TRANNY • CHASTITY 2,264 videos

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36:02

Crossdresser gets machine fucked with XXL Monster Dildos #2

5 months ago

xHamster

german, dildo, lingerie, crossdresser, monster
35:21 18%

Pink chastity

5 months ago

xHamster

chastity
08:12

So Many Dildos and Vibrators to Try Out

5 months ago

xHamster

crossdresser, femboy, chastity
07:02

Sissy virgin loser in ball weights and chastity angel Scarlett black

5 months ago

PornHub

amateur, sissy, chastity, solo
05:17

Man Put in Chastity and Dressed as Maid for Job

5 months ago

xHamster

BDSM, uniform, crossdresser, dress, domination, sissy, chastity
22:21

Smokin hot trans chick has anal orgasm while in chastity

5 months ago

PornHub

amateur, orgasm, bondage, solo, masturbation, anal orgasm, chastity
07:45

Part to of putting trying on the flat cage

5 months ago

xHamster

crossdresser, chastity, sissy
08:18

Horny shemale home alone in chastity cage

5 months ago

xHamster

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07:06

Sissy Slut hole showcase - MercurySissy aka Mercury Montana in chastity showing hole - trans solo

5 months ago

xHamster

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10:04

Caged sissy rides pink dildo with anal orgasms

5 months ago

xHamster

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11:12

Sissy Femboy Anal Masturbation Compilation - Chastity and Feminization Progress

5 months ago

xHamster

pantyhose, femboy, chastity
18:54

Kinky Trans Domme Gives You Pov Humiliation. Chastity Feet Girl Dick Verbal Degradation

6 months ago

HClips

feet, amateur
11:18

Trans Women Use Dildo, Butt Plug, Vibrator, Chastity and More

6 months ago

xHamster

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05:45

Sissy in Chastity Gets Fucked Hard by Dildo Sex Machine

6 months ago

xHamster

solo, chastity
27:31

Self Suspension Bondage - Sissy Maid

6 months ago

xHamster

latex, chastity, crossdresser, sissy, bondage
06:44

Chastity Shemale Gets Gaped by Dildo Fucking Machine

6 months ago

xHamster

solo, sissy, chastity
05:19

Sissy Ladyboy Chastity Training Getting Fucked Hard by Dildo Sex Machine

6 months ago

xHamster

anal
08:52

Luxia_tv, submissive and with the chastity cage

6 months ago

xHamster

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06:06

Sissy training - Dildo and electric chastity cum

6 months ago

xHamster

chastity, BDSM, domination
08:23

Slutty Shemale Rides Big Black Cock Sex Doll for Sissygasm

6 months ago

xHamster

big cock, BBC, chastity
05:54

Ts Girl Assfucks Her Boyfriend - Chastity Michaels

6 months ago

ShemaleZ

big tits, shemale and girl, ebony, chastity
07:09

Sissy Leona Plays with Her Ass and Clitty

6 months ago

xHamster

beauty, chastity, sissy
41:54

Sissy femboy in chastity cage ballbusts to hands free orgasm

6 months ago

xHamster

masturbation, chastity
05:14

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

6 months ago

xHamster

huge dildo, chastity, sissy, big cock, small cock, cumshot
19:19

Kinky Trans Domme gives you POV humiliation. Chastity, Feet, Girl Dick, Verbal Degradation.

6 months ago

PornHub

mature, amateur, feet, smoking, POV, solo, shemale and girl
05:13

CD Lacy Rose Butt Plug, Dildo & Tail.

6 months ago

xHamster

homemade, chastity, heels
07:51

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

6 months ago

PornHub

amateur, chastity, pissing
07:12

Sissy's anal dildo challenge

6 months ago

xHamster

chastity
05:54

Multiorgasm sissy riding dildo

6 months ago

xHamster

chastity, sissy, crossdresser
07:39

Fuck machine makes me cum in chastity!!

6 months ago

xHamster

chastity, machine
07:17

Niqab shemail locked in chastity and fucking dildo

6 months ago

xHamster

small cock, chastity
07:25

Knotting my bad dragon taking a tall boy can and a wine bottle all the way in my ass deep. Think you could wear me out?

6 months ago

xHamster

fetish, shemale
06:38

Fat Sissy cums in inverted cage after 3 weeks of chastity

6 months ago

xHamster

fat, german, chubby, BBW, masturbation, chastity
08:50 46%

Slut Cums Into her Own Mouth, Multiple Sissygasms, While Sounding, Vibrator on Her Chastity Cage, In the Woods, Etc!

6 months ago

xHamster

small cock, public, solo, cum in mouth, skinny, chastity
22:39

Sissy in chastity pushing bananas in and out of her boipussy

6 months ago

xHamster

pantyhose, stockings, mexican, asshole, chastity
09:45

Sissy Marissa buys a fuck machine

6 months ago

xHamster

chastity, crossdresser, sissy, machine
12:43

Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF

6 months ago

PornHub

amateur, strapon, threesome, bareback, double penetration, chastity
08:08

Cute trans girl fuck machine in chastity

6 months ago

PornHub

POV, chastity, amateur, teen anal (18+), solo, shemale and girl
10:24

Sissy Marissa trainning her hole for use

6 months ago

xHamster

small cock, sissy
07:29

Cheerleader femboy trying to cum in chastity with toys

6 months ago

xHamster

vibrator, POV, crossdresser, femboy
07:18

Cute Crossdresser Leopard Dress and Red Heels

6 months ago

xHamster

big ass, lingerie, crossdresser, heels, dress, chastity
05:56

Sissy using fuck machine to try and cum in chastity

6 months ago

xHamster

webcam, chastity
05:21

Chastity sissy trying to cum

6 months ago

xHamster

chastity
05:16

How to wear a flat chastity cage

7 months ago

xHamster

italian, webcam, sissy, chastity
07:23

F Machine Alpha Fucks Sissy Asshole - Jessica Bloom Chastity Orgasm And Cum In Mouth

7 months ago

xHamster

feet, orgasm, cum in mouth, asshole, chastity
06:04

Sissy un pink chastity cage enjoys filling her ass with a huge dildo

7 months ago

xHamster

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09:53

Ebony ass play!

7 months ago

xHamster

BBW, ebony, black, chastity
12:18

Sissy Doll Risky Anal Masturbation in Pubilc Restroom with 3 Dildos

7 months ago

xHamster

amateur, latex, dildo, crossdresser, masturbation, sissy, chastity
09:53

Luzia_Tv, Anal show in chastity riding until we..

7 months ago

xHamster

cumshot, solo
10:33

Twink in dress, stockings and chastity play with his butt

7 months ago

PornHub

chastity, solo, stockings, amateur, dress
07:02

Cow Femboy In Chastity

7 months ago

ShemaleZ

stockings, femboy, chastity
05:19

Sissy taniax ride huge black dildo in the hallway

7 months ago

xHamster

black, sissy, solo, colombian, huge dildo, chastity
16:36

CarolineTV - Red head Self BDSM in chastity cage and nips clamps

7 months ago

PornHub

anal, chastity
06:06

Sissy bitch removes chastity and cums in an Abandoned House

7 months ago

PornHub

cumshot, chastity, amateur, solo, masturbation, public
16:06

Schoolgirl 18+ Crossdresser Desperately Tries To Cum Having A Chastity Cage (cum Replay In Slow-motion)

7 months ago

Upornia

18, chastity, crossdresser
05:46

Femboy Cums in Chastity

7 months ago

PornHub

cumshot, femboy, chastity, teen anal (18+)
06:02

Chastity butt plug dildo anal

7 months ago

xHamster

chastity, dildo
08:45

Sissy Femboy in Chastity Trains Holes with Dildo

7 months ago

PornHub

chastity, femboy, sissy, dildo
10:53

SissyCDMish - qos sissy camwhore with chastity cage, butt plug and dildo

7 months ago

PornHub

anal, teen anal (18+), dildo, 18, toys, sissy, chastity
06:46 72%

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

7 months ago

TXXX

amateur, stockings, lingerie, swallow, cumshot, machine, sissy
09:17

Vibrating My Clit Till It Escaped Chastity! Then I Kiss It!

7 months ago

Upornia

solo, vibrator
07:40

Trans goth bbgirl adaklein wants your cum so bad

7 months ago

xHamster

masturbation, goth, BBC, chastity, femboy
12:12

Sissy Marissa Plays with Herself

7 months ago

xHamster

shemale, crossdresser, chastity, latex, fetish
22:15

Sissy cums in chastity while taking 12” dildo

7 months ago

PornHub

shemale, dildo, masturbation, chastity, solo
05:24

Gurl in chastity doggy style dildo fuck

7 months ago

xHamster

amateur, small cock, femboy, big cock, sissy, chastity
05:36

Chastity trans fucks self with big toys

7 months ago

xHamster

cute, small cock, BDSM, sissy, chastity, femboy
10:55

SissyCDMish - qos sissy camwhore with chastity cage, butt plug and dildo

7 months ago

xHamster

shemale, anal, dildo, crossdresser, sissy, chastity
08:45

Femboy Fuckmachine Sexy Lingerie Electro Chastity

7 months ago

Upornia

lingerie, chastity, femboy, electro
17:19

Public humiliation locked, plugged, gagged, clamped and squirt

7 months ago

xHamster

outdoor, chastity, BDSM, sissy, public, fetish
07:28

Violet Chastity Chained To Fuck Machine

8 months ago

TXXX

amateur, chastity, machine, BDSM
09:43

Vibrating my clit, chastity fail ends in self suck!

8 months ago

xHamster

facial, selfsuck, cum in mouth, vibrator, chastity
07:10

Best Feminization Ever (clothes / Make Up / Boobs / Chastity / Nails / Plug / High Heels)

8 months ago

ShemaleZ

shemale, clothed, chastity, heels, lingerie
10:01

Trans Latex Hands Free Cum After Cum Sex Chastity Sex

8 months ago

ShemaleZ

shemale, latex, chastity, solo, hands free
08:42

Live-cam Replay - Pegging my Slave in Chastity ! Subsribe to see full Video of 1hour Mistress Julia

8 months ago

PornHub

amateur, femdom, blowjob, fetish, pegging, chastity
10:01

Very Hot Blonde Crossdresser In Chastity Fucked

8 months ago

ShemaleZ

crossdresser, amateur, stockings, chastity
05:18

Sissy selffuck with Dragon dildo

8 months ago

xHamster

anal, chastity
10:22

Dildo fuck with Dragon toy

8 months ago

xHamster

anal, dildo, chastity, sissy
27:59

Sissy Maids Self Suspension Bondage in Chastity

8 months ago

xHamster

maid, bondage, BDSM, sissy
08:45

Sissy Maid Strapped to Bed Spread Eagle in Chastity with Vibrating Sheath and Tens Unit

8 months ago

xHamster

maid, BDSM, sissy
09:41

Vibrating my clit till it escaped chastity! Then I kiss it!

8 months ago

PornHub

solo, amateur, feet
05:38

Trans cums so hard in chastity while fucking her hole

8 months ago

PornHub

amateur, chastity, solo, feet, cum while fucked
09:51

Showering In Steel Chastity And Latex

8 months ago

TXXX

latex, fetish, shower, chastity
07:10

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

8 months ago

PornHub

amateur, anal, cumshot, machine, sissy, hands free, chastity
07:13

Trans Latex After Cum Sex In Chastity

8 months ago

ShemaleZ

solo, chastity, big cock, fetish
14:38

Sissy In Chastity With Ripped Gym Pants And Getting Her Hole Destroyed

8 months ago

ShemaleZ

big ass, chastity, sissy, amateur
06:00

Sissy fucked hard while in chastity

8 months ago

xHamster

shemale, chastity, sissy, stockings, BBC
09:19

Sissy CD plays with Big Dildo Squirts in Chastity and does a Self Facial

8 months ago

PornHub

teen anal (18+), chastity
33:59

Trans Latex Hands Free Cum Chastity Fuck Piss Drinkung

8 months ago

ShemaleZ

shemale, hands free, chastity, latex
09:15

Sissy anal training in chastity with a fucking maschine

8 months ago

xHamster

sissy, chastity
07:04

Sissy in flat chastity cage and micro thong drinking two beers via anal at the open door

8 months ago

PornHub

solo, sissy, chastity
09:44

Chastity clip vs fuck machine equals sissygasm everytime

8 months ago

xHamster

fetish, chastity
10:39

Crossdresser in latex and a new chastity belt

8 months ago

PornHub

anal
10:44

Sissy Maid Struggling In New Armbinder And Steel Chastity Belt With 7 Dildo Locked Inside

8 months ago

ShemaleZ

sissy, latex, chastity, maid
09:42

Fuck machine vs chastity clip = Sissygasm!

8 months ago

PornHub

solo
33:20

Trans Latex Hands Free Cum Piss Drinking Chastity Fuck Xxxsamanthaphd

8 months ago

ShemaleZ

shemale, pissing, chastity, latex
16:09

Easter special

8 months ago

xHamster

shemale, amateur, chastity, sissy, smoking
11:52

Sissy Francis Malice - Little Time for Fun Before Wife Comes Back Home

8 months ago

xHamster

german, sissy, chastity
07:11

Hot Trans Woman In Chastity Fucked Cowgirl 7 Min With Kelsey Masters

8 months ago

ShemaleZ

latex, chastity
25:15

Francis Malice Sissy Dream 1

8 months ago

xHamster

big tits, shemale, german, solo, crossdresser
13:02 65%

Clark Delgaty - Heteroflexible - Femboy Kay La Soumise Gets Anal Creampied By For Chastity Cage Key

8 months ago

ShemaleZ

shemale, creampie, ladyboy, bareback, chastity, femboy
07:26

Cow femboy in chastity

8 months ago

PornHub

teen anal (18+), teen (18+), chastity, femboy
08:26

Anal Orgasm In Chastity Cage For A Tied Femboy

8 months ago

ShemaleZ

stockings, shemale, orgasm, BDSM, tied, anal orgasm, chastity
09:28

Sissy Fuckdoll Machine Bred

8 months ago

xHamster

machine, femboy, chastity, solo, sissy, crossdresser
11:58

Sissy Bunny changes out of soaked diaper, cums in pink panties with chastity cage

8 months ago

PornHub

chastity, sissy, pissing, panties, diaper
13:22

Sissy maid riding dildo in chastity and cumming while pegged by dom girlfriend

8 months ago

PornHub

cumshot, amateur, chastity, pegging
15:30

Glass Shower Door Dildo Fuck by Sissy Mindy

8 months ago

xHamster

crossdresser, sissy, shower, glasses
13:25

Teased Trans Girl Chastity and Anal Play

8 months ago

PornHub

shemale and girl, amateur, chastity, solo
33:32

Skyler Storm Anal Masturbation in Chastity

8 months ago

PornHub

amateur, chastity
07:05

Locked In Chastity Under My Pretty Pink Dress

8 months ago

PornHub

fetish, dress, small tits, chastity
05:11

Sisk Release Her Clit From Chastity Cage

8 months ago

Upornia

teen (18+), clit, chastity
07:58 42%

Cute Femboy In Chastity Ride My Big Cock

8 months ago

TXXX

amateur, cute, teen (18+), fetish, riding, chastity, femboy
08:46

Fat BBC dildo fills Sissy ass deep

8 months ago

xHamster

fat, dildo, toys, chastity, femboy, BBC
05:08

Sissy Alexy showing herself and teasing

8 months ago

xHamster

pantyhose, fetish, tease, finnish, chastity
05:55

Sissygasm in chastity with a horse dildo up her asshole (inverted chastity cage)

8 months ago

PornHub

public, asshole, chastity
14:21

New Boots and Armbinder - Sissy Maid Stuck in Bondage Again

9 months ago

xHamster

latex, bondage, boots, BDSM, chastity
06:42

I RIDE my DILDO in CHASTITY cage - Femboy CD ANAL Sissy Play Charlie Moon

9 months ago

PornHub

feet, french, riding, chastity, femboy
07:34

Violet Chastity Chained to Fuck Machine

9 months ago

xHamster

homemade, bondage, cuckold, machine, gape, chastity
06:18

Sissy in School Girl Onesie Takes Dildo Up Ass while in Chastity

9 months ago

xHamster

dildo, sissy, chastity, crossdresser
14:35

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

9 months ago

xHamster

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07:05

Candle Wax & Chastity Go Together like PB & Jelly

9 months ago

xHamster

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