The Training of Tom (part 4)

#NSFW 18+ Sexually explicit content.

Last night had been amazing, and Tom only broke the rules one more time during the whole night. He would have to pay for it, but hey, even he agreed that the pleasure was well worth the consequences he knew were coming his way. Jesus, he was like a machine, he just kept on going! I was in my own version of heaven! No strings attached multiple orgasms for spanking and humiliating this darling man then taking as much pleasure as we could both handle from him, not to mention he was absolutely loving it! In the end… when the heat and the pain and the stinging had worn off some… and after a lot of cold cream had been applied to all affected areas on multiple occasions. Which is what caused the second breaking of the rules… which is why some discipline needed to be applied today.

Sadly for Tom, last night was last night. This was a new day and I had plans for his arse. The spanking session needed to get underway. Problem was, He was working on being the most amazingly submissive but sexually aggressive, superb lover and just all round fabulous guy! I was really happy to be here right now.

By the way, ‘here’ precisely put, was me sat at the kitchen table stark naked with one leg over Tom’s shoulder and him with his head between my thighs making my pussy utterly, delightfully dependent on him! While I sat holding his head and groaning, it suddenly became apparent to me I could kill two birds with one stone. I pulled his head away from my pussy quite forcefully gripping his hair and pulling his head back to look up. He gazed up at me warily.

‘What’s up Gem?’ he asked as he ran his fingers between my pussy lips and let them take over where his mouth had left off.

‘It’s Ma’am to you.’ I said quietly, ‘I require you to get your arse into the front room, lie down on the floor and keep your hands to yourself. I am going to fuck the life out of you.’

I watched as he instantly became the submissive Tom of yesterday and all his swagger disappeared. It was in his eyes, it really was like he was two people in one body. I was utterly fascinated by the transformation.

I patted his head, ‘Good boy. Now, get to it.’

He lowered his gaze and stood up. I took in his gloriously naked body as he walked slowly to the lounge. Damn that man was beautifully put together! I followed him a few moments later with a fresh ginger fig in my hand and an evil smile on my face. We hadn’t gotten around to Tom’s second or third Ginger fig punishments the night before because we had gotten so distracted, but I was very aware of the reaction he had to having one inserted in his arse, after the initial shock from the sharpness of the stinging, burning sensation, his cock remained hard for the rest of the night. Much to my delight.

I approached him slowly, showed him the ginger and watched his face pale. ‘Did you think you could distract me from attending to your punishment Tom?’

‘No Ma’am,’ he shook his head, a worried expression settling on his face, ‘I know I have to be punished Ma’am, but I so enjoy pleasuring you, I truly wasn’t trying to distract you.’

I stood over him, contemplating what he had said and I placed the ginger on the coffee table and then lowered myself down on to his waiting cock. ‘And pleasure me you shall,’ I said. There was time enough for the ginger fig when I had taken my pleasure.

I slid down his length and took him all the way in and ground down until there was no space between us. I rocked my hips forward and groaned as he filled me, stretching me to the limit and then sending shock waves through me as I began to ride him in earnest. My orgasm began to build and I rode harder and faster. He groaned in unison and his face tightened with his fight to control his urges.

Waves of ecstasy washed over me as I rode his huge member, he thrust his hips up to meet me coming down but he kept his hands on his head the whole time. Jesus, I could have ridden him all day he was so good! I groaned loudly as I climaxed long and hard on his shaft. He was trembling, his legs were so tense they were rock solid and I knew he was having the devil’s own time controlling the overwhelming urge to cum just as hard as I had. His face was a study in pain and ecstasy and frustration and I laughed as I continued to ride the waves of my own orgasm. Jesus it was an intense experience with him every single time! I could become addicted!

Finally I climbed off him and stood astride his legs, smiling I reached across to the coffee table and picked up the ginger fig, the lube and a disposable glove. I heard his groan. It rumbled through his whole body.

‘All good things must come to an end Tom, time to turn over and take your punishment.’

‘Yes Ma’am’ he muttered as he rolled while still staying inside the stride of my wide open legs.

‘Up on your knees, there’s a good boy, I don’t want to have to work too hard to do this okay?’

Tom did as he was told and positioned himself on all fours. It was a beautiful sight, his gorgeous thick heavy cock was hanging down below his full sack and they swung slightly with his movement. His legs were set a little apart and his butt cheeks opened up invitingly.

I lubed up my gloved fingers and I played with his tight little hole. ‘Relax Tom or this will hurt like hell.’ I pushed two fingers in slowly and he moaned and relaxed against them. They slid all the way in and I rotated them for a moment, sliding them in and out, watching him buck up slightly, ‘are you enjoying this Tom?’ I demanded sharply. I smacked his left butt cheek hard and he yelped and said quickly, ‘No Ma’am, definitely not.’

I worked my fingers in and out of his hole for a few minutes and he was definitely riding them now, I slid my fingers out as he pushed up and I inserted the ginger fig as deep as it would go. ‘Now squeeze that hole tight shut Tom!’ He squeezed and squealed at the same time and his legs began shaking, his arse tried to push the ginger out and I had to keep my finger against the end of it for a few seconds before he stopped fighting it and groaned deeply.

He allowed the top half of his body to flop down but his backside remained high in the air. It seemed such a shame to waste a golden opportunity for a perfectly positioned arse for a spanking. So I didn’t.

I picked up the Jokari paddle and oiled the wood, then I oiled Tom’s cheeks and thighs and then I went to work on making his arse turn cherry red as quickly as possible. Damn, it’s a good thing my neighbour is deaf! Tom screamed as the wood connected and gripped his cheeks before sliding off and then coming back in the same place. I spanked that paddle hard across his bottom, stroke after stroke, landing across both cheeks, his thighs, then I spanked just the left cheek for a minute until he was begging me to stop, I transferred my attention to his right cheek and then the same attention to each thigh. His bottom was burning hot to touch, welts and blisters were popping up on his overheated skin and he was sobbing loudly into my carpet.

His four minutes with the ginger were up and I still had a number of other spanking sets to get through but he had earned some corner time. I put down the Jokari paddle and pulled on the glove and removed the ginger fig from his hole. He squealed as more juices were released on its way out. It really is the gift that keeps on giving. If you like excruciating pain and a red hot arse, that is. Personally, I can live without ever experiencing it again. Tom wasn’t so lucky, he still had one more 4 minute set to go before the end of today and a whole host of spanking and caning!

‘Okay Tom, corner time please. Go to your corner and stand facing the wall with your hands on your head for 15 minutes. If you move I will insert the last ginger fig immediately. Do I make myself clear?’ I really have developed a very good line in evil over the past 24 hours!

‘Yes Ma’am, I understand.’ He muttered as he got to his feet and all but ran across the room to stand in his corner.

I used the time to set up the spanking machine directly behind him. I placed the clothes brush in the machine and set the timer for the maximum 5 minutes on number 10.

‘So Tom, because we are way behind on the spanking punishments, I have decided to include your next spanking in with your corner time. But, I want to watch so I’ve set up the spanking machine to deliver the 320 clothes brush spankings and Graham’s 38 cane strokes which I will let the machine deliver too. You also still have 290 strokes of the Jokari paddle to take before we are done here. You did break the rules a second time last night and it cannot go unpunished so I am adding a further 10 strokes of the cane for your rule breaking. Now, brace your hands on the wall and push your bottom out for me please.’

Tom glanced over his shoulder at me and the look of horror on his face almost made me giggle. ‘Do you want to say something Tom?’ I asked quietly as I fiddled with the positioning of his arse making sure it was in line with the machine’s arm swing.

He dropped his head down and muttered sulkily, ‘no… ma’am.’

I spanked his thighs a few times. ‘Watch how you speak to me Tom, I will not have you disrespecting me, is that clear?’

He jumped a little and yelped as the slaps stung his inner thighs. ‘Yes Ma’am, sorry Ma’am.’ He braced himself properly on the wall and was bent over to my liking, I switched the machine on. It began it’s tirade of abuse on his bottom and thighs, as he jumped and yelped and lifted and then realised he wasn’t helping himself, those spanks were coming thick and fast and he was sobbing by the end of the first 5 minutes. I turned the dial around for another 5 minutes and without a word I started the machine off again. Oh DAMN did he howl and squeal, (that clothes brush is pure evil) he begged me, he pleaded with me for it to stop. How many times he swore he had learned his lesson I can’t tell you. I lost count after 10. I sat and watched as he took his punishment and I enjoyed every single second of it.

I gave him a twenty minute break to calm down and collect himself. I sat on the sofa and he lay with his arse hanging over the side and his head on my lap as I soothed him.

I reminded him that we were almost done, just two more sets of punishments and one set of the ginger and he would be free and clear.

He cried real tears when I mentioned the ginger. He begged me not to do it to him again, he pleaded with me, he told me he would do absolutely anything else at all if he didn’t have to do that.

It had to stop.

‘You want me to break Graham’s direct orders? Do I look like an idiot to you Tom?’ I spoke sternly to him and he caught the change in tone instantly. He stopped whining, and crying and shook his head. ‘No ma’am, I’m sorry. I’ll take my punishment, I shouldn’t have…’ He tried to apologise, I stopped him.

‘I get it Tom, it hurts. But seriously, It wouldn’t be a punishment if it didn’t hurt! Besides, you signed up for this with Graham, you can’t just pick and choose how he decides to punish you. Be grateful it isn’t him doing it. You at least get to have some fun and cuddles with me.’ I consoled him as I stroked his head. And then he said something that stopped me in my tracks.

‘I’m just grateful you let me come over and took over the disciplining. I was scared to death Leo and Graham would try and turn it into a threesome thing!’ Tom sighed and went quiet.

‘What do you mean Tom? Threesome?’ That did not sound like Graham at all. I didn’t know Leo at all but I did know Graham.

‘Well, earlier on yesterday, before I texted you, Graham had to nip out somewhere and he left me and Leo alone. Leo is a complete bastard when Gray isn’t around, acts all superior like I’m beneath him or something. I told him to watch his mouth when he started ordering me around and he said something about I would be singing a different tune when Gray got back because my next punishment would be handled by both him and Graham. That’s why I texted you. I’m not even Bi, Gem, I liked what you did earlier but that’s cos it was you doing it, if a bloke tried to come anywhere near me I would lose it all over his head!’ I could hear the suppressed anger in his voice and I calmed him.

‘I know Tom, you certainly don’t have to explain your sexuality to me, I get it that the anal play was definitely turning you on because it was me and not for any other reason.’

I pushed him a little, ‘listen to me. You are off the hook for the rest of the punishment regime that was outstanding. I think under the circumstances Graham would do the same thing too. I will say this, whatever that little bastard Leo has said to you, Gray will have had no part in it. It is not his way at all, but I will make sure Leo gets what he truly deserves before this day is out. You can bet on it.’ I was absolutely furious with this Leo character and he was going to find out just how much when I did see him.

Tom sat up and stared at me, ‘Really? I mean, really?? No more ginger or spanking or caning?’

‘Yes Tom really. Unless of course you do something to earn it?’ I was laughing at his relieved expression. He was real easy to train.

He grinned at me, ‘I promise I won’t! So I can be myself again? Not Tom under discipline?’

I grinned widely, ‘Yes Tom you can.’ I knew exactly where this was going. I wasn’t wrong.

He jumped up and grabbed me by the ankles and pulled me down until I was lying flat on the sofa and then he spread my legs…

We were there a very long time…