Grinding Sissy Tumblr Stories

61,631 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

A Deal Offered

by LockedSissySubmissive on Sep 25, 2017
Fetish

I was sitting in the kitchen drinking coffee wearing my dressing gown when Emma left for work. We'd had a pleasant morning chatting about the various inconsequential matters that married people chat about but she had to leave for a meeting and looked fabulous in a smart dress suit and jacket. Even after almost two years of marriage I was still totally smitte...

Epiphany At An Epiphany Party

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

Author's note: This is an note to self I am sharing. There is no sex but lots on my own sexuality. I love adventure, but my wife only needs the traditional needs. She knows nothing about any of my sexuality adventures and would divorce me if she did find out about one of the hundreds. ** Dancing with Ladies ** I swing dance socially. I am used to going up...

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:...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Sissy Whore Ch. 02

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I wrestled with my emotions for the rest of the afternoon, sitting on the sofa trying to distract myself from the mysterious web chat. I'd been at this a long time now and I was used to conversations that went nowhere. Most of the guys that contacted me followed up with a dick pic and were not really capable of continuing the fantasy beyond the scant descrip...

My New Digs Ch. 02

by cuckytoher on Aug 21, 2018
Fetish

The ice cold water hit my tired body like a thousand stinging needles as the lights went on at 6 a.m. I jumped up from the floor to finish my shower in the two minutes allotted to me by Andrea and Marko. I quickly soaped myself up and rinsed myself down knowing the clock was ticking. If I lingered more than two minutes, the door would automatically lock and...

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Mistress Monique

by bleedndkn on Sep 25, 2017
Fetish

I met Monique at a show. She wore a tight black dress, dark eyeshadow and was by far the hottest girl at the venue. I didn't have a chance. A mutual friend introduced us and I became immediately enraptured with her and in the days to come would constantly think about how to spend more time with her. Then, after an evening with Monique and mutual friends at...

A Sissy's Forced Gangbang Pt. 01

by sissy77 on Dec 3, 2017
Transsexuals & Crossdressers

I have always seen myself more feminine than most guys I grew up with. Slim and hairless throughout my body, more curvy than muscular. Until my early teens (I am 25 now BTW), being a sissy for me meant not being masculine as other guys both physically and mentally. When i reached my early twenties it turned to me brainwashing myself through sissy hypo vide...