Neighbourhood Terror To Sissy Stories

359,935 results
Orientation
Length
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Infinite Scroll

Property of Master Ajax Ch. 01

by TightandWhite on Sep 19, 2017
Transsexuals & Crossdressers

I headed down to the community swimming pool glancing furtively left and right to make sure no-one was around. It was midnight on a Tuesday so there shouldn't be, but I wanted to be sure. I clutched my bag tightly as I reached the changing rooms. To the left, the lady's and to the right, the men's. After glancing over my shoulder one last time and taking a d...

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

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...

Proud To Be A Sissy Ch. 06

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

It was still early and I wanted to enjoy the feeling of being dressed in my shear hose and garter belt, tiny g-string panties and matching bra and the form fitting shiny black mini dress that barely covered my stocking tops for as long as possible. So I spent some time doing some domestic chores and it amazed me that doing something so simple could make me f...

My Neighbour Queen George

by HorribleHenry on Oct 6, 2020
Transgender & Crossdressers

MY NEIGHBOUR QUEEN GEORGINA I suspected there was something fishy the first moment I met him. George that is. And it was the smell of him that gave me the clue; deliciously flowery perfume. I invited him in, as you would do when I with a new neighbour calls to introduce themself. He had picked a good time. I had just arrived in from work and was eyeing...

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...