Sissygasm Chastity Stories

6,936 results
Orientation
Length
Source
Infinite Scroll

Tara has a Threesome

by SissyTara on Oct 13, 2017
Transsexuals & Crossdressers

I was lying in bed one morning. Dave stopped by on his way to work at the construction site down the street. I answered the door in purple bikini panties and a matching baby doll nightgown. We had fucked a few times since our first encounter when I had walked by the construction site. He stepped inside without asking and kissed me hard on the lips. I respond...

Ashley's New Friends

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Special thanks to my best friend for editing this! Hope you enjoy, love you dolls! Xoxo ***** One day Asher was sitting in a library on campus doing his homework, or at least he was supposed to be doing his...

The Emergence of Jocelyn

by JocelynF99 on Sep 17, 2017
Loving Wives

"Oh daddy. Oh daddy, you make me feel so good." "Oh daddy, you make me so hot for your body." "I love it when you touch me. You make me feel so good." "Please daddy, please daddy, make love to me." "I need you so badly." "I need you inside me." "Ohhh, OOhhh..." "Please daddy, make me your woman." "Please daddy, please daddy, please fuck me." "Oh God...

Innocence Lost Ch. 04

by bradley_stoke on Sep 1, 2017
Novels and Novellas

In Which Innocence and Chastity are found in the countryside. Une just loved to be fucked. But with a cunt as large as hers it took such an effort for her to be satisfied. Generally, one man just wasn't enough, she'd need two or maybe three simultaneously pounding away in her nether regions for her to be satisfied. It was sometimes awkward to arrange such...

Carl & Chastity: 2nd Date

by Ninjafish on Sep 14, 2017
Erotic Couplings

Chastity didn't ring until the evening. She had had quite some debate with her friends over a coffee in the morning about how soon is too soon, the usual argument erupted. The married friend telling her to not play games and ring straight away, the single friend telling her to wait a week and even then tell him you are busy. Sadly she never managed to put tw...

Candace's New Years Eve

by Dominic_Lee on Sep 17, 2017
BDSM

Chastity had worn her locking heels out quite often and no one ever mentioned them. Normally she would hide the locking portion under a pair of jeans. All anyone ever saw was another pair of black heels, which she owns a lot of. This is until New Years Eve. Aiden asked her to wear them out to the club that night. He liked them and wanted her in them tonig...

The Abdominal Snowman

by Cashmere_Snow on Jun 1, 2020
Sci-Fi & Fantasy

This is the second story in The Erotic Adventures of Chastity Summers. It follows Romancing the Raptor. ** Chauncey Adams started the day with a light breakfast of coffee and toast, explicitly avoiding any added sugar or cream or condiment that might irritate his bowels on such an important day, but, with each exhausted, stumbling step through the darkness...

Everything Has a Price Ch. 12

by MALIBUMAN666 on Sep 16, 2017
BDSM

Author's note - don't forgot new stories from me will soon be posted under 'Robert_Anthony' - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - The 'soft' option... I .................................... (hereafter referred to as 'slave'), agree this day ....../ ...... / ............... to be bound...

Innocence Lost Ch. 03

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Alice is introduced to Innocence and Chastity, and discovers that of the two she prefers Innocence; her friends practise the thespian arts and learn the theatrical skills of Innocence; and, to her disappointment, she discovers her lover prefers the charms of Chastity. Alice wasn't so sure she liked the idea of being identified for her incestuous r...

Collecting Catholics: Chastity

by Sosela on Sep 12, 2017
NonHuman

"You have to come see this!" Catherine giggled conspiratorially, looking left and right to make sure no teachers or nuns were around. Mt. St. Vesper Ladies Finishing School was quite strict, and the staff tended to spy on their students even though they were of legal age. It was a catholic college in all but name, and even though the Dean said that student...