My Journey Into A Loving Female Led Relationship: Chapter 44

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 44:  I Clean Anna With Michael There, Ann And I Share The News of Her Pregnancy, Anna Tell Me She Wants To Give Michael Her Anal Virginity

After we discovered Anna’s pregnancy, we invited Michael over to share the news.

We were both nervous—buzzing with excitement, but also aware of how unusual this moment was. This wasn’t a typical pregnancy announcement. It wasn’t a wife telling her husband she was expecting. This was my wife and me preparing to tell her lover that he had gotten her pregnant.

When he arrived, things didn’t unfold as they usually did. There was no kiss at the door, no immediate retreat to the bedroom. Instead, Anna greeted him warmly, then asked him to join us on the sofa. I caught the flicker of uncertainty on Michael’s face—he looked curious, a little cautious—but he smiled and followed her into the living room.

I stepped in carrying three glasses, placing them carefully on the coffee table. Michael raised an eyebrow, clearly surprised. I hadn’t poured anything yet—there was a chilled bottle of champagne waiting in the kitchen, hidden for just this moment.

Anna and Michael settled on the couch, and I sat across from them. What Anna didn’t know was that I had prepared a little surprise of my own… a special way to share the news.

From between the cushions, I pulled out a small gift box, neatly wrapped and tied with a bow, and handed it to Michael.

He looked confused but amused. “What’s this? It’s not my birthday.”

Anna turned to me, visibly surprised by the gesture, but said nothing. I simply smiled. “Open it,” I said.

Michael peeled away the paper and opened the lid of the box. At first, his face was blank, trying to process what he was seeing. A little plastic device with two red lines. Then realization struck. He looked up at me, then at Anna, eyes wide.

“You’re… you’re pregnant?”

Anna’s face lit up, beaming with joy. “Yes,” she said, her voice trembling with happiness. She practically launched herself into his arms, laughing, hugging him tight.

They embraced, then kissed—deep and passionate, full of the energy and intimacy of the moment. I watched, heart full, breath caught in my chest.

When they pulled apart, all of us were still catching our breath.

“Congratulations,” Michael said, grinning. “I’m so happy for you two.”

Anna laughed, her eyes shining. “We literally couldn’t have done it without you.”

I hurried to the kitchen for the champagne. A moment later we were sharing a toast to new life, love, friendship, and happiness.

The room filled with laughter and warmth. In that moment, Anna made it clear that Michael was no longer just her lover. He was family now. Always welcome. Always part of this new, beautiful chapter in our lives.

Of course, Michael’s own marriage placed limits on his availability, but he continued to visit every Friday night… sometimes having the opportunity to make a mid-week visit

I would prepare dinner, and the three of us would eat together, talking easily, sharing laughter, and building a rhythm that felt natural, even comforting. The only difference now was what came afterward. When the meal was done and the dishes cleared, Anna and Michael would retire to the living room, and their lovemaking would begin.

I would busy myself with the dinner dishes, trying to keep my hands occupied, but my eyes often betrayed me. I couldn’t help glancing toward the living room, where they would be seated on the sofa, wrapped in each other’s arms. Their silhouettes, bathed in the amber glow from the city lights beyond our towering windows, made the moment look almost cinematic—beautiful, intimate, and utterly real.

The first time I truly saw them like that, I had made an excuse to walk over… delivering a couple of after-dinner drinks. What I found left me stunned.

Anna had worn a delicate silk kimono for dinner, soft and flowing, the fabric clinging to her curves with every step she took. Now it was open, exposing all of her amazing charms. Michael was nestled against her, his mouth on her breasts, sucking gently, reverently. One of his hands was between her legs, and hers was wrapped around his cock… stroking him slowly, affectionately.

She opened her eyes and looked at me.

Her smile was genuine… soft, playful, warm. She glanced down briefly at the thick, hard cock in her hand, then up again at me… and my tiny, caged penis. I felt it twitch inside its steel confinement, pulsing helplessly in response. That single look from her sent a jolt through me, equal parts longing, submission, and pride.

By then, I had long since returned to my usual home attire… wearing nothing but my cage. It had taken a bit of adjustment, for both Michael and me. At first, the vulnerability of it was overwhelming, even awkward. But over time, it became normal. Natural. Expected.

There was no ambiguity about my role once they moved to the bedroom. Anna expected me to perform my cleanup duties, even with Michael still lying beside her.

At first, like many things in our journey, it felt awkward, especially between him and me… but Anna had a way of making everything feel inevitable, even elegant. Although I had told Michael about my duty to clean her, we never spoke of it. We didn’t need to. This was Anna’s world. She set the rules, and we both accepted them.

She still didn’t allow me to watch them together. That boundary remained firm. But when it was time, she would text me, and I would come in to do what she expected. And over time, what had once been an act of submission tinged with humiliation became something else entirely. A ritual. A moment of connection. I began to anticipate it.

I remember the first time I was invited in while Michael was still in bed with her. Of course, I had seen them together during the weeks we were trying to conceive—but this was different. This wasn’t about function. This was about something enduring.

When I stepped into the room, my face flushed with heat. He knew, of course, that I cleaned her. But he had never been present for it. I expected it to feel unbearable.

Michael lay still, eyes closed. But I suspected he wasn’t truly asleep. It was his way of giving me space, of pretending not to witness something that was, in truth, deeply personal. If I could’ve, I would’ve shut my eyes too. But there was no avoiding the sight in front of me.

Anna, my beautiful wife, lay naked beside him, her head resting on his chest, one hand still gently draped around his softening length. Her skin was flushed, her chest and breasts bearing the faint marks of his whiskers, small red trails that told the story of their passion. She looked content. Satisfied and above all, well fucked.

And there he was, Michael, the man who would be the biological father of our child. His penis, even in its relaxed state, was thick, heavy… and still larger than I was at my most aroused. Traces of their coupling clung to his shaft. The sight struck me with force, raw and primal. I tried to shake it away, but all it did was intensify the tight ache building inside me.

I moved quietly, careful not to disturb the illusion of Michael’s slumber. Anna turned her head, catching my eyes with a smile… tender, inviting, in full control. Without a word, she parted her legs.

I swallowed hard, took a breath, and climbed onto the bed. Settling between her thighs, I lowered myself onto my stomach. Her pussy looked like it always did after their coupling… swollen, stretched and very, very wet. I started by pressed my lips to the warm skin of her inner thigh, inhaling the scent of their union. Anna’s hand came to rest gently on my head, guiding me closer, and I surrendered to her touch.

I glanced up, and for a fleeting moment, I saw something transcendent in her expression… it was pure, unfiltered bliss, even before I had begun. That’s when it hit me: at that moment, she had two things that gave her the most pleasure… his spent, satisfied manhood, and my devoted mouth.

A soft moan escaped her lips as I began my work. Normally, when she came to my room, she would squat over me, making the cleanup routine swift and efficient. But lying on her back like this, still tangled in the aftermath of her passion, made the task more challenging… yet far more intimate. I worked slowly, thoroughly, my tongue exploring her until I found exactly what I was searching for deep inside. She gasped, her hips shifting, as I licked and sucked her sensitive flesh.

It took much longer than usual to complete my duty, but that only gave me more time… to taste, to pleasure, to bring her to the peaks of ecstasy again and again.

When I finally finished, I quietly slipped away, leaving them to their shared afterglow. The second and third times they coupled, followed a familiar pattern… she would come to my room, where I would take care of her in our usual way. Sometimes she brought my gift in her mouth, sharing a passionate kiss.

This became our rhythm: once in her bed, twice in mine.

Michael and I never spoke about this new arrangement, yet in the moments when I entered the bedroom, no longer were his eyes closed and he would acknowledge me with a subtle glance. I did the same in return. It was an unspoken understanding, a silent agreement that made everything easier… for both of us. This was what Anna wanted and this is what we would do.

Beyond that, it took some time to adjust to their intimacy unfolding in the living room while I remained in the kitchen, cleaning up the dinner dishes. No matter how much I tried to focus on my task, I couldn’t help but glance into the room, catching glimpses of them kissing… moments that would inevitably lead to their retreat into the bedroom.

I had grown accustomed to seeing them kiss, and when I brought them wine, it was common to find Anna’s blouse undone, her flushed face revealing that Michael had been teasing her breasts. But the first time they went further in front of me was a shock.

At first, it seemed like any other evening… Michael and Anna sitting together, their lips locked in an intimate embrace. Then, suddenly, her head dipped out of sight. I froze, my heart pounding as I heard Michael’s deep moan, followed by the unmistakable sounds of Anna pleasuring him with her mouth.

It was far more intimate than simply listening from my bedroom. From my vantage point, I could hear everything… the wet, rhythmic sounds, the slight shift of the couch as they moved. I even caught a faint reflection in the living room window, a ghostly outline of Anna’s head bobbing in his lap. The most unmistakable sound of all, though, was the distinct noise she made when she took him deep into her throat.

Naturally, my poor, neglected penis reacted, throbbing and dripping uncontrollably. It was exquisite, agonizing torture… pure yet unbearably erotic. And then, as if to tease me further, Anna finally lifted her head, glanced over the back of the sofa, and met my gaze. Her lips glistened in the dim light, her mouth still wet from him. She smiled, winked… and in that moment, I knew she had done it as much for me as for Michael.

Strangely, I found myself wondering what it would be like… to perform oral on a man. I had no desire to be with one sexually, yet the intimacy of the act intrigued me. It wasn’t arousal in the traditional sense, but rather a fascination with the level of submission and connection it seemed to create.

I recalled the night Anna had first brought up the vague idea of me using my mouth on Michael. It was during one of our usual routines… when she came to my room for me to clean her up. Her words had shocked me to the core, rattling something deep inside me. At the time, I had dismissed it, shoving the thought from my mind as quickly as it had surfaced. I wasn’t gay and had no desire for another man.

I took comfort in the belief that no matter what, I was almost certain Michael would never allow it.

Several nights later, as we made love on the sofa, Anna shocked me again. Her expression shifted… serious yet undeniably mischievous. I recognized that look immediately. It meant she had something on her mind, something she had already decided.

“Jason,” she murmured, her fingers tracing slow circles on my chest. “I’ve decided I want to give Michael something special.”

I raised an eyebrow, intrigued but unsure where this was going.

“He’s been such a rock through all of this,” she continued. “Never hesitating, never questioning any of my requests… especially the one that made me pregnant. He’s special to both of us. We’re linked forever now.” She paused, holding my gaze. “I want to give him something I can never give to anyone else. Something you’re very familiar with.”

I stared at her, confused, my mind racing to decipher her meaning. I shivered, thinking it was about her comment that she wanted me to pleasure Michael with my mouth. It wasn’t.

Seeing my bewilderment, Anna smiled knowingly.

“I want to give Michael my anal virginity… like you did for me.”

I was shocked, if not a bit relieved. Still, the words hung between us, weighty and deliberate.

“When I lost my virginity, it wasn’t anything special,” she admitted. “Just a couple of kids fumbling around in the backseat of a car. I hadn’t planned it, but I didn’t resist it either. I was too young to understand how precious it was. If I could go back, I would have given it to the man I married.” She squeezed my hand gently. “But now, I have the chance to give something truly special to Michael.”

I swallowed, still processing her words. “Uh… have you spoken to Michael about this?”

“Not yet,” she said, flashing a playful smile. “But I’m sure he’ll agree.”

I was sure of that as well.

“So, I want your help,” she added.

“Me?” I asked, my pulse quickening. “How can I help?”

Anna’s smile widened. “Well, first, you can order me my own set of plugs. I already have a perfect dildo, so I don’t need another one of those. I want to start practicing as soon as possible.”

I grinned. “I’ll order them by express mail today.”

The package arrived the next day. Like me, Anna had chosen a set with three sizes—three, five, and seven inches. They were identical in style to mine, only larger around with the longest one also being 2 inches longer than my longest one. I was surprised at the sizes she had chosen, but I knew better than to question her determination.

When she arrived home from work, I had her wine ready, and as she sipped, I massaged her feet. Once I was done, I reached under the sofa, retrieved the box, and opened it in front of her.

Anna’s eyes lit up as she examined the plugs. She chuckled, turning them over in her hands. “I love that they have the colored crystals on the end,” she said, admiring them. Then, with a decisive nod, she added, “I suppose I should start with the smallest, like you did.”

She glanced at me, her eyes sparkling with intent. “Let me go get prepared, and then you can come in and put it in for me.”

I blinked in surprise. “Really?”

“Really,” she confirmed, standing up and heading to the bedroom. “I’ll text you when I’m ready.”

It felt like an hour, though it was probably half that, before my phone finally buzzed. The message was simple: “Ready.”

My stomach flipped as I hurried to her bedroom. Knocking lightly, I heard her voice from inside. “Come in.”

I stepped inside, breath hitching as I took in the sight before me. Anna was lying on her stomach, completely naked, her gorgeous backside on full display with a pillow under her hips. My heart pounded as I paused, taking a moment to steady myself before moving closer.

She glanced back at me, a soft smile playing on her lips. “Start with your tongue.”

I sucked in a sharp breath, shivering with excitement. Setting the box aside, I crawled onto the bed, settling between her legs. She spread them slightly, inviting me in, and I began planting slow, reverent kisses across her cheeks. She moaned softly, melting into my touch.

With a gentle hand, I parted her, revealing the delicate rosebud nestled between. My tongue found its target, and she moaned again, arching slightly as I went deep. I pleasured her thoroughly, taking my time, savoring every reaction. She came several times before I finally pulled away, breathless.

I reached for the lube but hesitated, uncertain if I was allowed to apply it myself.

Anna, sensing my hesitation, murmured, “Go ahead. Lube me up.”

A thrill ran through me as I scooped the cool gel onto my fingers, spreading her open once more. Slowly, I slipped one finger inside, feeling the tightness yield slightly as she moaned. It was like nothing I had ever felt before… tight, but soft and pliable. Gently, I worked the lube into her, adding a second finger, stretching her carefully before pulling back.

Reaching for the smallest plug, I coated it generously, then positioned it at her entrance. Gently again, I pressed forward. Her body resisted momentarily before yielding, drawing it in inch by inch. I paused, waiting for her reaction.

Anna let out a deep, shuddering breath, then wiggled her hips slightly. “Go on,” she urged.

I pushed again, and suddenly, it slipped fully into place.

Sitting back, I wiped her clean before watching her roll onto her back and sit up. She shifted slightly, testing the sensation, then grinned. “Wow… that feels really weird… but not bad.” She stretched, running her fingers over her stomach. “I’ll wear it for as long as I can. I want to be ready in a week for Michael.”

“A week?” I asked with surprise.

She smiled and said, “That should be plenty of time. The truth is, I don’t want to be completely stretched. I want to feel it, like I was truly a virgin again.”

I nodded, still absorbing everything that had just happened. “When are you going to tell him?”

“This Friday, when he comes for his regular visit,” she said. A playful gleam flashed in her eyes. “I might even have it in when he gets here.”

I shook my head, smiling at her tenacity. I envied Michael.

To Be Continued