby watched as Mistress walked over to it and ran her fingers over the red satin sheets. She then turned to face him.

'Come here and remove my skirt,' she commanded, and Bobby rushed to her side to obey. She turned to allow him easy access to the button and zipper which secured it around her waist, and with slightly shaking hands he undid her skirt and sank to his knees to pull the skirt from her. His head was in line with her pussy when the skirt passed them, and he suppressed a groan. The see-through lace which covered her mound allowed him to see that she was clean-shaven and also a bit wet. The sweet smell coming from her was intoxicating. Pressure on his arm brought him back to reality, as she supported herself on him to gracefully step out of the skirt and lay back on the bed, wriggling herself into the middle of it.

Bobby stood and quickly folded Mistress's skirt and placed it neatly on the floor, before standing at the foot of the bed, eyes cast down and hands behind his back. His cock had started to drip some pre-cum, and he chose to occupied his time by looking at her feet so that he wouldn't be tempted to look elsewhere. He watched as the black thong was pulled down past them, and barely trusted himself to breath. Suddenly Mistress was off the bed and standing beside him, holding her thong under his nose.

'Do you want this?' she asked him, shoving the panties up to cover his nostrils as she said it.

Bobby inhaled deeply.

'Yes Mistress,' he said with a groan.

'Open your mouth.'

Without a second though Bobby opened his mouth wide, and Mistress stuffed the thong into his mouth. The taste of her was sublime, and he closed his eyes in rapture. The light lacy material tickled his tongue and added to the overall effect. Then Mistress's hand clamped down on his mouth and he opened his eyes with a start.

'Do not drop them,' she commanded, and Bobby nodded his understanding.

Taking her hand way, she walked over her wall of toys and selected a few items, bringing them back with her and keeping them from his view. His sight was suddenly taken way from him as he felt Mistress tie something roughly over his eyes. He felt rope slide over his wrists as his hands were tied together. Lastly, he felt a metal chain being slipped over his head and carefully positioned around his neck. A quick tug of it told him that it was a choker chain, and he hurried to follow Mistress's directions.

He felt Mistress push him against a chair and followed her silent instruction to sit. Leather met his bare ass and he assumed he must be sitting on the couch. A minute later he could hear the moans and cries of a porno. He sat, trying to anticipate what was going to happen next. He heard a loud crack and winced, only to discover it had come from the TV and was followed by an exaggerated female moan.

He gradually relaxed to the constant smacks and moans, and settled more comfortably into the couch, awaiting further instructions from Mistress. The loud sound of velcro being torn apart right next to ears several minutes later caused him to jump. He had lost track of were Mistress was, the sound of her footsteps being obscured by the porno, and decided that she must be standing over him. His legs were then roughly pushed apart, with Bobby offering her no resistance and complying with her wishes. He bit down hard on the panties to prevent himself from moaning as her hand brushed against his hard cock, while at the same time fearfully of what might follow. He felt cool fabric being pulled around his cock and held in place. Then her hands were gone.

Bobby turned his head, trying to get an idea of where she was, receiving a sharp blow to the thigh for his efforts. He stopped moving and waited, but not for very long. Slowly but steadily, he felt the fabric encasing his cock tighten, squeezing his penis in the process. At first it was all he could do to stop from moaning in pleasure at the light pressure. As the pressure increased however, moans started to work their way out of his mouth and he received another blow to the thigh.

Bobby did all he could to keep the sounds at bay when the squeezing seemed to reach its maximum force, and he began to struggle against his tied hands. The pain shot through his cock and down into his balls, and he desperately clamped down on the panties, for fear of losing them in a scream of pain. And then the pressure was backed off with a hiss of air and Bobby felt his body slump forward in gratitude.

Blood returned to his cock, pulsing through his shaft and bringing with it new sensations of pain. Bobby however, breathing heavily through his nose, allowed no outward signs of this to show. He was sure he had displeased Mistress with his moaning and struggling, and was ready to take any punishment she deemed appropriate. He heard the moans of a woman being abruptly cut off and realised that Mistress had turn off the porno. A tug at the choker chain had him on his feet, and he followed Mistress until a hand to the chest stopped him.

'Open you mouth,' she commanded, and Bobby did so, allowing Mistress to reach in and remove her panties.

Bobby took in a big gasp of air, and panted a few times before regaining some composure.

'Thank you Mistress,' he said, bowing his head.

He felt the rope at his hands being pulled free and flexed his fingers experimentally. His wrists were aching slightly from damage he had cause himself when struggling against them, but otherwise they were fine. He kept them behind his back as he felt the chain being removed, and then heard Mistress's footsteps fade away to his left before coming back. Light hit his eyes as the blindfold was pulled from him. He waited for further instructions from Mistress but she had gone again.

Bobby stood silently, wishing he knew were Mistress was, and what she was doing. Now free of the restraints he felt strangely vulnerable. He refrained from turning to seek her out, knowing it would only lead to more punishment. He couldn't bear to disappoint Mistress again.

'Now,' Mistress said, her voice penetrating the air as she stepped towards him, 'Let's see what a good boy you can be. Look up,' Mistress commanded, stepping into view once more, now wearing a black harness with a purple dildo protruding from it.

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Thank you for reading Chapter 2 of Bobby's Big Break and thank you all who commented and voted on Chapter 1, I hope that you enjoyed its continuation. The night is still young for Mistress Rose and Bobby, so I hope you will continue to read about their encounter. If you want to hear more about them, please vote or comment. As always, constructive criticism is welcome.