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 30: Jason’s Preparation For Pegging, Out to To Dinner
The following day, I ordered everything we needed. I paid for overnight shipping, and the package arrived promptly the next afternoon.
Inside, I found three sizes of metal butt plugs, each adorned with a colorful crystal at the base, three incredibly lifelike strap-on dildos… artificial cocks really… and a large jar of premium lubrication. As I examined the contents, my little guy stirred against the confines of the cage, reacting involuntarily to the possibilities ahead.
Curious, I decided to try out the smallest plug. In the bathroom, I cleaned myself thoroughly before carefully pressing it inside. It slid in smoothly, though I worried briefly about whether it would stay in place. After a moment of adjustment, I realized it felt secure enough.
Determined to test its presence, I resolved to keep it in until Anna returned home… several hours away.
Those hours were a challenge. The plug was an unrelenting reminder of what was to come, a constant awareness nestled inside me. I found myself glancing at the clock more often than I should have, time dragging in excruciating slowness. When Anna finally walked through the door, I had made it. Relief mixed with anticipation as I abandoned dinner preparations, poured her a glass of wine, and met her as she settled onto the sofa. As always, I knelt at her feet.
“Hard day?” I asked, noting the exhaustion in her eyes.
“Yes,” she sighed. “Just a bunch of legal bull. But now I’m home.” She studied me for a moment, then added, “Would you massage my feet?”
I silently chastised myself for not offering first.
“Of course,” I said eagerly. “Actually… if you’d like, I could make it a habit—bringing your wine and massaging your feet every day when you get home.”
Her lips curved into a soft smile. “That’s so sweet. I’d love that.”
I slipped off her heels and began kneading her soles. The low groans of pleasure told me I was doing a good job, and I took my time, working out the tension from her long day. I even kissed the tops of her feet several times, bringing a sigh from her. I looked at her toenails and they sill looked good, so a pedicure was not needed.
Once she seemed more at ease, I said, “The plugs arrived today.”
“Already?” she asked, arching a brow.
“I paid extra for priority shipping,” I admitted with a grin.
Her eyes sparkled with curiosity. “Eager, were you?”
I blushed but said nothing.
“I want to see them,” she said.
I rose and returned with two packages, opening the one containing the strap-ons first.
Anna picked up the smallest one, a modest three inches, turning it over in her hand. “They look incredibly lifelike,” she murmured, then smirked. “This one is very much like yours.”
My face burned—I knew I was bigger, but not by much.
“But this one might be too small,” she mused before setting it aside.
She reached for the medium-sized one, about five inches long, and gave me a teasing glance. “This one’s a bit bigger than your little guy.”
I blushed again, her playful smile sending a familiar heat through me.
I watched as Anna tested the flexibility of the medium strap-on, bending it and watching it spring back into shape.
“Should be firm enough, I think,” she mused.
Then she lifted the largest one… a solid seven inches… and smiled. “This should do. It’s about the size of the one you use on me. I look forward to using it on you.”
“Uh… as you said, let’s take it one step at a time,” I suggested carefully, hoping to delay any grand plans.
“Of course,” she said, her knowing smile making me uneasy. “But we should challenge ourselves. And you will get there, for sure.”
I bit back the urge to say that even the smallest one would be a challenge. Instead, I watched as she moved on to the second box, picking up the largest plug, which was about six inches long… turning it over in her hand.
“Oh, isn’t this cute?” she remarked, admiring the crystal at its base. “It’s like a little jewel. Is this so you know which side goes in?” she teased.
“I think we can figure that part out,” I replied, matching her humor as best I could.
She picked up the medium plug, about five inches, and studied it. “This one looks more like your little guy… maybe a little bigger.”
She’d already said that about the strap-ons, but I didn’t bother correcting her.
Then she frowned slightly, glancing back into the box. “Wait… where’s the smallest the last one?”
I couldn’t help but grin. Standing up, I turned around and bent slightly at the waist, revealing the plug already snug in place.
Anna’s hand flew to her mouth before she burst into laughter. “Oh my God! That’s adorable,” she giggled. “I love it. The purple/red color looks perfect with the punishment stripes from yesterday.” Her amusement lingered as she finally asked, “How long have you had it in?”
“About two hours,” I admitted. “And if you don’t mind, I’d like to take it out now.”
“Hmm,” she said thoughtfully. “Let’s wait until after dinner. I want to tease and deny you while it’s still in, so you can tell me how it feels.”
I swallowed hard, suppressing a groan. I had a feeling she’d say that. It had probably been a mistake to wear it… but I had wanted to surprise her.
“First, you can finish my foot massage,” she added, extending her leg toward me.
I groaned inwardly, knowing she was testing me again. I had walked right into her trap. Still, I obediently resumed the massage, my fingers kneading her soft soles, my own predicament growing more intense with each passing moment.
When I finished I stood up. “Let me get you another glass of wine and finish preparing dinner,” I offered, trying to mask my impatience.
She giggled knowingly. “Go ahead,” she said, reclining into the sofa. “Take your time.”
Her playful laughter followed me back into the kitchen, where I resumed cooking, my thoughts racing with the night still ahead.
When dinner was ready, I called Anna to the table. A fresh glass of wine was waiting for her as she sat down. I placed her plate in front of her, then hesitated before taking my own seat. Anna noticed immediately.
“First time sitting down with it in?” she asked, feigning innocence.
“Uh… yeah. I’ve been on my feet for over two hours. I was hoping to take it out before dinner,” I admitted.
“Well, that’s not going to happen.” She lifted her fork to her lips, her eyes twinkling with mischief. “Sit.”
I started to lower myself but paused when Anna added, “Oh, and take off the apron. You know the rule—no apron at the dinner table.”
I sighed, realizing I’d forgotten. Slipping it off, I felt my skin flush as Anna’s gaze immediately dropped to my caged penis.
“Me thinks you protest too much,” she teased, smirking as she noted the obvious swelling behind the bars.
I shifted uncomfortably. “I think it’s massaging my prostate and that… well, you can see the result.”
She chuckled as I braced myself and carefully lowered onto the chair. The combined sting of the cane marks and the pressure of the plug made me wince, my body instinctively tensing. A groan escaped my lips as I almost jumped back up, but with a deep breath, I forced myself to settle, feeling the plug press even deeper inside me.
Anna watched with delight.
“Eat,” she instructed, her grin widening as she took another sip of wine.
Throughout dinner, Anna repeatedly asked how I was doing, her amusement evident. Each time, I replied with a tight-lipped “I’m fine,” though the challenge of sitting with the plug made focusing on my food nearly impossible.
By the time the meal ended, I had somewhat adjusted to the sensation. It didn’t hurt exactly… I just felt overwhelmingly full. I could only imagine what the largest plug would feel like.
After clearing the dishes, I returned to the table, where Anna was engrossed in a legal brief.
“Are we ready?” I asked, eager to move on to the teasing session, and eventually to remove the plug.
“Sit down. I need to finish this document,” she said without looking up.
Suppressing a groan, I sat again, finding it slightly easier this time but still uncomfortable. Finally, after what felt like an eternity, Anna set her papers aside and patted the dining table.
“You know the drill,” she said.
I laid a towel on the table and climbed up to sit on it. The higher surface forced my feet off the ground, ensuring the plug pushed to its maximum depth. I groaned as the sensation intensified.
Anna giggled, unlocking my cage and slipping it off. My penis sprung to erection. As she poured lube on my swollen penis, she began teasing me slowly, her hand gliding up and down my shaft with deliberate precision. The throbbing caused me to clench my ass involuntarily, drawing a sharp gasp from my lips.
“What’s wrong?” Anna asked, feigning concern.
“Uh … when my penis … you know, throbs, I can feel it inside …,” I said hesitantly.
“You can feel the plug in your ass as I stroke you?” she clarified, her tone playful.
“Yes,” I admitted.
“That’s good. It means they’re connected… your penis and your ass,” she quipped with a laugh. “I always knew that.”
She continued her teasing far longer than usual, occasionally pausing to ask how it felt. Each time, I described the strange but fascinating sensations. When she was satisfied that I’d endured enough, she denied me relief and grabbed an ice pack to cool me down before locking me up again.
“Can’t have you getting too excited,” she murmured as she watched my arousal fade. Once I was sufficiently cooled down, she methodically locked me back into the cage, snapping it shut with a click that sent a familiar wave of resignation through me.
Anna leaned in, brushing her lips against my ear. “You did well tonight,” she whispered. “Now let’s see how much further we can go.”
For the next two and a half weeks, I wore the plugs every day, if not all day. While Anna normally only teased and denied me once a week or so, during my time wearing the plugs it was almost daily. It was relentless. I had worked my way up to the second size, which was a tight fit, taking several days before I could wear it for any significant length of time. By the end, I managed to take the largest one, though only for short periods. I was grateful that Anna was giving me time to adjust.
Over time, the first two sizes became easier to handle, and I rarely used the smallest one anymore. Still, neither the medium nor the largest could be called comfortable. It was obvious that Anna found all this immense amusing. Several times, she ruined me, and the sensation was bizarre… my prostate squeezing involuntarily against the intrusion. I knew that once she started pegging me regularly, I’d eventually begin leaking involuntarily, just as she desired.
Despite everything, I couldn’t deny my excitement for our upcoming wedding night. I was determined to take it like a man… even if she saw me as a virgin woman. She reminded me more than once that she planned to use the five-inch strap-on for our first time together, skipping the smallest one entirely. Since I had been alternating between the medium plug and occasionally the largest, I figured it wouldn’t be too difficult. But I also knew that having something moving inside me was vastly different from the steady presence of a plug.
For the dinner, I had booked a reservation at one of the swankiest restaurants in town—a revolving one perched atop a thirty-story building. From its windows, you could easily see our condo in the distance.
Earlier in the evening, Anna had personally supervised my cleaning, ensuring I was fully prepared. This time, she inserted the plug herself, allowing me to use the medium one since we would be sitting a lot. It wasn’t easy, but it was doable. Then she helped me into the frilly corset with garter straps that I had ordered online—something I had absolutely no experience with.
I couldn’t believe women used to wear these things daily. Instead of my regular cage, she secured one of the tiniest models available. When locked in place, my penis was nearly invisible.
“I don’t want to see your penis tonight,” Anna had told me. “You’re a girl whose virginity I’m going to take.”
The words sent a shiver through me.
Of course, for dinner, I still had to dress like a man—aside from my painted fingernails and toenails. The upside was that there would be no telltale bulge in my pants. With the combination of the plug, the corset, and the cage, my penis was practically pushed inside me, an unfamiliar and disorienting sensation.
The cage was uncomfortable but bearable. Then she slid a pair of white panties up my legs, smiling in satisfaction. I glanced down and realized that I could barely see myself at all. At her command, I had shaved my legs from top to bottom.
Finally, she helped me into white stockings, securing them to the garters before standing back to admire her work.
For the night, I wore a brand-new suit, since none of my old ones fit anymore. I had been a few pounds lighter, and many years younger, when I last needed formal attire. Between the corset and the tie, I felt like quite restricted.
Anna, on the other hand, was stunning. She had chosen a pair of gray pinstriped pants and a matching suit jacket, paired with a crisp white blouse, without a bra. She had worn the outfit to work before, but tonight, with her confident poise and that mischievous glint in her eyes, she radiated dominance. Though she was dressed in rather masculine clothing, she looked nothing like a man. She was gorgeous, no matter what she wore.
Around her neck, she wore the diamond-studded cage key I had bought for her. It was similar to the one her doctor had worn. It rested outside her blouse, catching the candlelight. I noticed a few people glancing at it, their expressions ranging from curiosity to what I suspected was knowing recognition.
The dinner itself was beautiful, candlelit and intimate. We acted like total lovebirds, holding hands for most of the night. It felt different, deeper, more electric… almost as if we were sealing something between us. As we walked through the city after dinner, stopping to kiss on the street, I was aware of the lingering stares.
But neither of us cared.
We had never kissed so much on a date before, and I could feel Anna’s excitement, her anticipation. I knew what the night ahead held for me. And despite my nervousness, I was ready.
To Be Continued
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