Sissification Cross Dressing

Two Roads Less Traveled (follow up to Jennifer’s Fame)

In Jennfer’s Fame I outlined the scene I had for Joshua/jennifer; read below how it all materialized as per Jennifer herself!

THE JUICY DETAILS- It All Starts With A First Step….

We had emailed back and forth several times to set things up and develop a scene. Lady Anya knows my nature as a submissive sissy and is impressed with how sexual, sensual and uninhibited I am. She met me at the gate of the apartment complex and led me to the parking lot. Her dress and demeanor were so powerful and sensual and she thought nothing of walking across a parking lot full of men and women, who all stared at her in amazement. Inside the apartment I was made to strip. She told me everything she was doing as she did it — the enema, the nipple clamps, the vibrator on my sissy clit as she did my make up and then had me dress. I was in one my dazzling outfits with a great pair of heels. We walked to her car, again in broad daylight in front of the entire world. Her strength gave me courage to expose myself so. We had a lovely and pleasant conversation during the 15 minute car ride to a shared dungeon. There we met one of her male slaves. Being inside the dungeon was so erotic and exciting. I was cuffed to a padded sawhorse, while her boy toy was tied onto a sort of padded medical exam table. Lady Anya enjoyed pulling up my skirt to admire my perfect ass and then inserted a dildo into my sissy pussy. After leaving me to squirm in delight for a few minutes, she began to use various paddles and crops on my ass, teasing and humiliating me and complimenting me on not using my safe word — pink polka dots. Eventually she brought me to the point where I had to use the word, but she enjoyed my shame and uncuffed me, tied rope around me and led me to her waiting slave. Then she “made” me such his cock — not that it took a lot of force, because I love sucking cock — and photographed me being a little cock sucking bitch. She then went off to contact a third party she had invited to watch the fun. I brought her slave to the point of climax and he asked her if he could cum, to which she said yes. Seconds later I had a mouthful of creamy cum, but since I had not been told to stop I continued sucking for 10 minutes before she took me into the other room and tied me to a Saint Andrews cross. Helpless and aroused I stood exposed while she whipped and flogged me. After awhile it was back to the padded sawhorse, where I was cuffed in place again. This time she took a large headed vibrator and began pressing it against my sissy pussy. It felt so good! And she could tell it felt good, and spoke encouragingly of my sissy willingness to be penetrated. My pussy was beginning to open up and I think she was going to see is I could take the entire head of that monster into my ass, when her third party arrived. I was uncuffed and told to stand in the middle of the room, with my eyes down. Then I felt the eyes of a strange man staring at me and I was allowed to look up as SHE and he discussed my looks and abilities like I was an object. Then I was tied back to the Saint Andrews cross. She allowed him to whip me for some time, enjoying my punishment and humiliation almost as much as I was. Eventually the man left. Lady Anya rubbed balm onto my red marks to prevent bruising and had me and HER slave clean up. Then we went back to the apartment, once again walking unabashedly through the parking lot while a group of Mexican workers undressed us with their eyes. She helped me clean my make up off and I got to see her magnificent breast as she changed clothes. Then we walked to our cars, hugged and I left. Over the next days and weeks we emailed back and forth. She is certainly a Mistress who feels the joy and responsibility of slave ownership. She has a keen sense of your needs and limits and knows just how to push the right buttons. Lady Anya helped convince me that my true nature was that of a sissy and she has encouraged me to bloom into a fulltime gurl. You could not ask for a more sensual, satisfying encounter than SHE is willing to give YOU.

Jennifer has continued in her path to crossing over to Womanhood as evidenced by her latest magazine spreads:

Looks at HER here too:

From a Favorite admirer of Jennifer:

Jennifer will continue on her path as she climbs the far reaching Tower of Transgender modeling….My dream is to soon see her in fabulous St. John or Gucci !