• Feminization

  • »
  • Popular
  • all time
  • month
  • week
Sucking a dick and getting milk in my throat!
1 year ago
8:24

ShemaleSin

Sucking a dick and getting milk in my throat!

Tags: amateur, ass, ass to mouth, asslick, babe, bbw, belly

VERY HOT Crossdresser in Pink Chastity Fucked
33 days ago
9:53

aShemaleTube

VERY HOT Crossdresser in Pink Chastity Fucked

Tags: amateur, anal, ass, cage, crossdressing, feminization, hd

Elena Koslov Twerking Teaser #three
11 months ago
0:15

ShemaleSin

Elena Koslov Twerking Teaser #three

Tags: amateur, ass, blonde, feminization, fetish, pov, sissy

My Feminization Nearly Complete FULL
2 years ago
12:04

ShemaleSin

My Feminization Nearly Complete FULL

Tags: 3some, amateur, ass, brunette, couple, feminization, fetish

feminization 1
4 years ago
25:27

aShemaleTube

feminization 1

Tags: ass, feminization, mature, shemale, solo

Feminization - Sissy training - Sissy joi - Be compliant Faggot
1 year ago
24:53

ShemaleSin

Feminization - Sissy training - Sissy joi - Be compliant Faggot

Tags: amateur, big cock, compilation, domination, feminization, fetish, hd

Upskirt sissy walking throughout woods
5 months ago
5:35

ShemaleSin

Upskirt sissy walking throughout woods

Tags: amateur, anal, ass, big ass, brunette, fat, femdom

Raver Sissy femboy in chastity bangs BBC 4 Femdom Domme whilst that babe eats dinner, coarse anal wench 4/5
2 years ago
25:11

ShemaleSin

Raver Sissy femboy in chastity bangs BBC 4 Femdom Domme whilst that babe eats dinner, coarse anal wench 4/5

Tags: anal, assfucking, babe, big black cock, cuckold, dildo, femdom

Kym's PVC Bodysuit (trans, Hose, Crossdress, Legs, Heels, Transformation, Female Mask, Mask)
4 years ago
2:31

ShemaleSin

Kym's PVC Bodysuit (trans, Hose, Crossdress, Legs, Heels, Transformation, Female Mask, Mask)

Tags: ass, babe, blonde, cosplay, crossdressing, dress, feminization

SISSY SCREWED. CROSSDRESSER. TRAP. FEMINIZATION
3 years ago
2:17

ShemaleSin

SISSY SCREWED. CROSSDRESSER. TRAP. FEMINIZATION

Tags: amateur, anal, bondage, crossdressing, feminization, fetish, hardcore

Sissy cums in cage to hurting & banding it’s white ball white extinction BNWO gal scarlett ebony
3 years ago
13:10

ShemaleSin

Sissy cums in cage to hurting & banding it’s white ball white extinction BNWO gal scarlett ebony

Tags: amateur, black, blonde, cage, cum, cumshot, ebony

Bailey Wilde Feminized Into Cheerleader and Screwed by Mistresse Pixie
2 years ago
0:53

ShemaleSin

Bailey Wilde Feminized Into Cheerleader and Screwed by Mistresse Pixie

Tags: amateur, anal, assfucking, bdsm, cheerleader, femdom, feminization

Sissy Floozy Merits Humiliation and Public Exposure
2 years ago
0:30

ShemaleSin

Sissy Floozy Merits Humiliation and Public Exposure

Tags: amateur, anal, domination, feminization, fetish, humiliation, kinky

Mrs R Boudoir Visit (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)
4 years ago
3:43

ShemaleSin

Mrs R Boudoir Visit (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)

Tags: babe, bbw, beauty, brunette, crossdressing, dress, feminization

Anal training for dad's BBC
2 years ago
9:59

ShemaleSin

Anal training for dad's BBC

Tags: amateur, anal, ass, assfucking, big black cock, daddies, feminization

Large Ebony Weenie Feminization Coach for Constrained Sissy Lads (BBC) (Captions)
4 years ago
6:13

ShemaleSin

Large Ebony Weenie Feminization Coach for Constrained Sissy Lads (BBC) (Captions)

Tags: anal, big black cock, blowjob, coach, cumshot, ebony, feminization

Trans Bailey Wilde Drilled by Bang Machine
4 months ago
4:28

ShemaleSin

Trans Bailey Wilde Drilled by Bang Machine

Tags: amateur, anal, ass, drilling, feminization, fucking machine, homevideo

I got a weight bench to Assist grow my boobs and keep in shape during the time that going throughout my feminization process. then i thought why not t
2 years ago
3:40

ShemaleSin

I got a weight bench to Assist grow my boobs and keep in shape during the time that going throughout my feminization process. then i thought why not t

Tags: amateur, anal, ass, banging, booty, ebony, feminization

BBC make me and a ally In a sissy floozy
2 months ago
3:30

ShemaleSin

BBC make me and a ally In a sissy floozy

Tags: amateur, big black cock, blowjob, feminization, fishnet, interracial, lingerie

White sissy gets fucked in the ass with a big black dildo. Feminization, Punishment, Analysis
1 year ago
6:47

XXXDan

White sissy gets fucked in the ass with a big black dildo. Feminization, Punishment, Analysis

Tags: anal, ass, big ass, black, clit, dildo, feminization

Hot Crossdresser Reverse Cowgirl Drilled by Domina
2 years ago
5:13

ShemaleSin

Hot Crossdresser Reverse Cowgirl Drilled by Domina

Tags: amateur, anal, ass, assfucking, babe, bdsm, cowgirl

Tgirl's ass is fuced
4 years ago
0:44

aShemaleTube

Tgirl's ass is fuced

Tags: anal, ass, assfucking, barebacking, big cock, dick, feminization

guy gets feminized and ass fucked in prison by chick
4 years ago
18:06

ShemalePub

guy gets feminized and ass fucked in prison by chick

Tags: anal, ass, assfucking, boy, femdom, feminization, jail

Cute Pants Upskirt
2 years ago
13:03

ShemaleSin

Cute Pants Upskirt

Tags: crossdressing, cute, feminization, fetish, humiliation, kinky, outdoor

Trans Goddess Loves To Get Your Dick Hard
3 years ago
5:41

TrannyOne

Trans Goddess Loves To Get Your Dick Hard

Tags: amateur, ass, audition, babe, bdsm, beauty, big tits

Trans Gal Bouncing To Sissy Bimbo Captions
9 months ago
1:54

ShemaleSin

Trans Gal Bouncing To Sissy Bimbo Captions

Tags: big ass, bimbo, feminization, pornstar, sissy, toys, transsexual

Sissy tries to escape bindings
2 years ago
4:57

ShemaleSin

Sissy tries to escape bindings

Tags: amateur, anal, ass, big ass, fat, femdom, feminization

CROSSDRESSER COMPILATION GLAMOROUS LADYBOY SCREWED Sissy Chastity Screwed FEMDOM
4 years ago
9:06

ShemaleSin

CROSSDRESSER COMPILATION GLAMOROUS LADYBOY SCREWED Sissy Chastity Screwed FEMDOM

Tags: amateur, anal, anal fisting, bondage, compilation, crossdressing, cuckold

Chastity caged, leashed, blindfolded, and gagged, yielding femboy gets gaped by screw machine
9 months ago
19:55

ShemaleSin

Chastity caged, leashed, blindfolded, and gagged, yielding femboy gets gaped by screw machine

Tags: amateur, anal, anal toying, blindfolded, bondage, collar, creampie

Fuchsia Doll High Heels and Ebony Hose and Pink Garter
4 years ago
1:59

ShemaleSin

Fuchsia Doll High Heels and Ebony Hose and Pink Garter

Tags: ass, dildo, doll, ebony, feminization, garter belts, high heels

AlsoNicole breast growth, going into Further Feminization
4 years ago
3:40

TrannyOne

AlsoNicole breast growth, going into Further Feminization

Tags: amateur, american, bdsm, big tits, feminization, hd, ladyboy

Samantha sissy have joy with her schlong, this babe can cum and milking very well, feminization is inevitable, try to get milk from tits and weenie jo
2 years ago
2:29

ShemaleSin

Samantha sissy have joy with her schlong, this babe can cum and milking very well, feminization is inevitable, try to get milk from tits and weenie jo

Tags: amateur, babe, beauty, big cock, big tits, cum, cumshot

Lisa feminizes herself each day after work. Lisa wears her weenie cage around the clock for a successful feminization. This Babe pulls down her diaper
1 year ago
1:36

ShemaleSin

Lisa feminizes herself each day after work. Lisa wears her weenie cage around the clock for a successful feminization. This Babe pulls down her diaper

Tags: anal, anal toying, babe, cage, cunt, diaper, european

Ebony Mini Suit Juggsy
4 years ago
4:58

ShemaleSin

Ebony Mini Suit Juggsy

Tags: amateur, big tits, blonde, booty, dancing, ebony, fake tits

Reconditioning still in progress
2 years ago
1:27

ShemaleSin

Reconditioning still in progress

Tags: anal, femdom, feminization, fetish, masturbation, nipples, sissy

Hot Cheap Doxy from Street Wanted to Suck Rod- Full Episode on my Onlyfans (link in Bio)
4 years ago
0:28

ShemaleSin

Hot Cheap Doxy from Street Wanted to Suck Rod- Full Episode on my Onlyfans (link in Bio)

Tags: bdsm, blowjob, bondage, deep throat, domination, extreme, femdom

Crossdresser upskirt in public
25 days ago
2:43

ShemaleSin

Crossdresser upskirt in public

Tags: amateur, anal, ass, big ass, brunette, crossdressing, fat

Brandynette Brainwash Joy Button Dressup - Why Bambi ruins your expectations!
1 year ago
14:21

KeekAss

Brandynette Brainwash Joy Button Dressup - Why Bambi ruins your expectations!

Tags: amateur, anal, anita blue, cosplay, crossdressing, dress, feminization

Sissy rides sex tool cowgirl style
3 months ago
6:49

ShemaleSin

Sissy rides sex tool cowgirl style

Tags: amateur, anal, ass, big ass, cowgirl, denial, dildo

I am the prince of self-gratification. I like to share my progress whether in feminization or the progress of my selfsuck and selffuck. it's main
3 years ago
2:06

ShemaleSin

I am the prince of self-gratification. I like to share my progress whether in feminization or the progress of my selfsuck and selffuck. it's main

Tags: amateur, anal, barebacking, beauty, big cock, blowjob, compilation

Sissy Intro at home and pleasing BBC Dildo
3 months ago
13:01

aShemaleTube

Sissy Intro at home and pleasing BBC Dildo

Tags: amateur, anal, big black cock, cage, cuckold, dildo, feminization

Little transsexual beginnings of self feminization
2 years ago
0:19

ShemaleSin

Little transsexual beginnings of self feminization

Tags: amateur, feminization, fetish, pov, reality, transsexual

Crossdresser Bailey Wilde Banged by Sex Machine Missionary
4 months ago
3:34

ShemaleSin

Crossdresser Bailey Wilde Banged by Sex Machine Missionary

Tags: amateur, anal, crossdressing, feminization, fucking machine, homevideo, missionary

Will u be a fine sissy for Trans Domme Sasha? ???? @Sasha_de_Sade on all sites ;)
2 years ago
1:33

ShemaleSin

Will u be a fine sissy for Trans Domme Sasha? ???? @Sasha_de_Sade on all sites ;)

Tags: big cock, british, cage, feminization, fetish, masturbation, mistress

Female-Dom pegs sissy catgirl in booty
3 years ago
7:05

ShemaleSin

Female-Dom pegs sissy catgirl in booty

Tags: amateur, anal, assfucking, babe, booty, dominatrix, femdom

Marinatvfem Sissy Swimsuit
1 year ago
1:48

KeekAss

Marinatvfem Sissy Swimsuit

Tags: amateur, crossdressing, feminization, fetish, hd, homevideo, lingerie

Satanic Sissy Faggot Crossdresser
2 months ago
5:02

ShemaleSin

Satanic Sissy Faggot Crossdresser

Tags: amateur, anal, ass, bbw, bdsm, big ass, booty

doxy rides bbc sex tool
7 months ago
6:00

ShemaleSin

doxy rides bbc sex tool

Tags: amateur, anal, ass, big ass, big black cock, brunette, fat

Goddess Violet Presents: The Feminization of M
1 year ago
8:13

XXXDan

Goddess Violet Presents: The Feminization of M

Tags: amateur, bdsm, bondage, couple, dildo, feminization, fetish

Self- exposures video porn 2
6 years ago
0:54

aShemaleTube

Self- exposures video porn 2

Tags: bimbo, feminization, shemale, sissy

VTL - Visible belt line
2 years ago
4:15

ShemaleSin

VTL - Visible belt line

Tags: amateur, feminization, fetish, kinky, outdoor, panties, public

Sissy has to crawl
2 years ago
1:58

ShemaleSin

Sissy has to crawl

Tags: amateur, anal, assfucking, buttplug, feminization, fetish, humiliation

Sissy Doxy in a Reverse Cowgirl Position Wearing Red High Heels and a Flat Chastity
4 months ago
0:12

ShemaleSin

Sissy Doxy in a Reverse Cowgirl Position Wearing Red High Heels and a Flat Chastity

Tags: amateur, anal, ass, close up, cowgirl, cuckold, dildo

attempting on stocking
1 year ago
1:11

KeekAss

attempting on stocking

Tags: amateur, anal, ass, bed sex, big ass, big cock, brunette

Femboy Elena Koslov's Tentacle Sex tool Teaser #1
11 months ago
0:24

ShemaleSin

Femboy Elena Koslov's Tentacle Sex tool Teaser #1

Tags: amateur, anal, anal toying, big ass, blonde, feminization, masturbation

Shy sissy slut anal training
1 year ago
2:24

aShemaleTube

Shy sissy slut anal training

Tags: anal, crossdressing, feet, feminization, hd, huge dildo, shemale

Small Oriental Trans Hotty Running Around In nature's garb (With Captions)
1 year ago
1:52

ShemaleSin

Small Oriental Trans Hotty Running Around In nature's garb (With Captions)

Tags: amateur, big cock, dancing, dick, feminization, nature, oriental

SOFIE AND VICKY BEING BREAKING IN BY 2 BBC! THEY HAD NO PITY! WE LOVE IT!
1 year ago
10:11

ShemaleSin

SOFIE AND VICKY BEING BREAKING IN BY 2 BBC! THEY HAD NO PITY! WE LOVE IT!

Tags: 4some, amateur, ass, bbw, big black cock, big cock, blowjob

Sissification Lecture "caged Sissy" Chastity Thongs, Jerk, Sissygasm by Mistresse Veronica Taboo
4 years ago
16:48

ShemaleSin

Sissification Lecture "caged Sissy" Chastity Thongs, Jerk, Sissygasm by Mistresse Veronica Taboo

Tags: big tits, cumshot, feet, feminization, fetish, sissy, taboo

Sissy BNWO castration bands its balls for headmistress 1hr goons white extinction beauty scarlett ebony
3 years ago
13:57

ShemaleSin

Sissy BNWO castration bands its balls for headmistress 1hr goons white extinction beauty scarlett ebony

Tags: balls, beauty, ebony, feminization, fetish, humiliation, masturbation

Close up sex tool quickie!
1 year ago
4:07

ShemaleSin

Close up sex tool quickie!

Tags: amateur, anal, ass, close up, fat, feet, feminization

Humiliation
2 years ago
3:21

ShemaleSin

Humiliation

Tags: crossdressing, cute, feminization, fetish, humiliation, kinky, panties

naughty sissy serah wanking preview
2 years ago
2:10

KeekAss

naughty sissy serah wanking preview

Tags: amateur, brunette, crossdressing, feminization, fetish, hd, ladyboy

Cute Sissy Femboy - Anal Large Vibrator - creampie - sissygasm - sissy climax - hands free cum
3 years ago
2:47

ShemaleSin

Cute Sissy Femboy - Anal Large Vibrator - creampie - sissygasm - sissy climax - hands free cum

Tags: anal, anal fisting, anal toying, bondage, creampie, cum, cumshot

Hot sissy girly dancing near couch in fantastic underware
3 years ago
4:29

ShemaleSin

Hot sissy girly dancing near couch in fantastic underware

Tags: boy, couch, dancing, fantasy, feet, feminization, fetish

Just playing around with me and try to learn how to look hawt as possible
2 years ago
36:11

ShemaleSin

Just playing around with me and try to learn how to look hawt as possible

Tags: anal, assfucking, bdsm, blowjob, bondage, feminization, fetish

Upskirt rosy underpants, abjecting
1 year ago
11:46

KeekAss

Upskirt rosy underpants, abjecting

Tags: amateur, anal, ass, big ass, crossdressing, fat, femdom

Needy Sissy in chastity cums by getting drilled by screw machine
1 year ago
4:50

ShemaleSin

Needy Sissy in chastity cums by getting drilled by screw machine

Tags: amateur, anal, cum, domination, drilling, feminization, fucking machine

I FOLLOWED A CHAP ON THE STREET AND ASKED HIM TO BREASTFEED - LUANA PRADO
1 year ago
11:15

ShemaleSin

I FOLLOWED A CHAP ON THE STREET AND ASKED HIM TO BREASTFEED - LUANA PRADO

Tags: amateur, cum in mouth, feminization, street, tranny, transsexual

I Am A FEMBOY and My Cool Garbs I Buy From Amazon And From Other Online Markets
2 years ago
21:15

KeekAss

I Am A FEMBOY and My Cool Garbs I Buy From Amazon And From Other Online Markets

Tags: amateur, beauty, big ass, blonde, crossdressing, femdom, feminization

Drilled in the butt
2 years ago
12:23

ShemaleSin

Drilled in the butt

Tags: amateur, anal, ass, assfucking, big black cock, dildo, drilling

Crossdresser gagged and anal
2 years ago
12:47

ShemaleSin

Crossdresser gagged and anal

Tags: amateur, anal, assfucking, crossdressing, dildo, feminization, fetish

TRANSSEXUAL W I L L O W - Let's Jizz Together Dad
2 years ago
5:45

KeekAss

TRANSSEXUAL W I L L O W - Let's Jizz Together Dad

Tags: amateur, big ass, blonde, compilation, crossdressing, cum, cumshot

Femboy gets concupiscent and screws a pocket cunt until JIZZ FLOW
1 year ago
0:28

ShemaleSin

Femboy gets concupiscent and screws a pocket cunt until JIZZ FLOW

Tags: amateur, blonde, cum, cumshot, cunt, feminization, jizz

Cute trans cutie cums whilst collared, wearing a hot suit
3 years ago
1:27

ShemaleSin

Cute trans cutie cums whilst collared, wearing a hot suit

Tags: amateur, collar, cum, cumshot, cute, femdom, feminization

Climax Series 1 (female mask, hose, mask, feminization, crossdress, trans, fetish, heels)
2 years ago
0:53

ShemaleSin

Climax Series 1 (female mask, hose, mask, feminization, crossdress, trans, fetish, heels)

Tags: crossdressing, feminization, fetish, high heels, kinky, mask, masturbation

47
1 year ago
2:54

KeekAss

47

Tags: amateur, anal, asian, big cock, boy, crossdressing, cum

Nice Sissy stiff fuck stick assfuck drill
1 year ago
1:01

KeekAss

Nice Sissy stiff fuck stick assfuck drill

Tags: amateur, anal, anal toying, assfucking, crossdressing, feminization, german

Turning husband into sissy slut
1 year ago
13:10

TrannyOne

Turning husband into sissy slut

Tags: amateur, anal, ass, asslick, femdom, feminization, fetish

May 20th 2022
3 years ago
13:10

ShemaleSin

May 20th 2022

Tags: amateur, black, blonde, cage, cum, cumshot, ebony

Movie Scene giving away some of my deepest transformation secrets ;)
3 years ago
15:39

ShemaleSin

Movie Scene giving away some of my deepest transformation secrets ;)

Tags: ass, blonde, crossdressing, feminization, fetish, kinky, mask

SISSY BITCH SEX TOOL TRAINING
1 year ago
9:19

ShemaleSin

SISSY BITCH SEX TOOL TRAINING

Tags: anal, babe, bitch, blonde, cuckold, cum, dildo

Sissy Giving Daddy Smoking Blowjob
3 years ago
17:02

TrannyOne

Sissy Giving Daddy Smoking Blowjob

Tags: amateur, blowjob, crossdressing, daddies, feminization, oral, shemale

Sissification Training "SISSY LOVE BUTTON MASTURBATION RULES" Mistresse Veronica Taboo and her Sissy Academy
3 years ago
10:15

ShemaleSin

Sissification Training "SISSY LOVE BUTTON MASTURBATION RULES" Mistresse Veronica Taboo and her Sissy Academy

Tags: cumshot, feminization, masturbation, pov, sissy, taboo, teacher

Candid upskirt
1 year ago
22:43

ShemaleSin

Candid upskirt

Tags: amateur, anal, ass, big ass, fat, femdom, feminization

Sissy Julia getting screwed by Fuckmachine in her live Cam Show - Trailer
8 months ago
0:20

ShemaleSin

Sissy Julia getting screwed by Fuckmachine in her live Cam Show - Trailer

Tags: amateur, anal, feminization, german, sissy, webcam

Crossdressing sissygasm brainwash feminization your mind in woman transformation shemale passive, are u actually homo? try a transgirl e transform you
2 years ago
5:39

ShemaleSin

Crossdressing sissygasm brainwash feminization your mind in woman transformation shemale passive, are u actually homo? try a transgirl e transform you

Tags: amateur, ass, beauty, big cock, compilation, crossdressing, cumshot

Is it Large Sufficiently to be Called a Real Ramrod? Or an Itty Bitty Clitty?
2 years ago
5:28

ShemaleSin

Is it Large Sufficiently to be Called a Real Ramrod? Or an Itty Bitty Clitty?

Tags: amateur, anal, babe, blonde, dildo, feminization, hardcore

Practicing for a real ramrod
51 days ago
6:34

ShemaleSin

Practicing for a real ramrod

Tags: amateur, anal, ass, big ass, brunette, fat, femdom

Sex sissy thrall Alina gets humiliation and hit on her face from Dad
1 year ago
1:47

ShemaleSin

Sex sissy thrall Alina gets humiliation and hit on her face from Dad

Tags: amateur, anal, ass to mouth, asslick, bitch, blowjob, feminization

Feminized Sissy Bangs Toy
1 year ago
5:02

ShemaleSin

Feminized Sissy Bangs Toy

Tags: amateur, feminization, masturbation, reality, sissy, small tits, solo

Fabulous trap drains in black stocking
2 years ago
6:00

KeekAss

Fabulous trap drains in black stocking

Tags: amateur, black, boy, crossdressing, feminization, handjob, hd

Delicious Sissy Dt Experience After Captions
1 year ago
2:50

KeekAss

Delicious Sissy Dt Experience After Captions

Tags: amateur, asian, blowjob, brunette, crossdressing, feminization, hd

Full version Sissy Wench Cums from Sextoy Whilst Playing DRAGON'S DOGMA two
9 months ago
31:04

ShemaleSin

Full version Sissy Wench Cums from Sextoy Whilst Playing DRAGON'S DOGMA two

Tags: anal, cum, cumshot, feminization, fetish, masturbation, orgasm

Sissy Crossdresser Trains to Dance in High Heels
4 years ago
8:02

ShemaleSin

Sissy Crossdresser Trains to Dance in High Heels

Tags: crossdressing, cuckold, dancing, feet, femdom, feminization, fetish

Sissy walks throughout the woods
1 year ago
8:02

ShemaleSin

Sissy walks throughout the woods

Tags: amateur, anal, ass, big ass, fat, femdom, feminization

Sissification Training "SISSY LOVE BUTTON MASTURBATION RULES" Headmistress Veronica Taboo and her Sissy Academy
2 years ago
9:56

ShemaleSin

Sissification Training "SISSY LOVE BUTTON MASTURBATION RULES" Headmistress Veronica Taboo and her Sissy Academy

Tags: amateur, cumshot, feminization, masturbation, pov, sissy, taboo

Trans chick drains off and whinges in lil' black sundress
1 year ago
0:53

KeekAss

Trans chick drains off and whinges in lil' black sundress

Tags: amateur, black, crossdressing, cute, feminization, fetish, hd

Mistresse Pixie Bangs Golden-Haired Honey Bailey Wilde
2 years ago
1:32

ShemaleSin

Mistresse Pixie Bangs Golden-Haired Honey Bailey Wilde

Tags: anal, bdsm, blonde, dominatrix, femdom, feminization, fetish

sissy da rica mamada a un dulce caramelo
1 year ago
4:51

KeekAss

sissy da rica mamada a un dulce caramelo

Tags: amateur, black, blowjob, brunette, crossdressing, feminization, hd

Cute Blond Sissy Stretches Her Backdoor out with Bang Machine
2 years ago
8:51

ShemaleSin

Cute Blond Sissy Stretches Her Backdoor out with Bang Machine

Tags: amateur, anal, ass, blonde, cute, dildo, feminization

Very first SissyGasm by BIG BLACK COCK - From Today this Sissy became a BIG BLACK COCK Sub
1 year ago
2:57

KeekAss

Very first SissyGasm by BIG BLACK COCK - From Today this Sissy became a BIG BLACK COCK Sub

Tags: amateur, anal, big ass, big black cock, brunette, creampie, crossdressing

Mischievous mexican trans taunt
1 year ago
4:12

KeekAss

Mischievous mexican trans taunt

Tags: amateur, asian, big ass, big black cock, boy, brazilian, brunette

Kylie's Climax (female Mask, Mask, Nylons, Garters, Trans, Crossdress, Feminization)
4 years ago
19:21

ShemaleSin

Kylie's Climax (female Mask, Mask, Nylons, Garters, Trans, Crossdress, Feminization)

Tags: big tits, brunette, cosplay, crossdressing, feminization, fetish, high heels

Kasnicole 314 穿丝袜自慰射精后鸡鸡消失雌堕成女生
1 year ago
10:03

ShemaleSin

Kasnicole 314 穿丝袜自慰射精后鸡鸡消失雌堕成女生

Tags: asian, big tits, cum, feminization, fetish, gloves, hd

Your sissy maid
2 years ago
19:47

ShemaleSin

Your sissy maid

Tags: amateur, anal, ass, big ass, british, fat, femdom

Sissy-crossdresser in the Forest is Awaiting for a Stranger and Screw his Butt
4 years ago
3:40

ShemaleSin

Sissy-crossdresser in the Forest is Awaiting for a Stranger and Screw his Butt

Tags: anal, ass, crossdressing, cuckold, feet, femdom, feminization

Sisk Feminization Training With Cutie Pinky Seifuku Ep3: Anal Play
2 years ago
8:00

getTranny

Sisk Feminization Training With Cutie Pinky Seifuku Ep3: Anal Play

Tags: anal, asian, brunette, cute, feminization, hd, lingerie

Candid upskirt, white pants
8 months ago
26:46

ShemaleSin

Candid upskirt, white pants

Tags: amateur, anal, ass, big ass, brunette, fat, femdom

Sissy Sex Toy Ride
2 years ago
4:22

ShemaleSin

Sissy Sex Toy Ride

Tags: amateur, anal, assfucking, dildo, feminization, fetish, humiliation

ガラス管を挿入したままオーガズム!ガラス管に精液があふれてくる。Climax with glass tube inserted! Jizz overflows into t
2 months ago
2:44

ShemaleSin

ガラス管を挿入したままオーガズム!ガラス管に精液があふれてくる。Climax with glass tube inserted! Jizz overflows into t

Tags: amateur, asian, ass, cum, cumshot, feminization, fetish

Hot Crossdresser Jerking Off in Las Vegas
58 days ago
5:08

ShemaleSin

Hot Crossdresser Jerking Off in Las Vegas

Tags: amateur, crossdressing, feminization, homevideo, jerking, sissy, tranny

Dec 15th 2022
2 years ago
25:12

ShemaleSin

Dec 15th 2022

Tags: amateur, booty, crossdressing, femdom, feminization, fetish, hd

My recent toy
10 months ago
3:51

ShemaleSin

My recent toy

Tags: amateur, anal, babe, feminization, masturbation, sissy, slut

Games playthings
1 year ago
10:33

KeekAss

Games playthings

Tags: amateur, anal, anal toying, ass, assfucking, babe, big ass

Gorgeous Trans Only Worshippers Woman with Ample Bootie On Web cam
11 days ago
9:23

KeekAss

Gorgeous Trans Only Worshippers Woman with Ample Bootie On Web cam

Tags: asian, ass, big ass, feminization, gorgeous, handjob, hd

Girlfriend Makes boyfriend to Suit as a Woman for the Weekend
4 years ago
0:33

ShemaleSin

Girlfriend Makes boyfriend to Suit as a Woman for the Weekend

Tags: amateur, babe, blonde, boy, boyfriend, femdom, feminization

Feminized Tranny Wants To Get Dicked Down
3 years ago
10:29

TrannyOne

Feminized Tranny Wants To Get Dicked Down

Tags: anal, anus, ass, bdsm, blowjob, booty, cum

A HOT TRANSVESTITE HIDES a METAL CHASTITY THONG UNDERNEATH TIGHTS AND a PETTICOAT AND GOES ON a DATE
4 years ago
9:00

ShemaleSin

A HOT TRANSVESTITE HIDES a METAL CHASTITY THONG UNDERNEATH TIGHTS AND a PETTICOAT AND GOES ON a DATE

Tags: bondage, crossdressing, feet, feminization, fetish, nylon, public

Feminized in Las Vegas
4 months ago
0:30

ShemaleSin

Feminized in Las Vegas

Tags: amateur, feminization, homevideo, shemale, sissy, transsexual

OnlyFans Trans Model With Feminization Captions
3 months ago
0:23

ShemaleSin

OnlyFans Trans Model With Feminization Captions

Tags: amateur, asian, babe, cute, feminization, model, pornstar

Oriental Sissy Ladyboy Tgirl Dancing and Showing her Hawt Body with Furry Coat
4 years ago
2:05

ShemaleSin

Oriental Sissy Ladyboy Tgirl Dancing and Showing her Hawt Body with Furry Coat

Tags: asian, boy, brunette, dancing, dick, feet, feminization

Soraya's Hawt Ebony Suit (trans, Crossdress, Female Mask, Mask, Transformation, Feminization_
4 years ago
14:42

ShemaleSin

Soraya's Hawt Ebony Suit (trans, Crossdress, Female Mask, Mask, Transformation, Feminization_

Tags: ass, babe, crossdressing, ebony, feminization, fetish, high heels

Crossdresser Willing to get Banged in Living Room
4 years ago
1:28

ShemaleSin

Crossdresser Willing to get Banged in Living Room

Tags: amateur, anal, babe, big tits, blonde, crossdressing, femdom

Feminization - sissy training - part two (english voice)
3 years ago
4:18

ShemaleSin

Feminization - sissy training - part two (english voice)

Tags: anal, big cock, bondage, british, english, femdom, feminization

TRANSIGENSE MOVIE SCENE 002 BABIGIRL Adult Comic Series
12 days ago
17:41

ShemaleSin

TRANSIGENSE MOVIE SCENE 002 BABIGIRL Adult Comic Series

Tags: comic, costume, feminization, skinny, small cock, solo, tiny dick

Candid upskirt booty
1 year ago
23:53

ShemaleSin

Candid upskirt booty

Tags: amateur, anal, ass, big ass, booty, fat, femdom

Sissy Doofy Whore - Result of Feminization Instructing
2 years ago
3:24

KeekAss

Sissy Doofy Whore - Result of Feminization Instructing

Tags: amateur, anal, assfucking, bimbo, blonde, crossdressing, feminization

Mistresse Ding-Dong pegs Her Sissy Bitch! SEXY anal pegging!!!
3 years ago
1:00

ShemaleSin

Mistresse Ding-Dong pegs Her Sissy Bitch! SEXY anal pegging!!!

Tags: anal, assfucking, bitch, femdom, feminization, fetish, pegging

Sissy Cunt Practice Session Using Realistic Anal Vibrator
4 months ago
0:16

ShemaleSin

Sissy Cunt Practice Session Using Realistic Anal Vibrator

Tags: amateur, anal, ass, close up, cuckold, cunt, dildo

Priceless CD femboy love and obey sissy tutor wash her brains with inhale
2 years ago
12:27

ShemaleSin

Priceless CD femboy love and obey sissy tutor wash her brains with inhale

Tags: amateur, anal, assfucking, blowjob, feminization, fetish, kinky

Romina's Gyrations (female Mask, Mask, Fetish, Trans, Crossdress, Transformation, Hose, Heels)
4 years ago
13:36

ShemaleSin

Romina's Gyrations (female Mask, Mask, Fetish, Trans, Crossdress, Transformation, Hose, Heels)

Tags: amateur, ass, brunette, crossdressing, feminization, fetish, high heels

Crossdresser maid doing abode chores
2 years ago
9:55

ShemaleSin

Crossdresser maid doing abode chores

Tags: amateur, anal, ass, big ass, crossdressing, fat, femdom

TRANSIGENSE MOVIE SCENE ONE: SKYKANDI
2 months ago
12:23

ShemaleSin

TRANSIGENSE MOVIE SCENE ONE: SKYKANDI

Tags: cop, costume, feminization, skinny, small cock, solo, tiny dick

Samantha sissy talk ribald 'cuz your knob is pathetic, the feminization is inevitable
3 years ago
6:56

ShemaleSin

Samantha sissy talk ribald 'cuz your knob is pathetic, the feminization is inevitable

Tags: amateur, babe, beauty, big tits, cumshot, european, feminization

Mrs R Sex Change (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)
4 years ago
18:21

ShemaleSin

Mrs R Sex Change (trans, Feminization, Female Mask, Mask, Crossdress, Transformation, big beautiful woman)

Tags: ass, babe, bbw, beauty, brunette, crossdressing, dress

Sissification feminization sissy training - FRESH GENDER (english voice)
3 years ago
3:12

ShemaleSin

Sissification feminization sissy training - FRESH GENDER (english voice)

Tags: anal, babe, british, english, femdom, feminization, masturbation

First time feminized and fucked
4 years ago
16:38

TrannyOne

First time feminized and fucked

Tags: amateur, anal, ass, barebacking, bdsm, big cock, blowjob

Dom CD Shemale Drag Queen Feminization Mastix become my Sissy Wench
4 years ago
2:58

ShemaleSin

Dom CD Shemale Drag Queen Feminization Mastix become my Sissy Wench

Tags: amateur, dick, feminization, masturbation, queen, shemale, sissy

Elena Koslov's Twerking Teaser #5
10 months ago
0:23

ShemaleSin

Elena Koslov's Twerking Teaser #5

Tags: amateur, ass, blonde, feminization, fetish, nude, sissy

Dude Feminized by Girlfriend
4 years ago
2:48

ShemaleSin

Dude Feminized by Girlfriend

Tags: amateur, babe, big tits, blonde, femdom, feminization, girlfriend

Sissy Mistresse Captions
3 years ago
1:42

ShemaleSin

Sissy Mistresse Captions

Tags: feminization, mistress, sissy, transsexual

Sissy walllrides her large sex tool
3 months ago
10:21

ShemaleSin

Sissy walllrides her large sex tool

Tags: amateur, anal, ass, big ass, dildo, doggystyle, feminization

Feminized and Spanked
3 years ago
5:29

TrannyOne

Feminized and Spanked

Tags: bdsm, crossdressing, domination, feminization, fetish, punishment, shemale

Sissy Emily
59 days ago
0:20

ShemaleSin

Sissy Emily

Tags: amateur, bbw, big ass, chubby, feminization, gay, humiliation

Grown Dude To Sissy Female Transformation
2 years ago
5:38

KeekAss

Grown Dude To Sissy Female Transformation

Tags: amateur, big cock, crossdressing, cum, cute, dirty, feminization

Feminization sissy self plow by fake penis and ass-plug
1 year ago
9:33

KeekAss

Feminization sissy self plow by fake penis and ass-plug

Tags: amateur, anal, asian, ass, big ass, crossdressing, cum

She-Male CUMSHOOT inbetween her thights
1 year ago
9:48

KeekAss

She-Male CUMSHOOT inbetween her thights

Tags: amateur, ass, beauty, big ass, big cock, big tits, blonde

Femboy Transsexual stretches her rectal hole with dragon jock
38 days ago
8:34

ShemaleSin

Femboy Transsexual stretches her rectal hole with dragon jock

Tags: amateur, anal, ass, british, dildo, feminization, hd

Prettyful Trans Sissy Biotch In Rosy Undergarments Gets Bitchy
1 year ago
9:20

KeekAss

Prettyful Trans Sissy Biotch In Rosy Undergarments Gets Bitchy

Tags: amateur, anal, bitch, brunette, crossdressing, feminization, fetish

Femdom Cuck has squirting climax in fake snatch
2 years ago
6:57

ShemaleSin

Femdom Cuck has squirting climax in fake snatch

Tags: creampie, cuckold, cum, cumshot, femdom, feminization, masturbation

Maid reading on her break
2 years ago
7:40

ShemaleSin

Maid reading on her break

Tags: amateur, anal, ass, big ass, fat, femdom, feminization

Training my butt for BBC
1 year ago
6:46

ShemaleSin

Training my butt for BBC

Tags: amateur, anal, ass, big ass, big black cock, fat, femdom

Sissy wench babysitter shows off smooth fem body
1 year ago
2:22

ShemaleSin

Sissy wench babysitter shows off smooth fem body

Tags: amateur, ass, babysitter, compilation, feet, feminization, fetish

MADE A CREAMY MESSS U WANT TO AID DAD ?
14 days ago
12:25

ShemaleSin

MADE A CREAMY MESSS U WANT TO AID DAD ?

Tags: ass, big ass, booty, creampie, dildo, fat, feminization

I own this FUCKSLUTS fuckholes!
3 months ago
28:05

KeekAss

I own this FUCKSLUTS fuckholes!

Tags: amateur, anal, big tits, femdom, feminization, fetish, handjob

Most Excellent of samantha sissy
4 years ago
3:11

ShemaleSin

Most Excellent of samantha sissy

Tags: amateur, big cock, big tits, feminization, italian, ladyboy, masturbation

Gina's Teaser
10 months ago
0:34

ShemaleSin

Gina's Teaser

Tags: amateur, babe, blonde, booty, feminization, fetish, high heels

Crossdresser Shackled and Banged by Slavemaster Stud (onlyfans/baileywilde)
3 years ago
0:59

ShemaleSin

Crossdresser Shackled and Banged by Slavemaster Stud (onlyfans/baileywilde)

Tags: amateur, anal, babe, bdsm, bondage, crossdressing, femdom

Sissy Femboy Page Madi James Drilled Doggy Position
4 years ago
3:04

ShemaleSin

Sissy Femboy Page Madi James Drilled Doggy Position

Tags: amateur, anal, big cock, blonde, creampie, doggystyle, drilling

Crossdresser Willing to Get Pegged by Headmistress Pixie
2 years ago
1:23

ShemaleSin

Crossdresser Willing to Get Pegged by Headmistress Pixie

Tags: amateur, anal, assfucking, babe, bdsm, crossdressing, dominatrix

SissyNewLifeStory - Sissy Transformation Story Movie Scene 1
4 years ago
16:36

ShemaleSin

SissyNewLifeStory - Sissy Transformation Story Movie Scene 1

Tags: bisexual, fantasy, feminization, masturbation, music, shemale, sissy

Amateur crossdresser removes her petticoat
7 months ago
29:52

ShemaleSin

Amateur crossdresser removes her petticoat

Tags: amateur, anal, ass, big ass, brunette, crossdressing, fat

Gina's Weenie & Vibe (trans, Crossdress, Female Mask, Mask, Transformation, Encasement, Fetish)
4 years ago
15:55

ShemaleSin

Gina's Weenie & Vibe (trans, Crossdress, Female Mask, Mask, Transformation, Encasement, Fetish)

Tags: big tits, brunette, cosplay, crossdressing, feminization, fetish, high heels

Apr 11th 2022
3 years ago
19:04

ShemaleSin

Apr 11th 2022

Tags: amateur, blonde, crossdressing, feminization, fetish, high heels, mask

Sophie krens sissyslut sissy sissyfaggot
11 months ago
1:21

ShemaleSin

Sophie krens sissyslut sissy sissyfaggot

Tags: anal, feminization, fetish, german, homevideo, masturbation, pornstar

Pegging my sissy bitch balls unfathomable
2 years ago
4:11

ShemaleSin

Pegging my sissy bitch balls unfathomable

Tags: anal, babe, balls, bitch, feminization, fetish, hardcore

Sissygasm - Joanna cums hands free - Bullet Sex-Toy on Clitoris - Feminization Sissy
1 year ago
5:34

ShemaleSin

Sissygasm - Joanna cums hands free - Bullet Sex-Toy on Clitoris - Feminization Sissy

Tags: amateur, clit, cum, feminization, masturbation, panties, pov

Trans upskirt caught while ambling
2 years ago
12:11

KeekAss

Trans upskirt caught while ambling

Tags: amateur, anal, ass, big ass, caught, crossdressing, fat

Arab Sissy Crossdresser takes facial cumshot from deep throat
2 years ago
2:21

KeekAss

Arab Sissy Crossdresser takes facial cumshot from deep throat

Tags: amateur, arab, blowjob, brunette, crossdressing, cum, cumshot

Positive Sissy Affirmation
2 years ago
4:16

FapCat

Positive Sissy Affirmation

Tags: amateur, compilation, crossdressing, feminization, hd, shemale, sissy

Upskirt, takes her petticoat off
1 year ago
29:24

ShemaleSin

Upskirt, takes her petticoat off

Tags: amateur, anal, ass, big ass, fat, femdom, feminization

Sissy displaying off
2 years ago
3:39

KeekAss

Sissy displaying off

Tags: amateur, anal, ass, big ass, crossdressing, fat, femdom

May 18th 2022
3 years ago
11:56

ShemaleSin

May 18th 2022

Tags: amateur, black, blonde, cage, cum, cumshot, cute

Sissy attempts to run away bindings
2 years ago
4:57

KeekAss

Sissy attempts to run away bindings

Tags: amateur, anal, ass, bdsm, big ass, crossdressing, fat

Sissy does butt to throat with her toys.
1 year ago
5:54

ShemaleSin

Sissy does butt to throat with her toys.

Tags: amateur, anal, ass, ass to mouth, blowjob, buttplug, deep throat

Vanessa Lux masturbation
6 years ago
0:51

aShemaleTube

Vanessa Lux masturbation

Tags: cum, cum swallowing, feminization, masturbation, mexican, shemale, sissy

Meaty bang for nice-looking sissy wench- full movie on my Onlyfans (link in bio)
4 years ago
0:18

ShemaleSin

Meaty bang for nice-looking sissy wench- full movie on my Onlyfans (link in bio)

Tags: anal, ass, assfucking, bdsm, blowjob, femdom, feminization

Cute femboy shaves her slim body and no hand spunk flow. Sissy shaves for her feminization process and cum out of hands by stimulating her prostate sp
3 years ago
16:13

ShemaleSin

Cute femboy shaves her slim body and no hand spunk flow. Sissy shaves for her feminization process and cum out of hands by stimulating her prostate sp

Tags: amateur, cum, cute, feminization, french, ladyboy, lingerie

CD Mask Film Noir
4 years ago
3:36

ShemaleSin

CD Mask Film Noir

Tags: amateur, big tits, black, fake tits, feminization, fetish, mask