My Feminization

littlechasteguy says:


I, as I imagine is the case with most men, certainly most men with submissive tendencies, often fantasized about forced feminization.  However, I never went very far with it because I thought that to be really feminized required being passable as a female. With my hairy body and the need to maintain my general appearance due to constraints resulting from my “vanilla” life I always figured feminization was not for me. But I did enjoy wearing female panties, of which I have a nice collection. Then, in casual conversation I mentioned this belief to Mistress Alegria. 

Mistress Alegria, I am coming to understand more deeply, is very perceptive and listens to all I say, often filing away little tidbits of information for later use. This belief of mine was no exception.

Several weeks ago I was over at Mistress Alegria’s when she just happened to be going through some the feminine attire she uses for those who want to be feminized. As part of my service to her I was helping her sort through her items. As usual I was naked except for my chastity cage. At one point she had me try on a skirt just to see how it looked. I enjoyed the feel and thought it looked good, although I again made the point that with all my hair I could never pass as female so feminization probably wasn’t for me.

That was when Mistress Alegria sprung her latest surprise upon me. She told me point blank that being able to pass as female was not at all important. The next thing I knew we were going through her items with me trying them on to see which items fit me. We soon had a collection of skirts and blouses that fit, although not everything matched. There was also a red and white French Maid’s outfit. Most items were rather skimpy and slutty looking. I was told that we would need to fill out the wardrobe. As we tried on the outfits Mistress Alegria told me that she would be taking me to various events dressed in these outfits and that I had no choice so there was no point resisting. While my mind still harbored a vestige of resistance my body quickly gave in as her little cock swelled with excitement in its cage.

The next day we went to a friend’s house to have some pictures taken. Mistress Alegria had me dress in an orange skirt and white top, wearing high heeled boots, for a number of photos. Some of these are now posted. That was the first time I dressed in the presence of someone other than Mistress Alegria, and I found myself to be perfectly comfortable.

On the way home that afternoon Mistress Alegria told me to pull over into a little shopping center. The next thing I knew we were in a shoe store, buying high heeled shoes in my size and a pair of casual sandals. The next thing I knew I had four new pairs of female shoes.

Leaving the shoe store she directed me two doors down to a little clothing boutique. We left there with several feminine tops and a little black and white striped miniskirt.

Since I knew I had no choice in this matter I decided to go ahead and embrace it. When I arrived home I looked online and found several more items that I thought might look good. With Mistress’s permission I purchased them. Soon I found myself with a complete wardrobe, including accessories.

Last weekend on Saturday night was my true coming out. Mistress Alegria had invited over for dinner several friends, including a Mistress friend of hers and her collared boy, along with another young lady in the lifestyle. I prepared a lasagna meal, including salad, garlic bread and dessert and served it in my new French Maid’s outfit. That was a tremendous experience. It took every bit of fortitude I had to maintain my composure as my excitement was boiling over. The combination of humiliation and what I perceived to be genuine compliments really was a lot for me to experience.

After cleaning up the dinner mess, with help thankfully, Mistress Alegria had me dress for the evening out. We were going out to the local play house for a social gathering. Again the excitement and trepidation nearly overwhelmed me as I dressed in my new black and white miniskirt and a black top. Black lacy panties, a pair of heels, an anklet, Mistress’s collar, my butt plug harness and a hat completed my outfit. I looked so slutty. However, all those present assured me I looked very good and would be fine. Again I decided to truly embrace my newfound circumstances and try to enjoy myself.

At the playhouse I did have a good time. I confidently pranced and strutted around in my slutty attire, amusing my Mistress and making her proud. I was again gratified when one of the young ladies that I did not even know complimented me on my outfit, noting that she really liked my top. I graciously thanked her for the compliment.

As the evening went on at one point Mistress had me remove my panties and bend over a bench so she could give me a little flogging. While not a pain slut at all I am very much an exhibitionist. This public flogging while dressed in this manner was highly erotic to me. However, later came the moment I somewhat dreaded.

Mistress Alegria and her friend Mistress M were discussing what a slut I looked and acted like. (They assure me that being a slut is a good thing.) Then Mistress Alegria asked Mistress M if she wanted to see just how slutty I really was. Of course Mistress M was interested in seeing. So Mistress Alegria had me remove my butt plug harness. She took me to a good spot and proceeded to finger fuck my ass. I squirmed and begged for more while Mistress Alegria explained that this was how I now received pleasure since “Her” little penis was locked up, deservedly so. In between my grunts and heavy breathing I agreed with my Mistress and thanked Her for fucking my ass.

Later that night Mistress whispered in my ear that she was very proud of me. I had endured a lot and grown a lot in my submission to her that evening. I was so happy to know I had made Her proud, and at that moment I too was proud of myself.

I must say the physical feelings and the humiliation of begging for more fucking in a public setting like that was truly cathartic for me. A completely new window has opened up for me, one that I think I can embrace and enjoy. I will say for sure that I am looking forward to more opportunities to dress in a public setting. I have an entire wardrobe to show off.

Those vestiges of resistance regarding feminization I had several weeks ago are now completely gone. If Mistress Alegria wants me to be her chastised little feminized toy I am more than happy to fulfill her wishes.

littlechasteguy