Cuckold Sissy Maid Stories

25,992 results
Orientation
Length
Source
Infinite Scroll

A Year Ago Ch. 19

by MadQuill on Dec 18, 2018
Transgender & Crossdressers

The arc of this story will continue, but the timing may not suit some readers. After the two-year Sara's world is a bit clearer. Her relationship with Angelica and Jenn, has de-evolved. Cynthia had been pursuing Sara; she was patient, and she felt comfortable with the idea that Sara's libidinous behavior, with other women, might bring Sara back to her. Afte...

The Fate of Her Lovers

by BigK10 on Sep 15, 2017
Loving Wives

Chapter 1 My wife, Juanita, set across the breakfast table from me, just as we had for the last twenty-four years of our married life. It was a Thursday morning in late September and the leaves of the trees in our backyard had begun to turn various shades of yellow and tan. She was enjoying that view through the window of our breakfast nook, while I read th...

Summer Hire Ch. 05

by brentaden on Sep 11, 2017
BDSM

Decision "So we didn't say anything more. We got back to his house, and I didn't really say goodbye or anything. I just kept on walking up to where I'd left my car and drove away." Melissa looked up from her unfinished bottle of beer, which had grown warm while she told Malcolm about her day with Erik. Shame and sadness tempered her voice. She did feel a li...

The Werewolf's Sabbat Ch. 02

by River_willow76 on Sep 25, 2017
NonHuman

"Daddy, Daddy!" Cynthia squealed when she spotted him outside of the school. Running late, Bill had just arrived in front of the school. He smiled and waved at his little girl. She ran as quickly as her short legs would carry her, and he reached out and scooped her up in a big hug. "Hey there, ladybug!" He hugged her tightly, swinging her in circles. "I'm so...

Black on Black Pegging is Okay

by Samuelx on Sep 11, 2017
Erotic Couplings

Romulus Stephen sat in his bedroom in the small apartment overlooking The Park in Vanier, around the eastern bend of metropolitan Ottawa, Province of Ontario. The big and tall young Black man sat at the computer with his pants down, and furiously stroked his dick. On screen, a sexy Black woman was banging a slim White guy in the ass with her strap-on dildo....

Caught and Used

by rayd9 on Sep 18, 2017
Transsexuals & Crossdressers

I am a secret, heterosexual panty boy, that loves to dress up in my wife's lingerie when she is not around. My wife and I have two mutual friends named Mike and Mandy. Mike and Mandy had things stored in our garage while they moved. Well my wife had to go away for a day seminar for her company, and I had the day off. I have been looking forward to this day f...

Mistress Marisa's Estate Pt. 20

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** I am standing in front of you wearing sissy-like cute little heels. That and the permanent gold ring you had put in place...

Pretty in Pink Ch. 03

by jealouscuck on Sep 18, 2017
Transsexuals & Crossdressers

After our trip out of town, Jessica and I had an even better sex life, if that was even possible. One night we ate out as man and wife and she made me stop at a dark, lover's lane type place. I had not really noticed before, but she had dressed rather conservatively. I just assumed that it was some of her new work clothes. When we got parked, she said, "Oh,...

Alternate Reality Ch. 02

by grgy56 on Sep 12, 2017
Transsexuals & Crossdressers

"Shit! Shit! Shit!" I screamed to myself. "How the fuck am I supposed to get out of here?" I am stuck in a virtual reality scene. I am my avatar, Krystal. The developers of SIM: Slut City offered to me a try-out of their new VR body suit. After putting it on I was completely engulfed and only aware of my life-like surroundings within the game. Unfortunately...

Bad, Bad, Boy

by AfroerotiK on Sep 16, 2017
BDSM

Working for an advertising agency has its advantages. At the drop of a hat, for barely any reason at all, there's cause for an after work get together with free-flowing drinks for all. On this particular Friday evening, there was reason for celebration because Michael Shield's company signed a major client and glasses were being raised all around Schmidt's B...