Bobby's Big Break Ch. 01

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.

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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.