Sissy's Online Mistress Ch. 01

I hadn't dated in a year and while other young men pursued relationships or casual sex, I did neither. I locked myself in my bedroom, logged onto my computer and frustrated myself with porn. Some days I would get nothing productive done, I would jerk off or sometimes just let myself get hard and enjoy the frustration.

I was ashamed. My peers were progressing through life and I was just in a pathetic rut. Worse than that, I was getting worse, the porn I was consuming was getting increasingly more perverse.

I found myself on a forum for crossdressers and dominants and began to roleplay. My face would burn red and my 'clitty' would get when these strangers called me a 'good girl' or a 'sissy slut'.

They encouraged me to buy lingerie. They wanted me to waste my meagre wages on underwear I could never show to anyone else. One person in particular, who insisted I call her Mistress, was keen for me to explore my feminine side.

At her instruction, I shaved my body and slid a pair of panties up my legs. Then I pulled some thin tight leggings. The soft fabric on my smooth legs felt like electricity.

I looked in the mirror and tried to convince myself that this is what normal guys do but I couldn't. My legs did and arse did look shapely in the mirror but a stubborn bulge showed in the front of my leggings. As I appreciated my figure and ran a hand down my thighs, the stubborn bulge in my panties got harder and I felt horny like never before.

That was the first time I masturbated in panties, but it wasn't the last. I took pictures of myself crossdressing or simply in women's underwear, careful to obscure my face. I uploaded them and waited with bated breath. I got almost as excited waiting for dominants to degrade me or fellow sissies to praise me.

Mistress said she was proud of my progress and that she had some things she wanted to send me, but I was too nervous to reveal my address. At that time I was still living a fantasy: I thought I could be a sissy in my bedroom and a normal man the rest of the time. I was too cowardly to risk my sissy fetish finding me in the real world.

Mistress expressed her disappointment with my lack of trust and commitment and stopped paying attention to me. I sent messages begging her for forgiveness. I needed her attention, either her praise or disdain, I couldn't bear her indifference.

After a week of anxiety she replied that I could continue to be her online sissy if I sent her pictures every day. I eagerly accepted.

She would send me links, outfits she expected me to buy, wear and model for her entertainment. I was burning through money getting clothes that were sluttier and sluttier. One day I was a latex nurse and another I was a sexy bunny.

She expected me to be completely smooth every day and sent me a link to an epilator. I started the process of removing the hair below my eyes. I started a diet, I had never been big but soon my stomach was as flat as a model's. I struggled to focus on food anymore, every waking moment was spent thinking about how to please Mistress.

I bought sports tape and Mistress instructed me on how to tuck. She said no one wants to see my silly sissy clitty and anything that stopped me touching myself was a good thing. I would push my balls up in my scrotum into my pubic area. Then I folded my empty scrotum around my soft penis and would tape it together. I would then pull it as far back as I possibly could and secured it with more tape.

I took more pictures of myself, some of them where I was tucked. I pulled up some yoga pants and couldn't believe how feminine I looked. I had no bulge, but where my scrotum was folded either side of my penis I had a faint camel toe.

I got so excited that I got careless. Before I knew it I was sharing photos of myself where my face was visible, in the frustrated horny mental fog I even forgot to remove location tags from the photos I sent to my Mistress.

She encouraged me to try makeup and I spent more of my savings on primer, foundation, blush, eyeliner, eyeshadow, mascara, lipstick and more brushes than I could count.

I practised but when Mistress demanded to see her pathetic sissy slut in its hooker makeup I said I wouldn't send photos of my face.

She told me I was a stupid sissy and an ungrateful whore. She then sent me some of the photos I had uploaded where my face wasn't obscured. She said she already knew what her sissy slut looked like and that she wouldn't tolerate anymore disobedience from a pathetic sexless sissy.

More and more she asked me how I masturbated. She told me as her submissive sissy she didn't want me touching myself. She made me agree I wouldn't get hard, erections were for men, not for silly sissy masturbators. I didn't know how she hoped to enforce this.

One day I got a package in the post. I had a sinking feeling in my stomach, when I realised Mistress now knew where I lived. I opened the box to find a small metal chastity cage left unlocked, a key separate to it, a short leather skirt, a small handbag, high heels, a blonde wig and a pink crop top. A note said not to touch it until she messaged me. She told me to put on the outfit, "all of it" she emphasised and send her a photo from a public bathroom showing my contained sissy clitty.

I couldn't, I told her, no one knew I was a sissy and I couldn't risk going out like this.

She didn't respond at first. Then she sent me a link to my facebook account. Then the accounts of all my friends, family and colleagues. "Which photo should I send your parents first?" she asked and then sent me some of my most shameless selfies. I agreed to her demands.

I stripped and put on the skirt and the top. I fitted the wig and put on some makeup. I even put on the heels and practised walking in them. I did everything I could to delay putting on the cage. Finally I squeezed my balls into the metal loop at the bottom and squeezed my penis into the bent metal tube. I had to wait for my erection to subside, my penis was so hard that I had to press the cage hard against my crotch to seal it. It clicked shut and to my surprise it locked without needing the key.

Immediately I felt the need for release as my penis strained desperately against the unyielding metal. I sent a hand down there instinctively trying to tug on my erection but it only found cold steel. I pulled at the cage but got no relief and I felt horny and angry at myself.

I grabbed my new handbag and went to leave my flat, at the last moment remembering to take the key with me.

I had never felt so naked, the gaze of every person I saw threatened to melt me. I hurriedly made my way to a local public toilet while keeping my eyes fixed on the ground. As I walked past, looking like a whore who was late to work, I could feel men's heads turn to follow the click-clack of my heels. I heard a group of men chuckle and my face turned red and my locked away penis yearned for release.

When I got to the loos I realised I couldn't go in the men's room, swallowing nervously I pushed open the women's room's door. I let out a sigh of relief when I saw it was empty. I quickly went to take a picture in the mirror in front of the taps and then remembered Mistress' words. I lifted up my skirt to show my imprisoned sissy clitty and took another photo. I quickly went back to my flat, careful not to make eye contact, slightly more confident having passed Mistress' test.

I sent the proof to Mistress and reached for the key. The metal was digging into my penis that felt like it was ready to get harder than ever before. I licked my lips, I was so desperate to get this cage off my penis. The key didn't seem to fit the cage, I thought that in my haste to remove the cage I was being clumsy but minutes of my efforts yielded nothing. With a cold realisation I gave up. The key wasn't for the cage. I looked at my phone and saw Mistress had sent a new message.

"You have done as I asked but a good sissy wouldn't have needed encouragement. I am disappointed. I need time to think of an appropriate punishment. I will contact you in two weeks time, perhaps by then you will have learnt some humility and gratitude. At least you will find it easy to keep your promise and not touch yourself!"