My Journey Into A Loving Female Led Relationship: Chapter 45

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 45: Anna Tells Michael That She Wants Him to Take Her Anal Virginity, Michael Fucks Her Ass

Anna had planned to speak with Michael that Friday evening about taking her anal virginity. I wasn’t sure why, but I was nervous—uneasy in a way I couldn’t quite explain. I had no doubt he would agree. Still, the significance of it weighed on me. This wasn’t just another night. This was something new. Something more.

Anna had started preparing the day before, and, to my delight, had allowed me to help. After her shower, I’d been invited into the bathroom to kneel behind her. I eagerly spread her cheeks and spent long, worshipful minutes with my tongue, tasting and teasing her. When she was ready, she handed me the small anal plug. Slipping it into her was almost ceremonial… intimate, sacred. A quiet obedient act that made me feel connected to her in a way nothing else could.

After dinner, Anna and Michael moved to the sofa as they usually did, settling into their familiar ritual. I stayed in the kitchen, tidying up the last of the dishes while sneaking glances through the open archway. They were already making out, lips locked, bodies pressed close. I didn’t know exactly how intense their foreplay typically got before heading to the bedroom, but from where I stood, it looked like they were already burning hot. Then again, knowing Anna, I couldn’t shake the feeling that part of it was for me… a deliberate tease. She knew I was watching. And she knew what it did to me.

As I stole another glance, I saw Anna’s subtle hand movement. My stomach clenched. I recognized that motion instantly. She had his cock out, stroking it slowly and deliberately.

I shifted slightly, aligning myself just enough to catch the mirror’s reflection.

The sight sent a jolt through me.

Anna’s fingers were wrapped around Michael’s thick shaft, stroking him with slow, confident strokes. Her blouse was hanging open, her breasts bare, nipples firm. Michael’s hands moved over them, teasing gently as their mouths remained locked in a deep kiss. It was intimate and bold, and like I had witnessed before, it was unfolding right there in front of the windows, the city lights casting their silhouettes in golden flickers.

Then, without breaking rhythm, Anna slowly lowered herself. Her lips parted, and she took him into her mouth. Inch by inch, she slid down, deeper and deeper, until her lips touched the base of his shaft. No hesitation. No falter. Just complete, practiced control.

My breath hitched.

The intensity of it, the raw beauty of her submission and skill, shook me. I stood frozen in the kitchen, heart pounding, my caged cock aching violently. It was all too much—the scene, the sounds, the reflection. Watching her like that, bold and beautiful, giving herself so fully to him… I swear, I nearly climaxed just standing there.

The image was burned into my mind… so erotic, so intimate. If I could have frozen that moment in time, captured it in a picture, I would have framed it and stared at it every day.

My ears perked up the moment Anna spoke.

“Michael, I have something I want to ask you,” she said, her voice soft but deliberate. Calm, composed, but with an unmistakable edge of purpose. “It’s perfectly okay if you don’t want to, but… I want to give you something very personal. Something I can never give to anyone else.”

Michael shifted slightly, intrigued. “What is it?”

Anna paused, letting the silence stretch, letting the anticipation bloom. She had a way of turning even a casual conversation into something charged—intimate, theatrical, irresistible. Finally, she said the words.

“I want you to take my anal virginity.”

A sharp breath escaped my lungs. I had known it was coming… we had talked about it, fantasized about it—but nothing had prepared me for the raw electricity of hearing her say it out loud. The words hit like a jolt. No amount of imagining could have matched the real thing.

Michael’s eyes widened. “What?” he asked, blinking as if he hadn’t heard her right. I saw him glance over at me, as if looking for a signal… approval, hesitation, concern. I simply shrugged. I didn’t know what he expected from me. This wasn’t my moment. It was hers.

Anna didn’t break her rhythm. Her hand continued moving slowly, almost absently, along the length of his cock. Her voice remained steady. “Yes,” she said. “I’ve already taken Jason’s, and I loved it. That’s when I realized… I could give mine to you. Consider it a thank-you… for the beautiful gift you’ve given me. For helping create our child. But if it’s not something you’re into, that’s okay. I won’t bring it up again.”

She gave him an out, of course… classic Anna. But I already knew what Michael didn’t yet realize: she was orchestrating this moment with precision. He was already saying yes in his mind.

And who could blame him? I knew Michael wasn’t insane—and like most men, he’d probably dreamed of taking a gorgeous woman’s ass at least once. And Anna… Anna wasn’t just any woman. She had that rare gift… like in the song “Take Forever”… everything sexual she did, she made unforgettable. Better.

Michael was still reeling, trying to catch up. This clearly wasn’t something he’d ever expected from her.

Anna tilted her head, watching him. “Have you ever done it?” she asked gently.

“Uh… no,” he said, his voice faltering. “But… yeah. I mean, if you’re sure…”

She smiled then, a deep, confident smile, full of heat and certainty. “I’m totally sure. In fact…” she leaned closer, her voice a sultry whisper, “I’ve already started preparing. Just in case you said yes.”

Then, without any hesitation, Anna stood up.

She turned her back to him, and in one smooth, casual movement, slid down the loose harem pants she’d been wearing. She bent forward just slightly, just enough to make her intent obvious. The soft glow of the living room lamps reflected off the jeweled base of the plug nestled perfectly between her cheeks.

Michael’s breath caught audibly. “Fuck,” he said, voice thick with disbelief and arousal.

Anna giggled and gave her hips a playful wiggle. “I’ve been keeping a plug in as much as possible,” she said teasingly. “I think I’ll be ready by next Friday… if you’re willing.”

But we all knew she already had her answer.

This conversation… every glance, every pause, every gesture—had been a performance. A seduction. Not just for Michael, but for me as well. She had orchestrated the entire moment like a slow-burning piece of erotic theater.

And it was working.

Michael finally found his voice. “Of course. Of course. I mean… I’m honored that you’d consider doing that for me.”

Anna smiled warmly. “Thank you, sweetheart. I know you’re going to love it,” she said, her voice laced with both affection and mischief. Then, with a teasing glint in her eye, she added, “Just be gentle with that big cock of yours.”

Michael exhaled shakily, his body visibly tense with anticipation.

I, on the other hand, glanced down and saw my poor caged penis dripping like an open faucet onto the tile floor. I was going to have to clean that up. Quickly.

Anna giggled and looked at Michael. “Tonight, I want you to take my pussy with the plug still in my ass. However, it might be a pretty tight fit.”

I gasped, and from the corner of my eye, I caught the flicker of surprise on Michael’s face. Anna never ceased to shock me… or him.

Then they stood up, and I was once again reminded of just how exposed Michael was. His cock, still hard, loomed large and so much bigger than mine. They kissed deeply, his cock pressed between them, a passionate exchange that left no doubt about what was to come. As their lips parted, Anna reached down, curling her fingers possessively around Michael’s thick shaft, and, with a knowing wink in my direction, led him toward the bedroom.

As always, I retreated to my own room, eager to listen. I was never disappointed. After a few minutes of hushed movement, Anna’s moans filled the air, raw and uninhibited. I could picture Michael easing into her, his long shaft stretching her while the plug remained firmly lodged inside, only a thin sheath of flesh separating his cock from the unyielding toy. The rhythmic creak of the bed soon followed, mingling with their urgent, breathless sounds. They were lost in each other, and I was lost in them.

Later, when Anna invited me to her room for her cleaning, I was surprised to see she was still wearing the plug. I didn’t hesitate. Crawling between her legs, I began my duty, my tongue worshipping her as she lay back, spent and satisfied. I made a point to press my chin against the plug as I worked, feeling the firm resistance as I licked and teased. It didn’t take long before I heard her breath hitch, her body tensing, and then… she climaxed. Hard.

When she was satisfied, she exhaled deeply, stroking my hair absentmindedly before instructing me to remove the plug. I did so gently, relishing the way she shivered as I slid it free. Then, without a word, I took it to my bathroom to clean. A few minutes later I was on my bed when Anna came in.

A few minutes later, I was lying on my bed when Anna slipped into the room.

She climbed in beside me, her body warm against mine, and whispered, “I think Michael likes the idea.”

I smiled. “Who wouldn’t?”

“He really outdid himself tonight,” she said, grinning. “He really filled me again.”

She leaned in to kiss me, quick, playful, and then without another word, straddled my face.

She wasn’t lying… he had really filled her.

By now, I had come to expect that each cleanup would be a little less than the last—a subtle sign of Michael’s body adjusting to the routine. But this time… this time, it was every bit as much as the first. Thick. Fresh. Abundant. Even after all this time, Anna could still stir that kind of release from him. Somehow, she always managed to draw it out of him.

Even during her last visit to me, there had been more than usual. And now… I could taste the truth.

Anna still had complete control—not just over me, but over him too. We were both captive by her, although in very different ways.

The following week, I think I was just as nervous as Anna when Michael arrived. She had me insert the largest plug inside her, and I could tell from the way she shifted, the soft little gasps that escaped her lips, that it was stimulating her. She was already aroused.

Then she emerged from the bedroom, and both Michael and I were left breathless.

She was a vision in white… a white bustier that lifted her breasts, the fabric barely covering her nipples, leaving most of the soft curves exposed. White garters hugged her thighs, connected to sheer nylons that accentuated the long, elegant lines of her legs. She also had on a pair of sheer panties. Her white high heels added to the effect, making her presence even more commanding, her posture poised and deliberate. Draped over her shoulders was a sheer white shawl, a gossamer tease that did little to hide the gorgeous body beneath.

She radiated confidence, seduction, power.

Michael and I could only stare.

She smiled knowingly, reveling in the effect she had on us.

After a light dinner, they settled into their usual foreplay on the sofa, their routine both familiar and electric. As always, Anna asked me to refill their wine glasses. When I returned, as always, I was met with a sight that sent a shiver through me… Anna had Michael’s cock in her hand, stroking it slowly, teasingly. It would never get old for me.

She looked up at me, her eyes dancing with mischief, and then, without breaking eye contact, she dipped her head, taking him into her mouth.

I stood there, utterly transfixed as she worked him over with practiced ease, her lips gliding down his length, then deeper still, until she had him all. Michael leaned back against the sofa, his eyes closed, his fingers threading through her hair as he let her pleasure him.

I nearly knocked over a wine glass, my hands trembling as I watched from up close, enraptured. She was completely lost in him, in the moment, as if I wasn’t even there. But I was. And it was affecting me more than I could have imagined.

Michael moaned, his grip tightening on her head. Then to my shock, his hips lifted, pushing deeper, and I knew he was finishing inside her throat. I could see her throat actually pulsing as his cock throbbed deep in her throat. My poor penis was pulsing wildly too. I had never witnessed this before… never seen her suck him to completion.

Anna took it all, holding him deeply until he was completely spent. Only then did she slowly pull back, licked her lips. His rapidly wilting cock slipping out of her mouth. I knew there was nothing in her mouth… it had all gone directly down her throat.

I hurried back to the kitchen, shaking with excitement, my heart pounding in my chest. I couldn’t believe what I had just witnessed… what she had allowed me to witness.

When I dared to look back, Anna was sitting up, her lips curling into a knowing smile. She met my gaze, then ever so delicately wiped the corners of her mouth, as if savoring the moment.

She looked so beautiful, so radiant, so in command, that it made me shake even more. God, I loved this woman.

I watched as Anna once again led Michael to the bedroom, her fingers wrapped possessively around his hand. Then, to my surprise, she motioned for me to follow.

Hope flickered inside me. Was she finally going to let me stay for the main event?

But it wasn’t to be. This time, there would be no plug in Anna’s ass. This time, it would be Michael’s cock. How I would have loved to watch that.

She allowed me to remove the plug, a moment of quiet intimacy between us, but once the task was done, she dismissed me with a look. My place was elsewhere.

Reluctantly, I withdrew to my room, my mind spinning.

That’s when it hit me… Anna hadn’t just pleasured Michael earlier for fun. She’d done it with intention. She wanted him to last. She wanted to make sure he had every ounce of control when he finally took her ass.

As with the week before, the bedroom was silent at first, eerily so. But slowly, inevitably, the sounds began to rise… soft moans, the low thrum of breathless groans. Then, cutting through the quiet, came a sudden high-pitched cry from Anna.

My breath caught.

That had to be it. Michael was inside her. His cock was in her ass.

The soft, rhythmic squeaking of the bed followed… familiar, steady… but it was quickly overtaken by Anna’s voice. Raw. Urgent. Ecstatic.

“Fuck my ass hard.”

The words shot through me like electricity.

There was no more wondering, no more waiting. He had done it. Michael had taken her anal virginity. She had given it to him freely, fully. It belonged to him now… forever.

And in that instant, hearing her surrender so completely, I swear I nearly climaxed inside my cage.

To Be Continued