Slow Descent into Sissy-Hood... Ch. 01

Beta boy beginnings.

It started when I was online, lonely and drunk.

I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that without the fear of discovery by roommates, I spent an increasing amount of time browsing pornsites and adult chatrooms. And so, instead of slaving away on coursework, I was idly clicking my way through gigabytes of porn, most of it earmarked Shemale slut takes two cocks at once or horny trans teen sucks and fucks.

I'd had an obsession with trans (or in the original dark days of the internet, shemale/tranny) porn since I was 13 years old and had my first computer. Back then, it was usually the odd hentai/futa image that cropped up on 4chan or long-forgotten image based sites that interested me. I didn't really question it - but as I had grown, my porn taste had shifted from the occasional trap or trans scene, to exclusive. I could not cum unless the feminine object of desire on screen had a dick - I didn't know why.

A ding from my computer caught my attention. I clicked away from a video in which the gorgeous gurl on screen was taking it from both sides while her cock swung around, and saw that I had been messaged on one of the chatrooms I had left open:

55JUMBO:

Hey baby, you part time or full time? ASL?

I snorted dismissively and took a swig of my whiskey. I wasn't either, I thought myself, I'm just a pretend girl. Call me crazy, but try it first - pretending to be a girl in a chatroom is fantastic. People just want to talk to you! Most have put real effort into their pick-up lines - they want to know your interests, your personality. For a loner in a bedsit, it was a great way to get some human contact. And then, there were people like this guy. I decided to get rid of him, using the line that usually sends men offline in an instant:

SecretlySophie:

Look dude, I'm just a guy pretending to be girl. I'm a 23 year old MAN in Birmingham, UK.

I leaned back and took another swig. That will teach him to put some effort into his opening lines! I switched the tabs back to the girl (who was now happily jerking herself off while she was being double-teamed) only to hear the *ding* again. Frustrated with this basic Chad, I switched back to give him a piece of my mind:

55JUMBO:

Haha there's no way someone pretending to be a girl online is a guy. You should one of these out, you might like it:

[Link to a chastity device on Amazon]

I stared at the screen - what the hell was that!? After a few seconds, I realised I had seen it before and knew exactly what it was - a chastity cage! Who the hell was this guy: I tell him I'm a dude and he tried to get my to lock my penis up!? What the hell!?

SecretlySophie:

What the hell dude, there's no way I'm locking my dick up. Now shut-up and leave me alone!

Stupid Chads and their stupid ideas, I thought darkly. I mean, yes, I was not well-endowed at 4" erect, but I hadn't even had sex with a girl before, so it wasn't even an issue. The only sexual pleasure I got at all was with my hand and I wasn't going to give that up on the suggestion of a random internet meathead.

And yet...something about the idea gave me a shiver. I stared at the screen. I felt the unstoppable simultaneous rush of shame and lust as my thoughts when haywire. I had heard that with no way to satisfy their lust, chastity drove some people to do radical, crazy things. To my surprise, my dick twitched.

55JUMBO:

Lol. look. I'm not going to force you. I'm just saying the more beta boi sissies who lock up their cocks the better. Put it on your wishlist, send me the link and I'll even pay for it

A chastity device...I mean I'd considered it myself...

I stopped myself. This is crazy! I tried to rationalise with myself: Why was I considering let an online stranger by me a sex toy! Plus he'd called me a 'beta boi sissy,' whatever that meant. It sounded like an insult, but that word, 'sissy', sounded familiar...on the other hand...I was getting the better deal, by far. I would in all probability never speak to this anonymous internet stranger again. He knew nothing about me, save my age, sex and the city I lived in: a city of millions of people. If anything, I was cheating him out of money!

SecretlySophie:

Fine. Here's my amazon wishlist link. Now leave me alone.

55JUMBO has left the conversation.

I leant back in my chair - phew! Apparently all it took to get a creep to leave you alone was to let them buy a sex toy for you! I smirked as I allowed this fresh interpretation of events to take hold of my brain, while I pushed down the humiliating truth.

***

I stared at the device in my hand. It was so small, so petite - as tiny as my cock was, I was still unsure this thing would fit. I'd already made an attempt at restraining myself with it, but I was hampered by both my 'growing' excitement (ironic, I know) and my unfamiliarity. I'd taken a cold shower and looked up how to put the damn thing on - this time I would be ready.

I know, I know...what was I even doing considering putting it on. It had arrived on Friday morning at the reception desk, and I had signed for it that morning with the full intention of throwing it away. Two days had elapsed since, to my surprise, the internet randomer had followed through on his word and bought the chastity device. In the cold light of day I only felt shame rather than arousal. However, I had been thwarted in my plans because a) I was late for class and had to jet and b) I thought it might look suspicious to immediately throw an unopened package in the bin.

All day long all I could think about was the small box in my bag, and slowly but surely, lust and horniness began to creep through my mind rather than shame. No opportunity to throw the thing away had presented itself, and all I could think about was how my friends would react if they found my little box of shame. As my professor droned on, the threat of discovery became mingled with the thrill of it, and by the time I had returned that night all thoughts of throwing it away had been abandoned. I had to try it on.

I carefully hooked the ring round and pushed the cold metal hood over my cock. Shrunken from the shower, it fitted easily. I made the finishing touches and finally, snick, locked the tiny padlock. I pulled my hands away slowly, unsure, but the small weighty device hung there. I drew myself up, and looked in the mirror. My skinny 5'10 frame looked back at me, looked at the small sliver of silver between my legs. The internet randomer's words came back to me: 'I'm just saying the more beta bois sissies who lock up their cocks the better.' Was that what I was? What the hell was a 'beta boi sissy' anyway? A shiver ran up my spine, and I felt a throb of pleasure from my cage.

I carefully set the keys down on the shelf in the bathroom, and walked to my desk. *clink*, *clink*. I looked down at the padlock jangling against the metal - it made a noise when I walked, and I could feel it on my cock. Why would people do this to themselves, I asked myself smugly. What a ridiculous idea - deny erections but make you more aware of your penis. Why would you want that. I smiled at the idea that people actually bought these and put them on themselves! What nonsense. I sat down at my desk and pulled myself up. I could take it off now...it had been a fun experiment. But why spoil the fun now? I decided to take it off after a couple of hours and toss it in the trash.

I poured myself a glass of whiskey and pulled up one of my favourite porn videos - a gorgeous dicked chick getting fucked silly by a couple of studs. She pulled off their trousers with urgency, ravenous to suck what lay within. She began pumping herself onto his cock while her hand went down to her own. My cock stirred in it's cage and I felt a throb of pleasure. Without thinking, I reached down and - felt nothing except metal beneath my fingers. I frowned. No matter how I tried to touch myself, or shake the metal prison encasing me, I couldn't feel anything - except an uncomfortable pressure between my legs as my penis tried and failed to get erect. Huh, I thought to myself. Why on earth do people like this? I continued watching, and although my desire didn't fade, my erection became weaker and weaker. This is so weird!

The video ended in classical style, as the two guys jizzed all over her perfectly made-up face. She winked into the camera, and began licking her lips and using her hands to get as much cum as she could into her mouth. It was the hottest things I'd ever seen - I'd never gotten this far in before, and the pressure built between my legs again. I again desperately tried to deliver some sensation with my hand again, anything, anything but that maddening pressure from the cage. Frustrated and annoyed, I shot out of my chair and minced over to the bathroom - the squeeze from the cage making it difficult walk. I scrabbled for the keys on the shelf, unlocked my cock with shaking hands, and desperately pumped my semi-erect penis for all I was worth.

I tensed, teetering on the verge...my breathing got faster and faster until... OHMYGODOHFUCCCKKKKK. The space behind my eyes exploded and my toes curled and I bit my lip, my eyes screwed up tight from the incredible sensations... AHhhhhh...I saw stars and shivered as the wonderful waves beat at my brain, my cock, my body...fuccckkkk...as the waves receded I heard myself panting. I slowly opened my eyes to the bright bathroom lights and felt empty, spent - absolutely exhausted from the strength of my orgasm.

As my eyes came back into focus, I saw I had covered the bathroom floor with my cum, I saw the keys in my hand...and then my eyes fell on the chastity device. So this is why people do it, I thought. My 10 minute jack-off session had taken an hour, and it had brought me the best orgasm of my life. As I began to clean off the floor, I thought to myself...well I don't have to get rid of it right now...