Zeek’s Femdom Adventure 2: Forced Masturbation Humiliation

The second opportunity for Annie to embarrass me with her challenges came pretty quickly after that first 3-week event. It was mid-May 2024, and she had to travel for an entire week. This time, the week was all about forced masturbation at the most inconvenient and awkward moments!

Zeek’s Adventure #2: While Mistress Was Away for About a Week

The challenge for this week was laid out in a single email Annie sent me the morning she left for the airport. The rules were simple but intense: any time she texted me the command CUM NOW, she’d start a timer. I had exactly 2 minutes to find a spot where I could FaceTime her and start masturbating. Then, once the call began, I had 5 minutes to cum. If I succeeded, I won; if not, I failed.

Now, I’m naturally not a quick cummer—normally a good thing—but this challenge made it tricky. Annie had trained me to hold an erection for extended periods, so cumming quickly wasn’t something I was used to. But I had my ways. Basically, I had to keep myself as horny as possible all week (which isn’t too difficult considering my job), and then just jerk like crazy whenever she gave the command.

The idea was to successfully complete the task every single time. Once I failed, the challenge would be over. Annie mentioned that my reward or punishment would be based on how far I got through the week before my inevitable failure. It definitely sounded like she expected me to fail at some point, but I was determined to prove her wrong.

At first, it was manageable. The first couple of days, all the CUM NOW sessions happened while I was at home. Since I work from home, taking a few minutes to jerk off wasn’t too hard, especially with Annie watching on FaceTime. But as the week progressed, things got more complicated. She was definitely using the phone tracker to choose the most inopportune moments for me to get the job done.

Here are some of the most Memorable CUM NOW moments of the week:

The Grocery Store

I was right in the middle of the dairy aisle, trying to finish up my shopping, when I got the dreaded text: CUM NOW. My heart raced as I quickly abandoned my cart and bolted to the bathroom. Once inside a stall, I frantically dialed Annie on FaceTime. As soon as she answered, I put a finger to my lips, silently begging her to stay quiet while I got the job done. Miraculously, I managed to jerk off and finish in time, right there in a grocery store bathroom.

Mission accomplished.

The Side of the Freeway

One of the more nerve-wracking moments came when I was stuck in traffic on the freeway during rush hour. I hadn’t planned on being caught in traffic, but I had to run across town to pick up a part for my computer, and sure enough, when Annie noticed my location on her tracker, the text came through: CUM NOW.

I quickly pulled off to the side of the freeway, dialed her up, and went to work right there in my car as traffic crawled by in the lanes next to me. It was a close call, but once again—Mission accomplished..

Mission accomplished.

In the Storage Unit

We were still renting a storage unit from our recent move, and I had one last load to clear out before closing the rental. Annie knew I was there, of course, and like clockwork, she sent the text. I was actually sitting in the unit, waiting for it—fully expecting the challenge to come at that moment.

Sitting on a chair inside the unit, with the door wide open, I jerked off right there and shot my load on the unit’s concrete floor. After finishing the task, I packed up the rest of our stuff, checked out of the unit, and left. To this day, I still wonder if the clerk noticed the wet spot when they inspected the unit for any damage!

Mission accomplished.

Conference Call

Most of the time, my work is pretty isolated, but once a month, I have to attend an all-company Zoom meeting where I’m one of many faces in the grid. Annie knew the exact time of this meeting, and right in the middle of it, she sent the text.

I was prepared. Naked from the waist down, with a vibrating sleeve near my desk, I managed to FaceTime her while keeping my face stoic on camera. I used the sleeve, shot my load, and all the while, I maintained my professional composure on the Zoom call.

Mission Accomplished.

Driving the Neighbor

One of the most shocking moments of the week happened while I was driving one of our elderly neighbors, an older woman who lives alone, on an errand in our handicap van. In the middle of the drive, I got the CUM NOW text. I figured there was no way to do it in time, and I mentally accepted that this was where I’d lose the competition.

But then she spoke up. She told me she knew I had just gotten a text from Annie and that she didn’t want me to lose the challenge. I was stunned—how the hell did she know? She told me to pull over and “take care of it” right there in the van. I was appalled, horrified that Annie had told her about our dynamic, about me, about this! And then she said something I’ll never forget: “Don’t worry honey, I’ll just watch.”

And that’s exactly what she did.

Mission accomplished.

Dinner with Jeff and Melody

Annie had recently befriended a younger couple, Jeff and Melody, from the local kink community. Jeff typically dominates Melody, though they enjoy switching things up. I was working on a website project for them, and we’d originally planned to meet over the phone to discuss it. But Annie had other plans—she arranged for me to have dinner with them instead.

I had a feeling she’d try to catch me off guard during the dinner, so I wanted to park closeby. However, they lived in a trendy area with limted street parking, and ended up blocks away. I wasn’t too worried, I figured I could always find an empty bedroom or bathroom to take care of things.

But when I got there, I realized their apartment was in a converted warehouse—basically one big open studio space with only the bathroom offering any privacy. To make matters worse, they’d invited two of their female friends, a couple, to join us.

As the night went on and the beers flowed, I started to relax, enjoying the conversation. Suddenly, I noticed Jeff got a text and immediately excused himself to the restroom. Right then, I got the dreaded text from Annie: CUM NOW. Fuck.

I quickly knocked on the bathroom door, but Jeff yelled back that he’d need a few minutes. I turned around and realized the rest of the dinner party was watching me—all three women grinning. They knew.

With no other choice, I called Annie on FaceTime. She was smiling, asking if I was ready to give up. I wasn’t about to quit. I pulled down my shorts right there, in front of everyone, and started masturbating. Tipsy and determined, I dropped to my knees as the room watched—Annie on FaceTime and Jeff standing in the doorway, grinning. I finished right there on their floor.

Mission accomplished.

And Then I Lost

As the week was coming to a close, I was feeling pretty confident that I might actually win the challenge. I was at home and about to head out to Home Depot when I got the text CUM NOW. I figured Annie had screwed up, since I wasn’t out yet, so I called her and took care of it quickly at home.

Mission accomplished.

Afterward, I headed to Home Depot, thinking I was in the clear for a while. But just 30 minutes after I’d hung up with her, while walking down the aisles, I got the text again. I ran to the bathroom, but this time, I was struggling. I just couldn’t get hard—come on, I need more recovery time than that! Annie knew this.

The clock was ticking, and with only a semi-erection to show for it, I heard a voice from the stall next to me. I thought I was alone, but then some guy asked, “Need help?” That was it for me—I lost it. I said, “No, thank you,” pulled up my pants, and walked out. Annie was still on FaceTime, laughing, as I reached my car.

Mission failure.

My Punishment/Reward

When Annie came home, I got a mix of punishment and reward. She strapped me to the bed and started edging me, making it clear she wasn’t impressed with how quickly I had been cumming during the challenge. She teased that if I didn’t improve, she might start calling me her “5-minute boy.” I tried to argue that I had been cumming quickly because she’d ordered me to, but it was pointless.

She set a timer for 90 minutes and told me she’d edge me until the time ran out. Only then, on her command, would I be allowed to cum.

The edging session was pure torture, but I gritted my teeth and bore it. After the timer went off, she let me cum, and the release was more intense than any before it.

As my spent cock twitched in exhaustion, Annie praised me for my efforts that week. She said she was impressed by my determination and creativity, but also loved the desperation in my eyes towards the end. And with that, my 2nd Adventure came to a close.