Sissy Princess Stories

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Orientation
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Infinite Scroll

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Mistress Marisa's Estate Pt. 07

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... *************************** I hear you ring your bell. Hurrying to your bedroom I almost trip on my 4" spike heel shoes on the stairs. You decided that my...

A Husband Named Cathy Ch. 02

by cathynylons on Sep 18, 2017
Transsexuals & Crossdressers

When Toni had finished inserting my butt plug she turned to me and said, "There, now you'll see how much more feminine you walk. We will be going out later this afternoon so I think now would be a good time for you to go to your room and think about your behavior yesterday." I went to my room and sat at the vanity and began applying my eyeliner, eye shadow...

Payson's Wedding Ch. 02

by fantaseeboy on Jul 16, 2019
Transgender & Crossdressers

The next morning, Becky and I walked into the jewelry store a few minutes after it had opened. The older man who owned the store looked at us with a funny expression on his face. We approached him hand-in-hand. Becky, with her Hispanic heritage, was wearing jeans, a white blouse that draped over her giant breasts in the most alluring manner, and white cross...

Miss Guided Pt. 02

by MissMarianne on Mar 26, 2019
Transgender & Crossdressers

I arrived at Dr. Bill's office and he greeted me and we sat chit-chatting together for about ten minutes. Then, Charles and Emily arrived. Dr. Bill addressed us all. "I have read Dr. Price's diagnosis and report and I concur with her findings and recommendations. It's probably best that Dr. Price tell us about them herself. Dr. Em began saying, "Well, f...

Auntie Jean Drummond Lloyd

by Sissy Adele Howells on Aug 31, 2017
Fetish

I had been caught red handed. My kinky secret was now known by the stewardess of my local club. At 45 years of age, without a girlfriend, my world was about to change. Of course this was a fantasy dream, but everything was so real. Stewardess Jean Drummond Lloyd was 58 years of age. Sixteen stone of obesity, with short, blonde, curly hair. This was going gr...

Ugly Duckling to Sissy Princess Ch. 03

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 2) Wow! The kiss! Wow! Before I knew it, I was sitting on Ted's lap straddling him and we were French kissing in the most passionate and intense kiss of my life! I don't even know how I got up here. Maybe I climbed on his lap or maybe he grabbed me and pulled me up here. I was in bliss! The kissing was so amazing that my whole body j...

Mistress Marisa's Estate Pt. 22

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... *********** I hear the female chatter as I come down the hall from your kitchen and main bar area. I have a tray full of margaritas. As I enter the room I...

Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...