Bondage Sissy Stories

20,137 results
Orientation
Length
Source
Infinite Scroll

Truth or Dare Takes a Turn Pt. 06

by Cutiepie183 on Nov 2, 2020
BDSM

I wake up in a small strange concrete room, still wearing the pink latex that Master Brent bought for me but this time without the hood or the gag. I look down and see masters foot on the concrete floor tapping. As I look further up I see his tall muscular body dressed in tight leather and the big smirk on his face as he says "well looks like our little bitc...

Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

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The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Covid 19 - Pete Turned into Charleigh Pt. 02

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

Again it was as though she'd slapped him back into reality, just as she intended, she'd noted his angry response earlier that day and wanted to trigger him again, but trigger him much more this time. She simply would not accept rudeness or attitude from him. Pete had to realize that as Charleigh took over his psyche, that she would need to be more and more s...

Wife in Control Ch. 08

by wifetoy on Sep 25, 2017
Fetish

This is the eighth and final chapter of my wife's fulfillment of the punishment poem offering humiliating punishments to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I adore and cherish my beautiful wife. She not only tells me how much...

At Their Mercy

by Subserver on Nov 9, 2017
BDSM

Miss Erin and Miss Erika giggled and teased, pinched and fondled me as they made me into their feminized plaything. When they had finished I was wearing a short blonde wig, eye and face makeup, red lip gloss, red nail polish on my fingers and toes, small hoop earrings, perfume and black satin panties with lace insets, a matching bra that was filled with fal...

Appointment by Card Only Ch. 06

by Sputnik57 on Sep 17, 2017
BDSM

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he co...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Natalie Learns Her Place

by natalieukcd on Oct 6, 2020
Transgender & Crossdressers

I had been fucked and i had loved it. I especially loved knowing that i had the female role instead of the male role, which was the normal one for me, historically. I loved being "beneath". I loved being the weaker of the two people. I loved being the repository instead of the one giving. I just loved the feelings of horniness and desire and need and then o...

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...