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Sissy: 4177 Videos, grouped by Popularity

Hot Passable Crossdresser Fucks Sexy Babe Hard
11:33

Hot Passable Crossdresser Fucks Sexy Babe Hard

Sissy Vickie Fucks Her Throat and Sprays Her Face
15:03

Sissy Vickie Fucks Her Throat and Sprays Her Face

MILF giving a hot Crossdresser Good Oral
04:16

MILF giving a hot Crossdresser Good Oral

I make my sissy husband suck my strapon
03:48

I make my sissy husband suck my strapon

sissy slut in the beach with C string and rosebud
14:44

sissy slut in the beach with C string and rosebud

Soloman - Sissy Trainer Vol. 13
04:30

Soloman - Sissy Trainer Vol. 13

black cocks for sissy whores
04:08

black cocks for sissy whores

Fucking my sissy bitch raw pt3of3
03:47

Fucking my sissy bitch raw pt3of3

Love the Head on this Cock
00:59

Love the Head on this Cock

Slut fucks loser sissy
10:06

Slut fucks loser sissy

Multiple cum in stockings fucking dildo no hands
04:23

Multiple cum in stockings fucking dildo no hands

Embrace Your Destiny Sissy Popper Trainer
12:46

Embrace Your Destiny Sissy Popper Trainer

real sissy in chastity outdoor
11:23

real sissy in chastity outdoor

Sissy katelyn cums on her own face
03:55

Sissy katelyn cums on her own face

Crossdressing Sissy pegged by girlfriend
04:34

Crossdressing Sissy pegged by girlfriend

Crossdresser sluts in nylon panties go crazy for big cock blowjob sixtynine and cumshot
11:26

Crossdresser sluts in nylon panties go crazy for big cock blowjob sixtynine and cumshot

Pegging CD by sexy hot female strap-on wearing lingerie and panties
10:26

Pegging CD by sexy hot female strap-on wearing lingerie and panties

Sissy Faggot Smokes For His Master
05:25

Sissy Faggot Smokes For His Master

Sissy Diane Big And Beautiful
02:29

Sissy Diane Big And Beautiful

Sissy crossdresser Annette takes on two cocks 2of3
09:53

Sissy crossdresser Annette takes on two cocks 2of3

Crossdresser fucks girlfriend in lingerie many ways
15:27

Crossdresser fucks girlfriend in lingerie many ways

2 Lesbians sissy boy playing sex for fun
49:35

2 Lesbians sissy boy playing sex for fun

better then my husband!! hot wife makes love to a transexual deep creampie
10:06

better then my husband!! hot wife makes love to a transexual deep creampie

Trans, sissy, playthings
17:13

Trans, sissy, playthings

Sissy crossdresser maid in uniform and latex uses fucking machine
08:57

Sissy crossdresser maid in uniform and latex uses fucking machine

Sissyfied sub spunks on FEMDOM dom boots too early
08:00

Sissyfied sub spunks on FEMDOM dom boots too early

mistress wanking sissy in frilly panties
07:28

mistress wanking sissy in frilly panties

My Sissy Trainer - Hypnotic Sissy Trainer
04:57

My Sissy Trainer - Hypnotic Sissy Trainer

Teen Crossdresser and Tranny GFs!
03:06

Teen Crossdresser and Tranny GFs!

Interracial bbc sissy anal hypno
03:35

Interracial bbc sissy anal hypno

Mature sissy couple loves blowjob, fist and double fist
10:08

Mature sissy couple loves blowjob, fist and double fist

Shemale Schoolgirl Fucked
24:19

Shemale Schoolgirl Fucked

Sissy Hypno Brainwashing
02:19

Sissy Hypno Brainwashing

Hoe gets licked and fucked by sissy
07:00

Hoe gets licked and fucked by sissy

Sissy Swap Tales Super Sissy 1
13:02

Sissy Swap Tales Super Sissy 1

Happy Valentines from c2cmaster and my sissies
13:58

Happy Valentines from c2cmaster and my sissies

Sissy Training Crossdresser Humiliation
03:15

Sissy Training Crossdresser Humiliation

Sissy Spanked Over The Hood Of Car
05:26

Sissy Spanked Over The Hood Of Car

Crossdresser sissy gets cbt tt
05:05

Crossdresser sissy gets cbt tt

BBW Sissy - Sucking my dildo
02:29

BBW Sissy - Sucking my dildo

sissy eve cocksucking slut
01:00

sissy eve cocksucking slut

Crossdresser Captured And Dominated By Three Mistresses
14:11

Crossdresser Captured And Dominated By Three Mistresses

Crossdresser amateur cums
05:37

Crossdresser amateur cums

Sissy Laura - Cumming With A BBC In My Ass (Cumshot - Shorter Version)
00:19

Sissy Laura - Cumming With A BBC In My Ass (Cumshot - Shorter Version)

Hot Pegging Strapon Fem Sissy Fucked Doggystyle
05:00

Hot Pegging Strapon Fem Sissy Fucked Doggystyle

Tranny Slut Mandy Sucking Her Master
02:44

Tranny Slut Mandy Sucking Her Master

Classsy hoe sucks and tugs sissy
07:00

Classsy hoe sucks and tugs sissy

Crossdressing sissy facing a dominatrix
06:01

Crossdressing sissy facing a dominatrix

Glam clothed hoe rides sissys cock
10:08

Glam clothed hoe rides sissys cock

Sissy slut spit roasted and cums in sexy white panties
14:53

Sissy slut spit roasted and cums in sexy white panties

Thick ass white girl finger her tight asshole
01:38

Thick ass white girl finger her tight asshole

Mature Mariko blowjob and facial cumshots by lucky oldman.
05:19

Mature Mariko blowjob and facial cumshots by lucky oldman.

Rubbing my sissy clit and messin my pink panties with spunk before sleep
02:22

Rubbing my sissy clit and messin my pink panties with spunk before sleep

Big Beautiful Sissy Diane Smoke Slut
02:10

Big Beautiful Sissy Diane Smoke Slut

Latin Shemale Fucks Sissy Boy Asshole
10:30

Latin Shemale Fucks Sissy Boy Asshole

Asian mistress strap sissy
04:03

Asian mistress strap sissy

real sissy slut anal in chastity cage
14:50

real sissy slut anal in chastity cage

Daddy plays with his Sissy Gril
05:41

Daddy plays with his Sissy Gril

Young sissy crossdresser desperatetranny
03:44

Young sissy crossdresser desperatetranny

upskirts on the stairs 06
05:46

upskirts on the stairs 06

Crossdresser turns uncle into a sissy whore
01:09

Crossdresser turns uncle into a sissy whore

Hooker Mariko anal fuck with fanboy.
09:55

Hooker Mariko anal fuck with fanboy.

Sissy masturbating and fingering
07:08

Sissy masturbating and fingering

Cute Sissy Ass Crossdresser Hard Fuck JADE (Full Video)
05:39

Cute Sissy Ass Crossdresser Hard Fuck JADE (Full Video)

Distraction while riding a dildo,
00:30

Distraction while riding a dildo,

Dominatrix ruling over useless sissys
05:05

Dominatrix ruling over useless sissys

Hairy Sissy Playing with Cock and Cum by TROC
02:16

Hairy Sissy Playing with Cock and Cum by TROC

Sissy Encouragement. Pm Vol. 84
11:42

Sissy Encouragement. Pm Vol. 84

Give up on being a man! YOU ARE A SISSY FAGGOT!
03:50

Give up on being a man! YOU ARE A SISSY FAGGOT!

Horny teen sissy CD dressed as a gurl
06:07

Horny teen sissy CD dressed as a gurl

Sissy Vickie Sucks Her Dildo & Fucks Her Ass
13:29

Sissy Vickie Sucks Her Dildo & Fucks Her Ass

Sexy BBC fucks my sissy pussy deep 2
00:38

Sexy BBC fucks my sissy pussy deep 2

Cyndee and Wendy Jane Sissy Outdoor Fun
04:20

Cyndee and Wendy Jane Sissy Outdoor Fun

GF fucks her partner that is sissy on camera
15:31

GF fucks her partner that is sissy on camera

SissyFountain Schoolgirl Sissy must vibe to completion
02:34

SissyFountain Schoolgirl Sissy must vibe to completion

sissy cuckold transformation
10:17

sissy cuckold transformation