Dildo Sissy Stories

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Orientation
Length
Source
Infinite Scroll

Working the Holidays Pt. 02

by es_larsson on Mar 9, 2020
Transgender & Crossdressers

My alarm woke me at 7am with an urgent beeping. Bleary eyed, I sat up in bed and swiped my phone screen to silence it. I clicked through the notifications, and within seconds was wide awake. A message from Kareem: "Don't let me down today babygirl. If you don't show up today I'll have no choice but to punish you." Disgusted, I threw the phone down on th...

The Dark Horde Pt. 05

by HalfAsleep on Mar 26, 2019
Sci-Fi & Fantasy

The young faun had led Valentine and Bear to the other side of the circle of pillows, where they now sat. Vegetables and fruits had been set out in front of them, some set on a small brass brazier to grill. From their position they could hear the discussion between Rom's inner circle, but were not part of it. Val nibbled on a roasted carrot, straining to h...

Experiment 239 Ch. 07

by AmethystMelange on Dec 2, 2019
BDSM

"Tony, may I please suck your cock?" Anthony put his newspaper down, glancing up in bemusement. Sure enough, before him stood Sophie, unsteady and shaking in her unforgiving ballet boots. A faint sheen of perspiration beaded on her forehead, a most pleasing display of the toll the exertion was taking on her. Her green eyes were wide and pleading, and she ha...

Sam's Spa Chronicles Ch. 04

by BADSAM689 on Sep 19, 2017
BDSM

Monday morning Elizabeth Ann wakes up early. She throws the covers off herself and looks at her tanned, naked body. Her dark nipples rise like twin towers in the center of chocolate cookies resting on amber orbs. Her waist is narrow; it's flatness broken only by her navel, which appears as a sensuous hollow that longs to be filled with syrupy cream. Her Ven...

Chastity Resort Pt. 06

by handyrandy9 on Sep 25, 2017
Fetish

This is a continuation of a multi-part story. If you don't start with part #1, none of this will make sense. ***** I awoke to what felt like something poking into my lower stomach area. As I groggily opened my eyes it took me a moment to figure out what was happening. My wife was kneeling on the bed beside me, leaning over my--oh shit!! I had forgotten I...

Ok I'll do It, Again Pt. 06

by ozinsom77 on Sep 18, 2017
Novels and Novellas

Time for Getting Down to Business Having arrived back to their little unit, the first few days went by catching up with all events since they went on their honeymoon. All their friends wanted to meet to have drinks, dinner, tell them how gorgeous the resort was, the lifestyle, the shopping and the surf, sand and sex. The food, the marihuana and those huge b...

Summer Heat Continues 03

by marriedheat on Nov 22, 2017
Group Sex

Heather kissed my cheek, patted my ass, and said, "See ya in a bit. Love ya, sleepy head." I wearily opened an eye and grunted something undecipherable. I rolled over and looked at the clock. "11:35? What the hell? How did I sleep this late? "Where you goin'?" I stammered as I lazily stretched my sleepy arms and legs. "I'm meeting a few friends for lun...

Ginny's Humiliation Pt. 02

by Gln1517 on Jan 5, 2018
BDSM

You should read Part One before starting this part. Again, thanks to Rman for his contributions and many ideas. They are greatly appreciated and enjoyed. * "Mike, if Ginny decides to sell herself at auction again, we talked about making the auction more entertaining in order to draw interest from the members." Jonathan said as they walked out from Connie's...

The Tempest is Thy Namesake Pt. 01

by SandyMarl on Jul 13, 2020
Toys & Masturbation

Author's Note: Welcome randy reader. I am honored that you have selected my story. I have written 'The Tempest is Thy Namesake' in three parts, covering the expanding sexual explorations and experiences of Wendy Rains. I believe that each part reads well enough as a stand-alone story. So, if you are here for the wet and juicy exploratory masturbation exper...

Wives of The Commander Ch. 06

by MTL17 on Sep 24, 2019
Celebrities & Fan Fiction

Disclaimer: I do not own The 100. I do not make any money from the writing of this story. ****** “Let her win.” Lexa softly but firmly ordered. Clarke linked a few times, unable to believe what she just heard, and then she frowned, “What?” “Clarke, you know I hate to repeat myself.” Lexa reminded her, before sighing and indulging her wife, “You should le...