The Holiday Special - The Tree of Keys (Patreon)

The woman with the blue eyes in the house down the lane always hosted a holiday party. She’d hang the garland on the railings of the house, work hard to get up a large Christmas tree and even decorate the fireplace in her large house with Christmas stockings filled with candy and small nick nacks.

She looked forward to this holiday party because everyone in the local community was invited. They didn’t have to bring anything, after all, the woman with the blue eyes would be supplying the gingerbread cookies, hot chocolate and holiday foods. She would even be coordinating the white elephant, the secret santa and the other holiday games adults tend to pretend to be mildly entertained by when drunk off of warm basic mulled wine.

But the real treat was the Christmas tree she placed in the middle of the party room. The tree lit up with bright white lights stood over ten feet tall and became the centerpiece of the party. It wasn’t just because of the perfect way it was cut, or the way the lights shined brightly among the brilliant holiday ambiance, it was because this tree didn’t have ornaments.

Instead, on the tree where hundreds of keys, thin slender keys just glittering in the light of the room.

Every year, when the woman with the blue eyes hosted this party, unsuspecting guests would ask why no ornaments? Why is the tree filled with keys? But she’d simply laugh and offer her guests more wine. But there were others, the ones she had trapped with her wickedly clever games, who knew. They knew what was happening. And they were scared.

Yes, you remember her… the woman in the college town who would lock unsuspecting boys’ cocks when they were least expecting it. Yes, she was the one who would, as they struggled tied to her bed, pull out the pink Megamax, tell them to lift up and fasten the thick, bulky, crinkly plastic prison over their caged cocks and take a photo.

And that’s why I was standing outside of the house at this very moment, pacing back and forth staring at the invitation in my hand, daring myself to enter the house.

Last week I had failed the test… again.

She had given me a warning after she’d trapped me in diapers during our one night stand. “Each time I see you, you’d better be diapered,” she had said, staring into my panicked eyes. “If you’re not, that’s an extra week that the cage stays on. If you are diapered each time I see you, I’ll unlock you for a bit.”

I’d panicked and rushed home, ripping the diaper off of me and tossing it in the trash. There was no way in hell I was going to wear and use a diaper for the next few weeks as she decided what to do with me.

But try as hard as I must, I couldn’t free my cock from the cage that felt like a vice grip on my manhood. For the next week, every thought of an erection was stilted by the painful metal spikes in the cage. I woke up over and over in the middle of the night, my cock straining to break free. After two weeks of pain, it was as if my cock stopped trying to get hard and instead an intense horniness took over deep inside my gut. I needed to get this cage off of me… and fast.

But one night, there was a knock at my door. I grabbed some sweatpants and headed to the door and opened it, curious who would be disturbing me at this hour.

I gasped when I saw who it was. It was her, the woman with the blue eyes.

She took a step into my apartment and simply asked, “Have you been a good boy?”

I stuttered something trying to make an excuse for why now was not a good time to check on me. But she was adamant.

“Are you wearing your diapers like a good boy?” She asked, reaching for my sweatpants. “If you are, your cage can come off.”

My heart dropped. Of course I wasn’t wearing diapers. I wasn’t a baby, she didn’t control me. But her hand slipped into my sweatpants, cradled my balls for a moment and her fingernails tapped the edge of the cage. I could hear the disappointment in her voice. Even her soft hand felt disappointed.

My cocked twitched in the cage, startled by the first bit of sexual contact in many weeks.

But the feeling was short lived because she withdrew her hand instantly. “I guess that’s another six weeks then.” And before I could say anything she was stepping off my front porch and stalking down the walkway.

I ran after her, “Wait, hold on… please!” I begged. “Unlock me, I’ll do anything.”

The woman with the blue eyes swirled around and looked me dead in the eyes. “Then wear your diapers.” And with that, she was gone.

I failed three more times after that, stubbornly refusing to wear diapers like a baby. She showed up after a soccer game where I had scored the winning goal. She showed up in the middle of my chemistry test. She had shown up, waking me from my afternoon nap. Each time she’d reach into my sweatpant and squeeze my chastity cage, make that disappointed noise with her teeth and extend my sentence.

After four months, I was desperate. My boxers were constantly sticky with pre-cum, I was always leaking. I felt like I was always on edge, I could burst at a moment's notice, which is why I found myself one day, laying back and putting on one of the thick, crinkly pink diapers she’d left for me.

This was humiliating.

I wore them all the time as the woman with the blue eyes had demanded. I still remember what it was like to wet the diaper, my diaper, for the first time. I sat down and released the pee that was inside of me. The relief I felt was incredible, and the unine trickled down my legs causing the interior of the diaper to swell. I felt foolish waddling around looking for another diaper to change into.

Sometimes, I’d plan poorly and be out of diapers after I’d used up my last one. I’d rush over to the woman’s house as fast as possible, hoping to catch her at home. Hoping that she’d be inside and have a pack that I could have so I could continue playing this stupid game.

I was lucky. This time, she opened the door, grinning wickedly in my direction, innocently asking me if everything was okay.

I nodded and mumbled that I needed more diapers.

“More what?” She asked, frowning.

She knew damn well what I had said. This was part of the humiliation she’d inflicted upon me day after day after day.

“I need more diapers.” Then out of desperation as I knew my padding was soaked, “Please.”

She let me in and mentioned she was cooking lunch and that I should sit down and eat. Then she’d let me on my merry way. But first she handed me a glass of juice and said to drink up. It’ll cleanse your palate for lunch.

Then she instructed me to remove my clothes. “I want to make sure you’re wearing your diapers,” she said a materafactly.

I tried to tell her I obviously was, but she pointed to the door and said I could leave if I didn’t want to comply.

So I took off my pants and shirt and revealed the swollen pink diaper underneath. It squished between my legs as I stood there under her piercing gaze.

She nodded and left the room.

I drank quickly, eager to spend as little time in this house as possible. But she took forever in the kitchen. Half an hour went by until she returned with two simple sandwiches and potato chips.

As we ate in silence I tried to speak up, tried to gather the courage to tell her I didn’t want to play her games anymore. Tried to apologize whatever it was that I had done to deserve this. But sitting at the table, in just a diaper made me feel silly. I could feel the cool air against my legs and each time I glanced at my lap I could see the thick, crinkly diaper glaring at me.

It’s hard to feel tough while wearing a pee soaked, heavy diaper near a fully clothed attractive woman.

Then my stomach rumbled. I looked up in shock in time to see her blue eyes boring into my soul. I tried to stay calm, but I knew this feeling. This was the feeling I got every morning when I took my morning trip to the restroom.

But this was unusual. I didn’t usually have to use the restroom like this in the afternoon. But then I remembered… the drink she’d given me.

I stood up quickly, refusing to do such a humiliating act in front of this woman. But I realized I had no place to go. If I left, I’d be in just my diapers on a busy college campus. Messing my diapers in the middle of campus walk wasn’t ideal. I felt a cramp rush through me.

The woman stood up and came up to me. She took her hand and squeezed the front of my diaper, causing my caged member to twitch aggressively.

Another cramp rolled through me. And soon I couldn’t help it. With my face burning red, I squared slightly and felt the mess start to ooze out of me and into my waiting diaper. Soon I was in a deeper squat as she reached underneath me and patted my butt as helplessly filled my diaper.

She stroked my padding, patted my back and said softly, “Good baby…” as I kept pushing until I felt relief. I couldn’t bear to look at her when I was finished. But that didn’t matter. When I was done she handed me back my clothes and pointed to the pack of diapers she had put on the table and said I could come back anytime.

Or I could start ordering my own diapers. The choice was mine.

It wasn’t much of a choice, the last thing I needed was a case of diapers arriving in the student mailroom for me to pick up.

But soon a week became four and one month became two or three. After four months, I was wearing diapers full time, determined to get out of the chastity cage. I was to be what she referred to as a good boy. I waddled to class. I squished my way to parties after school, wearing sweatpants to try and cover up the obvious bulge that was forcing my legs apart. I didn’t dare try and order something thinner and more discrete, terrified I’d have to change in public one day. The woman with the blue eyes kept coming to my door, coming to class, coming to clubs, performing her diaper checks. Each time she’d squeeze my padding and smile. Sometimes she’d probe around and feel the mess I had made just moments earlier.

She’d relish in the times I had to come back to her house for a change and force me to mess at the table with her. Each time laughing and then replenishing my stock of diapers for the week.

But soon, right when the holiday arrived, there was hope.

I received the embossed invitation that said I was invited back to her home, where I could get unlocked. I had one chance, the invitation said. One change to be free from the cage.

Damn right I was going to take it.

Which is why I finally found the courage to enter the house and mingle with the other guests. As I milled around I waited for the woman with the blue eyes to give me my chance, I nibbled on some crackers. I could have sworn there were a lot of men at this party but brushed them out of my mind when the woman with the blue eyes approached me and said now was my chance.

“You have two options,” she said, smiling at me as I looked into her blue eyes. “You can either stay locked for another sixty days which then you can be free for a week, or you can try and get your key back.”

“I want the key back,” I said quickly.

“Wait…” she said. “Calm down for a second. If you fail to get the right key, then it’s another three months of diapered chastity for you.”

“I want the key now,” I said. I wasn’t going to miss my chance.

She led me to the Christmas tree, the one that was ten feet tall with the keys on it. When I looked closer I gasped. They were all chastity device keys. And one of the hundreds of keys had to be mine. I reazlied instantly my horninees had gotten me in trouble. I looked around and grabbed a key, praying to god it was the right one.

“Are you sure that's the right one?” She asked, looking at me closely. My eyes darted around the tree. How many men in this town were locked by this crazy woman?

I snatched another key, thinking it looked like the one that would fit the device holding my penis prisoner.

She led me back to the bedroom where she had me lay down and untapped my awfully full diaper. This time my cock didn’t stir once, now used to the confines of the cage. Slowly she put the key into the lock and gave it a turn.

Only it wouldn't turn.

She tried again.

Nothing happened.

It was the wrong key.

I watched as she pulled the diaper back up between my legs and taped it shut. Then with a look that looked like pity, she said, “Guess it’s another two months.”

She headed to the door and before opening it laughed and turned around, saying the one phrase I’ll never hear the same way ever again, “Happy Holidays baby.”

Fuck.