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Search » Sissy Crossdresser Videos » (146)

2025-03-27 23:38:16

HClips

9:32

Sissy Slut in White Skirt and Riding Her Asshole

Sissy Slut in White Skirt and Riding Her Asshole

2025-05-20 09:15:27

xHamster

4:04

Horny Mature Sissy Fucks With Her Stepson In The Bedroom While Her Husband Is At Work

Horny Mature Sissy Fucks With Her Stepson In The Bedroom While Her Husband Is At Work

2025-04-27 21:18:25

TXXX

0:39

Everyone Has A Plan - Prison Of Sissy

Everyone Has A Plan - Prison Of Sissy

2025-05-13 09:10:30

xHamster

6:19

Domina humiliates small male pole crossdresser with fem clothes

Domina humiliates small male pole crossdresser with fem clothes

2024-09-22 21:59:11

Xozilla

5:00

'Feminized Sissy live return Femdom Mistress cuck dominated humiliated fuck peg cbt femboy cuck. Pt 3'

'Feminized Sissy live return Femdom Mistress cuck dominated humiliated fuck peg cbt femboy cuck. Pt 3'

2024-05-27 17:40:08

RedTube

25:56

Sissy Slut And Sissy Slave - Milked & Bred: Femdom Mistress Stellina Obscura Turns Husband Into Hucow 4 Anal Pegging

Sissy Slut And Sissy Slave - Milked & Bred: Femdom Mistress Stellina Obscura Turns Husband Into Hucow 4 Anal Pegging

2025-03-14 20:30:21

HotMovs

8:08

Young Sissy Boy Slut in Latex Pegging by Mistress

Young Sissy Boy Slut in Latex Pegging by Mistress

2025-05-18 21:15:28

xHamster

7:05

Sissy Talk: My Intimate Experience with a Mature Man + Tips for Good Girls

Sissy Talk: My Intimate Experience with a Mature Man + Tips for Good Girls

2025-05-08 21:09:29

xHamster

5:31

PREVIEW Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

PREVIEW Your Lesbian Wife Turns You Into a Woman - Clara Dee POV Virtual Sex Sissy Pegging

2025-04-18 21:09:03

PornHub

0:31

Bailey Wilde And Cassidy Cream In Dominatrix Fucks Hot Crossdresser In Chastity 9 Min

Bailey Wilde And Cassidy Cream In Dominatrix Fucks Hot Crossdresser In Chastity 9 Min

2025-05-07 11:48:18

HClips

8:16

Fucking Super Sexy Mexican Sissy - Compilation 5

Fucking Super Sexy Mexican Sissy - Compilation 5

2025-05-24 21:16:29

xHamster

8:12

Curvy Crossdresser Sucking and Fucking 33cm dildo

Curvy Crossdresser Sucking and Fucking 33cm dildo

2025-05-08 21:09:29

xHamster

5:26

Sissy dildo ride

Sissy dildo ride

2025-04-29 21:02:19

xHamster

5:05

Sissy failed edging

Sissy failed edging

2025-05-17 21:14:21

xHamster

1:27

My Sissy Lace Panty Skirt

My Sissy Lace Panty Skirt

2025-04-30 09:02:25

xHamster

1:32

Crossdresser With Big Tits Jerks Off Her Cock

Crossdresser With Big Tits Jerks Off Her Cock

2025-05-02 23:47:16

HClips

9:30

Cuckolds Secrets - Sissy Husband Watcjug Wife Sucking

Cuckolds Secrets - Sissy Husband Watcjug Wife Sucking

2025-03-22 23:37:11

HClips

8:27

'Geordie Slag Sissy Just Back From The Newcastle Football Match'

'Geordie Slag Sissy Just Back From The Newcastle Football Match'

2024-02-18 15:23:07

RedTube

5:05

Hottest Blonde Milf Turns Guy Into Sissy 6 Min With Justin Sweetsun And Emily Candys

Hottest Blonde Milf Turns Guy Into Sissy 6 Min With Justin Sweetsun And Emily Candys

2025-04-21 23:45:11

HClips

5:30

'Crossdresser guy strapon fucked by doms'

'Crossdresser guy strapon fucked by doms'

2023-04-14 00:00:00

RedTube

4:10

'Shy Crossdresser tries Anal and her Cum for the First Time'

'Shy Crossdresser tries Anal and her Cum for the First Time'

2024-05-16 05:30:08

RedTube

10:35

Blake DeBarge - PAWG Sluts and Sissy With BBC - Promo

Blake DeBarge - PAWG Sluts and Sissy With BBC - Promo

2025-04-30 21:36:14

xVideos

12:58

'JennStarXXX - Crossdresser webcum show'

'JennStarXXX - Crossdresser webcum show'

2024-02-16 03:22:17

RedTube

12:16

2025-04-30 21:06:24

xHamster

4:06

Femdom Handjob For Sissy Twink Boy

Femdom Handjob For Sissy Twink Boy

2025-05-12 23:54:15

HClips

5:59

18 Years old Femboy Ass Orgasm fuck with carrot Anal sissy sex

18 Years old Femboy Ass Orgasm fuck with carrot Anal sissy sex

2025-03-13 20:41:16

xHamster

7:57

Eating pussy while fuck machine is pegging chastity sissy ass promo

Eating pussy while fuck machine is pegging chastity sissy ass promo

2025-02-28 20:40:19

PornHub

0:56

ohww... Blake is Loving Me So Much - The Lust of Sissy Boy Saga

ohww... Blake is Loving Me So Much - The Lust of Sissy Boy Saga

2025-03-02 08:30:11

xHamster

10:20

Sissy has the hole ready for daddy to have fun with the

Sissy has the hole ready for daddy to have fun with the

2025-04-22 09:04:25

xHamster

6:50

Teaching my SISSY to PISS in a bowl and rewarding his MOUTH with my GOLDEN nectar

Teaching my SISSY to PISS in a bowl and rewarding his MOUTH with my GOLDEN nectar

2025-02-25 20:42:13

PornHub

6:15

Sissy Riley in the Sunshine ????????????????

Sissy Riley in the Sunshine ????????????????

2025-03-06 08:43:13

PornHub

15:53

Sissy Dream is Getting Bored (Game)

Sissy Dream is Getting Bored (Game)

2025-02-17 08:19:10

xHamster

13:00

Locked Sissy Training By Mistress With Ruined Cumshot

Locked Sissy Training By Mistress With Ruined Cumshot

2025-03-14 23:34:18

HClips

5:49

SISSY ADVENTURE - FULL MOVIE (The Best Hardcore Rought Anal Pegging)

SISSY ADVENTURE - FULL MOVIE (The Best Hardcore Rought Anal Pegging)

2025-04-07 20:54:20

xHamster

1:09:55

Sissy dick play, fisting, big toy

Sissy dick play, fisting, big toy

2025-04-19 21:09:10

PornHub

7:56

Chubby dilf gives sissy boy dildo instructions PREVIEW

Chubby dilf gives sissy boy dildo instructions PREVIEW

2025-03-06 08:43:13

PornHub

2:19

Parking lot jerk off while dressed as a sissy slut

Parking lot jerk off while dressed as a sissy slut

2025-03-06 08:33:11

xHamster

5:16

Trixy Sissy Babe as a Slut Welcomes You in a Hotel

Trixy Sissy Babe as a Slut Welcomes You in a Hotel

2025-04-16 20:59:20

xHamster

2:22

BBC fucks the cum out of older white sissy.

BBC fucks the cum out of older white sissy.

2025-02-19 20:19:10

xHamster

3:31

My Competitor Erica - Sissy Dream

My Competitor Erica - Sissy Dream

2025-03-14 08:42:20

xHamster

11:23

SISSY ADORANDO MEUS P&Eacute_S ENQUANTO EU FUMO E BEBO UMA CERVEJA

SISSY ADORANDO MEUS P&Eacute_S ENQUANTO EU FUMO E BEBO UMA CERVEJA

2025-03-23 09:22:12

xVideos

5:19

Sissy Is Alone Under the Influence

Sissy Is Alone Under the Influence

2025-03-04 08:32:14

xHamster

1:12

Sissy Was Shocked At The Size The Mistress Was Going To Shove Up Her Ass - Sissy Crossdresser, Sissy Slut And Rubber Slave

Sissy Was Shocked At The Size The Mistress Was Going To Shove Up Her Ass - Sissy Crossdresser, Sissy Slut And Rubber Slave

2025-03-24 21:05:14

TXXX

3:05

Sissy Crossdresser - 20 Year Old Trans Girl Sucking A Married Straight Guys Cock

Sissy Crossdresser - 20 Year Old Trans Girl Sucking A Married Straight Guys Cock

2025-02-18 23:03:16

HClips

12:21

Sissy hot timeline

Sissy hot timeline

2025-02-18 20:19:10

xHamster

6:47

First Spanking Of The Year -wife And Sissy Husband

First Spanking Of The Year -wife And Sissy Husband

2025-02-15 23:01:12

HClips

6:54

Your Sissy's Jerking for You

Your Sissy's Jerking for You

2025-02-16 20:19:06

xHamster

2:46

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