Big Dick Shemale Stories

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Orientation
Length
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Infinite Scroll

Pillow

by CrazyDaveTrucker60 on Jun 8, 2020
Loving Wives

This story is so way far over the top, it is almost suborbital. No one under eighteen, any resemblance to anyone living, dead or living dead is just coincidental and this is a work of fiction. Please remember to place tongue firmly in cheek when reading. Keep all arms and legs and tentacles in, and enjoy the ride. Buckle up, insanity ahead. You have been wa...

Waiting

by mothman34 on Sep 24, 2019
Transgender & Crossdressers

Warning: TS on male sex, watersports, ATM, cum eating, frottage, just a lot of kinky shit. If you’re not into that, no big deal, if so, please enjoy. * “Why don’t you go get in the shower and wait for me??” The way she said it made it sound like it was a suggestion, even though we both knew full well it was intended to be a command. Either way didn’t real...

Trey and Cate & What Happened

by itispossible on Sep 14, 2017
Loving Wives

My husband, Trey, and I have been talking about joining the "lifestyle" for years. The closest we had ever come to actually indulging in our fantasies was getting memberships to the local swing clubs. We had tried out several of the clubs, but I must have chickened out each time. There had been some very close calls to swapping with a couple in a hot tub, bu...

The Arrangement

by tiamat3x on Sep 12, 2017
Erotic Couplings

Act I: Hey You The day started as normal as any other Brian was up at 6 am to help get the kids ready for school. He was dressing his 3-year-old son while his wife was busy trying to find something suitable for their teenage daughter to wear that would not get her kicked out of school. At 7:30 a.m. the kids were dressed, fed and out the door. Brian's wife...

A Maid's Special Day

by Baloden on Sep 14, 2017
Erotic Couplings

Attention: This story is fictional, it is not real. You need to be eighteen years of age or older to read this story. If you are not or if you don't like sexual themed stories please stop reading this story now! Please go to a different web site. I may write this story as if it happened to me but it didn't. Characters: These are the characters in this story...

Flight of Fantasy Pt. 02

by JenniferWilson on Aug 18, 2017
Fetish

Dave's mind was in turmoil, here he was dressed partially in women's clothing that all the world could see and stare at and think 'what sort of guy would wear a rubber skirt in public?', but at the same time he was ecstatic at being able to wear the latex panties and skirt especially as they had only just come off a beautiful women who he had brought to an o...

The Runt of the Litter... Pt. 03

by Kent100 on Sep 12, 2017
Transsexuals & Crossdressers

This story originally only dealt with the topics of gay sex and incest, mostly suited for a long jack off story. As the story has taken a twist, while it's still man on man sex, it also involves cross dressing. So I am entering this in Transsexual and Crossdressers catgory. If these topics offend you, please avoid it. If there is any interest in it, let me k...

The Pakistani Widow

by Mystery_Meat on Sep 18, 2017
Mature

All characters are fictional. Any resemblances to persons living or dead are coincidental. Relax and get horny. It's only Literotica. * Nick peered surreptitiously out of his side bedroom window. Ana had just come out to put trash in the garbage can next to her garage. As Nick had expected, his neighbor was sporting a fresh black eye. After the loud battle...

The Gap

by mrpeachesva on Nov 26, 2017
Erotic Couplings

The three friends laughed heartily at the story one of them was telling. They were all on lunch break and sitting at a picnic table at a local park near their job. "Girl, that boy got so mumble-mouthed when I showed him those pics..." Cassie said. She was telling the story and she was 27 years old. She was telling the other two women, 32-year-old Kayla Simm...

Encounters with John Wayne Ch. 17

by surober1 on Sep 13, 2017
Celebrities & Fan Fiction

John Wayne had not seen Diana Maitland for an hour now—not since he had walked out and closed the door of the master bedroom suite after instructing her that she was to bathe, dress and meet him at the bottom of the stairs at precisely 5:45pm. As soon as he left her, he put his bags in one of the bedrooms, then he went downstairs and out to the beach to brin...