Sissy Prince Stories

14,095 results
Orientation
Length
Source
Infinite Scroll

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Restructuring Pt. 03

by cathynylons on Jan 29, 2020
Transgender & Crossdressers

My wife said, "Well now it's just us girls. Leland is going to a bar to watch the football game with some pals. But it's only 4 pm." Looking at Diane she continued, "It's so great to have you here, Diane, after so much time. It's great that we are re-connecting...and that our husbands get along so well. Ha Ha." "Yes," Diane agreed. "There is some good chem...

Letter From Palo Alto

by justincbenedict on Sep 17, 2017
BDSM

LETTER FROM PALO ALTO Dear Shoeblossom, My wife Lillian is also the keyholder to my Prince Albert piercing. Much of our time together my cock is struggling to erect against the cruel way it is locked in a bow shape against the piercing in my testicles... Lillian teases me a lot, and spends hours walking around in front of me wearing very little...demibras...

The Guy in My Wife's Panties

by Candyboi on May 1, 2018
Transsexuals & Crossdressers

The catalyst for the paradigm shift in the relationship with my wife of twenty years was something that happened at the beginning of December - though, truth be told (as you'll see), there were several other naughty escapades throughout the autumn that really should have awoken me to the realisation that Carla was becoming the dominant one in our relationshi...

Dolly's Python

by justincbenedict on Sep 13, 2017
Fetish

October 2005 "Hey, it's Mrs. Tarleton! How're you doing?" I heard my secretary, Marcia talking and giggling with my wife. " How're you, Marcia...you're the cutest secretary at Cooper, Tarleton and Strowbridge, girl!" I looked up, and there she was, my beautiful girl, Dolly Tarleton, her long, honey blond curls bouncing. I dropped my work to watch as my lo...

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...

Amanda Adams becomes My Queen Ch. 09

by ShyDenZen on Sep 15, 2017
BDSM

"Yes, Ms. Deborah..." I almost stammer, "I think the kind of procedure I'm here for today is called a 'Prince Albert.'" Her pretty blue eyes grow very wide as she stares at me. She blinks at me once, twice- maybe four times... She knits her eyebrows. Finally, she shakes her head a little- flipping her amazing hair. She says, "That's a piercing I can only d...

Pierced Desperation

by justincbenedict on Sep 25, 2019
BDSM

Ervin felt his cock, bouncing on the leaden testicles, as he got out of his car. It was such a funny old house that Isely lived in... She charged by the hour, claiming on her taxes that she appraised antiques. But her credit card "charger" was next to her bed... It had been quite a week, Ervin reflected as he climbed the steps onto Isely's porch. The Pr...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

50 Shades Of Pale Pink Sissy Ch. 03

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Fiction with adult themes. All characters are over 18. * A splitting headache greeted me as I awoke. The soft surface I was lying upon seemed to be moving beneath me, rolling from side to side with occasional pitches from front and rear. In my confused state I wondered if the feeling was related to the headache and the vague memory of being drugged. The r...