Tom's Journey into Submission Pt. 02

"Oh dear, Mistress. That last burst got the better of me. I'm so sorry." She said, noticing the wet marks from her spillage spreading towards the circle on the sheet.

They both watched as the stain spread further. Andrea had not managed to keep it all and there was plenty of liquid saturating the sheet.

"Six strokes are guaranteed, slave. Let us watch as the wetness spreads. I fear you may be in for the full two dozen. Is that what you wanted, Andrea, to swallow half a litre of my pee before I cane you twenty-four strokes? I do hope so, because I can see the sheet cannot contain all that you spilled within the ring. See, there, and there, the line has been crossed, slave!"

'Yes, Mistress. Thank you, Mistress. I'm sorry I failed to drink all of your nectar. I fully deserve the caning you are going to give me."

After a shower, and a naked dip in the pool together with her mistress, Andrea was invited back into the Punishment Room to submit to her punishment.

"Every time I come here, I get a higher number of strokes, Mistress. First just six, then eighteen and now twenty-four. Is this a pattern that is going to continue, or will you sometimes give me fewer than a previous visit?"

"Which would you prefer, Andrea?"

"Actually, you once mentioned your slave, Lily, who took more than a hundred strokes from you. If you keep increasing my punishment, I guess I could end up taking the same. The notion scares me, yet I know that is where I am headed. I cannot say, of course Mistress, but if you decide that I must take ever increasing numbers, then I will submit to your wish." Secretly Andrea wanted this to happen but didn't have the courage to request it herself. Like a good submissive, she awaited her mistress's judgement.

"Then we shall see, little kitten. Time will tell. But today, you can expect twenty-four testing strokes. You no longer have to follow your son's preamble; you are now disconnected from his visits here."

* * *

Tom's shift at the supermarket was finished early and he went home to take a shower and cleanse his cage and the contents therein. He went back downstairs, casually dressed in just shorts and a tee shirt and turned on the TV to watch Countdown. He fancied the clever girl who did the numbers and enjoyed the letter and number games, although he was seldom as good as the contestants, he found he was learning a lot from them.

The doorbell rang and he went to answer it. On opening the door, he was met with a stunning sight. It was a beautiful girl. A girl with short, dark-blonde straight hair with a fringe barely covering her deep blue eyes. Snub nose and luscious lips. Around her neck was a chain with a key on it. Vaguely familiar, as was the girl. She was dressed in a diaphanous, pale yellow dress with matching blouse, and he could see her nipples through the thin fabric. She moved her feet, placing them curiously wide apart and Tom could see right through the material as the sun shone behind her. He could see the shape of her pussy lips, creating a W at the top of her thighs and he realized she wore no underwear at all. His cock swelled against its cage.

"Hello, Tom. Remember me? I'm the girl from your favourite video. Lily," she said, as she made her way past him and into the house.

"Of course, you didn't know my name, but I'm sure you've seen me dozens of times - haha, until recently. Well, I'm your fairy godmother. I've come to release you from your imprisonment."

Oh, my, god. She's gorgeous! Tom couldn't believe his eyes or his ears.

"But, you have to pass the tests first, otherwise you will stay as you are for a while yet. Is your mother at home?"

He was nonplussed by the question. "I think so. Maybe up in her room, resting. She said she had a hard day yesterday and needed to lie down."

"Then we can use the living room." Spoke the girl with a laugh, knowing full well what kind of 'hard day' Andrea had endured. Twenty-four rather hard strokes. Her buns are going to be marked for a good two or three weeks, she thought, remembering the video she had watched earlier with Evelyn. "Show me the way."

In fact it was an open plan room, kitchen, dining and living room all in one, with lots of light coming through the large windows which faced the back of the house.

"No nosy neighbours then? Eh, Tom? I've heard there are some of those in the area."

"Er, yes. Lily, did you say? I'm delighted to meet you, Lily. But why are you here?"

"I've already told you, silly boy. First there are some challenges, and if you pass them, I have the key to what you want more than anything else in the world right now. I have the key to your cage, Tom. I can unlock it and release your cock and your balls back into the wild! Wouldn't you like that? Mistress Evelyn told me you would be thrilled."

Tom gawked at her and his mouth opened and closed like a fish. He was wordless.

"Or if you prefer, I'll go back and report to her that you don't want to be freed." Lily made a pout with her lips.

"No, no, don't do that. Please let me out. What can I do? What are these challenges?" He begged her, finally having realized what was happening.

"Well, the first one is to remove your clothing, Tom. Naked. You. Now!"

"What? Here? In the living room? What if my mum comes in?" His eyes widened and he stared at the girl. Well, not exactly at her, but he was furtively wanting to see her nipples and her pussy more clearly.

"That won't be my problem, Tom. Now, obey challenge number one immediately or you fail and I walk out of here."

Tom accepted his fate. Mum has seen it all before anyway, he reasoned, and knows everything about this. He tugged his tee shirt off and dropped his shorts. No pants, quickly naked.

"Punishment position!" he was commanded and rapidly spread his feet and held his hands behind his neck.

The girl, no - goddess, Tom decided, approached him, amused smile on her face as she gazed at the metal cage. She knelt down and probed with her small fingers, testing to see if Tom's skin was damaged by the constant friction, but she deemed it well looked after.

A young man's favourite toy, she smiled to herself. Of course he'll do everything he can to keep it in good order. She opened the canvass bag she had brought with her and showed Tom what appeared to be a small version of a horse's tail, the strands of hair about two feet in length. She was holding it by the handle.

"A.. are you going to whip me with that?" Tom asked nervously, not knowing what the girl could do, but recalling from the video what she could take.

"Would you like me to, Tom? Would you like that to be one of the challenges?" she retorted, clearly enjoying herself.

Maybe that's one of the challenges itself, he thought. If I say no, I fail.

'Yes, please, Miss Lisa. Please whip me with that." And without being told to, he placed himself on the arms of his own easy chair, knees apart, just as he would in Mistress Evelyn's Punishment Room.

"My, my, what an obedient boy. And what a willing slave. A punishment slut too. Lovely!" she taunted the naked boy.

"How many times shall I thrash you with this whip, slave Tom?" she offered no choices. Tom went with his previous caning.

"Eighteen times, Please Miss Lisa." He appealed.

"When a slave is begging for a whipping, he calls the lady who will provide it 'Mistress' foolish boy. My name to you is Mistress Lisa." She sounded menacing.

Yes, Mistress Lisa. Sorry, Mistress Lisa. Please give me eighteen strikes with your whip." More contrite now.

Lisa started, and paused at stroke nine. "Why are you not counting and thanking me, slave? We will start again!"

Just then, a slight sound alerted her to someone else's presence. The door to the hall eased open and Andrea stood at the entrance, slightly dazed after awakening from her siesta and slow to recognize what was happening in her own home. Slowly she recognized Lisa from her photos and deducted what was taking place

Lisa motioned her to silence. Once again, removing an item from her bag, she placed a blindfold over Tom's eyes. Now, unless she spoke, Tom would not be aware he was being witnessed by his mother as he took his punishment. He lowered his back and presented his bottom more proudly to take the beating.

In fact, the horsehair didn't hurt at all. It simply stung a little but it was too light to do more than stimulate a slight blood flow to the region. Unfortunately for Tom, this included his cock and it strained against its constraints.

Andrea watched in stupored silence as her son gave himself up to the whipping. When it was done, he thanked Lisa politely.

"Would you like more of this whip, Tom?" Lisa asked sweetly, knowing what his response must be.

"Oh, yes please, Mistress Lisa."

She laughed delightedly. "I wonder if you will regret saying that, Tom. Now - I forbid you from moving. Move or break silence and you will fail this challenge. Do you understand?"

Tom wasn't sure if he was allowed to speak.

"You may answer, slave."

"Yes, Mistress. I understand. No moving, no sound."

Once again, Lisa reached into her bag, withdrawing two items this time. a condom and a tube of KY jelly. Reversing her grip, the handle of the whip was now visible and Lisa showed it gleefully to Andrea, who was a little shocked and hugely turned on. The handle was a replica of a penis. A medium-sized and not too thick erect penis, with grooves and veins and a ridged head, the length slightly shortened by a deep groove around it about seven inches down the shaft. The dildo was made of a squeezable rubber material and Lisa rolled the condom over the length of it. She then used the tube of jelly to slather the dildo and finally squeezed a liberal amount directly onto Tom's young virgin anus.

He stifled a cry as he instinctively tried to draw away from the unexpected intruder, but Lisa cooed at him and settled him back in position. He was still blindfolded and Lisa beckoned Andrea closer as she started to ease the rubber penis into Tom's resistant ass. Resistant for not too long as she expertly thrust gently in and out, easing the opening until with a shiver and gasp, Tom's anus allowed the head of the dildo past the sphincter and with a well lubed rush a full four inches slid into him, out of sight.

"I'm fucking your ass, boy." Lisa crowed "Do you like it. Do you want it deeper? Do you want it in all the way to the balls, slave boy?" as the dildo glided easily in and out.

"Yes, Mistress Lisa. Please fuck my ass as deep as you can go. This is great. I love the sensation. Fuck me. Fuck me, please."

Lisa used one hand to lift Tom's blindfold as she slid the dildo home and Tom's anus tightened against the narrower groove, holding it in place. Tom looked around to see his tormentress as Lisa came round to face him. Andrea was dripping juices from her pussy and trying hard to manage them as she had not donned any underwear.

"Thank you, Mistress. That was incredible. And I guess it still is."

"Well done, Tom. You have passed the tests." Lisa removed the chain from her neck and handed it behind Tom with an assertive nod and gesture. He kept looking at her devotedly until he felt hands at his cage.

"Wha.. what? There's someone else here?" He looked around in alarm and was mortified to find his mother behind him, fiddling with the lock on his cage. He could also see in the mirror behind her the reflection of himself, kneeling on the chair with what appeared to be a horse's tail sprouting from his backside. Oh, god. I'm a horse's ass!

"Oh, my god!" he cried, closing his eyes in the hope that it wasn't true. But he daren't move yet, and his mother's hands turned the key in the lock. He felt a slight release of pressure there.

"Stand, slave. Punishment position. Now!" Lisa's commands brooked no disobedience, for all the humiliation he felt at his mother having witnessed such debasement.

It was Lisa who removed the cage, gently, with more use of the lubricating jelly, and then slowly, gently fed first one testicle through the base ring, then the other, and finally drew the ring off his cock. One might imagine that after two weeks of not being able to erect, a cock might be reluctant to grow, but Lisa's hands rubbed and massaged life into Tom's and within moments he was standing there shamefully exposing his hard-on to his mother and proudly so to his Mistress Lisa, who he now loved almost as much as Mistress Evelyn, and both of them possibly more than his mother!

Lisa rolled a condom over his erection and one hand returned to the dildo with which she resumed fucking him while the other hand stroked and stimulated his cock.

"You have one final task, Tom. I hope you are hungry, because you are going to eat whatever is in the condom two minutes from now. Hold your cum, and there will be nothing to eat. Spray your cum into the condom and you will eat it all. Your time starts now."

Tom was aghast. He'd never tasted cum before and didn't want to start today, but the goddess Lisa was so beautiful and the angle he could see her at right now was enough to see her left tit perfectly with its dark pink nipple sticking out like a pencil rubber.

"There's a good cum slut. I want to see how big an ejaculation you can give me." Lisa taunted him as she fucked his ass and worked his cock with her hands.

I want to see a huge orgasm, Tom, and I want to see you eat it." she continued and expert as she was, she made him last out until almost the last moment.

"And if you please me, Tom, and eat your cum like a good boy, maybe I'll make you eat the cum of my ladyboy friends. You're a pretty boy, Tom, and I know they would like me to watch you to eat their cum too!"

It was too much for Tom. Never good at holding back anyway, the double stimulation from her hands and the sultry sound of her voice, he barely heard the words as he gave in to the best orgasm he could remember ever. It might well have equaled or even exceeded the quantity he had put into the sheets several days ago. It just kept pumping, at least a dozen times until a cooing and aaahing Lisa finally squeezed the last drop out of him.

"Oh, what a good boy. One minute and fifty-seven seconds. Imagine Tom, if you had held out for just four seconds more, you would have deprived me of such pleasure. But you didn't, so your mother and I will now watch as you drink it all down. Would you like me to transfer it into a glass first?"

Tom was revolted at the thought of eating it at all, but the thought of doing so out of the condom was even worse.

"Please can you put it in a glass, Mistress?" Andrea fetched a sherry glass and Lisa poured the contents of the condom into it. It seemed to be half full.

"Drink, swill and swallow, Slave. If you do it well, I may be kinder to you with my offer of ladyboys." Lisa grinned cruelly. She could see that Tom's young cock was thickening again already after her gentle stimulation, and both Mistress and mother watched in astonishment as Tom developed another strong, throbbing erection.

He wasn't going to admit it to his mother, but some of his research into the porn sites had fallen upon the topic of ladyboys and he had fantasised frequently in the past year about some of those South American beauties and the ones from the Far East with their huge cocks and their large breasts.

His immediate revulsion at the reality of having to eat his own cum was replaced with the thrill of humiliation of doing this in front of his new goddess and his mother, and as he swilled his cum, he imagined his mouth filled to overflowing with multiple ladyboy cocks spurting all over his face. His erection throbbed happily, free at last.

To be continued.