Shemale Surprise Stories

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Girlfriend's Shemale Surprise

by Artvan1 on Sep 24, 2020
Transsexual

As Carter finished unpacking after dinner, he couldn't help but smile. His last summer before having responsibilities would be spent in the beautiful home belonging to his girlfriend's parents. Carter and Chloe had only been dating for a few months but were both entirely consumed in the early parts of their relationship. From hand holding to mini-golf the yo...

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Blackmailed by a Bitch

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'I got it,' Laura said, running into the kitchen. 'I got the job!' That's great,' Dave said. He hugged his fiancée, full of joy at the news. Laura had been desperate to find a new job. Anything to get away from the place where she worked under her nightmare boss, Gloria. 'When do you start?' Laura's smile disappeared. 'As soon as I get my reference.' 'Fro...

Virginia's Luxurious Evening

by JonathanStone on Sep 16, 2017
Transsexuals & Crossdressers

West Palm Beach didn't have many cold snaps, but when one did rake the city the weather seemed twice as frigid as it actually was. Virginia Stanton sat alone in her office on the third floor of Prism Design's building overlooking the Intra-coastal Waterway. She had been chilly all day, mainly because of the dampness in the air; Forty-eight degrees outside wa...

Garnet: a Story of Submission Ch. 03

by frillypanty on Sep 16, 2017
Transsexuals & Crossdressers

3. A fashion parade and the appointment of a fourth Mistress The image of my three internet mistresses came up true to time, immediately after I'd logged on at 1.15am on the Sunday morning following my second shopping expedition to extend my feminine wardrobe – as directed by them. Like me all three were clad in lace trimmed and panelled underwear – bra',...

Craving Shemale Cock Ch. 01

by jeritza on Oct 22, 2019
Transgender & Crossdressers

I stood nervously on the dark cobblestone alley street, in front of the unmarked door, running through the possibilities in my head, speaking under my breath. I was thinking of all the events that led me to this moment - the perverted path I had gone down. This is it. This is finally happening. No turning back now. Dear god, no turning back now. *** I was...

Erin and the Shemale

by kimberlykitten on Sep 25, 2017
Transsexuals & Crossdressers

Erin was up bright and early on Friday, getting a good hour jog into her schedule. She didn't have to be in class until two hours from now. As she was jogging, earlier male joggers had passed her by with their eyes directly on her bouncing melons. Even wearing two sports bras and two regular bras weren't enough to hold Erin's gargantuan jugs down. Erin did...

Mardi Gras Surprise

by HerLittlePiggy on Sep 12, 2017
Transsexuals & Crossdressers

"Is this what you want bitch?" Tiffany asked sternly as she waived her hard cock in front of my face. "Yes," I hissed as I looked into her dark sexy eyes. "Good answer bitch now open wide and suck my cock," the sexy shemale ordered as she rubbed the head of her cock across my lips. Precum oozed from her cock and coated my lips. I closed my eyes and ope...

Amanda and Me Ch. 02

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. As I lay there thinking about the night before I was surpris...

Shemale Shopping Spree

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye a...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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