Big Tit Shemale Stories

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HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

A Couple and a Shemale Encounter

by Vennessa on Sep 12, 2017
Transsexuals & Crossdressers

Not long ago I was sitting home alone on a Friday night with nothing much to do and feeling horny so I decided to go out. I showered, misted myself with my favorite perfume, put on a sexy black bra, rolled on a silky new pair of jet black sheer to waist pantyhose, slipped into a tight, very short, little black spandex dress and slid my nylon clad feet into a...

Mikes First Transgendered

by SamanthaMeyers on Nov 16, 2020
Transgender & Crossdressers

This is an absolute true story. Mike loves transgendered I had just turned 30 and was about 1 year out of my divorce. I was dating a Filipina lady named Mika who was not the best person for a relationship, for many reasons. During our relationship Mika used to take me to this Filipino dinner restaurant which had food and late night live musical shows. Duri...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

The Shemale Apocalypse Ch. 01

by cocklover1000 on Sep 15, 2017
Sci-Fi & Fantasy

The first place anyone really heard of it was large outbreaks in Thailand. No one knew what it was but the government played it off as a life choice via simple operation. But it was more then that. Minor cases were reported all over the world until 2011 the government in an effort to quell what they called an infection told the earth the truth about the wond...

Amanda and Me Ch. 03

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

The sudden ringing of my alarm clock woke me up at 6:30AM sharp. Rolling over I turned it off and then rubbed at my eyes as I began to wake up. Slowly the events of the night before came back to me and I smiled as I thought about Amanda and how wonderful another night with her was. We had great conversations and another round of mind-blowing sex and I wonder...

Finding My Shemale Goddess Ch. 01

by TheGuyInBlack on Sep 11, 2017
Transsexuals & Crossdressers

Hi, and thanks for reading my first ever submission on this site. I want this to be a multi-part series, so if you have any suggestions I'll be happy to read them. Also, I'd be grateful for any constructive criticism you may have. Thanks again for reading and enjoy! -TheGuyInBlack ********** My hand was trembling as I knocked on her door, I've never been...

A Black Tranny Fantasy

by tsfantasy on Sep 13, 2017
Transsexuals & Crossdressers

It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sleeping with a black shemale was about to come true. She paused at the bedroom door and smiled at me. 'You like what you s...

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...