Tom's Journey into Submission Pt. 04

Tom's journey into submission. Part 4

Tom was alerted to the action by a splash from across the wall. He rushed upstairs and into his old bedroom, with its painted-over window. He eased it up a few inches and peered out into his neighbour's garden. He had to look. He was eighteen! Of course he had to look. A second splash and a girlish shriek to follow. Tom raised his eyes over the parapet and was awe struck with what he saw, just twenty yards from his window.

As expected, her saw Evelyn, her head above the surface beaming happily at the second person in the pool. A girl. It was Lisa. As Tom watched, Lisa stood up in the shallow end and lazily untied the top of her bikini. She lifted it over her head and threw the garment at Evelyn, who jumped up and caught it. As she did so, her right tit came free from her own bikini top and Tom could see her dark nipple against the olive skin. His cock began to react.

Evelyn followed the example of her young friend, and removed the restraining bikini top altogether and just let it sink to the floor of the pool. Then she kicked off and swam to her friend, and without pausing, sank under the surface and Tom could see her pulling the girl's pants down, and off. His cock was the first to react, followed by the girl who shrieked again in mock alarm as she stepped out of her bikini. The water was churning too much for Tom to get a clear view, but it was obvious that Evelyn had removed her own pants and she was now rolling them into a ball. She swam up behind Lisa who was standing in the shallow end, nakedly exposed from the waist up, and rising up behind her, Evelyn placed her bikini pants into the mouth of the girl in the pool with her.

Tom fully expected Lisa to simply take them out of her mouth, but she didn't. Instead, she waded to the poolside opposite Tom and pulled herself half out of the water, laying her chest on the tiles and exposing her bottom, with her legs trailing in the water behind her. Tom couldn't help but notice the marks on the girl's buttocks. A good dozen or more bright red stripes across each cheek. Lisa has been caned, he realized, and obviously very recently. His cock was fully engorged and he just had to drop his shorts and start playing with it.

Evelyn approached the girl and with her back now to Tom, gave the girl six hard slaps on each buttock. The sound of wet hand spanking wet bottom carried to Tom and his cock almost exploded. He had to stop stroking it to prevent himself from cumming too soon. He knew there was more to see, and he was right. The girl rolled over onto her back and brought her ankles round the back of Evelyn's neck, drawing her face down towards her pussy. There was no resistance from Evelyn and within moments, she was feasting on the girl's cunt. The howls and shrieks of pleasure were dimmed by the bikini gag the girl had in her mouth, and knowing that in her current position, Evelyn had no way of seeing him, Tom stood up and opened the window a further twelve inches or so. He wanked furiously, spraying his load into the garden below once again.

At this, the girl tapped Evelyn on the shoulder. Evelyn immediately rose up and turned her head to watch Tom as he squeezed out the last drops. He couldn't help himself if he tried. Evelyn moved to one side and Tom got a view directly of Lisa's highly aroused twat. As Evelyn turned he could see her thick, stiff nipples and he couldn't drag his eyes away from the delights he was seeing. He knew he was caught again. Evelyn waded across the pool, looking at Tom the whole time, and rose up the ladder of the pool. She stood, stark naked, with her hands on her hips and looked up at him. He could see the swollen pussy lips, completely without hair as he stared out of the window at the goddess.

She didn't have to raise her voice. "Well, Tom. Not just a nasty spying boy, but one so foolish as to repeat the exact offense which earned him six strokes of the cane. I think you had better come down here, Tom, and apologise to Lisa and me."

Hastily, Tom donned his lightweight shorts, forgetting completely to put on underwear, and went downstairs. He hopped over the wall and sheepishly stood with his hands grasped in front of him, and his eyes down.

"I'm sorry, Miss. I just couldn't help myself from watching you with Lisa." He looked over at the girl, who was still naked. And she was a beauty too. Thick, dark blonde hair with a fringe, but only shoulder length so her boobs were exposed completely. Neither large nor small, they clung to her chest forming lovely curves that Tom would love to hold but experience told him he couldn't. Strong nipples, a deep coral tone, pointing slightly upwards. Slim waist and curvy hips, and once again, a totally shaved pubis highlighting the thick, aroused outer lips of her pussy. She had removed the cloth from her mouth and was standing unashamed, looking at this boy who had so easily fallen into their trap.

"Tom, once again, you meet Lily. As you know to your cost, Lily is my very dear friend who visits me once every month. As you will have noticed, I like to cane her, Tom. And as you may have guessed, she likes me doing that to her. She tells me that she is proud to carry the marks of her Mistress's caning for the whole month, and begs me to cane her extremely hard to ensure that she is sufficiently marked to last her until the next time. We were mid-way through her session when we decided to have a swim. And now you have found us out Tom, again!"

Tom was massively turned on, and was delighted, yet embarrassed, that his cock was already recovering from its recent emptying. It was already half hard and he simpered a "Hello, Lily. Nice to see you again."

"Hello, Tom." Lily replied. "Nice to see you too. And to see you behaving as badly as ever. Your friends down at my massage parlour miss you, Tom, as do I, but I quite understand that our games together weren't to your liking. No hard feelings, Tom." She turned to Evelyn, "But Mistress, here we are naked and Tom is not. That doesn't seem fair." And without waiting, she approached tom and placed Evelyn's bikini pants over his head, effectively blindfolding him. His dick sprang to full attention as he felt her thumbs on the waistband of his shorts and drew them down to his ankles. He stepped out of them, mortified at now being exposed to two women at once. His two mistresses. But all that talk of caning had done for him and he knew it wouldn't be long before he was taking another himself.

"Lily has requested a further eighteen strokes of the cane, Tom. Would you like to watch me administer them?" Tom heard Evelyn's voice.

His erection swelled a little more and he stammered that he would like that very much. He was taken by the elbow and led into the house. He knew the layout and even before the door closed, the silence told him that he was in the Punishment Room.

His eyes were uncovered and the naked boy was ordered into the corner where he would not get in anybody's way. He could watch, they told him, because Lily wanted to watch him take his punishment too. His thumping hard-on was testimony that he wasn't averse to that idea.

"Mistress. You have already given me eighteen strokes of the cane, and now that we have had a swim, my ass has cooled down again. I know that when you give me the next eighteen strokes, it will be without warm-up and on top of the strokes I have already taken, it will be painful. However, I beg for no mercy. Please cane me very hard, Mistress."

"Are you sure, Lily? You know that I will do as you request, but we have never before broken off for a swim mid-caning. It really will hurt. A lot. And you know the rules; you must take your caning in complete silence. Any sound from your vocal cords will result in the stroke being repeated at the end of your requested eighteen. For extra strokes, you may scream as loudly as you like, knowing as we all do, that nobody will come to your rescue and that once I have you secured, you will only be released when I say so.

"Yes, Mistress. I know the rules and I accept them. Please tie me down securely. I will try to take my caning in silence."

Tom could barely believe his ears. This beautiful girl, his own previous mistress, was begging for a severe caning, and now she was climbing up onto the chair arms, spreading her knees wide and he could see her anus and her gaping pussy. Oh god, how he would love to bury his face in amongst that.

Tom couldn't believe his eyes this time, as Evelyn laid stroke upon stroke on poor Lily's buttocks. The lines turning a fiery red, and where they were now landing on previously caned skin, a dark blue. Evelyn caned her supplicant very hard, but Lily was made of stern stuff and it took until the thirteenth stroke for her gasps and wheezes and massive inhalations to become vocal.

"Ohhhhh!" she moaned as another strike resonated within the room. And then her apology. "I'm sorry Mistress. Please add another stroke."

In all, Lily begged for five more strokes.

"These additional strokes will be inflicted extremely hard, Tom. Are you able to watch, or would you prefer to leave the room? I am going to make Lily do three things: I am going to make her scream. I am going to make her cry. And I am going to make her beg me to do that. I repeat, do you want to stay or leave?"

Tom had been gently stroking his erection and was very horny. "Please may I stay, Mistress, if Lily doesn't mind?" a considerate thought.

"Stay, Tom. I want you to watch me as Mistress beats me. It adds to my humiliation, knowing that you are playing with yourself as you watch me suffer."

Luckily for Tom, he didn't cum as he listened to the whistling of the cane, the gasps and shrieks of the securely bound naked girl, her stifled sobs and finally, as the last stroke landed a loud scream of ecstasy as the girl climaxed, and he watched in amazement as her asshole clenched and opened in quick succession as the powerful orgasm took her. Lucky, because it is easier to take the pain of a caning with pent up horniness still unfulfilled and it was his turn next.

Lily was given a full ten minutes to recover from her ordeal while Tom was secured into the now familiar position on the chair. He waited quietly and submissively until with a smile, Lily rose from the chaise longue that she had been lying on, front down to air her burning buttocks, and announced that she was now ready to administer Tom's caning.

Tom was surprised. He was expecting Evelyn to enact the punishment. Sensibly, he said nothing, accepting whatever they were going to do with him was well-deserved.

"Well then, Tom. You just watched me taking eighteen strokes of the cane. Now it is your turn." Lily told him as she led him to the caning chair. "You know the position. Get into place." she continued.

As he already knew from previous experience, Lily was not as strong as Evelyn and he was comfortably able to take his caning without much challenge. His buttocks were well striped, but he knew he would recover quickly. He thanked Lisa, and Evelyn, apologized for his behaviour and promised never to repeat his offence. Nobody believed him, but the summer was drawing to a close and perhaps the pool would be less used for many months. He was sent home with instruction to report his misdemeanour to his mother and show her the evidence of his punishment. She would know what that meant - as Tom had discovered. Whenever Tom was punished by Evelyn, Andrea was obliged to request a similar punishment. Tom had just earned his mother a caning of eighteen strokes.

But Andrea was not the next visitor to Evelyn's Punishment Room.

"Hello. This is Evelyn." responding to the ringing phone.

"Good morning, Evelyn. This is Kay. Do you remember me? Amelia's mother. We met at Andrea's house about a month ago."

At last, Evelyn thought to herself. I thought maybe she wouldn't have the courage to contact me.

"Yes, Kay, of course I remember you. Amelia reported herself to me just last week, as you know perfectly well. What can I do for you, Kay? Is that why you are calling? Is she alright?"

"Oh, yes. She is absolutely fine. Her behaviour is so much better now; very clearly that is something I must thank you for. We talked about her last visit to you when she got home, and she even showed me her bottom. She seemed quite proud that she had taken such a hard beating from you."

"Indeed. She had a reasonable warm up with the paddle, and that will have made it easier for her to accept the caning she received. But is this what you want to discuss with me now, or did you have something else you wished to discuss, Kay?"

A pause, a slight gulp, and then "Yes, you're right. There was something. I know Andrea has spoken with you about my interest in revisiting a particular aspect from my schooldays. She even mentioned to me that you wondered if I would like you to wear a gown and mortarboard."

"I remember the conversation. Is this the 'something' you want to discuss? Have you been a naughty girl, Kay?"

"I'm afraid I have. I got caught in the showers with my friend a few days ago. I was soaping her all over and someone from the tennis club committee walked in and found us out. Of course, it isn't against the rules, but now she knows about my friend and me and I feel responsible. The same thing happened at school one day and I was punished for it then by the headmistress. I expect I should be punished for it now, not having learned my lesson."

Evelyn smiled triumphantly. She adopted her serious voice.

"Of course you should. You have tainted your friend's reputation. That is rather serious a matter. I am glad you have brought it to my attention. Of course, by confessing, you may think the punishment will be reduced."

"Well, I hadn't considered that, Evelyn, and I'm pretty sure it won't help at all. Actually, when we are talking about things like this, I'm not sure what I should call you. I've been out of school for almost twenty years and it doesn't feel right to call you 'headmistress', but I want to address you with a more formal title than your name. What would you like me to call you?"

"You will refer to me as 'Mistress' when you place yourself under my authority, as you are doing now."

"Yes, Mistress. I like that. Thank you. I get a thrilling feeling of submission when I call you Mistress. So, Mistress, I have committed a serious misdemeanour and I know I must face the consequences. I respectfully request that you take charge of me in this matter and deal with me as you see fit."

"Very well, Kay. I will give you three days to reconsider your request. If you change your mind, please let me know. Otherwise, you will report to my house at exactly six o'clock on Friday evening. Prepare yourself properly. I think you must already know my requirements when people report for discipline: you will be clean, completely shaved and punctual. Failure in any one of these rules will result in immediate dismissal."

"Yes, Mistress. Thank you, Mistress. I will ring your bell at six on Friday evening as instructed. Goodbye now."

Well done, Tom, thought Evelyn. First you come to me for a caning, and from that encounter, you have increased my stable by a further three willing submissives - your mother, her friend and her friend's daughter. She chuckled happily.

There was no phonecall, and Evelyn was looking forward to trying out her newly acquired item of furniture on her new supplicant. On Thursday afternoon it had arrived and been placed in her Punishment Room. In the shape of a kneeling person, the caning bench had a sturdy, wooden frame with two widely separated supports for the legs to kneel on and leather straps to hold the ankles and calves in place, further straps for the thighs and an adjustable surface for the torso to lie on. The highest part of the body would be the victim's buttocks as the bench angled down with more straps to hold the chest down. Cuffs for the wrists completed the restraints. Once in this bondage, there would be no escape, the position rendering a naked submissive's genital area completely spread open and exposed for inspection from behind.

As her clock began to chime the hour, the doorbell rang. Kay was reporting for punishment. She was invited in and taken first to the living room for a chat.

"Welcome, Kay. Are you nervous?" Evelyn could read the signs.

"Good evening, Mistress." Kay remembered her role. "Yes, I am quite nervous. I haven't done this before and school was a long time ago. Also, at school, I had no choice. I had to do what I was told and obey the teachers. Today, I am here through my own choice, but I don't really know what will happen, and whether I am making a terrible mistake turning fantasy into reality." Quite a speech, but it was a prepared one.

"And I assume you have followed my instructions carefully. You were on time, and I can detect that you are freshly showered."

"Yes, Mistress. I think you will find I have obeyed the other instruction too. I may be nervous, but I don't want to be dismissed."

"Good. Now, I am sure you have discussed where you are with Amelia, and most likely with Andrea. Am I right?"

"Actually, I'm going round to Andrea's for dinner after I leave here. She knows what I am doing. I thought I would tell Amelia afterwards."

"Fair enough. Now. This is your last chance. Do you wish to withdraw your confession? You can stand up and leave here now without repercussion. However, if you choose to stay, you will be giving me full authority to treat you as harshly as I believe the situation demands. So, you may stand and go, or you may crawl over to me on your hands and knees and beg me to punish you for your appalling behaviour in the showers."

Kay was truly in two minds and her courage was failing her. As she stood up though, she gave way to her deep needs and sank to her knees. She crawled across the carpet and approached her mistress.

"Mistress. I have been a very bad girl and I was caught playing sexually with a friend in the showers. I know I deserve punishment and I beg you to administer it now."

"Follow me to the Punishment Room, Kay, where I will inform you what I intend to do about your actions."

Kay had not seen the room before, and was struck by how ordinary it looked, other than the strange item of furniture dominating one wall. She rose to her feet and began to remove her clothing. Evelyn had informed her that she would receive her punishment naked and she already knew that from her conversations with Andrea and her own daughter.

"You will be naked, and I will inspect you intimately for pubic hair. If I find any, your punishment will be doubled." Her mistress watched as the dress and shoes came off. Then the bra, exposing her glorious, still firm 36C breasts with their strong dark nipples hardening as the cool air struck them. Finally, her sensible cotton panties were folded on top of the pile of her clothes and she turned to face her mistress.

"Hands behind your neck. Elbows back. Feet apart, wider, wider! This is the punishment position. You will adopt it whenever you are under my authority. Do you understand?"

"Yes, Mistress. Thank you, Mistress." Kay bleated out. She was accustomed to being naked in front of a woman. Relished it in fact. But this was different. She was about to be punished and she didn't yet know how much and with what.

Evelyn watched the expression on her submissive's face as she passed sentence. It pleased her to see fear in it. The slave, for that is what she will become, will suffer this evening, she decided, but not as badly as she expects. I do want her to come back after all.

"Kay, you have led your friend into disrepute. For this you will be caned. I propose to give you twenty-four strokes with no warm-up. I now offer you a choice. Would you like to take your caning in silence, or would you like to count the strokes aloud, thank me and beg for the next one?"