#NSFW 18+ Sexually explicit content.
Warning! The following content contains sexually explicit detail. You must be over 18 to continue reading.
So, I left you in my last post where I had just informed Tom of the contents of the Random Punishment Selector Certificate.
Poor Tom was clenching his buttocks so hard his cane marks had turned into red waves! I decided it was only fair to impart a really sound piece of advice to him before we got started.
‘Tom, if you keep your bottom clenched like that, this is going to hurt like nothing you’ve ever felt before. Relax your cheeks darling and take this like a man.’ I patted his bottom and was gratified to feel him jump at the slight contact. He was officially bricking it! Soft option? Me? Oh dear, he was about to find out I could stand easily at the side of Graham stroke for stroke if I wanted to.
He heard me and relaxed his butt cheeks, pressed his face into the throw cushion and gripped it, locking his arms underneath in a vice grip. He was ready!
‘One more thing before we get started, I have decided to assist Graham with his discipline program for you, I intend to help him out with it when you’re with me. This will be ongoing when you’re over to visit with him or myself. This means your discipline program will be permanent and not just for the original two weeks. We shall pass you back and forth between us. Do you understand what that entails?’
Oh hell! I was enjoying this enormously!
Tom was silent for the longest moment and I was beginning to think he was going to decline when I heard a very small ‘Yes Ma’am I understand completely, you will spank me whenever I am with you.’
‘Yes Tom I will,’ I was stroking his bottom and thighs while I talked quietly with him, ‘ but I will discipline you in other ways too, do you agree? I want to hear you say it please, loud and clear so there are no misunderstandings!’ I was running fingernails over his hot bottom, along the ridges of Gray’s handiwork, down between his butt cheeks and along his thighs and across the back of his sack. He was jumping and twitching and I could hear his breathing change. He was in my zone.
‘Yes Ma’am, I agree to you disciplining me along with Graham and I’m happy for you to carry out any punishment you deem necessary.’ Tom spoke clearly and concisely.
Game on people it is officially playtime!
I was gleeful and so turned on I could barely stand it! I picked up the mineral oil and poured a liberal amount into my hand.
‘Spread your legs wider please darling, I want to make sure I get this everywhere.’ I delivered the instruction as I began to apply the oil all over his red hot cheeks and thighs. He dutifully spread his legs wider and my hand slipped between them and cradled his balls, coating them in mineral oil before travelling forward and taking hold of his wonderfully rock hard cock. I stroked the oil up and down the length of him and heard him groan loudly into his cushion as I continued with my ministrations to his throbbing member. I ran my fingers over the tip and they were instantly coated in his pre-cum, I stood now and pulled his cock backwards between his legs gripping it tightly, I slapped his bottom sharply with my other hand.
‘Remember Tom, you are not allowed an orgasm, so keep it in mind because you will be in a world of trouble and pain if you decide to disobey that order.’ My voice sounded so strict! I was having the time of my life right now and loving every second of it.
Once again, a very small voice muttered ‘yes ma’am’ into the cushion.
I continued with the preparations. I rubbed the mineral oil deeply into his welts and heard his hissed intake of breath, his butt cheeks clenched hard and I smacked them twice to make him relax them. I rubbed the oil deeply into his thighs, between his butt cheeks and into his sack. I continued to play with his cock for a while, stroking it slowly, pulling his foreskin right back and running my finger nail over the throbbing purple head, more pre-cum oozed and I gathered it and lubricated the length of his fine thick cock with it. He was thrusting against my hand now and I laughed and let go. He groaned loudly in frustration.
I stepped back and viewed the glistening show he was putting on for me. I smiled and retrieved my cane. I swished it through the air once by the side of his head, his reaction to that sound made me smile. He jumped and clenched and then released and then clenched again. I moved behind him and into position.
‘Relax them Tom, that’s your final warning.’ As he relaxed his buttocks I brought the cane neatly across both cheeks in a sharp stroke. My cane is exceptionally whip like, and what I lack in power it makes up for in sting.
Tom howled at the first contact, I raised the cane and brought it down again directly below the first stroke. Two welts raised in between Gray’s welts and filled in the spaces! It was a beautiful sight. Tom squealed and squirmed, and I brought the cane in straight across the back of his thighs. He howled, I delivered number 4 across his sit spot, number 5 and 6 followed swiftly landing straight across his cheeks again, filling in the blank spaces Graham had left.
Tom was sobbing loudly now and pleading with me to stop. I rested the cane across his bottom for a moment and cocked my head to one side as my mind ticked away with possibilities.
I waited a few moments to allow the painful throbbing to build up under the skin and I occupied myself by running my hand between his legs and stroking his balls, I cupped them and squeezed them a little, he bucked his hips forward and let out a strangled moan, I crouched down to see his beautiful cock bobbing and jumping. I grinned as I took hold of it and pulled it back between his thighs. Leaning forward I closed my lips over the swollen purple head, he let out a very deep moan as my mouth slid along as much of him as it could access in this position and enveloped him in its moist heat.
I sucked hard on the head as my hand pumped his shaft. He was trying desperately to thrust but couldn’t due to his cock’s position. I laughed and shifted my position slightly in order to take in more of his wonderful shaft and I was rewarded with the taste of his salty pre cum. I was actually very impressed with his staying power and control in that moment because he was begging loudly and his legs were trembling!
‘Please Ma’am, please let me cum, please … ohhh….uhhhh….oh god… please Ma’am let me cum in your mouth, I will do anything you want I promise …. PLEASE just let me cum!! Oh GOD I w….’
I let go of his cock and balls and I stood up. I brought my hands down hard, one on each cheek and then continued to spank him hard for a few minutes. He was sobbing loudly now and was in a complete state. I remonstrated with him for begging for an orgasm and for asking to come in my mouth. His cock was jumping, his arse was clenched and he was stammering out multiple apologies!
I was grinning like the cat that had caught the canary! He really was delightful.
I picked up my cane and brought number 7 down hard across his cheeks. Damn he squealed. I raised the cane again and brought it sharply across his sit spot in a whipping motion and he screamed as it embedded its image into his skin. I finished off with a flourish by bringing 9 and 10 home in a large X across both buttocks! Tom was openly crying now, sobbing and pleading for me to stop. I patted his bottom and moved around him to stand by his head. I lifted my leg up and placed it on the sofa cushion, the action revealed my very wet and glistening pussy in all its glory.
I tapped Tom on the shoulder with my cane. ‘Lift your head up Tom and put that whining mouth to better use.’ He lifted his head up, his eyes were red and puffy from crying, his face was creased from the cushion but none of that mattered because he saw my pussy and buried his face between my open thighs and went to work on my throbbing clit with his very talented tongue. I held the back of his head and pressed his face harder against me , ‘I want to feel your tongue cleaning my pussy of all its juices Tom.’ He did exactly as he was told and buried his tongue deep inside me, licking, sucking, tonguing me until I was moaning in ecstasy, wave after wave of pleasure rippled through my body and I could feel my orgasm building at speed until I felt it rip through me and spill over to fill his waiting mouth. My body shuddered hard and I kept him there until I was completely done. Finally I lowered my leg back down and stood back from him.
‘Good boy! That was wonderful! Now, up you come, it’s corner time for you. 5 minutes facing me, you can remove your t-shirt too, hands on head and do not let them drop until the five minutes are up, then it’s back over here and over the arm of the sofa for you again. Clear?’
He looked dazed, his face was covered in my juices, and he seemed to have not heard me.
I raised an eyebrow at his lack of response and he suddenly got on with it and jumped up from his over arm position and stripped off his T shirt, he took himself off into the corner of the room and then turned to face me.
‘I sat on the sofa watching him for a moment, ‘Drop down onto your knees for me and keep your hands on your head.’
He dropped down onto his knees and remained in position while I took a good look at his wonderful cock. It was impossibly hard now and the ever present pre-cum glistened on the tip. I looked at his bobbing member and then up at his face. He was watching me carefully, it was blatantly obvious he had no idea what I would do next. He was like a cat on hot bricks! I could feel his nerves all the way across the room. I grinned and walked over to him.
I stood directly in front of him and stroked my hand through his hair pulling his head back slightly so he looked up at me. The sexual tension in the room was palpable. ‘Did you like the taste of my juices Tom?’ I asked casually as I ran my fingers through his hair.
The look in his eyes told me everything I needed to know, if he could have had his way, he would have fucked me hard by now. ‘Yes Ma’am I did.’ His response was succinct and quietly delivered. His face however, was showing me the whole story, he was struggling to control his natural urges. He was having a serious battle with himself right now and I was about to make it much, much harder for him.
‘Good answer Tom.’ I smiled at him and turned my back to him. I slid my skirt up above my hips slowly so that my cheeks were in front of his face. I heard him suck in a breath, hard.
I knelt down on all fours and crawled backwards until his huge cock was pressing against my wet pussy and then I rocked back onto it, letting it slide all the way in and fill me, stretching me until I was impaled on him. I groaned deeply, he was glorious!
‘Do not move a muscle Tom, I am going to do the fucking, not you. You shall just provide the cock. DO NOT CUM. Is that clear?’
He was trembling, but his hands remained firmly on his head and he bit out in a strangled voice, ‘yes Ma’am, very clear.’
I pumped back and forth on him, taking him all the way in, grinding back onto him until my bottom was pressed against his groin, then releasing him and sliding all the way to the tip, Tom was moaning loudly, begging me to ride him harder, faster and I continued to ride his beautiful cock for the whole 5 minutes before I rocked back hard and came all over his thick shaft. Jesus, I saw stars. I came so hard! I dropped myself forward and let his cock slide out of me. I was still shuddering from the force of the orgasm and I needed a few moments before I could stand up. Eventually I stood before him and slowly lowered my skirt back down over my thighs again. I turned to face him and damn but his face was a picture of pain and ecstasy and frustration. His cock was bobbing so hard and looked so swollen I thought he might explode. I grinned at him and patted his head.
‘Good boy Tom, you didn’t cum. Now, back over the arm of the sofa please and remember to spread your legs.’ He closed his eyes and groaned quietly but did as he was told and got to his feet.
He must have been in agony, his cock stood out ramrod straight in front of him as he walked over to the sofa and assumed the position. I sat down in the chair facing him and hung my leg over the arm while I stroked my pussy into a calmer state. She was very excited by all this activity! I made him wait 20 minutes while I soothed myself with yet another orgasm. He could listen to me moan and coo as I worked my body into that wonderful state of pleasure but he wasn’t allowed to watch. His face remained firmly against the cushion and his arse remained beautifully on show with his cock bouncing against the side of the sofa and his balls hanging free.
It was almost time for the second part of his punishment.