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Sissy: 4175 Movies, sorted by Duration

German mistress Silvia trains her sissy maid

German mistress Silvia trains her sissy maid

01:41:04
Hottest ts princess on earth

Hottest ts princess on earth

01:34:11
Sissy Husband

Sissy Husband

55:23
Academy for sissies

Academy for sissies

54:39
2 Lesbians sissy boy playing sex for fun

2 Lesbians sissy boy playing sex for fun

49:35
Sissy fucking compilation 2

Sissy fucking compilation 2

35:32
Sissys Cock And Cum Addiction

Sissys Cock And Cum Addiction

34:13
Black Cock For CDS

Black Cock For CDS

30:06
Black Cock worship for sissies!

Black Cock worship for sissies!

30:03
Two Men as Two Girls

Two Men as Two Girls

29:53
Daddy's Sissies

Daddy's Sissies

26:26
Sissy Dream 3

Sissy Dream 3

26:14
Sissy slut Patricia gets a DP and facial

Sissy slut Patricia gets a DP and facial

25:40
Sissy Slut Katie

Sissy Slut Katie

25:28
Best JOI Edit

Best JOI Edit

24:54
Shemale Schoolgirl Fucked

Shemale Schoolgirl Fucked

24:19
Crossdresser Sex Fun

Crossdresser Sex Fun

22:58
2 Mistress Fuck a Sissy

2 Mistress Fuck a Sissy

22:23
cuntfacenow 4 sissy sluts

cuntfacenow 4 sissy sluts

21:55
Cute Asian Crossdresser Triss Goth 2

Cute Asian Crossdresser Triss Goth 2

20:37
A Sissy's Dream-2

A Sissy's Dream-2

20:09
Become a blonde slut girl

Become a blonde slut girl

19:56
Eva no hands cum

Eva no hands cum

19:21
Trio Jazzing With Sissy Boys

Trio Jazzing With Sissy Boys

19:21
Hot Drag Sissies

Hot Drag Sissies

18:36
Sissy Dildo Slave 13

Sissy Dildo Slave 13

18:22
Sissy slut banging compilation

Sissy slut banging compilation

18:16
Sissy whore sent to please neighbor by her Mistress

Sissy whore sent to please neighbor by her Mistress

18:03
Two Latex Sissies Banging

Two Latex Sissies Banging

17:16
Super cute and pretty teenager ladyboy very sissy with a mushroom head cock wank and cum

Super cute and pretty teenager ladyboy very sissy with a mushroom head cock wank and cum

17:13
Trans, sissy, playthings

Trans, sissy, playthings

17:13
Older gal introduces Sissy to her first hard cock to suck on

Older gal introduces Sissy to her first hard cock to suck on

17:07
Mature cd loves dildo fuck.

Mature cd loves dildo fuck.

17:04
Sissy Boy Bound 3.0

Sissy Boy Bound 3.0

15:52
Giant fucking strapon

Giant fucking strapon

15:33
GF fucks her partner that is sissy on camera

GF fucks her partner that is sissy on camera

15:31
Crossdresser fucks girlfriend in lingerie many ways

Crossdresser fucks girlfriend in lingerie many ways

15:27
cheatig wife give blowjob and get fucked doggy by sexy tan transexual

cheatig wife give blowjob and get fucked doggy by sexy tan transexual

15:25
Men Acting Like Women Pegged By Dominatrixes

Men Acting Like Women Pegged By Dominatrixes

15:14
Sissy Vickie Fucks Her Throat and Sprays Her Face

Sissy Vickie Fucks Her Throat and Sprays Her Face

15:03
Sissy slut spit roasted and cums in sexy white panties

Sissy slut spit roasted and cums in sexy white panties

14:53
real sissy slut anal in chastity cage

real sissy slut anal in chastity cage

14:50
Man become a princess

Man become a princess

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

sissy slut in the beach with C string and rosebud

14:44
Sissy serves man

Sissy serves man

14:23
Crossdresser Captured And Dominated By Three Mistresses

Crossdresser Captured And Dominated By Three Mistresses

14:11
Happy Valentines from c2cmaster and my sissies

Happy Valentines from c2cmaster and my sissies

13:58
real sissy full in chastity

real sissy full in chastity

13:34
Sissy Vickie Sucks Her Dildo & Fucks Her Ass

Sissy Vickie Sucks Her Dildo & Fucks Her Ass

13:29
Sissy Swap Tales Super Sissy 1

Sissy Swap Tales Super Sissy 1

13:02
Embrace Your Destiny Sissy Popper Trainer

Embrace Your Destiny Sissy Popper Trainer

12:46
Oral Training

Oral Training

11:53
Brihanna & Carolain two hot TGirls

Brihanna & Carolain two hot TGirls

11:44
Sissy Encouragement. Pm Vol. 84

Sissy Encouragement. Pm Vol. 84

11:42
Hot crossdresser doesnt get to say no to take black cock

Hot crossdresser doesnt get to say no to take black cock

11:33
Super Hot Big Titty Crossdresser Sissy Goddess Part 1

Super Hot Big Titty Crossdresser Sissy Goddess Part 1

11:27
Crossdresser sluts in nylon panties go crazy for big cock blowjob sixtynine and cumshot

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

11:26
real sissy in chastity outdoor

real sissy in chastity outdoor

11:23
A Sissy life

A Sissy life

11:17
Sissy Love 4

Sissy Love 4

11:17
Sissy tart

Sissy tart

11:12
Rachel Samantha Love BBC

Rachel Samantha Love BBC

11:10
Tranny Goth Sucks on a Big Hard Cock

Tranny Goth Sucks on a Big Hard Cock

11:07
What It Takes To Be A Sissy

What It Takes To Be A Sissy

10:49
oh yes my sissy bitch!! fuck my pussy and fill me up, huge creampie

oh yes my sissy bitch!! fuck my pussy and fill me up, huge creampie

10:40
Crossdresser gets Strap on by FemDom

Crossdresser gets Strap on by FemDom

10:40
Horny boy breeding sissy's hole

Horny boy breeding sissy's hole

10:34
Latin Shemale Fucks Sissy Boy Asshole

Latin Shemale Fucks Sissy Boy Asshole

10:30
Pegging CD by sexy hot female strap-on wearing lingerie and panties

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

10:26
Flirt, Wiggle and Find a Cock...You Sissy Cumslut

Flirt, Wiggle and Find a Cock...You Sissy Cumslut

10:26
Femdom Pegging - Sissy boy gets fucked by girlfriend

Femdom Pegging - Sissy boy gets fucked by girlfriend

10:22
Dreamscape Sissy training

Dreamscape Sissy training

10:20
Cross fucked

Cross fucked

10:19
Hot Sissy Girl Livia Gets Fucked

Hot Sissy Girl Livia Gets Fucked

10:18
Crossdress!

Crossdress!

10:17
sissy cuckold transformation

sissy cuckold transformation

10:17
Mature sissy couple loves blowjob, fist and double fist

Mature sissy couple loves blowjob, fist and double fist

10:08
Glam hoe pissed on by sissy

Glam hoe pissed on by sissy

10:08
Glam clothed hoe rides sissys cock

Glam clothed hoe rides sissys cock

10:08
Glam babe sucks off a blonde sissy

Glam babe sucks off a blonde sissy

10:07
better then my husband!! hot wife makes love to a transexual deep creampie

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

10:06
Slut fucks loser sissy

Slut fucks loser sissy

10:06
Rub it Like a Girl JOI

Rub it Like a Girl JOI

09:57
Femdom mistress and sissy

Femdom mistress and sissy

09:33
Kalina Proud To Be A Kinky Smoking Slut

Kalina Proud To Be A Kinky Smoking Slut

09:06
Sissy crossdresser maid in uniform and latex uses fucking machine

Sissy crossdresser maid in uniform and latex uses fucking machine

08:57
Sissy fem fucked

Sissy fem fucked

08:55
Femdom spanks and tortures naughty blonde sissy with huge strapon cock

Femdom spanks and tortures naughty blonde sissy with huge strapon cock

08:42
Strapon the sissy

Strapon the sissy

08:34
Sissy gets Strapon punishment

Sissy gets Strapon punishment

08:23
Sissy Boy Punished Hard

Sissy Boy Punished Hard

08:19
Sissy Cock Sucker.

Sissy Cock Sucker.

08:13
Tatiany Loves BBC

Tatiany Loves BBC

08:03
Sissyfied sub spunks on FEMDOM dom boots too early

Sissyfied sub spunks on FEMDOM dom boots too early

08:00
sissy takes it raw!

sissy takes it raw!

07:44
Sissy Maid Blackmailed

Sissy Maid Blackmailed

07:35
mistress wanking sissy in frilly panties

mistress wanking sissy in frilly panties

07:28
Caged Sissy

Caged Sissy

07:23
Sissy Fag Trainer

Sissy Fag Trainer

07:22
Sissy faggot

Sissy faggot

07:09
Sissy masturbating and fingering

Sissy masturbating and fingering

07:08
Hoe gets licked and fucked by sissy

Hoe gets licked and fucked by sissy

07:00
Classsy hoe sucks and tugs sissy

Classsy hoe sucks and tugs sissy

07:00
Slut gets pissed on by sissy

Slut gets pissed on by sissy

07:00
Ass fucking with huge black dildo!

Ass fucking with huge black dildo!

06:57
CD fucks hot MILF doggy till she Squirts

CD fucks hot MILF doggy till she Squirts

06:46
annalicious88 smoking and exposing like sissy whore

annalicious88 smoking and exposing like sissy whore

06:44
Sissy Jennifer used by mistress rita's friend

Sissy Jennifer used by mistress rita's friend

06:36
Hyp Sissy Slut Voices

Hyp Sissy Slut Voices

06:27
mature whore crossdresser mariko hot blowjob

mature whore crossdresser mariko hot blowjob

06:13
Sissy factory

Sissy factory

06:12
Femdom wife fucks sissy crossdresser

Femdom wife fucks sissy crossdresser

06:10
Jeniffer´s wedding dress masturbation

Jeniffer´s wedding dress masturbation

06:04
Prisoner sucking a crossdresser sissy

Prisoner sucking a crossdresser sissy

06:01
Crossdressing sissy facing a dominatrix

Crossdressing sissy facing a dominatrix

06:01
Huge Penis Plug and XXXL Butt Plug in Crotchless Panties and Stockings

Huge Penis Plug and XXXL Butt Plug in Crotchless Panties and Stockings

05:58
Submissive sissy slut training

Submissive sissy slut training

05:55
Sissy Training Volume 4 - Daddy's Home

Sissy Training Volume 4 - Daddy's Home

05:47
upskirts on the stairs 06

upskirts on the stairs 06

05:46
Daddy plays with his Sissy Gril

Daddy plays with his Sissy Gril

05:41