SHEMALE • SISSY 58,224 videos

Popular Latest Top rated

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25:10

Boys are brothers and dress up like sissy girls and CUM

3 years ago

AShemaleTube

shemale and girl, dress, sissy, amateur
10:35 73%

Sexy blonde bimbo

2 years ago

xHamster

beauty, crossdresser, sissy, solo
04:53

A Sissy First Night Out - Sundance 2023 Winner

1 year ago

AShemaleTube

amateur, crossdresser, sissy, femboy
14:16

Rica Masturbacion

6 months ago

AShemaleTube

homemade, shemale, lingerie, latina, cumshot, masturbation, bareback
08:18

Cute innocent CD sissy solo play with cumshot

9 months ago

xHamster

beauty, solo, masturbation, sissy
04:45

Sissy hypno 177

4 months ago

AShemaleTube

shemale, sissy
03:08

Fat bum Muslim sissy ASSiya_Pathuzz cat walk and bootie clap

1 year ago

KeekAss

fat, sissy
11:54

Sissy Pov – Jenny Kennedy – Obsessed With Being A Girl

2 years ago

ShemaleZ

POV, sissy
37:17

Sissy boy

4 years ago

xHamster

sissy, interracial
11:12

You're Nothing but a CUNT, sissy Podcast

3 years ago

xHamster

mature, mature anal, sissy
05:22 55%

You are now goddess Annas sundress up lady

2 years ago

ShemaleTaxi

shemale, taxi, sissy, crossdresser
07:53

White Sissy love black cock collection

7 years ago

AShemaleTube

sissy
14:41

Sissy chap And chapfriend

5 years ago

TXXX

interracial, sissy
23:49 56%

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

8 months ago

TrannyGem

mature, amateur, cute, public, blowjob, POV, big ass
06:18

This Cunt Must Cum

5 months ago

xHamster

stockings, sissy
07:52

F-Machine fucked While blowing pink cigar Jessica Bloom Gets Spitroasted With Julia Edge

3 months ago

ShemaleTaxi

homemade, beauty, blowjob, bisexual, ladyboy, crossdresser, british
07:12

Two blonde sissy lesbians have anal sex

11 months ago

XXXDan

teen (18+), lesbian, german, teen anal (18+), sissy
08:40

Sissy in underwear taunts needs pipe for deepthroating and tearing up

3 years ago

TrannyGem

tease, sissy
30:53

Sissy hypno 49

8 months ago

AShemaleTube

sissy, shemale
14:51

Really Hot Blonde Crossdresser Masturbating with Redhead Trans Woman

11 months ago

xHamster

shemale, crossdresser, masturbation, sissy, femboy
12:51 46%

My husband is a sissy.

5 years ago

ShemaleZ

husband, sissy
12:20 75%

Making depth records - pulverizing machine with 17 inch fake penis

1 year ago

ShemaleTaxi

orgasm, dildo, machine, skinny, sissy, gape
06:05 75%

Sissy Meets Horny Guy In Hotel To Take Bareback Cock

1 year ago

TrannyGem

crossdresser, sissy, hotel
06:10

Sissy femboy shakes her ass like the whore she is (I overthought this)

3 months ago

xHamster

amateur, webcam, sissy, femboy
07:20

Handsome teenage she-male in latex dress gets a big facial from

3 days ago

ShemaleTaxi

big cock, fisting, femboy, latex, sissy, hardcore, shemale fucks guy
10:50

Sadie Cums

3 weeks ago

AShemaleTube

stockings, cumshot, sissy, shemale, femboy
03:51

Sissy By Two Hot Cocks

2 years ago

Upornia

interracial, vintage, sissy
24:06

Isabella fucked by 2 guys in pink

2 months ago

AShemaleTube

blowjob, sissy, shemale, amateur, latex, femboy
11:39 77%

Deep sucking sweet bitch (AVN)

3 years ago

xHamster

cute, beauty, small cock, toys, sissy
05:28 50%

Making Out with VERY SEXY Trans Latina

6 months ago

xHamster

crossdresser, sissy, anal
04:02

Sissy molly training her throat for deep throat

5 years ago

HClips

train, deepthroat, sissy
10:01

Aylla Gattina Fucks Sissies-The Biggest Compilation

7 months ago

TrannyOne

compilation, sissy, shemale
14:27 74%

I love gargling manhood

1 year ago

TrannyGem

amateur, crossdresser, sissy
08:55

Sissy Hypno 4

3 years ago

AShemaleTube

sissy
02:43

Sissygasm Hypno - MindFuck PMV by HoloPMV

1 year ago

AShemaleTube

crossdresser, compilation, cumshot compilation, sissy, femboy
19:11

Sissy bitch getting tripple fucked + penetrate machine + lollipop & two fake penises

2 days ago

KeekAss

sissy
19:35 72%

Josie Blade My Fuck Me Dress

1 year ago

BeMyHole

dress, BBC, sissy, sensual, domination, creampie
03:01

Fountains Of Cum On Elf Sissy Femboy

2 years ago

ShemaleZ

sissy
28:33 77%

Sissy Slut Nyxi

2 years ago

Upornia

shemale, webcam, slut, sissy
06:03 75%

Cute Sissy Femboy Play With Dildo

1 year ago

ShemaleZ

dildo, ladyboy, toys, sissy, femboy
38:22

SISSY NIGHT AT A MOTEL

8 months ago

TrannyOne

shemale, sissy, amateur, hotel, anal
09:38 78%

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

3 years ago

TXXX

femdom, shemale, strapon, threesome, pegging, sissy, double penetration
16:08

Squealing loudly on My Stepbrother sausage

2 months ago

ShemaleMovie

handjob, amateur, beauty, black, shemale, BBC, sissy
03:07

Sissy Sylvia Luvs Caboose to Throat

3 years ago

KeekAss

homemade, crossdresser, sissy
16:32 88%

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

3 years ago

TrannyGem

femdom, shemale, blowjob, train, BDSM, shemale and girl, big cock
08:26 94%

Sissy Crossdresser Takes Big Cock

2 years ago

ShemaleZ

amateur, stockings, crossdresser, sissy, blonde
08:43 56%

Service From A Sissy

4 years ago

Upornia

amateur, sissy
05:43

Masked stud - An Unsolved Mystery (Exclusive two Part via Justfor.f-a-n-s @SissyStash)

2 years ago

ShemaleTaxi

crossdresser, mask, bareback, sissy
14:12

Transgender Bunny super-bitch Lilith Eclipse crams her fuck hole with carrots

2 years ago

ShemaleMovie

piercing, sissy, cosplay
19:30 91%

Jessica ketlen fucks her boi toy in a hottle room

1 week ago

AShemaleTube

shemale fucks guy, sissy, big cock, homemade, shemale, blowjob, domination
06:47

Deep fuck by a long black cock

6 months ago

AShemaleTube

sissy, black, amateur
03:34 38%

Fem Sissy Getting Dolled Up And Waiting For Daddy To Deliver His Big Sausage

1 year ago

ShemaleZ

stockings, teen (18+), doll, sissy
05:59

Sissy In Glasses Gets Fucked Brutally

1 year ago

ShemaleZ

glasses, sissy
04:41

Cute tight asian sissy schoolgirl bareback fucked

5 years ago

HClips

cute, tight, sissy
04:01

Tiny Clitty Sissy Fuckslut Chantal Sweet

2 years ago

xHamster

small cock, sissy
09:48

Beautiful Sissy in chastity luvs being smashed

4 years ago

VideoSection

sissy, chastity, couple
10:30

Sissy Fuck Meat Has Fun With Her Machine

1 year ago

HClips

stockings, machine, sissy
20:57

Femboy Futanari Ass Fucks Sissy Pornstar Gape Her Ass Hard Till Sissygasm

1 year ago

Upornia

amateur, stockings, futanari, sissy, femboy, ladyboy
04:45

Blue Sissy Slut Hard Anal Lolafrina

3 years ago

ShemaleZ

crossdresser, slut, sissy
16:11

Crossdresser Sissy (two)

5 years ago

ShemaleZ

crossdresser, sissy
06:09 91%

Beautiful dark-hued Big arse Ebony Domme mistress Megan Gargle Strapon Pegging Twink White Guy Vanilla Cakez In His Sissy Ass With Her Big Back Cock While Hes Ductaped BDSM

1 year ago

ShemaleTaxi

ebony, femdom, teen (18+), strapon, bondage, BDSM, pegging
11:24

Teen Sissy Cums In Chasity Belt

3 years ago

ShemaleZ

fetish, sissy
05:23

Kim fickt Sissy

4 years ago

VideoSection

sissy
03:25

Rock Hard Pegging Sissy Pulverize

1 year ago

KeekAss

crossdresser, pegging, sissy
02:45

Ultra-Cute Smallish Bunny Wanks Sissy Man Meat Until She Ejaculates

3 years ago

KeekAss

cute, sissy, crossdresser
10:57 81%

Cute Petite Tranny Latina Dances Like A Sissy For You To Enjoy 11 Min

1 year ago

HClips

cute, dance, ladyboy, latina, webcam, sissy
15:46

Sissy Maid Sindi - Sissy Faggot Trainer

5 years ago

ShemaleZ

mature, maid, sissy
01:39 76%

Crossdresser Cums from her Sissy Clit while Giving Blow

3 years ago

AShemaleTube

crossdresser, clit, sissy
06:25

Allison Lace: without a condom Sissy superslut

2 years ago

ShemaleTaxi

condom, sissy
04:36

Goth Sissy Cum eating training

11 months ago

JizzBunker

strapon, train, couple, dildo, BDSM, cumshot, goth
02:15

Cumming through panties

1 year ago

xHamster

teen (18+), cumshot, panties, sissy, hands free, chastity, femboy
01:43

Sissy First Time Piss Drinking

5 months ago

AShemaleTube

pissing, sissy
14:55 88%

Fucked my cute slutty sissy femboy at home

10 months ago

xHamster

amateur, cute, teen (18+), teen anal (18+), sissy, femboy
02:34 62%

IT SISSY - PMV

5 months ago

AShemaleTube

shemale, anal, asian, compilation, cumshot, chinese, domination
04:49

Sissy Forced To Suck!

2 years ago

ShemaleZ

fetish, sissy
06:22

Sissy in green pantyhose gets penetrated in open thigh missionary

2 months ago

ShemaleTaxi

amateur, homemade, pantyhose, stockings, shemale, lingerie, BDSM
04:21

Femboy fucked hard by boyfriend Feminine trap girl riding bf

4 months ago

AShemaleTube

amateur, shemale, crossdresser, shemale and girl, riding, sissy, femboy
06:47

Rectal Trans Fruit Puding!

1 month ago

ShemaleTaxi

sissy, crossdresser, femboy, amateur, BDSM
13:22 86%

Sissy Femboy Maid Fucked To Orgasm

3 years ago

ShemaleZ

orgasm, maid, sissy, femboy, big cock, bareback
16:40

Amateur sissy fuck

7 years ago

TXXX

sissy
07:38

Hot Sissy Sucking and Fucking

7 years ago

ShemaleZ

sissy
56:59 58%

Bbc 4 sissy

1 year ago

JizzBunker

BBC, sissy
11:33

A TS Huge Meat Wrecks Da Clam Of tiny babe Lindsay love!

3 months ago

ShemaleTaxi

big cock, sissy, huge dildo, babe, swallow, orgasm
13:07

Sissy Pov – Slave Anna Mature Sissy Is So Sweet - Sissy Sweet

2 years ago

ShemaleZ

mature, crossdresser, sissy
08:34

BENVENUTA SISSY (ITA)

4 years ago

HDSex

outdoor, BDSM, sissy
17:36

French Maid pulverizes ladyboy

5 years ago

HDSex

french, prostate, maid, crossdresser, sissy
04:47 55%

Sissy Fag Maker

3 years ago

xHamster

JOI, sissy
06:36 88%

Tranny Mommy fucking transvestite Sissy Step-Son, 3D Cartoon

4 years ago

xHamster

mom, blowjob, 3D, masturbation, cartoon, domination, sissy
08:43

Sandra takes shaft up her sissy ass

3 years ago

ShemaleTaxi

british, sissy
18:48

How to become a sissy cockslut

3 years ago

TrannyGem

uniform, compilation, cum in mouth, skinny, sissy
02:10

Chastity Orgasm - PMV By HoloPMV

9 months ago

AShemaleTube

shemale, orgasm, crossdresser, cumshot, sissy, chastity
14:54 76%

Sissy find a wood in the woods and swallow his jizz

3 years ago

KeekAss

outdoor, crossdresser, swallow, sissy
06:18 63%

Blond White Tranny with enormous Ass Gets Fucked by BBC and wails in High high-heeled slippers and Stockings - Candy Ass Sissy

1 year ago

ShemaleTaxi

amateur, BBC, sissy
11:31

I need my sissy asshole fucked deep and hard

10 years ago

xHamster

sissy
02:33

Very cute sissy getting it in ass

5 months ago

AShemaleTube

cute, sissy
05:39

Blowing and plowing random meatpipes at the gloryhole

1 year ago

ShemaleMovie

gloryhole, crossdresser, swallow, sissy
26:11

Big Daddy Fucks Sissy

7 years ago

ShemaleZ

sissy
07:39 81%

Lola says: jizm with me ;) sissy cd milks and sploogs

1 year ago

TrannyGem

cute, crossdresser, JOI, sissy
05:28 85%

Trans lezzies - Jessica Bloom fucks Jenby Doll And Licks jizz Off Her Clitty

4 months ago

ShemaleTaxi

amateur, beauty, small cock, anal, ladyboy, crossdresser, british
08:19

Ideal Sissy Whore Ass

2 years ago

ShemaleZ

whore, sissy
02:17 88%

I had to show him my secret ASSet...

10 months ago

AShemaleTube

amateur, shemale, anal, domination, bareback, sissy, femboy
11:27

Shemale Perv River Enza Wrecks Her bum With Her Own forearm!

1 month ago

ShemaleMovie

solo, swallow, big cock, sissy, dildo, creampie
04:23

Sissy hypno 114

6 months ago

AShemaleTube

sissy
03:20

Sissy

4 years ago

xHamster

sissy
09:29

Sissy swap Tales student Sissies 2

4 years ago

VideoSection

student, sissy
08:03

Minidress Babe Loves Being Fucked

1 year ago

xHamster

machine, sissy, femboy, cum while fucked
49:49

Shemale sissy twinks traps groupsex mutual fuck

7 years ago

TXXX

sissy
10:08

Why do I suddenly love trannies

1 year ago

AShemaleTube

homemade, stockings, ladyboy, bareback, sissy, femboy
03:25

Maid sissy 6

3 years ago

AShemaleTube

maid, uniform, sissy
07:40

Lady Nina Birch - Pretty Frilly Sissy Part 1

5 years ago

ShemaleZ

sissy
10:17

Cute Asian teen shows her tranny bubble butt on webcam

2 years ago

TrannyOne

cute, sissy
05:55

Sissy crossdresser stroking with fuck stick, blasting cum

3 years ago

ShemaleTaxi

crossdresser, taxi, sissy
06:18

Big black cock worship trainer hypno

3 years ago

ShemaleTaxi

smoking, train, BBC, sissy
03:35

Analcumbunny Pmv Sissy World

3 years ago

ShemaleZ

group, sissy
07:45

Misr4 - fleshlight cumshot

1 year ago

xHamster

handjob, orgasm, cumshot, sissy, fleshlight
13:16

Sissy hypno 140

5 months ago

AShemaleTube

sissy
09:15

Crossdresser Tgirl sucks cock, plays with bootie, uses fucktoys, femboy tart needs dick chrissy cocoabutter

6 months ago

ShemaleMovie

blowjob, crossdresser, femboy, sissy, shemale
04:39 88%

Punished And Fucked Xhqtfb3 With Sissy Slave And Harley Quinn

2 years ago

HClips

POV, sissy
17:46

Sissy Hooker Gets Fucked By Large Lad, Short Footjob And Facial At The End

3 years ago

HClips

hooker, footjob, facial, sissy
05:50

Quinn Naughty Hot Ass Sissy Takes Raw Dick

3 months ago

ShemaleZ

shemale, sissy

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