Dildo Sissy Stories

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Orientation
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Infinite Scroll

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

Mistress Kia Versus Samuel X!

by Samuelx on Sep 17, 2017
BDSM

For over two years now, the bisexual Haitian-American male known as Samuel Xavier had been pleading with his tall, curvy and sexy African-American dominatrix, Kia Holbrook, also known as Mistress Kia or simply Lady K, to turn him into a submissive Sissy slut like he was born to. For the dominant Black woman, doing something this drastic to a Black man wasn't...

Miss Jennifer Fucks Little Tiffie

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

The Saturday after Miss Jennifer had her boyfriend fuck my pussy/bottom, she called to me while I was doing her laundry and told me to come to her room. As I entered, she told me to come and stand in front of her, where she was lying on her bed. I was, of course, dressed like a proper little housewife, with my pink lace bra stuffed with my big 54DD falsies...

Teased, Denied and Sissified Ch. 01

by subbieman on Sep 11, 2017
BDSM

My girlfriend and I had been dating for nearly nine months when we decided to move in together. Her lease was expiring so it made sense as we had grown closer and she really seemed like "the one." We got along great and I loved her, but, to be honest, our sex lives had recently been lagging. I hoped that moving in together might rejuvenate it, but, based on...

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...

Caught in Panties & Dominated Ch. 04

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Tracy -- me Tracey -- me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate My ass was so sore. But he hadn't fucked me. Not yet... Earlier that night Rick made me his bitch. He took my sissy, lipstick-painted mouth, with his cock. He'd commanded my mouth, and he'd fill...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Caught in Panties & Dominated Ch. 05

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Trace - me Tracy - me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...

Black Sissy For White Queen

by Samuelx on Sep 16, 2017
Interracial Love

I feel so damn great as I slide my strap-on dildo deep inside Ramon Jones. The six-foot-tall, skinny Black guy looks absolutely gorgeous in a bright pink dress, white pantyhose and high-heeled red shoes. His face is perfectly made up, rouged and his makeup and lipstick are applied nicely. The fuzzy black wig he's wearing only adds to his decidedly not so mas...