My Journey Into A Loving Female Led Relationship: Chapter 15

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.

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Chapter 15: Jason Finds Proper Chastity Cage, Jason Provokes Anna Into More Discipline

We got through the week without me provoking Anna into a spanking, although I still had demerits I had yet to cash in. It was Friday, so my ass had healed well enough that she could discipline me without fear of causing more harm than was necessary. I sat at the breakfast table as usual. It was our time to align schedules and discuss our agendas to avoid working at cross purposes for the following week.

Anna was focused on her calendar, flipping through appointments and jotting down notes. As I watched her, I couldn’t help but notice how her work attire had subtly shifted. I’d already noticed how she dressed more provocatively at home, but now it seemed she was bringing that same energy to the office.

She wore one of her typical tailored suits, but the pants seemed tighter, hugging her hips and thighs in a way that made it impossible not to notice. I wondered if she had taken her clothes to a tailor. She had her suit jacket over the back of the chair and was wearing a white blouse. Her blouse, normally buttoned high to her neck, had three buttons casually undone. It wasn’t overtly revealing, but if she leaned forward at just the right angle, someone might catch a glimpse of the soft slopes of her breasts.

And then it hit me… she wasn’t wearing a bra.

Anna had never gone to the office without a bra before, at least not that I knew of. It was a subtle but powerful choice, one that sent my mind racing. Was she trying to impress her bosses? Or… was it for someone else?

I pushed the second thought away almost immediately. I didn’t want to entertain that possibility, but the unease lingered in the back of my mind.

Anna glanced up from her calendar and caught me staring. She smirked slightly, as if she knew exactly what I was thinking, and then turned her attention back to her notes without saying a word.

Whatever her reasons, one thing was clear: Anna was changing. And I was still trying to catch up.

“Okay, let’s see… I have a business dinner next Wednesday night, so I’ll be home late. I’m also having lunch with Sally on Thursday,” she said.

“So, no dinner at home Wednesday?” I clarified.

“Correct. Oh, and I want you to install a program on my computer this weekend that mirrors everything you look at on your computer and phone.”

“Okay, I can do that,” I said, though the thought made me nervous.

“Now, about your job,” she said, her tone turning serious.

“You know you’ll have to be punished for losing it… and severely. That was inexcusable, especially how you lost it. I can’t believe how irresponsible that was. Losing your job like that could very much cost you other employment opportunities.”

It had been a couple weeks since our initial discussion and she had not brought up the job loss issue. I was hoping she was going to let it go, but deep inside, I knew better.

“I know. You don’t know how sorry I am, for all of it,” I admitted.

Then Anna shocked me to the core, when she said, “The truth is, I don’t care if you have a job. In fact, I don’t want you working outside the house either. I have too many things for you to do here. You’ll take on some of the tasks I hate with my job, like registering and filing documents. It’s simple, but you’ll need to learn the process. You can do it right here from my computer. Of course this is all in addition to your other duties.”

I was stunned. All I heard was that she didn’t want me to have a job?

“It’ll be like a job,” she continued, “but I’ll pay you an allowance based on how much work you complete. It won’t be much, just enough for your comic book hobby and the occasional round of golf with your friends. Oh, and I want my name on your checking and savings accounts.”

Her words hit me like a ton of bricks. If there was ever a definition of being a “kept man,” this was it. I realized how completely dependent I would become on her, both financially and emotionally. It was a life entirely dictated by her terms. Then again, wasn’t that exactly what an FLR was all about?

“Yes, ma’am,” I said finally, knowing there was no other acceptable response.

The rest of the day while Anna was at work followed a predictable routine.

Instead of ordering a temporary bed, I select a nice twin bed, which was delivered the following day. I also picked out a night table and lamps. The setup made me happy but also nervous, it felt like she might be planning for this arrangement to be permanent.

I cleaned and organized the room, making it as comfortable as possible.

The chastity cages I had ordered arrived a couple of days earlier, and I tried on several of them. Some were manageable during the day, but wearing them at night was a different story. I struggled to last through the night, waking up repeatedly as my penis tried to get hard. I wasn’t even having sexual dreams… it seemed the cage itself caused the stimulation.

Through trial and error, I found that smaller cages were more comfortable. Eventually, I settled on one less than three inches long. As long as I remained soft, it was tolerable, and I managed to wear it throughout the day. But nighttime was another challenge entirely, and my sleep suffered. But I persevered and got used to it.

I took the cages off when Anna was home and I hadn’t mentioned them for two reasons. First, I wanted to ensure I could handle them before introducing her to a particular cage. Second, Anna had been extremely busy with work that week and didn’t need another decision to make. She was juggling multiple court cases and seemed stressed and flustered.

To help her unwind, I gave her baths, massages, and pleasured her whenever she allowed me to, which was often. We set up regular massages for Wednesday nights. Shaving her pussy and legs whenever she needed it, and her first pedicure was scheduled for three weeks, once I learned how to do it.

While these efforts seemed to ease her stress temporarily, it wasn’t enough to lift her mood entirely. She hadn’t even initiated my “maintenance,” which worried me. I was wearing the cage so the temptation to jerk off was greatly reduced.

Unfortunately, all my pampering didn’t see to help reduce Anna’s stress. I knew I needed to do something to cheer her up. I only knew one sure fire way at this point, but it was dangerous for me. She hadn’t disciplined me in a while, which was also unusual.

My backside had mostly healed, though faint bruises still lingered as a reminder of my last punishment… with the hairbrush again. We hadn’t started using the new discipline tools and Anna hadn’t even mentioned discipline all week, and I was hesitant to bring it up. But I remembered how much it excited her, and how much I craved that connection with her. It was probably a mistake, as I would soon find out. I had recorded twenty-six demerits which had not been cashed in.

It was a Thursday evening and Anna had decided to work at home tomorrow, so she could get some needed legal work done without the distractions of the busy office. That evening, Anna was in her office, deeply engrossed in her work. I entered, naked and with a cage on, hoping she would notice and maybe stimulate a conversation. “Do you need anything?” I asked.

She didn’t even glance up. “No, I’m busy.”

Undeterred, I offered more suggestions: a massage, cooking a special meal, use of my mouth. I wasn’t deliberately trying to get under her skin, but I wanted a reaction, even if it was bit of anger.

Finally, she got the message, dropping the papers she was reading and looked at me. “What are you doing? Can’t you see I’m busy?” she said, her tone sharp, if not angry.

I said, “I know you’re busy. But you’ve distracted all week. l  feel like I am invisible to you,” I said boldly.

Her eyes narrowed dangerously. I could see her anger growing. “You see all this work on my desk? I’ve got two cases pending and they gave me another. I don’t have time to even think.”

“I know, but what about me… you don’t have any time for me,” I said, knowing I was pushing too far but unable to stop myself. This was a bit insane.

In a flash, she stood, tossing her documents aside, and seemed furious.

“Don’t you ever talk to me like that again,” she said, her voice icy. “Do you understand that if I lose these cases, I could lose my job? Do you have any idea what that even means for us?”

I immediately regretted what I had done. I had no idea the kind of pressure she was under. I started to say I was sorry, but it was far too late to apologize. I had really fucked up.

“Go get the discipline tools we ordered.”

My stomach dropped. Frankly, I hadn’t expected this much anger. I realized that I had over-stepped my boundaries. I shut my mouth and hurried to the bedroom to retrieve the packages. I opened the two package and found a variety of implements: paddles, canes, and even a leather cat-o’-nine-tails. The second box contained restraints and a mouth gag… items we hadn’t explicitly discussed.

Carrying both packages back to her office, I felt a growing sense of dread. Anna dumped the contents onto the floor, and I stared at the collection of intimidating tools. There were at least ten punishment items, ranging from small paddles to flexible canes. 

“Pick one,” she ordered, her tone cold. “Choose what I’m going to beat you with.” She stood there with her arms crossed, staring at me. Even though she didn’t have a lot of time for me, she still wore skimpy clothes… today it was a small pair of dental floss bikini panties that didn’t cover an inch of her ass, and a tank top that was low cut to see most of the insides of her breasts. Her nipples were positively huge… maybe from anger or excitement. I wasn’t sure.

I froze, my heart racing when I realized she used the word “beat” and not spank. The word sent a shiver down my spine. She had never sounded like this before, and it unnerved me. But I reminded myself that this situation was of my own making. I had asked for this dynamic, and now I had to face the consequences.

Swallowing hard, I had no idea what to select. I picked up the paddle, but Anna immediately said, “No, I’ve decided to use the cane.”

I drew in my breath. I was pretty sure that was the worst of the various items she could chose. It was about three feet long and flexible. I knew it would hurt and leave marks, if not cut skin. I handed it to her with trembling hands.

Anna swished the cane through the air experimentally, the sound sharp and terrifying. I flinched at the noise alone.

“How many?” I asked, my voice barely above a whisper.

“It’s none of your business. I’ll stop when I’m tired of beating you,” she said coldly.

“Should I take the cage off?” I asked. I had been wearing it most of the morning… although when we were together at the breakfast table I had my apron on, and she hadn’t seen much of me until now.

“I didn’t know that you were even wearing one,” she said in surprise.

I started to make a remark about how that was evidence since she had been ignoring me. I decided to keep my mouth shut.

“No, leave it on. Wouldn’t want you to get hard during your punishment,” she said and chuckled without humor.

I was second-guessing everything. Anna had never used these tools before, and she was clearly furious. Worse, we hadn’t established a safe word. But it was too late now.

“How many demerits have you earned this week?” she asked, her tone sharp.

“Twenty-three,” I said quietly.

“Then you’ll get at least that many strokes,” she replied.

Twenty three strokes. At a minimum. With a cane. I had no idea how I’d endure it.

She took me to the living room, and had me lie over the ottoman, now the place of choice for our discipline sessions. I found myself wondering if I should get something made for discipline.

When I was in position I looked up at Anna with what I thought was a pleading look. I saw no reprieve. This had been coming for a long time… ever since I had revealed that I had lost my job. It was correction time.

The first strike landed with a sharp crack. I jumped and suppressed a scream. It was like a bolt of lightning hitting my flesh. Before I could process the pain, the second and third strikes followed in quick succession.

The spatula and hairbrush she’d used before had hurt, but this was on a whole different level.

She seemed to prefer groups of three, pausing just long enough for me to anticipate the next set. By the twelfth stroke, tears were streamed down my face.

Anna paused briefly, catching her breath. I glanced back to see her eyes still burning with intensity.

Then it began again. By the time she reached twenty, my entire backside was ablaze. I couldn’t distinguish the individual strikes anymore… everything blurred into one overwhelming sensation of pain.

“I need something to drink,” she said, stepping away.

When she came back, I felt her fingers tracing over the raised welts on my skin. “There are some tender areas here… and here,” she murmured and poked them with the end of the cane, bringing a cry of pain from me.

Tears continued to flow freely down my face as I lay there, totally exposed. There was no protection… no reprieve.

She walked around to the back of me. Suddenly I felt a sharp pain in my ball sack.

Then Anna stepped around the front of the ottoman and leaned down to my face. She said, “See how sensitive that area is? Think how bad it would feel if I used this cane on those little orbs.”

Of course I didn’t answer.

“You’re completely responsible for this,” she said, her tone low but firm. “I don’t know what you were thinking, messing with me like that. I’ve got enough on my plate without you confronting me, too.”

I wanted to say I was sorry, to beg for forgiveness, but nothing would come out. Instead, I let my tears speak for me. I truly regretted provoking her. I knew she wasn’t going to relent.

Anna went around to the back again and I waited for the. She hit me five or six more times and I heard her say, “That’s enough.”

I was relieved to say the least.

Continue to Chapter 16