Tom's Journey into Submission

A young man falls prey to his attractive neighbour's dominance, as does his mother.

"What on earth did you think would happen?" The foolish boy's neighbour looked down on him as he hung his head, embarrassed at having been caught. She, at five foot ten, stood a good three inches taller than the young man who lived next door with his mother.

"I'm sorry, Miss Steen. I couldn't help myself. You just looked so beautiful, lying out there by your pool. I just wanted to see more closely."

Indeed he had. Saturday afternoon and his mother was out with friends at the local sports club, having left her 18-year-old son in his room, listening to music and surfing the net. He had heard the splash from across the wall and peeked out of his window. He had noticed her before, of course, and even run some errands for her over the past few months since she had moved in next door, but this was special. She was wearing a small bikini, actually a very small, silver bikini and he had watched in admiration as the athletic looking woman, just twice his age and looking ten years younger, swam some lengths of her outdoor pool.

The costume had loosened as she dived in, but she didn't mind that. It was nice to liberate the tits in the pool and as she returned to the shallow end she stood up and removed it altogether. She thought she noticed movement in the half-open upstairs window of the house opposite but she had heard their car leaving twenty minutes ago so believed the house to be empty.

She continued her exercise, a few more lengths and then rolled over to swim on her back for the final four lengths. She saw it again, the curtain twitched and there he was, half a face peering out from behind. The little sod is spying on me, she thought, and here I am with my tits out.

The spider began to spin her web.

Leaving her discarded top at the bottom of the pool, she glided to the edge nearest the watching boy and stood up again, shaking her head to disperse the water, climbed up the ladder and out of the pool.

Her 36C boobs stood out proudly, the nipples long and stiff with the cool breeze on them, and made a show of pulling her bikini pants up very tightly into her crotch. There was so little cloth, and she pulled it so tight, it disappeared into the crack of her pussy and stuck there. That should get a reaction, she thought, and went over to her recliner and lay in the sun on her back, her boobs basking in the fresh air.

Tom was thrilled. His gorgeous neighbor had never gone so far before. She really was a stunner with her tall frame so perfectly proportioned, glistening, thick raven hair and olive skin, and now as good as naked. I can't see any hair there. Does she shave it, he wondered? Tom did what all eighteen-year-olds would do; he dropped his pants and masturbated furiously. Like an idiot, his window was raised open and just as he began to cum, he approached the window and sprayed his load straight through the open space and into his garden below. Unfortunately, just as he was doing this, Evelyn Steen opened her eyes, spotted the boy and sat up, gazing at him in mid-spurt. She put on an outraged expression and stood up, looking at him and shouted out:

"You horrible boy! Come down here this instant!"

Tom knew he couldn't deny any part of what he had done. It was a fair cop, and now he stood before his neighbour, hands clasped in front of him and eyes down in shame as he continued his confession.

"I don't have a girlfriend, Miss, so I haven't seen a girl with so few clothes on." He knew the hole he was digging was getting deeper.

"Does your mother know you do this kind of thing? Spying on your neighbours and performing disgusting acts of lewdness in front of them?"

'Oh, please no. Please don't tell my mum, Miss. I'm already on my last chance with her. Please don't tell her."

Gotcha! Miss Steen took a long deep inhalation and drew herself up to her full height. This didn't help poor Tom, for although she had wrapped a silk gown around herself, her bikini top still lay in the depths of the pool and her nipples were aching with the fun she was having. They were very obvious under the thin material and whenever Tom looked up at her, his eyes could rise no higher than those nipples.

"So, you agree that what you did was wrong? Disgraceful, even?" she asked, more quietly and controlled this time.

"Yes, Miss Steen. I know it was bad and I shouldn't have done that. I really am sorry. What can I do to make it up to you?" Tom was contrite, knowing exactly what would happen if his mother ever found out about this.

"Tell me, what would your mother do with you if I report you to her? Let there be no misunderstanding, I believe that would be the right thing to do." Teasing it out of him little by little.

"Well, she hasn't done it since I turned eighteen, but she used to give me a very hard spanking, and she would probably take away my mobile and laptop for a month." Stupid boy, shouldn't offer more than the basics.

"A spanking? With her hand?" Evelyn's eyebrows rose as she spoke.

"Yes, Miss. For starters, and then she might use a paddle or sometimes a cane. But for me that wouldn't be the worst of it. I really like having my phone and I don't think I could survive without my computer for a month."

Now we're getting somewhere. Evelyn's face gave nothing away though.

"So, what would you expect me to do, if I were to keep this between ourselves?" she inquired.

"I'm not sure Miss. I'll do anything you say, if you just don't tell mum."

"So, you agree you need to be punished? Are you asking me to punish you, Tom" she almost smiled.

"I suppose I am, Miss, yes."

"Then, don't you think you should ask me politely to do just that?" trying not to smirk.

"I'm sorry I stared at you, Miss. Would you please punish me for it." He tried, but not well enough for the beauty in front of him.

"You did more than just look at me though, Tom, didn't you? What disgusting act did you force me to watch?" almost laughing out loud now.

Oh, god. This is humiliating, thought Tom. "I, er, got excited and I wanked through my window and you caught me doing it, Miss. I'm sorry, and I know I should be punished for that too."

"Indeed you should. And what would you like me to use to punish you with, young man? My hand, a paddle? The cane perhaps, like your mother would use? Would you like me to do that to you, Tom? Would you like me to cane you?"

Tom's cock was young, and it was beginning to recover fully from its recent abuse. He could feel it stirring inside his shorts. Like a fool, he was wearing just some loose nylon shorts over his underwear and neither was strong enough to withstand the pressure of his growing dick. He knew that, and he eyed Miss Steen fearfully to see if she had noticed too. Then he looked aside and into the pool where he saw the small silver bikini top under the surface. He knew her breasts must be naked under that gown and this was enough for his dick to come to full erection. That coupled with the mental image of this beautiful woman standing over a naked Tom with cane, laying strokes across his backside.

"Yes, please, Miss Steen. Would you please cane me as punishment for staring at you while you sunbathed and for what I did after that?"

"Very well, Tom. And now that you plead with me to use my cane on you, how many strokes would you like me to give you?" Her eyes were dancing. She could see the boy had another raging hard-on and he was about to beg for a caning. This has been a marvellous afternoon, she mused.

"Oh, Miss. The most I ever got from my mum was six. That would teach me my lesson, I'm sure, Miss."

Evelyn Steen was an interesting woman, with rather a scarlet past, and one thing she knew a lot about was applying a caning. She even had all the necessary equipment in her carefully decorated study, which would raise no suspicion from anyone unused to such practices. And a tall Chinese vase, well supplied with canes and other instruments of correction hiding in a cupboard.

"Well, as the only window overlooking my swimming pool is yours, and you are here with me, there is nobody to observe as you prepare for your punishment. First, you will fetch my bikini top from the pool. You may swim down for it." She instructed.

"But Miss, I don't have my swimming trunks." Tom tried.

"I can see that. You will remove your clothing to enter my pool. You will be naked in a minute anyway, to receive your beating. You know that naughty boys must take their caning on the bare bottom, don't you, Tom?" This is great, she congratulated herself.

"Naked? You want me to be naked? I didn't know that, Miss. I'm not so sure now." But his cock was throbbing and he knew he would be submitting soon enough. Token resistance.

"You have ten seconds to comply, or I shall revert to my original intention. I will call round this evening to give your mother a full report of what I have witnessed today."

Tom ripped off his shirt and quickly dropped his pants. He was about to turn and dive into the pool when Evelyn commanded "Halt!"

He paused. "Face me, with your hands behind your neck!" Evelyn ordered. He knew he had no choice. He obeyed, giving her the full frontal, throbbing cock, tight balls and red face. An average cock, not more than six inches long but quite thick, she observed, with the foreskin completely drawn back and the purple head straining in its skin to grow even larger, if it only could.

"Does the idea of taking a caning from me excite you, Tom? As much as seeing me half naked on my lounger?" she asked sweetly. "Is the knowledge that you about to be caned by me causing you an erection? Or is it perhaps the idea that you are exposing your erection to me that helps to make it hard? Are you an exhibitionist, Tom?"

With that, expecting no reply anyway, she slapped his arse and sent him into the water to retrieve her top. He emerged, dripping wet and she handed him her towel in exchange for the flimsy bikini top. His erection should have been dying but he had never been so turned on in his life. He followed her into her house, to her study, in the centre of the house with no windows. She closed the door and a curious silence filled the room. "Soundproofed, Tom, especially for occasions such as this!" she explained.

She took the towel from him and without being told to, he stood once again with his hands behind his neck, exposing himself shamelessly. He was getting into his role quickly but he feared the cane. He knew it would hurt. Bloody hell! In a soundproofed room? Christmas! But this is my fantasy. Christmas again.

She told him to climb up onto the easy chair, place his knees on the armrests and the top of his chest on the neck cushion which was unusually low. He found by doing this that his bottom was pushing backwards, yet raised, and with his knees so far apart, he had very little wriggle room.

"Arms down the sides of the chair, Tom!" and as he complied, she quickly snapped his wrists with some previously concealed Velcro straps attached within the frame of the chair. Another emerged from behind the neck pillow and his neck was secured. More at ankles and knees on the armrests, and he was immobilised, albeit strangely comfortable. His balls hung down below him and his asshole was obviously completely exposed, but his erection was still strong.

Tom thought back a month, to some pictures he had seen on a website he had been browsing. This is very familiar, he thought. The position I'm in and even the fabric and pattern of the chair. He hadn't taken much notice of the décor of the room, as the victim of the bondage in this instance was a girl, a lovely looking girl, and there were many red and black stripes across her buttocks. The lady who had administered the girl's punishment was mostly out of the picture, but it had definitely been a lady not a man who had caned the girl. Other photos from the same story showed the girls tears, suggesting the caning had been a hard one. Just like earlier today, Tom's cock had erupted as he gazed upon those pictures. And now, here he was, secured into position by this dominant woman just like that girl had been.

"You will now request your punishment, Tom. Beg me to beat you with this cane." Evelyn Steen commanded the bound boy.

"Yes, Miss. Please punish me with your cane, Miss. I behaved very badly and I would like you to punish me for it. Six strokes of the cane Miss, please." Tom's heart was racing and his face as red as it had ever been. Shame, humiliation in fact, he was naked in front of this goddess and she was about to realise one of his recent fantasies. It was never erotic when his mother had caned him, just punishment, but he had quietly crept upstairs to his room after the last time she had caned him and masturbated furiously, imagining just the scene he was now in.

His mind drifted and he could picture himself, as if he were standing behind the tightly secured subject on the chair, and it was no longer himself, but a lowly urchin about to be punished by his mistress. Tom's cock grew even harder as he heard the whistle of the cane, swooping down on his as yet unblemished arse cheeks.

Cracckkk. Ohhh, white lightning, a gasp of surprise, massive intake of breath and a long moan of pain. Tom tried to wriggle free from his bonds but he was held fast. Oh, god, another five like that. I can't bear it. That was harder than mum ever struck me.

Evelyn watched as the white line quickly turned red, perfectly placed and even across both buttocks. She smiled with satisfaction as her victim stoically took the first stroke without the usual shriek of dismay and horror that many of her subjects made upon the first stroke.

"You may count the strokes aloud, Tom. Thank me and request the next stroke." She instructed, wanting to test this young man. She had put on the bikini top and adjusted the pants, but otherwise she was dressed in no other clothing. She went behind the chair and inspected Tom's face closely. He gazed back at her and spoke quietly.

"That was one, Miss. Thank you for caning me. Please give me another stroke." Contrite and polite, she noted. It almost sounds rehearsed. I'll bet the little squirt watches this kind of thing on his computer. I wonder if he has ever come across the clips I have posted. When was the last one? Ah yes. Lilly. A month or so ago. What a sweet girl, and what lovely tears I gave her. I must get her back here soon she decided.

Crackkk. A second stroke, equal to the last in everything but location. This was parallel but an inch lower. Air sucked in through the teeth, gasp, moan, silence. What a good boy. No complaints or pleadings for mercy. No stupid declarations of never doing it again. He is taking this rather well, although I am being very lenient with him. He isn't accustomed to a serious beating. Not yet, anyway. Let's lure him in.

"Two Miss. Thank you. Please cane me again." Tom was playing his game well, viewing the action from above and behind, where his mind had taken him, and he now knew he could cope with this more easily than he had expected. Yes, it hurt a lot, but his first thought about not being able to take this was already fading as endorphins and imagination took over. Let her think I'm really suffering, he told himself, while in fact I'm actually beginning to like it. His throbbing hard-on the evidence that he was greatly stimulated by what was happening to him.

Why is my cock so hard? He wondered. It must be because I am so turned on by being forced to submit to this half naked beauty, allowed myself to be secured so that I can't escape the punishment and I'm loving the helplessness, submission and humiliation. That's me. He returned his mind to where he really was and took the final four strokes with a degree of relish, knowing that she was holding back on really hurting him. Oh sure, a caning always hurts, but this was not intolerable. I could have taken many more, and much harder he reasoned with himself. Maybe next time. If there is one. I'm sure there will be. Do I want a next time? I think I do. Oh god.

Evelyn released him from his bonds and he stood up, a little shakily, holding his hands in front of his now wilting dick.

"Thank you for my punishment, Miss Steen. I know I deserved it and I will try to behave better in future."

"You may get dressed again, Tom. And I hope this has been a sufficient lesson for you. On this occasion, I shall consider the matter concluded, but let me warn you, if there is any further reason to inflict discipline on you, I will show neither mercy nor restraint. You will receive at least double what I have meted out today. I am sure you would like to avoid that." And with that, Tom was dismissed.

Just as he was entering the house, his mother drove up, parked the car and jumped out. An athletic figure, she had played three sets of tennis with her girlfriends at the club. After their foursome, they had all taken a shower in the changing rooms. Andrea, Tom's mother, was an attractive brunette still a few years from forty and in great shape. She was proud that her 34" boobs were still as solid as they had been twenty years before and they were a source of interest for one of her friends too. She did not object when her close friend, Kay came up behind her in the shower and brought a soapy hand up her stomach to her right breast and soaped it thoroughly. Her nipple sprang to attention and it was clear to Kay that Andrea was enjoying the attentions being paid to her. Her other hand slid down to Andrea's upper thigh and then across to revel in the short pubic hair above her slit. Andrea let out a squeal, and then a moan of pleasure as Kay's fingers made their way amongst the lips of her pussy and rubbed her gently.

"A girl who has been playing tennis needs to clean herself well, don't you think, sweetie?" Kay whispered into Andrea's ear and met with a nod of agreement. Andrea bent over at the waist and Kay's right hand moved to washing her friend's ass, soapy fingers sliding down the crack and over Andrea's anus, fingers delving towards the outer and then inner lips of this succulent pussy, now sliding her two middle fingers into the aroused hole as her thumb rested against Andrea's anus.

"Do you want it?" She whispered, and Andrea gasped yes, she wanted it. "Where do you want it?" Kay whispered.

"In my ass. Please Kay, push your thumb into my ass." Kay slid her well lubricated thumb into Andrea's anus, meeting resistance at first, but then it broke past the tight sphincter and went full length into her friend's ass. A second hand came into play and stimulated the clitoris until moments later, Andrea came in a great, gushing squirt and her knees weakened as she slid to the ground, eyes glazed in joy. The shower kept playing water over the two women and the soap was washed away. A kiss and they toweled each other dry and dressed.

Afternoon tea on the verandah found the women discussing their children and how teenagers behaved so badly these days.

"My Amelia tests my patience half the time." complained Kay. "I don't know what to do with her. And she reminds me she is an adult now so I can't punish her, but she is so rude sometimes. I wish I could give her the spanking she deserves."

"Maybe you should tell her that next time she pushes you too far. I know I would probably have accepted more discipline from my mother. Tom spends whole days in his room. I guess he's looking at porn most of the time, or maybe spying on our new neighbor. She's a beauty and loves her swimming pool. Tom's room is the only window in our house overlooking the pool and she seems to have been in it every day this summer." added Andrea. "I've spotted her myself, in her tiny bikinis with her big lovely boobs. I'll bet she makes someone happy every day!" she smiled over at Kay.

"Well, maybe you should invite her over for coffee sometime and find out." Suggested Kay, never a jealous woman. "Maybe she could make you happy too!" she smiled thoughtfully.