Femdom Gets a Crossdressing Sissy Girlfriend

Before my husband and I got married, we met in college. His female best friend happened to be my roommate, and figured I needed a break from the usual string of asshole frat guys I was dating. I had never really met a man like him before.  He was sweet, caring, compassionate…. He was everything they taught me a man should not be. Those were traits a woman should have, and only after dinner is hot on the table and the man has a glass of scotch in his hand. Yeah, I guess you can say I never got on with the older generations. They were not happy I went to college out of high school, instead of marrying and living the middle-class lifestyle. Imagine how they’d react now, if they could see how my husband/sissy girlfriend and I live!

During college, when my future husband and I were still dating, I had a psychology class that started delving into human sexuality. Through this, I discovered the world of BDSM. And, after telling my boyfriend about it, he explained to me his previous relationship was as the rubber gimp to a very sexy lawyer lady, who had made him a cuckold. While I was aghast at this, still holding on to my small-town values somewhat, he eventually explained that I was his first actual sexual experience. That night, as we made love, he called me Mistress for the first time.  And it certainly was not the last.

Mistress Behind Closed Doors

As college drew to a close, we got a place together in the city. Not too big, not too small. Perfect for a couple of college seniors looking to explore a newfound sense of sexual purpose in private. We started off the same way most new couples in this situation would, I guess. I had him doing the chores, cooking, cleaning, all that good stuff, while I focused on my degree.

I wanted to be a therapist, get into the heads of people, figure out what made them tick, and help them find closure with their demons. Of course, I knew if any of my psychology student friends saw me in that house, my naked boyfriend doing the dishes, while I sat with what we eventually came to call the sexy librarian look, a button-down shirt, a tight pencil skirt, my thick rimmed glasses, and my hair pulled up, they would have a field day.

Things progressed, and I learned different bits of the lifestyle. While clothed female, naked male was something I technically learned about later, we practiced it daily. I just love the sight of him naked.  My first order, in our new place together, was that, unless I gave him permission, he was not allowed clothes. CFNM worked for the longest time, until I stumbled upon an ad for a sissy school. And then I started getting mischievous ideas on how to turn my naked submissive boyfriend into my clothed submissive girlfriend.

A Sissy Girlfriend Is Made

We went to a few stores, supposedly to pick up clothes for me. He has a small frame, and I fit into his clothes perfectly. I assumed the opposite could be true and kept that in mind. Most people go for the sissy look, which is poofy dresses, a lot of pink, frilly undies. I did not want that.

I decided that he was going to be the woman my parents wanted me to be. Floral print dresses, pearls, heels, and stockings. I also got him panties and a new bra. I was not going to share mine, after all. Of course, he did not know any of this was for him at the time. After all, this was for my amusement, so I knew he would not disagree. When we got home, he set the bags on the counter and began to strip as usual. I decided to give him one last, officially male thrill and we made love. I told him to do it like it was the last day he had his dick, and it was wonderful. When we woke up in the morning, he found out why I told him that.

A New Beginning

We showered and cleaned up as usual, and then I explained our new course for behind closed doors. He was to begin the process of feminization that very day. Behind his back, earlier in the week, I had acquired a wig for him that I assumed would make him look like Donna Reed. I could not help but laugh when I got him in the panties and bra. He looked so silly, and I think the humiliation of it all got to him, cause his penis was harder than algebra. Eventually I put it in chastity, but that comes later. I got the idea to put two small melons in his bra. I figured these would serve as breasts until the falsies I ordered arrived.

The dress, the wig, the pearls, all of it together looked quite beautiful on him, I must say. And, before class, we made love again. I explained that from now on, he was to wear these items at home. When he got home from his last class, he would apply makeup. To this day, it amazes me how good he is with his own makeup. And that is the tale of how my submissive boyfriend became my crossdressing submissive girlfriend.

Want To Become A Sissy Girlfriend? The Feminization Mistresses Can Help! Call 800.730.3593