Sissy Dildo Stories

41,035 results
Orientation
Length
Source
Infinite Scroll

Black Cuckolding Journey Trois

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

Salutations, my friends and devoted readers. Wanda Philogene here. Your favorite Haitian dominatrix, taking the beautiful City of Brockton, Massachusetts, by storm. Ladies and gentlemen, I have some good news. I've dumped Sean Prescott, my favorite white dude, on account of him becoming possessive of me. Sean and I were cool, and we had some fantastic sex, b...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

Thank You Miss 'Nessa

by Cleverlicious01 on Sep 13, 2017
BDSM

Of one thing, Vanessa was most certain: She savored the feeling of taking a typically, naturally dominant man, and turning him into a servile sissy. By chance, Mike already happened to have the secret calling encased in his DNA. His alpha male appearance, with lean muscular physique and beaconing hazel eyes, would have made any other woman weak in the knee...

Behavior Modification Institute Ch. 13: Final

by NancyPan on Sep 25, 2017
Fetish

Thanks to all of you who encouraged me to continue writing this story. Stay tuned for new stories. Please vote! All respectful feedback appreciated. ***** "Wake up, Nancy. Rise and shine. Time to get up, sissy." I hadn't heard the key turn in the door lock, and I hadn't heard Ms. Jensen enter my room. I sat bolt upright, then remembered that I was wearin...

Mindy's Moving Day - CFNM Ch. 01

by BuckyDuckman on Sep 25, 2017
Fetish

Author's Note: Humiliation, CFNM and pegging lie ahead! I've had this idea for a while about an adventurous married couple on the edge of opening a new chapter in their married life. I hope you enjoy reading it as much I enjoyed writing it! On her first day in town, Debbie and I were Mindy's only friends. The professional moving company hired by Mindy's...

Sissy Slut Ch. 01

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

It had been quite some time since I had stopped in the club. Not that I didn't crave the pain I could infect on one of the sweet young things that came to the club. I craved it more now then I ever did a few years ago. But due to relocation of my job I had to leave the city and I couldn't find a club that catered to my needs. Now I was back and I was chompin...