Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

The Holiday

by Lord_Overload on Sep 12, 2017
BDSM

PART ONE It was a warm morning in late summer; Stef and Kayleigh were lying naked, bar their collars, on the sofas in the conservatory, enjoying the warmth of the rising sun. They looked over Exmoor, wondering what the day would hold. The two girls heard a noise and turned to see their Master, he was carrying a number of suitcases. "Morning Girls" He said...

i am Kevsfrannie

by Kevsfrannie on Sep 17, 2017
BDSM

i am Kev's frannie, forever bound to the Woman who has both blessed -- and cursed - me with my unique fate. Part 1 i first met my Keverly more than 25 years ago, when i became Her boss at our work. As a professional, i had strong boundaries about appropriate workplace relationships, so for a year and a half i was unwilling to recognize what was otherwise o...

Results of the New Arrangement

by justincbenedict on Sep 17, 2017
BDSM

God, I couldn't believe it, here I was, tied up with my erection poking through the plastic ring...and Daphne was tease-torturing me as I clutched the string to the plastic ring in my mouth...oh God. The door opened, and Master Tanner came in behind her, brandishing a pair of children's scissors that he'd borrowed from my son's room. Playfully, Tanner ran th...

Tommy Awakens Ch. 12-15

by HotTommy777 on Aug 30, 2017
Group Sex

Chapter Twelve -- Ralph and Friends Sarah hung up the phone after talking to the manager at Taco Bell. "Steph works today from 3 to 11," she said. "Well, let's go over there about 6 and surprise her," I responded. We had already discussed bringing Steph keys to the house and the Mustang if she really showed up to work for a week. A few hours later we drov...

Panty Consequences No. 03

by PantiesAndPies on Sep 14, 2017
Fetish

This series of stories are all standalone so can be read in any sequence. They are about my favourite fantasy --- my first time wearing, or first time being caught wearing panties. Obviously then they all involve lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men amongst other things. If any of these are lik...

Are You Gay Ch. 01

by Scribler on Sep 12, 2017
Transsexuals & Crossdressers

Are you gay? They were three simple words that could drive a man into a rage. It was a question on your manhood and on how others around you viewed you. Just that question in the eye of your lover, boss or a family member could cause enormous heartaches and sometimes, physical pain. I feared that question mostly because I was perceived as gay on many occas...

Bigger and Better for Gwen

by donaldelliott11 on Apr 14, 2020
Loving Wives

With the help and consent of smallercuck, who wrote a version of Chapter 1 years ago and didn't continue. He invited me to take Gwen's story further, and has seen and endorsed this completion of his original work. ***** Chapter 1 "I noticed that Darren joined the gym." Gwen looked up from her papers as the young salesman walked into her office. As Assist...

Kylie Goes Back to School

by Noj on Oct 22, 2019
Celebrities & Fan Fiction

This story follows on from the story "Kylie's Latest Squeeze, which I recommend reading prior to this. This story is contains adult material and is only suitable for people over the age of 18. This is in no way connected with the subject. Don't use this without my permission. Now, on with the story! * After leaving Kylie's services as an assistant, she ha...

The Last Boy Scout Ch. 04

by Tx Tall Tales on Nov 4, 2019
Group Sex

====================== Sisters, Teacher and Best Friend. Jealous? Sometimes, I'm a big ol' idiot. I don't use an editor often enough, but MarieWriter helped with this series, and it's considerably better for her assistance. I should have mentioned that in the first chapter, where she provided a lot of insightful advice. Of course, I'm never happy with the...

Born to Be Ch. 07

by DamienDeath20 on Jun 8, 2020
Transgender & Crossdressers

A.N. Return to the strap on! If this isn't my favorite chapter so far, it's definitely one of my favorites x))) Buuuut chapter 8 is preeeetty awesome too ;D I know I'm a whore. The Following Contains: Interracial between a tall black lady and a crossdressing femboy. Which in conclusion creates a formula of strap on penis being inserted into femboy bott...