Tom’s Journey into Submission Pt. 03 – BDSM


Tom’s journey into submission. Part 3

“Would you mind taking this cup to Evelyn, Amelia?” Andrea held the saucer towards her friend’s daughter.

The planned afternoon tea party was just beginning and Andrea was pouring four cups for Evelyn, Kay, Amelia and herself. Although she was pretty, Amelia certainly had not grown out of her ugly teenager’s mood and she huffed as she complied with the polite request.

“She’s got legs. She could get it herself.” She muttered, but loudly enough for the gathered ladies to hear.

“Amelia, that’s no way to speak to Andrea’s friend. I think you should apologise.” Kay was mortified at her daughter’s rudeness.

“Hmphh. Sorry.” came the response.

“Oh, that’s perfectly alright, Amelia,” purred Evelyn, looking her directly in the eye, “I used to be a teenager myself. I quite understand, although I learned the hard way how little adults respect most youngsters. It’s rather a shame, really. Young ladies just coming into their most lovely forms sometimes need guidance beyond what their parents can give them. Sometimes parents are too restrictive and don’t allow their offspring enough leeway to experiment with life’s adventures.”

Kay knew the plan. She had agreed completely with Andrea that Amelia might improve her methods with a little discipline from outside the house. Now the game was afoot.

The ladies chatted away lightly for thirty minutes or so while Amelia sulked. Then Evelyn stood up and looked out of the window into the garden.

“What a lovely garden, Andrea. Perhaps Amelia would like to join me for a stroll.” She spoke with sufficient authority that Amelia had no choice but to accept. Anyway, the atmosphere in the house was too strained and she wanted a change of air.

The two went out, through the glass doors and Evelyn closed them behind her as she followed Amelia, giving a knowing look back to Kay and Andrea. Then she joined Amelia and they could be seen walking around the garden, seemingly admiring the flowers and shrubs, Evelyn talking and Amelia listening. Her mother looked on anxiously and gave a little squeak as Amelia suddenly stopped and looked up at Evelyn with a surprised look on her face. Of course, the women in the house couldn’t hear what was being said.

Amelia spoke back and an animated conversation seemed to be taking place outside, arousing Andrea’s interest and piquing her curiosity. After a good ten minutes of discussion, Kay and Andrea watched in amazement as Amelia held her hands in front of her, lowered her head, nodded a few times, mouthed a reply, which Andrea lip-read as a ‘yes’, and without a look back into the house, she followed Evelyn around the side of the house on the path that led to the front.

“Well,” said Kay, “whatever she said, it seems to have worked on Amelia. I’ve never seen her looking so ashamed of herself. She was positively blushing as she left.”

Andrea looked over at Kay with a conspiratorial look and added, “I wonder how many cheeks will be reddened by Evelyn this afternoon!” and both women giggled like nervous schoolgirls.

Forty minutes later, the doorbell rang and the door opened, Evelyn letting herself in with Amelia walking stiffly after her. They made their way into the large living area as Andrea ushered them back in. Evelyn resumed the seat she had previously been occupying and sat comfortably, as if in wait for something.

Amelia looked slightly disheveled, her shoulder-length brown hair unbrushed and her clothing a little more rumpled than earlier. She didn’t take a seat. Instead, she went and stood in front of Andrea, looked down at the floor and said in a stuttering voice, “I’m so sorry I was rude to your friend earlier. It was unforgivable and I apologise for my bad behaviour.”

Before Andrea could react or respond, Amelia adopted the same position of penitence in front of her mother and spoke again. “Mum’ I’m sorry I have been so sulky and rude to you the past year. I want to apologise. I know I was being childish and selfish. I’ll try to make it up to you.”

Kay was as astonished as Andrea. “Well, thank you sweetheart. You know that I love you and just want the best for you. Let’s make a new start.” A very public expression of her love and concern for her daughter.

Amelia wasn’t finished. “I think everyone here can guess what’s just happened. I’ve been to Evelyn’s house where she demonstrated how she felt about my behaviour. Mum, if I displease you again, please tell Evelyn. She will know what to do about it. I know I will deserve it and I have agreed to be disciplined by her again whenever necessary.”

“Really, darling? You want to be sent to Evelyn’s house if you disappoint me?” Kay was amazed. She was also feeling the heat in her groin. This Mistress Evelyn must be really good, she wondered. To turn my disobedient, rude girl into an apologizing wreck who asks for more when she earns it? Wow!

“Yes, mum. If I let you down, I want you to report me to Mistr.., uh, Evelyn. I promise I will not object or refuse.”

“Well, I’m glad that’s all settled!” Evelyn stood up and made her excuses before leaving. Andrea took her to the door, giving Kay and her daughter a moment alone.

“I am truly impressed, Evelyn. Well done, and thank you. I’m sure Kay will be in touch with you herself soon. While you were away with Amelia she was telling me more about her schooldays and I know she misses them greatly.”

“Should I wear a gown and a mortarboard?” asked Evelyn with a smile. “I can if she would enjoy the role play.” And both women laughed at the idea, albeit knowing that Evelyn was serious.

Evelyn then told her that the girl had been quite a tough nut at first, but with a little soul searching, she had come round to the idea that some discipline would do her more good than harm and she had finally given herself willingly to the idea that she should be punished. There had been some token resistance to the notion of taking her punishment naked, but once again, good reasoning and persuasion got her out of her clothes and she had succumbed to the bondage chair as everyone eventually does. She had been made to request twenty-four swats of the leather paddle and by the end of it, there was visual and olfactory evidence that she had actually enjoyed it. Her pussy was dripping! But what a hairy pussy it was. She had been ordered to remove all of her pubic hair before she would be allowed to return to this room. Andrea was massively turned on at the wondered of it all. Lucky Evelyn. Smart Evelyn.

Andrea returned to her living room and found Kay standing giving her daughter a big hug as Amelia sobbed her heart out. Quietly leaving them alone, she went and sat on the stairs, thinking about what a strange afternoon it had been.

Ten minutes later, Kay came through and announced that it was time to go. She said Amelia was truly sorry and had even told her she was glad to have been corrected by Evelyn.

“She says it opened up her mind and made her really think about herself. She even admitted that although her buns were burning, she would accept more if she knew she deserved it. I’m now beginning to wonder if she enjoyed her visit to Evelyn’s house a little more than I thought she might.”

“Time will tell, Kay. My guess is she will be as good as an angel until the need for discipline kicks in again, and then she’ll do something contrived and silly in order to be sent for more. If she is anything like you and me, that is! Meanwhile, Evelyn says to please call her whenever you are ready to revisit your headmistress and she will gladly make time for you.”

* * *

Tom, meanwhile had fallen under the spell of Lisa and, with full blessing from Evelyn, was now under her command. He had been taken to report to Evelyn first, for her to inspect his genital area in case there was any lingering issue after so long in the cage, but healthy young skin and her good hygiene advice had kept him in good condition. He was compelled to request a farewell caning from Evelyn and once again, his buttocks were covered in stripes which he wore proudly for Lisa. However, she was as good as her promise and was now planning to take Tom to her special massage parlour.

It was her own establishment, in partnership with a Thai friend. The friend was a ladyboy as were many of the staff. It was on two floors and included about six rooms downstairs for more traditional massage, but upstairs was rather different. This was divided into just three large rooms accessed from a sizeable landing leading down the open stairway with wooden banister and balusters to the reception area of the parlour. It was therefore feasible from below to look up and see people on the landing, and down, to see where, the massage girls relaxed while they waited for clients. All the staff were mischievous though and Tom had no idea what was in store for him as he sat beside Lisa in her sports car, driving to his appointment one afternoon a few weeks later. He had, however a slight inkling, for Lisa had commanded him to refrain from masturbating for five days before his visit.

“Hello ladies!” Lisa’s traditional greeting when she went to her place of investment and occasional work. Her partner was the manageress of the establishment and Lisa provided the money.

Squealing of pleasure and hugs all round. The staff were nothing if not effusive in their behaviour and Lisa beamed with pleasure. She was informed that there was just one customer in at the moment, enjoying a two-girl massage with a prostate massage to finish with. She introduced Tom, who nodded politely as he was introduced to each member of staff in turn, blushing more furiously as he did so as he found so many of them attractive beyond his expectations. He knew about the different nature of some of the girls but having no experience of them, it was unlikely he could tell lady from ladyboy.

“We are going upstairs, but I may send Tom down on some errands during his visit. You know what to do.” She nodded to the gathered staff, selecting two to join Tom and her upstairs.

At the upper landing, Lisa turned to Tom and instructed him. “Tom, you will obey all of my instructions here in my domain. Failure to do so will inevitable end poorly for you.” Tom nodded assent, secretly knowing that nothing was further from his intentions. He was completely in Lisa’s thrall and little she could do would dismay him.

“The first thing you must do is remove your clothing, Tom, and hand each item to Som here.” She indicated the Thai girl beside her, who smiled and clasped her hands together in a ‘wai’ of greeting. She was a tall girl, with quite large hands and bare feet. The wooden flooring seemed appropriate for bare feet and Tom started with his shoes and socks.

Lisa, Som and the third girl, Loy, watched, amused, as Tom finally drew his pants down to his ankles and stepping out of them, folded them neatly and handed them to Som who took his whole wardrobe away and secured everything, clothes, watch and phone, away in a locker at the side of the landing.

“Slaves are always naked for their mistresses upstairs, Tom. Your clothes will be returned once you have completed the tasks I set for you. You will obey all commands given to you inside this place, no matter who gives them. And every one of my staff will be addressed as ‘Mistress’. Is that clear?”

“Yes, Mistress Lisa. I understand. Thank you.” Why he thanked her he couldn’t imagine. He could see the other two girls smirking and felt humiliated, standing there naked with his hands clasped in front of his still flacid member in a futile attempt to reduce his exposure to them. Lisa had ensured that he was completely bald between navel and knee, not a single pubic hair in sight.

“Punishment position, slave!” Lisa commanded and he quickly adopted the now familiar stance.

“Approach the bannister rail.” It was higher than his waist and he realized that his dick was easily visible from the reception area below. Three or four of the girls looked up and smiled widely as he found himself now exposed to their view too.

“Bend over the rail, slave.” Lisa’s command ringing in his ears as he placed his chest on the rail, his reddened face looking down on the gathered witnesses to his humiliation.

Som produced a long thin rope and from behind, she tied a loop around Tom’s cock and balls, tightening it as she pulled it closed. Tom felt the blood flow increase as his cock hardened and then himself being pulled forward as Som and Loy each took an end of the cord, tied it around one of the supporting balusters and, pulling slowly on each end of the rope, drew him to the very edge of the landing. His growing erection was now poking through the posts and pointing, albeit upwards, very visibly towards the reception girls.

Gasps of amusement and several catcalls and bawdy whistles came from downstairs as the sounds of palm on buttock began to resound through the building. Tom was tied to the banisters, with his cock on display, being spanked loudly by his mistress, much to the entertainment of the entire gathering of eight or nine females below.

Hand gave way to leather paddle. The sound changed and the intensity built up. Tom’s ass was glowing and after five relentless minutes he was almost in tears. Finally, the spanking was concluded and the rope released from his aching genitals. The rope had been soft and smooth and as Tom was clean shaven, the skin was not damaged, but it was greatly stretched as Tom’s erection pulsed with his heartbeat. Painful it may have been, but the humiliation had filled his cock.

He was led into one of the rooms leading off the landing. A room the likes of which Tom had only seen on websites. A Dominatrix’s dungeon. Black furniture, red walls. The walls were adorned with instruments of pain and pleasure and chains dripped down from the ceiling. Tom knew he was in over his head, but he trusted Lisa.

“Are you thirsty, Tom? Would you like something to drink?” Som asked sweetly.

“Thank you, Mistress. Yes please.” He responded.

Loy found and attached a leather cone-shaped ‘parachute’, clipping it over Tom’s balls. Metal chains hung below it, connected to a ring. His wrists were secured into leather cuffs and clipped behind his back, exposing him fully in front.

“You may go downstairs and ask the receptionist to give you some water then, Tom. In fact, I think we would all like some. Please bring four bottles with you, or as many as you can carry each time.”

Tom stepped out onto the landing and made his way down the stairs, naked, exposed, erect and ashamed. The girls gathered round and stretched out hands as he passed to fondle his cock or slap his reddened buttocks. One grabbed a nipple and gave it a squeeze.

“Please may I have four bottles of water?” he said to the receptionist. “One for everybody upstairs.” He added unnecessarily. He was blushing hotly as she casually stared at his throbbing cock. Without a word, she leaned back, opened a fridge door behind her and brought out four bottles of water. Curiously, they all had a tag around the neck, with a wire hook. Tom suddenly gasped. He knew what the hooks were for.

“Legs apart. Stand still.” The receptionist ordered him, and as he obeyed, she hung a bottle of water onto the ring connected to the chains suspended from his parachute. Slowly lowering it, she checked Tom’s expression as she let go.

500 mls of water weigh half a kilo and this was now tugging on his balls. “Oh!” he uttered.

“Would you like to save yourself four trips up and down the stairs, slave? I can add the other bottles if you ask me nicely.”

This was an old trick, but the massage girls never tired of seeing slaves being humiliated, and Tom was no exception. They enjoyed his discomfiture.

“Go on, slave. Can you carry a kilo with your balls?” one of them goaded him, but Tom knew his limits; he had never carried anything with his balls before. Added to that was the difficulty of walking with such a burden between his knees. He stepped away gingerly and slowly climbed the stairs where Lisa was waiting to gather the first of his deliveries.

Three times more, Tom brought his painful load to the landing for which he was rewarded with a whipping from Loy. “Just twenty-four lashes, Tom. Six for each time you climbed the stairs with your gifts for us all.” She thrashed his back, buttocks and the back of his thighs.

“You have a lovely ass, slave.” Said Som, “Smooth and hard and hairless.” She added.

“Thank you, Mistress.” Tom responded.

“I am looking forward to fucking it.” Som informed him.

Oh, Christ. Is she a ladyboy? I’ve seen the size of some of their dicks on the websites. She’s a lot taller than me too. Oh, god, I hope she hasn’t got one of those monster cocks. Maybe she meant just with a dildo, like that whip Lisa used on me that time.

“Yes, Mistress. Thank you.” Tom thought how bad was the trouble he was in.

“Mistress Lisa tells us you want to swallow my cum, slave Tom. Is that true?” Loy piped up, putting Tom on the spot. Obviously, he knew this was gonna be a possibility when he agreed to visit Lisa’s establishment, but he hadn’t really believed it would happen. Until now. So Loy is a ladyboy, he surmised, and it seems Som is too.

At that moment, Tom was hanging spread-eagled from an overhead beam, with a leg-spreader ensuring his full exposure. He felt a new stirring in his flacid penis as the dull realization of his helpless situation sunk more deeply in. Was he really gonna get fucked in the ass by a ladyboy, and have to suck the cum out of another one’s cock?

“That’s right, Tom,” Lisa joined the conversation. “I can see your thoughts in your eyes. You are wondering if Loy is a ladyboy and going to fuck your ass with her big cock. Will she just fuck it, or will she have an orgasm inside your ass? And Som? Well, she has just made it clear to you that she is going to put her cock in your mouth for you to bring her to a copious climax which will fill your mouth with cum. Will you swallow her cum, Tom?”

Tom’s cock swelled to bursting, throbbing erection as he listened to Lisa and tears of humiliation formed in his eyes as he answered his mistress.

“Yes, Mistress Lisa. Thank you. Please be gentle with my ass, Mistress Loy, but again, yes, please, I want to feel you stretching my anus and fucking my ass until you fill it with your cum. Mistress Som, please allow me to worship your cock with my mouth and tongue, and swallow your ejaculation while Mistress Lisa watches me debasing myself.”

The three mistresses clapped their hands in pleasure at the willingness of their slave.

“Truly, Tom? Do you truly want all that you have just asked for?” Lisa wanted him to repeat his request. “Shall we invite the rest of the girls from downstairs to come and watch too?”

Tom’s cock nearly exploded. There must be a dozen of them, girls and ladyboys, and they would all watch as he took a cock in the ass and sucked another to climax. His humiliation would be overwhelming.

“Yes. Please, Mistress. Please invite all your staff to witness my embarrassment.”

* * *

Evelyn’s doorbell rang unexpectedly and she thought who it might be.

“Tom!” she said in surprise. “I didn’t expect to see you. What can I do for you?”

In fact, she had a pretty good idea and had been half expecting a visit.

“Mistress,” he started as they walked through the house to the poolside, “I think I want to just see you from now on.”

“Ah! I see. Lisa went too far with you. She told me what happened and for what it’s worth, I apologise. She can be rather too enthusiastic sometimes.”

“That’s about it, Mistress. I quite enjoyed my visit to her massage place, but it got a bit out of hand towards the end and I ended up having to satisfy six ladyboys by sucking them all off. I had to swallow all of their cum and frankly it made me a bit sick. I wasn’t ready for that kind of orgy, especially being the only submissive one there.”

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