Tied, Forced, and Caged

This was the real turning point when I truly became a sissy. I'm sharing this memory with you now.

When I was younger, about 20, I would secretly cross-dress. I'd find a clear evening when my flatmates were out, or if I was traveling and in a hotel. I would start by making my skin smooth, sometimes with a razor, sometimes with cream. Then, I'd give myself an enema to clean my ass. Then I showered, moisturized etc. Then, at last, I would do my nails, then get dressed, and finally my makeup. At first that was as far as I would go, but over time I became more adventurous, and Grindr was my main outlet. I would chat to guys at first, then I escalated to hooking up, just to give blowjobs. This is the short tale of one such hookup, the hookup where I was first caged, and where I lost my virginity.

It was about 8 pm. I wore a black lace bodysuit, black tights, a minidress and heels. I was on my third glass of wine and I was horny. As I often did I opened Grindr. One man in particular caught my eye, and I chatted. He was a bit older, dominant, just my type. And he wanted to meet up. I told him I would only do blowjobs, which he was fine with. He sent me his address. I threw on some over clothes, then left to meet his car - he was picking me up. At his place he showed me to the restroom where I finished getting ready, then I met him in the living room. We started off kissing and stroking each other, then he asked me about my kinks. Eventually he teased out that I fantasized about being tied up - he offered to do it, and, with a strange sense that he was trustworthy, I agreed.

He tied my hands behind my back, attaching them to the back of a collar he put on me. He laid me face up on a bed, and tied me down so I couldn't move. Then, he showed me his phone screen, which had my Reddit account displayed on it. I had no idea how he'd found it, but he read from it and told me my other kinks. He read my post that I wanted to be in chastity, my post that I wanted to be tied up and forced, that I wanted anal. Then he told me that he was going to fulfill my fantasies. I was hard, so he started by jerking me off, with his TV playing sissy porn. He caught my cum in a glass, held my mouth open, and made me swallow it. Then, he placed a flat cage on my now flaccid clit. It had a built-in vibrator and a tube to allow peeing.

I saw his cock. He was rock solid, and easily 3 inches longer than mine. He told me that to be a true sissy I had to have a man cum in my ass, and as he told me this I felt him lube me up. I tried to wriggle, to move, to escape, but with no success. Then, slowly, I first felt the pressure of his cock on my anus, slowly increasing, until suddenly I gave way, and he was inside. I protested initially, feeling violated, but quickly the pleasure I felt overrode my brain and I was enjoying it. I moaned and groaned as he fucked me, and I nodded when he asked if I was glad he'd forced me. He'd pushed me through my reluctance to a place I loved.

He kept fucking me, and I had an orgasm. Unlike my earlier cum, this was full body, it was amazing. Eventually, after maybe an hour, he came, shooting deep down my hole. Quickly, he pulled out and pushed in a butt plug, before showing me how he could control both vibrations. I wasn't thinking straight, so when he moved to drive me home I got straight in the car. It was only when I was back in my bedroom that I realized I was still caged, and he had the key. I had no idea where he lived, I could just message him online.

"Yes, I kept your key, and no, I won't give it back. It's for your own good, you need to be pushed to embrace your inner sissy. Let it remind you of your true self." I argued and demanded it back, so he offered to unlock me if I completed a challenge. I had to get fucked and creamed by 5 separate guys. At this point, I didn't really need an excuse to slut it up, and I enthusiastically began. That is another story, but after the challenge I decided I wanted to keep the cage.

That was a few years ago. I've changed cages, but to this day he keeps my key. I've 'earned' that key a hundred times over, but I've always refused. Instead, he sometimes gets me new lingerie or clothes. He has access to my Grindr and other accounts, and he picks men for me to fuck. I'm not even sure if he keeps the keys, as opposed to throwing them down the drain. Either way, the cage stays on.