4 comments/ 18822 views/ 2 favorites Bobby's Big Break Ch. 01 By: MsRoseEvans Bobby stood hesitantly on the front porch of her lake house. There were no other houses nearby, and the only source of light other than that of the moon came through the windows of the house. Questions raced through his mind, preventing him from going any further. What if it wasn't her? What if this was all some trick? What if there were actually five guys in there waiting to attack him, rob him, and leave him there to die? What if it was her and all of this questioning had made him late? It was this last question which drove him on, and he tentatively knocked on the door. There was no movement from the house for almost a full minute and Bobby was moments away from returning to his car when the door was opened, light streaming through the now open doorway. Bobby blinked a few times at the sudden light, but could not make out anyone standing in the doorway. He took a deep breath and hurried inside. The door snapped shut behind him and he turned with a jump. Standing in front of the door was Mistress Rose. He had never seen her before, but from the description she gave of herself there was no doubt in his mind. Her mahogany hair was tied in a long ponytail, which hung forward covering her left breast. She was wearing a red satin robe which covered her from wrist to ankle, tied firmly around her slender waist. She was a few inches shorted than Bobby, standing at 5 foot 6 inches, and was standing barefooted before him. 'Shoes and socks off, leave them by the door, and follow me,' she commanded as she walked off into the next room. Bobby bent over to untie his shoelaces and in his hurry and nervousness fell flat on his face. Becoming red in the face from embarrassment, he hastily removed his shoes and socks and shoved them roughly by the door. He was turning to follow her when he caught his mistake in time and carefully straightened his shoes and socks so that they were neatly positioned next to the door. Mistress had repeatedly cautioned him against being untidy while at her lake house and Bobby didn't want to get off on the wrong foot. 'How long does it take to take off a pair of shoes and socks?' Mistress sneered disapprovingly from the next room. Bobby glanced at the door once more to make sure it was appropriate, and then hurried into the room Mistress had called from. Mistress was reclining on a couch, waiting impatiently for him. Once he entered the room she sat up and beckoned to him. 'Stand there,' she said, pointing to a spot on the carpet roughly 5 feet from her couch. He lowered his gaze as he approached her and clasped his hands behind him as previously had been discussed. 'Mistress, thank you for seeing me. I can't tell you ...' 'I did not give you permission to talk,' she interrupted with a snap, and Bobby fell silent at once. She reclined once more into her couch, eyeing him appraisingly. 'Turn, slowly,' she demanded. Feeling more than a little foolish, Bobby did as she commanded. 'Now take your shirt off and turn again.' Bobby unbuttoned his shirt, quickly folded it and placed it by his feet and then turned. He wished he could look up and see Mistress's reaction, to know whether he pleased her or not. He didn't consider himself anything spectacular to look at, but he had done considerable work on his body, making him well-toned all over. Mistress chose to say nothing about it though. 'Remove your pants,' she said, and he saw out of the corner of his eye that she had sat up to have a closer look at this part of the reveal. As per their earlier discussion, he was not wearing any form of underwear. He removed his slacks and after folding them and putting them on the ground on top of his shirt he made to turn and was met with a fierce slap across his bare ass. He gasped and his cock twitched into life, becoming slowly erect. He had not heard her get up and was surprised by how strong she was, the blow causing him to sway forward considerably. 'I did not tell you to turn that time,' she hissed in his ear. 'You will have to learn to pay better attention than that if you want to stay.' 'Sorry Mistress, I will Mistress, thank you Mistress,' he said hurriedly, wondering if he would be punished for voicing his apologies, but Mistress made no comment of it and instead started circling his body to inspect every angle. Mistress reminded Bobby of a shark, the way she continued to circle her prey. Occasionally she would reach out and scrap a fingernail again his skin and he shuddered at the sharp sting, his cock becoming more and more erect each time she did so. 'Bend over and touch your toes,' she commanded. Bobby hesitated for a second and felt her hand smack on his ass once again. 'I said bend over,' she whispered menacingly, Bobby quickly complying. He felt her hands gently rub over his cheeks and then down the crack between them. He felt her spread his cheeks wide open to inspect his hole. He flushed red from embarrassment of being looked at like this, but his cock continued to grow. After what seemed an age to him, she step away. Bobby continued to stand bent over at the waist, waiting for Mistress's permission to move, when he hear a swish through the air, followed by a sharp sting on his ass. He gasped and turned his head around to see what Mistress was doing. Still donned in the red silk robe, she had produced a short black-leather flogger which she held tightly in her right hand. See him turn back to look at him she struck him with it again, just enough to get his attention. 'I did not tell you to turn around, you naughty boy,' she said disapprovingly. Bobby felt his heart sink. He wanted badly to do everything right for his Mistress, and now he had disappointed her. 'I'm sorry Mistress,' he said as he turned forward once more. 'Ten for turning around when you weren't permitted. Count." "Yes Mistress. One Mistress,' he said as he felt the first sting hit his ass. It was not hard, but he had a feeling she was simply building, and allowing him to adjust to what was to come. He silently thanked her. 'Two Mistress,' he counted. She did not vary the force she hit him with, only the tempo. She delayed between counts four and five making him wonder if she was still there, then delivered eight, nine and ten in rapid succession, so quickly he was barely able to keep count. 'Ten Mistress, thank you Mistress,' he finally said. His ass was stinging a little, but nothing he couldn't put up with. Frankly he was surprised at how lightly he had gotten off. He waited for permission to straighten back up, but was met instead with Mistresses laugh. 'Did you think I was finished? That the naughty little boy was all forgiven? Oh no, there is still more to come,' she said savagely, and Bobby trembled slightly in anticipation, his cock twitching at her words. 'Ten going to turn around after taking off your pants. Count.' 'Yes Mistress. One Mistress,' Bobby stammered and kept count during the constant rain of stings against his arse. She was harder this time and more consistent, causing him to hurry along with her in the counts. 'Ten Mistress, thank you Mistress.' "Ten for talking without permission to speak. Count.' Bobby dutifully counted all ten. 'Ten for making me wait while you took off your shoes. Count' The rain of stings intensified and Bobby struggled to keep up with the count. He had barely been with her ten minutes before the flogging had started and Bobby was shamed by how many mistakes he had made already. He felt the sting absolve him for his transgressions against her and resolved to do better for her in the future, if she would still have him. 'Ten Mistress, thank you Mistress' 'Kneel,' she commanded. Bobby hastily dropped to his knees. His arse felt like it was on fire, the stinging burning into his flesh. He felt a jerk at his chin and he was forced to look up into Mistress's eyes. They were a delicious dark brown, perfectly framed by long delicate eyelashes, her eyelids dusted with a light purple colour. And they were very angry. 'Twenty more for having the audacity to question me by even considering not knocking on my door when I told you to come here,' she said in barely more than a harsh whisper. Bobby froze. How could she have known what was running through his mind when he stood on the front porch? Had she been watching him? He thought to argue with her, but knew she spoke the truth and that his punishment was well deserved. So though his ass was already burning from the sting of her short flogger, he bent down on his hand and knees. 'I'm sorry Mistress,' he whispered into the carpet. Twenty more blows rained down on him, starting slow and building up in intensity. His shame at disappointing his Mistress had caused his cock to soften, but the flogger on his ass soon repaired that. The stinging slowly levelled out so that it was all just one dull pain which he pushed to the back of his mind, the punishment making him stronger, his desire to show Mistress that he could take it, was willing to take it, to please her. At last it was over. 'Twenty Mistress. Thank you Mistress,' he said, drawing strength from her strength. 'It will never happen again Mistress.' 'Kneel,' she commanded, and he again felt her grab his chin and make his eyes meet hers. 'See that it doesn't,' she said as she stared down at him. Then she left the room. @>----%---- Thank you for reading Chapter 1 of Bobby's Big Break. Chapter 2 is currently being worked on, so if you would like to hear more about Bobby and Mistress Rose, please vote or comment. Constructive criticism is always welcome. Bobby's Big Break Ch. 02 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. @>----%---- 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. Bobby's Big Break Ch. 03 Bobby eyed the strap-on Mistress was wearing and his mind rebelled instinctually. He had no idea what she was intending to do with it, but every part of his body and mind screamed no. The black leather harness curved tightly around her hips and upper thigh, leaving her pussy exposed to the warm night air. Her clit however was hidden under a black triangle which was the base for the dildo she had attached there. It was 6 inches long and so somewhat small when compared with his 7 inch cock, but in his mind it was monstrously large and he wanted it nowhere near him. Just looking at the purple rubber dildo, adorned with realistic veins, made him gag slightly and take a step back. 'Mistress ... please ... I don't want ...' 'I'm not interested in what you do or don't want,' Mistress snapped, as she repositioned the harness slightly to a more comfortable position. 'You are here to please me and me alone. If you want to leave, by all means go - but don't ever come back. So you can either leave now or you can stop being a pussy get on with it.' Bobby groaned and shook his head, not sure of what to do. His throbbing cock demanded release, and now that Mistress was in his life he couldn't bear the thought of losing her. There was never really any choice. He hung his head and submitted. 'Yes Mistress,' he murmured. Mistress gently grabbed his chin and lifted his face, making him look into her eyes. 'Good boy,' she whispered to him, and lowered her lips to his and kissed him. Bobby felt his whole body tremble in that one brief kiss. She was so soft and caring, he almost forgot about the pain she was able to cause. It was like there was two of her, deliciously wrapped up in one body, soft and hard, pleasure and pain, kind and merciless. And then it was over. She abruptly pulled away from his lips and turned her back on him, leaving him feeling worthless. He watched as she lay on her bed, the dildo jutting straight up from its harness. 'Come, ' she demanded, and rising from his knees he walked to the side of the bed, eyes lowered and hands behind his back, awaiting her instructions. 'Your little display has displeased me. We will deal with your punishment for questioning me later. For now though, remove my jacket and suckle on my breasts. Show me why I should continue to put up with you.' 'Yes Mistress, I'm sorry Mistress,' Bobby said as he carefully reached over and unbuttoned the jacket, her breasts springing free of the tight material. Bobby gazed at her uncovered chest, overjoyed at the fact that he would soon be touching her. A hard pink nipple adorned each of her large DD breasts, betraying Mistress's arousal. Bobby felt a rush of satisfaction at this, and did his best not to smile. He had pleased her, at least a little, and that meant everything to him. Mistress sat up briefly to allow him to remove the jacket, before lying back down and gesturing for him to begin. Bobby carefully folded her jacket and placed it on the end of the bed, Mistress smiling ever so slightly in approval of his action. He reached out with his left hand to massage her right breast while servicing her left with his mouth, only to have it smacked aside roughly before it made contact. 'I told you to suckle on my breasts. I did not give you permission to touch them with your hands. If I decide I want your hands on me I will tell you. Now suck my breasts, and don't make me wait any longer.' 'Sorry Mistress,' Bobby said, and lowered his mouth to her left breast and began slowly and gently sucking, his cock becoming erect once more at the feel of her nipple on his tongue. Mistress allowed the slow pace to continue for a while, before snaking her left hand into his hair and gripping it in her fist. 'I said to suck it, not play with it,' she snarled, and crushed his face into her breast. Bobby began to suck in earnest, and a low moan issued from Mistress' throat. His erection twitched in response as he continued to assault her breasts with his mouth. 'That's it, you naughty boy, suck my tit. You like that don't you, you naughty boy.' Bobby moaned through his mouthful and Mistress's hand fell fast on his ass, causing his hips to buck and another moan to sneak out, which in turn got him another slap on the ass. 'Don't talk with your mouth full you dirty boy,' she ordered through her gasps of pleasure. She allowed him to continue for a few minutes before grabbing hold of his hair once more and pulling him off her tit with a loud popping sound which made her smile in delight. A movement caught his attention and he looked down to her waist to see her rubbing her strap-on with her right hand. She watched as his cock swelled. 'You're wishing it was your cock I was stroking right now, don't you? Answer me." 'Yes Mistress,' he replied, gazing at the dildo with a stab of jealously. Mistress removed her hand from the dildo and held out her hands for Bobby to help her off the bed. Once she was standing she faced Bobby and put a hand on his shoulder and applied downward pressure. 'Kneel,' she demanded. On his knees, Bobby was at eye-level with the strap-on, and hastily looked down to avoid it. Mistress grasped his chin and jerked his head up to meet her eyes. 'You will now suck my cock. You may touch any part of me from the waist down, other than my pussy, to aid you in doing this. Do not disappoint me.' With that she left go of Bobby's chin and instead placed her hand on the back of his head. With the other hand firmly grasped at the base of the dildo, she slowly but forcefully guided his mouth to her waiting cock. Bobby screwed his eyes closed and waited for the dildo to reach his gapping mouth. At the first feel of rubber on his lips he instinctively pushed his head back, but the hand Mistress had placed on the back of his head prevented him from moving too far. She slowly moved the dildo over his lips, tracing their outline, tormenting him with what he knew was to come. 'Look at me,' she commanded. Bobby looked up into her eyes as she continued to caress his lips with her cock. She let out a moan of approval and gave Bobby a smile. 'There's a good boy,' she whispered. 'Now open wide.' Bobby stretched his mouth open and kept looking up into Mistress's eyes and she pushed her hips forward and slipped the dildo in slightly. The rubber felt strange on his tongue. He felt Mistress push on the back of his head and he obediently slid further down the dildo until she no longer forced him, about halfway down its length. He paused, awaiting further instructions. 'Suck it.' These two simple words were the hardest instruction Bobby had heard all night. Having never done such a thing before, he had no idea where to begin. He willed Mistress with his eyes to help him, to teach him how she wanted it done, how best to please her. He was met with only her cold hard stare which was becoming increasingly more annoyed as time dragged on. She let go of the base of the dildo and grasped his hair in both hands to keep him still, and thrust her hips forward in a quick motion several times in a row. The rubber hit the back of his throat each time, causing him to gag. His scalp stung from Mistress pulling on his hair. But through all this he continued to look up at her, as she watched him react to the dildo. She stopped and allowed him a brief respite from her thrusting. 'Now are you going to behave, or am I going to shove this cock down your throat myself?' Bobby nodded his understanding and began to slide his mouth up and down the length of the dildo. He was beginning to loose his balance, and so, remembering her earlier allowance, gently grasped hold of her upper thighs to steady himself. She moaned softly at the contact and closed her eyes for a moment. Bobby concentrated on her legs as the dildo slipped in and out of his mouth, slowly running his hands up and down her tights at the same tempo. He felt her weight shift as she placed her feet further apart, spreading herself open. 'Do not stop sucking. I want you to gently trace the lips of my pussy with one of your fingers. Do nothing more unless I tell you to.' Bobby groaned around the dildo as soon as the words had left her mouth. She was allowing him to touch her pussy, and he was elated. He slid his right hand up her thigh until he met her lips, and gently ran the tip of his index finger along the length of them. He wished he could see, the glimpse he had caught earlier had merely teased him. Her eyes watched him like a hawk as he completed the tasks she had set him, and he tried desperately to keep coordinated while under her scrutiny. 'Very good. Now I want you to slip that finger inside of me, and finger me while you suck my cock. Start slowly and build from there. I want you to count to fifty while you do this. Once there I want you to let go of my leg and stroke yourself gently, counting to 20. Once you have done this you are to stop everything immediately, place your hands behind you and lower your eyes. If you come during this you will be sorry. Do you understand?' Bobby nodded eagerly, his finger itching to slip into her pussy. Her lips had become very slippery and he knew her pussy would be warm and sopping wet. The dildo in his mouth had become nothing more than a background noise. He was continuing to service it as ordered, but her body was what he was focused on. 'Begin,' she whispered. Bobby gently slid his index finger into her waiting pussy. As he predicted she was extremely wet and his finger slid in easily. He watched as Mistress's eyes fluttered shut as his speed increased. Her hips started bucking slightly, forcing the dildo further down his throat, and she would open her eyes and look down at him when his happened, only to groan and close her eyes tightly again. By the count of 25 he was ramming his finger into her as hard and fast as he could, watching her face contort as pleasure started to overwhelm her icy demeanour. He knew his cock was dripping pre-cum on her carpet, and hoped he would be forgiven. As he approached fifty he slid his left hand down her leg and on fifty took hold of his cock. Mistress opened her eyes and watched as Bobby slowly stroked his straining cock and did his utmost to keep counting, fingering and sucking while looking up at her without coming. The notion of simply wanking himself off and dealing with whatever the punishment was tempted him sorely, but the increasingly loud moans from Mistress reminded him that it wasn't about his pleasure, it was about hers. He reached twenty before he knew it, and closed his eyes hard. He dropped his cock and pulled his finger from Mistress's pussy, clasping them behind his back. He backed away from the dildo, and Mistress's hands gently caressing his head as he pulled away. The act of kindness touched him deeply and he smiled up at her though his eyes where still closed. He then bowed his head and opened his eyes once more, awaiting her next challenge. @>----%---- Thank you for reading Chapter 3 of Bobby's Big Break. If you want to hear more about them, please vote or comment. I look forward to hearing from you.