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 29: Anna and Jason Talk About Pegging, Testing Plugs, Teased And Denied With Plug In Place
A few days after the doctors visit, Anna and I were making love on the sofa when she brought up her recent doctor’s visit and how much she enjoyed us meeting with her. Anna was practically glowing as she talked about her. I was just as impressed, although for slightly different reasons. I liked her counseling of Anna, but not necessarily all of the suggestions. Admittedly a biased opinion.
“She’s amazing,” Anna said. “I loved how insightful she was about our lifestyle and her advice. I think we are on the right path.
I reached out to hold her hand. “I know you already know this, but I love the journey we’ve been on together. It’s incredible how much more we communicate, how much deeper our connection feels. I didn’t think it was possible, but I feel closer to you now than I ever have before. I don’t know if I could love you more.”
Anna’s eyes softened, and she leaned in to kiss me gently. “Thank you, Jason. I feel the same way. You’ve been amazing, and I’ve grown to appreciate you on a level I never imagined. But,” she paused, a playful glint in her eyes, “you know there’s still so much more to this than we’ve explored, as the doctor mentioned.”
I felt a slight twinge of nervousness at her tone… I knew what was coming. It was either pegging or cuckolding, and I don’t know which worried me more. “I know,” I said carefully. “What are you thinking about specifically?”
Anna’s smile turned into something both mischievous and knowing. “For example,” she said slowly, “pegging.”
“Pegging?” I repeated, trying to keep my voice steady, though I felt my cheeks flush.
Anna’s expression didn’t waver. “Yes, pegging. You heard the doctor mention it. She said many of her FLR wives require it, and they love it. It’s not just about pleasure; it has health benefits, too. I am sure you remember that she explained how it can help with your prostate health and can act like a tease and denial session. And with you being locked up permanently, and forever…” She trailed off and reached down, gently cupping my caged cock for emphasis. “We need to explore all the tools to keep you healthy, and keep things exciting.”
I swallowed hard, my heart racing as I tried to process her words. “So, you’re seriously considering it?”
“Not considering,” she said firmly, her tone leaving no room for doubt. “We’re going to try it.”
Anna leaned in close, her lips brushing against my ear. She whispered as if someone might hear, “I want this, Jason. Not just for you, but for us. This is about deepening our connection and exploring new territory together.”
I swallowed hard and said, “I’m a little scared. I mean, I’ve never … I mean, neither of us knows what to do.”
Anna smiled reassuringly and said, “Don’t be frightened. We’ll take it slowly. I’ve been thinking and reading a lot about this, and it’s perfectly safe if done right… even the doctor said that. I read that it really isn’t painful if you’re careful and take your time. What I want you to do is order an anal plug… maybe a couple of sizes… something you can wear for a while. We’ll start slowly, finding one that’s comfortable for you. At first, you can wear it for just a couple of hours, gradually working up to the point where you can wear it all day, or at least for hours, without a lot of discomfort.”
It spite of my fear, I felt my penis pulse inside its cage. Anna noticed immediately and smirked.
“Oh, look, your little guy likes the idea,” she teased, giving the cage a playful flick.
I wanted to say that it was simply an involuntary reaction, but it sounded lame. I stammered, “What are you going to use … I mean, the … you know, the strap-on dildo I got you is pretty big.”
Anna said with a glint in her eye, “The strap-on can hold various sizes, so you should order a couple of different sized attachments. We’ll work our way up slowly. I would suggest maybe a three inch one, a five, and a seven. Or in that neighborhood.”
I sucked in my breath at the suggestion of a seven inch dildo. That is what Anna already had. It looked huge to me.
Anna continued. “And make sure to get some high-quality lube… something specifically designed for this. We want it to be as smooth and comfortable as possible.”
“Uh … okay,” I muttered hesitantly. “But what if I don’t like this?”
She said, “Jason, we are in a FLR, and you, of course agreed to this, so I will take your concerns into consideration, but I make the final decision, and I want to do this. That said, many couples find that it’s not only pleasurable but also brings them closer.”
I learned that once Anna set her mind on something she was going to do it. “So, when are we going to do this?” I asked.
“As soon as you’re ready, but by two weeks or so, maximum. In fact, our anniversary is coming up in two and a half weeks, so that is our target,” Anna said, her voice steady but filled with excitement, “I’ll give you time to practice with the plugs.”
Then, she giggled and said rather proudly, “I’m going to claim your anal virginity from you. It will be like we just got married and you are a virgin. Just saying it out loud makes me tingle. The thought excites me so much.”
A wave of nervous excitement coursed through me. “Beyond the health benefits the doctor mentioned… why does this mean so much to you? What makes it feel so important?”
Anna paused, her gaze softening as she thought carefully about her response. “I’ve given this a lot of thought,” she began. “If I’m being completely honest, it is not all about power and domination. However, that is what FLR are about if we boil it all down. For most of my adult life, intimacy has followed a script… one where men naturally take the lead. He is on top. Even in the most loving moments, there’s this inherent dynamic where the woman gives and the man takes. And while there’s beauty in that, there’s also something I’ve always felt was missing. I want to experience the other side of that… and, just as important, I want you to experience the other side.”
She looked directly into my eyes, her expression earnest. “When I was younger, losing my virginity was, like for all females, significant. In the heat of the moment I had given my virginity. And I realized later that men rarely experience that in the same way. There’s pride for a man, maybe even a sense of accomplishment, but not the same vulnerability or surrender.”
I swallowed, feeling the weight of her words. “I… I think I understand. But it’s not like I took something the first time I was with a girl who was a virgin… it was mutual. It was something shared.”
Anna nodded. “Of course. But, from a woman’s perspective, it still felt like something was taken. And that’s not a bad thing… it’s just the way intimacy often works. What I’m saying is, I want to feel that significance, that deep connection, from the other side. I want to experience something from you that you can never give to anyone else. And more importantly, I actually want you to give it to me, freely and fully.”
Her words hung in the air, heavy with meaning. I could see the passion in her eyes, the excitement mixed with tenderness.
She reached out, placing her hand on mine. “I want you to feel what it’s like to fully surrender to me, to trust me with something so personal and intimate. And in doing so, I believe it’ll bring us even closer together. I want to celebrate our anniversary that way.”
I felt a lump in my throat as I nodded, her words sinking deep into my heart. She wasn’t just talking about physical intimacy… this was about trust, about giving ourselves completely to one another in a way we never had before and never can again. I was already her’s, but I had something else to give. Something I never thought I would give to anyone.
“I trust you,” I said softly.
Anna smiled, her expression radiant and filled with warmth. “That’s all I needed to hear.”
She leaned forward, her forehead resting gently against mine, and in that quiet moment, the depth of our connection felt more profound than ever before.
Then she continued. “As I said, we have two and a half weeks until our anniversary, so I will give you that time to practice with the plugs. Then, I want you to give me your anal virginity. It will be mine ‘forever’. Just saying that makes me tingle with excitement. I love the idea.”
I felt a tremor of excitement… and fear go through me. “I understand now.”
Anna’s eyes twinkled. “I have a plan for our anniversary. In fact, I am taking off a couple days. On the day of our anniversary, Saturday, we’ll go out for a romantic dinner. You’ll be caged, of course, the tiny one, and wearing a plug. Proper preparation is critical.”
“Oh,” I said, startled.
“You’ll also wear white panties, a white garter belt, and stockings under your suit,” she added. “We will go out to dinner at a really nice restaurant, with you wearing that under your clothes. And, as I said, you will put on the smallest cage you have so your little penis can’t get hard. On that night, you will have a pussy and not a penis. Your pussy will belong to me alone, ‘Forever’.”
I shivered noticeably and said, “Why do you want me to be like a woman?” She had never even suggested this, except for the panties.
“It’s pretty simple. I don’t want you to be a woman. I love you as a man, however, I want you, for one night, to feel like a woman. I want you to feel like you are giving me something precious like a woman would. I want you to feel totally submissive to me. In fact, I want you to paint your fingernails and toenails.”
I was shocked at that. “But… what about being at dinner… you know, with my fingernails painted?”
Anna looked at me sternly and said, “Be thankful that I am not making you wear a dress, makeup and a wig.” Then she laughed.
I shivered. She was right so I shut up.
She smiled and kissed me on the lips. Anna said, “I know this is our love making time, and not for sex, but your acceptance of this has made me so hot that I want you to use your mouth on me. I’m soaked.”
I smiled and dropped to my knees and pushed her legs apart. She was only wearing a robe so it was easy access to her. I could tell immediately that she was telling the truth… she was soaked.
I dove in and brought her to three climaxes before we went back to making love, meaning snuggling and whispering sweet nothings. My caged cock was still struggling to get out… and weeping.
After Anna left me to go to her bedroom, I sat on the sofa, replaying our conversation in my mind. Her words lingered, echoing in the quiet space around me. Slowly, as if a light had been switched on, realization struck me. It was so obvious. Why hadn’t I seen it before? I felt a flush of embarrassment wash over me. The answer had been right in front of me the whole time… right before my eyes.
Anna had been right, it was about trust, vulnerability, and giving myself to her completely. I had already given her control over my sexual release, my physical desires, including my sexual parts, and the very core of our intimacy. That was profound on its own, but this next step… the gift she was asking for… was even more significant. It was only mine to give. It was a natural progression of our FLR.
Driven by a surge of clarity, I stood up and went to find her. She was still in the bedroom when I knocked. Upon permission to enter, I stepped in and saw her scrolling through her tablet. She looked up when she saw me approach. Her expression softened immediately.
“I need to apologize to you,” I said, my voice steady but earnest.
Her brow furrowed slightly. “Why would you need to apologize, Jason?”
“Because I should have realized this on my own. I should have offered, not to be crude, my … my ass to you without you needing to ask. What you’re asking for… it’s something I can only give once, and I want you to have it. You pretty much have everything else already.”
Her face lit up with warmth and love as she set her tablet aside and stood to face me. “Jason, thank you. That means so much to me. All my FLR friends who’ve explored this say it brought them and their husbands closer than ever. I know it will do the same for us.”
I nodded, feeling the weight of her words and the sincerity in her eyes. “I’m not afraid anymore. I’m actually looking forward to it now. Because I love you, Anna. I love you so much.”
She smiled, tears glistening faintly in her eyes as she stepped closer and wrapped her arms around me. “I love you too, Jason. You are the love of my life, and nothing could ever replace you. What we have is something rare and beautiful, and I cherish it every day.”
We kissed then, a deep and tender kiss.
To Be Continued
