Esper Harem in the Apocalypse

Rudy smirked mischievously and asked Jane if she wanted to try BDSM, since she was already chained.

Jane blushed furiously at Rudy's mischievous suggestion, feeling both embarrassed and surprised by his response. "W-Well, I didn't mean it like that!" she stammered, trying to regain her composure. "I was just curious, you know..."

Rias chuckled, finding the situation rather amusing. "It's alright, Jane," she said, giving her a playful pat on the shoulder. "We all have our curiosities, and there's no shame in that. When I gained the knowledge of the human world, I was also curious and confused about most things."

Rudy grinned, still teasing Jane a little. "If you're genuinely interested, there's nothing wrong with exploring new things," he said, trying to lighten the mood.

Jane's blush intensified, but she appreciated Rudy's understanding and advice. "I-I guess you're right," she mumbled, feeling a mix of embarrassment and gratitude.

Rias took charge of the situation, returning the conversation to a more serious tone. "As for the shackles, we can't remove them right now," she explained. "They're designed to drain energy, and it wouldn't be safe. I don't want Rudy to take them off either since the last time he did that, he had passed out. And I don't want that to happen when we are about to have lots of sex."

Jane nodded, understanding the reasoning behind Rias's decision. "Okay, I get it," she said, resigning herself to the fact that she would have to wait until they could find a solution.

"So? Do you want to try it or not?" he asked calmly. "Frankly speaking, this would be my first time too and we won't do anything extreme… of course. I wouldn't even have brought this topic if Maria or Reina were in the question.

They are humans. I can't even go rough with them. But I don't have to worry about the non-humans. I get to try new things with them."

Jane pondered about Rudy's offer for trying out what she mentioned. Her curiosity and excitement got the best of her, and after thinking about it for a while, she agreed.

Feeling a mix of nervousness and anticipation, she looked at Rudy with a slight blush on her cheeks and nodded.

"Alright," she said softly, "Let's give it a try."

Rudy smiled gently and assured her, "Don't worry, we'll take it slow and only do what you're comfortable with. If you feel physical pain of any sort, let me know."

He carefully got close to her, and Jane's heart raced with a mix of excitement and nervousness.

Rudy turned to Rias, his eyes seeking her approval, as they were on a path that seemed to lead towards a threesome, given the situation they were in. He remembered the promise he had made to Rias to seek her approval for any such encounters, especially the first time they considered a threesome.

Rias looked into his eyes, her own gaze filled with a mixture of emotions - trust, love, and a hint of hesitation. She knew this was an important moment for both of them, and she appreciated Rudy's respect for their agreement.

Rudy didn't say a word to ask her, he simply looked at her. And Rias understood Rudy. With a soft smile, Rias nodded, giving her consent. "Go ahead, Rudy," she said quietly.

"I know you have been dying to have a threesome. You probably regret making that promise to me since you had many chances to have threesomes with other girls. To be honest, I didn't think you would keep that promise since it was related to sex and your libido.

I wouldn't have gotten angry or blamed you since it's hard to control your libido and very easy to give into the temptation. However, I must say I am surprised and honored to know that you kept your promise."

"You know I never go back once I have made a commitment. I am true to my words."

Rudy reached out to caress Rias' cheek tenderly, expressing his gratitude for her understanding.

Feeling reassured by Rudy's words and touch, Rias leaned in and kissed him gently. She knew that their love for each other was strong enough to explore new dimensions of their relationship, and she was willing to embrace the experience.

With Rias' approval, Rudy turned his attention back to Jane, who was watching the interaction between them with curiosity. He leaned in to whisper to her, "Rias is okay with this. We can proceed if you're still interested."

As Jane considered Rudy's proposition, her curiosity and excitement got the better of her. She couldn't deny the allure of exploring something new and adventurous with Rudy. With a mix of apprehension and eagerness in her eyes, she finally nodded, accepting his offer.

Rias, who was still sitting beside them, raised an eyebrow at the unfolding conversation. She knew Rudy's mischievous nature and understood that he was always up for trying new things. However, she wanted to make sure that Jane was genuinely comfortable with the idea.

Even though she was still angry at Jane and hadn't completely forgiven her, as her big sister, Rias couldn't help but be concerned about Jane. Her anger couldn't surpass her sisterly love for Jane.

"Are you sure about this, Jane?" Rias asked, her voice tinged with concern. "It's okay if you change your mind. We can find other ways to have fun."

Jane looked at Rias and appreciated her concern. She took a moment to gather her thoughts before answering, "I'm curious, Rias. It's not something I've experienced before, but if Rudy is willing to guide us, I trust him. You should try it too."

"I will pass."

"Rudy can tie you using clothes or something. But since you just lost your virginity, I guess you want to have normal sex."

Rudy, who had been listening attentively, smiled at Jane's response. He reached out and gently squeezed her hand, assuring her of his care and respect. "Don't worry, Jane. We'll take it slow, and I'll make sure you're comfortable every step of the way."

With that reassurance, Jane felt more at ease. She knew that Rudy would respect her boundaries and ensure her safety and would never let harm come her way. Her curiosity about the unknown experience outweighed any reservations she might have had.