• Search: Dress Sissy
Panty Sissy and Big Chubby Bear Playing
9 years ago
6:59

TheGay

Panty Sissy and Big Chubby Bear Playing

Tags: bear, chubby, crossdressing, fetish, panties
Sissy in new dress and panties 4
2 years ago
4:15

GayCk

Sissy in new dress and panties 4

Tags: big cock, crossdressing, cumshot, dress, fetish
sissy crossdresser cumming in girdle and upskirt dress
5 years ago
2:21

YepTube

sissy crossdresser cumming in girdle and upskirt dress

Tags: crossdressing, cum, dress, girdle, upskirt
black Underpants Blue Sexy Dress Sissy biotch Crossdresser White Body Gay twink Hairless Yummy Skin Big Butt Big Ass Cute
2 years ago
15:56

GayBingo

black Underpants Blue Sexy Dress Sissy biotch Crossdresser White Body Gay twink Hairless Yummy Skin Big Butt Big Ass Cute

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Sissy Twerking Fat Ass In Dress
1 year ago
4:20

TheGay

Sissy Twerking Fat Ass In Dress

Tags: ass, dress, fat, hd, solo
Sissy Slut Sexy Dress Big Butt Crossdresser Solo Performing
1 year ago
10:12

TheGay

Sissy Slut Sexy Dress Big Butt Crossdresser Solo Performing

Tags: big ass, crossdressing, dress, feet, fetish
Top Brief Sexiest Parts Of Me Crossdresser Sissy Hoe White Enormous Caboose Arse Tranny Tranny Femboy
10 months ago
13:09

4Gay

Top Brief Sexiest Parts Of Me Crossdresser Sissy Hoe White Enormous Caboose Arse Tranny Tranny Femboy

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Sissy training
1 year ago
5:15

xHamster

Sissy training

Tags: anal, anal toying, ass, ass to mouth, grandpa
I wish I could dress like a sissy all the time
4 years ago
10:17

BoyFriendTV

I wish I could dress like a sissy all the time

Tags: crossdressing, dress, sissy
Sissy Crossdresser Bondage in Lycra Dress and Stockings 8
1 year ago
2:34

GayCk

Sissy Crossdresser Bondage in Lycra Dress and Stockings 8

Tags: big cock, cumshot, handjob, hd, twink
Pants Pink Dress Sexy Young Gay Crossdresser Sissy Big Butt Big Ass White Body Long Legs Lady Boy Girly Emo Boy
1 year ago
12:49

TheGay

Pants Pink Dress Sexy Young Gay Crossdresser Sissy Big Butt Big Ass White Body Long Legs Lady Boy Girly Emo Boy

Tags: dress, hd, solo, twink, webcam
Soft sissy Sadie in short red dress 5
1 year ago
5:13

GayCk

Soft sissy Sadie in short red dress 5

Tags: big cock, crossdressing, handjob, hunk, sissy
KinkyChrisX - Sissy play in pink
11 months ago
12:18

xHamster

KinkyChrisX - Sissy play in pink

Tags: ass, dick, solo, teen (18+), toys
Ass Fucking Have Fun - Sissy, Spandex and Sneak Faux-Cock
2 years ago
8:51

GayCk

Ass Fucking Have Fun - Sissy, Spandex and Sneak Faux-Cock

Tags: anal, assfucking, big cock, cumshot, rubber
Sissy Ray in Pink Satin Sissy Dress Kitchen Upskirt
5 years ago
3:13

TheGay

Sissy Ray in Pink Satin Sissy Dress Kitchen Upskirt

Tags: crossdressing, hd, solo, upskirt, voyeur
Sissy In Chastity And Pink Dress Filling Up Her Ass With Two Beers
1 year ago
4:17

TheGay

Sissy In Chastity And Pink Dress Filling Up Her Ass With Two Beers

Tags: ass, chubby, hd, redhead, sissy
Sissy Crossdresser Bondage in Lycra Dress and Stockings 9
1 year ago
2:36

GayCk

Sissy Crossdresser Bondage in Lycra Dress and Stockings 9

Tags: bdsm, big cock, bondage, crossdressing, cumshot
Sissy Wearing A Dress Masturbating With His Panties Down - Uekhui
1 year ago
5:04

TheGay

Sissy Wearing A Dress Masturbating With His Panties Down - Uekhui

Tags: hd, masturbation, sissy, solo, webcam
Dildo gagging sissy
11 months ago
5:06

xHamster

Dildo gagging sissy

Tags: blowjob, deep throat, dick, hardcore, hd
Black Underpants Blue Sexy Dress Sissy Slut Crossdresser White Body Gay Twink Hairless Yummy Skin Big Butt Big Ass Cute
2 years ago
15:47

TheGay

Black Underpants Blue Sexy Dress Sissy Slut Crossdresser White Body Gay Twink Hairless Yummy Skin Big Butt Big Ass Cute

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Asian sissy slut in maid dress
2 years ago
3:37

xHamster

Asian sissy slut in maid dress

Tags: barebacking, blowjob, cumshot, hd, twink
Sissy wearing a dress outdoors playing with a dildo
1 year ago
7:38

xHamster

Sissy wearing a dress outdoors playing with a dildo

Tags: anal, hd, outdoor, solo, sucking
Sissy in pink dress strokes her cock with cumshot on face
3 years ago
8:16

WinPorn

Sissy in pink dress strokes her cock with cumshot on face

Tags: cumshot, dick, dress, masturbation, sissy
Soft sissy Sadie in short red dress 2
3 years ago
5:15

GayCk

Soft sissy Sadie in short red dress 2

Tags: anal, big cock, crossdressing, cumshot, handjob
Pink Dress #2 xoxo sissy cd slut 2
3 years ago
1:21

GayCk

Pink Dress #2 xoxo sissy cd slut 2

Tags: anal, big cock, crossdressing, cumshot, fetish
Sissy Love - Dress'in Up (Amateur crossdresser PMV) 2
3 years ago
5:52

GayCk

Sissy Love - Dress'in Up (Amateur crossdresser PMV) 2

Tags: anal, barebacking, big cock, blowjob, crossdressing
Sissy Love - Dressin Up Fledgling crossdresser PMV
3 years ago
5:52

GayCk

Sissy Love - Dressin Up Fledgling crossdresser PMV

Tags: big cock, blowjob, crossdressing, dress, sissy
Sissy Love - Dress'in Up (Amateur crossdresser PMV) 4
3 years ago
5:49

GayCk

Sissy Love - Dress'in Up (Amateur crossdresser PMV) 4

Tags: anal, barebacking, big cock, blowjob, crossdressing
Sissy Crossdresser Trans Femboy Cums Sucks And Moans In Striped Dress
2 years ago
7:39

TheGay

Sissy Crossdresser Trans Femboy Cums Sucks And Moans In Striped Dress

Tags: brunette, cum, hd, solo, sucking
Sissy Enjoy - Dressin Up First-Timer crossdresser PMV
3 years ago
5:49

GayCk

Sissy Enjoy - Dressin Up First-Timer crossdresser PMV

Tags: anal, barebacking, big cock, blowjob, crossdressing
Shiny Satin Sissy Wearing Polka Dot Dress
6 years ago
9:48

xHamster

Shiny Satin Sissy Wearing Polka Dot Dress

Tags: dress, hd, satin, sissy
Skinny Sissy Crossdresser Dirty Talk And Huge Cum Load On Black Dress With White Medical Gloves
2 years ago
9:04

TheGay

Skinny Sissy Crossdresser Dirty Talk And Huge Cum Load On Black Dress With White Medical Gloves

Tags: big cock, black, cum, cumshot, fetish
Sissy Crossdresser Bondage in Lycra Dress and Stockings 4
3 years ago
2:39

GayCk

Sissy Crossdresser Bondage in Lycra Dress and Stockings 4

Tags: bdsm, big cock, bondage, crossdressing, cumshot
Sissy Crossdresser Bondage in Lycra Dress and Stockings 3
3 years ago
2:35

GayCk

Sissy Crossdresser Bondage in Lycra Dress and Stockings 3

Tags: bdsm, big cock, bondage, crossdressing, cumshot
Sissy Love - Dress'in Up (Amateur crossdresser PMV) 5
3 years ago
5:51

GayCk

Sissy Love - Dress'in Up (Amateur crossdresser PMV) 5

Tags: anal, barebacking, big cock, blowjob, crossdressing
Sissy smoking outdoors in sexy dress
7 years ago
4:14

xHamster

Sissy smoking outdoors in sexy dress

Tags: crossdressing, dick, outdoor, sissy, striptease
Sissy in gold dress fucked
5 years ago
12:01

TheGay

Sissy in gold dress fucked

Tags: blowjob, chubby, fantasy, sissy, small cock
Hot Sissy Crossdresser Femboy In Red Hot Apron Dress
2 years ago
10:35

TheGay

Hot Sissy Crossdresser Femboy In Red Hot Apron Dress

Tags: brunette, crossdressing, hd, solo, webcam
Sissy in a tight dress shakes his girly bottom.
7 years ago
0:28

xHamster

Sissy in a tight dress shakes his girly bottom.

Tags: crossdressing, dress, hd, sissy, tight
Leather Dress, Overknee High Heels Stiletto Boots Sissy
2 years ago
5:36

TheGay

Leather Dress, Overknee High Heels Stiletto Boots Sissy

Tags: latex, sissy, solo, teen (18+), webcam
SISSY DRESSED IN A SUNDRESS JACKING WITH HIS UNDIES DOWN - UEKHUI
2 years ago
5:29

GayCk

SISSY DRESSED IN A SUNDRESS JACKING WITH HIS UNDIES DOWN - UEKHUI

Tags: big cock, crossdressing, cumshot, dick, fetish
Diaper Sissy In A Red Dress
2 years ago
5:13

TheGay

Diaper Sissy In A Red Dress

Tags: crossdressing, diaper, dress, sissy, solo
I like to dress like a sissy, and taking a hard cock
7 years ago
9:31

JizzBunker

I like to dress like a sissy, and taking a hard cock

Tags: big cock, dick, hd, latina, masturbation
Horny Sissy In Red Dress And Panties Ryan743 With Anal Toy
3 years ago
6:23

TheGay

Horny Sissy In Red Dress And Panties Ryan743 With Anal Toy

Tags: crossdressing, solo, tattoo, toys, webcam
Sissy Rails a Absorption Bouncy Rectal Buttplug
3 years ago
7:16

GayCk

Sissy Rails a Absorption Bouncy Rectal Buttplug

Tags: anal, ass, big cock, crossdressing, cumshot
Humid Latex Sissy Stroking in Bathroom
3 years ago
4:12

GayCk

Humid Latex Sissy Stroking in Bathroom

Tags: big cock, crossdressing, cumshot, dick, fetish
Sissy Crossdresser - Big White Ass Boy Gay Slut Jeans Dress
5 months ago
6:05

UPornia

Sissy Crossdresser - Big White Ass Boy Gay Slut Jeans Dress

Tags: big ass, boy, crossdressing, dress, jeans
Anal Cunt Sissy slut dress up pleasure
4 months ago
10:11

xHamster

Anal Cunt Sissy slut dress up pleasure

Tags: american, anal, ass, crossdressing, dildo
Sissy Crossdresser Bondage in Lycra Dress and Stockings3333
5 months ago
2:36

MenGem

Sissy Crossdresser Bondage in Lycra Dress and Stockings3333

Tags: bdsm, bondage, crossdressing, dress, hd
Soft sissy Sadie in short red dress 4
1 year ago
5:15

GayCk

Soft sissy Sadie in short red dress 4

Tags: anal, big cock, crossdressing, cumshot, fetish
Pink Dress #2 xoxo sissy cd slut 6
1 year ago
1:24

GayCk

Pink Dress #2 xoxo sissy cd slut 6

Tags: big cock, crossdressing, cumshot, fetish, hairy
Sissy in new dress and panties
2 years ago
4:15

MenGem

Sissy in new dress and panties

Tags: crossdressing, dress, panties, sissy, solo
Sissy Love - Dressin Up Amateur crossdresser PMV
2 years ago
5:50

MenGem

Sissy Love - Dressin Up Amateur crossdresser PMV

Tags: big cock, blowjob, compilation, crossdressing, cumshot
You are privileged to be my dedicated sissy dress-up doll
9 months ago
6:11

GayBingo

You are privileged to be my dedicated sissy dress-up doll

Tags: bdsm, bisexual, crossdressing, doll, dress
Sissy dress, gay dress, gay sissies
2 years ago
5:18

GayBingo

Sissy dress, gay dress, gay sissies

Tags: dress, sissy
Sissy Crossdresser Bondage in Lycra Dress and Stockings
2 years ago
2:36

MenGem

Sissy Crossdresser Bondage in Lycra Dress and Stockings

Tags: bdsm, bondage, crossdressing, dress, homevideo
sissy kathys wedding dress wank
4 years ago
8:11

BoyFriendTV

sissy kathys wedding dress wank

Tags: anal, bdsm, crossdressing, dress, masturbation
sissy kathys wedding dress wank
3 years ago
8:07

BoyFriendTV

sissy kathys wedding dress wank

Tags: anal, bdsm, crossdressing, dress, masturbation
Sissy Love - Dress'in Up (Amateur crossdresser PMV)
3 years ago
5:52

BoyFriendTV

Sissy Love - Dress'in Up (Amateur crossdresser PMV)

Tags: big cock, blowjob, crossdressing, dress, sissy
Sissy Kathys Wedding Sundress Masturbate
8 months ago
8:12

4Gay

Sissy Kathys Wedding Sundress Masturbate

Tags: anal, bdsm, crossdressing, dress, handjob
Soft sissy sadie in short red dress
10 months ago
5:13

BoyFriendTV

Soft sissy sadie in short red dress

Tags: crossdressing, dress, sissy, small cock
Sissy abased, slurps spunk and uses vibe
7 months ago
13:01

4Gay

Sissy abased, slurps spunk and uses vibe

Tags: abuse, crossdressing, cum, cumshot, dress
Dress up in these panties like a submissive sissy
8 months ago
6:30

GayBingo

Dress up in these panties like a submissive sissy

Tags: bdsm, bisexual, crossdressing, dress, panties
Pink Dress #2 xoxo sissy cd slut 4
1 year ago
1:21

GayCk

Pink Dress #2 xoxo sissy cd slut 4

Tags: big cock, crossdressing, cumshot, dress, fetish
Sissy in new dress and panties 7
1 year ago
4:18

GayCk

Sissy in new dress and panties 7

Tags: big cock, crossdressing, cumshot, dress, fetish
White Sissy In Red Dress Trains Her Pussy On Fk Machine (pt2)
1 year ago
5:16

xHamster

White Sissy In Red Dress Trains Her Pussy On Fk Machine (pt2)

Tags: anal, anal toying, boy, canadian, crossdressing
Black Dress Sissy Machine Fuck
1 year ago
6:59

TheGay

Black Dress Sissy Machine Fuck

Tags: black, brunette, crossdressing, dress, hd
Caged Sissy Toying Herself In A Cute Dress
1 year ago
7:38

TheGay

Caged Sissy Toying Herself In A Cute Dress

Tags: brunette, cute, dress, hd, sissy
Sissy in new dress and panties 9
1 year ago
4:21

GayCk

Sissy in new dress and panties 9

Tags: big cock, crossdressing, cumshot, dress, fetish
Pants Pink Dress Sexy Sissy Crossdresser Big White Ass Slut Gay
1 year ago
12:27

TheGay

Pants Pink Dress Sexy Sissy Crossdresser Big White Ass Slut Gay

Tags: big ass, chubby, crossdressing, dress, hd
Sissy Crossdresser Sexy Dress Big Ass White Lady Boy Sexy Model - Gay Boy
1 year ago
10:22

TheGay

Sissy Crossdresser Sexy Dress Big Ass White Lady Boy Sexy Model - Gay Boy

Tags: ass, big ass, boy, crossdressing, dress
I Dress Like A Sissy To Fuck My Ass Hole
1 year ago
9:49

TheGay

I Dress Like A Sissy To Fuck My Ass Hole

Tags: ass, dress, hd, sissy, solo
Sissy Wearing A Dress And Pantyhose Masturbating His Asshole - Uekhui
2 years ago
5:09

TheGay

Sissy Wearing A Dress And Pantyhose Masturbating His Asshole - Uekhui

Tags: ass, dress, hd, masturbation, pantyhose
Sissy Wearing A Dress And Red Stockings Jerking Off His Cock - Uekhui
1 year ago
5:06

TheGay

Sissy Wearing A Dress And Red Stockings Jerking Off His Cock - Uekhui

Tags: brunette, dick, dress, hd, jerking
Sissy Wearing A Dress And White Pantyhose Wanking Lying Down - Uekhui
1 year ago
5:59

TheGay

Sissy Wearing A Dress And White Pantyhose Wanking Lying Down - Uekhui

Tags: big cock, brunette, crossdressing, dress, hd
Pink Dress #2 xoxo sissy cd slut 3
2 years ago
1:24

GayCk

Pink Dress #2 xoxo sissy cd slut 3

Tags: big cock, crossdressing, cumshot, dress, fetish
Sissy Wearing Black Dress And Red Pantyhose Wanking On The Bed - Uekhui
2 years ago
5:02

TheGay

Sissy Wearing Black Dress And Red Pantyhose Wanking On The Bed - Uekhui

Tags: bed sex, black, dress, hd, pantyhose
Sissy Crossdresser Bondage in Lycra Dress and Stockings 7
1 year ago
2:36

GayCk

Sissy Crossdresser Bondage in Lycra Dress and Stockings 7

Tags: bdsm, big cock, bondage, crossdressing, cumshot
Pink Dress #2 xoxo sissy cd slut
2 years ago
1:23

FetishPapa

Pink Dress #2 xoxo sissy cd slut

Tags: crossdressing, dress, sissy, slut, twink
Peter Went diapered sissy in pretty red dress
5 years ago
6:14

TheGay

Peter Went diapered sissy in pretty red dress

Tags: crossdressing, diaper, dress, masturbation, pretty