Bondage Spitroast Caning Pt3
3 years ago
9:20

ShemaleZ

Bondage Spitroast Caning Pt3

Tags: 3some, caning, fetish, stockings, toys

Dominatrix caning useless slave
2 years ago
6:03

TrannyOne

Dominatrix caning useless slave

Tags: big tits, caning, dick, fetish, toys

The Spanking Ritual: baring my big ass
5 years ago
14:07

PornHub

The Spanking Ritual: baring my big ass

Tags: ass, caning, solo, spanking, submissive

Feminized Pain Toy
2 years ago
2:58

TrannyOne

Feminized Pain Toy

Tags: blonde, caning, hd, toys, whip

Very hard caning
3 years ago
4:25

aShemaleTube

Very hard caning

Tags: bitch, caning, crossdressing, hd

Tinasback caning
3 years ago
2:23

KeekAss

Tinasback caning

Tags: anal, caning, crossdressing, stockings, toys

Sir caning me as I inhale his weenie
3 years ago
4:12

KeekAss

Sir caning me as I inhale his weenie

Tags: brunette, caning, dick, masturbation, stockings

Daddy's sissy attends stern Mistress for discipline caning
4 years ago
3:29

ShemaleZ

Daddy's sissy attends stern Mistress for discipline caning

Tags: caning, daddies, mistress, sissy

Strap On Caning For Candi Cumdump - Stella Liberty - Femdom Female Domination Pegging Sissy Training
3 years ago
20:50

ShemaleZ

Strap On Caning For Candi Cumdump - Stella Liberty - Femdom Female Domination Pegging Sissy Training

Tags: caning, domination, fetish, hd, sissy

Crossdresser caning
3 years ago
6:08

aShemaleTube

Crossdresser caning

Tags: caning, crossdressing, hd

Bondage Spitroast Caning Pt2
3 years ago
4:27

ShemaleZ

Bondage Spitroast Caning Pt2

Tags: 3some, bondage, caning, fetish, stockings

sissy candy cane stuffer part 2
2 years ago
2:44

TrannyOne

sissy candy cane stuffer part 2

Tags: anal, ass, caning, crossdressing, hd

300 + 1
3 years ago
11:38

ShemaleSin

300 + 1

Tags: caning, hardcore, spanking

severe caning for nicole
3 years ago
2:20

aShemaleTube

severe caning for nicole

Tags: anal, caning, hd, slut, spandex

CD Sissy ass caned hard
5 years ago
6:28

aShemaleTube

CD Sissy ass caned hard

Tags: ass, caning, crossdressing, sissy, spanking

sissy caning
7 years ago
2:03

xHamster

sissy caning

Tags: bdsm, caning, sissy

Discipline Day For Joanne  1  The Pre Caning Warm Up
2 years ago
9:14

TrannyOne

Discipline Day For Joanne 1 The Pre Caning Warm Up

Tags: blowjob, caning, hd, masturbation, spanking

Ebony lesbian master teaching this little slut for good behaviour
1 year ago
30:21

TrannyOne

Ebony lesbian master teaching this little slut for good behaviour

Tags: amateur, bdsm, black, caning, ebony

Strap On Caning for Candi Cumdump - Stella Liberty - Femdom Female Domination Pegging Sissy Training
3 years ago
21:16

PornHub

Strap On Caning for Candi Cumdump - Stella Liberty - Femdom Female Domination Pegging Sissy Training

Tags: anal, caning, fetish, toys, transsexual

Blonde sissy Charlotte punished with intense spanking and caning by master Mike
1 year ago
37:46

ShemaleTaxi

Blonde sissy Charlotte punished with intense spanking and caning by master Mike

Tags: amateur, bdsm, blonde, caning, crossdressing

Both Girls Get Whipped Together By Their Mistress
8 years ago
14:59

PornHub

Both Girls Get Whipped Together By Their Mistress

Tags: 3some, bdsm, caning, fetish, lezdom

Big-Titted trans honeys pummel in insane three-way after caning
2 years ago
8:00

KeekAss

Big-Titted trans honeys pummel in insane three-way after caning

Tags: anal, blowjob, brunette, hd, transsexual

Fashion Show With Caning And Double Spunk Flow
48 days ago
9:00

ShemaleSin

Fashion Show With Caning And Double Spunk Flow

Tags: amateur, caning, cumshot, german, high heels

Dom trans babe blown before fucking sub butt then cums over his face
3 years ago
6:15

aShemaleTube

Dom trans babe blown before fucking sub butt then cums over his face

Tags: ass, babe, blowjob, caning, cum

Shemale caning
3 years ago
2:23

ShemaleSin

Shemale caning

Tags: amateur, domination, mature, stockings, transsexual

Trans Nubile Jizzes Firm After Caning His Meatpipe
1 year ago
11:07

KeekAss

Trans Nubile Jizzes Firm After Caning His Meatpipe

Tags: amateur, caning, fetish, hd, masturbation

Meet Filth Cupcake Pt 2 Teaser with MsAndrie
4 years ago
0:29

PornHub

Meet Filth Cupcake Pt 2 Teaser with MsAndrie

Tags: ass, bdsm, bondage, caning, chinese

Sissy hard spanking long version
3 months ago
2:05

aShemaleTube

Sissy hard spanking long version

Tags: caning, hd, sissy, spanking

Twunk marionette flogged by Latin Ladyboy Transwoman Mistress Michelly Ximenez numerous whips & cropping
1 year ago
39:49

KeekAss

Twunk marionette flogged by Latin Ladyboy Transwoman Mistress Michelly Ximenez numerous whips & cropping

Tags: amateur, ass, hd, transsexual, whip

Caning my tits while masturbating
2 years ago
10:41

PornHub

Caning my tits while masturbating

Tags: amateur, fetish, masturbation, solo, transsexual

Meet Filth Cupcake Pt 1 Teaser with MsAndrie and SaiJaidenLillith
4 years ago
0:57

PornHub

Meet Filth Cupcake Pt 1 Teaser with MsAndrie and SaiJaidenLillith

Tags: ass, bdsm, caning, fetish, kinky

Dominatrix Mistress April - Horny Sissy Slut
1 year ago
11:13

PornHub

Dominatrix Mistress April - Horny Sissy Slut

Tags: amateur, anal, big ass, big tits, caning

self caning was ok but I missed a dong in my bum
2 years ago
5:06

ShemaleSin

self caning was ok but I missed a dong in my bum

Tags: amateur, cumshot, german, lingerie, masturbation

t-girl caning thrashing jerking off spunk fountain
2 years ago
3:32

ShemaleSin

t-girl caning thrashing jerking off spunk fountain

Tags: amateur, ass, bdsm, cumshot, european

Bondage Electro Spitroast Caning Pt1
3 years ago
5:47

ShemaleZ

Bondage Electro Spitroast Caning Pt1

Tags: bdsm, caning, domination, latex, toys

CANING and SMACKING my cool horny MARIONETTE - SADISM & MASOCHISM
1 year ago
13:13

KeekAss

CANING and SMACKING my cool horny MARIONETTE - SADISM & MASOCHISM

Tags: amateur, ass, brunette, hd, transsexual

Sissy thrall T-Girl Danni punished and drilled by her Slavemaster. Wax play, caning ramrod, foot worship, and banging.
2 years ago
10:46

ShemaleSin

Sissy thrall T-Girl Danni punished and drilled by her Slavemaster. Wax play, caning ramrod, foot worship, and banging.

Tags: amateur, anal, banging, barebacking, bdsm

outdoor ejaculation with flogging caning
1 year ago
3:13

ShemaleSin

outdoor ejaculation with flogging caning

Tags: amateur, caning, cum, cumshot, german

Crossdresser caning
3 months ago
23:48

aShemaleTube

Crossdresser caning

Tags: barebacking, caning, crossdressing, domination, fetish

Misty Cane upskirt lingerie ass tease
2 years ago
4:30

TrannyOne

Misty Cane upskirt lingerie ass tease

Tags: amateur, ass, big cock, booty, caning

Headmistress left Sissy Maid in recent str8 jacket to struggle as that babe got willing for a night of whipping /spanking /caning and teasing /torment
2 months ago
6:37

ShemaleSin

Headmistress left Sissy Maid in recent str8 jacket to struggle as that babe got willing for a night of whipping /spanking /caning and teasing /torment

Tags: babe, bdsm, beauty, bondage, caning

Cunt plugged, nipples clamped, for a self caning and thigh and pussy cropping session
3 years ago
11:53

PornHub

Cunt plugged, nipples clamped, for a self caning and thigh and pussy cropping session

Tags: clamp, nipples, pussy, solo, transsexual

Now I can only watch fucking! I want this slut too!
2 years ago
24:31

TrannyOne

Now I can only watch fucking! I want this slut too!

Tags: bdsm, big cock, blowjob, caning, close up

tgirl caning jerking off spunk fountain high heels nylon silk
2 years ago
4:06

ShemaleSin

tgirl caning jerking off spunk fountain high heels nylon silk

Tags: amateur, caning, cumshot, doctor, european

Beauty Slaves Dominated by a Heartless Tranny
3 years ago
19:02

ShemaleSin

Beauty Slaves Dominated by a Heartless Tranny

Tags: beauty, bondage, caning, domination, dominatrix

t-girl waking flogging ejaculation in different stylings
1 year ago
8:29

ShemaleSin

t-girl waking flogging ejaculation in different stylings

Tags: amateur, bdsm, compilation, cumshot, european

Caning My Giant Clit - Pussy Suction + Using A Cane On My Swollen Huge Clit
5 months ago
14:58

ShemaleZ

Caning My Giant Clit - Pussy Suction + Using A Cane On My Swollen Huge Clit

Tags: amateur, caning, clit, fetish, hd

Caning my MASSIVE Clitoris - Vagina Suction + Using a Cane on my swollen GIANT Love Button
7 months ago
15:23

ShemaleSin

Caning my MASSIVE Clitoris - Vagina Suction + Using a Cane on my swollen GIANT Love Button

Tags: amateur, ass, bdsm, boy, caning

stroking transsexual in nylon nylons and skirt, hard self caning mandatory
1 year ago
3:45

ShemaleSin

stroking transsexual in nylon nylons and skirt, hard self caning mandatory

Tags: amateur, bdsm, bisexual, caning, compilation

outdoor ejaculation in soaked sheer gown and nylon nylons
1 year ago
5:01

ShemaleSin

outdoor ejaculation in soaked sheer gown and nylon nylons

Tags: amateur, bdsm, caning, cumshot, european

Oct 15th 2022
1 year ago
13:49

ShemaleSin

Oct 15th 2022

Tags: amateur, big clit, birthday, caning, fetish

pointed nipples stretch greedily in the air while a tranny can be fucked horny by her boyfriend in the ass
1 year ago
22:39

TrannyOne

pointed nipples stretch greedily in the air while a tranny can be fucked horny by her boyfriend in the ass

Tags: amateur, anal, ass, assfucking, boyfriend

just preparing with flogging, caning, masturbation and anal play
1 year ago
5:08

ShemaleSin

just preparing with flogging, caning, masturbation and anal play

Tags: amateur, anal, bdsm, caning, european

Buttfuck firm railing and self caning concludes in humungous stream after 1 week of edging
1 year ago
10:45

KeekAss

Buttfuck firm railing and self caning concludes in humungous stream after 1 week of edging

Tags: amateur, anal, solo, transsexual, webcam

Sub stuffs ginger in rectal hole, so the figged anus will burn, and canes undressed butt red whilst masturbating twat
1 year ago
0:51

ShemaleSin

Sub stuffs ginger in rectal hole, so the figged anus will burn, and canes undressed butt red whilst masturbating twat

Tags: amateur, anus, ass, bdsm, booty

If you lick my feet you can fuck me
1 year ago
17:04

TrannyOne

If you lick my feet you can fuck me

Tags: american, anal, big tits, blowjob, deep throat

Cropping my GIGANTIC Clittie - Twat Absorption + Using a Lash on my engorged MEATY Bud
5 months ago
15:23

KeekAss

Cropping my GIGANTIC Clittie - Twat Absorption + Using a Lash on my engorged MEATY Bud

Tags: amateur, bdsm, boy, caning, clit

Wow that enormous paddle was so severe,so painful it felt like punishment,I ended up very bruised. Got despairing for him to cum near the end,I just c
1 year ago
16:47

ShemaleSin

Wow that enormous paddle was so severe,so painful it felt like punishment,I ended up very bruised. Got despairing for him to cum near the end,I just c

Tags: amateur, anal, bdsm, bondage, caning

Randomizer Pain Game - Birthday Spanks
2 years ago
13:49

PornHub

Randomizer Pain Game - Birthday Spanks

Tags: ass, big clit, birthday, caning, game

Randomizer Pang Game - Birthday Spanks
2 years ago
13:06

ShemaleSin

Randomizer Pang Game - Birthday Spanks

Tags: big clit, birthday, caning, game, spanking

Randomizer Ache Game - Birthday Spanks
1 year ago
6:40

ShemaleSin

Randomizer Ache Game - Birthday Spanks

Tags: amateur, big clit, birthday, fetish, game

Caning my booty and balls
2 years ago
2:09

ShemaleSin

Caning my booty and balls

Tags: amateur, anal, balls, big cock, booty

Black TGirls - Chyna & Cane
2 years ago
15:06

TrannyOne

Black TGirls - Chyna & Cane

Tags: anal, anus, ass, bed sex, bedroom

Tranny slave bound and feet caned
1 year ago
5:19

TrannyOne

Tranny slave bound and feet caned

Tags: anal, anus, ass, bdsm, blowjob

Nicole is securely belted to the screw bench and has electrics applied to her chastity cage. This Babe is then given a priceless caning and screwing.
3 years ago
5:47

ShemaleSin

Nicole is securely belted to the screw bench and has electrics applied to her chastity cage. This Babe is then given a priceless caning and screwing.

Tags: anal, babe, bdsm, blowjob, british

transsexual jerking off drubbing caning
3 years ago
2:51

ShemaleSin

transsexual jerking off drubbing caning

Tags: amateur, bdsm, bisexual, jerking, lingerie

Teaching my bitch wife to a giant dildo... Funny, your cunt is mature but still tight! )) Come on slut, you can do it
1 year ago
10:17

TrannyOne

Teaching my bitch wife to a giant dildo... Funny, your cunt is mature but still tight! )) Come on slut, you can do it

Tags: amateur, big tits, bitch, brutal, caning

Twat Plugged, Teats Clamped, for a self Caning and Haunch and Cunt Cropping Session
3 years ago
11:54

ShemaleSin

Twat Plugged, Teats Clamped, for a self Caning and Haunch and Cunt Cropping Session

Tags: caning, clamp, cunt, domination, spanking

A skoolie awaiting to cane somebody
1 year ago
2:22

ShemaleSin

A skoolie awaiting to cane somebody

Tags: amateur, british, caning, european, fetish

caning my rump SADISM & MASOCHISM
1 year ago
2:23

KeekAss

caning my rump SADISM & MASOCHISM

Tags: amateur, bdsm, big ass, caning, crossdressing