Sissy Baby Stories

124,889 results
Orientation
Length
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Infinite Scroll

Rebound Sissy

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

John had broken up with Angie, his girlfriend after what was like three years. They dated their first year of college then they moved in together and were serious for three years. And none of our friend circle saw the break up coming. And we sort of rallied around John as he tried to pick up his life. Which included going out and getting him to go out wit...

Kimmy's Discovery Ch. 03

by Deviana on Sep 16, 2017
Transsexuals & Crossdressers

i heard the click of my .. of Dougie's high heels and it was like everything fell silent. i walked around the kitchen, around and around, wanting to hear that click, to have the sound so deep in my mind. i took one of the VS 120s and then a pretty pink lighter that was on a side table- i have to find one of these for me- and lit the tip, feeling the filter e...

Doggy Style

by keptsissy on Sep 13, 2017
Fetish

I feel his middle finger slide up into my butt. He drives me crazy every time he does that. Each time is like the first time. It's the most erotic thing he does with me. It makes me hotter than when he fucks me, breeds me. I never get used to it. Every time he does this to me it's like the first time. He pushes his finger into me as far as it will go. He fe...

Owning The Girl Next Door

by Frognut on Sep 11, 2018
Sci-Fi & Fantasy

Chapter 1 The Beginning It started one afternoon after I had gotten off work with my Dad, I was tinkering with my car in the driveway when I hear my name being called. I looked down the street and a friend of mines girlfriend was walking to me, I said hey Sherry what's up? she asked what I was doing tonight? I said going to cruse the beach for a couple...

Suspected Affair - Confirmed

by 69Jance on Jun 1, 2020
Transgender & Crossdressers

Second Part of Suspected Affair After confirming my suspicions, I was looking forward to seeing what was next with a hot wife and a pair of handsome twins. Actually though, from what Maxwell said, they all were looking forward to bringing me out of the proverbial closet and see what is next for their new sissy. Maxwell had said "We should go meet Heather a...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

Another Submissive Slut Ch. 06

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

As I stared transfixed as Ms Shawna rose off of Mr Lennie's drug rigid cock. His dick was shiny slick with a mixture of their cum, the goo thick about the folds of Her twat. "Oh god Lennie," She gasped breathlessly, "where do You get all Your beautiful cum from." I groaned involuntarily as a cum gushed from within Her to slip down Her inner thigh, while Mr...