Tom's Journey into Submission

Tom didn't know if he was relieved or not. Control his erection? He'd never tried to do that before. Penalty? Extra strokes? Time to find out.

Of course, he couldn't prevent his cock from showing its pleasure at being freed of its clothing. As Tom removed the final item, he stood up and placed his hands behind his neck, as taught to him on his last visit here. No amount of mental arithmetic or trying to remember the succession of kings and queens could hold back the powerful erection he developed. Proudly thrusting up and out towards his tormentress. Tom blushed his shame at failing to obey her as his cock pulsed with his heartbeat.

"So, immediately you are given a command, you disobey it. Not a good start for a slave, is it Tom?"

"S-s-slave, Miss?" he asked, bewildered.

"Oh, yes, Tom. You are my slave now, and you will address me as 'Mistress' when you come here to do my bidding. And the first thing we need to do is place that offensive penis of yours under control. Follow me." And Evelyn walked to the Punishment Room door and held it open for the naked Tom.

"Leave your clothes in the hall, Tom. You won't be needing them for some time."

Tom was beginning to wonder if he had been foolish to come here. Things weren't going the way he had imagined. He had thought Evelyn would simply take him to her room and cane him. He would then be free to go back home and masturbate. After three days of steady thought about this, he had a huge store of cum to offload. His cock bobbed back and forth as he walked into the room where silence descended as the door was closed behind him. Once again, the spider had her prey on her web.

"Hands behind your back, slave." Evelyn commanded, and Tom complied. She took some leather cuffs and attached them to his wrists and connected them with a short chain and some clips. This was new, and erotic to Tom. She grasped his erection and gave it a few strokes, causing Tom to moan with pleasure as she fondled his balls inside their tight scrotum.

"When did you last ejaculate, Tom?" she asked him.

"Three days ago, Miss."

"Mistress! Mistress is what you call me!"

"Yes Mistress. I'm sorry. I have held off for three days, Mistress. It hasn't been easy." He added.

"No, not for a young man like you, who likes to ejaculate out of his window. Would you like me to continue stimulating you now, until you ejaculate, or would you prefer me to give you the caning you so badly want?" A simple question, with a devious conclusion, as Tom was about to find out.

"I think maybe I should take my caning first, Mistress. I've read it makes it more tolerable for the person being caned if they have a lot of cum built up. So, Mistress, please cane me before you make me cum."

Evelyn beamed at him. "Very well, Tom. I seem to be doing everything you want me to do today. Is that the role of a Mistress though? I think not. I think therefore that is something I shall do before we continue further."

"I find pubic hair on a man unnecessary. So, firstly, we are going to remove yours. It is a fine example of the slave's willingness to submit to his Mistress. You may lie on the chaise longue and I shall perform this service on you. Don't worry, I'll use a proper beard trimmer to start with."

Forty minutes later, Tom looked down at his bald pubis. She had done a superb job and between his navel and his knees, there was not a single hair remaining, The beard trimmer had taken the bulk of it, but then she filled a bowl with hot water and gave him a wet shave, paying close attention to his scrotum and anal area; a process he found deeply humiliating. Finally, she applied a defoliant cream and rubbed it in carefully. Carefully because she didn't want to make her victim cum and his cock was bursting with all the attention it was getting. Three days of abstinence at that age was a long time, she knew. For the finale, she gently applied an after-shave cream to soothe, moisten and lubricate the area.

Tom was now in love with his Mistress. No girl had ever shown him so much attention, and like the fool that he was, he thought it was because she cared about him. Nothing was further than the truth. As he was about to find out.

Evelyn placed a blindfold on Tom, making sure he could not cheat by looking down the side of his nose. He was ordered back onto his feet and his cuffs were re-attached behind his back. His cock was as hard as an iron bar and dribbling pre-cum. She removed the latex gloves she had worn for the shaving procedure and donned a new, clean pair. She went to the fridge which she kept in the room and broke a tray of ice into a bowl. She then laid out a tea towel and poured some ice cubes into it. Approaching Tom, she bent down and secured the towel with the ice around Tom's raging erection, binding it with a leather cord tied around his cock and balls. These were now in direct contact with the ice.

"That will remain in place until your erection has subsided completely, Tom. You wanted me to find reason to punish you - well here it is. For each minute we wait, you will receive six strokes of the cane."

Tom remained standing, naked and humiliated with his hands cuffed behind his back and his cock wilting as the freezing took effect on his hard-on. Within two minutes it was totally deflated, but Evelyn made him stand for a further minute before she rose from her chair and with a smirk, removed the binding cord and the tea towel. Poor Tom's cock was shrivelled and his balls were aching.

Evelyn took a tube of lubricating gel and slathered it all over Tom's now soft cock and balls. She produced a metal ring and fitted Tom's genitals into it, feeding both cock and balls through the large ring. Quickly, before he could sense what was happening, she took a small, curved metal cage from its box and, having fed Tom's still flacid dick into the ringed cage, she fitted the cage and the larger ring together and turned the key in the lock. Tom's cock was now inaccessible to him. He knew something interesting had occurred, but it was only when Evelyn removed his blindfold that he could see what it was.

"That's right, Tom. Your cock is now mine. The cage will prevent it from growing into an erection, but you can still use it to go to the toilet. You may find it easier to pee sitting down though." She took the keys, there were two, and hung them on a board on the wall beside half a dozen other sets of keys, each one numbered. The board was set in the wall with a glass door in front of it, which she now closed and locked with a key hanging from her neck on a chain. He had sometimes wondered what the key was for, and now he knew.

"You are number seven, Tom. Not double-O, I'm afraid. Just number seven. Remember that, in case I forget. You might want to reflect on all this, and of course, don't forget you are still due to take eighteen strokes of the cane. You may beg for them when you are ready. I shall be reclining by the pool." And with a smirk, she left the room.

Tom was struck dumb. Things were not going the way he had been dreaming about. It's one thing to go to a lady and ask her to give you twelve strokes of the cane, but it's a very different thing to find yourself less than an hour later enslaved - naked, hands cuffed behind your back, shaved bald, with a caged cock and now wondering how serious his dilemma was. Should he refuse to play her game any more? He could just leave this room, grab his clothes and dress and go home. Except his cock was in a cage and she had the key.

Maybe this is just to increase the pleasure she will get when she canes me and she will release me when it's over. She did say she would wank me off after my caning. I hope she did anyway, because now that I think of it, she didn't actually say that she would. I'm in no position to negotiate with her. She literally holds the key. But I can see the key hanging there on its hook. I daren't break the glass though. She would be furious. I guess I'm just going to have to go along with this. Maybe she will tell me what happens next. That's it. I'll go and beg her to cane me now and maybe she will unlock the cage and toss me off. That would be great.

And as Tom was thinking these thoughts, Evelyn was basking by her pool, clad only in tiny micro briefs which actually had been sucked inside her outer pussy lips, and apart from the strings holding the garment in place, she appeared to be totally naked. She wondered how long it would be before Tom came to beg for his caning. She knew he would. It was his only bargaining chip, particularly as she had taken his clothes and placed the out of sight in the hall cupboard.

It took ten minutes before Tom knew that's what he had to do. He was able to turn the door handle, even with his hands behind him, and could see his clothes had been moved. He guessed Evelyn would be out by her pool so he made his way there.

My god, she's naked. Tom could feel the blood flowing into his cock, and the sudden lurch on discovering there was nowhere for it to grow into. He couldn't get an erection now. Oh, god how he longed to be able to feel its freedom again. And it had been less than 15 minutes!

"Er, Mistress," he started, "Would you please administer the caning I earned? You told me you plan to give me eighteen strokes today and I am ready to take them." His cock strained against the metal rings of the cage and Evelyn's mouth twitched in amusement at the boy's predicament. He was standing with his back to his own house, so he could not see what suddenly became apparent to Evelyn. Tom's mother had just walked past his window. She was in his room, probably wondering where he was.

"Tom," she said quite loudly, "Place your feet apart and bend over. I am going to spank you. He complied almost immediately, presenting his bedroom window with a clear view of his naked bottom. Evelyn rose and walked behind him, adjusted her garment so that, although it concealed nothing, it was more comfortable, and gave Tom three hard slaps on each buttock. She too now had her back to her neighbour's window, but she felt sure Andrea would have heard the sound of the spanking.

Making a slight adjustment to her stance, while Tom remained bending, she was able to glimpse half of Andrea's face peering from behind Tom's curtain. Haha. Dear Andrea. You too? Spying on your neighbour?

All Andrea could see was her 'mistress' Evelyn, spanking someone's naked bottom. The boy, it looked like a boy, was bending and she couldn't see his head clearly, but she could see the reddening cheeks of his ass. Surreptitiously, she inched towards the window and eased it up a few inches, believing she was not being observed as both people had their backs to her.

"Six more, slave?" she asked loudly enough for Andrea to hear clearly, and to her shock, she recognized the voice which replied.

"Yes, please Mistress. Please spank me more." Evelyn smacked the boy again and it was clear he was feeling each strike. "Please give me another six, Mistress." He begged after the first dozen was concluded. Andrea stifled a gasp of astonishment. Even as she watched her son being spanked, she was wishing it were her. She stood up right at the window and started to rub herself. As the sound of the eighteenth slap receeded, Evelyn turned round and looked directly at Tom's window. There was Andrea, standing there rubbing her pussy through her skirt.

Andrea knew she was caught. There was no pretending she wasn't. What she expected to see was a furious Evelyn, but no. Instead she gave a triumphant smile, pointed her finger at Andrea, and then wagged it, as if at a naughty child. Andrea sank to her knees, just as her son stood up and turned around. He had no idea she was there. His attention was on Evelyn who was turning back to him. Andrea caught sight of the cage on her naked son's genitals, stared in disbelief for a moment and dashed from his room.

"You will now proceed to the Punishment Room where I intend to give you eighteen blistering strokes of the cane on your naked buttocks. Does that please you, slave? You asked for twelve when you arrived here and that has risen to eighteen. You will bear the marks for quite some time."

"Yes Mistress. Thank you, Mistress. I'm sure I deserve to be caned hard." And Tom led the way to the room where without being told to do so, he climbed up onto the armchair and positioned himself to take his punishment. His cock swelled painfully against the unyielding metal cage, unable to erect properly.

"You may wish to cry out if you feel the pain too harshly, slave, but I would prefer to hear as little complaint as possible. Fight the urge to be noisy, even if the pain becomes unbearable. I assure you, you will learn to take a much more severe caning than the one you will receive today."

As she was speaking, Evelyn was securing the lad in position. I know he wants to be caned, but we can't have him changing his mind and trying to evade his punishment. Besides, I enjoy knowing that the slave is helpless. Only Lily gets to be unrestrained. And now, I have a phonecall to make. Without explaining her reason, Evelyn quietly exited the room, leaving Tom to stew in his bondage and anticipation of the harsh caning he was about to receive.

"Hello?" a timorous response to the ringing of her phone. Andrea had been lying on her bed, frantically masturbating as she pictured the scene she had just witnessed in her neighbour's garden. Her own son, Tom, naked and begging to be spanked, with a shiny metal cage constraining his penis and balls. Andrea knew what would happen next and was imagining herself taking the punishment instead. And then her phone had rung.

"Hello my little kitten. This is your Mistress. You know you were caught peeking out into my garden, so you will also know who is at present secured in the caning position in my Punishment Room. I am not going to ask you, I am commanding you to come over here instantly to witness Tom receiving the eighteen strokes of the cane he requested. Come now, dressed as you are. I expect to hear my doorbell in less than two minutes." Evelyn did not wait for a response. She put down her phone and waited with a wicked smile on her face.

She briefly returned to her victim to place a blindfold over his eyes.

Andrea, meanwhile, was busily washing away the juices from her masturbating. She leapt into a track suit without wasting time looking for fresh undies and quickly left the house and went next door, unquestioningly obeying her mistress's instructions. She could guess the consequences of not doing so. She pressed the doorbell just as the door was opening.

"Oh, just in time! Had you not been standing here, poor Tom's punishment would have had to have been doubled. As would yours. Welcome, Andrea, please come in."

"Thank you, Evelyn. Uh, Mistress. Mistress Evelyn." Andrea's heart was pounding; from her dash from her bed to here, and what she was expecting to see and do in the next few minutes.

Evelyn produced a ball gag and placed it in Andrea's mouth, securing it in place with buckled straps at the back of her head.

"Just to keep your comments to a minimum, my dear." smiled Evelyn as she opened the door to her Punishment Room and ushered Andrea in. Pointing to a high stool, she indicated that her visitor should sit. Andrea did as she was told and took her place, directly behind her naked, bound son.

He was obviously aware that there was now an additional person in the room but blindfolded as he was he could not see who it was. His ears gave him no clue either.

"Tom the slave. Why are you here?" Evelyn started the proceedings.

"I came to you and requested that you cane me again, Mistress."

Mistress? He's already calling her 'mistress' Like I do? Andrea's stomach fluttered.

"And how many strokes of the cane would you like me to administer, slave?"

He's her slave now? Like me? Andrea felt her fluids building again.

"Eighteen strokes, Mistress. Please give me eighteen strokes of the cane."

And how hard would you like me to cane you, slave? Gently or hard?"

"Please cane me hard, Mistress."

"Would you like to carry the marks for one week or two, slave?"

Oh, Christ. She's a monster. She wants me to beg to be caned harder than ever and I can't even get a hard on.

"Two weeks, Mistress. Please cane me so hard the marks are still there after two weeks."

"Very well, slave. Your request is granted. May I remind you that I did not instigate this meeting today. I am merely acceding to your wishes. Remember too, that I appreciate a slave who takes his beating quietly. There will be no shouting or screaming."

And with that, Evelyn began her work, as an astonished Andrea watched the lines developing across her son's buttocks. Strangely, she had no sympathy for him. Instead, she felt her arousal increasing at each resounding stroke, as the slave stoically took his punishment with the minimum of fuss. Andrea had a sudden brainwave. This is what Kay's Amelia needs - a damned good thrashing. I wonder how we can persuade her to come here. As for Tom, he obviously wants what he is getting and males deserve to be punished anyway, so there is no issue here for me to worry about.

Three final shriek-worthy strokes landed on Tom's backside and he moaned and writhed as waves of pain took him. Tears filled his eyes, but other than stifled sobs and huge intakes of breath, there was little sound and no complaint. Eighteen uncountable lines decorated his arse, many covering previous strikes, and dots of blood oozed out from three dark stripes which had taken the hardest strikes.

"What do you say to your Mistress, slave?"

Tom responded between sobs. "Thank you for caning me, Mistress. It was extremely painful for me but I hope it gave you pleasure."

"Oh, yes, slave Tom. I enjoyed inflicting the pain on you, and from the looks of things, your mystery witness enjoyed herself too."

Andrea was visibly aroused and was gently stimulating one nipple while with the other hand, she was rubbing herself through her tracksuit bottoms. They in turn were obviously absorbing her juices.

Evelyn continued. "As a special reward, I sentence you to further torment. When you believe the marks from this caning are clear, completely clear, you may return to me to ask permission to remove your cage. Until then, you will wear it with pride, and with no remission. It is quite hygienic and if you wash properly, there will be no rashes or skin problems. Return to me when your stripes are gone and I will allow you the pleasure you so desperately seek."

Oh, my, goddd! Whattt? I begged her to mark me for two weeks. Leave me bound like this into the metal cage for that long? I can't believe it. How am I going to wank?

Tom was silently processing his sentence and Andrea continued to gently rub herself. She knew that she too would soon be bent over the back of the chair and the thought was making her exceedingly horny. She didn't know whether she would be caned quite as hard as Tom had just been, but she knew that it would stimulate the submissive in her as well, so if she had to take a similar caning, she would accept it as fair. She was also picturing her friend Kay's daughter being punished with the cane and hoping that one day she would be allowed to witness such punishment.

"Go home now, Tom. You may wish to confess to your mother that your cock is now in a cage and that you are from now on forbidden from looking out of your bedroom window. I know there is a third bedroom in your house, one without such an exciting view. Perhaps you might ask your mother if you can be moved there. Tell her the real reason if you wish."

Evelyn motioned Andrea to leave the room, mouthing and miming that Tom should see her at home first, but that she must return a five o'clock for her own beating. Andrea meekly obeyed and quietly exited the Punishment Room as Tom's bonds were released by his, no, their Mistress. She slipped out of the house and walked home speedily. She had soaked her track suit and needed to shower and change for her appointment in a couple of hours, and Tom should not be aware of her witnessing his caning.