Chapter 1: Dinner and a Surprise

Paul and Lara had been talking for weeks, ever since they first matched on the dating app. Now, they had finally made plans to meet in person, and they both knew they were eager and a little bit nervous. They had agreed to meet at the Black Olive, a cozy little Italian restaurant in Vancouver, BC.

Paul arrived first, and he was already seated at a table when Lara walked in. His breath caught in his throat when he first saw her – she was even more beautiful in person than she had been in her pictures. She wore a simple black dress that showed off her curves, and she had a hint of a mysterious smile on her face.

After the customary greetings, Lara and Paul started talking about their lives. They talked about their jobs, their families, and their hobbies. Paul was surprised to learn that Lara worked as a dominatrix – it wasn’t something he expected to hear on a first date. But he found himself intrigued and strangely excited.

After dinner, Paul walked Lara to her car. He was about to kiss her, but she stepped back with a mischievous look in her eyes. “I think I should let you know what kind of surprise I have in store for you,” she said. Paul was intrigued and a little bit scared, but he nodded and said okay.

Lara then told Paul that she was a professional dominatrix, and that she was offering him the chance to explore his submissive desires with her. Paul was surprised and a bit taken aback – but he also found himself strangely intrigued.

He thanked Lara for her honesty and said he would need to think about it. She smiled and said goodnight, and they parted ways.

Paul couldn’t stop thinking about Lara and her offer as he drove home. He was both scared and excited, ad he wasn’t sure what he should do. But one thing was certain – he couldn’t wait to see her again.

Chapter 2 – Teaching Paul Bondage

Paul nervously stood in the small room, unsure of what the night could bring. His heart was pounding as he wondered if he was ready to take this risky step. He had heard stories of people getting hurt or abused while engaging in this type of activity, but he was willing to take the risk.

He looked around the room, taking in the sparse furnishings. There was a bed in the corner and a few chairs, but nothing else. His eyes eventually found their way to the woman standing in the center of the room.

She was dressed all in black, with a stern expression on her face. She was tall and imposing, her presence enough to make Paul cower. He knew immediately that he was in her domain.

“Welcome, Paul,” she said in a firm voice, “I’m your Mistress for tonight. We’re going to be engaging in some light bondage play, so we need to set some ground rules. The most important one is that you must obey my every word, no matter what. If I say do something, you do it, no questions asked. Do you understand?”

Paul nodded, feeling a bit overwhelmed by the situation. He had heard of safe words before, but he had never actually encountered one in person.

The Mistress continued, “The other rule is that you have to use a safe word if you ever become uncomfortable or feel overwhelmed. That way, I’ll know to stop what I’m doing and we can talk about it. Do you understand?”

Again, Paul nodded. He felt a bit more comfortable now that he knew what to expect.

The Mistress then proceeded to teach him about safe words and how to use them. She also showed him a few basic bondage techniques that he could use in the future if he wanted to.

After a few hours, the Mistress declared that their session was over. Paul felt relieved, but also a bit disappointed that it was over so soon. He had enjoyed the experience and was looking forward to doing it again.

The Mistress smiled and patted him on the shoulder. “You did well tonight, Paul. I’m proud of you. I look forward to seeing you again soon.”

With that, Paul left the room, feeling a bit more confident in himself. He had taken a huge risk, but in the end, it had been worth it. He felt a bit more daring and open to new experiences, and he was looking forward to the next session with his Mistress.

Chapter 3 – Lara Fucks Paul Her Way.

Paul was a little apprehensive as Lara announced that she was going to fuck him that night. He had heard about pegging, but he had never experienced it before. He knew that it would make him feel vulnerable, and he was both excited and scared at the same time.

Lara explained that pegging was a type of sexual activity where a woman would penetrate a man with a strap-on dildo. She showed Paul the dildo that she had brought, and then gave him a detailed explanation of what would happen during the pegging session.

She told him that she would begin by lubricating the dildo, and then slowly insert it into his anus. She warned him that it would feel strange and uncomfortable at first, but that he should take slow, deep breaths to relax. She then gave him a few tips on how to make the experience as pleasurable as possible, such as focusing on the sensations in his body and breathing deeply.

Once the dildo was inserted, Lara asked Paul to let her know when he was ready. When he was, she began to thrust in and out of him, slowly at first and then gradually increasing the speed. Paul felt a mixture of pleasure and pain, but he was determined to push through it and enjoy the experience.

As Lara increased the speed, Paul felt himself becoming more aroused. He began to moan with pleasure as he felt himself getting closer and closer to orgasm. Finally, when he couldn’t take it any longer, he let out a loud moan and came.

When it was over, Paul felt a strange sense of satisfaction. He felt as if he had just gone on an incredible journey and emerged with a new understanding of his body and sexuality. He thanked Lara for the experience and snuggled up beside her.

They lay there in bed for a while, talking and cuddling. Paul had never felt so close to someone before, and he knew that this experience had changed him in some way.

The next morning, Paul woke up feeling refreshed and invigorated. He knew that this experience had been transformative, and he was eager to explore more. He thanked Lara again for her patience and guidance, and they made plans to explore more of the world of bondage and kink in the near future.

Chapter 4 – Turning Paul into Cash Cow.

To get Paul to like wearing female clothes and makeup, Lara was very patient and understanding. She slowly introduced him to the idea, and then let him take it at his own pace. She helped him choose clothes and makeup that he felt comfortable in, and allowed him to experiment without judgement or ridicule. She also provided him with support and comfort as he adjusted to this new role.

Once Paul started to feel comfortable in his new wardrobe, Lara began to train him to be her fulltime sissy maid. She taught him the rules and expectations of her lifestyle, and gave him a clear understanding of what it meant to be her sissy maid. She also gave him rewards when he did well, and punishments when he failed.

One of the tasks Lara asked Paul to do was to give her clients blowjobs. At first, Paul was shocked and embarrassed, but Lara was persistent. She said that it was necessary for him to do this in order to serve her properly.

Paul reluctantly agreed and started sucking cock on a regular basis. Over time, he got more and more comfortable with it and even began to look forward to it.

Eventually, Lara could trust Paul enough to let him serve her clients without her being present. This created a lot of opportunities for Paul to explore his own bisexuality and meet new people.

Paul had become Lara’s personal sissy maid, and he couldn’t be happier with the arrangement. He enjoyed the freedom that came with being able to explore his sexuality and also the respect he was given by Lara’s clients.

He had no responsibilities or job. His only focus was to make sure Lara’
s house was clean before her clients came over, and then to serve her clients sometimes with Lara and sometimes on his own.

When Lara brought dominant clients in, it was all about the client using Paul as a sexual toy anyway they seen fit.

When Lara’s dominatrix clients came over, sometimes Lara would indulge Paul with a treat and get her submissive to give Paul a blow job.

The only way Paul ever got to cum was being fucked by Lara and a strap on, or getting a blow job from one of her clients. Overall, Paul had become quite happy with the arrangement and enjoyed the lack of thinking he had to do.

Paul had gone from a timid man to a confident bimbo sissy maid who loved sucking cock. He had Lara to thank for it all, and he was grateful for her guidance and support.

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