My Journey Into A Loving Female Led Relationship: Chapter 33

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 33: Anna Pegs Jason Again, And Again

I lie awake, lost in a whirlwind of thoughts. How had I become so fortunate to find someone like Anna? Out of billions of souls, fate had entwined our paths, and I was overwhelmed with gratitude.

Somewhere between dreams and wakefulness, I slipped into sleep, only later to be stirred by the delicate press of soft kisses trailing along the back of my neck. Turning, I discovered Anna still nestled against me, her warm breath caressing my skin.

“Good morning,” she murmured playfully. “My little friend wants you again.”

For a moment, confusion mingled with desire until I recognized the familiar, assertive pressure of the strap-on cock against my ass.

“Pull your legs up and open up for me,” she instructed.

I groaned softly and, without hesitation, pulled my knees toward my chest. Her hand guided the cock to my entrance, its slick head pressing gently against me… prepared with just the right amount of lube, and the remnant of last night’s indulgence.

“Push back,” she ordered.

I obeyed, feeling the cock glide inside with an ease born of familiarity. In perfect synchrony, Anna moved with deliberate grace, slowly thrusting forward until the entire length was claimed by me.

“That’s it, baby,” she murmured, “you have it all again,” her voice a tender command. “It was a lot easier this time.” Then she slowly pulled back and pushed gently in again. “Take that cock… take it for me. We’re just getting started… I love this. I love you.”

Her words spurred me on, and I found a newfound confidence in our shared rhythm. I began a measured dance… pulling away then pressing back, drawing her desire deeper with each motion. I was doing the work now, taking it with deliberate motion. The room filled with the soft symphony of our breathing, gentle moans, and the muted creak of the bed.

Though neither of us reached a climax, I experienced another surge of release… a quiet reminder of our passion. Gradually, I realized Anna had slipped back into sleep, still intertwined with me. Gently, I shifted, allowing the cock to ease out before carefully detaching it from the strap-on; she remained undisturbed in her slumber.

I turned to her, drawing her close into my arms as we shared a few lingering moments of tender intimacy.

Leaving her peacefully asleep, I made my way to the kitchen to begin breakfast. She hadn’t mentioned removing the stockings, garters, and corset, so I left them in place… a silent tribute to her nocturnal allure. I slipped the panties back on. With a cup of coffee in hand, I tiptoed back to the bedroom, placing the cup softly on the warmer atop her nightstand. Her serene face lay peacefully against the pillow, a portrait of tranquil beauty. For a brief moment, I simply watched her, savoring the quiet intimacy of the morning, before quietly leaving the room.

Back in the kitchen, I poured myself a cup of coffee and sat at the table… a little wince at my still sore backside and the nights activity. The house was quiet, the kind of silence that feels comforting rather than empty. As I shifted in my seat, I couldn’t help but notice the lingering sensations from the night before… the still real ache from her discipline and the distinct reminders of the pegging. Strangely, none of it felt unpleasant. In fact, it was the opposite. These sensations grounded me, connecting me to Anna and the experience we had shared.

What surprised me most, though, was the overwhelming sense of contentment that washed over me, a feeling I had rarely experienced with such intensity. It wasn’t just physical; it was something deeper. At first, I couldn’t pinpoint its source. Was it the events of the previous night? Or was it something broader, a reflection of my growing realization of how truly wonderful my life had become?

As I sipped my coffee and allowed myself to sink into those thoughts, the answer became clearer. It was both. The pegging felt like the culmination of everything Anna and I had built together since embracing our FLR. It wasn’t just a single act; it was the physical manifestation of my surrender, of my willingness to let her lead and to trust her completely. Giving myself to her in that way was transformative. It wasn’t about losing control, it was about willingly offering it, knowing she would hold it with care and respect.

The intimacy we shared last night was unlike anything I’d ever experienced. It wasn’t just about the act itself but about what it represented, an unspoken trust, a profound connection, and an affirmation of the life we had chosen together. As I sat there in the quiet morning light, I realized that in surrendering fully to Anna, I had gained something far greater: a deeper understanding of myself, of her, and of the love we shared.

I was finishing up a batch of blueberry pancakes when Anna snuck up behind me. Her hands grabbed my sore ass, making me jump and nearly spill the bowl I was holding. I was still wearing the garters, corset, nylon, and panties.

Anna giggled, leaning in to kiss my neck. “Good morning again, lover,” she whispered, her voice playful and warm.

“Good morning,” I replied, catching my breath.

“You were quite the stud last night,” she said.

“Is that what you call being fucked in the ass?” I said with a smile.

“Pegged,” she corrected and smacked my already sore ass. “And yes, stud. There are not too many straight men who are man enough to allow their lover to peg them and enjoy it.”

I wasn’t sure of that logic but said, “Okay, okay, pegged.”

Her lips curved into a sly smile. “I wasn’t too harsh on you, was I? How are you feeling back there?” She patted my behind.

“Actually, pretty good. I think my preparation really helped,” I said. “But I’ll admit, I was surprised you went with the biggest one.”

“I like surprising you,” she said mischievously. “We all need a challenge once in a while.” Her eyes flicked down, and she added, “I see you surprised me too… keeping your outfit on. You know that drives me crazy.” She punctuated her words with a possessive squeeze of my ass again. “That’s mine now too.”

I let out a sigh. “Uh, it is, for sure. But I wouldn’t mind a little time to recover.”

Anna laughed softly and kissed my shoulder. “Don’t worry, lover. I’ll behave… for now… but tonight is a different story.

The rest of the day, Anna and I took it easy. She wanted me to recover, and I appreciated the thoughtfulness. Still, I knew she’d taken off a couple days from work, but she had called in and extended it to a week. She had enjoyed pegging me and she wanted more time. Her new desire for me wasn’t something she would suppressed for long. While I welcomed the reprieve, there was no doubt she’d claim me again when she was ready. The thought made my heart race with the thought that she truly owned all of me. I had given her all my body could offer… but not all my mind could offer. I was sure Anna had more mental, if not physical, challenges in mind for me.

We spent the afternoon wrapped in the simplicity of each other… making love, strolling through the neighborhood, and enjoying lunch at our favorite little café. When we got home, I ran her a bath, staying close to tend to her. As the warm water soothed her, I gently dried her off with a soft and fluffy towel.

To my surprise, she led me into the shower and began to wash me herself. When I instinctively reached to help, she smacked my hands away with a sharp but playful reprimand. Understanding my place, I lowered my arms and stood silently, letting her take full control.

Her hands moved over my body with deliberate care, the warm water cascading over me as she lathered me up. Every inch of me was touched, cleaned, and claimed, her fingers sliding over my skin in slow, purposeful strokes. When she reached my still-swollen, tender ass, her touch softened, gentle yet possessive.

“Turn around,” she whispered.

I did, and then, without warning, her fingers slipped between my cheeks.

A shudder ran through me as I felt her slide inside. My moan echoed in the tiled space, raw and unrestrained. But still I found myself pushing back toward her fingers.

She giggled, her tone both amused and teasing.

“Something bigger is going to go in there soon,” she murmured. “Once we’re done here, you can go prepare yourself for me again.”

“Yes, ma’am,” I breathed, my voice barely above a whisper.

Satisfied, she slipped her fingers out, turned away, stepping out of the shower and toward the vanity, leaving me there… breathless, aroused, and utterly hers.

Standing at her vanity, she hummed softly as she leaned forward to smooth cream onto her face. The motion made her hips shift slightly, and my eyes were irresistibly drawn to her curves. Her body, as familiar to me as my own, still left me in awe. There wasn’t a part of her I didn’t adore, but her rear? It was a masterpiece. It made my heart race every time I saw it… clothed or naked.

I hesitated for a moment before giving in to temptation. I walked over quietly and dropped to my knees, then, as I had done with Sally in this same position weeks earlier, I pressed my lips against the soft skin of her backside. I suppose I had really become an “ass” man, in more ways than one.

Anna giggled and wiggled in response to my kisses on her cheeks, but made no move to stop me. Encouraged, I grew bolder, planting kisses and slowly parting her cheeks.

My lips and tongue moved with purpose between her cheeks, and I caught the sharp intake of her breath. That sound… her pleasure… was all I needed to push myself harder, more eagerly. She moaned softly, pressing back against me, and then as my tongue slipped inside, I knew I was giving her exactly what she craved.

Her enjoyment only fueled my hunger, every sound and movement deepening the connection between us. My tongue explored her thoroughly, pressing deeper, tasting her, worshipping her. She writhed under my attention, her breath quickening, her moans growing more desperate.

Without touching herself, she pushed back, reaching around and grabbing my head, she began to shake, her body seizing as a climax overtook her. I didn’t stop… I couldn’t. I held her close, my tongue relentless, drawing out every last shudder, every last tremor of her release until she finally went still, spent and satisfied beneath me.

Anna finally turned toward me, still on my knees. Her smile was radiant as she cupped my cheek. “You are amazing,” she said softly. “You’re wearing me out.”

I laughed and said, “I didn’t think I would ever hear that.”

I helped her into the bedroom and gently laid her down on the bed. Leaning over, I kissed her tenderly on the cheek. “I’ll fix us a light dinner,” I murmured.

She smiled, her voice teasing as she replied, “Then get ready again for me.”

I nodded, knowing exactly what she meant.

After we ate, Anna went to the bedroom for some personal time. I cleaned up the kitchen and then took care of my preparation.

I was in the kitchen getting out a bottle of wine when I heard her footsteps. I turned to see Anna standing in the doorway, her bare body illuminated by the soft glow of the kitchen light. My breath caught in my throat. She wore the strap-on, already prepared for what she wanted next. Her confidence and beauty made my heart race.

“When you’re done, meet me in the living room,” she said, her tone firm but warm. “I want to take you in front of the window.”

Her words sent a wave of nervous excitement through me as I watched her turn and walk away, her hips swaying with purpose. I could see in the reflection of the window the strap-on dildo swaying in front of her… it looked even larger.

I put the wine away and joined her. She was silhouetted by the lights of the city as she stood near the large windows. With the attached strap-on in her hand she spread lube over it with careful precision.

The moonlight poured into the room, casting her in a silver glow, while the city lights twinkled beyond the glass.

We kissed deeply, the only thing separating us was the smooth surface of the strap-on pressing between us. The world outside continued as if nothing had changed, but for me, everything was different. I had given myself to her fully, and she had taken me in every sense of the word.

“Are you ready?” she asked softly, her gaze searching mine.

“Yes,” I whispered, the single word carrying all the trust and desire I felt.

She guided me to the padded stool we often used for discipline, its soft leather cool beneath my skin. “Lie over it,” she instructed, her tone both commanding and reassuring.

I obeyed, feeling her presence as she stepped behind me. The anticipation and intimacy of the moment were almost overwhelming.

I felt her press the head of the cock to my ass. I moaned softly as she slipped into me again, this time without hesitation. She was commanding as she stood behind me with the long, life like cock, deep inside me. She began to move slowly at first, getting her balance and using the strength in her legs to drive the shaft deep into me. Her movements were firm, steady, and unrelenting.

Though I was still sore, it felt easier now, my body adjusting to her. The sensation of fullness and deepness overwhelmed me again, but this time, it came with a surprising sense of calm. There was no separation in my mind between the strap-on and her… it felt like an extension of her, a part of her claiming me completely.

“How’s that, baby? Is it okay?” she asked, her voice gentle but probing. Her words were separated by little grunts as she continued to work.

“Uh… yes… it’s good,” I managed to reply, my voice laced with both pleasure and vulnerability.

She leaned down, her breath warm against my ear as she whispered, “I’m going to take you hard now.”

“Yes,” I breathed, my response filled with trust and longing.

A moment later, her hips began to move faster, gradually gaining speed and intensity. She was relentless, taking me with a sense of ownership that left no doubt that I was hers.

I pushed back against her, matching her rhythm as best I could, silently communicating my readiness to take everything she gave. Her pace quickened, and I felt her power in every thrust. My penis was straining mightily against the cage. Even when I moaned that I was spending fluid again, she didn’t relent.

“Yes,” she murmured, her voice raw with desire. She climaxed. “Yes, yes, yes.”

She continued pounding me until there was nothing left in either of us, the exertion leaving us both spent and breathless. When she finally stopped, she leaned down and kissed the back of my neck softly, a gesture as tender as it was possessive.

She slowly pulled out of me, leaving me still gasping for breath, my caged penis still swollen as it was before it all began. In spite of the fact that I had only drooled prostate fluid, I felt a pulsing deep inside. It was strangely satisfying.  

Over the next several days, we stayed mostly naked, rarely leaving the condo except for necessities. It felt like the outside world had disappeared, leaving only the two of us in our private universe.

Anna was like a kid in a candy store… where she had the choice of all the sweets she could eat. She took me in every room, on nearly every piece of furniture, exploring every facet of our connection. When she wasn’t taking me, I was pleasuring her with my mouth, eager to give her everything she wanted. Between the passion, intimacy, and then recovery, there was little time for anything else, and neither of us seemed to mind. We were truly like newlyweds on their honeymoon.

This was a turning point for us. She had claimed me completely, in every way, and I knew she would never let me go. The thought didn’t scare me; it thrilled me. I loved her for her strength, her passion, and the way she embraced me so fully. I loved her, and I loved belonging to her. I felt I had given her something unique that she truly enjoyed but would never find it from anyone else. It was a gift to her that would last forever.

After that day, pegging became a regular part of our lives. Anna pegged me at least once a week, sometimes more. I had been stretched to accommodate her. She joked… with some evidence… that my anus had changed shape and appearance, calling it her boi-pussy. I couldn’t see the difference myself, but I could certainly feel it. The sessions lasted longer, and Anna took them on with unbridled passion. They were no longer painful; in fact, I craved them… not just for the physical pleasure, which mirrored the tease-and-denial dynamic, but for the deep intimacy they nurtured between us. 

The only thing I could compare it to was when I used to fuck her, but there was a difference. Back then, though I wanted her to enjoy it, like most men, my own pleasure had been the focus. But now, my little penis had been taken out of the equation entirely. My pleasure came solely from hers. Yes, my little guy would leak, but that was just a natural consequence of her stimulating my prostate, and never a true climax. In this new dynamic, it was clear: I have given something to Anna and she had definitely “made it better.”

Anna had so enjoyed our mini-honeymoon that she decided to take a few more days off. This time she decided that we were going to go on a camping trip… which surprised me as we hadn’t done that in several years. This time she said the destination would be a surprise.

During the “honeymoon,”Anna and Jason decided to extend the honeymoon and take a camping trip. I’ll be skipping over the camping trip for now. On the trip they met two women. That experience deserves more space than I want to devote here, and I plan to explore it in a separate set of chapters once this section is complete. Instead, I’ll continue with what followed after the trip… which was momentous to say the least.

To Be Continued