Sissy Bra Stories

144,731 results
Orientation
Length
Source
Infinite Scroll

Frat Party

by thestargazer on Sep 25, 2017
Transsexuals & Crossdressers

It was my first frat party. I had no idea how I wound up there. The liquor was flowing hard, and the rooms were packed. The guys were all football stars, hooting and chugging, and the girls were all skanks. I'm used to thinking of girls as dignified, delicate creatures. But these girls were screaming at the top of their lungs, grinding their crotches against...

Ann's Art Project Ch. 06

by qexiqex on Sep 13, 2017
Fetish

As soon as the dean waltzed away, Sue jumped to the column and yanked the handles upwards. She whispered, "Hey, Ann, are you OK? This... woman..." "I... I heard every word, Sue," hushed Ann, "Fuck, my tits felt like they would pop any minute! Thanks for releasing those handles. What a stupid, stupid idea. I should have seen that coming! I should have used a...

Undercover Ch. 2

by English Bob on Sep 15, 2017
Group Sex

Part II: Flying High This story follows on directly from Undercover Sandra awoke to the low hum of aeroplane engines feeling completely disorientated. Where was she? And how the hell did she get here? She rubbed her eyes, swollen from enforced sleep and tried to swallow. Her throat was sore and her head ached. As her eyes came into focus, she saw two famil...

Three Kids in a Tub

by HectorBidon on Aug 31, 2017
Exhibitionist & Voyeur

If you want to know about the handcuffs and the fashion design project, this story follows "Waiting for the locksmith" and "Trying to date a seamstress." ***** My phone rang. It was Mindy. "So guess what I got." "Mononucleosis." "No," she laughed. "A gift certificate for the hot tubs. I won it in the Spring Fling raffle." "Jeeminee. What are you going...

Car Pooling Pt. 13

by TonyMA70 on Apr 23, 2018
Exhibitionist & Voyeur

The following night at four PM another meeting ensued to finalize the exposure of Walter's wife Gloria. It was decided by the group the first encounter with the display table for Gloria would be on the weekend, which is four days away. They made their plans for the group to be there. Walter told his wife Gloria, she needs to demonstrate a new table which was...

My Red Neck Biker

by irishrose1978 on Jan 7, 2018
Exhibitionist & Voyeur

Merry Christmas Big Man! I apologize for the slow beginning and want to explain that this will end up as a series. This however is not the first story in the series but I wanted to get the hotter stories out first, Enjoy! ***** It was finally the night when Tristan and I planned to meet. Planned to fuck. After months of playing and sexting, making pornogr...

The Office Mom

by onceamarinedjr on Nov 13, 2017
Mature

She may be nineteen years older than me, but she's still the hottest woman I've ever actually met in person. Her name is Janie, and her desk is about ten feet behind mine at work. She's short and petite, with fantastic legs and the most amazing ass I've ever seen. Her blonde hair really stands out, but it's far from the only thing about her that draws my att...

Sweet Boy Ch. 01

by MeesterNicee on Oct 14, 2017
First Time

Steve's sexual initiation came during the summer of his 18th year. Except for his youth, there wasn't anything terribly appealing about him; the girls in his town were unimpressed and made that plain anytime he'd try to talk to them. After a while Steve would get tired of ridicule and rejection and retreat back into his nice safe shell. So there he was, a...

Country Store Ch. 12

by teachgirl1980 on Sep 19, 2017
Exhibitionist & Voyeur

(This is chapter 12 of a series. It will make more sense if you read them in order) * I woke up next to Tracy. We were both still naked and her back was to me and my arm was over her and across her chest. I felt her boobs against my arm. I was warm and comfortable. I snuggled against her and I felt her push back against me. We stayed like that for another...

Pirate Abduction Ch. 03

by IamAlpha on Sep 14, 2017
BDSM

This is chapter 3 in the story of Jim and Janet's pirate adventure. This story will make more sense if you have read the previous installments. Jim and Janet didn't discuss the pirate scene again for a couple of days, and Janet wondered if Jim was serious about further testing. Jim, meanwhile, now that he knew Janet was submissive, began assembling some toy...