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Friday, October 31, 2025

The Watchtower: Chapter 4

As mentioned in my story My Journey Into An FLR, here is a continuation which delves deeper into an episode that stands out in Jason and Anna’s shared history—a camping trip they embarked on to mark their anniversary. While some elements draw from truth, this narrative leans heavily into the fictional, offering a more vivid retelling of their adventure. During their stay in the wilderness, the couple encountered two women whose presence would, unbeknownst to them, enrich and solidify their relationship. The new friendships blossomed, influenced by a chemistry that neither couple could deny. Intimacy and adventure interwove, blurring the line between friendship and something more far more daring. Their time together explored the boundaries of trust, freedom, and love, setting the stage for nineteen immersive chapters that chronicle profound discoveries, and emotional revelations. If you haven’t read the Journey, I suggest you do before starting this new story. New to this story? Start with Chapter 1! Thank you for reading! – RG John


Chapter 4

Anna stepped forward, her eyes still gleaming with arousal. She guided me to turn and kneel before her. The look on her face told me everything… her fingers hadn’t been enough. I watched as she slowly slipped her shorts off, revealing her soaked pussy.

Without a word, she pulled my mouth into her swollen pussy. The scent of her, the heat, the raw openness overwhelmed my senses. As soon as my mouth met her, she came. Hard. Her climax surged into my mouth in waves, her juices flooding over my tongue, impossible to miss. I gasped, nearly choking, stunned by the sheer force of it.

It must have been her tenth orgasm of the day. At least.

When she was done, she eased me back and collapsed into one of the Adirondack chairs, her legs parted, her body glowing with release. Her face was soft, peaceful, eyes half-closed in perfect satisfaction. I remained kneeling before her, my head lowered, body aching, soul full.

Obedient. Disciplined. Fucked.

She owned me completely, without question. Mind, body, and soul.

And in surrendering everything to her, I had never felt more whole.

After a while, she helped me to my feet and gently pulled me across her lap. She held me close, her arms wrapping around my torso, and pressed tender kisses to my tear-streaked cheeks. Her voice, soft and warm, whispered words of love and praise that melted into my skin like balm.

Then she had me turn over on her lap. She reached for a towel and dabbed gently at the blood along my thighs and the tender ridges of my ass. Then came the cream… cool, soothing… spread over my welts with a care that made my chest ache. I flinched once, and she paused to kiss the one of the welts gently, reverently. It was her work and she loved it.

When she finished, she looked at me… truly looked at me… and then wiped the tears from my face. “I don’t know how I can love you more. You are a wonderful husband and lover… perfect.”

My heart swelled with pride and undying love. I felt safe, loved… no adored. All was right with the world.

We decided to spend the night in the tower. Still naked, I made my way down to gather our sleeping bags and enough food for a light breakfast. I also collected some leftover firewood that we could use for the stove.

As the sun dipped below the horizon, we sat outside wrapped in blankets, sharing a granola bar. The wooden Adirondack chair beneath me was unforgiving against my well-disciplined ass, making each shift a reminder of Anna’s earlier attentions.

Later, I heated up some hot chocolate, and we sat on the deck wrapped in our blankets again. We sipped our chocolate slowly, letting the warmth spread through us as the night came alive. Fireflies flickered in the darkness, their soft glow dancing among the trees, while the sounds of the forest created a quiet, rhythmic hum around us.

Above, the sky stretched endlessly, perfectly clear. From our high perch, we watched as countless stars twinkled, and every so often, the faint streak of a comet flared across the black expanse.

It was breathtaking… one of those rare, humbling moments where nature felt impossibly vast, yet intimately close. It wasn’t something you could see in the city… the lights were far too bright.

I glanced over at Anna and saw the serene expression on her face, bathed in the soft glow of the night. The moment felt perfect, and I knew exactly what I wanted to do.

Slowly, I slipped from my chair and onto my knees before her. She met my gaze with a knowing smile, then wordlessly pulled the blanket aside, revealing her lower half… her silent invitation. I didn’t hesitate. She was still naked. I eased myself between her legs. Then lifted her legs to my shoulders.

Her hands found my head, guiding me, and I let her, surrendering to the rhythm she set. I took my time, savoring every inch of her, trailing soft kisses along her inner thighs, my tongue tracing delicate patterns across her skin.

When I finally reached her center, I paused, captivated. In the faint starlight, her glistening pussy looked just as breathtaking as it did in daylight. My mouth watered as I lowered my lips to hers, pressing a slow, reverent kiss against her smooth, wet folds.

“Yes,” Anna hissed, her fingers tightening in my hair.

I took my time, teasing her, dragging out her pleasure, relishing the way her body responded to my touch. She grew even wetter beneath my tongue, her hips shifting, urging me on.

At last, I spread her lips open and let my tongue glide along her, slow and deliberate, from her entrance, slick with her arousal, all the way up to her swollen clit. Her body trembled, and when I pushed my tongue deep inside her, she screamed, her voice joining the symphony of the forest around us.

For a moment, I imagined a shooting star streaking across the vast night sky, marking the climax of her pleasure. Her legs wrapped around my neck, practically smothering me in her warm thighs and wet pussy. She climaxed multiple times before she finally collapsed back onto the chair. I would have gone on all night, but she gently pushed my head away.

When she had recovered from my oral pleasure, she looked down at me and said, “Stand up.”

I obeyed, still catching my breath, and was stunned when she reached up and unlocked my cage. The moment it came off, my cock sprang free, already dripping with arousal.

Anna’s lips curled into a knowing smile. “Look at that little thing. I swear it’s gotten even smaller in the last several months. Take it in your hand… let’s see just how tiny it is.”

Heat rushed to my face as I obeyed, wrapping my fingers around my shaft. It did look and feel smaller. There used to be maybe two inches above my fist, but now, barely an inch. My grip, from knuckle to knuckle, measured about three inches, which meant I was now barely over four… it appeared I had lost at least an inch. And it wasn’t just the length. Even in my hand, it felt thinner, weaker… almost pathetic.

Anna tilted her head, her amusement laced with something deeper. “I swear, you had more above your fist before.” Her smile widened. “I wouldn’t even feel you if I let you fuck me.”

A sharp, involuntary moan escaped my lips as my cock twitched in my hand. A slow pulse throbbed through me, and I felt warmth spread at the tip. I couldn’t believe her words, her dismissal, the stark reality of it, it was doing something to me.

I had heard of men who got off on being humiliated for their size, but that had never been me. And yet, here I was, struggling to understand the surge of arousal coursing through me.

Anna giggled when she noticed the glistening drop push its way free. “Oh? That excites you?” She studied me, curiosity flashing in her eyes. “Is it what I said… or is it the fact that you actually have a tiny penis now?”

I swallowed hard, but no answer came. I didn’t know the answer.

She tilted her head thoughtfully. “Maybe I don’t need to tease and deny you with my hand anymore. Pegging should take care of the necessary health maintenance. You certainly drooled enough when I pegged you to show that your prostate is getting the stimulation it needs. And honestly, it seems like you respond just as well, if not better, to direct prostate massage.” A slow smile spread across her lips. “Yes, I think I prefer that. At least as your primary form of stimulation.”

I moaned again, unable to prevent the tremors of excitement that were going through me at her words. I dared not move my hand.

I wasn’t sure how to absorb these feelings. I didn’t consider myself a wimp and never wanted humiliation, but now it seemed to be consuming. Still the thought of her never stroking me seemed like a major loss. I wondered if she would really do that.

I had always enjoyed our tease and denial sessions, the slow torment of her touch keeping me on edge. But at the same time… pegging had a different effect on me. Maybe even a stronger one.

She took out her phone and said, “Perform for me. I want to record it. I want you to be able to see how tiny you are and how pathetic that little thing really is. Then I will be able to compare how you react to a hand tease and denial and a pegging.”

I moaned again at her words.

Anna leaned in slightly, her voice soft but commanding. “I want you to tease and deny yourself while I watch.”

My eyes widened. “You… uh… you want me to…” I trailed off, unsure I had heard her correctly.

Her gaze was steady. “Yes, you heard me. Tease yourself. But do not come, or your ass will pay dearly.”

I swallowed hard. “Uh… okay.” My ass was already burning and I certainly didn’t want more.

Her expression turned playful, yet unmistakably firm. “If you slip up, you’ll have a very difficult time walking down this mountain.”

Understatement of the year. My nerves were electric as I hesitantly began to stroke myself. The sensation was almost foreign… after years of being denied, of only feeling Anna’s, and occasionally Sally’s touch, my own hand felt unfamiliar, inadequate. I couldn’t remember the last time I had actually wrapped my hand around it in a sexual manner. I ran my fingers along my length, which didn’t take much movement. Even that small movement sent a jolt of pleasure through me.

I worked myself up to the point that I was on the edge of climax and brought myself back. Although I knew how to do it and knew what was going on with my body, it was still difficult not to climax. Anna had remained seated and her still wet pussy was clearly on display, making it harder to not go over the edge. There was as steady stream of pre-cum juices drooling out of me.

My juices sparkled in the light from her phone. It was bright enough to wash out everything around us. All was coated in black except my hand, my little penis and balls. The thought of her showing this video to someone terrified and excited me beyond belief. I imagined the ladies at her club watching this on the big screen and I nearly climaxed.

To my detriment, she kept me going far longer than I ever would have on my own. She recorded it all, the minutes stretched endlessly, each wave of pleasure building, cresting, then receding, only for her to demand I push myself again. Despite my discipline, I began to doubt whether I could hold out as she kept making comments about how tiny I was and how I could never pleasure a woman with my tiny equipment. This was far harder than when she controlled my pleasure. I was drooling fluid in a steady stream now. When she finally allowed me to stop, I was exhausted and relieved.

With a quick flick of her wrist, her knuckles struck my balls just beneath their most sensitive spot. The sudden, sharp jolt of pain ripped a moan from my lips as I instinctively bent over, my breath catching in my chest. She giggled, clearly pleased with herself. She had never done that before. Until now, it had always been just a teasing flick of her finger—but this was different. This was sharper, crueler, far more painful.

Almost instantly, my penis began to retreat, shrinking away as if it understood exactly where it belonged. As if it feared her… because it did.

Anna’s eyes lit up at the sight. “That was much faster,” she observed with a sly smile. “You went soft almost immediately. I like that.”

A shiver ran through me, part fear, part awe. I felt a chill beneath my skin, not from the cool air, but from the realization that this trip had become more than just a getaway to enjoy the scenery. For Anna, it had turned into a journey of discovery… her discovery. She wasn’t just exploring the wilderness around us. She was exploring new ways to command and control me. And now, she had found something else, something devastatingly effective.

And she liked it.

Without hesitation, she locked me back up.

Anna stood up and looked down at my cage and said, “You know, we might have to get you a smaller cage.”

I didn’t think there was a smaller one.

Looking up at me, she met my gaze with quiet finality. “That was the last time you’ll ever touch your penis like that,” she said. Her voice was calm, certain. “Or maybe even have it done to you.”

A shiver ran through me, an unfamiliar mix of dread and unwanted excitement. I had known, deep down, that I was locked up for good. But this… this was different. Her words made it real in a way I hadn’t fully grasped before. My penis was no longer a source of pleasure, for either of us, and hadn’t been for a long, long time. Now, it had been reduced to its most basic function, stripped of any purpose beyond what nature required. Now, except for rare occasions, all pleasure would come from her pegging me, or me pleasuring her.

And that realization sent another shiver through me.

Back inside, Anna pulled out her phone again. Her fingers moved smoothly across the screen until she brought up the video of my pegging.

“Oh my,” she said. “This is amazing, look.”

 The moment it played, I gasped.

I hadn’t known what to expect, but the image on the screen felt surreal, almost unreal. The cock she wore looked impossibly large, stretching me open in a way that made me question if it could really be me. But there I was, bent over the railing, taking it fully, willingly, helplessly. Submitting.

My moans, thick with pleasure, filled the audio… unmistakably mine, yet distant, foreign, like I was watching someone else. The way my body responded, the way I opened for her without resistance… it was as beautiful as it was shocking. I had never seen myself like this. I had never imagined myself like this.

And yet, it was me.

When she finally pulled the cock out of me, I saw something I never had before. My hole didn’t immediately close. It lingered open, almost gaping, twitching slightly, used and raw. I wondered if it looked different. I couldn’t tell as this was the first time I was seeing it from her perspective.

Anna glanced at me, then back at the screen. “It’s definitely starting to look different,” she said, casually. “I can already tell. That’s what the doctor said would happen once your body got used to taking cock regularly.”

I turned to her, startled. “The doctor?”

She nodded. “Yeah. Remember? She said the anus is incredibly flexible—it can adapt to much larger sizes over time. Her husband takes nine inches now. Or maybe it was ten.” She shrugged, amused. “Either way, she was right. It is starting to look more like a pussy… my boi-pussy.”

She was correct, it was her boi-pussy now. She had claimed it for herself… well, Sally had some possession of it, but it was only at her command.

Then she swiped to a second video.

This one caught me off guard in an entirely different way.

It was the clip of me stroking myself. As the video played, my stomach knotted. Dread curled in my gut like smoke. I watched in stunned silence as my hand moved slowly, and realized just how little of my penis was visible with each stroke. The tip barely peeked from my grip

.

The truth settled over me with quiet finality: I had shrunk.

It wasn’t in my head. It wasn’t a trick of light or angle. It was real.

My penis was smaller now.

My balls, interestingly, looked the same. If anything, they appeared slightly larger—fuller. And after a moment’s reflection, that made sense. They were producing sperm daily, but with no release, it had nowhere to go. However, I had learned that my body absorbed it, nature doing its quiet work. But the buildup was visible now, more volume, more pressure.

I had experienced, like most men who are caged, “blueballs”, which was painful, but for me it didn’t last long. I took it as one of my many submissions to Anna. I took the pain for her and never complained.

A small, bitter laugh rose in my throat. Here I was… with a tiny penis and heavy, useless balls.

And yet somehow, I didn’t feel humiliated. Not anymore.

I had never been worthy of putting my penis inside Anna. It couldn’t satisfy her. Hell, it couldn’t even satisfy me anymore. All it brought was frustration—hers and mine.

And that truth sent another shiver through me.

But it wasn’t shame.

It was clarity.

I realized, in that moment, that I didn’t care. It didn’t matter anymore. Because I already had everything Anna needed from me. I had the body she used, the tongue she loved, the obedience she craved.

She didn’t need my penis.

And neither did I, other than to pee with.

That night, we curled up together in our double sleeping bag, our bodies pressed close, the quiet hum of the wilderness wrapping around us. But inside, my mind was restless. It had been a momentous day, for me and Anna. Although I had accepted that I had inferior equipment, there was still that shred of male pride that I couldn’t quite let go of. The emotions I had kept at bay finally broke through, and silent tears spilled onto the fabric of the sleeping bag.

I suddenly understood. This trip had a dual purpose for Anna. She had planned every moment, every test, every push. She was preparing me… guiding me toward something I hadn’t yet seen, something I hadn’t even known I was destined for. She had taken me apart, stripped me down to my rawest self, and in doing so, she was reshaping me into the man she wanted. The man she needed.

She had taken me deep into my submission, into the very core of my submission. The switching, the pegging and then the videos had taken me deeply into my subspace.

Anna knew better than I did that this was where I truly belonged.

I had thought, many times before, that I was hers. But was I really? Had I ever fully surrendered? Because it had taken this trip, this moment, to break through any lingering doubt. Now, I knew. I was hers, completely.


Continue to Chapter 5

Gary
rgjohn
I started writing erotic stories to bring excitement and pleasure to a world that could use more spice! Years ago, two of my steamy novels were published by a Canadian press, even making it to airport gift shops—how cool is that? While I loved seeing my books in print, I realized the real fun was in creating stories that spark connection and creativity online. Who knows? Maybe my stories are inspiring couples to explore FLR dynamics, with a cheeky wife making her husband read them as a playful twist (while caged, naturally—oops, did I say that?).

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