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

Sissy

142 videos

13:40 HD
Ochani Gets Drilled By The Fucking Machine
67 views
7:09 HD
Pegged Good Boy Gets Mommy Countdown
172 views
77:00
Syren De Mer Humiliates Her Locked Hubby While Taking A Creampie
111 views
58:00
Sissy Husband Eats BBC Creampie While Caged
192 views
70:00
Blonde Domme Forces Hubby To Clean Up Her Gangbang
258 views
6:00 HD
Sissy Gets Paddled And Fisted By A Trio Of Dommes
116 views
38:00
Kagney Linn Karter Sissy Hypnosis And Cock Worship
178 views
68:00
Courtney Taylor Cucks Her Sissy Husband With Johnny Love's Big Cock
178 views
2:26 HD
Mimi Bonano Takes Her Big Black Toy Deep
16 views
7:23 HD
Domina Fire Punishes Her Bound Submissive
24 views
1:06 HD
Jude Lynx Begs For Huge Cock To Destroy Her
15 views
10:59 HD
Mistress Leila Punishes Hund In Fishnet Bodysuit
13 views
7:45 HD
NicollyVentura Pegs Her Tiny Cousin Hard
43 views
4:42 HD
Alia Malia Takes Me From Behind In POV
13 views
4:14 HD
Mulberry212 Makes Her Boyfriend Her Girlfriend And Pegs Him Rough
18 views
14:24 HD
RyuDoll Lets The Machine Fuck Her Ass
20 views
8:20 HD
Missangell177 Takes Daddy's Cock In Her Tight Hole
10 views
2:13 HD
Sasha Self Shows Her Femboy Self Suck And Self Fuck Skills
25 views
10:20 HD
Melody Fluffington Cleans His Cock And Swallows Anal Creampies
88 views
15:03 HD
Cosmicbroccoli's Pegging And Fisting Toy Box
27 views
9:06 HD
Born To Peg Puts Him In Latex And Pegs His Tiny Cock
35 views
33:47 HD
ToolChannel Gets Off With Anal And Hand Action
19 views
11:25 HD
Prettyboi2000x Gets Pounded By Her College Professor
27 views
12:04 HD
Leashed Cat Girl Gets Owned Rough By Tgirl Cailey Katts
2 views
7:12 HD
Born To Peg Gives Him A Messy Prostate Massage
26 views
14:56 HD
Rika Fox Gets Hammered By Black Cock
2 views
4:24 HD
Cassie Skanenborg Plays With Toys And Covers Her Face In Cum
13 views
12:15 HD
Cute Slut Takes A Hard Pounding From Her Lover
18 views
8:56 HD
Couple Of Loverss Takes Control In Passionate Pegging
21 views
6:26 HD
My Mistress Makes Her Boyfriend Take Her Strap-On
12 views
5:00 HD
Domina Emily Locks Sissy Justin In His Tiny Chastity Cage
20 views
14:00 HD
Tiny Asian Babe Gets Her Panties Torn And Fucked Raw Twice
20 views
0:29 HD
Big Tits Simone Steele Takes Boswell Black's Cock Deep
22 views
0:29 HD
Simone Steele And Rico Shades Go Ass To Mouth
12 views
20:00 HD
Sanj And Friends Blast Loads All Over Their Horny Stepsister's Face
38 views
27:00 HD
Sissy Slut Gets His Ass Destroyed By Dominant Mistress
73 views
2:00 HD
Emme White Rams A Bat Deep In His Boy Pussy
9 views
22:00 HD
Oiled Up Old Lady Gets Her Ass Pounded Like A Sissy Maid
11 views
7:00 HD
JuliaSoftdome And SilentS Make You Beg For It
37 views
10:00 HD
Polysweet And Pau1sweet Destroy A Chump With A Strapon
19 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.