Chapter I: The Curiosity

I didn’t know what I was getting myself into. All my life I had thought I was straight until one night curiosity got the better of me. I plunged down the rabbit hole and never looked back. My Achille’s Heel? Sissy porn.

Seeing the contrast of a dick on such a feminine body with a perfect ass and tits. It was almost like I was conditioning myself to associate dicks with my arousal. Once the lust for dick started to set in, I started finding my eyes wandering towards the guy more than the girl during straight porn. Soon, there was no more straight porn in my repertoire.

After a while, all I watched was men fucking shemales. And then... men fucking men. I was so addicted. And so eager to discover what it would be like to be fucked. I created a Grindr account, signing up as Vers, wanting to try it all. My pictures were very well received.

It took me a few months to build up the nerve but I soon met Adam. I soon found out what it was like to bottom, and soon found out I loved it. Adam was very into BDSM and liked to be dominant. What started as vanilla soon became more and more hardcore as he stretched my ass and before long I could quickly and easily take all of his thick 8” dick.

My ass was getting so sensitive, soon, during sex, I would forget about my own cock at all. Adam would remind me as soon as he grabbed it. I was too pre-occupied with the sensations in my ass to concentrate on staying hard and pretty soon I started finding myself limp and oozing like a tap with precum.

I started to notice Adam would punish me for getting an erection. He’d place a bag of ice on my dick and balls. He’d spank them. And whenever my dick would get a semi he’d grab it in his hand. Cupping it completely. And squeeze it. Keeping it tight and compact.

I should have known he’d suggest wearing a chastity cage. In fact, he threatened me with one. Well, it was more of a promise.

One day, after a dogging session in the woods, Adam took me back to his car. As always he forced me to walk back naked and before he would let me dress he had one last surprise for me. He pulled a box out of the boot of his car. He opened it up. It was a chastity cage. And a tiny one at that.

“Don’t worry, we’ll make it fit” he assured me. That night he locked me up. It was quite the squeeze. But luckily for Adam it was quite a cold night. He gave my dick and balls a good spanking. Which shrunk them even more in the cold night air. It was already cold enough when Adam reached for his glove compartment and pulled out one of those gel ice packs.

He broke up the gel of the ice pack. Crushing it with force. It made me shiver. Not just at the thought of the cold. But at the thought of what his hands could do to my dick. He could read me so well and knew exactly what I was thinking. He took his right hand and clenched it around my dick. It was already freezing cold. He squeezed so hard. Crushing it with the palm of his hand.

My dick had never felt so tight and compressed. He looked me in the eyes. Deadly serious. And smiled. “Get used to it”. He then took the ice pack with his left hand and quickly placed it on my dick after removing his right hand. The cold shot through my dick. It almost felt like it was burning.

Adam pressed harder and then put his free hand over my mouth. I gasped and struggled for air as he pinned me against the car for leverage, hand over my mouth, the ice pack flattening my dick. I looked down. It was like my dick had been buried. The ice pack was completely flush with the rest of my crotch. No sign of a bulge at all.

Adam then took his hand off my mouth, and pulled the chastity cage out of his pocket. He held it in my face. Taunting me. “Look at it. Barely an inch”. He pulled off the ice pack and before I could blink he had slid my shrivelled balls through and was already pressing the cage down onto my shaft. The cage buried itself deeper and deeper into my skin as Adam pushed. And then. A clink. He turned the key. And I was locked.

He gave my dick a wiggle and laughed. I looked down. Ready to see myself. Where I was once used to having a 5.5-inch flaccid ‘trouser snake’ I was now reduced to just a simple protruding nub of less than an inch. I put my hands on my dick and balls. The blood was rushing back to my groin and I needed a piss. I was so used to holding my dick whilst pissing. But now. Just a stub.

A stub I couldn’t aim at all. I tried to point it down but every time the nub would just bounce back up and point straight out. Adam laughed. “Can’t aim anymore, there’s not enough shaft left!”. I couldn’t help myself. I started pissing and despite my best efforts it shot out directly in front of me. And much faster than usual. Probably from the compressed urethra. Adam was besides himself laughing.

I felt a tingle in my dick. I was starting to get hard. I could feel my dick struggling against the cage. It swelled. The skin started poking through the slats in the cage. The cage must have only moved by half an inch before my dick gave up and I started to go soft again.

“Don’t worry”, Adam promised, “It’ll only be for using at the weekend... at first...”