Sissy Bra Stories

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Infinite Scroll

Dream Come True Ch. 02

by Imaginatrix on Sep 14, 2017
First Time

I opened the door to the bathroom, slowly, suddenly losing my confidence. I froze, looking at my feet wondering what on earth had possessed me to do this. I almost turned back to hide in the bathroom, when I heard you say my name “Brittany,” you said it breathily, and full of an emotion I had never heard in a man’s voice. I slowly looked up at you, not bra...

For Once I Win

by Attik on Sep 12, 2017
Romance

Hello this is a story I would like to share with all of you. My name is Richard and I am what you would call a dork. I am 5'10 and 177 pounds, as you have guessed I am kind of fat. School was always the same thing, people would laugh at me and call me names, I don't blame them though, after all I was a 18 year old virgin. This is my story of how I went from...

Rani Becomes A Whore

by sumantriguni on Sep 14, 2017
Erotic Couplings

Rani was my sister and after death of our parents I had no choice but to live with rani and her husband. I assisted rani in caring her three children. During that stay I developed sex relations with rani's nephew 'n'. Story of those relations is written separately. As I spent whole night enjoying hot sex with 'n' it became more and more difficult to hide a...

Rainy Day in May

by iluvred on Aug 30, 2017
Exhibitionist & Voyeur

For the past five years it had been an on-again-off-again relationship. However, through it all we always had time to “hook-up”, no matter who Sue was dating or who I was dating at any given time. It would always start as a simple phone call, followed by a request to get together and catch up. There was never any mention of sex but we both knew it would h...

My Buddy's Mom

by standingstones on Sep 17, 2017
Mature

I spend a lot of time at my buddy Neil's house. I have to admit I like looking at his mom, Jean. What can I say, at nineteen I hadn't had a lot of experience with females. Neil's mom had to be in her early forties. She was a curvy woman with long dark hair. Her best feature was her tits. Boy, did she like to show them off. There were more than a few times I...

Flu Shot

by Decayed Angel on Sep 17, 2017
Mature

Joshua drove his beat up Nissan Sentra into the drug store parking lot and pulled around to the back, where he parked. Climbing out of the car, he pulled on his white pharmacy coat, checked his appearance in the reflections in the side window, straightened his name tag and then walked toward the store. Normally he'd enter through the back of the store, but...

I Feel Girlie

by RainStevens on Sep 11, 2017
Transsexuals & Crossdressers

As I sat in the chair, my ankles crossed and tucked in, my little boy clitty was twitching as it lay tucked tightly in the white with cherries thong. It was tight, pulling at my boy hole so that whenever I moved it dug tighter into the crack of my rounded ass. My nipples itched in the cotton bra that fit tightly around my chest reminding me of the work the h...

Three Weeks in Kathmandu Ch. 03

by mayadevi on Sep 16, 2017
Romance

It was my last week in Kathmandu, and I was crying inside thinking soon I would have to leave Kumar forever. Already I could not imagine my life without him. I called long-distance and begged for more time off and managed to extend my trip by another 2 weeks just so I could spend more time with him but eventually it got to the point where I had to leave or r...

Painting in Black and White

by patdown on Sep 16, 2017
Interracial Love

I was working on a Saturday for a buddy with a painting company to help him finish a government contract. He needed to finish a job at the state fairgrounds by the middle of the next week and I can always use some extra money. So I'm finishing up and carrying stuff to the truck I was using when I pass an incredible sight. They were having a high school grad...

She Gives Into Her Mistress

by littlemissnaughtygal on Sep 17, 2017
BDSM

It was a long awaited evening... she had finally arrived... my Mistress... a knock on the door sent my body into a nervous panic... the thoughts run instantly through my mind... (Will she really like me... Will I do everything right to please her... Will I be able to give into her completely) the thoughts as much as they scared me... extremely excited me......