Sissy Bra Stories

144,731 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Being a Sissy for Viv Ch. 06

by Caron on Oct 31, 2017
Transsexuals & Crossdressers

Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...

Sissy Panty Handjob

by CrossdresserCaitlyn on Jun 19, 2018
Transsexuals & Crossdressers

When I woke up in the morning I saw my girlfriend getting ready for work. She sees me awake and reaches out and rubs my penis outside my panties. While rubbing me she tells me if the house was spotless when she got home sissy would get a special treat tonight. She let's go of my dick, smiles and leaves for work. Still hard I jumped out of bed immediately a...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

Being a Sissy for Viv Ch. 04

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

With great care I slowly pulled the 10 denier black nylon stocking up my leg. I had other pairs, but these were my best and today it was important to have the best. Cautiously I rolled up the second one and with the same deliberation pulled it onto my other leg. The feeling, of soft nylon sliding over my naked skin exquisite and exciting as always, but today...

Behavior Modification Institute Ch. 05

by NancyPan on Sep 12, 2017
Fetish

"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you...

Being a Sissy for Viv Ch. 05

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

Mistress Viv wondered around the bed, filled with the most feminine and sissy items from my wardrobe. Her fingers stroking and examining various items in turn. The first things she picked up were some nylon panties. They were one of my earlier eBay purchases. A double layer of nylon ensured they always gave that nylon sliding on nylon feel even when worn on...

Discovered at the Bar

by CrossdresserCaitlyn on Mar 25, 2019
Transgender & Crossdressers

It was 9 pm on a Friday night and I was just getting off work. It was a long day of running meetings and I really needed a drink. I was out of town and didn't know anyone so I decided to go to the bar by myself. As I sit down at the bar I take off my suit coat, untuck my shirt and loosen my tie and ask the bartender for a Jack and Coke. The first drink did...

Being a Sissy for Viv Ch. 01

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I." "Oh, what was so interesting about it?" I asked. Viv paused for a moment, her eyes on the wine glass in her hands. "It was about turning men into maids....

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Mistress Commands Me in the Office Pt. 02

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Oh god, mistress, my dick is so hard in my panties now. At your command, in full view of the three vid-cams you made me install in my work cubicle, right here in the middle of my work day, with my associates working only feet away, on the other side of the cubical walls, you made me do it. Your commands, your training, your trigger words. My compliance. My s...