So, following on from the mini-challenges set by Miss Geena and Mrs Annie after my first year as a volunteer, the next task came from Miss Autumn — and this one started differently.

Instead of jumping straight in, she asked me to send a single photo that captured as many elements of her vision as possible. Taking inspiration from some of her posts, I went for a literal “strapped to the dining room table” setup: my behind already reddened (though likely not her  normal standard), with one rather large dildo positioned behind me. I even managed to get it slightly in for the shot.

The goal was clear — helpless, held in place, completely at her mercy, with no control over when it would stop… and a very obvious hint that we could skip the beginner training dildo and jump straight to the next level. A little after my submission I received a response, kind of a check list / shopping list of things required. Once I confirmed I had everything, we moved on to the action challenge itself.

The challenge was broken into three distinct parts, all with one clear underlying aim: make me scream. (Spoiler: I fell short on that one — maybe some of you reading can do better?)

Part 1 – Discipline

Simple but effective.

I was to insert my largest plug, add rings to my balls stretch by then out and reddened my behind to a decent level. Once it was glowing nicely, I was to record a short video of 11 additional strikes, counting each one out loud.

Part 2 – Caged Cock Attention

This part came with extras notes: stay plugged, add nipple clamps, and some body writing. I also had to downsize into a much smaller cage — a tiny nub barely an inch long.

The main objective was to spend time exploring with vibrators and toys: discovering which sensations made me throb hardest, which caused the most strain against the cage, and which combinations worked best. I was told that if I felt close to a caged orgasm, I should push for it — but only if it was captured on video. I stuck strictly to battery-powered toys and spent around 15 minutes testing and playing. No release this time, but I learned a few bits that worked well.

The finale for this section was another short video — basically a show-and-tell where my desperate, caged body did most of the talking.

Part 3 – The Double Fuck

This was probably the most intense part. The title says it all.

I was to be properly filled from behind using my fucking machine (it’s cheap and cheerful, but it gets the job done). Requirements included keeping my ass red from Part 1 and wearing the nipple clamps unless they genuinely needed removing.

Scene 1: While being taken from behind, I had to “make love” to a second cock from the front — a hands-free spit-roast setup. I’m far from experienced at this, but I gave it everything I had.

Scene 2: Using a whip and/or paddle, I was to add fresh marks to my back and behind while still mounted on the machine. Logistics were tricky in that position, but there were parts of me was fully on board definitely something I’d love to explore deeper in the future.

Scene 3: Bring back the vibrators from Part 2 and use them on my caged cock while the machine continued pounding me from behind. The combined sensations were incredible, even if they still weren’t quite enough to push me over the edge.

As per the rest, I had to film short show-and-tell clips for each item and submit everything for review.

After chopping, trimming, and double-checking that I’d followed every instruction, I sent it all in. I already knew it probably wasn’t going to be a “pass” — and that was okay. There was certainly reward in the interaction and the journey:  the creative problem-solving, the physical challenge, and exploring more about myself.

Thanks for reading!