Shemale Massage Stories

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Housewives

by cuteliz86 on Oct 11, 2017
Transsexuals & Crossdressers

Contrary to her name, Sandy had long, brunette hair. She was a little over 5 feet tall, and very skinny and petite. She lived in a pretty normal neighborhood, filled with traditional families with traditional parents and usually around 2 or 3 kids. There were a few singles in the neighborhood like her, but only a few. The moms in the neighborhood were pretty...

Office Punishment

by Chewiebon on Oct 15, 2017
BDSM

Contrary to her name, Sandy had long, brunette hair. She was a little over 5 feet tall, and very skinny and petite. She lived in a pretty normal neighborhood, filled with traditional families with traditional parents and usually around 2 or 3 kids. There were a few singles in the neighborhood like her, but only a few. The moms in the neighborhood were pretty...

Cabin Fever

by mutterguffin2 on Sep 13, 2017
Illustrated

For the past few months I have been been having an incestuous relationship with my two older sisters Becky and Lisa. The last weekend with my sister Lisa left me with mixed emotions. We both confessed to having developed strong feelings for each other that went beyond normal sibling affection. It even went beyond the amazing physical connection that she and...

Debra and Tom

by murphy621 on Sep 19, 2017
Loving Wives

I was bent over the back of our sofa with my wife's strap on buried deep in my ass. I was screaming, "Yes, yes, fuck me Mistress, I am yours, I belong to you, I am your slave boy." She stood behind me, a big smile on her face as she pounded away, the other end of the dildo in her cunt and she commanded, "Cum, cum, slut boy, cum with me now." And we bo...

Transformed Into A Shemale

by girlboybootsie on Sep 13, 2017
Fetish

I was 18 when I first had sex with a man. This is the story.... I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have be...

Jemima's Tale Pt. 05

by jemimaheart on Sep 13, 2017
Transsexuals & Crossdressers

Part 1 - Jemima Needs a New Man Oh I really really REALLY missed having a boyfriend! All you girls out there know what I mean - nothing is ever quite the same once you've experienced what it's like to belong, sexually, to another man. Before Steve accidentally walked into my life, I'd spend endless hours fantasising about having a boyfriend of my very own,...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

The Lost Boy Ch. 02

by DamienDeath20 on Sep 25, 2017
Transsexuals & Crossdressers

A.N. Hello hello hellooooo! Welcome back to the next chapter of The Lost Boy! Chapter one received soooo much positive feedback, and with a lot of encouragement from both you guys and the commissioner, chapter two was very quickly conceived! The Following Contains: Rough sex between a sexy as fuck dominant dickgirl and an adorable femboy. Who is reluctant...

Open Your Mind to Something New

by Dazman on Nov 4, 2019
Fetish

Open minds create amazing experiences This experience had its genesis in my early twenties when I unexpectedly began exploring my bi-side with my childhood buddy, Lyndon while both of us were studying at university (refer to my story Friends Satisfying Each Other for background context). This story takes place over a weekend, Friday evening to Sunday after...

Cheerleader's Mom: Fucking Her Ass

by silkstockingslover on Dec 9, 2019
Illustrated

Summary: Submissive Mom is trained in orgasm denial and ass fucking. Note 1: Thanks to hfernandez1983 for doing the visuals for this story. Note 2: Thanks to Robert, Wayne, and Tenzin for editing. Recap: In Part One, A POWER SHIFT: 39-year-old mother, Michelle, decides to try on her daughter Allie's slutty cheerleading outfit. Once she has it on, she beg...