Zeek’s Femdom Adventure 4: Punished for 9 Days Straight

The fourth challenge hit in early June, about 8 or 9 days after Annie had been gone the last time. Let’s be clear—I was still deep in the doghouse, and she wasn’t shy about letting me know it. She really hates being told “no,” and by refusing to complete the third challenge and not going to see Jace with my dildo-gag, I’d basically said no to her face. Not good.

So, when she left for her 9-day trip, I was seriously on edge about what she had in store. The night before, we made love, which was a relief. Another imporant point of clarity: Even though I was in “trouble,” I wasn’t banished to the couch or anything. This was still in the realm of play-trouble—at least, I hoped it was staying that way.

Just before heading to the airport, she dropped a bomb. I’d be getting my challenge instructions by email shortly. And this wasn’t just any challenge—it was 9 days of punishment. But, if I obeyed her, I could finally earn back my “good boy” status. Oh, boy…

Day One

The first email about my punishment came through about two hours after she’d left. It laid out a pretty simple choice: I could either visit Jace, or wear clothespins on my nipples all day. That one was a no-brainer. I had no clue what she planned for me if I went to see Jace, and I wasn’t in a hurry to find out. As I mentioned before, Jace is my wife’s “little cousin”—but they aren’t actually related, just family friends from when she used to babysit him. He’s a great guy, very gay, and Annie had tasked me with doing something to him during the last challenge that I flat-out refused. So yeah, I think she knew damn well which option I was going to pick.

That day was mostly spent working in my office, doing design work on a few sites. I’ve got a camera set up at my desk—no, not the one I use for Zoom meetings, this one’s private, connected to the web so Annie can check in on me anytime she wants. And I’ll admit, I tend to work in some state of undress anyway—boxers are my go-to when I’m cranking out long work sessions. So, I clipped those fuckers on and got to work, knowing Annie could keep tabs on me all day.

I’m not gonna lie—several hours with clothespins digging into my nipples was a whole new level of pain. By the end of it, my nipples were on fire. Thankfully, Annie texted me that evening, telling me I was done. She even gave me careful instructions on how to remove the pins, apply some Aloe from her nightstand, and text her when I was okay. God, I love her.

Day Two

I got my next email bright and early: another choice—visit Jace, or wear the ballrings all day. Yeah, another easy decision. Now, let’s get something clear: I don’t want any hate mail about being homophobic. I’m super open-minded, and I’ve been in sexual situations where other men were involved, but always in the context of serving a woman. I can appreciate the male body and even find some guys sexy. Back when we were younger, Annie was convinced I might be bisexual. She pushed the idea a bit, but we never quite crossed that line.

But here’s the deal—I’m very into women, especially Annie. I’m not in a place where I’m ready to explore my sexuality with men, plain and simple. And if I were, Jace sure as hell wouldn’t be the guy I’d pick. The stuff he does to men scares the shit out of me. So yeah, I’m avoiding him for self-preservation, not because of homophobia.

Now, about the “ballrings.” This thing is like a jelly-like ring designed to stretch your balls lower. Let me tell you, I was pretty happy with how my balls hung naturally, but Annie had other ideas. She jokes that she wants them to hang lower, so here we are. We don’t use it often, and I hate putting it on myself—Annie is way better at it. But I sucked it up, got the damn thing on, and wore it the whole day.

Thankfully, it was another day alone in the office, so I just pooh-beared it—shirt on top, nothing below. I even had a conference call with Levi and duckie that afternoon, and neither of them had any clue about my predicament. I guess they might know now though!

Day Three

I was starting to see the pattern in Annie’s choices. This time it was: visit Jace, or jerk off five times. Of course, if I chose the jerk-off option, there were additional instructions—I had to collect all my spunk and add it to my evening protein shake. I’ll admit, I hesitated for a split second, considering the visit, but quickly ruled it out. Visiting Jace could be anything from a casual chat to something far more boundary-pushing. So, again, the choice was simple—thank god I had plenty of good lube on hand.

Let me tell you, jerking off five times in one day is no walk in the park. I drank plenty of water and, yeah, watched a lot of porn. It’s kind of convenient that my work already involves a bunch of adult content—it made the task a little easier. By the end of the day, I’d managed to get the job done, though my dick was sore as hell.

As for the shake? Meh. By this point, I’ve gotten pretty used to her making me consume my cum, so it wasn’t anything new. I threw in some extra ingredients to make sure the taste was muted. It worked well enough.

Day Four

Once again, I was faced with a choice involving Jace. Honestly, at this point, I was starting to wonder if Jace even knew about any of this—Annie had to realize I just wasn’t going to go there. So, my other option? Visit her friend V. I thought, “Not too bad,” considering I’d already masturbated in front of her once, and used the dildo gag on her during my second visit. How much worse could it get?

Well, turns out it was rougher than I expected. When I got there, V had a ping pong table set up right in her living room. She told me to drop my pants and bend over the table. Then, she went to town on my ass with the paddles. Let me tell you, those things sting like hell, and I was yelping by the end. V has some serious arm strength and didn’t hold back—my ass was on fire. I know Annie could hurt me way more than she does, and I’m grateful for her restraint. V? Not so restrained, and I was in serious pain on the drive home. The next day, I was especially thankful for my standing desk!

At that point, I was really starting to hope Annie wouldn’t send me back to V’s any time soon.

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Day Five

My choice, aside from the absolute no-go visit to Jace, was to clean my neighbor’s house for four hours…in my maid costume. FUCK. The neighbor? Yep, the same sweet old lady I drove around when I had to jerk off in the van. And yes, she was definitely into it.

When I got there, she looked disappointed that I was in jeans and a t-shirt—she knew what was coming. I explained that I didn’t want to cross the street in my maid outfit and asked if I could change in her bathroom. She smiled, all innocent-looking, and said, “Just change here, dear. I’ve already seen it.”

So yeah, I was probably red in the face, but I sucked it up and stripped down, keeping my boxers on while I threw on the maid outfit. Let me just say, it’s a pretty humiliating uniform, and I do my best not to bend over in it. She got a real kick out of it and mostly had me dust the living room. Thankfully, she already has a housekeeper, so the work wasn’t too hard.

After about 30 minutes, she asked me to haul up some boxes from the basement. When I finished, she thanked me and said I could leave since there wasn’t any more work. But I still had hours left, so I asked if I could stay and watch her shows with her. She said yes, as long as I didn’t talk during the show—only during commercials.

So, I grabbed some snacks from the kitchen, and we spent the next few hours watching TV and chatting during breaks. I actually kind of forgot I was wearing that ridiculous maid dress. And thank god, she didn’t make me answer the door for the FedEx guy!

Day Six

By Day 6, my choices were really becoming more about picking the lesser evil. Of course, one option was visiting Jace—again. But the more realistic choice? Worshiping V’s feet. My ass was still sore from her paddling two nights before, but I went with it.

Now, I’m not a huge foot guy, but being forced into it does turn me on. It’s this weird mix of being grossed out and aroused at the same time—if that makes sense. V’s feet, though, were genuinely beautiful. It was clear she takes care of them, getting pedicures, and her toenails were perfectly painted. At first, I was into it, massaging her feet and seeing how much she enjoyed it.

But then she got impatient, fully embracing this “foot dominatrix” persona—maybe a little too much. She barked at me to worship her feet, then shoved them right in my face. I knew what I had to do.

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Day Seven

My choice for the day was either visit Jace (again) or tackle the garden shed project. I hated the idea of the shed—it’s technically this old garage at the back of our property, filled with junk that was there when we moved in. It’s been on my to-do list forever, and Annie knew I had the day off, so she figured I had time to deal with it.

I did consider visiting Jace, thinking maybe it’d be something simple this time. But then I started running through the possible scenarios, especially with how Annie seems dead set on breaking down my barriers and pushing my hard limits. In the end, I figured the shed was the safer option.

It was a long, exhausting day. Honestly, I only got halfway through the mess, but I felt good about making some progress. I even decided that, since I had the next day off too, I’d work on finishing it—unless, of course, Day 8’s challenge turned out to be a total nightmare!

Day Eight

So, my choices were between visiting Jace—of course—or her friend “Flower.” I’m not sure why I put that in quotes; honestly, it might be her real name. That’s the only name I’ve ever known her by. Flower’s older than us, and she’s Annie’s “hippy friend.” She lives out on some farm, a bit of a drive from the city. We visit occasionally. I love the herb she grows, and Annie enjoys the wine and conversation.

Now, Flower’s one of the rare exceptions I’ve had sexual activity with in the past decade. A couple of times, when we were high and in the mood, Annie had me give Flower a full-body massage—fingering included. So, I figured that’s what I was in for again: getting high and making her cum with my expert fingering skills. I was actually looking forward to it, despite some of Flower’s…less desirable traits.

Let me be clear, I’m not worried she’ll read this—Flower doesn’t have the internet and is a proud anti-screen-time, off-the-grid hippy farmer. She fully embraces that lifestyle, which includes a bathing schedule I’d call generous if it happens occasionally. Plus, she’s quite furry, if you catch my drift. But honestly, it’s an interesting change from Annie’s perfectly trimmed, beautiful pussy.

So, I arrived at Flower’s farm that night, fully expecting to get stoned and finger her until she came. We wasted no time getting high as hell, and then she asked me if I was ready to taste pussy.

Wait—taste? Did she say taste? I stammered, trying to explain that Annie probably meant with my hands, like we’ve done before. It’s been a long time since I’ve gone down on anyone else. But Flower just smiled, opened her legs, and pulled up her skirt, revealing she wasn’t wearing any panties. She laid back on the couch, waiting for me.

I wanted to call Annie to confirm, and as if reading my mind, Flower told me to FaceTime her now. I did. Annie picked up, already expecting my call.

The first thing she said was, “It would’ve just been a beer tasting with Jace at a new brewery. Instead, you’re going to be doing some pussy tasting. Now, I’ve asked Flower to share herself with you, and I expect you to be a good boy.”

She explained that I was being “honored” with tasting my first pussy outside of our marriage in so long, and that I had to make Flower cum to complete the task. I did manage to accomplish the task. I’ll say this—it wasn’t a horrible experience, but it definitely wasn’t my favorite either. I’m thankful my wife gave me the opportunity to serve another woman in this way, but I’m even more thankful she’ll likely have me doing it with others in future challenges!

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Day Nine

The choice was either visiting Jace (no surprise there) or having dinner with Jeff and Annie—the same couple I had to jerk off in front of during the last challenge. This time, their friends Rieley and Maddie, the lesbian couple from the previous dinner, would be there too.

I was curious about what they had planned for me this time, and that curiosity was answered when Annie called Jeff’s phone at the end of dinner. My final punishment? The one I chose? Annie had lent Jeff her bullwhip, and all four of them were going to take turns whipping me. Annie was so giddy as she explained how excited her friends were to participate. To top it off, Annie had finished her meetings early and was able to watch the entire thing.

I’m not going to lie—this one hurt, and it brought me closer to breaking than anything else so far. Jeff is an experienced BDSM master, and normally, it’s Annie who subs for him. I wasn’t worried about crossing any inappropriate lines; Jeff’s as straight as they come. But I learned that sadism doesn’t care about gender. Jeff was all about inflicting pain, and he did it well. And that was just the start – each of the three women took their turns as well.

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My Wife’s Return

Annie came home the next day, and the first thing she did was order me naked—so she could inspect my body and the damage I’d incurred at the hands of her friends. It was all by her design, and she seemed genuinely pleased as she looked at the fresh whip marks from the previous night’s session. Some had resulted in welts across my back, and she took particular interest in the fading marks on my ass and the deeper, darker bruising there.

She took her time tending to my sores and bruises, and in that gentle but commanding way, she told me I was her “good boy,” even though I never chose to visit Jace. She explained that, just like the time when I would’ve gone beer tasting with him, all the other potential visits were simple, vanilla activities that wouldn’t have involved anything sexual. I’m still not sure if I believe her, but I’ll take it at face value.

Looking back at the 9 days of punishments, I’m proud of what I accomplished and amazed at what I endured. Sure, I’m a bit embarrassed about some of the tears, screams, and choice words that slipped out in front of others, but that’s just part of the life of a masochistic sub married to one of the most wonderful, dominant women in the world!