Sissy Lingerie Stories

30,229 results
Orientation
Length
Source
Infinite Scroll

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

A Natural Sissy Ch. 05

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justify it. Ch. 05 Stacy's Interlude "Hi, guys. I'm Stacy, and I guess you know...

What a Night

by Anoun_Ymous on Sep 17, 2017
BDSM

It all started out innocent enough...here I was laying in bed next to my wife on this cold winters night, just two nights before Christmas. We had arrived on time to her parent’s house with nothing unusual happening on the way. It had been a pretty dull night and with her parents having gone to bed the two of us and her younger sister had decided to get comf...

It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...

Sissy Dreams Ch. 01

by SissyJane on Sep 13, 2017
Transsexuals & Crossdressers

I wake slowly, lazily, in a soft fog of deep relaxation. A slight shift of my body reminds me of the satin lingerie that swaths my body in sissidom. I wait for you. I feel the brush of something, cloth, no satin. Flittering over my skin like a drizzle of wax leaving me on fire. It moves like snake and slithers over me, making me shiver in a fever. It finds...

Helping Jess Pt. 04

by mski on Sep 25, 2017
BDSM

I got into the house. Jess looked into my eyes and saw I was out of it. "I guess that was quite hard for you John, maybe too much too quickly." I nodded. My head was screwed, I didn't really know where I was. She gave me a kiss on the lips. "OK sleepy head. Let's get to bed. Up the stairs with you, and brush your teeth!" She watched me walk up, then cat-...

Jamie's Descent Pt. 02

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

'That's it, baby,' Vanessa purred as she snaked her hips forwards and back, gently sliding the strapon in and out of my mouth. I could no longer think rationally, as any self control I still had slipped away and trance like, my eyes closed, I sucked the rubber phallus in and out of my lips. 'Baby, you love this don't you?' Vanessa's voice took on a hypnoti...

Aunty's Toys Ch. 01

by novelcriss on Aug 21, 2018
Fetish

Simon rang the door bell, prompt at 2 pm, somewhere between nervous and excited and wondered quite how he had reached this point. He had met Sally in, of all places, a crowded cafe at King's Cross when all the trains were late. She'd pulled up a stool next to him , asked if it was okay to sit and started chatting. She was so easy to talk to, middle aged, n...

Becoming a Sissy Maid & Slut Vol. 06

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Twelve: Chantel's day off. Ohhh, and ahhh as I awake and stretch in my bed. Mmm a blissful sleep where I see the clock and that it's actually 10:00am. At first I freak out a little bit as it normally would be very late for me. But I soon realize Master has allowed me a blissful and free Sunday off. I then get out of bed, my butthole is sore from the...

Sara Shows Her New Man Self Love

by Sexy_SaraCD on Sep 13, 2017
Transsexuals & Crossdressers

I felt vulnerable for the first time as Sara and while part of me was nervous, almost hesitant, the other part of me was exhilarated. I felt nothing more than curiosity as I faced an unknown scenario and what it would lead to. I met Daniel much like I've met most of the men I did as Sara. Except this wasn't a post of mine on Craigslist. This was his post a...