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Most Relevant
Linzy19's Guide To Chastity 51:23
Linzy19's Guide To Chastity
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Sissy Francesca anal play in chastity 14:26
Sissy Francesca anal play in chastity
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Sissy Piggy playing with her dildos in chastity 12:06
Sissy Piggy playing with her dildos in chastity
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Chastity TS PMV 5:30
Chastity TS PMV
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Slut Playing In Chastity And Exposing Her Hard Clit Afterwards 8:03
Slut Playing In Chastity And Exposing Her Hard Clit Afterwards
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Tight manhole filled with Chastity Michaels shecock 6:12
Tight manhole filled with Chastity Michaels shecock
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Dildo ride in chastity sissygasm 10:44
Dildo ride in chastity sissygasm
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Anal sex with sissymaid Kitsy in chastity and bunny ears 8:10
Anal sex with sissymaid Kitsy in chastity and bunny ears
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Astrid Apathy Night Time Public Display in Chastity 23:12
Astrid Apathy Night Time Public Display in Chastity
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Sissy Baby Doll, Chastity, Fills Hole and is Humiliated 16:00
Sissy Baby Doll, Chastity, Fills Hole and is Humiliated
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Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded 19:27
Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded
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Sasha's Dollhouse - Christmas Chastity and Dildo Ass Play 8:44
Sasha's Dollhouse - Christmas Chastity and Dildo Ass Play
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Sissy chastity training with big black dildo 9:18
Sissy chastity training with big black dildo
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Ilandis in a chastity thong has joy with her backdoor, masturbates with an artificial penis 11:07
Ilandis in a chastity thong has joy with her backdoor, masturbates with an artific...
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Sissy Maid Cuffed Spread Eagle in Steel Chastity Belt and Huge Dildo 20:12
Sissy Maid Cuffed Spread Eagle in Steel Chastity Belt and Huge Dildo
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sissy life in chastity 10:23
sissy life in chastity
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Soundling a locked Sissy Clit in chastity through Urethral Plug 13:35
Soundling a locked Sissy Clit in chastity through Urethral Plug
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Dawn Rides Black Destroyer in Flat Plate Chastity 8:49
Dawn Rides Black Destroyer in Flat Plate Chastity
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Davine toying deep in Latex and Chastity 16:42
Davine toying deep in Latex and Chastity
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Latex sissy maid Candy fucked by a fucking machine in chastity while playing with her dildos 11:17
Latex sissy maid Candy fucked by a fucking machine in chastity while playing with ...
1.1K
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Theresa Si training her bubble butt this time her ass plugged n clit locked, with a big steel plug and in chastity part2 15:28
Theresa Si training her bubble butt this time her ass plugged n clit locked, with ...
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I'm Too Big For My Chastity Cage 7:26
I'm Too Big For My Chastity Cage
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Dog leash & chastity 14:34
Dog leash & chastity
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Cumming twice in a Row in a Chastity Belt 6:41
Cumming twice in a Row in a Chastity Belt
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Sissy chastity (part 1) 9:28
Sissy chastity (part 1)
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Sissy maid in chastity 4:22
Sissy maid in chastity
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Femboy in Chastity Solo 10:09
Femboy in Chastity Solo
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cd millie banging in chastity pov 3:02
cd millie banging in chastity pov
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Femboy in chastity sissygasm with dildo in her ass 9:33
Femboy in chastity sissygasm with dildo in her ass
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daddy made me a new milking toy on my chastity 1:54
daddy made me a new milking toy on my chastity
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Princess in Chastity Slobbers all over Dildo 9:24
Princess in Chastity Slobbers all over Dildo
3.1K
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Sissy Bitch Rides Sex-Toy In Chastity 11:37
Sissy Bitch Rides Sex-Toy In Chastity
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Sissy joanna training in chastity 3:06
Sissy joanna training in chastity
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Riding Her Dildo In Chastity Cage 10:15
Riding Her Dildo In Chastity Cage
3.7K
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Lady-Man CHASTITY Lock Wang Tranny 9:17
Lady-Man CHASTITY Lock Wang Tranny
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Kymmy has 1st Sissygasam in Chastity Ever! BIGGEST EJACULATION 18:06
Kymmy has 1st Sissygasam in Chastity Ever! BIGGEST EJACULATION
27K
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Sissy in chastity playing with fuck machine 7:16
Sissy in chastity playing with fuck machine
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Sissy in chastity pounding creampie fuckmachine 15:16
Sissy in chastity pounding creampie fuckmachine
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Crossdressing School Girl Putting on Chastity 8:29
Crossdressing School Girl Putting on Chastity
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Pee tasting and chastity masturbation of a kinky latexdoll 15:29
Pee tasting and chastity masturbation of a kinky latexdoll
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leashed femboy in chastity plays with vibrator 13:07
leashed femboy in chastity plays with vibrator
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Sissy in Corset Rub Herself with Dildo and Rabbit, then Cum in Chastity 21:37
Sissy in Corset Rub Herself with Dildo and Rabbit, then Cum in Chastity
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Sissy Daily Basics: Some anal fun in chastity 21:30
Sissy Daily Basics: Some anal fun in chastity
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Trangirl's in Chastity Drink from her Condom in Public 9:47
Trangirl's in Chastity Drink from her Condom in Public
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Ride on dlido in Chastity 2:23
Ride on dlido in Chastity
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Sissygasm Defiance Day two - Femboy in Chastity Riding Sex Tool 21:58
Sissygasm Defiance Day two - Femboy in Chastity Riding Sex Tool
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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!
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Sissy Fucks herself to Handsfree Sissygasm in Chastity Cage 5:05
Sissy Fucks herself to Handsfree Sissygasm in Chastity Cage
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Sissy Femboy Teases his Penis in Chastity with Vibrator 2:05
Sissy Femboy Teases his Penis in Chastity with Vibrator
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Chastity Femboy Rides a Dildo After Week of Denial 8:56
Chastity Femboy Rides a Dildo After Week of Denial
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Sissy Maid Self Bondage in Spiked Chastity Cage 20:08
Sissy Maid Self Bondage in Spiked Chastity Cage
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Sissy slut Lori shows off her ass and chastity cage 8:47
Sissy slut Lori shows off her ass and chastity cage
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Multiple Prostate Orgasms in Chastity Jessica Bloom the Cum Cow 11:00
Multiple Prostate Orgasms in Chastity Jessica Bloom the Cum Cow
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Sissy Luxiana in chastity cage and fake penis 25:04
Sissy Luxiana in chastity cage and fake penis
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Cute Legal Age Teenager Cums Hard in Chastity 17:38
Cute Legal Age Teenager Cums Hard in Chastity
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Negative Chastity cum with vibrator 2:12
Negative Chastity cum with vibrator
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Cumshot on Trans Woman's Face in Bondage and Chastity 0:15
Cumshot on Trans Woman's Face in Bondage and Chastity
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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...
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Femboy in Shibari and Tiny Chastity Riding Dildo and Sissigasming 7:33
Femboy in Shibari and Tiny Chastity Riding Dildo and Sissigasming
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Naughty sissy in chastity plays with buttplug and bouncing on dildo 6:22
Naughty sissy in chastity plays with buttplug and bouncing on dildo
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tranny sissy anal chastity cage orgasm squirts 14:09
tranny sissy anal chastity cage orgasm squirts
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training her ass for big thick cocks 27:42
training her ass for big thick cocks
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sissy in chastity pounds pussy hard until she makes cummies 20:39
sissy in chastity pounds pussy hard until she makes cummies
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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...
1.9K
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Large vibrator play in chastity - pvt show/custom content 14:19
Large vibrator play in chastity - pvt show/custom content
976
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out of chastity birthday present sissy copulates sexdoll in each aperture 47:11
out of chastity birthday present sissy copulates sexdoll in each aperture
1.3K
100%
Sissy taniax with small chastity cage pounding and dildoing in her bed 10:01
Sissy taniax with small chastity cage pounding and dildoing in her bed
303
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Young BBC cums all over locked Chastity while Sammi Smith watches and gets off 12:03
Young BBC cums all over locked Chastity while Sammi Smith watches and gets off
53
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Sissy Locked in Chastity Rides Marital-Device like a Worthy Whore 8:08
Sissy Locked in Chastity Rides Marital-Device like a Worthy Whore
5.0K
66%
Sissy Maids Bed Bondage 20:49
Sissy Maids Bed Bondage
7.2K
100%
Sissy Oksana fucks her ass hard with her clit closed in chastity. sissygasm. 10:09
Sissy Oksana fucks her ass hard with her clit closed in chastity. sissygasm.
1.9K
80%
Sissy in chastity stretching on massive dick head fake penis 6:12
Sissy in chastity stretching on massive dick head fake penis
1.5K
100%
Anal Orgasms In Chastity Cage - Sissy Slut Jessica Bloom 10:14
Anal Orgasms In Chastity Cage - Sissy Slut Jessica Bloom
1.7K
100%
Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom 6:15
Sissy Guide - How to Anal Orgasm in Chastity Cage - Jessica Bloom
2.8K
100%
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
8.0K
77%
sissy cumming straight outta chastity with base ring still on ball squeeze 21:07
sissy cumming straight outta chastity with base ring still on ball squeeze
1.6K
66%
Cuckold AlexSandra eats his own cum 2:06
Cuckold AlexSandra eats his own cum
573
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Sissy Maid Spanked and Whipped in Chastity Bondage 5:25
Sissy Maid Spanked and Whipped in Chastity Bondage
4.7K
80%
Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm 7:48
Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm
1.9K
100%
Fucking Machine Anal Orgasms Chastity Foot Slut Jessica Bloom 10:09
Fucking Machine Anal Orgasms Chastity Foot Slut Jessica Bloom
496
100%
Trans Girl Ass to Mouth Masturbation in Chastity with Lots of Toys FULL VIDEO VIA ONLYFANS 8:37
Trans Girl Ass to Mouth Masturbation in Chastity with Lots of Toys FULL VIDEO VIA ...
4.3K
100%
Cute Trans Girl Spends her First Time in Chastity Cage Riding Dragon Dick 14:32
Cute Trans Girl Spends her First Time in Chastity Cage Riding Dragon Dick
8.7K
91%
Trans Girl in Chastity Lactates Milk From Her Boobs 0:30
Trans Girl in Chastity Lactates Milk From Her Boobs
414
100%
Cute pink haired trans woman masturbating in chastity 16:51
Cute pink haired trans woman masturbating in chastity
2.7K
50%
Crossdersser release from cock cage 1:23
Crossdersser release from cock cage
382
100%
Passable Sissy Deanna loves anal 1:09
Passable Sissy Deanna loves anal
1.7K
100%
Skinny sissy crossdresser with butt plug, chastity belt, armbinder and gag 11:45
Skinny sissy crossdresser with butt plug, chastity belt, armbinder and gag
18K
81%
Sissy femboy in chastity taking big dildos in her ass and trying and sissygasm 19:06
Sissy femboy in chastity taking big dildos in her ass and trying and sissygasm
10K
85%
Fetish dresser babe gurl Andreina 6:06
Fetish dresser babe gurl Andreina
1.5K
66%
Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition! 6:40
Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition!
590
0%
Cindy fucks toys hard in red 9:08
Cindy fucks toys hard in red
1.2K
100%
SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage 8:17
SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage
5.4K
91%
Sissy Maid Strappado Self Bondage 12:29
Sissy Maid Strappado Self Bondage
3.7K
66%
one of the best bitch in chastity suck a dick in public 7:31
one of the best bitch in chastity suck a dick in public
7.0K
66%
Riding a dildo and playing with my nipples 8:22
Riding a dildo and playing with my nipples
2.6K
81%
Sissy Maid Chair Self Bondage 16:18
Sissy Maid Chair Self Bondage
2.7K
50%
This Sissy whore is truly beyond return 9:59
This Sissy whore is truly beyond return
2.6K
83%
SISSY MONIQUE - Out of order 1:58
SISSY MONIQUE - Out of order
119
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SISSY MONIQUE - Sektempfang 4:06
SISSY MONIQUE - Sektempfang
208
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SisK CD in purple EP1 A tiny purple cock cage wearing 11:10
SisK CD in purple EP1 A tiny purple cock cage wearing
5.2K
89%
Straight Jacket Bondage - Sissy Maid 8:54
Straight Jacket Bondage - Sissy Maid
2.5K
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Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs. 18:52
Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ...
2.1K
60%
This Is How You Train Your Sissy Pussy (Riding Compilation) 11:34
This Is How You Train Your Sissy Pussy (Riding Compilation)
6.7K
69%
Chastity Sissys Desperate Dildo Training Captivating Caption Story 9:27
Chastity Sissys Desperate Dildo Training Captivating Caption Story
208
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The only way a sissy is allowed to have sex with a woman 7:07
The only way a sissy is allowed to have sex with a woman
306
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Sissy Sophie trains her hole against the wall 7:11
Sissy Sophie trains her hole against the wall
1.6K
100%
Ladyboy Sissy Try Fisting for First Time 6:27
Ladyboy Sissy Try Fisting for First Time
1.1K
100%
Catsuit-Bodysuit Armbinder Hogtie Self Bondage 27:10
Catsuit-Bodysuit Armbinder Hogtie Self Bondage
2.5K
50%
Real Maid Service Cleaning the kitchen Floor Sissy Mindy 4:12
Real Maid Service Cleaning the kitchen Floor Sissy Mindy
532
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Cindy take 18 inch dildo all the way in chastity 12:05
Cindy take 18 inch dildo all the way in chastity
5.4K
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Sissy Maid Self Bondage Armbinder, Anklecuffs in Balletboots 28:20
Sissy Maid Self Bondage Armbinder, Anklecuffs in Balletboots
3.5K
100%
Premature ejaculation from the penis released from the cage onto Sissy's face 1:13
Premature ejaculation from the penis released from the cage onto Sissy's face
1.4K
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Self Bondage Armbinder Hogtie in PVC Catsuit and Lycra Bodysuit with Chastity Belt and Dildo Locked in Place 19:08
Self Bondage Armbinder Hogtie in PVC Catsuit and Lycra Bodysuit with Chastity Belt...
2.8K
66%
Pegged Crossdresser Anal Anal Fucked with a Big Strapon Dildo 6:39
Pegged Crossdresser Anal Anal Fucked with a Big Strapon Dildo
2.1K
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Sissy Trap fucks her boipussy with a big dildo 5:20
Sissy Trap fucks her boipussy with a big dildo
1.2K
80%
Tiffany Kitten the sexy blonde sissy crossdresser babe shows her gorgeous body and fucks her BBC dildo 14:42
Tiffany Kitten the sexy blonde sissy crossdresser babe shows her gorgeous body and...
4.1K
75%
Sissygasm Slut Caged Training Massive Cumshots & Anal Milking Jessica Bloom 10:43
Sissygasm Slut Caged Training Massive Cumshots & Anal Milking Jessica Bloom
5.1K
90%
Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose 10:12
Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a ...
5.3K
77%
Shemale Mature in chastity playing with dildos and CUM 12:12
Shemale Mature in chastity playing with dildos and CUM
1.1K
50%
Lizzy Yum August 2022 #4 BDSM masturbation orgasm self BDSM straight jacket mermaid leggings 17:15
Lizzy Yum August 2022 #4 BDSM masturbation orgasm self BDSM straight jacket mermai...
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