New Tranny Videos Tagged with chastity

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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...
7.6K
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Sissy Clitty Chastity Training 10:14
Sissy Clitty Chastity Training
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Chastity TS PMV 5:30
Chastity TS PMV
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Sissy in G-String and Chastity Fucked Hard 12:35
Sissy in G-String and Chastity Fucked Hard
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SISSY HYPNO - DOXY TRANSFORMATION 9:24
SISSY HYPNO - DOXY TRANSFORMATION
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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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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
24K
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Become a Shemale Sex Slave sissy training instructions 12:58
Become a Shemale Sex Slave sissy training instructions
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Kymmy has 1st Sissygasam in Chastity Ever! BIGGEST EJACULATION 18:06
Kymmy has 1st Sissygasam in Chastity Ever! BIGGEST EJACULATION
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teasing trans chastity slave during locktober part 1 10:53
teasing trans chastity slave during locktober part 1
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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 ...
15K
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Sissy maid in chastity with big fake tits rides dildo 6:00
Sissy maid in chastity with big fake tits rides dildo
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Sissy Training: Deepthroat, Anal & Sissygasm while Locked in Chastity 27:23
Sissy Training: Deepthroat, Anal & Sissygasm while Locked in Chastity
12K
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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!
30K
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Sissy Fucks herself to Handsfree Sissygasm in Chastity Cage 5:05
Sissy Fucks herself to Handsfree Sissygasm in Chastity Cage
24K
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Latex Gimpette Fuck Machine Frenzy 24:07
Latex Gimpette Fuck Machine Frenzy
5.5K
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Femboy Sissy Gaping Ass and Riding Fuck Machine Hard - Sissy Jazzie 13:04
Femboy Sissy Gaping Ass and Riding Fuck Machine Hard - Sissy Jazzie
11K
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Sissy maid does dishes with a vibrating plug and chastity 2:05
Sissy maid does dishes with a vibrating plug and chastity
4.8K
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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
6.7K
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sissy dildo training 8:11
sissy dildo training
3.9K
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Sarina takes BBC in Perfect Total Sub Form 5:39
Sarina takes BBC in Perfect Total Sub Form
6.8K
100%
Natalie Mars and Charlotte Sartre Anal Play 12:10
Natalie Mars and Charlotte Sartre Anal Play
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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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Sissy Lucy being locked in metal Chastity for Locktober 19:00
Sissy Lucy being locked in metal Chastity for Locktober
7.2K
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"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...
2.8K
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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 ...
14K
66%
Sergeant  caught Cheating W/ Slut Natalie Mars by Jasmeen LeFleur 30:44
Sergeant  caught Cheating W/ Slut Natalie Mars by Jasmeen LeFleur
9.8K
80%
Goddess in chastity fists her perfect ass to orgasm 8:49
Goddess in chastity fists her perfect ass to orgasm
6.0K
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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...
1.2K
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Sissy Crossdresser Chastity BBC Sex Tool 9:43
Sissy Crossdresser Chastity BBC Sex Tool
1.2K
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Sissygasm - Cageful of Cum 11:29
Sissygasm - Cageful of Cum
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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...
4.0K
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Soft Femboy Anal Play & Pee Ending 9:55
Soft Femboy Anal Play & Pee Ending
4.1K
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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
2.4K
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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
4.3K
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Muzzled and Locked Transgirl Strapped by Goth Femdom 12:02
Muzzled and Locked Transgirl Strapped by Goth Femdom
2.1K
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Sissy slut gapes ass with thick dildo and fuck machine 12:23
Sissy slut gapes ass with thick dildo and fuck machine
2.1K
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Cute femboy locked in chastity have sissygasm 11:25
Cute femboy locked in chastity have sissygasm
999
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TRANS SQUIRTING AND CUM COMPILATION!!! 14:05
TRANS SQUIRTING AND CUM COMPILATION!!!
1.2K
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Caged Orgasm for Femboy Rammed by Fucking Machine 10:00
Caged Orgasm for Femboy Rammed by Fucking Machine
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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
3.8K
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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
5.6K
81%
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
2.3K
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Squeezing a penis into a micro cage 11:40
Squeezing a penis into a micro cage
1.2K
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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
1.7K
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Sissy Bitch Rides Sex-Toy In Chastity 11:37
Sissy Bitch Rides Sex-Toy In Chastity
861
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Transgirl is Spit Roasted by her Girlfriend and Fucking Machine 29:59
Transgirl is Spit Roasted by her Girlfriend and Fucking Machine
286K
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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 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...
3.0K
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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...
7.7K
85%
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!
1.8K
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Caged & Plugged Sissy in Selfbondage Straitjacket and a Harley Quinn Wig 31:30
Caged & Plugged Sissy in Selfbondage Straitjacket and a Harley Quinn Wig
4.6K
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Sissy Slut Fucking Machine Anal Training and Huge Toys (long Version) 19:47
Sissy Slut Fucking Machine Anal Training and Huge Toys (long Version)
5.5K
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Fuck machine cum in tiny chastity cage 7:52
Fuck machine cum in tiny chastity cage
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SissyBoy - I Don't Need a Pussy to CUM ( SissyBoy life ) 2:40
SissyBoy - I Don't Need a Pussy to CUM ( SissyBoy life )
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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 ...
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Horny Goth Crossedressing Femboy Practices with a Dildo(voiced) 15:34
Horny Goth Crossedressing Femboy Practices with a Dildo(voiced)
2.2K
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Sissy crossdresser femboy ruins her own orgasm with hardcore ballbusting 9:03
Sissy crossdresser femboy ruins her own orgasm with hardcore ballbusting
2.7K
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BBC and Horse Sex-Toy inside a Loose Femboy in Chastity 14:20
BBC and Horse Sex-Toy inside a Loose Femboy in Chastity
2.7K
100%
Caged Trap Riding Sextoy and Vibrating Cage to Agonorgasmos 4K 15:07
Caged Trap Riding Sextoy and Vibrating Cage to Agonorgasmos 4K
4.3K
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Crossdresser in Chastity Gets Dressed and Dildo Fucked 20:51
Crossdresser in Chastity Gets Dressed and Dildo Fucked
1.5K
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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...
1.3K
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Goth Tgirl with Fishnets Fucked by Black Dildo 1:12
Goth Tgirl with Fishnets Fucked by Black Dildo
1.3K
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Frankie ASMR anal fisting slow ride monster dildo 19:52
Frankie ASMR anal fisting slow ride monster dildo
3.1K
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TEEN SISSY CROSSDRESSER IN CHASITY BELT HANDSFREE ORGASM 14:35
TEEN SISSY CROSSDRESSER IN CHASITY BELT HANDSFREE ORGASM
2.1K
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Chastity Femboy Rides a Dildo After Week of Denial 8:56
Chastity Femboy Rides a Dildo After Week of Denial
2.0K
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Trap in Chastity Cage Anal 19:12
Trap in Chastity Cage Anal
6.7K
100%
Hands off Challenge - Day 27 21:36
Hands off Challenge - Day 27
1.2K
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Sissy Mara Jade's Sissygasms! (Entire Chastity Compilation!) 10:08
Sissy Mara Jade's Sissygasms! (Entire Chastity Compilation!)
3.5K
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Sissy chastity (part 1) 9:28
Sissy chastity (part 1)
2.0K
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legal age teenager femboy edges + cums with marital-device in chastity cage 17:37
legal age teenager femboy edges + cums with marital-device in chastity cage
487
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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
4.1K
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Trying the knot and the fist and fail 21:23
Trying the knot and the fist and fail
1.1K
100%
Sissy Patricia taking hawt shower 16:21
Sissy Patricia taking hawt shower
534
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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
524
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naked slave pig exposed handcuffed nipple clamps dirty body writing in penis cage BDSM CBT 3:33
naked slave pig exposed handcuffed nipple clamps dirty body writing in penis cage ...
23
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Crossdresser Nun Astrid Apathy Sissygasms in Chastity 11:06
Crossdresser Nun Astrid Apathy Sissygasms in Chastity
3.7K
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[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.
1.8K
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Sissy in chastity pounding creampie fuckmachine 15:16
Sissy in chastity pounding creampie fuckmachine
3.0K
100%
[SISSY] I masturbated and ejaculated in a public toilet at night. 13:14
[SISSY] I masturbated and ejaculated in a public toilet at night.
2.0K
75%
Sissy Femboy Opens her Ass for the Fucking Machine 3:34
Sissy Femboy Opens her Ass for the Fucking Machine
1.2K
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When I was walking naked, a police car passed by. 10:01
When I was walking naked, a police car passed by.
1.3K
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[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.
1.1K
100%
[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.
2.6K
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Trans Girl Puts on Chastity Cage and Plays with Big Toys! 24:33
Trans Girl Puts on Chastity Cage and Plays with Big Toys!
5.7K
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Locked up unicorn in chastity performs for mistress 1:51
Locked up unicorn in chastity performs for mistress
2.1K
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submissive trap riding a black cock 12:20
submissive trap riding a black cock
2.0K
100%
Jerk off & hurt your virgin balls, sissy, to the BNWO & white extinction angel scarlett black 15:14
Jerk off & hurt your virgin balls, sissy, to the BNWO & white extinction angel sca...
1.4K
100%
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
1.8K
100%
Tight manhole filled with Chastity Michaels shecock 6:12
Tight manhole filled with Chastity Michaels shecock
159K
98%
Sissy Femboy Teases his Penis in Chastity with Vibrator 2:05
Sissy Femboy Teases his Penis in Chastity with Vibrator
3.3K
66%
Femboy in Chastity Solo 10:09
Femboy in Chastity Solo
1.2K
100%
Rainbow Kitty Scarlet Sky Squirts Girl Cum! 6:53
Rainbow Kitty Scarlet Sky Squirts Girl Cum!
1.0K
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Sissy Trap Blows her Fake Penis than Bonks it (Full Episode) 17:00
Sissy Trap Blows her Fake Penis than Bonks it (Full Episode)
2.0K
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Showcasing my butt-plugs! 6:45
Showcasing my butt-plugs!
1.3K
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Sissy locked in chastity taking Mr. Hankey Tubesteak 0:50
Sissy locked in chastity taking Mr. Hankey Tubesteak
1.5K
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Sissy Jazzie has her first sissygasm , plays with lollipops in her ass, anal gapes 11:27
Sissy Jazzie has her first sissygasm , plays with lollipops in her ass, anal gapes
1.6K
100%
chubby trans sex slave in chastity allowed to peg her mistress 13:53
chubby trans sex slave in chastity allowed to peg her mistress
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BDSM mistress plays with her sissy girl 11:37
BDSM mistress plays with her sissy girl
1.6K
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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
1.2K
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Sissy Sophie Banging Her Marital-Device Like a Bitch (Compilation) 10:50
Sissy Sophie Banging Her Marital-Device Like a Bitch (Compilation)
778
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BBC Vibrator Sissy Training 11:50
BBC Vibrator Sissy Training
521
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Vergil XL is so large ! 17:10
Vergil XL is so large !
145
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Sissy Femboy acquire Screwed 18:08
Sissy Femboy acquire Screwed
6.6K
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Sissy eats goddess out 6:21
Sissy eats goddess out
1.4K
100%
EZZYFOREVER RUINED ANAL ORGASM 16:07
EZZYFOREVER RUINED ANAL ORGASM
1.3K
100%
Getting naked and change my cloth on a hiking trail 8:49
Getting naked and change my cloth on a hiking trail
797
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Femboy sissy fucks dildo cums and eats it 13:43
Femboy sissy fucks dildo cums and eats it
1.7K
100%
virtual bj for raven 10:06
virtual bj for raven
379
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Ladyboy girlfriend bonks and gapes her booty with massive monster cock 8:08
Ladyboy girlfriend bonks and gapes her booty with massive monster cock
819
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Anal vibrator tranny slut chastity 7:04
Anal vibrator tranny slut chastity
1.9K
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[SISSY] I played with exposure on the bridge at night. 6:29
[SISSY] I played with exposure on the bridge at night.
1.7K
100%
Little Clit Sissy Boi Trains BBC Dildo For His Mistress! 3:08
Little Clit Sissy Boi Trains BBC Dildo For His Mistress!
1.1K
100%
locked femboy desperately tries to cum...and fails 10:44
locked femboy desperately tries to cum...and fails
600
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Caged Trap Pumping herself 4K 16:09
Caged Trap Pumping herself 4K
3.0K
100%
Caged Rock Trap Takes YOU to a Intimate Room and Rides u to SISSYGASM 4K 9:32
Caged Rock Trap Takes YOU to a Intimate Room and Rides u to SISSYGASM 4K
1.9K
100%
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...
1.1K
100%
your a fucking loser an embarrassing sissy angel scarlett black 11:12
your a fucking loser an embarrassing sissy angel scarlett black
858
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Cynthia shemale chastity fuck suck and dildo 15:24
Cynthia shemale chastity fuck suck and dildo
1.5K
100%
trans slut fucking her ass deep and gaping 16:47
trans slut fucking her ass deep and gaping
1.3K
100%