Confessions of a Sissy-boi

As a good sissy-bitch, my utmost activity is making sure that my wife gets the best sex as possible. As much as she wants, however and whenever she wants it from her lover. I am always there to accommodate her sexual needs. I know that as long as she enjoys her pleasure, so too that will translate towards me being happy for her.

It was a long time coming for me in this journey towards revealing my other life as a sissy/crossdresser. It was equally hard for me to accept that this truly was what I wanted to become. The idea has always been in the back of my head, loving how elegant I looked whenever I try on my wife’s panties in secret. 

This fetish goes back during my college days. But even then, I knew I had to be careful not to allow others to find out. But as I got older, I then discovered my love for watching Interracial Porn. Seeing the way white women submit to gorgeous black men. I wanted to be like one of those women. So many nights I would pretend to be sucking a black man’s cock. Loving the way his dick stretches my mouth. I found myself getting hard just thinking about it. Yes, I did get to try it out eventually. But I never intended for it to become a habit.

It took another couple of weeks before we found someone who would be welcoming to our lifestyle with me dressing in my wife’s clothes, sitting back and watching the bull fuck my wife. 

At some point, the habit went away when I met the woman that ended up becoming my wife. I thought I was finally cured, especially after we began having children. Then we got into our forties, and it was then that I rediscovered my love for IR porn, and decided to share it with my wife. She, surprisingly enjoyed watching them. It was her who even reignited my love for crossdressing, when one night we decided to role-play, and she insisted that I wear her clothes while she pretended to be a man wanting to seduce me. Need I say that the sex that night was spectacular.

The flood gates opened after that night. We did more roleplaying fun, before deciding that it would be way better if we got someone in bed with us. Me having it out with another woman was out of the option. But her with another man sounded way better. We both decided he should be a black man. My love for my wife reached astronomical heights after that decision.

It took weeks, but we finally found our right man. We met him at a motel, and he gave my wife the best damn fucking I could never match. She was hooked from that moment onward. We got to spend more time with the man, but he kind of freaked out one time that we met him with me dressed as a woman. It took another couple of weeks before we found someone who would be welcoming to our lifestyle with me dressing in my wife’s clothes, sitting back and watching the bull fuck my wife. 

The bull got to be a steady regular for us. Even better was when he allowed me to suck his cock while my wife watched. She was shocked at first, but not upset; according it her, it seemed to fit with me starting to embrace my feminine side of wanting to become a sissy. She got me wearing a chastity cage, and the bull did some research and booked me an appointment with a specialist doctor who began prescribing pills that would enhance my femininity a lot more.

My wife now regularly fucks me with a strap-on dildo, and she loves watching me suck her bull’s cock until he gets hard enough to want to fuck her. 

So far, we have been careful with our cuckold relationship. We have done our best to keep it away from our kids ever knowing, especially our neighbours. I go to sleep wearing my wife’s panties, and sometimes with my chastity cage in tact. My penis has continued to shrink to the point that I barely recognise it as anything beyond a stub. 

Our steady bull has talked about finding me a bull of my own who would get to fuck me while he gets to fuck my wife. It sounds scary, but I’m looking forward to the challenge.