Sissy Contract Stories

32,406 results
Orientation
Length
Source
Infinite Scroll

Proud To Be A Sissy Ch. 10

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

The next morning I woke alone in the middle of the bed I could feel the weight of the fake breasts on my chest and the tenderness between my legs. I still felt as if my anus was gaped wide open from the fucking I received the night before. I shivered hugging myself tightly barely believing that Mr Lester actually managed to put his monster sized cock up my a...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

Heiress MMM gets Her Cuckold

by mmms_ricki on Sep 19, 2017
Loving Wives

Mary had recently inherited a rather large family fortune and become a multi-millionaire. As a result She was feeling extremely Independent and Powerful. Now that she was independently wealthy she had the urge to release Her Female Supremacy and Female Dominance side. She especially looked forward to showing off the Power She had over Her sissy submissive hu...

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

The Dragon Ring Ch. 07

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

I saw place names and looked to find mine; it was on the left front. On the right front where I expected to find Sissy's was the coat of arms of the S'snoyme kingdom with the legend of 'Giver of the Bride'. I was horrified. I grabbed the marker and rushed double time to the reception room. I spotted Antic and rudely took his arm. "This is an abomination!"...

My Wife Turns Me Out At Book Club

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been 3 days since the event, and my mind is still reeling. I can't believe my wife took me as far as she did in one night. Sharon had told me a few weeks ago that the neighborhood book club she attends was having a special couples night. Apparently the wives had discovered that their husbands enjoyed the idea of group sex and partner swapping, and eve...

The Suitcase Ch. 03

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

The saga continues in Part 3 of The Suitcase, where Georgina gets some body mods and her Daddy reveals the more sinister plot. Keep reading if you want to find out where our sissy will go next. Enjoy! ***** It was like I was dreaming. My tall, hunky Daddy was leading me down the stairs to a sex dungeon which was packed with toys, while behind me was anot...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....