Sissy Plug Stories

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Clara Bow's Academy for Ladies Ch. 02

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

The new sissy stood barefoot; naked but for the soft white gown. Though bewildered and a little scared, her little cock poked forward in the gown, partly through fear and partly through excitement as she felt the eyes of the stern woman upon her. Clara Bow rose slowly from the leather chair she sat in, cane in one hand, she wagged a finger summoning Pepper f...

Meeting Miss Kate

by princess_nicole on Sep 16, 2017
Transsexuals & Crossdressers

been reading on this site a lot, my Mistress had me write a story of my own for Her, and i thought i'd post here. it's my first attempt, i know it's not terribly long, but hopefully some of Y/you will like it. ---------------------- i had been talking with my new Mistress online and via text message for about a month and a half now. my first Mistress reall...

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

Another Submissive Slut Ch. 08

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I had hurried home from the porn shop only to run into Derrick in the lobby of the building. Lucky for me his mother emerged from a hallway and he could only cast me evil looks. His mother however took the opportunity to lay into me about my behavior and image. I realized as I slunk away from the verbal abuse that the chain around my waist was probably visib...

Aficionado Gets in Trouble Ch. 04

by His_fag_wife on Mar 17, 2020
Transgender & Crossdressers

Taryn told me to sit down, which I did with difficulty as I was only just getting used to breathing with the corset on. She knelt down in front of me, but this time it had no hint of submission. She was plainly completely in charge of me at this moment. She took the first shoe off, and prepared the first stocking, rolling it over her thumbs. I put my foot o...

AliExpress and Sissy Downfall Pt. 10

by His_fag_wife on Jan 23, 2019
Transgender & Crossdressers

As Charlie with her head raised off the cushion admired her new sissy pussy, she felt a complete head rush. As she and Tim had discussed just one guiche piercing at such length, over and over, texts flying back and forth on the crest of a wave of horniness and a submissives deep desire to please, she had fixated on the idea of being pierced without her wife...

Another Submissive Slut Ch. 09

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

As I watched Teddy perform I absent mindedly sucked gently on the stiffing cock in my mouth. My head rested on the fat owners hairy gut as I nestled between his thighs. His hands stroked my hair and body leaving me tingling with arousal. My drug addled body quivered with anticipation as I hummed my building passion over the rigid man cock. Teddy was eying...

Sissy Awakening Ch. 03

by Torbjornson on Oct 5, 2020
Transgender & Crossdressers

Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant I'd have to go outside. It wa...

Neighbourhood Terror to Sissy Pt. 24

by Fibaro on Sep 14, 2020
Transgender & Crossdressers

Chapter 26 Marcy was a nerve wreck walking out in public dressed as she was carrying the big pink bags stuffed to the brink. The street was relatively calm yet coming out of the outrageous store with those bags she instantly drew everyone's attention. The bus stop was right outside the store and yet those few steps towards it were the most embarrassing step...

Slut for All Pt. 04

by Knightofround on Sep 26, 2017
BDSM

Two weeks after Greg and Maggie came over, Vikki had to go away for a few days for a business meeting. I was a little upset because I had gotten used to being around her all the time. I was also going to miss the amazing sex. We both agreed to no self pleasure during the break. It was going to be very tough and I needed some serious distraction so I headed t...