Wife Sissy Stories

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Infinite Scroll

Caught Erect in the Greek Shop

by SissyChazzy on May 1, 2018
Fetish

My wife and I took a vacation from Canada to Greece one summer. It was really lovely. Nude beaches and beautiful waters. On one of the Islands, we headed into town to do some shopping. And here's where it happened. I was standing in the Greek souvenir shop, looking at the little figurines, when I came across the naked section. Greek men with hard dicks were...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

A Weekend Away Ch. 01

by SluttyChrissy on Sep 21, 2020
Transgender & Crossdressers

My wife Tiffany had been hinting for a while about my birthday surprise. She wasn't great at keeping secrets, and I normally figured out her surprises in advance only to have to act surprised, but this time she was being super cagey. She asked if I would be able to leave work at noon that coming Friday so I figured we were going out of town for the long week...

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

Becoming Her Bitch

by HerLittlePiggy on Sep 13, 2017
BDSM

"Take it like a man you sissy bitch," Jennifer said as she thrust her big strap on into my ass. "Yes mistress," I groaned as the long life like dick pounded my prostate. "I'm not your fucking mistress you sissy pig," my wife yelled as she slapped my ass hard leaving it stinging and red. "A mistress wouldn't have her cock inside your sissy ass. From now on...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

Sissy_World 02

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

John Maxwell hummed under his breath as he wiped down the counter tops of the kitchen, cleaning up before his Husband got home. Dinner was ready and waiting on the stove for her whenever she got home from work. He was petite, standing at four foot five, and slender though lightly toned. He had long ash blond hair that fell past his well rounded, juicy ass a...

Happy Marriage Ch. 02

by yesplease8 on Sep 25, 2017
Loving Wives

Well, our marriage just keeps getting better. My wife and I love that I'm submissive and that I was bi-curious. I say I was bi-curious, because my wife set me up to realize I am truly bisexual. After begging her to use me like a sissy slut with a strap on, she not only treated me like a slut with her strap on, she happily watched me with another man. She se...