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Search » Sissy Training Videos » (149)

Training Maid – worshipping mistress’ feet
35:24
2021-06-03 00:00:00
Training Maid – worshipping mistress’ feet
Feet,
AliceInBondageLand - Sissy Spring Blossom Foursome Part
14:59
2022-10-04 00:00:00
AliceInBondageLand - Sissy Spring Blossom Foursome Part
A Mrs Loving Movie With Ms Simone and Sissy Allyson 2
10:14
2016-10-06 00:00:00
A Mrs Loving Movie With Ms Simone and Sissy Allyson 2
Training My Hot Sissy Bitch How To Deep Throat Huge Cocks Ramming It Down Her Throat Gagging Her
4:25
2021-12-25 00:00:00
Training My Hot Sissy Bitch How To Deep Throat Huge Cocks Ramming It Down Her Throat Gagging Her
Bitch, Cock, Gagging,
Cuckolds secrets – 3 BBC bulls and sissy husband fuck his wife
12:52
2021-09-26 00:00:00
Cuckolds secrets – 3 BBC bulls and sissy husband fuck his wife
Fuck, Husband, Wife,
Wife Cuckolds Cum Eating Sissy Husband
6:32
2022-02-05 00:00:00
Wife Cuckolds Cum Eating Sissy Husband
Cumshot, Husband, Wife,
Granny training deepthroat and swallows
10:09
2021-08-18 00:00:00
Granny training deepthroat and swallows
Deepthroat, Granny,
Training aged asian girl toying with my schlong
3:27
2018-09-05 00:00:00
Training aged asian girl toying with my schlong
Asian,


Do you wanna be a sissy? First time in your life? Ok, that's video for you! FemDom POV sissification
6:30
2021-05-28 00:00:00
Do you wanna be a sissy? First time in your life? Ok, that's video for you! FemDom POV sissification
Femdom, POV,
Anastasia Mistress strapon rough sissy slave femdom
6:07
2022-08-20 00:00:00
Anastasia Mistress strapon rough sissy slave femdom
Femdom, Strapon,
Interracial cuckold sissy creampie eating hot wife sucks and fucks bbc while husband watches wife
1:18
2022-02-08 00:00:00
Interracial cuckold sissy creampie eating hot wife sucks and fucks bbc while husband watches wife
Creampie, Cuckold, Husband, Interracial,
Egyptian Wife With Indian Sissy
1:24
2022-07-10 00:00:00
Egyptian Wife With Indian Sissy
Egyptian, Indian, Wife,
Cuckolds’ secrets – 3 BBC bulls fucking sissy’s wife
22:23
2021-10-13 00:00:00
Cuckolds’ secrets – 3 BBC bulls fucking sissy’s wife
Wife,
Insatiable step-mother training her some sapphic abilities
6:12
2022-12-16 00:00:00
Insatiable step-mother training her some sapphic abilities
Mom,
Sissy locked in KTB chastity
11:20
2021-08-19 00:00:00
Sissy locked in KTB chastity
Double fisting training for rough Crazywifeslut
1:42
2021-09-18 00:00:00
Double fisting training for rough Crazywifeslut
Double, Fisting,
'4 hot wives cuckold their husbands and make them watch them suck and fuck big cocks while locked in chastity and sissy femdom'
2:59
2021-09-20 00:00:00
'4 hot wives cuckold their husbands and make them watch them suck and fuck big cocks while locked in chastity and sissy femdom'
Cock, Cuckold, Fuck, Suck,
Busty fisting domina fists sissy asshole in BDSM lesson
5:00
2024-02-15 04:03:16
Busty fisting domina fists sissy asshole in BDSM lesson
Time for Your Daily Pounding - Pegging Training
3:42
2021-10-01 00:00:00
Time for Your Daily Pounding - Pegging Training
Sissy locked in KTB chastity
11:20
2021-08-19 00:00:00
Sissy locked in KTB chastity
sissy
16:02
2021-11-08 00:00:00
sissy
Sissy Husband Masturbates in Girl's arms
5:43
2021-12-30 00:00:00
Sissy Husband Masturbates in Girl's arms
'Do you wanna be a sissy? First time in your life? Ok, that's video for you! FemDom POV sissification'
6:30
2022-07-11 00:00:00
'Do you wanna be a sissy? First time in your life? Ok, that's video for you! FemDom POV sissification'
Femdom, POV,
'DP and Anal squirt training pt2'
3:14
2022-12-23 00:00:00
'DP and Anal squirt training pt2'
'SUB BABY SLUT IN TRAINING, GOLDEN "HAIR" SHOWER'
8:36
2022-01-08 00:00:00
'SUB BABY SLUT IN TRAINING, GOLDEN "HAIR" SHOWER'
'Curious Nymphet blonde wife natural tits anal masturbation handjob sissy husband fucking hairy pussy'
5:13
2022-03-29 00:00:00
'Curious Nymphet blonde wife natural tits anal masturbation handjob sissy husband fucking hairy pussy'
'Femdom Mistress giving sissy anal lessons'
16:19
2022-01-18 00:00:00
'Femdom Mistress giving sissy anal lessons'
Cheating Archive COUGAR in tights and BIG BLACK COCK Sissy Spouse gauze
14:31
2023-07-02 00:00:00
Cheating Archive COUGAR in tights and BIG BLACK COCK Sissy Spouse gauze

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'Anal Slave Training (short) تدريب الرقيق الشرج'
0:32
2022-12-22 00:00:00
'Anal Slave Training (short) تدريب الرقيق الشرج'
'Karina Valentina Homemade Anal Training and Facial with Daddy'
21:38
2022-11-02 00:00:00
'Karina Valentina Homemade Anal Training and Facial with Daddy'
sissy get spanking
0:23
2022-05-17 00:00:00
sissy get spanking
Big Ass Sissy Slut Cumming No Hands Like a Girl - the Tranny MILF
5:44
2024-11-14 12:15:06
Big Ass Sissy Slut Cumming No Hands Like a Girl - the Tranny MILF
Anal, Big Ass, Cumshot, Masturbation,
Athletic Lesbian Wife Cock Training To Fuck
8:08
2016-10-11 00:00:00
Athletic Lesbian Wife Cock Training To Fuck
'Angry mistress fuck the sissy with the huge dildo and she cums and screams like a bitch Femdom'
7:12
2021-06-24 00:00:00
'Angry mistress fuck the sissy with the huge dildo and she cums and screams like a bitch Femdom'
'Creampie eating compilation of hot wives cuckolding their sissy husbands who watch them get fucked and suck out creampies'
2:29
2022-01-18 00:00:00
'Creampie eating compilation of hot wives cuckolding their sissy husbands who watch them get fucked and suck out creampies'
Sissy Tammy and Dildo For Mistress Andrea
6:05
2016-07-03 00:00:00
Sissy Tammy and Dildo For Mistress Andrea
MissionaryBoys - The Rulebreaker: Elder Shell's Obedience Training
17:05
2024-11-02 11:06:14
MissionaryBoys - The Rulebreaker: Elder Shell's Obedience Training
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Expert Step Mothers With Humungous Cupcakes Training Their Stepsons A Lesson How To Please A Nymph
15:10
2022-12-16 00:00:00
Expert Step Mothers With Humungous Cupcakes Training Their Stepsons A Lesson How To Please A Nymph
Massive Penis ToyBoy Gets Hump Education From Molten COUGAR Sissy Neri
10:45
2022-12-16 00:00:00
Massive Penis ToyBoy Gets Hump Education From Molten COUGAR Sissy Neri
Lesbian sex training with Tiffany and Sybil
12:00
2021-11-30 00:00:00
Lesbian sex training with Tiffany and Sybil
CD Sissy blows Huge BBC with Facial Fiona Fortune Blowjob Amateur Crossdresser Monster Cock
6:13
2025-01-11 16:47:13
CD Sissy blows Huge BBC with Facial Fiona Fortune Blowjob Amateur Crossdresser Monster Cock
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The Training Of With Laura Tithapia
9:49
2024-12-04 00:39:05
The Training Of With Laura Tithapia
Big Tits, Boobs, Brunette, Busty,
Sissy Slut Takes a Bath in White Lingerie Before Going to Bed
8:12
2024-10-16 21:48:17
Sissy Slut Takes a Bath in White Lingerie Before Going to Bed
Amateur, Bathroom, Cumshot, Homemade,
Busty Stepmom Makes Her Stepson Dick Her And Her Sissy Down
9:52
2023-10-18 21:40:16
Busty Stepmom Makes Her Stepson Dick Her And Her Sissy Down
Sissy boy fingering
10:25
2025-02-21 21:05:22
Sissy boy fingering
Amateur, Anal, Cuckold, Fingering,
I'm going to start training you now
12:36
2025-02-19 20:15:10
I'm going to start training you now
Amateur, Asian, BDSM, Big Boobs,
Anal Training With Lindseylove
12:24
2025-02-04 05:02:21
Anal Training With Lindseylove
Anal, Brunette, Couple, MILF,
Anal training with wife
10:36
2025-02-16 20:36:26
Anal training with wife
Amateur, Anal, Couple, Homemade,
Anal Slut Training Ass To Mouth Teen Anal Creampie Pov
16:35
2025-02-10 03:24:28
Anal Slut Training Ass To Mouth Teen Anal Creampie Pov
Anal, Ass, Brunette, Couple,
Anal Slut Training Ass To Mouth Teen Anal Creampie Pov
16:35
2025-02-11 05:38:21
Anal Slut Training Ass To Mouth Teen Anal Creampie Pov
Anal, Ass, Brunette, Couple,
Anal Training With Lindseylove
12:24
2025-02-04 02:52:20
Anal Training With Lindseylove
Anal, Brunette, Couple, MILF,
Imagine me training like this naked in front of you, love
14:17
2025-01-08 17:25:13
Imagine me training like this naked in front of you, love
Amateur, Big Ass, Big Tits, Brunette,
Lindseylove Slut Training
22:11
2025-02-21 04:20:33
Lindseylove Slut Training
Brunette, Couple, MILF, Pornstar,
Sissy Whore Training POV
4:30
2025-01-31 14:38:27
Sissy Whore Training POV
Amateur, Blonde, Fetish, Foot,
Double Anal Training in Indian Ass
5:08
2025-02-18 20:45:07
Double Anal Training in Indian Ass
Amateur, Anal, Asian, Ass,
I Bang The Horny Woman During Training 10 Min
9:36
2024-12-14 10:06:16
I Bang The Horny Woman During Training 10 Min
Big Cock, Black, Brunette, Cock,
Cuckold MILF - Sissy husband watching hos bride with BBC
12:41
2025-01-21 05:36:13
Cuckold MILF - Sissy husband watching hos bride with BBC
Amateur, Bride, Cheating, Cuckold,
Goth Chubby Sissy Wearing One of Her Lingeries!
2:54
2025-02-06 19:59:15
Goth Chubby Sissy Wearing One of Her Lingeries!
Amateur, Ass, BBW, Big Ass,
Barbatus Fetish and Training Academ Fangs Pela Visita
10:46
2024-12-01 07:59:16
Barbatus Fetish and Training Academ Fangs Pela Visita
Big Boobs, Brunette, European, Fetish,
Young Athlete Loves Hard Fucking After Training.
15:04
2025-01-24 18:35:24
Young Athlete Loves Hard Fucking After Training.
Blonde, Cumshot, Doggystyle, Hardcore,
Training Zero Femdom Chained Devotion Slave BDSM Bondage Ballbusting Orgasm Cum Pussy Licking Real Homemade Amateur Wife Milf
1:40
2025-01-31 07:22:16
Training Zero Femdom Chained Devotion Slave BDSM Bondage Ballbusting Orgasm Cum Pussy Licking Real Homemade Amateur Wife Milf
Amateur, BDSM, Bondage, British,
Cuckold Archive - cuckold sissy watching redhead wife
16:20
2025-01-29 07:18:17
Cuckold Archive - cuckold sissy watching redhead wife
Amateur, Cheating, Cuckold, Fuck,
NEW sissy gets deflowered with monster DILDO
12:50
2025-01-24 18:35:24
NEW sissy gets deflowered with monster DILDO
Amateur, Anal, Croatian, Dildo,
Busty Mistress Mary train her sissy slave with dildo sucking and pegging!
5:53
2025-01-21 05:36:13
Busty Mistress Mary train her sissy slave with dildo sucking and pegging!
Anal, Ass, BDSM, Big Tits,
Sissy hot timeline
6:47
2025-02-18 20:45:07
Sissy hot timeline
Amateur, Anal, European, French,
Stepmommy Training and Catch Her Step Son Jerk on Her
8:49
2025-01-24 05:48:13
Stepmommy Training and Catch Her Step Son Jerk on Her
Amateur, Ass, BBW, Jerking,
My Mma Training With Got Us Both Worked Up - Veronica Avluv
8:00
2024-12-12 01:06:15
My Mma Training With Got Us Both Worked Up - Veronica Avluv
Brunette, Fetish, Hairy, Lesbian,
Kinky Wife Is Cuckolding Her Sissy Husband And Moaning From Pleasure During An Intense Orgasm
8:00
2024-12-24 13:40:20
Kinky Wife Is Cuckolding Her Sissy Husband And Moaning From Pleasure During An Intense Orgasm
Asian, Big Tits, Boobs, Busty,
Trying My New Large Vibrating Buttplug for Anal Training – Leads to Massive Creampie with My Husband
8:46
2024-12-30 16:45:12
Trying My New Large Vibrating Buttplug for Anal Training – Leads to Massive Creampie with My Husband
Amateur, Anal, Babes, Big Ass,
Masterbating on lunch during training!
7:10
2024-12-18 15:41:12
Masterbating on lunch during training!
Amateur, Babes, Big Ass, Big Boobs,
Sissy Maid Slut Humiliated by 2 Hotwifes and BBC
34:14
2025-02-03 19:35:23
Sissy Maid Slut Humiliated by 2 Hotwifes and BBC
Big Cock, Black, Booty, British,
Slut Training 10 Min With Lily Thot And Richard Mann
10:00
2025-01-07 14:36:16
Slut Training 10 Min With Lily Thot And Richard Mann
Ass, Big Cock, Black, Brunette,
Cougar Training With Ricky Johnson, Tana Lea - Brazzers
1:09
2024-11-16 07:59:17
Cougar Training With Ricky Johnson, Tana Lea - Brazzers
Big Tits, Cumshot, Facials, Gagging,
Riding on Hard Dick Is Part of Training! She Gets Inside Pussy Stretching
14:54
2025-02-11 08:13:15
Riding on Hard Dick Is Part of Training! She Gets Inside Pussy Stretching
Amateur, Big Ass, Big Dick, Blowjobs,
Angie Bloom - Slut Training Angie Bloom
10:10
2024-09-10 06:50:07
Angie Bloom - Slut Training Angie Bloom
Anal Plug & Ass Play: My Ass Training Adventure.
2:19
2024-12-11 14:18:11
Anal Plug & Ass Play: My Ass Training Adventure.
Amateur, Anal, Ass, Butt,
Big ass Femboy Sissy in pantyhose teasing
0:37
2025-01-15 18:00:18
Big ass Femboy Sissy in pantyhose teasing
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Plugged Ass for Pleasure: A Daily Anal Training Ritual
1:07
2024-12-29 03:53:11
Plugged Ass for Pleasure: A Daily Anal Training Ritual
Amateur, Anal, Ass, Butt,
Bathroom Butt Plug - Daily Anal Training
1:09
2025-01-20 17:33:10
Bathroom Butt Plug - Daily Anal Training
Amateur, Anal, Ass, Bathroom,
Getting deeper with my 12 inch toy after a training session.
21:48
2024-11-21 00:44:09
Getting deeper with my 12 inch toy after a training session.
Amateur, Anal, British, Dildo,
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