Becoming Femme Loading...

MILF Updates

Advanced Category Filter
Apply Filters Reset Filters

never too late to be a sissy princess

Featuring: Cheryl Summers
  • 183 Photos, 27:35
  • May 30, 2025
  • 4.0

parent teacher conference with a twist

Featuring: Cassandra Lovit
  • 167 Photos, 24:53
  • Nov 24, 2023
  • 4.6

pinup sissy adores her alpha master

Featuring: Vicky Fatale
  • 155 Photos, 26:07
  • Feb 3, 2023
  • 4.4

Pornhub crossdressing superstar visits the site

Featuring: Glamgurl XOXO
  • 58 Photos, 12:56
  • Oct 9, 2019
  • 4.6

Providing a Break from the Grind

Featuring: Akira Kristensen
  • 179 Photos, 26:35
  • Nov 29, 2024
  • 5.0

rewarded for doing all of her chores

Featuring: Slave Anna
  • 200 Photos, 30:18
  • May 15, 2022
  • 4.3

romantic date night with a beautiful crossdresser

Featuring: Jenna Jaden
  • 174 Photos, 25:52
  • Sep 15, 2019
  • 4.9

secret sissy gets caught crossdressing

Featuring: Heather Riggs
  • 161 Photos, 27:03
  • Jun 24, 2021
  • 4.7

seeing a new side of him

Featuring: Shawnee Gold
  • 194 Photos, 26:40
  • Nov 15, 2024
  • 5.0

she would wait for him until the end of time

Featuring: Cassandra Lovit
  • 161 Photos, 24:12
  • Jan 20, 2023
  • 4.5

she's excited about getting dicked down

Featuring: Jacquelyn James
  • 93 Photos, 19:04
  • Aug 23, 2018
  • 4.0

sissy maid does everything she is told

Featuring: Sissy Molly
  • 113 Photos, 18:56
  • May 9, 2018
  • 4.0

GET YOUR INSTANT ACCESS NOW FOR ALL THE FULL LENGTH VIDEOS!
TSPOV
Pure-TS