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.”…
