SHEMALE • SISSY 67,717 videos

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12:53

Shemale sissy Rileydix Dirty Talks you into Fucking her Faggot Pussy

2 years ago

xHamster

dirty talk, sissy
10:33 87%

Twunk slamming his cheeks with bimbo cone. NOW WITH MORE KNOTTING also, sneak peak at Upcoming video

2 years ago

ShemaleMovie

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07:14 76%

Wonderful CD get shag on bed with her transparent nightie

2 years ago

ShemaleTaxi

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08:31 50%

Transgirl sucks, gets lashed and pummeled

1 year ago

ShemaleMovie

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17:43

Close up Sissy Elvi Lynx Anal Fucking with Big Dildo

1 month ago

$$ FapHouse

anal, dildo, ladyboy, close up, sissy
07:52

SUPER uber-sexy ash-blonde Sissy plowed Hard

2 months ago

ShemaleTaxi

amateur, crossdresser, femboy, sissy, big cock
05:05

Sexy satin secretary seals the deal!

1 year ago

AShemaleTube

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02:48 67%

Cute British SIssy JOI and Rubs Cock

3 years ago

xHamster

cute, british, JOI, cosplay, sissy
04:42 50%

Sexy like a Sissy 7

6 years ago

xHamster

stockings, lingerie, BDSM, toys, sissy
13:42

Trans Love Anal Most Indoor

2 months ago

BeMyHole

amateur, shemale, domination, sissy, missionary, hardcore, femboy
06:30

Dangling Out with my fresh Acquaintance

2 months ago

TrannyGem

feet, homemade, blowjob, big ass, babe, ass, reality
12:51 46%

My husband is a sissy.

6 years ago

ShemaleZ

husband, sissy
05:21

My Sissy Must Cum Free Hands, Compilation

1 month ago

HClips

stockings, MILF, crossdresser, compilation, masturbation, toys, sissy
05:25 79%

Who would think Im a man? JK Uniform, Gorgeous She-Male Cosplayer get Romped, Costume Play Kawaii Chinese Cr

2 years ago

TrannyGem

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25:48 85%

Femboyhami Comp4

1 year ago

AShemaleTube

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07:12 83%

Alice Blitz And Clara Blitz In Two Blonde Sissy Lesbians Getting Anal Sex

4 years ago

ShemaleZ

lesbian, teen anal (18+), sissy
08:06

Valentine S Day - Getting A Sissy For

6 months ago

ShemaleZ

bareback, sissy, stockings, shemale
17:13 53%

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7 years ago

AShemaleTube

interracial, crossdresser, sissy
03:12 71%

Trying to keep quiet while masturbating in the bathroom

10 months ago

AShemaleTube

shemale, solo, sissy
14:40 67%

Crossdresser Danni plays with her rigid pecker in stockings and hight heels.

3 months ago

ShemaleMovie

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01:34 88%

Cuckold Sissy Rob his wife and their BBC lover

1 year ago

AShemaleTube

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05:31

Sissy gets stiff pulverized with fucktoy

1 year ago

ShemaleTaxi

sissy
06:24

Sissy fucked from behind, her first big arab cock

4 years ago

xHamster

latex, arab, outdoor, sissy
15:05

Sissy Neri And Renata Davila - Hardcore Foursome With Tgirl Milf

10 months ago

ShemaleZ

group, sissy, stockings, foursome, big tits, hardcore
07:48

Drew Honeysuckle Sissy Sluts Foursome With Fans

2 years ago

GetTranny

sissy, foursome, interracial, 18
05:09 60%

In tan Jumpsuiet on tour

1 week ago

AShemaleTube

crossdresser, sissy, amateur, stockings, shemale
10:51

Manhood thirsty shemale in red lingerie

2 weeks ago

ShemaleMovie

sissy, solo, shemale fucks guy, thai
10:08

Large big black cock Takes Ria Bentley to Poundtown with creampie

1 year ago

ShemaleTaxi

lingerie, sissy, creampie, amateur, BBC, black
30:12 88%

Hands Free Sissygasms

1 month ago

AShemaleTube

anal, ladyboy, cumshot, big cock, toys, sissy, hands free
09:29

Sissy in the sun 1

4 years ago

ShemaleTaxi

german, taxi, sissy
10:33 70%

Guy watched his girlfriend take it in the butt

3 years ago

xHamster

anal, interracial, wife, cuckold, girlfriend, sissy
05:06

Small Trans gal torn up on Kitchen Counter.

4 months ago

ShemaleMovie

femboy, sissy, amateur, shemale, small cock, kitchen
04:36

Tell Your Wifey You Like Trunk Up the Booty & Shell Ravage You Even Tighter Tramps

2 months ago

TrannyGem

mature, amateur, mom, creampie, mature anal, wife, MILF
06:54

About me - an introduction

Yesterday

AShemaleTube

crossdresser, solo, sissy, amateur
19:44

My Sissy boyfriend 23

1 year ago

ShemaleTaxi

domination, sissy, shemale, anal, BDSM, boyfriend
12:06 81%

Sissy Teenager Asian Ladyboy Slut Suck Cock And Get Fucked

4 years ago

ShemaleZ

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16:50 64%

Sissy Tgirl CD inhales and get ruined by monster hard-on BBC

8 months ago

ShemaleMovie

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10:56

Sissy Pov - Khloe Cox - Blonde Cutie Loves Your D

3 years ago

ShemaleZ

sissy
07:04 78%

Don't Think, Slut

4 years ago

xHamster

lingerie, 18, slut, sissy
11:18

Sisi femboy in a swimsuit with her big doll penis ready for action

1 month ago

XXXVogue

swimsuit, sissy, femboy, doll
14:54

Sissy Anal Compilation

1 month ago

AShemaleTube

compilation, sissy, crossdresser, shemale, solo
16:11

Crossdresser Sissy (two)

6 years ago

ShemaleZ

crossdresser, sissy
05:18 40%

Sissy Boi Cumshot Self Facial

1 year ago

ShemaleZ

shemale, sissy, facial, cumshot
05:11

Sissy cums twice from big dildo

1 year ago

AShemaleTube

dildo, sissy
10:31

Emo Sissy drilled by domina Pixie

1 year ago

ShemaleMovie

femdom, shemale, sissy
11:17

Cd holly sissygasms

5 months ago

TrannyGem

anal, crossdresser, stockings, sissy, amateur
10:23

Grindr dad Barebacks a Tall Sissy

6 months ago

ShemaleMovie

anal, tall, BDSM, crossdresser, ass to mouth, domination, sissy
10:09 79%

Sissy Girl Feminization

5 years ago

TrannyGem

doll, sissy
26:48 81%

MAID SISSY CROSSDRESSER CAUGHT FROLICKING WITH CHICKS PLAYTHINGS, LORD GETS ANGRY, DOMINATION & SUBMISSION, ANAL INVASION, CD,

4 years ago

KeekAss

mature, homemade, stockings, mature anal, maid, crossdresser, caught
06:25

Goth Crossdresser Teasing and Sucking Dildo

2 years ago

xHamster

crossdresser, goth, sissy
05:48

School Sissy Anal Lesson Xh7dvi5

3 years ago

HClips

sissy
09:30 67%

Uber-Cute Japanese Sissy Assfucking & Jizz in Chat

5 years ago

KeekAss

japanese, sissy
06:36

Sissy-maker Academy Volume 2

1 year ago

JizzBunker

amateur, compilation, cumshot compilation, sissy
12:04 55%

Sissy taught to suck three cocks by mother (POV camerwork)

6 years ago

ShemaleZ

handjob, sissy, train
18:47

Black Daddy Breeds White Sissy

3 years ago

Upornia

interracial, sissy, amateur
1:10:29 81%

A Lot Of Sex & Cum

3 years ago

BeMyHole

beauty, anal, facial, compilation, blonde, cumshot compilation, sissy
01:55 50%

18 Teen Femboy loves LONG black dildo.

6 months ago

AShemaleTube

amateur, black, teen (18+), teen anal (18+), dildo, 18, sissy
03:29

Sexy sissy Ponyboy is dancing in white lingerie

3 years ago

xHamster

dance, sissy
02:20 88%

Lonely CD Sprays 1:59

5 months ago

AShemaleTube

asian, shemale, femboy, sissy, pantyhose, solo
05:03 67%

[SISSY] When I was doing park ass fucking getting off in the daytime, 2 senior guys helped me.

7 months ago

TrannyGem

public, outdoor, crossdresser, piercing, gangbang, sissy, chastity
02:06 89%

Trans in fishnet stocking is boinked sans a condom

2 years ago

TrannyGem

turkish, homemade, crossdresser, heels, sissy, femboy
06:46 67%

My mega-slut wants two meatpipes in her fat ass

10 months ago

ShemaleTaxi

fat, dildo, crossdresser, prostitute, machine, slut, BBC
06:40

Sissy mega-slut Guide To full Whoredom Vol. 2

3 years ago

ShemaleTaxi

prostitute, slut, sissy
08:00 69%

Sissy Molly Anal Sex In The Bathroom

10 months ago

Fuxxx

amateur, shemale, sissy, POV, facial, bathroom
09:38 78%

Sissy Strap-on Pegging Spitroast By Double Dommes Mistress Mercer And Coral

4 years ago

TXXX

femdom, shemale, strapon, threesome, pegging, sissy, double penetration
10:38 68%

Sissy Cougar CD RileyDix plays with her hefty rump taunting and chatting sloppy wants your jizm!

9 months ago

TrannyGem

amateur, POV, MILF, crossdresser, strip, dirty talk, ass
05:52

Tricked and sissyfied

5 years ago

BeMyHole

crossdresser, sissy
05:48 88%

The First Video In My New Leather Nun Outfit. What A Clip. Hard And Bar E Back. Dont Forget To Like If You Liked The Surprise

1 year ago

BeMyHole

amateur, latex, anal, fetish, nun, leather, surprise
23:49 66%

Magnificent femboy with her luxurious face and sensitive figure. her make-up makes her sight like a queen

1 year ago

TrannyGem

mature, amateur, cute, public, blowjob, POV, couple
14:13

Sissy humiliation

6 years ago

ShemaleZ

sissy
12:41

Sissy In Action

7 years ago

ShemaleZ

sissy
14:07

Sissification Lecture The MEANING of SISSY LIFE by Dominatrix Veronica Taboo at Online Sissy Academy

3 years ago

KeekAss

sissy
07:07

Yaoi Femboy - Seth is torn up on the teach

5 months ago

ShemaleMovie

femboy, creampie, sissy, crossdresser
08:36

Me hace una sesión fotográfica pornography, se le paro la verga!

7 months ago

ShemaleMovie

orgasm, ladyboy, socks, futanari, BBC, sissy, gape
04:12

Trans-62

7 months ago

AShemaleTube

big cock, amateur, sissy, small cock
06:40 63%

Kissing hot trans Vandella Evangelista with a big ass

4 months ago

XXXVogue

kissing, amateur, sissy, shemale fucks guy, big cock, domination
01:21

SISSY TRAP - GLITCH PISS COMPILATION

3 years ago

xHamster

pissing, 18, creampie compilation, sissy
05:32 88%

FEELIN P!NK In All The Right Ways

2 years ago

xHamster

beauty, small cock, solo, crossdresser, heels, sissy
02:53

My sissy ass got fucked good.

4 years ago

AShemaleTube

small cock, sissy, crossdresser
05:13

Blue Archive Shupogaki cosplayer get pounded, Asian hentai Cosplay 2

1 year ago

ShemaleTaxi

asian, japanese, ladyboy, crossdresser, sissy, cosplay
03:15

Very Cute Sissy on Cam VR88

10 years ago

xHamster

cute, stockings, sissy
04:02

Sissy Andrea Anal Workout

3 years ago

Upornia

sissy
21:40

TALL SMALL DICK SHEMALE TRAP SISSY SLUT BBCD

6 years ago

ShemaleZ

tall, slut, BBC, sissy, interracial
09:53 85%

Sissy crossdresser Annette takes on 2 sausages 2of3

6 years ago

KeekAss

crossdresser, sissy, threesome, mature
13:12

Asian sissy Alicexiao pulverize machine

7 months ago

ShemaleTaxi

crossdresser, sissy, machine, chinese, selfsuck, asian
04:30

Biking Sissy - saucy posing in public

3 years ago

xHamster

public, mature anal, sissy
49:47 82%

Tgirl beauty sucks, edges & fingers tight hole

1 year ago

AShemaleTube

beauty, big tits, solo, ass to mouth, ass, tight, webcam
1:07:08 53%

Sissys panties donk And Clittys

2 years ago

ShemaleMovie

creampie, panties, sissy
05:26

Chinese Satanic Sissy Plays Alone - Faux-Cock Tribute Ritual Dance

4 years ago

KeekAss

dance, chinese, sissy
02:54 80%

Cum to the trans party

1 year ago

AShemaleTube

pantyhose, shemale, party, crossdresser, sissy
05:57

T-Girl smoking in the park

1 month ago

TrannyGem

crossdresser, amateur, british, shemale and girl, sissy, smoking
05:20

Sissy Ladyboy Gets It in Mouth

7 years ago

AShemaleTube

cum in mouth, sissy
08:43 50%

Sandra takes shaft up her sissy ass

4 years ago

ShemaleTaxi

british, sissy
07:14

Mouth Fucking My Hot Sissy Bitch Pushing Her Head All The Way Down On 8 Inches Dick Slapping Her

3 years ago

ShemaleZ

MILF, 18, sissy
04:45

Blue Sissy Slut Hard Anal Lolafrina

4 years ago

ShemaleZ

crossdresser, slut, sissy
01:31

Cpiexo

4 months ago

AShemaleTube

cumshot, sissy, big cock, solo, masturbation
11:34 75%

Sissy moon

1 year ago

XXXDan

lingerie, riding, sissy, dildo
03:41

Sexy leopard coat on sexy girl with high heels boots

3 years ago

xHamster

boots, heels, sissy
05:29 52%

Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson

5 years ago

xHamster

teen (18+), russian, crossdresser, sissy, first time, femboy
12:45

Sissy bitch Bess brings herself to a gam jiggling ejaculation

6 months ago

TrannyGem

amateur, cute, asian, orgasm, crossdresser, sissy, anal orgasm
24:39 89%

Real Chatty Ultra-Kinky Sissy(Need a sissy like her)

4 years ago

KeekAss

handjob, ebony, blowjob, anal, bareback, sissy
30:03

Afternoon Sissy delectation

2 years ago

ShemaleTaxi

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05:51

Giant cock small tits sissy dom t-girl drills fucktoy

5 months ago

ShemaleMovie

toys, sissy, small cock, BDSM, big cock
16:54 80%

Aliza Breeze - Tennis Club Sissy - Liza Shay

1 year ago

ShemaleZ

ebony, POV, big ass, interracial, prostitute, ass, club
04:05

Hotwife BOYFRIEND Gets Dt from Sissy Transgender Princess Julia

4 months ago

TrannyGem

crossdresser, sissy, boyfriend
08:14 40%

Jessy Takes Mreasydecks bbc Deep and rigid

4 months ago

ShemaleTaxi

BBC, anal, sissy, black
12:45

She-male babes Flowergoth Roze & Bambi Bootylucious in Crazy ass-Fuck!

1 year ago

ShemaleMovie

asshole, big ass, pissing, sissy, orgasm, solo
04:02 67%

HUGE BBC in a Sissy Throat and Pussy

3 years ago

TrannyOne

interracial, BBC, sissy
25:51

Naughty Halloween 2025

2 months ago

AShemaleTube

domination, futanari, cum in mouth, sissy, shemale and girl
03:26

Make my pink hole cream-colored with prompt deep fuckfest machine

8 months ago

TrannyGem

cute, sissy, french, machine, crossdresser
05:40 75%

Handsome Ponny Letany Becoming More and More pansy

7 months ago

ShemaleMovie

small cock, thai, babe, heels, small tits, sissy
21:38

Crossdress Sissy Hard Fuck

4 years ago

ShemaleZ

brunette, sissy, crossdresser
02:13

Spectacular sissy femboy plays raw & muddy with assfucking beads

2 months ago

TrannyGem

asian, crossdresser, 18, sissy, masturbation, cumshot
29:53

Deep assfuck is my passion - Sissy Trap

2 years ago

KeekAss

amateur, cumshot, sissy, crossdresser
14:05

I am prepared to take knob clad as a sissy

3 years ago

ShemaleTaxi

panties, sissy
05:15

My girlfriend dildos me with a Toys

1 year ago

xHamster

french, sissy, amateur, latex, dildo, couple
02:03

TSCD Shoots 1:11

3 months ago

AShemaleTube

small cock, shemale, masturbation, chinese, small tits, sissy, femboy
14:49 67%

Magic captions sissy

7 years ago

ShemaleZ

sissy, lingerie
07:45

Misr4 - fleshlight cumshot

2 years ago

xHamster

handjob, orgasm, cumshot, sissy, fleshlight, polish
12:06

Bnwo Sissy Bride Gooning

4 months ago

$$ FapHouse

fetish, amateur, sissy, shemale, bride, dildo

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