I came home and the babysitter was looking extra hot! Gigantic tit's and these lips that were aching for a sucking. I knew she wanted it since the day I hired her. So after all this time I got to fuck the sitter, even though she whipped out a hard cock I was ok with it and she was ok with me ramming her tight trannie tush!
Starring: Celeste, Aly Sinclair, TS Foxxy, Stephanny Tricks
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

Who knew that hiring a tranny had such extra benefits? A rock hard cock after a long day of work, some stress-releasing ass thrusts and some nice oral cock massages! Man, this is the best! I can't wait to cum home to my transsexual babysitter.
Starring: Amy Daly, Sasha Stokes, Khloe Hart, Juliette Stray, Heidi Mayne.
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

Finding that tranny babysitter was the best idea you've ever had. You come home after that long day at work and the babysitter helps you forget the stressful day. A little stroking, sucking. then some hardcore fucking.
Starring: Morgan Bailey, Carmen Moore, Holly Sweet, Angela Bratzz, Sheeba Starr
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

Hiring that transsexual babysitter was the greatest idea you've ever had. You come home after that long day at work and the babysitter helps you forget the stressful day. A little stroking, sucking, then some hardcore fucking.
Starring: Madison Montag, Yasmine Lee, Morgan Bailey, Khloe Hart, Kimberly Kills
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

At the end of a hard day wouldn't it be nice to have a beautiful Transsexual Babysitter to cum home too. They can rub your feet and beat your meat. So bring home plenty of bacon and get ready to cook all night.
Starring: Mia Isabella, Aly Sinclair, Victoria Di Prada, Gaby
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

Some guys have a tit fetish, others a cock fetish, and some even have a babysitter fetish! Well we've put them all together and come up with Transsexual Babysitters!
Starring: Domino, Morgan, Jesse, Paris
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

Like peanut butter and jelly, we’ve combined two of the yummiest treats, Transsexuals and Babysitters!! When you call these sitters, you’d better get ready for a serious night of hardcore cock sucking and ass fucking the way only tight assed Trannies can deliver.
Starring: Kimber James, Astrid Shay, Morgan Bailey, Amy Daly, Christian
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

A fucktoy has been bimbofied, in the Bimbofication Clinic. In parti, sucking Eva Maxim's cock is the first test for the newborn bimbo.
Starring: Goddess Tangent, Eva Maxim
Genre: Shemale, Transsexual, Hardcore, Anal, Chastity, Femdom, Fetish, Forced Bi, Latex, Strapon, Sissy

Download: My TS Stepdaughter 5
Year Of Release: 2024
Starring: Eva Maxim, Brittney Kade, Kasey Kei, Cliff Jensen, Dillon Diaz, Draven Navarro
Genre: Shemale, Transsexual, Gonzo, Hardcore, Anal, Family Roleplay

Download: My TS Stepdaughter 4
Year Of Release: 2022
Starring: Saska Sage, Arabelle Raphael, Ava Holt, Izzy Wilde, Mimi Oh & Ana Foxxx
Genre: Shemale, Transsexual, Gonzo, Hardcore, Anal, Family Roleplay

Download: My TS Stepdaughter 3
Year Of Release: 2021
Starring: Crystal Thayer, Draven Navarro, Jade Venus, Jenna Gargles, Joanna Angel, Kate Zoha, Pierce Paris
Genre: Shemale, Transsexual, Gonzo, Hardcore, Anal, Family Roleplay

Download: My TS Stepdaughter 2
Year Of Release: 2019
Starring: Ella Hollywood, Eva Maxim, Ricky Larkin, Pierce Paris, Khloe Kay, Daisy Taylor
Genre: Shemale, Transsexual, Gonzo, Hardcore, Anal, Family Roleplay

Download: My TS Stepdaughter 1
Year Of Release: 2019
Starring: Khloe Kay, Colby Jansen, Jessy Dubai, Chelsea Poe, Wesley Woods, Dante Colle
Genre: Shemale, Transsexual, Gonzo, Hardcore, Anal, Family Roleplay

If you need a babysitter and you have a dark, kinky desire for Trannies, then let us help you out. What you really need is a Tranny Babysitter.
Starring: Jamie Paige, Carmen, Vanilla, Jessica Fox, Garmen Moor
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

I was wondering who the agency was sending as tonight's baby sitter when I heard a knock on the door and in walked the most gorgeous chick I'd ever seen. Pretty, built, great ass and a look in her eyes that said "Fuck Me!"
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen
Starring: Carmen Cruz , Olivia Love

So i’m sitting at home alone and i hear the doorbell. I open it and there’s the babysitter. I totally forgot that i promised to pay her today. Well i’m flat out of cash so i asked this little cutie if we can work something out.
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen
Starring: Ariel Everitts, Doll, Kelly Shore, Kimber James, Nicky

Boy, did I get a wrong number! The babysitter I called and hired for the night had to be the cutest chick I'd ever seen - with a body that started my balls boiling.
Starring: Natassia Dreams, Gia Darling (TS), Jessica Host (TS), La Cherry Spice (TS)
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

So the new babysitter shows up and she's gorgeous! Suddenly your dinner date can wait, you gotta check this chick out instead. Buddy, are you in for a Big surprise!
Starring: Foxxy, Holly Sweet, Keegan Voss, Jamie Page
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

Now that you're getting a little bit older and wiser you should probably settle down and forget about all those crazy years when you'd fuck anything that walked... Right? WRONG!!
Starring: Khloe Hart, Yasmin Lee, Gennesis, Karime Araugo
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen

What if a babysitter showed up and she was really fucking gorgeous? Looks like you're gonna be late for dinner, but you're also in for a surprise- because she's not a chick, this babysitter's a Tranny!
Starring: Jessica, Renata, Aubrey, Kimber James
Genre: Transsex, She Male, Anal, Shemale, Schoolgirl, Threesome, Hardcore, Blowjob, Oral, Teen