Sissys First Time Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

You're Like a Little Boy at Times Ch. 03

by Myneed on Aug 30, 2017
Fetish

This is a slight twisted femdom love story that will make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** My heart ached for Mel. It had been another long week another long week of edging and chastity at Mel's instruction. Th...

You're Like a Little Boy at Times Ch. 02

by Myneed on Sep 13, 2017
Fetish

This is the continuation of a slightly twisted femdom love story that make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** It was a long week for me. I wasn't surprised when Mel didn't call. It made sense that we needed some t...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Orc Dominance in Elvenar

by AndrewStories on Mar 9, 2020
NonHuman

For over a thousand year the elven people on the island Elvenar has with magical power first spawned and then ruled over the orc clan. The elf used and abused the orc race strength to mine magical crystals for their own benefit. The new Orc chieftain Grog has since last years negotiations continued mining but also found a new demonic ally with lustful magica...

Elizabeth's Confession Pt. 04

by georgekaplan on Jun 4, 2019
Mature

I left the hotel around 5:30 am, having serviced with cunt & mouth three of the night boys. All paid me 100 euros. In financial terms, my first night as a whore had been excellent. My meeting with my very estranged husband less so. Why was I married to the only straight man who didn't want to fuck me? Still onwards as they say... On the down side I had not f...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

It's Only Fair Ch. 03

by Vanadorn on Sep 14, 2017
Loving Wives

Continuing the tale. I am pretty sure I took care of the "too damn short" problem, so from this point on, all submissions should be that length or longer (as merited). A word about descriptions - I like them. That's about it. I call it "front loading": if I set the stage as complete as possible, adding what descriptions I can it frees me up from ever havin...

Katt's New Toy Ch. 01

by econut on Sep 11, 2018
BDSM

SMACK! Katt's hand came down swiftly, squarely hitting her target. A muffled wail emanated from beneath her buttocks as the body of her subject bucked, his legs spasming in front of her. Katt smiled and laughed openly. She was truly enjoying herself. Ostensibly, she was punishing her slave for cumming without permission, but truthfully, she just really like...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...