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All models were 18 years of age or older at the time of depiction.

Sissy

142 videos

5:34 HD
Yanasissy21 Mounts a Big Purple Dildo Like a Good Sissy Cow
4 views
7:56 HD
Feminized Femboy SashaDeSissy Pissing In Chastity
8 views
2:42 HD
Chubby Sissy Mollybabygurl Morning Routine With Butt Plug And Chastity Cage
8 views
3:51 HD
Crossdresser olesyaslave Locked in Chastity Belt Shows Off Butt Plug
2 views
5:24 HD
Pegged My Sissy Good With FemForHer Strapon
30 views
2:00 HD
Lana Rhoades Owns Keiran Lee On And Off The Court
26 views
3:00 HD
Whiteboi Staci Thorn Gets BBC Discipline From Rico Strong
28 views
7:00 HD
Emily Candys And Justin Sweetsun Get Kinky With A Ruined Prostate Massage
21 views
3:00 HD
Caged Sissy Berlin Gets Mercilessly Used By Lady Blackdiamoond
5 views
8:00 HD
Sissy Boy Gets Fucked Raw And Fisted By Goth Mistress
157 views
12:00 HD
Mature Sissy Gets Her Hairy Pussy Eaten By Teen Alyssa Bounty
163 views
3:15 HD
Sissy Hazel The Goth Mistress Electrifies Her Slave
24 views
6:09 HD
Locked Sissy LevkoNoya Squirts Hard on Huge Dildo and Ruins Her Hole with Plug
5 views
5:51 HD
ChiseCat Gets Off With A Onahole Toy
28 views
11:02 HD
Shenhunk Gets A Spooky Sissy Treat
15 views
7:08 HD
Born To Peg Makes Her Sissy Boyfriend Beg For It
45 views
14:32 HD
Michelle Flowers Gets Her Sissy Anal Trained
15 views
10:00 HD
Locked Sissy Emily Candys Takes A Public Pee Humiliation
27 views
13:00 HD
Sissy Husband Gets Pegged And Licked Clean By His Wife
14 views
33:00 HD
Older Sissy Roxy Risingstar And Nikki Nuttz Get Their Holes Devoured By Young Studs
20 views
44:00 HD
Slim Poke And River Lynn Get Used By Marcelo While Her Locked Hubby Watches
48 views
12:00 HD
Sissy Husband Locked Up After Public Cock Sucking
12 views
8:22 HD
Chastity Charli Convulses Under A Relentless Anal Machine
74 views
11:07 HD
Yourprettykate Gets Off On The Couch With A Toy
105 views
13:35 HD
Natalia Winter Fucks A Femboy Spider Lover
71 views
14:09 HD
Veronica Taboo Stuffs Every Toy Inside Her Sissy Hole
40 views
1:10 HD
Redhead Domme Fucks Her Locked Sissy Boyfriend
149 views
2:00 HD
August Taylor Cucks Her Sissy Man And Feeds Him Cum
159 views
15:00 HD
Femboy Gets His Asshole Wrecked By His Mistress
141 views
15:00 HD
Lady Julina Dominates Her Sissy Slut With A Giant Strap
153 views
1:35 HD
Jodie Taylor's Cuckold Command And Sissy Humiliation
286 views
17:00 HD
Jessica Starling Teaches Sissy Sluts With Her Strap-On
204 views
41:00 HD
Sissy Bimbo Gets Hypnotized And Trained For Cock
188 views
1:38 HD
Caged and Dripping a Little Pee LevkoNoya Femboy Trans Sissy Homemade
6 views
2:23
SusyTrav And AnalQueen Get Fisted And Covered By An Older Daddy
13 views
7:31 HD
Hornyproductions69 Gets Pegged Compilation Mix
8 views
41:17 HD
Jules Verne Anal Prince Stretches His Hole On A Giant Dildo
10 views
12:28 HD
Stockings and Chastity Belt Make Femboy alizevolter Cum
15 views
10:00 HD
Sissy Martin Gets Pegged By Dominatrix Eva Until He Cums Hands-Free
16 views
16:00 HD
FayGrey Puts Hinata Through Intense Assplay Training While Locked In Chastity
18 views

Sissy on LetMeJizz

The line from plain crossdressing is the submission, here a feminized man gets trained, dominated and made to serve rather than simply dressed up. Lingerie, makeup and obedience drive the scenes, the humiliation of being turned soft and used carrying more weight than the outfit.

142 sissy videos here, all HD and all free. New ones go up daily, so check back if you don't find your scene first time around.