Sissy Truth Or Dare Stories

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High Society Sissy

by beyondkink on Sep 11, 2017
Transsexuals & Crossdressers

I guess I can say I was one of the lucky ones. Fresh out of an ivy league school with a degree we were met with two different tales. "Sorry, you're over qualified," they said. Or we would hear, "We're looking for someone with more experience." An alum that I had befriend however was able to land me a waiter position in a posh New York country club that ca...

Submitting to the Neighbour Lady

by Stillherer on Jun 8, 2020
BDSM

I went to high school with the Post twins in the late 60's. Tommy and Belinda Post. The Post twins were new to our area and it was rumoured that their father wasn't with them. It was our senior year and being 18 we just wanted it over with so we could get on with being adults. Belinda never gave me a second look but before he knew better Tommy struck up a te...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

My Wife Takes Me Much Farther

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been three weeks since my wife turned me out at her book club and turned me into a cumslut. That event seems to have really opened up my wife's imagination and made her hunger for more dominance over me. For the last three weeks, she's kept me locked in chastity, even though our deal was that I would be released after the event. She's also made me kee...

A Mistress to Obey Ch. 05

by gbr2004 on Sep 12, 2017
BDSM

Continuation of this story that involves forced fem, forced bi, discipline, humiliation and submission. Not your thing, move on to another story. * We got back to her house and she opened the car door and let me out. I followed her into the house and she went and set down in her chair and I just stood there in front of her. 'Present sissy boy.' I droppe...

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

Young Master Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a ch...

Truth or Dare Takes a Turn Pt. 04

by Cutiepie183 on Sep 28, 2020
Transgender & Crossdressers

The next morning I wake up at around 6 and find a note on my chair and an outfit on the floor in front of me, I also notice my gag has been taken out. It hasn't fallen out though because it's nowhere around me. The note on the chair simply reads. 'Big day today, get dressed, cook breakfast then wake me up with some service with a smile.' Not entirely sure wh...

Textual Relations

by Pattyssissybitch on Sep 17, 2017
BDSM

PART I -- FRIDAY NIGHT My wife Patty had to go to Los Angeles for a weekend company annual retreat. When I dropped her off at the airport on Friday morning, she told me she had a surprise for me, and left it at that. I wondered all day what she was up to, and I had to wait until almost 4 in the afternoon to hear from her. When she called to tell me she'd ar...

Hubby Drop To Thy Knees! Ch. 01

by Ashesh9 on Sep 17, 2017
BDSM

CH1. : HUSBAND, DROP TO THY KNEES!!! IMMEDIATELY! "Husband drop to thy knees!!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!!! The vast assemblage...