Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

Aphrodite's Island Ch. 01

by Skol on Sep 13, 2017
Humor & Satire

In the marble ruins of an ancient Greek temple high on the hill, the sound of an approaching motorboat penetrated Aphrodite's deep and dreamy sleep. The early morning sun glimmered on the rippling turquoise waters that stretched to the horizon all around, gleaming brightly on the white sand of the beaches, casting colour on the rocky slopes and olive trees o...

The Library Ch. 35

by AKAheyU on Sep 16, 2017
Novels and Novellas

Chapter Thirty-Five Mark Waters pushed open the library door and closed it behind him. He glanced around the bathroom and saw that things had moved around a bit since the last time he had came to check on the house. He did it every 6 months or so to see if Amanda had moved in yet. Someone had been here, but he wasn't convinced it was her until he went into...

The Demons Within Sydney Ch. 04

by BangU on Sep 17, 2017
Mature

The past few days had been confusing. At times I found myself incredibly excited with the events at Dancer’s. Knowing that I paraded half naked in front men made my body tingle with desire. I thoroughly enjoyed the sexy clothes that I purchased with Ty. I was slowly coming to the realization that men found me sexy and attractive. Yet I found myself uncomfort...

Danny

by ofloveandlust on Sep 17, 2017
Loving Wives

She told me to be there at 11:00. Not at night, 11:00 in the morning. Is 11:00 still morning. I was always iffy on that subject. You couldn't get breakfast at McDonalds at 11:00 so I figured it shouldn't be considered morning anymore. I guess it didn't matter. 11:00 it was and I knocked on the door. She told me to knock quietly. She would hear, she assured m...

V&T, a Lesbian Love Story Ch. 05

by LadyTigeress on Sep 16, 2017
Novels and Novellas

Week Five: "Pride goeth before the fall" The Phoenix Saturday Market was located just off one side of downtown, several pedestrian-only blocks cordoned off for a huge array of craftspeople and artisans. Trin and Woofer spent the morning meandering around them, alone. Violet had yet again declined to come, and after she explained to James where she was goin...

The Cottage by the Sea Ch. 01

by locodriver8776 on Sep 16, 2017
Novels and Novellas

Editor's note: this story contains gay male content. * Living in a secure high rise tower block allows one to have certain privileges, mine during these hot summer months is to walk about naked, after all my only possible snoopers are the pigeons and gulls that roost nearby; it also makes it easier for me to masturbate or wear erotic plugs and jewellery if...

Influential Factors! Ch. 01

by gummidurango60 on Sep 12, 2017
Transsexuals & Crossdressers

Note: This is the beginning of a fictional story, the origin, in which the main character faces the love of cross-dressing or divorce. Who is she? Are there any morals? This is the origin of the base characters and will build slowly. If you're at all familiar with my stories you know that I love putting my characters through situations that either accident...

Cinderella and the King

by Cinner on Sep 19, 2017
Celebrities & Fan Fiction

King Chisulo looked out over the balcony on the stately gardens surrounding his palace and sighed. He had received yet another report through the papers that his only child and heir, Crown Prince Adebayo, was spending increasing amounts of time with his new crush, the racing driver, Ashton Speed. Chisulo was a liberal thinker. He did not have a problem that...

A Hard Decision Ch. 01

by sexualauthor69 on Sep 14, 2017
Erotic Couplings

This stroy is completely fictional, and all characters portrayed are all over the age of 18. Have you ever been in love with two people, but you don't have the guts to tell either of them because your afraid of their answer? Or, you don't know who to chose, because you don't want to wonder later in life what could have been with the other person? You're abou...

Reunion

by aurenard on Sep 13, 2017
Erotic Couplings

Rose looked out at the sky. It was a clear, late summer night, and she could see the moon glowing above the trees. Although this image would calm most, standing under the stars brought her back to a night many years ago, one that still remained unresolved. The summer after she turned 18 had been the greatest of her life. Rose had spent it backpacking far fr...