Sissy Sex Stories

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Divorced in South Florida Ch. 06

by BoRaFL on Sep 13, 2017
Mature

I had discovered three wonderful women who showed their affection by sharing their asses with me, but I was having difficulty finding other new bedmates on my own. I was discounting the blindfolded lady because Lynn found her, and I did not know who she was. My failure to find bedmates was not caused by being overly selective or insisting on assplay games....

My First Threesome

by A_Good_Username on Sep 1, 2017
Group Sex

When I was 18 I had never thought about having a threesome... My boyfriend and I had just started having sex about a year ago for Gods sake! Steve, my boyfriend, was 22 and would always take me to parties at the college that he went to which usually ended up with me drunk and us making out at the party then going back to his place for some incredibly hot se...

And Here's To You Mrs. Robinson Ch. 01

by BOSTONFICTIONWRITER on Sep 14, 2017
Mature

I was 27-years-old. She told me she was 42-years-old. I found out later that she was 45-years-old. What did it matter? It didn't matter to me how old she was. I wanted her. Certainly, she didn't look her age nor did she act her age. She was zany. She was fun. She was everything that the younger women my age were not. She was beautiful. She was sexy. She had...

My Darkness

by Tinymage on Sep 16, 2017
NonHuman

I had too much wine last night. He likes to come to me when I've been drinking. I'm more docile for him, more accepting of what he brings me. His face hidden in the shadows I've never seen him clearly, and I don't think I care too. His body is enough, his chest and abs chiseled, his thighs powerfully defined, his cock thick and long. I was lying there, nude...

My Life as Lauren Ch. 03

by Lauren_xxx on Sep 13, 2017
Transsexuals & Crossdressers

I had become a manager in the shop which meant that I had to dress in a very professional way, if I was still a man it would have been quite annoying but Bev new that as a woman I would love to wear a blouse and skirt but she also knew it meant that I could dress really slutty at the same time a "smart tart" in a way. Whilst working there the shop had opened...

The Toilet Monster Ch. 04

by PrevertOne on Sep 12, 2017
NonHuman

(Inspired By "Surprise" by Imagination Station/Shyguy) (Thanks to Jen Lit Girl for the edit.) * Eve experienced the bumps and the kicks in her womb with growing trepidation. Her belly bobbled and vibrated like the bell on a telephone. Her fearlessness about belly bursting monsters diminished to a mild bravado. Something was happening with her other monst...

Morgan and Jake

by Butteronyourfly on Sep 14, 2017
Erotic Couplings

Six months ago, Morgan would have never thought she would have had sex outside of a serious relationship, but occasionally she surprised herself. She had met Jake on the Internet and a week later had met him in person. She had every intention to take it slowly, but once again, she surprised herself. The first time they met Jake came over to her apartment and...

Twist of Fate

by erotiquill on Sep 17, 2017
Loving Wives

Although it's a cliché, it was love at first sight. Emma was 16 and Ray almost seven years her senior. They married a year later and began their lives together. As the years passed they lived ordinary lives, purchased a house then a larger one after the two sons arrived and settled into a busy but comfortable life. The boys grew up, married and left home and...

How To Have a Grrreat 69

by FriskyVirgin on Sep 1, 2017
How To

How to Enjoy 69: Getting the Most out of Mutual Oral Sex What is a 69? This is considered one of the best oral intercourse positions as it allows both partners to stimulate each other at the same time. Either partner can be on top, but performing fellatio is significantly more difficult when in the bottom position... just remember not to forget to stop and...

Misery Requires No Talent Ch. 2

by Bill Smith on Sep 16, 2017
Novels and Novellas

Justine can tell she is now in the bathroom as the floor is now covered in tile. Her leg brushes past the toilet yet Dennis does not stop. Dennis tells her to pick up her left foot and step forward and when she puts her foot down she can tell she is entering the bathtub. Finally both feet are in the tub and Dennis rearranges her. "Justine, if nothing else,...