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Moms Trannie

Moms Trannie

... was stare, mom broke the trance by smacking my butt, and offered up more drink, the conversation got ... now.

Sharon (moms name) and I climbed into bed and Jamie excused herself to the bathroom, Jamie ... mom.

Before I realized it she had swung her leg up over my head and as I looked up I could see... Continue»
Posted by frswriter 2 years ago  |  Categories: Shemales  |  
  |  35

Kelly Pimps Out Chrissie (a Chrissie Conway story)

... of the reason I'm a high paid "tranny whore" today. Kelly never missed on opportunity to
"pimp me out ... any lights
on or you might wake my mom."
"Got it" he said "10:00 PM, side door and no lights ... ."
The truth was that my mom was currently working four to midnight and wouldn't be home anyway but he... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Sex Humor, Shemales  |  
  |  5

Missed You

... his grandparents’ house that he shared with his mom and b*****r. Jessica owned her townhome ... became wetter.

“I love how my tranny pussy creams on my dick,” Kamal announced.
“Yes, Mr. Stewart ... . It’s your tranny pussy,” Jessica cooed.
“Damn right! Ride your dick, baby!”
“Yes sir,” Jessica... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Hardcore, Shemales  |  
  |  2

Never Wanted To Be Your Girlfriend Ch. 04

... voice.

A shocked gasp swept over the room. A few murmurs of "fag" and "fucking tranny" could be heard ... and women's rights? Your mom will eat that shit up, and then she'll bring your dad around. And if all ... we came in. -----

My mom came into the office and looked around confused. I tried not to make eye... Continue»
Posted by sparkyking 1 year ago  |  Categories: Taboo, Shemales  |  
  |  5

How I started Cross Dressing and other first times

... .
My Mom did the laundry. I have an older s****r. One day, as I was getting ready for school, I ... a dollar store pair, which would not be unusual in my house as Mom was a great penny pincher. Being ... along with any of them.

Trying on the Neighbors' mom's bra in front of him.
Through High School... Continue»
Posted by pantiesdave 4 months ago  |  Categories: Fetish, First Time, Taboo  |  
  |  2

A young man's summer [full story]

... in the room. Usually this was a sock on the doorknob, which Mom never did quite understand!

As time went ... toys and tools. Though, I must say, some of the trannies I watched nearly made me cum in my drawers ... of wood, plus they were hard to clean the slippery off of. [I did not want Mom to ever ask why... Continue»
Posted by serious58 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  3

More Perverted Sexual Cravings

... grandpa had told him one evening to be sure and peek in his moms
His dad had gone to town ... heard his mom go to

After a few minutes he heard her door open again then he waited awhile ...
longer and tiptoed to her door,which had been left partly open.
He could see his mom laying naked... Continue»
Posted by bioralpleaser 4 months ago  |  Categories: Gay Male, Taboo, Hardcore  |  

The Cheaters

... into her ass crack. As he made love to her tranny pussy, her body, all one hundred and forty-five pounds ... loudly knocking him back into consciousness. He rubbed his eyes and focused on the screen – it read MOMS... Continue»
Posted by faggyboi 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
  |  7


... ! We set out early even before Mom was up Mom's a heavy sl**per a bomb could go off and you'd have ... thought about how lucky I was that Mom had found such a great guy and that this great guy was taking ... it in his hand and smiled “This has to stay between us though Tru your Mom wouldn't understand!” I said... Continue»
Posted by laceysgirl 1 year ago  |  Categories: BDSM, First Time, Shemales  |  
  |  4

Sissyboy Conversion Therapy

... . Like, you fuck a tranny and
find out she s a he later on. If you a) kill b) maim or c) walk away ... from
(he couldn t recall which, said tranny within five minutes, your
heterosexuality remained ... . And selected times during the day.

Mom was OK with it, and so was Jack.

Jack wasn t braggy... Continue»
Posted by swallow4fun 6 months ago  |  Categories: Anal, First Time, Mature  |  
  |  3

Never Wanted To Be Your Girlfriend Ch. 02

... , and Michelle's mom passed out -- After catching her son and his best friend in drag sucking each other off, I ... along with cash she swiped from her mom, and some make-up. She handed me the purse and smiled. We ... scream. If your mom finds out what you've done, you're fucked," I spat.

"Oh, no you won't. You see... Continue»
Posted by sparkyking 1 year ago  |  Categories: Taboo, Shemales  |  
  |  2


... ?"

"Alright, this should be a good one. My b*****r has turned into a tranny because he has to," Tisha ... . Now, up until about a year ago, everything I've been telling you and mom has been pretty accurate ... to meet up with some people during the day, but that's about it. How's mom doing?"

"She's OK. Work... Continue»
Posted by sexaddict66 3 years ago  |  Categories: Taboo  |  
  |  1

Gary's Dressup Sissy

... from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One ... in the front of Gary's jeans and knew his cock was doing the same.
Gary then moved to his mom’s wardrobe ... it to me he said
"Cum in that, don’t get any on my s****r's or mom’s clothes"
I positioned my cock... Continue»
Posted by palmorr 5 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  10

My Step-Sissy

... I divorced his mom, I got a little harder on the k**. I didn't want to hit him when he fucked up ... sweet asshole to give my tranny boy's big dick some attention.

"You got a big dick, boy. Real big... Continue»
Posted by nymphRiley 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
  |  1

paying to be used as a girl

... i's been dressing up in girls clothes since i was 11. my mom's and my 2 elder s****rs suff. they'd ... ....sometimes the fantasy would involve several men.this had come about ever since my mom had bought our first ... home computer. I'd spend hours when home alone watching tranny porn on the internet. i'd even posted... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  9

The Secret Of Angel

... big cocks. She then pushed me against the door of my moms car in the driveway , & she put her hand ... stomach , arms , & cock , leaving me soaked in her tranny cum like wet dog in rain .
... Continue»
Posted by shemalecum1 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  2

Never Wanted To Be Your Girlfriend Ch. 01

... of import business, so his Mom, and older siblings, s****r Brittany and step-b*****r Derrick, pretty ... and opened a folder full of movies.

"I got a a ton of videos like this. Trannys rule!"

I stared at him ... nodded as I clicked on hot tranny movie after hot tranny movie. I lost track of time as I watched... Continue»
Posted by sparkyking 1 year ago  |  Categories: Taboo, Shemales  |  
  |  5


... ? That's an understatement. At least I don't
have to worry about upsetting any of them with all this. My mom ... the next few months," she said. "Eventually
he left Mom, and that was the last time I saw him."

"See ... spend much time on the murder of a trannie

"Why did you have to tell them that you knew her... Continue»
Posted by klammer 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
  |  6

Party Skank Shares a Great Show

... scene on the TV - a woman being fucked by a tranny, sucking his tits while his elegant cock moved ... and the tranny.

My friend's soft voice interrupted. "How do you like MY wide-screen show? This guy ... erect penis. For a moment everyone turned to the TV to watch cum from the tranny's cock leak from... Continue»
Posted by smallfurrycreature 3 years ago  |  Categories: Group Sex, Masturbation, Taboo  |  
  |  9

Part 2 to First Time I shared My Dad

... to party with dad just about every other weekend as mom was always gone then. The first time back we had ... on a Friday but my mom dragged my dad to some dam work dinner of hers so we all couldn't leave till Saturday ... an early start but he just hung his head and said " No you have a phone call. "
It was Lisa's mom... Continue»
Posted by Mluvsdad 5 years ago  |  Categories: First Time, Taboo  |  
  |  10