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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 31: Pegging, Jason Gets Disciplined, Anna Takes Jason’s Anal Virginity
We arrived home after ten, and I was a nervous wreck. It almost felt like I was a virgin all over again. Anna had delayed giving me my discipline, deciding instead that it should come first… before she took me. She believed it was appropriately submissive for my ass to be lined with welts before surrendering my anal virginity.
Once we were home and settled, we moved to the living room in front of the large windows. The night was clear, the stars twinkling above us. A full moon illuminated the space, allowing us to leave the lights off, adding to the atmosphere.
Anna kept her suit pants on but removed her jacket and blouse, freeing her beautiful breasts. The sight of them alone was enough to make me hard, but this was not the time for arousal… this was time for discipline. As always, I was nervous, but tonight, the anticipation was even greater.
She unsnapped my garter straps to keep them from interfering, her movements slow and deliberate. Then, I bent over the special stool and positioned it for her convenience. She hadn’t restrained me… she didn’t need to. I was hers, utterly and completely.
Tonight, she had decided on a combination: fifteen strokes with the paddle followed by ten with the cane. My skin had fully healed from previous sessions, so I thought I was ready. But no matter how many times we did this, the pain always took me by surprise.
I felt her pull my panties down to my knees, leaving me exposed. Looking back, I saw her breasts swaying with her movements, mesmerizing and powerful. She stood behind me, the paddle in her hand, slapping it against her palm. The sound was sharp, echoing in the room, and making her breasts jiggle tantalizingly. It was deliberate, a ritual… a preview of what was to come.
I closed my eyes, sinking into the moment. I felt Anna’s presence, her authority enveloping me completely. She let the anticipation build, drawing out my submission. I wanted to go into my subspace, but it was too soon.
She could see how tense I was.
“Relax,” she said, her voice low and commanding. “It will be over before you know it. I want you to feel my power now so that can feel my thighs slapping against your disciplined ass later.”
I swallowed hard, trying my best to obey, to relax, but it was nearly impossible. My mind raced, worrying about the plug disengaging, about enduring what was to come. But I knew one thing for certain: I was exactly where I belonged, under Anna’s control, completely at her mercy.
A moment later I felt the first splat with the large wooden paddle with holes in it. The holes made it hurt even more. Anna showed no mercy, ensuring that this would be a night I would never forget. I made it through the first fifteen without losing the plug, but my ass was very red and swollen already. It was more difficult when she started with the cane. As the doctor had recommended, Anna paused after using the paddle. She stood behind me, her hand running slowly over my swollen ass. I moaned, more in anticipation of what was coming next more than from any perceived pain from her hand movement.
Anna walked slowly over to the punishment chair and sat down. I could see that she was breathing heavily. I knew she was excited. She then lifted up, pulled off her pants and sat back down with her legs spread. She motioned me over. I didn’t think this was part of the plan and was pretty sure it was because of her excitement of what the evening held.
I crawled over, feeling my swollen ass with every movement. I knew what she wanted… needed. I moved between her legs and brought my mouth to her. She was, as expected soaked. She moaned and wrapped her legs around my neck. Her thighs covered my ears but I could still hear her moans of pleasure. I got her off several times before she ordered me back to the stool… to wait for the next phase of my discipline.
I lay there for what seemed like hours, but was probably less than an hour. My ass was still swollen and red and I knew still just as tender as when she left me. I heard her footsteps. I saw her pick up the cane and then swish it through the air. I shivered and I knew Anna could see it… could feel my submission. That was what she wanted. She wanted me feeling as vulnerable and submissive as possible in preparation for what was coming after the caning was done.
I had lost count of the strokes and I was nearly at my breaking point when the last stroke hit. I knew it was the last one because it was the one she always gave me that made that little cut that turned her on so much… the “lover’s bite” as she called it. She had learned how to flick her wrist perfectly to get the desired result. I hated the pain of it, but I loved wearing her mark. By the time the last stroke was given, my tears were flowing freely, and my sobs echoed softly in the room.
When it was over, she pulled my panties up and over my red, welted and swollen ass. She dropped the cane and pulled me into her arms, comforting me, on the sofa, as she always did after discipline. She wiped my tears, cradled me against her chest, and kissed me deeply. She told me how much she loved me and how this was going to be a very special night. Despite my physical pain, the emotional connection between us felt stronger than ever. It was off the charts.
Incredibly, I could feel my penis trying to get hard inside the the tiny cage until it throbbed helplessly, unable to grow even a fraction under the restraints of the cage. It had been like this all evening, and I knew relief would only come after Anna had finished taking me… if then.
Finally, the moment arrived. “You’re still my virgin,” she whispered, “but not for long.”
Then we stood up, and she draped her arm around my waist, her hand on my sore ass cheeks. Incredibly, her touch was almost comforting.
As we entered the bedroom, it actually felt like she was the groom and I was the bride, guiding me to the bedroom door. My body trembled with a mixture of anticipation and nerves. She stopped and turned me to face her, her eyes locking with mine as she leaned in and kissed me passionately.
The throbbing ache in my disciplined ass was a sharp reminder of the journey that had brought us here. I melted into her embrace, utterly vulnerable yet completely safe. I had never felt this submissive, and in that moment, I knew with absolute certainty that I had never loved her more. I would have done anything to please her.
Anna pulled me closer, her voice a soothing balm. “It’s okay, baby,” she whispered, her breath warm against my ear. “I’m going to take good care of you. I love you.”
The bedroom was bathed in the soft glow of candlelight, the scent of the candles lingering in the air. Romantic music played softly, enveloping the room in warmth and intimacy. The silk sheets on the bed shimmered in the light, inviting and luxurious. It a place I rarely got to sleep. It was the bed we had once shared before the shift in our relationship, and seeing it now filled me with nostalgia. Tonight, I would share it with her again, but in a way I had never imagined.
“Get on the bed, on your back, baby… I want to see your face as I fuck you,” she said softly.
My limbs felt like jelly as I complied, positioning myself on the bed. I was trembling, not so much in fear, but from the overwhelming sense of surrender and trust. I wanted this now… I wanted to give myself to her completely.
I marveled at the beauty of her body… the soft breasts, the amazing hips, and that wonderful place that was always open and ready for my mouth. I could see that there was juice starting to drip from her. She was incredibly excited again.
Anna picked up the harness and strapped it on. She gently lifted my legs and pulled my panties off. Then she pushed my legs up. I wrapped my arms around my legs to keep them out of the way. I watched, and then felt her hands as she removed the plug… one of the three that had been a constant companion for the last two and a half weeks. I felt a momentary sense of emptiness, but it was fleeting as I lifted my head to watch her.
Then my breath hitched when I saw it wasn’t the five inch one she’d initially promised, but the seven-inch model. The shaft looked huge, the head even larger. She attached the artificial cock with practiced ease.
“That’s not the one we agreed on…” I stammered, my voice trembling.
Anna smiled, her eyes twinkling with mischief. “Hush,” she whispered, “No, it’s not. I decided to use the largest one instead. Don’t worry, I won’t go all the way in… at least not tonight. Besides, this one is only an inch or so larger than the plug you have been using.”
Her words sent a shiver down my spine, and I could only nod, my throat too dry to speak. It was almost two inches larger, but I didn’t say that.
She picked up the lube and squeezed some out. Her hands were warm and slick as she applied the lube, her touch firm yet soothing. She worked meticulously, ensuring I was thoroughly prepared before turning her attention to the strap-on. Watching her coat the artificial cock with the same care, I couldn’t help but think about her last lover and the size comparison she’d mentioned one time. I was going to get a cock the same size that he was, but just halfway inside me for now. My eyes fluttered shut as she moved closer, her body heat radiating against my warm thighs.
“Damn,” Anna murmured, her voice husky. “I love your red and well disciplined ass. It’s the cutest ass I’ve ever seen on a man. Red and striped like this… it’s beautiful. And it’s all mine… ‘Forever’.”
“Yes,” I whispered, my voice barely audible, unsure if she even heard me.
“Get ready,” she said gently. “Just the head first. Deep breath, baby.”
I felt the firm, rounded tip press against me, and I instinctively tightened before forcing myself to relax. I knew it wasn’t as large as the widest part of the plug I had been using, so the initial entry wasn’t as difficult as I had feared. Still, the sensation was overwhelming.
“There it is,” she said. “You have the biggest part of the head inside you. Take a deep breath and let it out slowly. Relax for me and let the head slip all the way inside.”
I obeyed, inhaling deeply and exhaling in measured breaths as the cock head penetrated me. Then the shaft began to slide inside, inch by inch. My body adjusted slowly, stretching to accommodate it. It wasn’t that different from the biggest plug… at least yet.
“You’ve taken about half,” Anna said, her voice filled with admiration. “How are you feeling?”
“Full… so full,” I managed between breaths. “But okay.”
“Good. You’re doing so well, baby. Let’s take some more.”
I gasped at her comment. She had said she would only give me half and already she was moving it deeper. I moaned as I felt the long shaft slowly going deeper into me. She continued to push forward, her movements slow and deliberate. Just when I thought I couldn’t take any more, she stopped.
“You’re amazing,” she said, her tone laced with pride. “You’ve almost taken all of it,” she said. “Just one or two inches more and you will have all of it. We need to do that. I want all of you.”
“All of it, I thought you said… uhh”, I grunted, now understanding what she was doing. She was testing me, she was challenging me. My head was spinning and I was trying to control my breathing. Only another inch or so, I thought.
Anna’s gaze locked onto mine, her expression filled with focus and tenderness. “Relax, baby, deep breaths. You’re doing so well,” she said softly, her voice carrying a mixture of encouragement and care.
My breathing was shallow, my body tense, but I followed her instructions, inhaling deeply and exhaling slowly.
“There we go. Just a little more,” she whispered, her voice steady and reassuring, but tinged with a growing excitement.
Time seemed to slow as I adjusted, my body working through the unfamiliar sensations. She was going to do it… she was going to give me all seven inches of it. My body tensed, my breathing shallow as she pressed deeper. I knew that there was only an inch left, but I had never taken anything so deeply. I moaned, I wasn’t sure I could manage it.
We both grunted as she flexed her hips.
“There you go,” Anna cooed, her voice warm and proud. “You did it. You have every inch. There is nothing left. I knew you could. Its so beautiful. Relax, let the feeling wash through you. I love so much, baby.”
Continue to Chapter 32
