Sissy Stories Stories

63,614 results
Orientation
Length
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Infinite Scroll

Sissy Boy Secretary Ch. 08

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine knew that it was now time to implement her plan to bury her nearest competitor, Bill Andrews... You see Elaine's secretary arranged through the secretarial pool to make sure Tammy, the daughter from next door, got the job as Bill's secretary... As you already know Elaine has used Tammy's information to her advantage and now it seems that Bill was at h...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

This Cock Tastes Like My Wife Ch. 04

by Turned on Sep 17, 2017
BDSM

This is part 6 and 7 of the series. Parts 1-3 were contained in chapter one. Part 4 in chapter 2. Part 5 in chapter 3. Part 6 – The Battle Against Reality "Honey? Honey? Are you awake?" I cracked my eyes slightly, but pretended to still be asleep. DD was wearing red thong panties and a matching bra, checking herself in the mirror atop the dresser. She...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

Becoming Mindy Ch. 02

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Thank you for the positive feedback from my first story. As I recall things I wrote about in my diary, I am not going to be writing on all of them. Just the ones that are important to my story and/or just some memorable events (i.e. the first time I..). I hope I am able to write them in a way that you find as enjoyable reading as I had living them. I have se...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

What Every Sissy Knows

by BelissimaSissy on Jul 31, 2018
Transsexuals & Crossdressers

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy! ***** I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could he...

Aficionado Gets in Trouble Ch. 03

by His_fag_wife on Sep 23, 2019
Transgender & Crossdressers

As his WhatsApp call rang to the contact simply named Master, Pete had no idea what faced him. His senses were full of Marks cum, the distinctive metallic taste, it's manly musky aroma were overwhelming for him. He was still high from the poppers and thought he should just sit for a few minutes to recover a little, although the nearly full bottle of poppers...