On the outside I've seemingly got it all; I'm a happily married 42yo guy with three kids and a beautiful wife, I'm fit and reasonably attractive, at work I'm a leader and have a tonne of confidence. But I've had a secret that has been a part of me since I was a teenager and discovered my first femdom, sissy, BDSM and fetish websites.
I bought my first pair of panties when I was 15, I spoke with men online, once I was 18 and moved out of home I visited professional mistresses, was fucked with strap-ons, pissed on, humiliated - and I loved it all.
I met men and women on old school chat rooms and Yahoo messenger, webcammed with strangers, met up with a couple and served them both, licking her pussy and was handcuffed to a bed while the Master took my anal virginity. I've read so many stories on this site and rubbed my sissy clit to so many caption pics.
But I always thought it was a phase, that it would pass and it was more important to have a wife who would be a mother, to be acceptable in society, than it was to fulfil my fantasies, which were to be truly owned, caged and humiliated.
I told my wife of some of my fantasies after a few years of marriage - when I first started she thought I was going to ask for a threesome - I'm not sure if because she would have been open to that - but instead I told her about chastity. I purchased a cb6000s and gave her the key, which she held for about three weeks but finally admitted that she didn't enjoy been mean. She still lets me worship her pussy but always wants me to finish inside her, rather than deny me. As lovely as my wife is she is certainly vanilla in the bedroom. We still love each other dearly but physical intimacy has certainly decreased, mainly due to tiredness from raising three kids and no time to herself. And while sex when we had it, roughly once every six to eight weeks was good, I still couldn't deny I had a fantasy that wouldn't go away.
Which is how I found myself on a cuckold chat room with the username "denymyorgasms", describing myself as a sissy dick beta wimp needing a real man with an alpha cock to train me and take control of when I could spurt my sissy juice.
After a few randoms and false starts I finally started chatting with a younger man, a 26yo called Steve. He was single, usually preferred women but also had a thing for humiliating submissives and taking charge. We became connections and I was told to call him Master Steve, or just Master or Sir. I was hooked pretty much from this point.
We swapped dick pics, his was significantly bigger than mine, circumcised and a good girth and length. He asked to see mine soft and hard, which I took on my iPad and sent to him. Soft was barely two inches while hard I could make just over five.
I had to share pics of my sissy pussy for him, and then was made to go and shave myself completely smooth. I was already shaving my chest and legs for sport so it was easy enough to do and I felt like I could explain it to my wife if asked. I must admit I did love how it felt and how much less of a man it made me feel by been smooth.
More photos were sent to Master and occasionally he would share one in a public room, exposing me for the sissy bitch I am. This only made my sissy clit harder.