Terror To Sissy Stories

359,934 results
Orientation
Length
Source
Infinite Scroll

Driving Her Home

by bored_doe on Sep 16, 2017
BDSM

Alan smiled at the perky blonde college student in the passenger seat of his sedan. "So Catelyn, have you figured out what your major is going to be yet?" "Mister Denny, are you wearing makeup?" It wasn't a question, it was a challenge. Her brown eyes watched him without flinching, waiting to see how he'd respond. The question was so unexpected, it knifed...

The Slave and the Sissy Ch. 04

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Slave kissed Pepper's pretty face to reassure her before they were both shackled and then gagged, and sat on a prominent open seat on Ayesha's carriage, their hands bound in front of them; Ayesha loved to display her power and ownership of slaves, and would always ensure other people were made aware of it, even if the chattels were only hers to borrow. Slave...

Penetrated by a Woman

by Xavier_271 on Sep 12, 2017
BDSM

With a smirk she forces a ball gag into my mouth and secures my wrists and ankles tightly in restraints that are anchored between the doorframe and door in such a way that I am entirely helpless and exposed. I am a 23-year-old lean, athletic, blond-haired male who is going to school in Boston. I have been interested in bondage and submission for some time, a...

Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

Broken & Humbled

by jabberwok on Sep 13, 2017
BDSM

It all started a couple of years ago. The stress from work, and my recent divorce was wearing on my nerves. My overtime doubled, making my work days 12 hours, 7 days a week. The stress built daily, deadlines, etc. Finally it all came to a head. I showed up for work and started crying uncontrollably. Then I began to hysterically throw my paperwork all over. I...

After Church Ch. 03

by alien_freak_nugget on Feb 12, 2019
Transgender & Crossdressers

"Feels tight," said the gruff voice behind me. I felt a very large thumb plow into my ruined asshole and push down on my prostate. "You sure you been fuck'n this little sissy cumdump? You ain't just been fingerbang'n the little fag and jerking off in her mouth, have you?" "Sheeit," I heard Mike say. "I been tear'n the hell out of it for a while now. I just...

Close Shave

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

My sister, Sharon caught me naked, shaving my legs in the family bathroom. 'I thought you where in Court all afternoon.' I cried dropping the razor in surprise. My sister dressed in her smart black skirt, white blouse and black fitted jacket raised an arched eyebrow patronisingly. 'Obviously so, brother dear but my case finished early. I wasn't required f...

Neighbourhood Terror to Sissy Pt. 03

by Fibaro on Mar 26, 2019
Transgender & Crossdressers

(Hey, so things have been a bit busy lately, but I'm back with another part. I really hope you guys like what I have done with this and as always comments are really appreciated, enjoy.) ***** Mark woke up to the sound of his alarm with a loud groan. Taking the bus down town would take a lot of time and he had pretty much made up his mind that he couldn't...

Neighbourhood Terror to Sissy Pt. 05

by Fibaro on Apr 3, 2019
Transgender & Crossdressers

At least he didn't have to wait long for his bus to pull up. Not that it helped with any of his suffering. He vowed right there that he would never visit that store again. There were few people on the bus and yet he felt like all eyes were on him. Passing two girls his age at front he heard some whispers. "What the fuck, I never thought that store would ever...