A Sissy Diary

Quick note: I'll be updating this with more parts, but this is my first attempt at smut. Hopefully you enjoy reading as much as I did writing :)

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I'd discovered the concept of being a sissy fairly early on. My first real attempt at anything was when I was 18, using a marker to inadvertently give myself my first, hands free sissygasm. After that, I was hooked. I'd acquired a set of lingerie in secret, growing my hair out and losing enough weight to accentuate my naturally wide hips. I also started to write a little smut blog, more for myself than anyone, with no expectations of followers. It was essentially a progress tracker, where I would record how I felt about my habits, how excited I was for my first dildo to arrive, what position felt best and how exhausting but incredible oral practice felt. With each bigger dildo and better quality photo, I saw incremental growth in my followers, soon having close to 100 people following me, leaving comments ranging from the expected horny comments to others offering money if I 'helped them out.' I wasn't interested, of course, but the prospect of having extra money was quite nice, so I made a post asking if people would like to donate in exchange for seeing me use the funds for certain outfits or toys. The response was overwhelmingly positive, so I set up some small goals, never accepting more than what would be enough to make said purchases as I never wanted the viewers to expect anything more in return, and in exchange posted pictures, both actively playing with myself and merely showing off the outfits. My face was, of course, always masked, and I made sure to never feature anything that could reveal my identity.

One day, a viewer made a suggestion regarding chastity cages, and while I had heard of them, I never thought of using one, since it felt good to play with both my front and back. But the viewer told me how hot it would be if I learned to "cum properly, like a woman." Something about the wording resonated with me, and soon I had purchased one. The results were incredible. I had never felt so horny, but even more than that, the fantasy of being unable to touch my cock, which slowly became my 'clitty' thanks to my viewers complimenting it, was ridiculously hot. At some point, I stopped thinking about women and began to fantasize about being ravaged by a meaty cock, letting it pound me to completion, never letting me touch my clit to make sure I had cum correctly, turning me into a proper slut.

Not too long after that, I also realised my interest in exhibitionism, as being naked in public had some inexplicable charm. Not just that, but wearing clothes that were explicitly for being fucked, not to function as clothes (such as bottomless panties or lingerie) had me fantasizing for days on end. It wasn't something I was ever able to properly fulfill with a real cock, though I did come close one winter, managing to bring a lubed dildo outside, wearing nothing but thighhighs and a garter belt with a coat on top, riding a dildo on an apartment balcony leading to a stairwell, from where anyone could come and find me. The thrill of potentially being found had me beyond horny. The only thing that stopped me was the sound of footsteps coming up the stairs, though I made sure to ride for as long as possible before quickly running, leaving a puddle of lube amidst the snow that the person might have found if they had entered that floor. I didn't manage to cum, though the experience had me on a high for a week.

It was in my second year of University that I'd discovered a room which was effectively never in use. I'd watched observed it for weeks before finally slipping in on a Friday, after all my lectures had ended, to enjoy some alone time. While it hadn't come to mind yet, I had long since fantasised of being able to experience something like fun in a public room, but was too scared of being discovered. Compared to the balcony, the room had too much frequent traffic as students passed by between lectures. My favorite fantasy was being able to explore a campus in a full set of lingerie with bottomless panties, a chastity cage and most importantly, a collar and maybe even handcuffs. Not for petplay or anything of the sort, but to ensure that I couldn't run away of my own accord. The lack of control that that entailed turned me on more than anything I could hope to imagine. As for who would lead me, well, that didn't really matter.

As no-one ever entered, I soon realised I could REALLY have some fun here. I snuck my sissy lingerie and toys into the room and, thanks to a storage closet I found in the back, I now had everything I wanted to train myself in my little hobby. I even ended up storing the key to my flat metal chastity cage in the closet so that I wouldn't be tempted to unlock myself over the weekends outside of uni. I obviously didn't have the self control to leave it there consistently though, and would occasionally take it with me, releasing and feeling both shame and regret thanks to losing the thrill of chastity. Still, no matter what I had brought with me, actually committing to it was an entirely different situation.

The door to the room only locked from the outside so I was shaking the first time I actually tried dressing up there. The fear of being discovered turned into exhilaration as I closed the door with a click, knowing that just a turn of the handle stopped someone walking by from noticing me. The fear turned into exhilaration, each set of footsteps that passed by making me both scared and horny, as I finally came again, entirely hands free, left shaking in a puddle of my own cum.

It slowly became a habit, with me even posting some pictures from said room. Though I stayed careful with what I revealed so that it couldn't be traced back to me. Or so I had thought.

It was just a regular monday, midway through lectures, when I had a free slot. I'd prepped myself before even coming to uni, so I was ready to go as soon as I entered the room. I closed the door behind me and changed. The silky lingerie, tight straps and soft negligee had me feeling hot and heavy even before reaching for the dildo. I had worked my way up to a 6 inch behemoth, by my standards, and sat down to start lubing it up.

"Heya," a husky voice suddenly said.

My head whipped around, my hands doing their best to conceal the dildo I had just meticulously prepared out of view. Still, he saw what I was wearing and we both knew there was no explanation for that. Besides the obvious. I felt an adrenaline rush as both my heart and thoughts began to race. It was over. I knew the risks, but I didn't really think it could happen. Who was he? I didn't recognise him but he was obviously a fellow student. Worst of all, I noticed that he seemed to be holding his phone as though he'd just taken a photo. My life was over. But wouldn't I have noticed the footsteps? How did he even get in here so quietly? I continued to sit, frozen in fear as he put his phone on a desk nearby. Closing the door behind him, he pushed a desk over towards the door to prevent it from being opened and took a seat in a nearby chair. AS much as I hated to admit it, even with the awful situation I was in, my clitty was straining harder against its cage than ever before.

"You must be thinking a million things right now. But before all else, let me introduce myself. My name's irrelevant, since you'll be calling me daddy from now on. But to be honest, I'm a big fan. I had been into slutty little sissies like yourself for a long time now, and following your little blog for just as long has been quite fun."

Shit. But how could he possibly know that it was me? "Judging by your expression, looks like I'm right on the mark. Commendable progress, by the way, since you look better than most of the girls do in our year. When you're dolled up anyway. Hiding that pretty face behind a mask in all your posts is a real shame you know. I'm sure all of your followers would love nothing more than to tear it off and have their way with you."

I felt a scowl form on my face as he kept talking. "Are you serious? What are you even here for then, just to gloat that you caught me?"

His smile widened as did my eyes, realising what I'd just implied. "Hah, looks like you had some expectations. Can't say I'm surprised, seeing what you write about, but knowing just how unreasonably horny you are even in this situation might make this more fun." He unlocked his phone again, this time turning it towards me. "As you can see, I'm ready to email your photos to myself. All I need to do is click send. No matter what you did after that, I would still have them. And we both know what that means right?" He said, rubbing it in. "Now, as I said, I've been your fan for a while. And while I've got my own desires, I didn't come here to ruin your life. I wouldn't get any more content then would I? I've come here to offer you a fun little opportunity, if you will."

I felt a mix of distrust, curiosity and strangest of all, disappointment. The fact that he wasn't here to blackmail me was relieving, but I still didn't completely believe him. What did he gain out of this then? "To answer what you're thinking, I always wanted to own a sissy. But not through blackmail. I wanted to own a sissy that wanted it, and wanted me to own her. And while I know you're quite depraved, I also know you're a virgin. Most people aren't as desperate in keeping up a blog like that, fantasizing without end but never really going any further. Am i wrong?"

I felt even more exposed. I can't have been that obvious right?

"Ok asshole, fine, I am a virgin. But what makes you think I'd be interested in you?"

"I think you're forgetting what position you're in right now. If you're going to be giving me that much attitude, I might just send the photos to myself right now."

Fuck. "I'm sorry. Please don't"

"That's better, Now, as to my proposal. I want to offer you a way to explore your sissy side. You're already well on your way but as you can see, you aren't very good at doing it carefully." I couldn't deny that. "But I also know that you're very unlikely to trust some random guy who appeared while threatening you. So here's the idea. If you wish to, and only if you do, you'll submit to me in increments. I'll be taking your keys too, of course. I know you love the idea, and I will only be letting you cum like a proper girl."

What the fuck does he mean by increments? My legs were getting tired from sitting still, and while I didn't like him, he seemed genuine enough in the way he talked. So i turned to face him, placing the dildo next to me as I heard him out.

"Impressive size. Though I think you'll like mine more," he continued with a laugh as I felt my cheeks flush. It's not like there was a point in hiding it anyway.

"Regardless, what i mean by increments is that you'll get a chance to be rid of me. Think of it as a safeguard. If I want you to trust me, I gotta give you a reason right?" That sounded too good to be true. My clit was leaking as I realised just what his proposal meant. Living out my fantasies, with safety? I could feel myself falling for it, hook-line-and-siinker.

"You're... serious aren't you? What's the catch though?"

"Good to know you're not THAT gullible. The 'catch,' though I think you'll like it, is that if you agree, I take some photos. Not just some shitty low res photo, but a proper, identifying photo with blackmail potential. After all, how can I push your limits if you don't know I'm being serious?" My stomach dropped. I know the photos he must have taken could still be denied. Yes, it's here at school but I could easily pretend to not know what he's talking about. Besides my hair, noone suspects what my hobbies really are. On the other hand though...

"But you just said I could get out if I wanted to."

"Oh you definitely can. What I mean is that every time an increment passes, I'll give you a chance to delete everything yourself. I won't interfere, and if you so choose, we cut ties. I'll pretend I don't even know you. Don't expect me to quit looking at your blog though."

".. And how do I know you're not lying?"

"Like this," he said, opening his gallery, and deleting the images he had, even going into the recycling bin to completely wipe them off his phone. He handed it to me to check, and I did. He really wasn't lying.

"If you really want me gone, I'll leave right now. Though I'd recommend you to close the door next time. Someone else could find you and that wouldn't turn out as well for you." I thought about it. Well, at this point, there wasn't much to even consider. My fantasy was coming true.

".. and if I don't?" He smirked again, taking his phone from me as he got up, "Then you'll begin by calling me by what a slut like you should call me."

"Okay... Daddy."

"Good slut. Before we continue, Let me explain a little more. The intervals I have planned go like this: 1 day, 3 days, a week, a month, 6 months, then a year. If you're in after that, then let's just say the duration probably wont matter to you anymore."

Wow. That sounded like some conditioning bullshit. I knew I was into being a sissy but I knew I liked my everyday life just as much. And what even is that jump? a month to 6 months? that sounded insane! Noone in their right mind would agree to that.

"If you're worried about the increments, don't be. I don't think you'll be against it once you're in deep. And I won't force you to crossdress in everyday life. If you wan't to, that's completely down to you."

"But you're not lying to me right?"

" 'Right' what?"

"... right daddy?"

"Of course not. But I won't go easy on you if you agree to this. We both know what your fantasize about. And I know exactly what a whore like you wants. So what do you say then? How's a day to try it out sound to you?"

I didn't know. This sounded too good to be true. Even with him deleting the photo and all, I couldn't guarantee that he wasn't going to go back on his word. But I wanted to trust him. If he was going to deliver on his promise and I rejected it... I think I'd spend the rest of my life regretting it.

"Since you look like you're still worried, I'll give you some time to think. I'm going to go get a little peace offering and while I do, you can think it over. But if I come back in 5 minutes and you haven't decided then I'll be leaving. I don't need a sissy who doesn't have some faith in her sluttiness."

And with that, he picked up his phone and left. I was stunned. I got up, cleaning the dildo up and putting it away in the cupboard. I sat down on a cushion I brought in before, still aware of the buttplug sitting snug inside me. I put on my jacket, covering enough so that if someone else walked in, I could probably give them a cover story. Every second felt like hours. If i'm wrong then my life very well could be over as I know it now. I know he probably wouldn't just post my picture anywhere, since revenge porn is illegal, but I'm sure someone this determined would either not care or post it somewhere that it couldn't be traced back to him.

Suddenly, the door opened again. He walked in, hiding something behind his back, promptly putting something in a nearby drawer before turning towards me with the other package. I slowly dropped my jacket as I got up and sat down in front of him, my knees together as I looked up at him expectantly.

"Now that's a good sissy. No need to even ask what you decided then huh?" I felt a twinge of humiliation as he said that, but let myself enjoy the sensation of submission.

"Since you're such a good girl, I won't keep you waiting. This-" he opened the small package, revealing a golden cage, " is a little creation of my own. I know you've got a cage on, but based on your most recent pictures, I tailor made one to fit. I'm glad you didn't let the opportunity go to waste. But you know what that means right?" I felt anxiety and excitement stirring as I understood what he meant. "Since you agreed, you're going to let me put this on you. And I'll be keeping both keys."

I felt my heart begin to race again. This wouldn't just be a commitment. I loved the fantasy but I also didn't know what I'd do if something went wrong. What if i had an emergency? It'd be foolish to let him do this... but I was already hooked.

"Now sit on this table. I'll get your keys." He walked over to the cupboard and opened it up, picking up the keys immediately. So he had known about this room for a while. I'm such an idiot. For the first time in a long time, I thought about the cage I had on. It was comfortable, sure, but I felt secure in knowing I always had a spare at home. I kept it locked in a box that requires a 10 minute wait to open, so I would almost always stop before taking it off, but even then, I would occasionally get too horny to stop, and then always regret it. But in case of an emergency, I had it. But what now?

He arrived, kneeling down in front of me as I noted how muscular he was. He spread my legs open with a careful yet forceful push as I covered my breasts. I'd long since grown self conscious of them since I had played with them so much that they'd actually developed a little.

"Do you blacksmith daddy?"

"Good guess. It's more of a hobby than anything, but that's where I made your cage," he finished, taking my metallic cage off. He grasped my hand as I complied, and he put a key to the new cage in my hand. He began to put the new cage on, maneuvering it over my erect clitty as I struggled to stay still, my breath growing more shallow. I couldn't believe how turned on I was. Nor that I was letting him do this. The flat head felt unyielding as he pushed it down. With a little click, I could feel it secure in place, but he still pushed in the locking mechanism afterwards. Finally, he took a leather strap on and wrapped it around my waist before attaching it to the belt at the sides, securing it into the locking mechanism. "So that you don't get any ideas," he told me, smiling.

"Now lock it."

"Me?"

"Yes, slut, you. If you want to prove your worth, you're going to give me the key. Hand it over and show that you are submitting to me wholly and completely."

Fuck. He had a way with words. And I had to admit that the cage was professionally made. I felt my clitty straining against the new cage, but no discomfort. It felt as though my clit was being carefully caressed, yet still restricted. The cool metal was now beginning to warm up to my body temperature, and as it did I could barely even notice its presence. I took a deep breath and locked it. I noticed how deep-set the locking mechanism was inside the metal, at an angle that would be close to impossible to pick by myself should I try.

"It's made of a metal that would be quite hard to break with anything short of a buzzsaw. I'm sure you realise that this is a commitment. But I know you want this. So hurry up."

I hated that he was right. With shaky hands, I locked the cage and, breathing heavily, finally gave him the key.

He pocketed it and smiled, "doesn't that feel good? Completely submitting? You're well on your way to being a proper slut."

I couldn't believe how excited I was to hear those words. It felt like his praise alone could make me cum. In fact, it took everything I had just to keep sitting, my posture already wavering in anticipation.

"But that's not quite what you want, isn't that right?" His expression shifted, his smile turning more cruel. I froze, my hands on my lap as I stared up at him. "Since you've agreed to this, let's show you what to expect," he proceeded to unbuckle his waistband, where his erection was already half-stiff, pushing upwards.

I couldn't believe it as he pulled it out. It had to be at least 7 inches long and girthier than the dildo I normally used. I couldn't resist reaching for it, before he slapped my hand away.