Sissy Prostitute Stories

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Infinite Scroll

Prisoners of Their Own Device Ch. 02

by Stardog Champion on Sep 3, 2017
Erotic Couplings

Alone in her trailer, a full month removed from her serendipitous soiree with Glen at the motel, Lana sat on her tattered and worn sofa, dreading the impending result of the wheels they had put into motion after having sex that morning. Invigorated, at the time, by a man who was willing to show her some attention, sexual and otherwise, Lana had poured her s...

Mistress Starla Proves Her Point

by justincbenedict on Apr 16, 2018
BDSM

Porky was weeping bitterly, and at the same time, his dick was straining, and quite excited. Who was this girl? Starla was his friend Spalding's cousin, and he'd seen how she enslaved him--Olivarius, the school's intramural lacrosse coach had told Porky that Starla had taught him how to suck his own dick... Several young women of Porky's acquaintance foll...

Mistress Sylvia Pt. 01

by corduroysissy on Dec 18, 2018
Transgender & Crossdressers

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergen...

The Hardest Kind To Be Ch. 04

by Joe Wordsworth on Sep 17, 2017
Exhibitionist & Voyeur

Hopefully, you've read the previous parts--as some of this won't make too much sense if you haven't. Either way, the cast is eighteen and I thrive on your love and affection. Vote me well, mon ami... vote me well. . . .. ... ..... The next morning was a hazy shade of warm beery tastes lingering in the back of Ginnie's mouth. She woke with a grumpy headache...

The Visitor Ch. 09

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

This is the continuation of the story of my foolish submission to an online Master, who actually became my visitor and all the things that happened as a result. It describes how I slid further and further under his control, by his use of drugs, heavy persuasion and as he is a doctor, the changes he made to my body to prevent my escape from him. This particu...

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

My New Daddy Ch. 07

by sissytoy20 on Mar 21, 2018
Transsexuals & Crossdressers

After Boss zipped up his freshly cleaned cock, glistening with my spit, he took me up to the 30th floor. My brain was still buzzing with my anal orgasm when he took my arm and basically forced me to walk out of the elevator. I stumbled on my heels beside him, reaching back to finger my cum-filled asscunt. I dug out some of Boss' load and licked it off my fin...

Maid to Rule

by KuroshioX on Sep 16, 2017
Transsexuals & Crossdressers

(Futa on male, futa on female, oral, anal, bondage, cuckold) Standing in front of the master bedroom's door, I realize it is times like this that are the sole reason the middle-aged couple hired me. I'm a mediocre cook, only passable at cleaning, barely have the patience to tutor the youngest child and am not pretty enough to be a trophy hire, but there is...

Mandingo Row Ch. 03 - Disguised

by scatwoman on Jul 6, 2020
Interracial Love

3. Disguised For the next several days, I walked funny and spoke with a raspy throat from the nightstick mouth-raping. Brittany didn't even notice. Or, if she did, she didn't care. What was worse was that I couldn't get an erection without it bringing up the memory of the whole incident with the two abusive officers. Any time I touched myself, the feeling...

Hazardous Waste Ch. 05

by NOIRTRASH on Sep 16, 2017
Loving Wives

All characters are adults. Reminder. This tale is noire, and noire is neither kind nor gentle nor uplifting. It's supposed to stun and sting and offend. ***** I got sick as shit one night so they tied my sixty-five year old ass up in a straight jacket and hockey mask, like I was Hannibal fucking Lector, and led me off to the infirmary with an armed escort...