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As this weekend began, so did a new chapter in my life and that of my pet. We chose to take some time apart while maintaining our communication; he stayed chaste throughout. Last Sunday, he revealed that for now—and perhaps forever—he can no longer be my slave… yet he still desires us both. Thus, we established a dynamic where I serve as his Key Holder. My control over him is limited, but it suits me well.

We spent a delightful weekend together (which has not quite ended) rebuilding our bond. We sat down and worked out a chastity contract that satisfied us both. We discussed the expectations each of us held for our relationship, and we believe this arrangement can work.

This weekend offered many firsts for us, but what happened last night matters more to me personally. Keep in mind I do not keep him locked in mechanical chastity around the clock just yet; we are still finding a cage that fits him perfectly. Last night after dinner, we were curled up on the couch watching “The Walking Dead,” which many of you have likely been following for a while. I had only recently started it because my schooling last year left little room for leisure.

Regardless, he was wearing his “ring”—a solid metal cock ring with an attached lead that I use occasionally. Deciding to tease him one final time over the weekend, I slipped off the couch, pulled down his pants, and began sucking him. Usually, he signals when he is nearing climax so I can stop, but this time was different. Looking up at me, it was clear he wasn’t in a “submissive” mindset at all; perhaps even Dominant, given how naturally dominant he tends to be. He told me to remove my clothes and lie on the bed.

I didn’t mind indulging him, so I did. He came over, kissed me, and slid his cock inside. It had been about two or three months since he was last in me mentally though, I remained a key holder at heart. When he said he felt “stupid for giving this up,” I wasn’t sure what he meant. Naturally, my mind raced to the worst-case scenarios:

• Was he regretting giving up penetration with me?
• Was he regretting his orgasms?
• Or was he regretting giving me control of his key?

I asked him for clarification. He whispered that he would explain after I had an orgasm for him. So, as he slid in and out, I agreed and let go. My need built quickly, and I gave him what he wanted… but still no explanation. He continued moving inside me while I grew confused. Telling him he wasn’t “allowed to cum,” he replied that he would cum when he decided. This frustrated me slightly, though I wondered if he was testing my resolve. We had discussed earlier in the day how I should react if such a test occurred.

So, I told him to stop, and he didn’t. While it wasn’t threatening, I felt certain he was putting me to the test.

Then… I pushed him away, and his expression confirmed it hadn’t been a mere test. Again, I had failed to read you correctly. He stormed off in anger, refusing further conversation except to say that he felt I didn’t trust him. For my part, it wasn’t about trust; I simply sensed the testing phase.

As he went to bed, I had a drink and pondered his words. Then it dawned on me… he hadn’t been testing me; he was saying he was foolish for giving “us” up! Naturally, I thought, “SHIT!”

All he wanted was intimacy with me, yet I pushed him away. I sent him a few emails and finally joined him in bed 4-5 hours after he fell asleep. Sliding into the sheets beside my curled-up form, I expected to rest quietly. But within moments, he rolled toward me… if he were truly angry, he wouldn’t have done so.

Turning around, I held him as he began rocking against me. “I smiled,” sliding my hand down his pants to find him fully aroused.

Asking him to lie on his back, which he did, I kissed my way down his chest to his cock and took it into my mouth again this time waiting until he was full of desire. Asking softly if he needed me, he looked at me as though I were the foolish one… but answered affirmatively.

Crawling atop him, I slid back inside and bent down to ask if earlier that day he simply wanted to make love with me. He confirmed this, so I apologized. Grasping my hips, he took charge of our rhythm. He provided more pleasure than words can easily convey until I could no longer hold out. Never once did he rush to cum; he only slowed my pace when nearing his own peak.

He made love to me… and remained chaste. The greatest gift anyone could offer was “His love & devotion”.

Beautiful words Lady J, very well written indeed. I look forward to reading more about the pair of you as your journey progresses together.

Hiya You guys just need to relax set aside contracts and chastity devices and just enjoy making LOVE to EACH other! Great sex is amazing and you are putting obstacles in the way . Keep it simple feel the need get your kit of and lock the door and just think about each other . Learn to read each others bodies like it was your own. Tell each other what your feeling and what would make it better.. Just keep it simple and enjoy each other. I get the feeling both of you are desperately in love with each other but can't say the words . Xx Wendy

Last night, it started when I decided to shave his sissy pussy for him for the first time. So I had him ass up face down on the bed with a towel underneath as I took my time shaving away the last of "his man hood." He squirmed quite a bit, but I knew it was driving him mad. When I asked how he felt, he replied, "very sissy." I just smiled. Once finished, I told him to quickly shower off since he had already taken his cleaning shower before shaving; I merely wanted him to remove the excess hair. When he returned, I had him return immediately to position so I could admire my work. Spreading his cheeks open, I slowly tongued his pussy's opening, which instantly made him squirm and moan. He loves when I eat him out, though I didn't do it for long because I had other plans. I wanted to continue stretching him, possibly even fisting him fully. While he was showering, I grabbed a glove and some lube. Applying a small amount of lube to one finger, I began exploring his hole. After a while, I decided to use the inflatable plug. I thought it would help stretch him out better without hurting my fingers too much. So I slipped it in, and over the next 30 minutes we pumped it up 18 times until it was larger than my fist. After letting the air out and teasing him a bit more, I used a plunger device to inject lube into his backside. My fingers slid in easily after using the inflatable plug, yet something still felt off. He suggested placing pillows under his pelvis so we did just that, which was the key factor! With them there, I slipped in much deeper very quickly with no pain for him. Within another 20-30 minutes, I managed to push all the way inside, and the sensation was intense. My hand went completely numb at this point, and when it came time to pull out, the blood rushing back hurt intensely. *Please note: This isn't our first attempt; we have been conditioning for some time now. Do not try fisting someone in a single night.* After he calmed down and went to the bathroom, I lay back on his back this time. Stroking his cock until I ruined three perfect orgasms in a row. He wanted me to milk him, but it was getting late by then. While ruining those moments, he moaned and pawed at the bed bars, afterwards making him lap up his cum from my hands. He blushed and thanked me. The whole night was a wonderful experience for us both, and I am so happy we reached another milestone.