A Sissy Transformation

Let me tell you a little about Michele. Michele and I first met on the phone quite a few years ago. I think, to be exact, it was about 8 years ago. Now, Michele and I don’t speak daily or even weekly. But, we do speak on a fairly regular basis and I like to believe I’ve had a hand in her feminization transformation.

When Michele and I first started speaking she was exploring her feminine side with panties, stockings, and bras. She had never seen a mistress in person or ventured out into the public dressed as her feminine self. Over time, she became more comfortable with her feminine side and began to take on a womanly persona. I coached her on shopping sprees at Victoria’s Secret and we discussed her seeing a mistress on one of her business trips. Eventually, she started seeing a mistress on a regular basis and she began to blossom in so many ways.

Michele loves her toys and now she has quite a few, which she willingly and wantonly sucks for me and inserts into her pussy for me while we chat on the phone. She adores shopping but still keeps her dress up time confined to home, for the most part. Until recently, that is.

A New Sissy Assignment

I finally decided that Michele needed to step out into the open and become public. She has been experimenting with makeup and wigs as well as full outfits. She even went out one year for Halloween dressed completely as a female and managed to suck a REAL cock. I was so proud of her! So, it only stands to reason that our next adventure had to be something just as daring. Last week, I instructed Michele to get dressed completely in her best outfit, wig, and full makeup. She was to take her purse and go on a little shopping trip. I wasn’t sure if she could do it, but she did!

Michele was asked to go to the mall and visit the ladies room, where she would enter a stall and insert a tampon into her sweet pussy. After that, she was to step out of the stall, walk to the sink and wash her hands and powder her nose, as well as refresh her lipstick. Then, it was on to Victoria’s Secret. She had shopped at this particular Victoria’s Secret many times, but never fully dressed. Although, the salesladies there knew that her purchases were for herself, not someone else.

Michele walked into Victoria’s Secret and bought three wonderful outfits, including panties and bras, and even a little catsuit! The saleslady that helped her recognized her after a few minutes and was delighted to see her en femme. It was such a great experience and I’m so proud of her. Michele, you’ve come a long way, baby. I only hope that was the first of many adventures in public!

Kisses,

Tia