Billionaire's Pleasure-Chapter 153: Training 1

Jackson’s POV

Victoria seemed like accepting my offer. If she does, I should be prepared. I thought about what I’d been thinking about and the various challenging that could develop. Victoria was my entire world, and I couldn’t bear the thought of anything awful happening to her. That’s why, whatever occurred, I had to make sure she couldn’t or wouldn’t be injured. I encountered a woman who advertised herself as a dominatrix as a result of my internet investigation. I made contact with her.

"Hello. This is Ms. Cathy speaking."

"Hi, my name is Jackson, and my wife and I are considering subjecting her to a brief period of sensual servitude."

"Please let me know if you don’t mind me taking up her training."

"No, no. Despite I want to be the dominant one, I know very nothing about it beyond what I’ve read in popular erotic novels. I need to understand more about it so that I don’t unintentionally do something that could injure her. I’d love it if you could give me some guidance before we start because it appears that she going to agree to my offer."

"That is something which I can help you with. When exactly do you want to get started?"

"Soon. Due to my work schedule, the best time for us to meet is in the evening, unless you have some free time this night."

"Sure. I have a spot available this evening."

"Could you just tell me what time it is?" I asked.

"Maybe eight o’clock," she answered.

"All right. Is there anything else I need to bring?"

"Your money, of course. My time is worth $100 per hour. Cheques and credit cards will not be accepted; only cash or debit cards will be accepted."

"Okay, I’ll need your address, just message it to me. I need to call my wife first. Bye thanks." I drop the call to Ms. Cathy and immediately called Julia and told her that I would not be arriving home early after work because I’m going to meet someone. If she chose to accept my offer, I need to meet her, someone going to teach me how to be a dominant master.

"Could you tell me who you’re going to meet?"

"Ms. Cathy... someone who can help us to fulfill your fantasy."

"Um...You’ll have to tell me about it later."

"Of course, Honey. Don’t worry about it. I will not go to cheat on you."

"But still possible. Well, I’ll talk to you later. I love you." Victoria said.

"Okay, see you later, honey. I love you too."

At 8:00 p.m., I arrived on Miss Cathy’s doorstep after a quick bite to eat and a $500 cash withdrawal from an ATM machine. She lived in a good neighborhood that reminded me of mine, which I found fascinating. A woman which whom I’m not familiar came up to the front door and invited me in as soon as I announced my name.

"Come in." she simply said.

She wasn’t unpleasant in look, even if she was a little overweight, so I eagerly followed her inside her house. She opened a door to reveal a large room with dim lighting and a variety of cages, poles, and ropes that I didn’t understand at the moment. Whips hung from the ceiling, rods or canes were meticulously packaged into small boxes, and shelves were stacked high with different kinds of toys. I saw a male hamster in a little cage on the floor, eating from a dish and drinking from a nearby basin of water.

"Miss Cathy, your appointment at 8:00 p.m. has been set."

"Oh, thank you so much. Just go stand in the corner till I summon you to join me."

Before standing and retreating to a corner, the overweight girl kissed Miss Cathy, and then walk towards me and reached out to shake my hand.

"Is it Jackson?" Miss Cathy asked.

"Yes," I answered.

"If it’s all okay with you, I’d want to ask you a few questions before we begin."

"Of course." 𝚏𝗿𝗲𝐞𝐰𝚎𝕓𝐧𝚘𝘃𝗲𝐥.𝐜𝚘𝕞

"Do you think your wife will eventually become your slave, or do you think this will be a one-time thing?"

"I’m not convinced it’ll be permanent. She enjoys reading erotic, so I proposed that she try out the things she reads about in her books for three weeks to see if reality matched her imagination. We started our experiment when she agreed."

"Could you please tell me what kind of books you have?"

"Things like a reverse harem, and submissive women being punished by their master."

"Are these making her enthralled?"

"I think so."

Miss Cathy remarked, "It’s possible she’ll like it more than you think. Expect her to want to make it a semi-regular, if not permanent, occurrence in her life. People who are originally enticed by the notion of submitting often find that they prefer it once they have made the decision to do so. Do you intend to punish her in any way?"

"Spankings at the very least or punishment in front of others," I said.

"Have you considered whips?" Miss Cathy enquired.

"I don’t want to hurt her," I explained.

"Depending on the circumstances, a whip may be less harmful than a strong hand spanking. It may sting more fiercely at first, but the symptoms will likely fade faster. You should have one, in my opinion. Even if your slave doesn’t give you a reason to use the whip, seeing you with a whip in your hand excites her." she explained. "In order of worst to best, which of the following would you choose to have? " Miss Cathy asked.

"I think I prefer a cane but don’t want to leave a stain on my wife’s face."

"Oh, I see then you should use your hand to see how hard you’re striking her with it; your hand feels it just as much as her bottom. A paddle and a medium-width stranded whip that I will teach you how to wield will not leave a trace also. They will leave nothing but the smallest redness on your skin in the morning."

"Oh, okay. Noted with that Miss. Cathy. Thank you very much."

"I am able to supply you with the services you seek. You might be able to get similar things on the internet for a little less money, but the quality of my work is unmatched." I nodded and grinned. "Are you going to urge her to fuck other people?"

"I’m not going to force her to do anything, but I’m going to put her in situations where one of the possibilities is sexual activity with others, and it’s possible she’ll choose that."

"Does that include women?"

"I hadn’t considered including women."

"You should absolutely do so. If she is a slave, she should be treated as such, with the freedom to have intercourse with whomever her master desires. Did she date any women before?"

"I don’t think so."

"Good! Being a slave owner entails stretching her boundaries and refusing to let her stay in her small corner of the universe. Does she has the ability to employ a deep throat?."

"Um... She’s a really good sucker, but she never tried a deep throat. The most major problem I’m facing is her inability to swallow. Meanwhile, I’m trying to break her of that small habit while she’s my slave."

"Is it because of the taste of a cum?"

"It has something to do with the texture and sliminess. She compares that to eating raw oysters, which she also can’t eat."

"I believe I could help you with both of those problems."

"I’d love it if you could make some recommendations," I said.

"I’ve discovered a method for training new slaves that is incredibly effective. I’ll show you how to effectively overcome her resistance to swallowing. If you want some deep-throating, invite me over as soon as her slavery begins. I’ll make arrangements for her to pick up the rest of you as soon as possible. I would accept remuneration in the form of enabling me to teach her how to lick a cunt. "

"I’ll have to think about that," I said

"Okay. Are you going to use clamps on your slave?"

"I really wanted to, but hers have a high sensitivity level."

"Putting them on is always less painful than taking them off, depending on how tight they are," Miss Cathy explained. They’re squeezing the blood out of them, and when they’re removed, the blood rushes back with a jolt of pain, don’t they, dear?" Miss Cathy said while asking a girl beside her.

Mistress Dark stroked the tips of the purple nubbins together, making the girl moan. The girl replied, "Ugh. Yes, Miss Cathy."

"These are basic alligator clamps, comparable to what electricians use. They have razor-sharp teeth, yet they won’t rip the flesh; instead, they’ll give you an extra edge. To begin, I have a set of basic box clamps that are toothless. They simply use pressure to achieve their objectives."

She walked me through a succession of them and showed me how they worked.

"In most circumstances, clamps should only be left on for a maximum of fifteen minutes at a time. I recommend you, use a timer to make sure you don’t forget how long you use them. Occasionally, similar to removing a tourniquet, it is vital to enable the blood to circulate freely. You might also alternate applying pressure to the top and bottom from the sides."

"Could you tell me if you have any bondage furniture?" I asked.

"At this time, no. At the time, I was considering making my own. In the construction industry, I operate as a general contractor."

"At the absolute least, I propose across like this one," Miss Cathy said. "Hey come on over here and get the cross."

"Yes, Mistress." The girl gets out of her and trotted straight for the enormous X-shaped cross. She demonstrated to me how to use the cross. She bound her assistant to a crucifix with her back to it. She then pulled out a whip and started whipping her huge melon, tummy, and even her genital area, forcing her to scream.

"You can suspend them right side up or upside down if the cross is sturdy enough; however, suspension cuffs, rather than traditional bondage shackles, will be required. They add extra support to the foot and wrists while also preventing blood flow from being stifled."

"Doesn’t that hurt a lot?" I enquired further.

"Does it hurt?" she asked her assistant.

She grumbled as she answered, "Ugh, Yes Miss Cathy."

"Would you like me to stop?"

"No, please."

"You want to cum?"

"Please, Miss Cathy."

Miss Cathy whacked her several more times with the whip in her hands, leaving stripes all over her flesh that were not welting; she was finally hauled up between her legs, and her assistant gasped, clearly in pain.

"You want more?" Miss Cathy asked.