Sissy Lingerie Stories

30,229 results
Orientation
Length
Source
Infinite Scroll

Finally Found Her Ch. 02

by hyperpress on Aug 18, 2017
Fetish

Switching from "you" to "she" for effect. She moved from the vanity chair to the bed. I've covered the bed with pillows and the room is lit with candles. "You're such a good little girl, now go get us a bottle of wine," she is lovely on the bed. I'm standing at the bedside and your mouth is irresistible and I bend at the waste to kiss you. Softly we kiss a...

Sissy's First Trip Out

by thinksissy on Dec 24, 2019
Transgender & Crossdressers

*This is my first story so please comment as much as possible to let me know what you think. Thank you!* Kenny had always been obsessed with women's underwear. It all started out pretty innocently, well, as innocently as can be expected when masturbation is involved. He used to look through women's fashion catalogues and drool over the lingerie and bikini s...

Sorry Sissy You Lose Pt. 04

by LittleDickSissy on Apr 10, 2019
Fetish

Slave had been busy. Spending hours looking online for things for his Mistress. His little dick always swelling and throbbing as he went through pages of web sites, looking at heels, lingerie, hose, dresses, jewelry, etc. Mistress had tasked her slave. He was to purchase various outfits for her to wear on an upcoming trip. A work trip for his Mistress, but h...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...

Khan Market Sissy

by smalltownsissy on Dec 24, 2019
Transgender & Crossdressers

An English degree was all that Lijo had when he took a train from Kochi to New Delhi. He was promised a teaching assistant's job at a University in Delhi. Though he knew that he could barely survive on the salary of a mere 16,000 rupees, Lijo still went ahead as he somehow wanted to leave behind his conservative hometown in Kerala and experience a metro life...

My Father, The Maid Ch. 02

by SissyOona on Oct 30, 2018
Transgender & Crossdressers

I awoke the next morning fairly early. My sleep had not been as restful as I would have hoped due to the revelations of the previous day. Eventually I pulled myself away from the supreme comfort of the bed and stumbled to the bathroom to take care of my morning business. As I exited the bathroom I could hear the sounds of breakfast being made from the kitche...

Wife Left Me so I Could be a Girl

by TammyPanty on Jul 10, 2018
Transsexuals & Crossdressers

I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with my mother until she unexpectedly passed away when I was 23 year...

Step by Step Sissification Ch. 01

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- It all star...

Getting Help Ch. 01

by azkelkel on Sep 16, 2017
Transsexuals & Crossdressers

I nervously sat in the waiting room for my 1:00 p.m. appointment with the therapist/psychologist. I found her through online searches, as I guess we do all things nowadays, where her credentials and location were most important to me. She received her various degrees from decent universities and chose to open up her practice in an area just far enough away f...

Caught by the Lodger

by SuzieR on Sep 13, 2017
Transsexuals & Crossdressers

Having split up with my girlfriend about six months before, I was getting a little bored of living on my own. I'm a 29 year old guy living in South London and I thought it would be a good idea to get a lodger. I had a spare room that was empty, the company would be good and the extra money would come in handy. I put an ad in the local newspaper and within a...