Slow Descent into Sissy-Hood... Ch. 02

I started pretty slow. I'd wear it for at first hours, then a day, and then finally overnight. That one had been the hardest, no pun intended. I would wake up multiple times a night, locked in sweet torture between the inevitably erotic thoughts in my head and the bittersweet tightness between my legs. The first time I'd tried it, I'd made it till 2 a.m. before finally unlocking the cursed, wonderful thing and bringing myself some sweet relief.

The post-orgasm afterglow was always strange. It left a lingering sense of guilt and regret that usually lasted a couple of minutes. But always and inevitably, my gaze fell on the small piece of steel, unable to deny myself from denying myself. It didn't really make much sense, but I didn't care. It felt incredible to be buoyed on that rising cloud of erotism for longer and longer periods of time, making myself giddy with lust. I never considered the long-term effects it was having, on my body or my mind.

About a month after my first encounter with 55JUMBO and his unexpected gift, I was comfortably wearing the cage for days on end. Some days, I'd lose myself in porn and fantasize about fucking the horny girls on my screen for hours on end. At other times, it kept my mind focused elsewhere; I couldn't get off, so I'd actually put more time into my schoolwork. My grades had even improved. One of my professors had emailed me, asking to 'please share your secret with the class!'. HA! Yeah right.

I'd also begun to enter the chat rooms as my alter-ego Sophie more and more. Things had begun to change here too; instead of just using it as an opportunity to connect with people and find the human contact I was so desperately missing, I was taking things...further. Whereas before, I had only replied to guys who put the work in, and pretended to be interested in me, I'd begun replying to... a lower grade of message. Especially if I was three days deep in chastity, I began to reply to messages which previously I'd have ignored or retorted against.

BIGMAN69: Hey baby girl, how would you like to suck this dick?

A message like that previously would have made me snort, take a sip of whiskey, and write back something mean. After three days of denial however...it just made me think of a girl taking a dick in my mouth...and how I would want her to reply...

SecretlySophie: Mmm, it's so big...but my mouth is so small...

And afterwards, maybe I would be disgusted at myself for a brief, small, meaningless moment, before the roiling tide of horniess took me up once more. And then the reply...

BIGMAN69: Take it between those ruby lips, slut, and moan for me.

...would cause my dick to strain in its cage in frustration. It wanted to be sucked.

SecretlySophie: Mmmmmm...fuck my mouth, Daddy, tell me I'm a good girl!

The cloud of sex mixed with ideas of girls on their knees, submitting, would descend on me, and in the absence of female company, I'd just work out what I wanted to happen to me, and act it out. My frustration would relieve itself through vicarious living; I wanted to be a slut for them like a wanted a slut for myself.

SecretlySophie: Cum in my mouth, I need you to make me a slut! Please Daddy!

BIGMAN69 has left the chat.

I knew exactly what to say, and I knew I'd succeeded when my chat partner disconnected suddenly, a sure-fire way to know that I had sexted them all the way to orgasm.

And it was addicting. I suddenly had a power, and a sexiness, which I had never known before. I'd sometimes work myself up for a couple of hours with porn while locked safely away, and then log on, hungry for some virtual dick to suck. Or rather, SecretlySophie did. I wasn't any part of it - I somehow disconnected myself from my male psyche, which was locked away presumably screaming in a box, as I sacrificed my manhood online to appease the goddess of my lust. I worshipped virtual cock after virtual cock with my virtual girlish mouth, each one pushing me further and further...until I finally unlocked myself and released, burning with regret and shame.

I was a straight male, for heaven's sake. What the fuck was wrong with me? Why did this turn me on so much, how could it make me say these things? Several times, I went to throw the device away before managing to stop myself at the last moment. I could stop anytime I wanted...as soon as I came I returned to my senses. It's a game I'm playing with myself. It's just lust, it's just porn, it's just a phase...every and any excuse came the rescue. I'm in control. And as long as I was in control, I was safe...

...which was a thought I was soon to regret. But it would inevitably make me put the cage back on.

I was deep into a session. I'd watched three girls take loads already in the four videos I'd watched, and I was searching for another. I'd only locked up the hour previously, but already I was squirming in my chair, the pressure from my crotch building, my useless locked-away dick helpless in the face of unyielding steel.

A chat message popped up on my second screen:

55JUMBO: Fancy seeing you again, sissy beta boi. Enjoying the cage?

I stared. Fuck. I'd managed to avoid my unwanted benefactor since they'd bought me the cage. I'd switched chat rooms, but I couldn't bear to part with my handle 'SecretlySophie'. FUCK. What was I supposed to do now? Play it cool I guess. And try to ignore the pulse of pleasure that came from my cage when I was called 'sissy beta boi'.

SecretlySophie: I threw that stupid thing away the moment it arrived. I don't know what you expected.

I leaned back, satisfied. That should show him! Now back to the-

*Ping* It was a screenshot. I felt my blood drain into my toes. It was a screenshot of an *extremely* steamy message session between SecretlySophie and a user called JETBLACK10. I'd asked him to call me a sissy whore, and he had obliged. I'd asked him to fuck me harder; he'd asked me to spread my sissy cheeks. I'd begged for his cum to make me a real girl; he'd disconnected.

55JUMBO: There's no need to lie to me sweet sissy baby. I know that cage must have opened you up to all kinds of new things.

SecretlySophie: ...look what do you want. This is just porn for me, not real. I did keep the cage, but I don't wear it all the time, and all I've done is go in chat rooms like before. Nbd.

I sat back in my chair, sweating and cursing to myself. Part of the reason I was trying to avoid him is that I hated how right he had been about the cage. How much I was enjoying the denial and lust. I didn't want him to gloat. I didn't want to admit to him, and therefore to an extent myself, how much I loved every moment. Every moment of sweet torture, of denial, of submission, of frustration. Of watching other dicks be sucked or fucked, knowing that mine never had, and that it was incapable of it right now. Of submitting to another dick simply because I couldn't use my own.

55JUMBO: Okay, okay... fine. Look I understand, and I'll level with you. I'm just curious about how long you can wear the cage. A guy with a porn addiction like you probably lasts an hour? Two?

My heart rate slowed. He called me a guy. I stared at the screen. No pulses from my crotch, no jolts of erotic energy. In fact that opposite - this had really disrupted my mojo. A faint hint of pride slid it's way across my brain and into my fingers before I could even react.

SecretlySophie: Actually, my record is 4 days.

Oh fuck. Why did I say that?! It was true, I had lasted four days and change the last time I'd worn the cage before tonight. But why did I tell him? The faint hint of pride grew stronger. The cage had focused my academic energy somewhat. It was difficult to prevent myself from trying to pull it off in class on Day 3 and try to fuck every girl in the room. It was tough to get home and do homework, rather than just knock one out. But I had resisted, in the sure knowledge that the payoff would be even better.

So let that show him.

I didn't realise it though, but I was quicksand and sinking fast. In the cold light of day, there's no way I'd have even entertained talking to 55JUMBO again, let alone telling him how long I could last in self-imposed chastity. But that's the thing about chastity: the cold light of day only comes when you cum, and sometimes that can be a very, very, long time.

And bad things can happen in that time. And even though I'd only been locked up for a couple of hours, the tendrils of lust were already ensnaring my thinking.

55JUMBO: Oh shit, wow!! That's amazing...if it's true.

55JUMBO: If you can prove it, I'll send you $$$. You already know I'm good for it.

SecretlySophie: How the hell am I supposed to prove it?

55JUMBO: Use the numbered tags.

I glanced across at the small bag that the cage had arrived in. I'd seen the numbered tags when I'd first opened it up, but I had no idea what they were - each one was a small plastic one-use padlock, printed with a different number. I'd just assumed they were replacements if the cage broke.

But now I realised what they were for. Once you had clipped the padlock in, it wouldn't come unstuck - you had to snip it with scissors. I'd already used up one this way when I'd first been sent the cage, just out of curiosity. But I had five left...

I should have stopped. I should have closed the chat. But my cage was already strained with the idea that I would have to be locked up for a week, and I'd be accountable to someone else. I absentmindedly rubbed my legs together, causing the cage to rub a little.

SecretlySophie: ...how much $$$?

*****************************************************

I stared at the phone, my thoughts swimming. What did my masculinity mean to me?

I'd made it all seven days - seven days in a pink haze, seven days of no satisfaction, seven days of sleepless nights filled with naked, dancing dreams... Seven days in chastity. My body was aching for release. Any underwear I put on was soaked in minutes; I got wet like girls got wet. Any mention of sex or pussy or girls or even the word penis at this point got me leaking like a slut almost instantly.

My porn use had escalated too. I was watching the gamut - shemales, trans...I'd even started searching for sissy videos. Nothing made my heart beat faster or my attempts at cumming more frantic than those videos. I'd seen sissy hypno when I'd been uncaged, and it had never interested me. I'd wanted to do the fucking, I wasn't the object of desire: the girl with a dick on screen was. But now...it's like the had a direct line to my cage. The videos scared me, and more than once I found myself hyperventilating and closing the window hastily. I didn't want to dress up, I didn't want to lock myself up, I didn't want to submit...I just wanted the money. That's what I told myself, anyway. In truth, nothing made my cage leak more than being told I was a girl, I deserved to be locked up, I existed to please real men...

Psychological games aside, it had been worth it financially. 55JUMBO had been true to his word - he'd sent $25 worth of bitcoin to me almost instantly after I sent each picture of my locked up cock. Day two and day three as well. The money always came quick - the longest I had to wait was 10 minutes. And it was easy - Snapchat filter with the date and time, pull my pants down, send it off. Bing - instant money.

I feel like I should explain at this point - I really, really needed the money. My bank account had been lean for months, and I'd been 50$ off not being able to make my rent this month. I'd stupidly spent the stipend my parents gave me on whiskey, and drank it away like an idiot. It didn't make it less humiliating (and arousing, which I would admit to no one) when I took the picture each time, but it did ease the sting. Not only did I have enough for the month's rent, but I'd paid some friends back and bought some whiskey.

And I was so happy with my new financial situation - and, let's face it, horny as hell - when he messaged me on the sixth day, after I'd sent him my daily picture.

55JUMBO: You're impressive sissy, I'll grant you that. Let's see if we can up the ante a little.

He'd reverted from calling me 'guy' to 'sissy' on day four. I didn't correct him then - and I wasn't correcting him now. I don't know why. I'd downloaded an app on my phone so it was easier to send him the pictures. For some reason though, this made things seem more real. It was one thing to sit down at my desk at 3am messaging a random guy; it was something completely different to text one at 2pm like I was someone's girl. A shiver ran through me.

SecretlySophie: ...what do you have in mind?

55JUMBO: In your next picture, I want you shaved and in panties.

My eyes roved over the text. For some reason, I was actually considering it. My cage felt hot, as did my cheeks. Shaved and in panties? It was one thing to wear a cage, it was another to wear panties...right? I didn't even know where to get hold of panties. Ordering online was out, because the picture was due tomorrow. Maybe if I...

I sat back on the bed, eyes on the ceiling. Why was I even considering this? I shook myself slightly, a wet dog shiver running through me. Why couldn't I get my thoughts straight? My mind was a whirlwind, not helped by the erotic sensation of not being able to get hard. Why was my cock trying to get hard in it's prison?

I heard my phone go ping. I sat up to look at my phone, driven by the lust coursing through me, unable to control the rollercoaster.

55JUMBO: I'll double your rate to a flat $50 if you shave your legs and your clitty, and find a pair of panties to wear. $75 for if they're lace. $150 for lace panties, smooth legs, fishnets - and a landing strip.

55JUMBO: And of course, the cage stays on, good girl.

55JUMBO: Add the fishnets and panties to your wishlist, and you'll get them by tomorrow. Or you can go shopping...your choice.

My mind raced. I sunk back down, and stared without looking. What did my masculinity mean to me? Or more specifically, how much was it worth? I loved wearing the cage to elongate my pleasure. Even though I'd hadn't cum or even had an erection in days, I relished the denial, knowing the promise of the greater pleasure at the end. And so, it was a win for both myself and the man at the other end when he paid me for it; I was in dire financial straits after all.

Yeah, after six days in chastity, I was enjoying sissy hypno, rather than just vanilla guy on trans/shemale/crossdresser porn. But that was porn: it's one thing to be told you want to buy panties, than actually buy and wear them. It wasn't real.

But this? This seemed like too real. I was a guy; I am a guy. Why had he called my cock a clitty? Even the thought of the way he spoke to me sent another tremble of pleasure up my spine, straight from the pressure I felt in the cage. I'd heard the term in sissy hypno, I knew what it meant. Girls have clitties. Despite my lack of knowledge of the female body, from both my pornographic inclinations and deficit of experience, I knew that. It was a nub above the vagina, a pleasure centre to be teased and rubbed. Another wave of pleasure. Was that all mine was now? I don't know why he had said that; there's no way he knew about the sissy hypno, right?

The money though. This would all be over tomorrow, one way or another, and $150 would go a long way towards whiskey and food. Or I could save it; I was an economics major after all, and I could always use more bitcoin. But to get the full $150...

...the panties were fine. Even the fishnets didn't have me that worried. But shaving my legs and my crotch felt like...stripping away a sliver of my masculinity. It would take a while to grow back, and until it did, it would remind me...

Of what I did for $150. $150! That's a lot of money! Sure I had to convert the bitcoin to pounds before it would spend here, but that was no hardship anymore.

So, there was the money on one side. My pride on the other. And in the middle...in the middle was my caged libido. It raged through my body like fire, like a girl on the prowl, like a bitch in heat, like a slut being railed, like an unstoppable force of horniness. The caged energy bounced around my body and my mind. It was the energy that made me sext in chat rooms pretending to be a girl, taking virtual cock after virtual cock into my virtual body. It was the lust that made me want to feminise myself, to find something more real to pleasure, to take a hard and straining erection between my plump red lips. To bat my eyelashes and smile as I knelt before something that could get hard, that I could worship, while my own was imprisoned. To take something into myself, to be soft and sexy, to be alluring and feminine...

I needed to cum. I sat up on the bed. I needed to cum or I was going to go crazy or do something I would regret. The sensation of denial and frustration was so intense that I was daydreaming about sucking cock! How the fuck had this happened?!

I leapt up, crossed my small room in one bound, and took a cold shower. I made a decision while the freezing water tumbled down onto my shoulders.

I sat down at my computer, and started looking at black lace panties.