Sort by
Relevancy

Most Relevant 'sissy mature outdoor' Porn Videos

Big Preview Date Added 2018-07-14

6Videos

50%
Play All Visit playlist

by: NORTY BOI

Black sissy humped outdoor

50%
Big Preview Date Added 2023-06-09

32Videos

50%
Play All Visit playlist

by: xcdf234

Sissy,Mature

50%
Big Preview Date Added 2019-11-08

46Videos

50%
Play All Visit playlist

by: belgianbi89

Mature

50%
Big Preview Date Added 2020-07-28

11Videos

50%
Play All Visit playlist

by: wiesbalu

Outdoor

50%
Big Preview Date Added 2024-01-10

23Videos

50%
Play All Visit playlist

by: Dethklok89

Outdoor public

50%
Big Preview Date Added 2024-04-15

14Videos

50%
Play All Visit playlist

by: Culonero 🐻

Mature

50%
Big Preview Date Added 2019-01-01

86Videos

91%
Play All Visit playlist

by: Helena Blow

Sissy / Crossdresser

91%
Big Preview Date Added 2020-03-31

43Videos

100%
Play All Visit playlist

by: AndreeaLuv

Sissy Femboi Fucked

100%
Big Preview Date Added 2021-04-22

52Videos

100%
Play All Visit playlist

by: zaddy10

SISSY WHITE BITCHES

100%
Big Preview Date Added 2021-09-21

1Videos

50%
Play All Visit playlist

by: theangel0

Sissy - CD

50%
Big Preview Date Added 2022-09-13

16Videos

100%
Play All Visit playlist

by: Kira Kay

Sissy Hypno

100%
Big Preview Date Added 2023-04-01

19Videos

100%
Play All Visit playlist

by: Swedass

Sissy

100%
Big Preview Date Added 2023-08-25

333Videos

100%
Play All Visit playlist

by: Roadmaster1982

Traps , Femboys and Sissy sluts

100%
Big Preview Date Added 2023-09-06

14Videos

100%
Play All Visit playlist

by: cutiepantie

Italian sissy

100%
Big Preview Date Added 2023-10-30

3Videos

50%
Play All Visit playlist

by: C53M23

Sissy - Deepthroat

50%
Big Preview Date Added 2023-10-30

33Videos

100%
Play All Visit playlist

by: C53M23

Sissy - Creampie_CUM_Facial_Swallow

100%
Big Preview Date Added 2023-10-30

8Videos

50%
Play All Visit playlist

by: C53M23

Sissy - Bareback

50%
Big Preview Date Added 2023-10-30

1Videos

50%
Play All Visit playlist

by: C53M23

Sissy - BBC - BNWO -Breeding

50%
Big Preview Date Added 2024-05-08

25Videos

50%
Play All Visit playlist

by: OKD

sissy

50%
Big Preview Date Added 2024-05-27

6Videos

50%
Play All Visit playlist

by: Iluvsissies

Hot Sissy Crossdressers Love making

50%
Big Preview Date Added 2021-10-03

18Videos

100%
Play All Visit playlist

by: BlueGirl70

BlueGirl70 Sploshing Moments

100%
Big Preview Date Added 2022-08-24

14Videos

100%
Play All Visit playlist

by: NicSteph

outside playtime

100%
Big Preview Date Added 2023-04-21

3Videos

100%
Play All Visit playlist

by: baksbaks87

Assfuck

100%
Big Preview Date Added 2020-03-22

10Videos

100%
Play All Visit playlist

by: Sneakapeek509

Mature sissy

100%
Big Preview Date Added 2023-01-24

105Videos

50%
Play All Visit playlist

by: kassandrita

Mature sissy highheels

50%
Big Preview Date Added 2023-10-12

26Videos

50%
Play All Visit playlist

by: gruisuil

Mature sissy

50%
Big Preview Date Added 2023-11-09

11Videos

50%
Play All Visit playlist

by: bernard53

Mature sissy slut

50%
Big Preview Date Added 2024-01-20

5Videos

50%
Play All Visit playlist

by: debby CD

mature CD and young sissy

50%
Big Preview Date Added 2024-01-25

6Videos

50%
Play All Visit playlist

by: gruisuil

Young Man Mature Sissy

50%
Big Preview Date Added 2024-02-18

22Videos

50%
Play All Visit playlist

by: GilMilAunTgPies

Size Queens role models

50%
Big Preview Date Added 2024-02-18

135Videos

50%
Play All Visit playlist

by: GilMilAunTgPies

Stuff I miss doing or having done too me

50%
Big Preview Date Added 2024-02-20

80Videos

50%
Play All Visit playlist

by: GilMilAunTgPies

Lady role models

50%
Big Preview Date Added 2024-05-14

9Videos

50%
Play All Visit playlist

by: Tutim99

mature sissy

50%
Big Preview Date Added 2017-07-20

87Videos

80%
Play All Visit playlist

by: DvddyVirgo

Traps/sissies

80%
Big Preview Date Added 2017-05-29

7Videos

50%
Play All Visit playlist

by: klisse

outdoor

50%
Big Preview Date Added 2017-06-20

0Videos

50%
Play All Visit playlist

by: byshemale

outdoor

50%
Big Preview Date Added 2017-07-15

23Videos

66%
Play All Visit playlist

by: dformation

outdoor fuckiing & oil

66%
Big Preview Date Added 2017-07-16

12Videos

66%
Play All Visit playlist

by: Blkmoon23

Outdoor

66%
Big Preview Date Added 2017-08-02

229Videos

83%
Play All Visit playlist

by: fascinate68

Outdoor

83%
Big Preview Date Added 2017-08-10

2Videos

62%
Play All Visit playlist

by: miteryon321

OUTDOOR

62%
Big Preview Date Added 2017-08-13

72Videos

57%
Play All Visit playlist

by: xetalon

outdoor

57%
Big Preview Date Added 2017-08-18

6Videos

61%
Play All Visit playlist

by: 88xbox

Outdoor / Public

61%
Big Preview Date Added 2017-08-26

22Videos

66%
Play All Visit playlist

by: pkb.sissyslut.whore

shemale on sissy, sissy on sissy... god sissify me NOW BASTARDS

66%
Big Preview Date Added 2017-08-30

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/3704/chap-fucks-pretty-blond-tgirl-outdoor/?pl=192287

50%
Big Preview Date Added 2017-08-30

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/10178/outdoor-sex-with-a-leggy-vamp/

50%
Big Preview Date Added 2017-08-30

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/42928/naughty-tranny-ass-fucked-hard-outdoor/

50%
Big Preview Date Added 2017-08-30

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/2582/mutual-sex-with-a-burning-ts-outdoor/

50%
Big Preview Date Added 2017-08-30

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/181491/curly-brunette-tranny-outdoor-fuck/

50%
Big Preview Date Added 2017-08-30

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/3885/shemale-and-dude-fucks-outdoor/

50%
Big Preview Date Added 2017-09-05

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/46555/outdoor-foursome-poolside/

50%
Big Preview Date Added 2017-09-05

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/53120/hot-outdoor-scene/

50%
Big Preview Date Added 2017-09-08

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/269095/outdoor-fuck/

50%
Big Preview Date Added 2017-09-09

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/44835/teen-isabella-in-outdoor-fucking-scene-with-alex/

50%
Big Preview Date Added 2017-09-09

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/5500/dude-drills-latina-shemale-outdoor/

50%
Big Preview Date Added 2017-09-09

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/40479/tranny-nun-gets-banged-outdoor/

50%
Big Preview Date Added 2017-09-09

2Videos

50%
Play All Visit playlist

by: DOMINADOR

https://www.ashemaletube.com/videos/16062/trio-fucking-outdoor/

50%