My Journey Into A Loving Female Led Relationship: Chapter 35

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 many chapters. If you are just starting, you should begin your journey back at chapter 1.

---

Chapter 35: Pleasuring Anna, Tease and Denial, Jason Helps Anna Get Ready For Her Date

I was still reeling from Anna revealing that she was taking a lover when she had me get up from eating her. Then to my surprise, she allowed me to sit on the cushioned seat rather than the hard surface. I looked at her questioningly, but she only smiled, a mischievous glint in her eyes. Without a word, she straddled me, her thighs on mine, my caged penis between us. She leaned in and kissed me deeply.

The kiss was intoxicating… soft and passionate, yet commanding. I melted into it, surrendering to the heat between us. Then, without breaking eye contact, Anna reached down and unclasped the delicate chain around her neck, retrieving the small, gleaming key.

I held my breath as she used it to unlock my cage. The moment the latch clicked open, my cock sprang free, betraying my complete and utter lack of restraint.

My heart pounded in my chest. Was she really going to let me inside her? That was almost too good to be true… was she feeling guilty and wanted let me feel her pussy for one last time before she was stretched by a much bigger cock? Or, maybe… maybe she was at least going to tease me. I prayed that she wouldn’t just stroke me a couple of times and put me away. I wanted… needed more, even if there was no release at all.

Anna’s lips curved into a knowing smile as she took in the sight of my dripping, throbbing erection. “Me thinks you protest too much. You like the idea of your wife having a superior lover, don’t you?”

She wasn’t wrong, and we both knew it.

Without another word, she slid her fingers into her pussy, gathering the copious juices from inside before wrapping her hand around me… firm, yet gentle. A sharp gasp escaped my lips as she began to stroke me, her touch agonizingly slow, her own juices serving as the perfect lubricant. I don’t think she had ever done this before… using her own excitement to tease me. This was beyond anything I could have hoped for. But at the same time, a creeping anxiety settled over me. Would I last? Would I disappoint her?

Her fingers dipped between her legs again, coating themselves before returning to me. She was soaked. I wasn’t sure if it was from me eating her, the teasing, the thrill of control, or the thought of Michael. Probably all four.

Then she pulled off her top, revealing her full, perfect breasts.

My breath hitched. I squeezed my eyes shut, willing myself to focus. If I lost control, I’d ruin the moment… and my ass would pay for it.

Anna chuckled softly, her voice low and teasing. “Dangerous, hmm?” Her stern gaze locked onto mine. “You know the rules. I’ll allow you to have a ruined orgasm… but only if you’re good.”

A shiver ran through me. As all of us caged subs know, ruined orgasms aren’t entirely pleasurable, but they were still something I cherished—proof of her control, her power over me. It had been so long since she had even allowed me to droolnow that she was pegging meon a regular basis.

I nodded, biting my lip, forcing myself to stay steady. But I also knew how skilled Anna was at pushing me right to the breaking point.

“It’s going to be fun with Michael,” she purred. “You’ll see. And you’ll have a very satisfied, happy wife. I know want that.”

“Yes,” I admitted, my voice shaky as my eyes darted between her gorgeous breasts and the beautiful hand wrapped around me, stroking me with infuriating precision.

She was driving me insane. But I would not disappoint her. “Hold,” Imoaned.

She paused and her smile turning wicked. “I know he’ll be a great lover. His cock is incredible… fully seven inches plus and so thick.” She paused, letting her words hang in the air before adding with a glint of mischief, “And you know what?” She started stroking me again.

I swallowed hard, feeling the tension in my body rise. “What?” I croaked. “Hold.”

“His cum tastes amazing,” she said, her voice dripping with satisfaction.

I moaned loudly, clearly on the edge.

Anna paused her stroking and continued speaking. “I don’t know what he eats, but it’s the best I’ve ever tasted. And to top it off…” she leaned closer, her lips brushing my ear, “…he cums sooo much. It literally fills my mouth to overflow.”

Another groan escaped my lips as I fought to control myself. She resumed stroking me, her rhythm slow and deliberate. My body trembled as she leaned in further, her breath warm against my neck.

“I know he’s going to feel so good inside me too,” she whispered, her tone both sultry and playful. “I’ll cum a million times on him.”

“Hold,” I gasped, barely able to speak as the pressure built.

Anna giggled, a wicked glint in her eyes, pausing just long enough for me to catch my breath before resuming, her strokes skillful and relentless. She played with me mercilessly, drawing out the torment, stopping and starting, pushing me to the very brink over and over again. I lost count of how many times I gasped out the “hold” word, my body trembling with desperate need. This was the longest teasing session we had ever had. She was testing me like never before.

Then, with one final, expertly timed stroke, the inevitable happened… a ruined orgasm spilling from me in slow, unsatisfying drools, the pleasure muted, incomplete. Anna’s hand left me the moment it began, denying me even the illusion of release. My poor little guy twitched uselessly in frustration, throbbing as if pleading for something more, for one more stroke… but there was nothing left for him. As always, I was left aching, frustrated, and utterly at her mercy.

Anna laughed softly, raising her hand to her mouth to taste me. Her tongue flicked out, and she smirked. “Yours is all watery… his tastes so much better better,” she teased.

I slumped back in the chair, utterly spent… yet my penis still throbbed. As Anna rose gracefully, I couldn’t tear my eyes away from her swaying hips and the perfect curve of her ass as she walked away with an effortless confidence, glancing back over her shoulder with a triumphant smile, knowing I would be watching. She returned a moment later with ice and pressed it to my still throbbing penis until it relented and finally went down… then the cage was on me again.

She smiled and said, “Did you enjoy that?”

As frustrating as it was, I answered honestly. “Yes, very much.” I hadn’t lost one little bit of desire for her. The sight of her sent waves of electricity through me. She had me… completely, irrevocably… I would do anything for this woman… deny her nothing. And we both knew it.

Then Anna paused and told me she had scheduled her first date with Michael—tonight. I gasped, the weight of it hitting me all at once. There was no time to process, no chance to sulk or spiral into overthinking. And maybe that was her plan all along. She knew exactly what she was doing, making sure I was in the right frame of mind for this momentous step. She wanted me caught between anticipation and helpless desire, and she succeeded. I was already crazed with longing and excitement.

For the next few hours, I couldn’t shake the thought of Anna taking a lover. It wasn’t a complete shock as I figured it was going to happen sometime. But knowing it was happening tonight sent my mind spiraling. This was the most momentous shift in our relationship, something I had thought about yet never truly prepared for. The reality of it was almost overwhelming, bordering on terror. And yet, every time I thought about it, my body betrayed me… my caged penis throbbed, dripped, and ached with anticipation. I tried everything to distract myself, but it was useless.

Waves of worry and insecurity crashed over me. I knew Anna had reassured me that this wouldn’t change us, but how could it not? She was going to kiss, touch, and fuck another man. A man who, by every measure, was more than me. He was tall, handsome, charismatic, well-built. And while I considered myself above average in most of those areas… except charisma, due to my shyness, none of that mattered now. He was the one who would be inside her tonight, the one she was going to suck, and maybe swallow his cum… never me.

I had no access to her anymore, unlike other cuckold relationships where the husband and wife still had penetrative sex. But maybe that was for the best. After all, Anna had made it clear… she was taking a lover because I was simply inadequate for her needs… too small, and unable to hold back my climax until she was satisfied. And after being caged for so long, I was even smaller than when this all began.

Of course, I had subtly agreed to this when I submitted to our FLR, but I had always managed to push the reality of it to the back of my mind. Now, I couldn’t ignore it. If Anna had given me more time… maybe a couple of weeks, or even just a few days, I might have been able to process it better. But now, it was here, and it was happening tonight. My head spun, my stomach churned, and I couldn’t even eat dinner.

Anna knew what I was going through. She could see it all over me, and she tried to reassure me, promising that everything would be fine. Deep down, I believed her. But that didn’t make it any easier.

In preparation for Anna’s lover’s arrival I assisted Anna in her bath, meticulously shaving her pussy and legs, ensuring not a single inch was missed. She had me remove the cage because she wanted to see my little boner hard… she wanted to see the proof that I was excited, accepting of this. She got her wish… I stayed hard and dripping the entire time… if I started to shrink for even a moment, all I would have to do is think about what she would be doing in just a couple of hours.

Then Anna asked me to dress her for her night with Michael. Picking out clothes for her was not something I ordinarily did. Oddly, it felt comforting, in a way. It meant I was part of this, not excluded from the moment. It was also her way of letting me participate and for me to show my acceptance of her taking a lover… a step I had subtly agreed to long before this night.

I approached the task with reverence, understanding the significance of every detail. I selected a delicate frilly white blouse that hinted at the lace of her bra beneath, paired with a short, form-fitting black skirt that hugged her flawless thighs. She couldn’t go braless as they were going to be out in public having dinner first.

For lingerie, I chose a pair of bikini-cut panties that never failed to take my breath away. They covered the V in front with material, but left her backside almost completely exposed… an image permanently burned into my mind from all the times she wore them around the house. To complement them, I selected a pair of sheer thigh-high nylons, the kind with an elastic band at the top to keep them in place. She despised pantyhose… joking that wearing the thigh-high nylons would serve as an invitation for Michael to slip his hand between her legs if he dared. The mere thought sent a shudder through me, my uncaged cock twitching helplessly.

As the final touch, I chose a pair of six-inch heels—shoes she rarely wore but that made her legs look absolutely breathtaking. The moment I imagined her in the full ensemble, poised and ready for another man, my body reacted with an intensity I could barely contain.

When she stepped into the outfit and turned to face me, my breath caught. She was stunning… confident, radiant, and glowing with anticipation. In that moment, she was everything I adored and more.

“You look… breathtaking, Anna,” I managed, my voice a little unsteady. My hard little penis, which she still left uncaged, throbbed. I realized that this had been the longest time I had been without the cage since I gave her the keys.

Her smile softened as she replied, “Thank you, Jason. I know this isn’t easy for you, but I want you to know how much I appreciate you.”

I nodded, unsure if I could speak without my voice betraying the complexity of emotions swirling inside me.

As she gathered her things, the weight of the moment settled over me. The truth hit me in waves. My wife, my Anna, wasn’t just going out on a “date.” Tonight she would be taking a lover… pure and simple. The dinner was just a preliminary… something to turn them both on. I was certain that both would be crazed with desire by the time they headed for the room.

Before she left, Anna asked if I wanted to know the details. At first, I hesitated, unsure of how much I could handle. But as I thought it through, I realized I would rather know than let my imagination fill in the blanks. So, I told her yes.

I was surprised when she started telling me the details right away. “We’ll start with drinks, and then dinner,” she’d said, her eyes alight with excitement. “We will have to be careful since we will be in public, but I am sure I will get to feel his erect cock under the table, and I am planning on slipping off my panties while we sit there… and then hand them to him as my acceptance of what we are about to do. After dinner, Michael has arranged for us to go to a five star hotel, with a suite instead of just a bedroom.”

A thought occurred to me and I more or less blurted out, “Are you going … uh … going to … use you know, protection.”

Anna laughed and said, “No, you know I’m on the pill, and  I hate condoms. Besides, Michael is perfectly safe. He promised me that he had never been with another woman since he and his wife met… and I believe him. Not only that, I want to feel, to put it bluntly, him cum in me… its been far too long. I’ve always love that feeling, even when you used to do it. It is confirmation, and an affirmation, for me that I have done my job, and pleased my man. It always makes my climaxes more intense.”

I wondered for a moment if she was going to require him to clean her afterward. In truth, I knew she wouldn’t. This wasn’t a date with a guy she was going to marry, they were going to fuck. And I suspected that if she did give him a blowjob, she would swallow, as she had done previously. I remembered, with a shiver of excitement, that she said she liked the taste.

“Okay,” I said, unsure how to respond to that.

“In the future, I think we will meet once a week on Friday nights, as Michael has a poker group, which he will be resigning from. However, he feels like the idea of his wife thinking he is playing poker makes everything a little more palatable for the two of them. I think it is more for him than his wife.” 

Anna said softly, “I need this so much, Jason. I’ve forgotten how it feels to have something real inside me instead of something artificial. I want to feel a real cock throbbing inside me… the head growing before he blasts his amazing cum inside me. I want to experience that feeling again, savor every moment of it.” She paused, her lips curling into a playful smile. “And I want it to last longer than thirty seconds.”

Her words stung, but I couldn’t deny the truth in them. Real was always better than artificial. Yet, despite my logical understanding, the image of my wife in another man’s arms hit me hard. My chest tightened, my head spun slightly, and the weight of the moment felt almost unbearable.

Anna immediately noticed the change in my expression. Her playful demeanor softened, and she pulled me into her arms. “I’m sorry, Jason. That was insensitive of me.”

I shook my head as I pulled back slightly. “No, it’s not that. It’s just… an image popped into my head, and I wasn’t ready for it.”

Anna studied my face carefully before her eyes flicked downward. With a knowing glance, she reached down and gently grasped my throbbing penis. Her eyes widened in surprise before a sly smile crept across her lips. She could feel that I was literally dripping as my precum coated her palm.

“You have been excited by this all evening,” she said softly and squeezed my penis. “This tells the story… and I love the story.”

My face burned with embarrassment my penis pulsed in excitement and more juices dribbled out… I was excited as I had ever been. My gaze shifted away from her… fearing that just looking at my beautiful wife, all dressed up for her lover would make me climax. Desperate to change the subject, I stammered, “What time do you think… uh… you’ll be home?”

Anna leaned back slightly, still smiling. “I’m not sure. It depends on how many times Michael can climax.”

I gasped at her words and she giggled. “Don’t expect me back until late… probably around two-ish or so. You should go to bed.”

To Be Continued