All through our relationship, and before it, I have been a crossdresser, something my wife liked a lot and pushed me to be the best I could be without actually living as a CD 24/7. I never had the desire to be a woman or to dress 24/7, well apart from in my fantasies, that is, I confess I have loved the idea of being able to be a sissy 24/7 365 and serving full-time as a sissy maid for Mistress, but obviously, real-life commitments make that impossible.
There was a big change in our relationship when I started to lose my libido and the ability to maintain an erection during sex. Do not get me wrong, I admit I was never the worlds greatest lover for my wife, but at least I could perform enough to bring pleasure to both. Even when turned on, I found I could not perform in the traditional sense. We tried Viagra, but that did not work at all; all the pills did was give me a headache the day after.
We did consider the doctors, but we put it down to me turning 40 and because I had been wearing a chastity device for more extended periods. My wife insisted on no time in chastity for a few months to see if somehow things fixed themselves, but they never did. Even though I hated to let down my loving wife and to know she was disappointed, I also felt no real need or strong desire for sex anymore, "with anyone". I was, and still are content, not having the pressure of sexual performance anxiety on me. I asked if I could go back into chastity, she agreed.
Being active in the kink community online and nights out at club events, we posted about this issue in forums and even spoke to some kink friends in person. Even though the idea never entered our minds beforehand, many people mentioned cuckolding as a possible solution? Even though we are both very open-minded, neither considered it or took the idea seriously early on. I was reluctant because even as a sub and sissy, I did not know if I could deal with being submissive around any man, let alone him being with my wife too.
It's funny how things pan out in life, though; fast forward months and I was now a regular online looking and commenting on anything and everything cuckold, Femdom and sissy related. My wife does too, but she tends to leave me to it. She occasionally will join a chat if she takes a particular interest. Still, her looking online at kinky stuff is usually limited to chatting with our kink friends or arranging a night out for an event. Even though I have stayed in chastity, I have to admit that being inundated with so much interracial cuckold porn every time I turned on the PC, my balls often soon turned blue, and my nano-cage felt even smaller than it already is.
With my wife noticing this change in me, we tried resuming our former sexual relationship, but even though I was turned on like a dog in heat when in my chastity, I soon let her down again when out. It was this second failure that made up her mind. So, she decided to bite the bullet, and we tried to find someone into the BDSM, kink lifestyle as well as cuckolding.
Fast forward a few months; it's Saturday night, our daughter is staying out for the night with college friends, and I am helping my wife dress for the 5th date she has with a Dom Black guy called Matthew which we met two months ago. We met him through an online swingers group. Initially, we met him together for a casual drink in a bar one afternoon to say our hellos and see if we gelled. Luckily for us all, we did.
Even though me and my wife are nearly 20 years his senior, he took control of that first meeting like he was a well seasoned Pro in the domination scene. He was totally charming, a gent full of natural confidence that perfectly suited his physically strong body and good looks. In those few hours casually drinking and chatting, we all established that we liked each other and also the pecking order. Telling him our story about how we came to the cuckolding decision, he laughed and said that it's a common scenario for couples to seek out a Black Alpha when the sissy boy can't perform anymore. I felt like every eye in the world was on me at hearing him refer to me as a sissy boy; my face burned red, or at least it felt like it did red at those two simple words. My wife seemed to enjoy hearing them also because I saw her blush and squirm in the seat. Hearing his words and her reaction did something I never expected; I felt a wave of excited sexual bliss go through my body and culminate inside my chastity cage and nearly made me cum. I could not believe it; I actually almost cum in my pants whilst wearing chastity, and without any physical stimulation, simply by the words a man said.