My Journey Into A Loving Female Led Relationship: Chapter 41

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 many chapters. If you are just starting, you should begin your journey back at chapter 1.

Chapter 41: Anna Goes On A Trip With Michael, Anna And Jason Decide To Have A Baby

Things progressed beautifully for Anna and me over the next year. I remained securely caged… perpetually teased and denied… yet deeply content. That ever-present hum of anticipation had become a constant companion, woven into the fabric of my everyday life. Climaxing no longer felt necessary; in truth, it had become something distant and unfamiliar. The yearning itself had taken root as part of my identity.

Anna’s connection with Michael also deepened over time. Every Friday night, and occasionally midweek, when he could slip away, he would come to our home and fulfill her desires with a tender confidence that never failed to make her glow. Their chemistry was undeniable. Watching how happy he made her only deepened my gratitude for his presence in our lives.

Some time ago, Anna had a business trip—a three-day legal convention in New York. As it happened, Michael was attending the same event. I wasn’t entirely surprised when she mentioned they’d be seeing each other there, but I was caught off guard when she casually added that they had arranged for adjoining hotel rooms. After the convention wrapped up on Friday, they planned to stay the weekend, returning Sunday evening.

Anna was radiant when she told me. She said she was looking forward to several uninterrupted nights with Michael, her eyes bright with anticipation.

Attending wasn’t even a consideration for me. I was staying home.

By then, it wasn’t unfamiliar territory. Over the past year, Anna and Michael had occasionally arranged overnight getaways—usually timed for the weekends when his wife took their kids to visit her mother. They would book a room at a discreet hotel well outside our city, minimizing any risk of running into someone they knew.

The first time they spent the night together had been difficult for me. It marked a turning point, and I’d be lying if I said it didn’t cause me a good deal of angst.

To Anna’s credit, she kept me involved. She texted me updates about her time with Michael, most of which revolved around what they were doing in the bedroom. That first night was agonizing. Anna and I hadn’t been apart overnight in a very long time. My mind spiraled with thoughts about what this meant, about where I fit into all of it. I knew this was a significant step in their relationship, and I struggled to make peace with it.

Anna did her best to reassure me. She said it was no different than when Michael visited our home… except she wouldn’t be coming to my room afterward to be cleaned up. I understood, logically, that this was what she wanted. I accepted it, because I trusted her. But it wasn’t easy.

Now, with this multi-day trip, my anxiety was even worse. They wouldn’t just be sharing a bed; they’d be spending all of their free time together. They’d be doing things that went beyond sex… sightseeing, dinners out, maybe even catching a Broadway show. Somehow, that bothered me more than the physical side of their relationship. It felt more personal. More intimate in a way I found hard to explain.

Deep down, I knew Michael loved Anna. And I knew she loved him. She assured me, time and again, that her affection for him didn’t diminish what she felt for me. She explained that she and Michael could never be together in a traditional sense… he loved his wife, and he was devoted to his kids. Anna believed it was possible to love more than one person… everyone did that… it was human nature. I believed that, too. After all, I felt a deep affection for Sally, though it wasn’t quite the same. Still, it worried me. But I trusted Anna. And because of that, I endured.

While Anna was away, I wasn’t entirely alone. She’d made arrangements for Sally to visit and ensure I wasn’t neglected. My tease and denial sessions continued, just as Anna wanted. In fact, several weeks before the trip, Anna had taught Sally how to peg me… something Sally quickly grew to love. She made it a point to do it every time she was charged with my care. She wasn’t as experienced as Anna, not at first, but by the time the trip was over, she had me discharging my prostate fluids the same way Anna did.

Of course, Anna didn’t worry about Sally and me. While we were fond of each other, we didn’t have the connection Anna shared with Michael. Not even close.

That connection was destine to grow even deeper… on a scale I could never imagine in my wildest dreams as you will see later in the story.

At some point, Anna had shared with Michael that I served as her clean-up boy. Of course he didn’t tell her that we had that discussion me being her clean up boy the first time he came to our place to fuck Anna. I felt guilty about not telling her, but Michael and I agreed it was for the best Anna only learned this when she read my journal. It was difficult for her, but she got it out through disciplining me… and I deserved it.

Anna thrived and managed this complicated relationship with grace and cunning. It had its dangers but also great benefits. With both of us fulfilling her needs… Michael bringing her physical satisfaction with his large cock and seemingly endless supply of cum, which Anna loved, and me… I made sure that she had her pussy cleaned properly after he took care of her, and I pleasured her with my mouth almost every day… often both front and back. There was no sexual desire that was not being provided for her.

Emotionally she had both Michael and me to keep her supported and grounded. She loved both of us different but equally, and of course, we loved her back. She had been promoted to partner at her firm six months ago and was now on track for an even higher leadership role. Her ambition and intelligence shone through in every interaction, and it was inspiring to witness her success firsthand.

Michael was thriving as well, excelling at his new firm. Their professional lives mirrored the harmony of their intimate arrangement. It was balanced, respectful, and deeply satisfying for all involved. Something amazing happened that shook Anna, which she didn’t share with me until much later… it involved Maddie, Michael’s wife. I will detail that in an add-on to this chapter.

Beyond this, Sally’s and our relationship grew as well. Like her love of pegging and disciplining me, she remained an integral part of our lives too. She had seamlessly stepped into the role of Anna’s stand-in when work obligations prevented her from focusing on me. Sally was far stricter in her discipline… her strikes landed harder, and her sessions lasted longer. Her teasing was relentless, her control firm. Yet, despite her intensity, I had grown genuinely fond of her. There was an undeniable strength in Sally that I deeply respected.

Interestingly, Sally had also transitioned her marriage with Chris into an FLR. At Anna’s suggestion, I had a heartfelt conversation with Chris, sharing my own experiences and helping him understand the profound benefits of a female-led marriage. It didn’t take long for him to see the light, and soon enough, Chris was wearing his own cage, with a Prince Albert, fully committed to serving Sally. From what I gathered, he was thriving in his new role… and so was she.

As for Anna and me, we had reached a significant milestone in our journey: Anna had decided it was time to start a family. When she shared her decision with me, I was overjoyed. Yet, the reality of our situation came with many concerns. I had been locked in chastity for nearly two and a half years, and while Anna ensured my physical health with regular maintenance sessions, I was rarely released and never had a full climax. I still got regular erections, mostly fully contained by the cage. Anna continued to tease and deny me by hand once a month or so, letting me get fully hard to ensure that I could still do it. Sometimes she would even take the cage off as she pegged me, and I never failed to get hard.

However, a full climax was strictly forbidden. Anna was unwavering in her decision: I was never to experience that level of release again… because she loved me and knew that I didn’t want that either.

That being the case, we considered IVF, thinking it might be possible to collect viable samples through a carefully orchestrated ruined orgasm. In fact, the doctor had said that she had patients that it worked for. With that hope, Anna took matters into her own hands, ensuring I was brought to the edge multiple times, and was finally let to climax, albeit it a ruined one. Then she collected enough actually sperm for medical evaluation.

Despite the challenges, I was thrilled at the prospect of fatherhood. The idea of raising a child with Anna, watching her embrace motherhood with the same strength and passion she brought to every other aspect of her life, filled me with hope and purpose.

Unfortunately, life has a way of throwing curve balls when you least expect them. I remember that Thursday morning vividly… it’s etched into my mind forever. The doctor had called, asking us to come in for an appointment. Neither Anna nor I said it out loud, but we both knew it wasn’t going to be good news.

The drive to the clinic was quiet. Anna’s hand rested in mine, her fingers trembling slightly. I gave her hand a gentle squeeze, hoping to offer comfort, though I felt just as unsteady as she did.

When we were ushered into the exam room and we sat side by side, Anna clutching my hand tightly as we waited for the doctor. Minutes felt like hours until the door finally opened, and the doctor stepped in. She had become a close personal friend of Anna’s and though her smile was warn, her expression told us everything before she even spoke. It was written all over her somber face. This wasn’t going to be the news we had hoped for.

“Anna, Jason,” she began softly, her voice carefully measured. “I’m afraid I have some difficult news.”

I felt Anna’s hand tense in mine. I could see her eyes already glistening with unshed tears as she braced herself.

“While there was enough sperm collected from the sample, the quality of the sperm is… concerning,” the doctor continued. “After running extensive tests, we’ve found that the sperm has extremely low motility and significant DNA fragmentation. Simply put, it’s not viable for IVF or any assisted reproductive procedures.”

Anna’s lips quivered, and her voice came out barely above a whisper. “Is there… is there another way? Could we try again? Maybe… maybe I could let Jason have a full release if that would improve the quality?”

Her voice cracked on the last word, and a tear slipped down her cheek. I squeezed her hand harder, trying to anchor her as much as myself.

The doctor’s gaze softened, her shoulders slightly sagging with the weight of her response. “I’m so sorry, Anna. Unfortunately, these results suggest a deeper issue. The damage to the sperm’s DNA isn’t something that can be reversed. Even with a full climax, Jason’s sperm will still have the same challenges. It’s not something we can fix. You are perfectly welcome to get a second opinion, and, in fact, I would suggest it.”

The finality of her words settled over us like a heavy fog. Anna bowed her head, her silent tears falling onto her lap. I couldn’t speak. My chest felt tight, and a dull ache throbbed in the pit of my stomach. The reality of what we’d just been told felt like a barrier we couldn’t move.

The doctor continued softly, her voice full of empathy. “I know this is incredibly difficult to hear. It is no one’s fault, just bad luck. I know it is hard to deal with, but take all the time you need and when you are ready we can discuss other options… like a donor sperm or adoption. We’re here to help guide you through those conversations.”

Anna nodded weakly, wiping her tears with the back of her hand. I wanted to say something, anything to make this better. But what could I possibly say? There were no words to ease this kind of heartbreak.

The doctor gave us a moment alone. As soon as the door clicked shut behind her, Anna turned to me, her eyes red and brimming with sorrow.

“I’m so sorry,” I whispered, my throat tight. “It feels like it’s my fault. Like I did something wrong.”

“It’s not anyone’s fault,” she said, her voice trembling as tears streamed down her cheeks.

I told myself it wasn’t my fault — just an unfortunate twist of fate — but deep down, I couldn’t help believing it was. I was the one with the damaged sperm.

I pulled her into my arms, holding her close as she buried her face in my chest. Her shoulders shook with quiet sobs, her grief spilling out in waves. I stroked her hair gently and held her tighter, letting her cry until the storm inside her began to ebb.

In that sterile, quiet exam room, we clung to each other, feeling the weight of a dream slipping away — the dream we had both held so tightly.

The following weeks were some of the hardest of our marriage. I couldn’t shake the fear that this might be what undid us. We’d seen it happen to friends — the silent erosion of connection under the strain of infertility. No matter how much we tried to push forward, the doctor’s words lingered between us, a shadow darkening every conversation, every moment of hope.

Even if it didn’t destroy our marriage, I knew it could leave cracks too deep to ignore. We needed a way through this. A real way.

We spent long evenings, sometimes entire days, discussing our options — adoption, surrogacy, sperm donation. Of the three, sperm donation seemed the most straightforward. But the deeper we looked into it, the more troubling it became. Many of the agencies operated under questionable standards, with screening processes that felt careless at best. Worse, there was no real way to know what kind of genetic legacy we’d be inviting into our lives. It felt like gambling with our future.

The disappointment stung. Again.

Yet, there was a solution, right in front of us — one that neither of us had dared to voice. Not yet. It had been in my head for weeks, but I couldn’t bring myself to voice it. But I think, deep down, we both knew. We both knew he was the answer.

Michael.

Still, choosing him wasn’t simple. It carried risks… enormous ones. It would place a burden on Michael, and it could strain his relationship with Anna. It could even hurt us all if things didn’t work out for any reason.

But then again, Anna and Michael already shared something rare. They had love, trust, respect… a bond that had only deepened over time. If Anna stopped taking her birth control, everything could unfold naturally. No clinics. No strangers. No terrifying unknowns.

And for the first time in weeks, I felt a flicker of hope.

I didn’t hesitate. Practically running to the bedroom, I found Anna reading, her expression wary as she looked up at me. I didn’t stop at the bed. I went straight into her bathroom.

When I came back out, she shot me a sharp look, irritation flashing in her eyes. She had been short-tempered lately, as my backside could well attest to.

“What are you doing?” she asked, her tone tight, feeling the intrusion into her sanctuary.

Without a word, I held up her birth control pills, then tossed them into the trash.

Her eyes widened in shock. “What on earth are you doing? Are you crazy?”

“Anna,” I said, my voice alive with excitement, “we know the answer. We’ve known it all along. It’s right in front of us. We have to try.”

Her brow furrowed slightly as she set the book down. “Perfect? Really?”

“Yes,” I said, my voice steady with conviction. “You just need to stop taking the pill.”

Anna froze, her expression unreadable at first. Her lips parted as if to speak, but she hesitated. I could see the wheels turning behind her eyes.

“You mean… without Michael knowing?” she asked quietly, her voice cautious and measured.

“No,” I said quickly, shaking my head. “Not like that. I’d never ask you to do something behind his back. We should ask him… together. I honestly believe he’d agree.”

Anna’s shoulders eased, though her expression remained thoughtful. She reached across the bed, her fingers finding mine, her thumb tracing slow, deliberate circles over my knuckles.

“Jason, this is a huge decision,” she said softly. “What you’re suggesting would bind the three of us together in a permanent way. There are so many layers to this… emotional, legal, everything.”

I nodded, eager but measured. “I know. I understand all of that. But you know as well as I do that it makes sense. Michael is a good man. He’s already part of our lives in such an intimate way, and I trust him. We can put everything in writing, make sure it’s legally clear. No surprises, no misunderstandings. And honestly?” I gave her a small, hopeful smile. “I don’t care if the baby looks like me or not. I’ll love that child with all my heart. I’ll raise them as my own. Besides,” I added, my smile widening just a little, “Michael and I do have a bit of a resemblance, don’t you think? People might never even suspect.”

Anna’s lips curled into a soft, reluctant smile, and I caught a glimmer in her eyes… relief, maybe even a spark of hope. It felt like the first time in weeks I’d seen that light return.

“You’ve really thought this through, haven’t you?” she said, her voice warm and touched with wonder.

I squeezed her hand gently. “It has been running through my heads for weeks. And I think… you have thought about it too, haven’t you? Maybe you’ve been thinking about it all along.”

Her smile deepened, and she let out a long, quiet breath. “You’re right,” she admitted. “I did think about it. But I had to work through it in my head first… really think about the risks, the impact on all of us. I needed to know that you were okay with it too… I wanted you to come to the same conclusion on your own and not be influenced by what I wanted. If you are sure about this…” She paused, her gaze steady on mine. “Then I can say yes.”

I felt a tight knot in my chest finally loosen, replaced by a quiet, growing warmth that spread through me. For the first time in what felt like forever, I felt steady. Hopeful. Ready.

Anna’s brow tightened as she spoke, her voice low but firm. “Jason, you do realize we’re about to step into completely uncharted territory. There are cliffs on every side, dangers we can’t fully see yet. This isn’t just unconventional… it’s something most people would condemn if they ever found out. We have to think about what this could do to our families, to Michael… and, if we’re lucky enough to have children, what it might mean for them too.”

Her words landed hard, but I was ready for them.

“I know,” I said, my heart pounding in my chest. “Believe me, I’ve thought about all of it. And yes — it scares the hell out of me. But Anna… look at us. We’ve never lived by anyone else’s rules. Not once. How many men spend every single day of their lives locked in chastity, trusting their wife completely? How many accept that their wife has a lover? How many husbands willingly submit to discipline, to the paddle and the cane, because it brings them closer, because it binds their trust so tightly?”

My breath caught, but I pushed through, feeling the truth surge in my chest.

“We’re already so far beyond anyone’s definition of normal, Anna. This… what we’re talking about… yes, it’s big. Maybe the biggest decision we’ve ever faced. But it’s just another choice in the life we have built together. We’re not following anyone else’s map. We’re making our own.”

I moved closer, my eyes locked on hers, letting her feel the full force of my conviction.

“Do we choose to stay childless? To watch our dream fade away because we’re afraid of what others might say? Or do we take this leap, this bold, terrifying, beautiful leap, and build the family we’ve always wanted in the way that fits us? We’ve looked at every other path, and none feel as right as this one. None.”

I tightened my grip on her hand, my voice deepening with resolve.

“And you know what? Let them judge. Let them whisper behind our backs. I don’t care. I don’t care what anyone else thinks, Anna. Not when it comes to our family. Not when it comes to you, to us, to the life we’re fighting to create.”

I saw Anna nod thoughtfully.

“So… you’ll talk to Michael?” I asked cautiously.

“No,” she said firmly. “We’ll talk to Michael together. He has to hear it from you first. He deserves honesty, and he deserves a choice in this, too. Honestly, I wouldn’t entirely blame him if he refused. Above all, I don’t want to lose him, no matter what. But Jason… thank you. Thank you for being so open about this.”

She leaned over and pressed her forehead against mine. In that moment, the sadness of the past weeks seemed to lift just a little, replaced by cautious optimism.

We had a plan.

Continue to Chapter 42