Sissy Prince Stories

14,095 results
Orientation
Length
Source
Infinite Scroll

Steph's Descent Ch. 05

by 62_goo on Aug 31, 2017
Fetish

Steph was enjoying her new lifestyle. She had two male lovers and one female. She had two new tattoos and new nipple piercings. But best of all she had a submissive husband who let her do all of this even though he professed to not liking it. Steph got together with Fitz and his twin brother Steve most evenings. Often it was both of them but occasionally it...

Dr. Gaylove Pt. 01

by switchhitter420 on Sep 13, 2017
Transsexuals & Crossdressers

Dr. Gaylove, or How I Learned to Stop Worrying and Love the Black Load Pt. 1 ***** As I came back up for air, gasping and gagging and spitting all over the 10", stiff, glistening black cock in front of me - standing erect and proud for the whole world to see like a dark pillar of dominance, a symbol of manhood and all that is virility, dripping potent see...

The Dragon Ring Ch. 06

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

"I thought I might find you here," he said, popping his head around the door. "We have pegged them with irony. They are to pay for a mercenary expeditionary force to go in and take control of the country. Then to stay and train a new army for you, there's sweet justice in that." His glee was overflowing, giving him an unnatural presence. "Come, this calls...

Steph's Descent Ch. 07

by 62_goo on Aug 31, 2017
Fetish

"What's your star sign?" Fitz asked. "Gemini, why?" Steph replied. "Well, I like the idea of a star sign tattoo. Do you know what Chinese Year you were born in?" "The Year of the Dog. Again, why?" "I'm going to do one of those too." Steph felt a shiver of ecstasy run through her. Fitz wanting to tattoo her always did. "I've also finished planning the d...

Chains Willing Ch. 08

by Radiantlies5 on Jun 1, 2020
Sci-Fi & Fantasy

Chapter Eight: The Red Letter and The Monster in the Mountain. I know... Tales of love take turns for the worst. Bad people bring bad things like shadows and strange omens of apocalyptic events. But, what if? What if the tale was about simply loving girl-cock and tentacles? And so the Red Letter remained unopened. The Monster in the Mountain stayed as...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Away with the Lads

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're invited to Dublin, Ireland with 10 other lads from your village. It's planned as a weekend of copious quantities of drink (Guinness), fast food (beef burgers and chips) and cultural interest (Girls). You fly from Southampton and costs are kept to a minimum. Aiden, The only Irish born lad in the group fails to show – selfishly this is good news, as unl...

Maid in Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

Not Sick Maid In Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...