My Journey Into A Loving Female Led Relationship: Chapter 25

My name is John, though I go by rgjohn, and I’ve written a few erotic books and some content for Literotica. When Emma read my work, she suggested I write about loving, female-led relationships—a genre she’s passionate about. It’s been a while since I’ve written, but a fan recently reignited my interest by asking me to turn his detailed journal into a story. Initially skeptical, I found myself captivated by his account of a Female-Led Relationship (FLR), a concept I hadn’t explored before. With a mix of curiosity and research, I’ve decided to craft a multi-part story spanning over 20 chapters. If you are just starting, you should begin your journey back at chapter 1.

Chapter 25: Anna Teaches Sally The Ins And Outs Of Discipline, Anna Takes A Three Day Trip Leaving Sally In Charge

Over the next month, Anna and I settled into a comfortable yet evolving routine. Her career was progressing well, though the looming decision about her partnership kept a steady undercurrent of tension in our home. Office politics weighed heavily on her, and despite her best efforts, some days the stress was off the charts.

Anna believed that achieving a full partnership, joining the elite ranks of only three others in her firm would finally ease some of the pressure. Until then, she carried that weight with her, and more often than not, I became her outlet.

Our discipline sessions grew in both frequency and intensity. The strikes from her cane or paddle came harder, her focus sharper, and her emotional release more apparent. I didn’t mind. It wasn’t that I enjoyed the pain itself… I didn’t… but knowing that I was helping her unwind, providing her with some form of catharsis, made it worthwhile.

And afterward, when she’d run her fingers gently over the marks she’d left, whispering words of gratitude and affection, those moments made every stripe and bruise meaningful.

But it wasn’t all discipline. Anna’s focus on my sexual maintenance became a cornerstone of our relationship. She kept me in a constant state of arousal… an almost maddening edge where release was dangled just out of reach. Daily maintenance sessions became our norm again, but full climaxes were still forbidden. I barely remembered them now. I did, however, remember that the fleeting satisfaction of a climax left me feeling drained, hollow, and disconnected. Instead, I found an amazing satisfaction in the aching, endless craving that Anna expertly maintained.

As our relationship evolved, Anna began involving Sally more deeply in our FLR journey. Sally had become increasingly curious about the lifestyle and was eager to transition her relationship with her husband, Chris, into something similar. She and Anna spent hours discussing strategies, boundaries, and emotional nuances. Those conversations often happened with me present, though they spoke about me rather than to me, a subtle yet intentional power dynamic that I quickly grew to understand.

Sally’s visits became more frequent, and Anna began delegating certain responsibilities to her. At first, it was awkward. But Sally gradually grew into her role. Under Anna’s guidance, she learned to wield the cane with more precision, to recognize subtle cues in my body language, and to maintain control over her own emotions during our sessions.

The first Saturday session with Sally as the primary disciplinarian was particularly memorable. Anna sat nearby, coaching her friend through every step. It started with a paddle, the wide surface leaving even, stinging redness across my skin. Then came the cane… a tool Anna now wielded with the grace and precision of an artist, but which Sally was still learning to master. Mistakes were met with repeated strokes, and repeated strokes meant prolonged punishment. By the end, my body was trembling, my backside striped with vivid red lines. Yet, when it was over, both women praised me for my composure, and Anna leaned down to kiss me gently on the lips.

As a reward, or perhaps as further torment, Anna and Sally conducted a joint tease-and-denial session afterward, often using the punishment chair. Anna expertly worked me to the brink several times, her eyes locked onto mine with that playful glint I’d grown to love. Then she handed me over to Sally, who, under Anna’s instruction, executed multiple ruined orgasms with surprising skill. When they finally let me rest, I was physically and emotionally drained.

Then of course, both women used the chair, sitting there on the soft cushion, as opposed to the one I had to use, they would keep me between their legs until they had reached total satisfaction… which meant multiple climaxes for both of them. Sally liked to reverse things and kneel on the chair with her ass facing me. I knew what that meant and what she wanted… something she was unable to get anywhere else. She loved it and I was more than happy to provide it for her and Anna.

In the days that followed, the three of us engaged in several lengthy and meaningful discussions about Female-Led Relationships (FLRs)… with my input simply from a male perspective. While much of the conversation centered on helping Sally navigate the transition within her marriage, Anna introduced an idea that could offer Sally a hands-on learning experience.

Anna’s announcement about her upcoming three-day business trip caught me completely off guard. We were curled up on the sofa after one of our usual movie nights, the soft glow of the moon spilling through the floor-to-ceiling windows. Everything felt peaceful, intimate, until she dropped the news.

“I’m going on a business trip next week,” she said, her fingers absently running through my hair. “I’ve asked Sally to come over and stay here while I’m gone.”

At first, I thought I had misheard her. Sally? Staying here? My mind raced with questions, confusion tightening my chest. “Wait… am I going on the trip too?” I asked, a flicker of hope in my voice.

Anna shook her head with a patient smile. “No, Jason. We’re heading to Detroit, and it’s freezing there right now. Trust me, you wouldn’t enjoy it. I will be in meetings all day.”

Her words settled in, and the realization hit me. “Then… why is Sally coming here?”

Anna’s expression softened, but her voice carried a firmness I knew better than to challenge. “Because this is a perfect opportunity for her to learn, Jason. Sally’s been making progress with Chris, teasing him, denying him, and starting to guide their transformation. But she still has so much to learn, and so does he… he is a tougher case than you ever were. I want her to see our routines, understand the trust we’ve built, and experience how this works firsthand.”

I froze, the weight of her words sinking in. Sally was going to stay here, with me, in our space, following Anna’s instructions and expectations. It wasn’t about distrust; I knew that. Anna trusted me completely. But still… it felt strange, uncomfortable even.

“I don’t need a babysitter,” I blurted out, the words slipping out before I could stop them.

Anna’s gaze sharpened, her lips pressing into a thin line. She said, “If I were still giving you demerits, that would add fifteen,” she said calmly.

I shut my mouth instantly, regret flooding me. I had crossed a line, and I knew better. I took a breath and lowered my eyes. “May I speak freely now?” I asked cautiously.

Anna nodded. “You may, but watch your tone.”

“I’m just… confused,” I admitted. “I know you’re close to Sally, and I get that you want to help her. But why does she need to be so involved in our relationship?”

Anna’s expression softened again, her fingers brushing against my cheek. “Because I love her, Jason. And I want her to be happy. She’s not happy right now, and I want her to have what we have. You’ve come to care about her too, haven’t you?”

I couldn’t deny it. While Sally had become a fierce disciplinarian, she was also kind, intelligent, and loyal. I respected her, and yes, I cared about her too.

“Sally’s not just a friend to me,” Anna continued. “She’s family. More than family, really. You don’t know this, but Sally lived with us, my parents and me, for years.”

My brow furrowed. “Why?” I also wondered why she hadn’t told me… then I remembered my journals and didn’t press that conversation.

Anna’s voice softened, and her eyes glistened slightly. “Her parents died in a car accident when she was ten. My parents were distant relatives of hers, but they were very close to her family. They took her in, no hesitation. We weren’t just like sisters, we became sisters.”

My chest tightened at the revelation. “I… I had no idea.”

“It’s not something Sally talks about much, even to me. It’s still painful for her. But we’ve shared so much, Jason. We roomed together in college, got our first apartment after graduation. I was her maid of honor, and she stood beside me at our wedding. I want her to be happy… to experience what a real FLR is all about. I want her to see how it works in real life and in real time.”

The weight of her words pressed down on me, filling the silence between us. This wasn’t just about Sally observing our routines or learning about FLR’s, it was about trust, love, and years of unshakable loyalty between two women who had been through so much together. I couldn’t deny either of them that.

As the trip approached and the plan began to take shape, I could feel the anticipation building. Sally prepared herself diligently, asking Anna question after question about my routines, preferences, and expectations. Anna answered them all with care and precision, ensuring Sally understood not just the mechanics of our FLR but the emotional nuances as well.

For me, the approaching trip felt heavy with both uncertainty and nervousness. I trusted Anna implicitly, and if she believed this was the right step for Sally, for herself, and for me, then I would follow her lead. But deep down, I couldn’t shake the feeling that this experience would test me in ways I hadn’t yet anticipated.

Before Anna left, there was something nagging at me, and I needed clarity. During dinner one evening, I finally spoke up.

“Uh… how… uh far… can, you know, Sally go with me?” I asked hesitantly

.

Anna tilted her head slightly. “What do you mean?”

I swallowed hard. “Uh… I mean, is she your surrogate? Can she do everything you do with me? And do I… do everything I do with you, with her?”

Anna’s smile was knowing, her confidence unwavering.

“Everything.”

I blinked, absorbing her answer. “So, what if she wants me to … uh … you know, penetrate her.”

Anna burst out laughing. “You really think she is going to do that?”

I shrugged, the question was only half in jest. I took a step back and said, “Okay, if you’re sure about all this…”

“Jason, I wouldn’t be doing this if I had any doubts… about you or about Sally. You two love each other as friends. I know Sally is never going to steal you from me… am I correct?”

“Of course. You know there will never be anyone else for me. Even if you left me, I don’t think I could or would ever find anyone like you. I don’t know if I could live without you.”

Anna’s eyes softened, and she stood, pulling me into a hug. “Don’t say that, Jason. It still scares me. First, I’m not going to leave you. And if anything ever happened to me, I would want you to go on with your life.”

Tears welled in both our eyes as we held each other.

“Okay,” I said softly. “I just wanted to make sure there was no misunderstanding.”

“There isn’t,” Anna reassured me. “You will do for and treat Sally just like me, in all ways.

I took a deep breath and said, “Okay. Uh… what about Chris. Does he know Sally is going to be staying here?”

“No. He thinks that she is going on the trip with me,” Anna said with a smile. “She is letting him go on a week long golf trip with his buddies. To get to do that, he was willing to let her go anywhere.”

“Oh,” I said. I was a bit relieved because Chris sometimes calls me to go to lunch. I didn’t want to lie to him. 

“We’ll talk often while I’m away. And if you have any questions, just call me.”

She waved her phone at me with a playful grin, as if I had forgotten they existed. I felt a deep sense of relief wash over me. Everything was going to be okay.

Continue to Chapter 26