New Tranny Videos Tagged with chastity

Most Viewed
Sissy Clitty Chastity Training 10:14
Sissy Clitty Chastity Training
Sissy in G-String and Chastity Fucked Hard 12:35
Sissy in G-String and Chastity Fucked Hard
cute sissy femboy stretches ass with alien dildo, inserts big tunnel plug and cums in chastity 8:17
cute sissy femboy stretches ass with alien dildo, inserts big tunnel plug and cums...
SISSY HYPNO - DOXY TRANSFORMATION 9:24
SISSY HYPNO - DOXY TRANSFORMATION
Chastity TS PMV 5:30
Chastity TS PMV
Sissy Chastity Slave Teased and Humiliated by Mistress, Denied and Locked in the Vice 12:29
Sissy Chastity Slave Teased and Humiliated by Mistress, Denied and Locked in the Vice
Kymmy has 1st Sissygasam in Chastity Ever! BIGGEST EJACULATION 18:06
Kymmy has 1st Sissygasam in Chastity Ever! BIGGEST EJACULATION
teasing trans chastity slave during locktober part 1 10:53
teasing trans chastity slave during locktober part 1
Sissy Training - Insight into my intimate training for sissies - What does online sissy training look like 22:29
Sissy Training - Insight into my intimate training for sissies - What does online ...
Become a Shemale Sex Slave sissy training instructions 12:58
Become a Shemale Sex Slave sissy training instructions
Wife Teases you about Locking you in Chastity like her TS Friend POV HJ SISSY TRAINING 13:42
Wife Teases you about Locking you in Chastity like her TS Friend POV HJ SISSY TRAI...
Sissy Training - Insight into my Intimate Training for Sissies - what does Online Training look like 22:30
Sissy Training - Insight into my Intimate Training for Sissies - what does Online ...
Sissy Training: Deepthroat, Anal & Sissygasm while Locked in Chastity 27:23
Sissy Training: Deepthroat, Anal & Sissygasm while Locked in Chastity
Sissy training: slut in chastity having fun on huge anal toys, multiple sissygasms 29:58
Sissy training: slut in chastity having fun on huge anal toys, multiple sissygasms
Natalie Mars and Charlotte Sartre Anal Play 12:10
Natalie Mars and Charlotte Sartre Anal Play
Kymmy Receives to Cum after 10 Days in Chastity at the Sissy Institute! 18:21
Kymmy Receives to Cum after 10 Days in Chastity at the Sissy Institute!
Sissy Fucks herself to Handsfree Sissygasm in Chastity Cage 5:05
Sissy Fucks herself to Handsfree Sissygasm in Chastity Cage
Sarina takes BBC in Perfect Total Sub Form 5:39
Sarina takes BBC in Perfect Total Sub Form
Femboy Sissy Gaping Ass and Riding Fuck Machine Hard - Sissy Jazzie 13:04
Femboy Sissy Gaping Ass and Riding Fuck Machine Hard - Sissy Jazzie
Sissy Slut Fucking Machine Anal Training and Huge Toys (long Version) 19:47
Sissy Slut Fucking Machine Anal Training and Huge Toys (long Version)
Soft Femboy Anal Play & Pee Ending 9:55
Soft Femboy Anal Play & Pee Ending
Goddess in chastity fists her perfect ass to orgasm 8:49
Goddess in chastity fists her perfect ass to orgasm
sissy dildo training 8:11
sissy dildo training
Sissy BNWO castration bands its balls for mistress 1hr goons white extinction angel scarlett black 13:57
Sissy BNWO castration bands its balls for mistress 1hr goons white extinction ang...
"I've Learned To Enjoy Not Cumming" Sissy Femboy Chastity & Self Foot Worship + CBT Tranny Ball Slap 9:32
"I've Learned To Enjoy Not Cumming" Sissy Femboy Chastity & Self Foot Wors...
Cute CD Femboy Has Hands-Free Sissygasm & Taste it After Riding Large DIldo 4:01
Cute CD Femboy Has Hands-Free Sissygasm & Taste it After Riding Large DIldo
Trap in Chastity Cage Anal 19:12
Trap in Chastity Cage Anal
Sissy in a cow's suit rides a dildo, squirts and cums hands free | Video by LevkoNoya 6:27
Sissy in a cow's suit rides a dildo, squirts and cums hands free | Video by LevkoNoya
Multiply SHEMALE CHASTITY SISSYGASM W/O Ejaculation - Anal Sex Machine Orgasm - Model Veronica Taboo 9:52
Multiply SHEMALE CHASTITY SISSYGASM W/O Ejaculation - Anal Sex Machine Orgasm - Mo...
TRANS SQUIRTING AND CUM COMPILATION!!! 14:05
TRANS SQUIRTING AND CUM COMPILATION!!!
Femboy in chastity sissygasm with dildo in her ass 9:33
Femboy in chastity sissygasm with dildo in her ass
Sissygasm - Cageful of Cum 11:29
Sissygasm - Cageful of Cum
Sissy maid does dishes with a vibrating plug and chastity 2:05
Sissy maid does dishes with a vibrating plug and chastity
Sissy maid in chastity with big fake tits rides dildo 6:00
Sissy maid in chastity with big fake tits rides dildo
Cute sissy in pink maid dress plays and cums on 50 cm butplug in chastity 15:05
Cute sissy in pink maid dress plays and cums on 50 cm butplug in chastity
Sissy Lucy being locked in metal Chastity for Locktober 19:00
Sissy Lucy being locked in metal Chastity for Locktober
Sissy in chastity playing with fuck machine 7:16
Sissy in chastity playing with fuck machine
Fuck machine cum in tiny chastity cage 7:52
Fuck machine cum in tiny chastity cage
Sissy Mara Jade's Sissygasms! (Entire Chastity Compilation!) 10:08
Sissy Mara Jade's Sissygasms! (Entire Chastity Compilation!)
Sissy Femboy Teases his Penis in Chastity with Vibrator 2:05
Sissy Femboy Teases his Penis in Chastity with Vibrator
Sissy Crossdresser Chastity BBC Sex Tool 9:43
Sissy Crossdresser Chastity BBC Sex Tool
Caged & Plugged Sissy in Selfbondage Straitjacket and a Harley Quinn Wig 31:30
Caged & Plugged Sissy in Selfbondage Straitjacket and a Harley Quinn Wig
Latex Gimpette Fuck Machine Frenzy 24:07
Latex Gimpette Fuck Machine Frenzy
Sissy in chastity pounding creampie fuckmachine 15:16
Sissy in chastity pounding creampie fuckmachine
A video of ejaculation by dressing up as a woman in a public toilet and doing anal masturbation. 15:03
A video of ejaculation by dressing up as a woman in a public toilet and doing anal...
[SISSY] I had him ejaculate in my face hole in a park in the daytime. 14:49
[SISSY] I had him ejaculate in my face hole in a park in the daytime.
Trans Sissy in Chastity Finger Fucks Ass and Rides a Thick Dildo 14:49
Trans Sissy in Chastity Finger Fucks Ass and Rides a Thick Dildo
Sergeant  caught Cheating W/ Slut Natalie Mars by Jasmeen LeFleur 30:44
Sergeant  caught Cheating W/ Slut Natalie Mars by Jasmeen LeFleur
Sissy Bitch Rides Sex-Toy In Chastity 11:37
Sissy Bitch Rides Sex-Toy In Chastity
Caged Orgasm for Femboy Rammed by Fucking Machine 10:00
Caged Orgasm for Femboy Rammed by Fucking Machine
Caged Trans Girl Rubs and Humps Wet and Messy Diaper and Can't Cum 7:59
Caged Trans Girl Rubs and Humps Wet and Messy Diaper and Can't Cum
Femboy sissy fucks dildo cums and eats it 13:43
Femboy sissy fucks dildo cums and eats it
Sissy in high heels and stockings fucks herself in a cowgirl position 16:39
Sissy in high heels and stockings fucks herself in a cowgirl position
Horny Goth Crossedressing Femboy Practices with a Dildo(voiced) 15:34
Horny Goth Crossedressing Femboy Practices with a Dildo(voiced)
Sissy chastity (part 1) 9:28
Sissy chastity (part 1)
Sissy slut gapes ass with thick dildo and fuck machine 12:23
Sissy slut gapes ass with thick dildo and fuck machine
Sissy crossdresser femboy ruins her own orgasm with hardcore ballbusting 9:03
Sissy crossdresser femboy ruins her own orgasm with hardcore ballbusting
Sissy Trap Blows her Fake Penis than Bonks it (Full Episode) 17:00
Sissy Trap Blows her Fake Penis than Bonks it (Full Episode)
Caged Femboy Gapes her Ass 6:33
Caged Femboy Gapes her Ass
Latex Femdom Lora Cross uses chastity sub for sounding release 5:03
Latex Femdom Lora Cross uses chastity sub for sounding release
Sissy Femboy acquire Screwed 18:08
Sissy Femboy acquire Screwed
Muzzled and Locked Transgirl Strapped by Goth Femdom 12:02
Muzzled and Locked Transgirl Strapped by Goth Femdom
TEEN SISSY CROSSDRESSER IN CHASITY BELT HANDSFREE ORGASM 14:35
TEEN SISSY CROSSDRESSER IN CHASITY BELT HANDSFREE ORGASM
femboy pushes out his buttplug 1:38
femboy pushes out his buttplug
I Fuck my Ass with a Cucumber and a Soda Can and have a Sissygasm Sissy Slut 9:43
I Fuck my Ass with a Cucumber and a Soda Can and have a Sissygasm Sissy Slut
BDSM mistress plays with her sissy girl 11:37
BDSM mistress plays with her sissy girl
Cute femboy locked in chastity have sissygasm 11:25
Cute femboy locked in chastity have sissygasm
Fucking myself with a 10 inch cock while locked in chastity 6:48
Fucking myself with a 10 inch cock while locked in chastity
Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage! 8:49
Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage!
Transgirl is Spit Roasted by her Girlfriend and Fucking Machine 29:59
Transgirl is Spit Roasted by her Girlfriend and Fucking Machine
SissyBoy - I Don't Need a Pussy to CUM ( SissyBoy life ) 2:40
SissyBoy - I Don't Need a Pussy to CUM ( SissyBoy life )
Trying the knot and the fist and fail 21:23
Trying the knot and the fist and fail
transgender sissy slave playing with her dildo ass fucking gape anal hole ass pussy on floor pink 21:47
transgender sissy slave playing with her dildo ass fucking gape anal hole ass puss...
Sissy Femboy Opens her Ass for the Fucking Machine 3:34
Sissy Femboy Opens her Ass for the Fucking Machine
Lisa Controls my Electro Stim Chastity Cage and Dildo Fucks my Ass 15:01
Lisa Controls my Electro Stim Chastity Cage and Dildo Fucks my Ass
Frankie ASMR anal fisting slow ride monster dildo 19:52
Frankie ASMR anal fisting slow ride monster dildo
chubby trans sex slave in chastity allowed to peg her mistress 13:53
chubby trans sex slave in chastity allowed to peg her mistress
Sissy fucked by big cock 9:21
Sissy fucked by big cock
Sissy Patricia taking hawt shower 16:21
Sissy Patricia taking hawt shower
Porcelain Skinned Crossdresser Gets Pounded by BBC 6:05
Porcelain Skinned Crossdresser Gets Pounded by BBC
Beautiful caged sissy fuck her ass 3:26
Beautiful caged sissy fuck her ass
Caged Ass Training Sissy Bimbo Brandynette Lovense Hush 45mm Anal Plug 19:05
Caged Ass Training Sissy Bimbo Brandynette Lovense Hush 45mm Anal Plug
BBC Vibrator Sissy Training 11:50
BBC Vibrator Sissy Training
Squeezing a penis into a micro cage 11:40
Squeezing a penis into a micro cage
Slutty Trans Bunny Lilith Eclipse Fucks Herself With Carrots In Chastity Ass To Mouth 12:24
Slutty Trans Bunny Lilith Eclipse Fucks Herself With Carrots In Chastity Ass To Mouth
Sitting on my trans girlfriend's face until I come while she's locked in inescapable chastity 11:08
Sitting on my trans girlfriend's face until I come while she's locked in inescapab...
30 minutes no break deepthroat spitroast challenge! 29:51
30 minutes no break deepthroat spitroast challenge!
Ladyboy girlfriend bonks and gapes her booty with massive monster cock 8:08
Ladyboy girlfriend bonks and gapes her booty with massive monster cock
Moon Cosplay Extreme Anal 10:17
Moon Cosplay Extreme Anal
Chastity device Big black anal 22:34
Chastity device Big black anal
When I was walking naked, a police car passed by. 10:01
When I was walking naked, a police car passed by.
[SISSY]I masturbated in a public restroom with a dildo and Artificial vagina. 17:21
[SISSY]I masturbated in a public restroom with a dildo and Artificial vagina.
hawt cd millie cums hands free in chastity whilst riding sex tool 0:55
hawt cd millie cums hands free in chastity whilst riding sex tool
Trans Girl Puts on Chastity Cage and Plays with Big Toys! 24:33
Trans Girl Puts on Chastity Cage and Plays with Big Toys!
[SISSY] I laid ping pong balls and eggs in the park during the day. 8:42
[SISSY] I laid ping pong balls and eggs in the park during the day.
Chastity Femboy Rides a Dildo After Week of Denial 8:56
Chastity Femboy Rides a Dildo After Week of Denial
trans slut fucking her ass deep and gaping 16:47
trans slut fucking her ass deep and gaping
Sissy got some serious anal pounding with Easter Eggs!! (part 2) 8:02
Sissy got some serious anal pounding with Easter Eggs!! (part 2)
femboi sloppy and hard anal ride with dildo 4k 60fps 8:20
femboi sloppy and hard anal ride with dildo 4k 60fps
Caged Trap Riding Sextoy and Vibrating Cage to Agonorgasmos 4K 15:07
Caged Trap Riding Sextoy and Vibrating Cage to Agonorgasmos 4K
Tight manhole filled with Chastity Michaels shecock 6:12
Tight manhole filled with Chastity Michaels shecock
Sissy cums in cage to being degraded as Mistresss trash recycling pig angel Scarlett black 11:56
Sissy cums in cage to being degraded as Mistresss trash recycling pig angel Scarle...
Femboy in Chastity Solo 10:09
Femboy in Chastity Solo
sissy bonks herself with a marital-device in a chastity strap using her cum as a lubricant 11:40
sissy bonks herself with a marital-device in a chastity strap using her cum as a l...
Caged Sissy Drink Her Cum From Condom Watching a Porn Movie 6:07
Caged Sissy Drink Her Cum From Condom Watching a Porn Movie
Sissy Boi Enjoys New Titties 10:09
Sissy Boi Enjoys New Titties
Sissygasm Defiance Day 1 - Sissy Trap Chap Rides Sex Tool 23:43
Sissygasm Defiance Day 1 - Sissy Trap Chap Rides Sex Tool
Dressed up sissy taking a pounding locked in chastity 1:38
Dressed up sissy taking a pounding locked in chastity
SISSY LATEXDOLL MASTURBATION #1 12:12
SISSY LATEXDOLL MASTURBATION #1
Naughty sissy in chastity plays with buttplug and bouncing on dildo 6:22
Naughty sissy in chastity plays with buttplug and bouncing on dildo
Crossdresser in Chastity Gets Dressed and Dildo Fucked 20:51
Crossdresser in Chastity Gets Dressed and Dildo Fucked
Cynthia shemale chastity fuck suck and dildo 15:24
Cynthia shemale chastity fuck suck and dildo
sissy in chastity pounds pussy hard until she makes cummies 20:39
sissy in chastity pounds pussy hard until she makes cummies
Caged Trap Pumping herself 4K 16:09
Caged Trap Pumping herself 4K
Showcasing my butt-plugs! 6:45
Showcasing my butt-plugs!
Anal vibrator tranny slut chastity 7:04
Anal vibrator tranny slut chastity
Ride on Big Dildo and Tease Chastity 1:07
Ride on Big Dildo and Tease Chastity
[SISSY] I played with exposure on the bridge at night. 6:29
[SISSY] I played with exposure on the bridge at night.
SisK lock up her juicy clitty and play with her anus 7:31
SisK lock up her juicy clitty and play with her anus
Rainbow Kitty Scarlet Sky Squirts Girl Cum! 6:53
Rainbow Kitty Scarlet Sky Squirts Girl Cum!