Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll

Awakening of Sensuality

by TheHuntress on Aug 18, 2017
First Time

A true story When I was 18 we went camping on the Colorado River. I was tall, had long sable hair to the bottom of my tight virgin ass, and looked much older than 18. My skin was dark from many hours out in the beautifully hot sun, and from my own Native American heritage. My already large breasts were full and ripe, and even a slight breeze could make thos...

Sanctuary

by starrkers on Sep 25, 2017
Erotic Couplings

There were days when life really sucked and this was fast turning into one of them. It wasn't bad enough that she'd missed a turn somewhere and managed to get completely lost; oh no. While she was trying to figure out where the heck she was, she had the good luck to have a dog run onto the road and, in her efforts to avoid it, she managed to put the car in...

In Praise of Older Women

by gordon_a on Sep 14, 2017
Mature

From the word go I was interested in older women. No, obsessed would be the better word for it. In those days, of course, that meant just about all women, if you disregarded the giggling, barely pubescent girls who seemed from another planet. No, it wasn't them I was interested in - it was their older sisters and mothers, and the mothers and aunts of my fri...

The Drover's Song

by dass4450 on Sep 17, 2017
Mature

"Ooh, Gillian, look what's coming though the gate." "My gosh Ellen, what a strapping young man. This may be the boarder that Pastor Nicholls rang us about, the one that's here to study theology at the university. He has a suitcase and an overnight bag. Gosh, he's got a lovely tan under that enormous hat." "The pastor did tell us that he was an ex-drover fr...

Loving A Maasai Warrior

by Samuelx on Sep 3, 2017
Erotic Couplings

Black. Biracial. Mixed-race. At some point, I've used all of these terms to describe myself. Today I am only me. Wanda Beaumont. Friends call me W.B. for short. I was born in the City of Toronto, province of Ontario, to a Haitian mother and Irish-Canadian father. My biological father Sean O'Leary never married my mother, and in fact, he had to be forced by t...

The Halloween Party

by Middleagepoet on Sep 17, 2017
Loving Wives

I have to admit, the Halloween Party was a lot better than I expected. When my wife, Annie, first mentioned it to me, telling me it was at the Mather's house I was a bit apprehensive. June and Ed Mather were both okay as neighbors, but they weren't what I would call close friends. Sure we had been friendly and had even gone out with them on several occasions...

Settting Up Jackie

by Just Plain Bob on Sep 17, 2017
Loving Wives

Jackie was a stuck up bitch with an "I'm much better than you" demeanor. She looked down her nose at every one else in the family and I can honestly say that there wasn't anyone in the family that liked her with the possible exception of her husband Matt. I say possible because I'm not even sure he liked her after being married to her a while. Matt, or Mat...

Helping the Brother in Law

by guzzieathome on Sep 13, 2017
Loving Wives

I have just remembered a short true event that happened when my wife's brother-in-law (B-I-L),came to stay with us for a while when he attended a training course for his work. We enjoyed his company and all got on very well together. Over the years that I had known him there had been a number of 'flirty' comments from him about my wife.I also knew that when...

Playing with Fire Ch. 02

by RedAmazon03 on Sep 12, 2017
Novels and Novellas

She sat with her long legs crossed and draped over the desk’s edge. J.D. was late again. It was his personal game to keep her waiting on him. He loved to push every button to see how much she would take before going ballistic. Well, he was in for a major shock this Thursday evening, she thought looking at her watch. Her fuse was startlingly short. “Son of...

Undone

by juanwildone on Sep 14, 2017
Erotic Couplings

An empty beer bottle arced through the air then broke the smooth surface of the water with an unimpressive splash. Mike watched the ripples spread out across the pond until they lapped against the shore at his feet. He reached into the cooler, the cold felt good to his hand, and pulled out another bottle and twisted the cap off. The ice-cold liquid gurgled d...