Wearing A Bra All Day Literotica Stories

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Caught For the Last Time Ch. 03

by TGJamie on Sep 12, 2017
Transsexuals & Crossdressers

So one evening while watching TV, she was sitting there sifting through catalogs and mailers. As she tossed another one on the floor she asked "Have you noticed how many sales there are on lingerie at the different stores right now?" Trying to be oblivious, I said "Not really, they always seem to have sales." But I said to myself, heck, I've noticed all my...

Three's a Circle, Not a Triangle Ch. 11

by SusanJillParker on Sep 25, 2017
Fetish

Susan models her panties, bras, and shoes for William and Liz. Susan unbuttoned her blouse in the same exact, practiced way as she's done so very many times before and William stared at her as if seeing her cleavage and bra for the first time. Even though he's seen her tits so many times before, with her long line of cleavage and bulbous breasts swelling ou...

CD Internship Ch. 04 Conf. & Class

by cdtycoon on Mar 24, 2020
Transgender & Crossdressers

All the characters in this story are above 18 by age, so read and enjoy it till I get to the next stage. WEEK-LONG FULLTIME FEMALE On Tuesday; I woke up at 5:00 a.m. and took a nice hot bath to avoid getting myself cold. Then coming out tucking a towel on my chest I look for dad but, he was already out for his walk. So, I went to my room and wore my padded...

Braless Is Better

by CQtRose on Sep 16, 2017
Reviews & Essays

Not wearing a bra... braless... letting the puppies (or kittens, in my case) play freely. Yes, when I went to the grocery store this morning, I didn't bother strapping the girls into anything that would restrict their natural movement. Shopping at the mall? Nope. Church last Sunday? Sorry, that was me swaying completely to the music. (Oh, get over it. Do you...

My Love of Lingerie

by Inspire8 on Feb 6, 2018
First Time

I love to see an occasional glimpse of a bra strap bra cup, a seam, or a stocking top. I love the look. And I like how they feel. When I was eighteen years old, I knew two girls both named Anna. One fancied me and the other was her best friend. They were always together. "Strip Poker" was just about the most daring thing you would try and play back them. Th...

Being a Sissy for Viv Ch. 03

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

I awoke slowly, enjoying the warmth and comfort of the bed and thick quilt. My mind was slowly trying to separate half remembered dreams from reality. Pink panties. A lacy bra. Viv's breasts. Excitement. Embarrassment. Suddenly my eyes were open as the catalogue of disjointed dream images slotted into the reality of the previous evening. Even as the memori...

Discovered At the Gym Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

A quick backstory, I am an 21 year old college kid, about 5 foot 6, who just recently joined a gym to try and overcome my smaller frame and slim feminine body. I have a secret love for wearing women's clothes, especially lingerie under my male clothes as much as possible. I have no issues with getting women, the occasional hook up and girlfriend from time to...

Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

The Great Day

by Julia7642 on Aug 31, 2017
Fetish

I woke up on a Thursday morning in May with my usual hard on, so I took by yearbook to the bathroom and jerked off to the hot girls in my school. I then showered and got dressed and went to the bus stop where Julia was already standing. She was wearing a tight blue shirt and a very short black skirt that blew in the wind and gave me such a good look at her i...

Locker-room Panties

by CrossdresserCaitlyn on Jun 19, 2018
Transsexuals & Crossdressers

I have always had a fantasy about being taken by a guy while wearing panties but have never acted on it because I had always been in relationships with women. Since I have recently been broken up with I decided it was time to live out one of my fantasies. My girlfriend of 3 years just broke up with me and I decided I needed to get back into the gym because...