How I became a sissy cuckold and started dressing girly

Becoming a cuckold sissy.

Becoming a sissy cuckold was not something that I ever imagined being a possibility. It wasn’t until I got a bit older and started dating did I come to realize what my reality would soon become. 

I spent years thinking I was just your average guy. Not some alpha stud by any means, just a normal average dude. Yet for some reason not only did I have trouble attracting girls but when I thought I did, they would just end up dumping me.

Not fully grasping what was going on, I figured it was due to differences in personality. Usually they’d act snotty and bitchy towards me, like mean girls and I’d be acting like a naturally beta guy. Ya know, the type that are eager to do anything you want because we’re so desperate to stay in a relationship.

Coming to understand the truth

It wasn’t until I got told point blank that my dick was tiny and cute, did I start understanding that I could never pleasure a female. Now all the little jokes and teasing that had happened in my relationships made sense. They weren’t joking at all really, in fact they all thought I was a fairy sissy beta boy!

Cuckold showing his tiny dick.

Cross dressing started taking hold

After spending a ton of time just sitting around pouting and edging my tiny dick, I found weird things happening. All of a sudden I was getting turned on thinking about wearing panties and dressing like the “mean girls”.

Eventually I was even fantasizing about wearing cute skirts, sandals, bikinis and all the outfits that my exes wore while they humiliated me. Soon I started experimenting with doing just that and my cocklette just kept getting hard!

Cuckold sissy reality setting it.

From humiliation to cuckold sissy status

It all came to a head when a girl I was dating walked in on me wearing panties. She laughed and dumped me immediately for being a sissy bitch. Later on another girl made me wear more girly clothes before talking me into dancing on the front porch.

What was fun at first turned to frightening when I heard the lock on the door click shut and the porch light popped on. There I was looking like a sissy bitch in front of all my neighbors windows. Yet still my clit-dick stayed hard like a total whore.

The final blow came when my ex feminized me further by making me dress completely like a female and then restraining me. She spent the rest of the night talking and getting off to a real man.

Cuckold sissy status had just been achieved and I didn’t even plan on it. My fate was sealed. After time passed I only found myself craving more humiliation, feminization and even began wanting big dicks to dominate me.

So although it was never my intent, becoming a cuckold sissy was obviously my fate. Currently I am taking it even further by being trained online by my mistress and princess.

Cuckold Cam

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