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.

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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.