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Sissy: 4187 Videos, grouped by Popularity

Horny teen sissy CD dressed as a gurl
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Horny teen sissy CD dressed as a gurl

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Crossdresser amateur cums

SissyFountain Schoolgirl Sissy must vibe to completion
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SissyFountain Schoolgirl Sissy must vibe to completion

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Sexy BBC fucks my sissy pussy deep 2

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15:33

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30:03

Black Cock worship for sissies!

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Sissy slut Becky whip my ass

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Doggystyle big dildo

Sissy crossdresser in long boots and corset fucked in the ass by stranger
01:12

Sissy crossdresser in long boots and corset fucked in the ass by stranger

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

Sissy Vickie Fucks Her Throat and Sprays Her Face

Sissy Training Ep.1
06:48

Sissy Training Ep.1

Cute Asian Crossdresser Triss Goth 2
20:37

Cute Asian Crossdresser Triss Goth 2

MILF giving a hot Crossdresser Good Oral
04:16

MILF giving a hot Crossdresser Good Oral

Soloman - Sissy Trainer Vol. 13
04:30

Soloman - Sissy Trainer Vol. 13

Feminization, sissy and crossdressing
01:16

Feminization, sissy and crossdressing

Emma Grayy cums in nude stockings
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Emma Grayy cums in nude stockings

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04:38

Sissy trainer and cock worship

Embrace Your Destiny Sissy Popper Trainer
12:46

Embrace Your Destiny Sissy Popper Trainer

MF Sissy Training SEXY CD
03:30

MF Sissy Training SEXY CD

Sissy Slut Katie
25:28

Sissy Slut Katie

SissyFountain Schoolgirl Sissy must vibe to completion
02:34

SissyFountain Schoolgirl Sissy must vibe to completion

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17:04

Mature cd loves dildo fuck.

Cock sucking sissy trainer: Rude Boy edition
03:47

Cock sucking sissy trainer: Rude Boy edition

Huge Penis Plug and XXXL Butt Plug in Crotchless Panties and Stockings
05:58

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

sissy Lucas Montes
01:15

sissy Lucas Montes

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Sissy suck 2

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18:45

Sissy boy sweet fuck

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06:10

Femdom wife fucks sissy crossdresser

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Illuminati sissy toy.FLV

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sissy eve cocksucking slut

Tatiany Loves BBC
08:03

Tatiany Loves BBC

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Humiliating the crossdressing sissy pindick whiteboy, SPH

Kalina Proud To Be A Kinky Smoking Slut
09:06

Kalina Proud To Be A Kinky Smoking Slut

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13:58

Happy Valentines from c2cmaster and my sissies

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

Sissy crossdresser Annette takes on two cocks 2of3

Sissy fucking compilation 2
35:32

Sissy fucking compilation 2

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08:00

Sissyfied sub spunks on FEMDOM dom boots too early

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54:39

Academy for sissies

Glam clothed hoe rides sissys cock
10:08

Glam clothed hoe rides sissys cock

Sissy with 2 men
04:22

Sissy with 2 men

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08:57

Sissy crossdresser maid in uniform and latex uses fucking machine

Rub it Like a Girl JOI
09:57

Rub it Like a Girl JOI

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01:38

Thick ass white girl finger her tight asshole

Hot Drag Sissies
18:36

Hot Drag Sissies

Sissys Cock And Cum Addiction
34:13

Sissys Cock And Cum Addiction

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10:10

the maid in thigh boots is a sissy

Brihanna & Carolain two hot TGirls
11:44

Brihanna & Carolain two hot TGirls

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10:07

Glam babe sucks off a blonde sissy

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My dildo and I :)

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07:09

Sissy faggot

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07:28

mistress wanking sissy in frilly panties

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17:13

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

Slut gets pissed on by sissy
07:00

Slut gets pissed on by sissy

Strapon the sissy
08:34

Strapon the sissy

My Sissy Trainer - Hypnotic Sissy Trainer
04:57

My Sissy Trainer - Hypnotic Sissy Trainer

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

Sissy Vickie Sucks Her Dildo & Fucks Her Ass

Sissy Crossdresser Mandy Wanking For You!
03:48

Sissy Crossdresser Mandy Wanking For You!

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14:49

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19:21

Eva no hands cum

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14:23

Sissy serves man

Sissy Dream 3
26:14

Sissy Dream 3

Tranny Goth Sucks on a Big Hard Cock
11:07

Tranny Goth Sucks on a Big Hard Cock

Sissy Training Crossdresser Humiliation
03:15

Sissy Training Crossdresser Humiliation

Cyndee and Wendy Jane Sissy Outdoor Fun
04:20

Cyndee and Wendy Jane Sissy Outdoor Fun

Sissy Swap Tales Super Sissy 2
12:51

Sissy Swap Tales Super Sissy 2

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06:12

Sissy factory

Dreamscape Sissy training
10:20

Dreamscape Sissy training

What It Takes To Be A Sissy
10:49

What It Takes To Be A Sissy

Femdom Pegging - Sissy boy gets fucked by girlfriend
10:22

Femdom Pegging - Sissy boy gets fucked by girlfriend

BBW Sissy - Sucking my dildo
02:29

BBW Sissy - Sucking my dildo

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04:57

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26:26

Daddy's Sissies

Sissy Training Volume 4 - Daddy's Home
05:47

Sissy Training Volume 4 - Daddy's Home

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11:10

Rachel Samantha Love BBC

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08:42

Femdom spanks and tortures naughty blonde sissy with huge strapon cock

The Absolute Best of Amateur Sissy Machine Fucking
01:20:25

The Absolute Best of Amateur Sissy Machine Fucking

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02:56

My favourite sissy

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07:44

sissy takes it raw!

Hot Pegging Strapon Fem Sissy Fucked Doggystyle
05:00

Hot Pegging Strapon Fem Sissy Fucked Doggystyle

Crossdresser fucks girlfriend in lingerie many ways
15:27

Crossdresser fucks girlfriend in lingerie many ways

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06:57

Ass fucking with huge black dildo!

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02:36

Kiss your man sissy!!!

Tranny Slut Mandy Sucking Her Master
02:44

Tranny Slut Mandy Sucking Her Master

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18:16

Sissy slut banging compilation

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04:03

Sissys

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11:33

Hot crossdresser doesnt get to say no to take black cock

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05:09

I am Sissy Bitch

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08:37

We wont judge you for being such a sissy boy

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03:54

me pleasing Master

Smoking Sissy Chrissy
03:16

Smoking Sissy Chrissy

Best JOI Edit
24:54

Best JOI Edit

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06:44

annalicious88 smoking and exposing like sissy whore

2 Mistress Fuck a Sissy
22:23

2 Mistress Fuck a Sissy

Sissy Encouragement. Pm Vol. 84
11:42

Sissy Encouragement. Pm Vol. 84

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00:41

asian sissy cumming

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

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Mature Mariko blowjob and facial cumshots by lucky oldman.

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Daddy plays with his Sissy Gril
05:41

Daddy plays with his Sissy Gril

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02:10

Big Beautiful Sissy Diane Smoke Slut

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heathers story1

Nympho Crossdresser GFs!
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Nympho Crossdresser GFs!

Crossdresser Cuts
03:21

Crossdresser Cuts

Hot Passable Crossdresser Fucks Sexy Babe Hard
11:33

Hot Passable Crossdresser Fucks Sexy Babe Hard

BBW Sissy Diane Want's To Smoke Cock
02:10

BBW Sissy Diane Want's To Smoke Cock

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Teen Crossdresser and Tranny GFs!

Sissy
13:22

Sissy

Super Hot Big Titty Crossdresser Sissy Goddess Part 1
11:27

Super Hot Big Titty Crossdresser Sissy Goddess Part 1

Crossdresser Captured And Dominated By Three Mistresses
14:11

Crossdresser Captured And Dominated By Three Mistresses

Man become a princess
14:44

Man become a princess

Isabella Transex
12:15

Isabella Transex

Sissys & Shemales sucking cock and licking ass
03:12

Sissys & Shemales sucking cock and licking ass

Crossdresser gets Strap on by FemDom
10:40

Crossdresser gets Strap on by FemDom

A Sissy's Dream-2
20:09

A Sissy's Dream-2

7.6 inch cock skinny sissy having an anal orgasm...
05:31

7.6 inch cock skinny sissy having an anal orgasm...

Sissy Compilation
03:08

Sissy Compilation

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

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