Sissy Dildo Stories

41,035 results
Orientation
Length
Source
Infinite Scroll

Tied and Teased

by sugarRae on Sep 12, 2017
BDSM

Edited by Naughty Mike (what would I do without you?) And thanks to all my male fans, you've been so much fun and such an inspiration, whether you knew it or not. xoxoxo After my long-awaited graduation from Hamner College, Duane and I, for reasons I find myself somewhat at a loss to explain now, but it may have had to do with large quantities of fermented...

Bennie the Cuckold Ch. 02

by AfricanWriter on Aug 31, 2017
Fetish

Please read Bennie The Cuckold before reading this as it will not make sense. This is a cuckold story, the kind where the husbands finds pleasure in watching his wife getting laid by another man. I beg you not to read and comment if you are not into this kind of story. Just go read a plain vanilla story where people just have sex end of story. NB: I am fro...

Sex Change for Black Boyfriend

by watersoda on Sep 14, 2017
Transsexuals & Crossdressers

I have an interesting story. I am now 26 years old. I was born a male but at the age of 23 I had a full sex change at the request of my boyfriend. Here is how and why it happened. I knew I liked men from an early age. I was interested to talk with girls and be their friend but I wanted men. I looked at men in the street, at their muscles and their penile bu...

Magic Panties Ch. 04

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! Shall I do another recap? For some reason a magical pair of panties fell into my possession, me, bein...

Mom's in Town Ch. 24

by 1sfshermale on Jul 10, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** Brianna, with her gurl friend/roommate beside her, make their way into the hotel. She sees Juan, last night's doorman, again on duty and notices a glint of recognition in his eyes. "Evening ladies. Welcome back. You look lovely tonight." he offers with a smile directly at Brianna....

Serving the Dark Lady Ch. 02

by Certeis on Mar 5, 2018
Sci-Fi & Fantasy

NOTE: So halfway through writing this, I sort of realized that the way I've been pronouncing 'Aasi' as a shortform of Aasimar actually sounds close to sissy. Intentional? Who knows! ***** Lan took Karee... to the same pub he'd been at last night? It was noon so it was pretty much empty, but the bartender was still there. "You gonna keep him outta trouble...

Dr. Landry and Nurse Lisa

by newfield1981 on Apr 17, 2018
Transsexuals & Crossdressers

This story is a spin-off from the "Neighbors sissy son" series. Though it stands alone, it will eventually cross over with NSS. SPOILER This series falls in the transsexual crossdresser category for the first story. There will be very little in the way of men participating in gay sex. This series will sometimes revisit this subject. After that it will be ba...

Secret Lives Pt. 02

by WildDaisy85 on Dec 16, 2017
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 1. I highly suggest reading that first as it sets the stage for this. As requested by a reader on Pt 1, I have combined two chapters into this one to provide more length. I appreciate the feedback and please keep it coming. *********** I laid in my bed, dressed in women's lingerie and completely bound, as my siste...

The Intern Ch. 02

by FrostShard on Sep 14, 2017
BDSM

I didn't see Mengxia again for the rest of the day. That didn't mean she wasn't on my mind though. In fact, I thought of little else all day, and found it really hard to work. Towards the evening, I received a Snapchat from her captioned "Missing me?" showing a low selfie of her face, her full lips and the top of her cleavage. It got worse a few seconds lat...

The Party Game

by talthar on Sep 17, 2017
BDSM

I knelt beside the tub and waited for my Mistress's command. She laid back in the soapy water, surrounded by a cloud of steam, her long black hair flowing out around her. "Washcloth, maid," she said, and I immediately handed her a blood red cloth. As she washed her legs she looked at me with a grin. "Are you ready for the party tonight?" she asked. "Oh, yes...