Zeek’s Femdom Adventure 3: One Dildo-Gag. Three Addresses.

In late May 2024, I faced my third While My Mistress Was Away challenge. It was a short trip—just three nights—and I thought maybe, just maybe, I’d get off easy this time. Nope.

Annie left me with a box to open after she was gone. Inside, I found a piece of paper with three addresses—one for each night she’d be away. And next to it was a brand-new dildo face harness. I hadn’t used one of those in years, and I had a sinking feeling I’d be breaking it in over the next three nights.

Zeek’s Adventure #3: While Mistress Was Away for 3 Nights

The first address was familiar—her friend V’s house again. But the other two addresses? Complete mysteries, and one of them turned into more of a nightmare than I’d expected.

Even though I technically “failed” the last challenge’s masturbation task, I felt like I had truly won—after all, I lasted far longer than Annie had anticipated, and my “punishment” was something I actually enjoyed. But this time, in Adventure 3, I experienced my first outright failure.

Address #1: Her Friend V, Again

On the first night, I knew the address—it was V’s house. I arrived right on time at 10 p.m., and V opened the door with Annie on FaceTime, just like before. I was surprised to see Annie on the call, given that it was 1 a.m. where she was, but it was clear she was eager to watch.

This time, Annie explained that I wasn’t there to perform for entertainment, but to please V using the dildo face harness. Now, I actually enjoy going down on women, so this gag was a frustrating experience for me. I could smell V, but I was reduced to nothing more than a tool, bobbing my head as the dildo did the work. It was uncomfortable and kind of painful, especially when V grabbed my hair, shoving my face into her and pulling me back roughly. My neck was getting sore, and I was genuinely pissed off by the end.

Eventually, she orgasmed and pushed me off. I took off the gag, cleaned it up, and headed home, tired and sore. It was a rough start, and I still had two more nights to get through.

Mission accomplished.

Address #2: The Lesbian Couple

I didn’t recognize the second address, but when I got there, I realized it was the lesbian couple from the dinner party at Jeff and Melody’s, where I’d jacked off in front of everyone. I’ll be honest—it turned out to be a much better night than I expected. They were laid-back, and after listening to some music and getting high together, it was time for me to get to work.

Only one of them wanted to take the dildo strapped to my face. The other wasn’t into penetration, so she stuck to having her face buried between her girlfriend’s legs. The one who wanted me shoved the dildo deep inside her, moaning as I bobbed my head up and down like a fuck toy, her pussy wet and dripping all over my face. Meanwhile, her girlfriend rode her face, moaning as she got eaten out.

I could tell both of them came a couple of times while my own cock was rock hard, painfully pressing against my jeans, with no release in sight.

Mission accomplished.

Address #3: My Nightmare Failure

I had no idea what to expect with the third and final address on the list. A quick search on Google Maps didn’t give me much confidence—it was in a pretty rough part of town, with a dark and unwelcoming apartment building staring back at me from street view.

So, on the last night of the challenge, I arrived at 10:30, just as instructed. When the door opened, I was completely thrown off. Standing there was Jace—my wife’s much younger “cousin.” He’s not actually her cousin, just a family friend’s kid she used to babysit back when we were in high school. I barely interacted with him back then, but fast forward to now, I knew way more about Jace than I ever wanted to.

Jace stayed with us for a couple of weeks last year, and during that time, I got a front-row seat to his wild, no-limits sexual encounters with guys he’d bring home. He had no concept of boundaries or timing, and I’d walked in on some pretty intense scenes. It was clear that he shared Annie’s sadistic and dominant traits, but with much rougher edges.

Jace pulled out his phone and put Annie on FaceTime. What she said next was the final nail in the coffin. My last task? Use the dildo gag on Jace. She said it so casually, like it was no big deal at all, telling me that Jace would be a “good boy” and just lie there while I fucked him in the ass with the dildo strapped to my face. They’d even set a 15-minute timer, with Annie staying on the line to make sure everything went smoothly.

But there was no way. I didn’t even take a second to think about it—I just knew I wasn’t doing it. I apologized, backed out of there, and left.

Now, I know Annie was 99.9% sure I’d fail here, and that was certainly her plan. I knew she wanted me to fail, and yet I still felt awful, knowing I was disobeying Annie and ending the challenge this way. But I had no idea just how bad I was going to feel later. 

Mission Failed

Punished for Failure

My punishment for failing the third challenge was harsh. At first, I got the cold-shoulder. There was no sex, no intimacy—nothing. When she finally decided to take action, she had me bend over the spanking bench while she paddled my ass. At first, I was into it, enjoying the sting, but she kept going. Hard. It reached that point where the pain overtook the pleasure, and I skipped right past subspace and was really screaming.

For the first time in a long time, I used my safeword—the one that signals a break. Annie obliged, laughing a little, but when she saw the welt she’d raised on my ass, I think she felt a bit bad. We don’t usually take things that far. Still, she wasn’t done. She paddled me for a few more minutes before finally letting me up. No orgasm for me, though—she made sure I pleased her with my mouth that night instead.

The next morning, she woke me up with her hands on me, and we made love, her riding me. But after we were done, she informed me that this was just a break in my punishment—something for her. My punishment was far from over, and she hinted that with her next trip coming up, it would continue into Adventure #4.

It’s All Play – Mostly

I want to remind readers, or maybe clarify if I haven’t made this clear before: my wife and I are deeply, passionately in love. While I am hopelessly devoted to her, willing to make any sacrifice, I know she feels the same about me. We are partners in every sense of the word. However, we’ve found that our relationship works best when we integrate the Dominance and submission (D/s) dynamic into as many aspects of our lives as possible.

Take, for example, the latest “command” she gave me. She knew I wouldn’t be able to follow through, and she was counting on that slip-up as a way to initiate a period of punishments. Not that she ever really needs a reason, but it adds to the fun for both of us when we have an ongoing challenge like this one.

So yes, I’m in trouble, and I’m being punished, but it’s important to understand that while punishment seeps into many parts of our relationship, it doesn’t consume it entirely. There’s a balance. At its core, our dynamic is rooted in love and mutual respect, and that’s what makes it all work.