Straight Husband Road To Sissy

by Terry (Seattle)

Our story starts some 25 years ago. A couple of years after my wife and I married, she expressed regret that she did not have more sexual experiences prior to our marriage. Other than a couple of blow jobs, I was her only sexual partner.

We had just moved across the country and did not have any friends of family in the area, so after thinking about it for a few days, I told her that I would support her as long as she agreed to let me know where she was and who she was with.

Within a week she was invited to happy hour with her new friends at work. That night she gave a co-worker a blow job in his car and swallowed his cum, which is something she would never do for me.

To no surprise, the following Friday she was invited to happy hour again and hung out with the same guy and a girl. Around 8pm she called and asked if the offer extended to both males and females. Of course it did. She arrived home about 3am but was too tired to tell me what happened. Instead, she waited to tell me the following day in a crowded restaurant.

There were at least ten people within hearing distance. Looking back this was the beginning of my journey as a cuckold. Over the next three years she spent most weekends with her boyfriend (the guy she slept with the most) and a few others, both male and female. This went on for about three years before we moved to another town.

She had a few experiences in our new city, but when she became pregnant with our child (yes...we confirmed it was mine) she decided to stop - or so I was told at the time. She recently told me that she had spent the weekend with her old boyfriend on several occasions, including at the recent wedding a friend of hers in Mexico.

Fast forward to now. We’re in the process of moving cross country again to a new place. I moved first by myself for about three months. Before I left, she told me she wants to be free in our new city to do whatever she wants....and she wants me to be a complete sissy feminized cuckold this time. Aside from the cuckold part, I wasn’t even sure what she meant. So she gave me a list and told me to “google” the rest.

My first step was to become hairless, but I could leave the hair on my arms. I was to tell the waxing shop exactly what I was doing and why. It was quite embarrassing as I was aroused the entire time. The second chore was to purchase panties and send her photos of me wearing them.

I cheated the first time and purchased them at an adult store where it felt less embarrassing. However, the second time I walked straight into the mall to a chains store for women and told them exactly what I wanted. I was beginning to embrace it.

The next step was to wear the panties all of the time and somehow “accidentally” expose to another man that I was wearing panties. Back to the mall where I grabbed some jeans off the shelf and proceeded to the changing room. I “accidentally” forgot to lock the door. I sat with my feet on the bench so no one could tell if the room was being used.

Within a few minutes someone opened the door and I pretended to be surprised. He apologized and then quickly laughed and said “nice panties faggot.” There it was...the first time I was called a faggot. I was confused but ultimately it was who I was becoming.

Now my task was to dress “gay” and hang out in the gayborhood of our new town. Let’s just say the town is very open to all genders, sexual preferences and everything else. One day while walking toward that section of town, a man approached me and said he would give me a blowjob for $25.

Seeing an opportunity to fulfill another task, I turned the tables on him and offered him $50 if he would let me give him a blow job...as long as he came in my mouth. I thought this would be some sort of awesome experience, but it took him less than 90 seconds to cum and it was over.

The final step before she arrives is to take the 7 inch dildo she gave me all the way in my ass. When I first saw this I thought there was no way it would happen. But somehow it gave me purpose and a goal to shoot for. When I purchase my panties, I also purchased a butt plus anal training kit and a smaller dildo. Within two months I was able to take her dildo all the way in my ass.

Fast forward to now....she’ll be here in a couple of weeks. I now have a drawer full of panties that I wear everyday. I shave daily...except for my arms. I practice will the dildo daily and I have added lingerie to the mix as a surprise. I also keep the apartment immaculately clean and will confine to do so when she gets here.

There is one final step, but that is to wait until she arrives. I am to take another man’s cock in my ass while she watches and then take his cum in my mouth. I’d be lying if I didn’t say I am looking forward to it.