Dear Forced Womanhood,
It all started out when I discovered that my brother Kenneth was wearing my bras and panties. Now that his secret was out he asked me if I would help turn him into my little sissy sister. I had always wanted a little sister to be “girly” with so I started Kenneth on your feminizing hormones and then soon supplemented these with estrogen shots as well. After about nine months of the hormones, and corset training to nip in the waist, his body had softened and curved like a woman’s and we were able to get large breast implants put in. As was usual by this time, I had my sissy sister put on her corset so I could cinch it up tight as a painful reminder of what it takes to truly be a feminine sissy! This day was a little bit different though, as we were going to see a judge about having her name legally changed from Kenneth to Karen. I told her to put on her pink leather mini skirt, white transparent ruffled blouse, white nylons with pink bows, and a pair of white 6″ stilettos. Perfectly looking the part of a sissy girl the judge approved the name change immediately and gave Karen a long, lingering gaze as she minced out of the courtroom in her dangerously high heels!
Three days later I had her frenum pierced in anticipation of fitting Karen’s sissy clit with a permanent FL4 chastity. The poor dear went through quite a bit that day as we also had her ears pierced three times and tattooed permanent makeup on; dramatic eyeliner, cheek blush, and bright pink lips! After a few weeks of healing Karen was thrilled to put on big pink hoop earrings to enhance her permanent slutty makeup.
We both dolled ourselves up in tight dresses, lacy lingerie, and painfully high heels for our first double date as “sisters” with our new sexy boyfriends. My sissy maid sister gave her very first blowjob to her boyfriend, taking his cock all the way in her mouth and loving every minute of it! You would never know this was her first time as she swallowed it up with such skill and enthusiasm, until he exploded over and over, in her mouth and across her face. Later, at the drive-in movies, her boyfriend began fucking Karen’s pretty little ass, hard enough to rock the car back and forth on it’s squeaky shocks.
When my new little sissy sister and I got home that night we had our first girl to girl talk about our boyfriends. We talked all night long about how it felt for her to look, act, and feel so much like a woman, and how thrilling it was to be fucked so hard in the backseat of the car. She admitted it was slutty of her but that she loved feeling that way!
Next week Karen is going to the hospital to have her tiny penis removed and complete her sissy transformation into a real woman with a vagina. She is so very happy at last and begs you to publish this letter in Forced Womanhood magazine!

Thank you,
Mistress Sister Penny

This letter was originally published in Forced Womanhood 67