My First Solo Sissy Night...

The following short story is loosely based on a true experience. All characters are above the age of 18 years old. There is also self bondage depicted - do not try/not meant to be repeated. I will admit, I had to have my cage on get through writing this story.

A big draw to sharing it is for feedback - so please leave a comment and/or rating if you have any thoughts on this experience.

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Oh the internet. I wonder how many people have gone through some sort of self-discovery to due random internet message boards. I was a recently single guy having gotten out of a long term relationship. Not a big dude by any means, 5'7'', 135 lbs. You see, I was relatively slim from long distance running and never very masculine to begin with. Never bothered me before though as I had okay success with the ladies until just recently.

Anyway, I was a relatively vanilla person who happened to like bondage. Did some basic tie-up games with my ex, but nothing serious. And of course I'd never let her tie me up. On some of the more horny message boards, I came across more bondage scenes and learned about the kink a bit more. From here, it was only a hop skip away from seeing guys tied up, not my thing. Then all of a sudden there was this individual in a super obnoxious pink outfit, fuzzy material, pink all around, so over the top it was hard to imagine any woman wanting to wear it. Sure, paid for a porno shoot is different, but you get my point. You can imagine my surprise when it was revealed when the panties came down that it was quite the emasculated guy wearing some sort of cage on his cock and balls. That was the first time I discovered being a sissy was a thing.

And that was also the first time I discovered chastity cages. Sure, I've heard of chastity belts and thought about clunky metal things from the medieval times that I couldn't believe were real, but this was different. I also couldn't get over how it was a guy. Granted it didn't show his face, but it became obvious and then finally reading the post it was linked to.

From here, you can say sort of this exploration further into the kink rabbit hole started. I wanted to take charge of one of these so called sissies. Learning about the submissive aspect often associated with it. It just seemed so silly, and like good ole plain bullying with all parties consenting. I tried my best on the message boards, but was finding I wasn't assertive enough and really no sissies were taking me seriously. I told myself it was a fluke, but I myself was getting restless. You know when you have a bad idea and you're set on it, you can sort of justify it anyway and not think clearly about what you're doing?

Well that's sort of what I ran into. I thought why don't I see what it's like to be sissified. No one would know, and then it'd be like I was doing it to someone even though that someone...that someone would be me. It wasn't totally solo, I figured why not use the internet for help. In my quest for hunting my own sissy, I came across a dominant figure who let me vent about my troubles catching a sissy. So when I put this idea by him, he totally supported it. Which made it that much worse adding fuel to the fire for this idea of mine. So with his help, I put together quite an online shopping cart.

I wanted to make sure this kinky night planned wouldn't be some beginner stuff. My shopping cart held 2 sets of pink fuzzy lined bondage cuffs, a small pink chastity cage, a pink bondage hood with a detachable blindfold and a detachable pink penis gag. The hood could lock around the blindfold, the gag, the collar, and would be laced underneath the 3 straps. Now I should have stopped here. The pink color was bad enough, but could argue just exploring a bondage kink. But I was all in, and the emasculation needed to be complete. As my online helper agreed, a sissy outfit needed to be part of this.

So added to the cart was quite the new outfit. It included pink fuzzy over the knee socks with white polka dots on them, actually came in a 2 pack and a piece of clothing that was absolutely absurd. It was a onesie/bodysuit with snaps under the crotch. It was white with pink outlines around the sleeves and leg holes, plus across the chest it says "I <3 daddy" in pink. It was tough enough to even look at on the screen. At this point figure I had everything, but my online helper again made the case that there was a way to fully complete this process.

It was an innocent enough question. "What about a butt plug?" I had never done anal before. I didn't think it was fair that I'd be stuffed before I got to stuff someone else's butt. He made the good point that I'd be so restless caged, it would provide some pleasure and relief. No point in thinking about it from a humiliation standpoint. He showed me ones that were properly sized that wouldn't hurt, and some with Bluetooth capabilities to be controlled via a smartphone and by anyone with permission to. As someone into cool tech, it was a neat concept. What could be so bad? Plus other guys did butt stuff that weren't into the sissy stuff. In order to do it right he reminded me, I needed ample and the right kind of lube. So I then had a Bluetooth controlled plug, fake cum lube (he said it was the best kind, I don't know why I didn't pick a different kind!), and a lube shooter after he explained it's the easiest no mess way to make sure things don't hurt and slide up there okay. Oh how little I actually knew.

I couldn't believe I finally pressed check out, and these things were on their way to my apartment. To say I was nervous was an understatement, but I tried to distract myself. They were coming in on a Friday, so my Friday night was going to be interesting to say the least. My online bud made the good point that my pubic area needed to be shave, you know, so the cage would "work better." Still, I agreed it made sense cosmetically. The only other preparation I did in advance was having a 2 gallon jug filled with water halfway already frozen in my freezer. This will make sense in a little.

Finally, it was the Friday everything came. This guy had been helpful enough to give good feedback, I thought I'd keep him in the loop with what was going on. I sent him a photo of the bunch of boxes and envelopes I had waiting at the door of my apartment. I got to work unpacking and discarding all the track. Oh my goodness, the absurdity of these items all together. First came the bondage gear. The cuffs were perfect. Strong, sturdy fake leather in a pink cover lined with this soft fuzzyness. I got chills placing one on my wrist just to see. They could be clasped together with a little chain between and came with padlocks too to up the difficulty level if desired. The pink bondage hood was very intimidating! It looked so isolating. The penis gag wasn't super long, but definitely noticeable and clearly plugged the little mouth hole available. And then the blindfold did it's thing strapping across the eye holes. I wouldn't need these till last.

In order to not lose momentum, I had to get the chastity cage on asap. I was so tempted just to jerk off then and there and be done with this stuff. Did I really want to wear all this and do it? Enough said, I pulled down my pants and well, would it shock you I wore tighty whiteys? Just as I had read about, slipped one ball at a time through the ring follow by my cock. The ring was snug, but not uncomfortable. I then slipped the tube on over my cock connecting it to the ring. I added the key to turn the integrated lock, and just like that I was locked up. The whole thing was snug and was the first pink addition for the night. I'm not big down there, so I started with a small cage to begin with, and oh boy did I feel emasculated. My buddy online told me this is where the fun would start. With the antsyness, hornyness, and weakness driving me, I took the chastity cage and all the padlock keys to the 2 gallon jug of water. I dropped them into the jug and they landed in the middle on top of the ice that was already there. I filled it the rest of the way with water and had some time to kill.

My online bud made the point that it was winter time, and to truly experience the material of the bondage gear and outfit I bought, I had to shave everything below my eyebrows. Like I said earlier, my pubic area was already shaved, but this seemed like a big step to me. I didn't want to. He made the case though: it was winter, no one would know, stuff would grow back super fast, what more did I have to worry about. Reluctantly, or maybe not, I gave in. Plus I had time to kill as the jug was still freezing. I spent the next hour in the bathroom shaving what little body hair I had from my legs, chest, even my arms! Now it was go time.

At this point it seemed silly having to message him back and forth as I was trying to prep stuff. He suggested me putting ear buds in and just taking a call. This was some guy 10 years older than me from across the country. He didn't know me, so there was no risk. I agreed. Even just by his voice I could tell he was older and bigger than me. That said, he was nice enough plus calm, cool, and collected which is what I needed at that moment. It was time for the butt stuff. The scope of what I was doing hadn't yet hit me. Being fully smooth was unique, but I was more so naked and this just felt like he was helping me jerk off. Of course I was caged and there was no jerking, but the equivalent was me being plugged so I was sort of tricked without knowing it! The lube shooter is such a clever design. Plus it being smaller, was perfect for the initial stretching of my hole. Similar to the size of a finger, I worked it in and out a few times with it coated in the fake cum lube. This went on for about 5 mins and the guy in my ear did a good job distracting me and normalizing what was happening even as I was stretched in my cage. It was then time to squeeze the lube shooter to squirt some fake cum up my butt. It's crazy to read that sentence back now and think about it happening the first time. I actually squealed a little.

As can't have too little lube, more was squirted up in me and he began to make some jokes alluding to me being leaking cum soon. Better get that plug in there! In went the bluetooth plug. It took a little pushing and relaxing, but it wasn't too bad, and I could feel my butt swallow around it's stem and the T bar remaining outside, but tucked nicely with my butt cheeks and not uncomfortable. At this point it was a little chilly, and almost like he planned it that way so I was thankful it was time to put on some clothes. Of course I would have preferred gym shorts, but that's not what this night was about. The onesie had snaps under the crotch, so it could pull over like a t-shirt. Then I pulled the backside underneath me and clicked the 3 snaps together. It was absurd. In this onesie bodysuit, my smooth legs and arms sticking out, a form fitting design with its pink outline and bright across the chest the text of "I <3 daddy". The material was way more soft than I wanted to admit, and I could feel it hugging my upper body and keeping everything snug including my caged cock and plugged butt. Next came the fuzzy over the knee pink polka dotted socks that also happened to match. They were so soft, and once on and pulled up high, I couldn't help but wiggle my toes in them.

My internet bud, now my phone bud, told me to look in the mirror. At this point I had only looked down at myself, so it wasn't the same effect. Looking in the mirror I was shocked and never felt smaller in my life. There, clear as day, was a sissy in his long pink fuzzy socks and a bodysuit onesie telegraphing to the world he loved daddy. Even worse was the little outline of the nub cage that could be seen. I was a sissy. It wasn't too late to change this. He told me not to worry about it, no one would know or see. So on I went now attaching the individual cuff to each ankle and wrist of mine, the pink now matching. This is where things got stupid and dangerous.

He told me to get the 2 gallon jug with all my keys frozen in the middle of it and bring it out to the bedroom. Placed it beside my bed in a large storage tote. Didn't want water to spill on the floor once it melted. This is when he sprung the first surprise on me. Since I was going to be bound, I wouldn't be able control the vibrations of the butt plug nestled safely in my tush via the app on my phone. Low and behold this tech allowed me to share him a link giving him control of my plug. I was nervous, but he said he wouldn't turn it on right away and it'd be okay. At this point I had tunnel vision. I was so shocked with what was happening. It was like I was slipping further and further down this sissy rabbit hole.

With him in control of the plug, I got on my bed. Ankles were next to get cuff together. Next came the hood. It took a little to get it laced all the way down the back of it, but it was snug. I could barely see from the eye holes and the mouth hole was still open at this point. Click went the lock around the collar in essence locking the hood on my face. Where was the key? Suspended in the middle of the 5 gallon jug with the other keys including for my chastity cage and the other padlocks. One of those padlocks already locked my ankles together and another now at the bottom of the hood. 3 more to go, the gag, the blindfold, and my wrists.

With the hood on, next came the penis gag. I had never had anything remotely phallic like in my mouth before. And when this went in, I wouldn't be able to talk to my phone friend. He wasn't concerned. As he told me calmly in my ear, this is all part of what we had planned. In went the gag. Thankfully I didn't gag on the penis gag, but it was in enough that I couldn't help but suck it and run my tongue around it. And just like that it was also locked on. Now I had the two padlocks left out and ready. It took a bit, but managed to get the blindfold in place and locked on, totally isolating me in the hood. Both deaf and blind except for what I could hear from my bud via the earbuds in my ear. While blind, I worked my wrists in front of me and clicked the padlock in placing locking my wrists together in their cuffs and laid back.

There was a second pause where I couldn't tell anything. I felt smothered in pink, stuck, helpless, and a sissy. I could roll off the bed, but didn't want to spend the time off the bed. I knew I had to be careful to eventually go to the jug containing my keys once I was frozen. It hit me that I was stuck like this for the time being. At the same time it hit me, maybe 5 mins into just taking it all in, the butt plug tucked away inside my butt vibrated at full speed and I heard my online bud laughing in my ear. "You're a sissy, my sissy, and I'm the daddy you heart tonight and moving forward..."

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