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Search » Sissy Jail Videos » (136)

Worthless sissy man can&#039_t satiate Micky Lynn
Worthless sissy man can&#039_t satiate Micky Lynn
2018-10-15 00:00:00
xVideos
7:00
Wife met him via letter wile he was in jail
Wife met him via letter wile he was in jail
2021-06-14 00:00:00
xHamster
2:45
Mistress Milks Her Slaves Dick Very Hot! - Sissy Slut And Dick Hot
Mistress Milks Her Slaves Dick Very Hot! - Sissy Slut And Dick Hot
2025-01-07 10:25:11
HClips
5:59
Riley brought from court to jail
Riley brought from court to jail
2018-08-21 00:00:00
PornHub
10:25
Arab Cuckold Sissy Anal Sex
Arab Cuckold Sissy Anal Sex
2022-06-27 00:00:00
xHamster
1:19
Cuckold Archive, Thick Arab Sissy sucks and fucks wife
Cuckold Archive, Thick Arab Sissy sucks and fucks wife
2020-09-05 00:00:00
xHamster
13:16
Breastfeeding My Sissy Babe While Naked Getting Her Full Before Having Her Fuck Me
Breastfeeding My Sissy Babe While Naked Getting Her Full Before Having Her Fuck Me
2022-01-20 00:00:00
PornHub
1:33
Hot Cop DP Fucked Buy Monster cock inmates Through Jail Cell Grill
Hot Cop DP Fucked Buy Monster cock inmates Through Jail Cell Grill
2022-09-06 00:00:00
PornHub
2:47
Mature Mistress dominates sissy
Mature Mistress dominates sissy
2020-09-03 00:00:00
xHamster
25:31
SECRETARY IN NYLON FUCK SISSY BOSS WITH STRAPON IN WOMEN THONGS, CHASTITY BELT, PANTYHOSE AND HEELS
SECRETARY IN NYLON FUCK SISSY BOSS WITH STRAPON IN WOMEN THONGS, CHASTITY BELT, PANTYHOSE AND HEELS
2022-02-19 00:00:00
PornHub
3:18
Domme BBWPrincessMary turns hotwife bf into her sissy boi mega-bitch
Domme BBWPrincessMary turns hotwife bf into her sissy boi mega-bitch
2018-11-01 00:00:00
PornHub
9:39
Recording My Wife Sucking A Smooth Sissy Cute Clit Taking It All In Her Mouth
Recording My Wife Sucking A Smooth Sissy Cute Clit Taking It All In Her Mouth
2021-12-01 00:00:00
PornHub
2:30
Sexy Bbw Spanking tight Sissy Ass
Sexy Bbw Spanking tight Sissy Ass
2022-10-07 00:00:00
PornHub
12:48
Pregnant wife fisting also strapon pegging sissy husband
Pregnant wife fisting also strapon pegging sissy husband
2021-08-26 00:00:00
SunPorno
16:24
SWOLLEN SISSY BITCH
SWOLLEN SISSY BITCH
2022-07-12 00:00:00
PornHub
0:35
MILF Self Sucking Cock While Sissy Training Maxine Cayenne
MILF Self Sucking Cock While Sissy Training Maxine Cayenne
2021-12-22 00:00:00
PornHub
1:14
My finer Half: A Sissy Caption story
My finer Half: A Sissy Caption story
2018-12-29 00:00:00
PornHub
11:46
Nasty step-mother plows Her son-in-law After Getting Him Out Of jail
Nasty step-mother plows Her son-in-law After Getting Him Out Of jail
2019-09-30 00:00:00
xVideos
8:02
Prostate Cock Milking For Hot And Horny Sissy Twink
Prostate Cock Milking For Hot And Horny Sissy Twink
2024-01-29 04:03:16
HClips
5:59
SL Home Alone Sissy Get Hard Anal Fuck From Daddy
SL Home Alone Sissy Get Hard Anal Fuck From Daddy
2024-12-28 07:30:11
xHamster
6:29
Hotwife Fucks Sissy With 2 dildo's befor she fists her ass
Hotwife Fucks Sissy With 2 dildo's befor she fists her ass
2022-09-20 00:00:00
PornHub
14:16
Bound and gagged Japanese hottie has her tender mouth fucked by Asian Whores in Jail
Bound and gagged Japanese hottie has her tender mouth fucked by Asian Whores in Jail
2023-12-09 16:20:21
TXXX
6:00
Sissy is dripping on my foot 💦
Sissy is dripping on my foot 💦
2022-12-13 00:00:00
PornHub
8:54
Crossdresser sissy pegged by group of CFNM busty dominas
Crossdresser sissy pegged by group of CFNM busty dominas
2023-02-20 00:00:00
HotMovs
6:10
Wife pegging sissy slut husband and give him ass gape
Wife pegging sissy slut husband and give him ass gape
2022-06-20 00:00:00
PornHub
2:11
'Best Of Harmony Rose vol 7 Cuckolds her Sissy Husbands who eat Creampies hot Slut Wife Strapon Domination Sex blowjob femdom'
'Best Of Harmony Rose vol 7 Cuckolds her Sissy Husbands who eat Creampies hot Slut Wife Strapon Domination Sex blowjob femdom'
2022-04-12 00:00:00
RedTube
2:13
'Creampie eating compilation of hot wives cuckolding their sissy husbands who watch them get fucked and suck out creampies'
'Creampie eating compilation of hot wives cuckolding their sissy husbands who watch them get fucked and suck out creampies'
2022-01-17 00:00:00
RedTube
2:29
Anastasia Mistress strap on her guy sissy slave anal toy female domination
Anastasia Mistress strap on her guy sissy slave anal toy female domination
2023-04-06 00:00:00
PornHub
6:47
Freaky she-male SISSY grubby GARDENBOY NETSTOCKINGS faggot rectal
Freaky she-male SISSY grubby GARDENBOY NETSTOCKINGS faggot rectal
2019-04-21 00:00:00
PornHub
2:40
Sissy boyfriend fucked in front of your girlfriend
Sissy boyfriend fucked in front of your girlfriend
2023-09-16 00:00:00
PornHub
1:19
'Hot wife Harmony Rose in femdom cuckold creampie eating sissy chastity keyholding sph sex while husband watches face sitting'
'Hot wife Harmony Rose in femdom cuckold creampie eating sissy chastity keyholding sph sex while husband watches face sitting'
2021-05-29 00:00:00
RedTube
1:39
Me Emma handjob masturbation sissy training crossdresser amateur
Me Emma handjob masturbation sissy training crossdresser amateur
2022-05-21 00:00:00
PornHub
2:12
Sissy Faggot Humilation JOI with 19 year old Kymmy Harper
Sissy Faggot Humilation JOI with 19 year old Kymmy Harper
2021-12-15 00:00:00
PornHub
4:38
Brazzers - Super Hot Doc Kira Noir Porks Her Jail Homie Patient Scott Pounds
Brazzers - Super Hot Doc Kira Noir Porks Her Jail Homie Patient Scott Pounds
2023-01-02 00:00:00
Brazzers
10:43
Kay Uber-Cute helps her hubby in jail by taking on 2 meaty lollipops
Kay Uber-Cute helps her hubby in jail by taking on 2 meaty lollipops
2023-01-02 00:00:00
Dogfart Network
8:40
Massive Penis ToyBoy Gets Hump Education From Molten COUGAR Sissy Neri
Massive Penis ToyBoy Gets Hump Education From Molten COUGAR Sissy Neri
2023-01-02 00:00:00
Mature NL
10:45
Black Priya Price luvs 3some in jail
Black Priya Price luvs 3some in jail
2023-01-02 00:00:00
Dogfart Network
10:39
Lippy asian panda domina domina for sissy fellows
Lippy asian panda domina domina for sissy fellows
2018-09-06 00:00:00
Tube8
7:35
Mistress Stellina Obscura Exposes Her Sissy Husband - Deep Throating, Pegging, Double Anal & Fisting
Mistress Stellina Obscura Exposes Her Sissy Husband - Deep Throating, Pegging, Double Anal & Fisting
2025-02-09 10:56:08
HClips
7:15
Sissy Slut - Sissy Gets Massive Facial From Bbc
Sissy Slut - Sissy Gets Massive Facial From Bbc
2025-02-12 22:58:15
HClips
7:57
I Am a Dirty Matured Sissy CD in Christmas Times
I Am a Dirty Matured Sissy CD in Christmas Times
2024-12-28 07:30:11
xHamster
3:09
my sissy ass need some dick. dildo fuckn in dress and panties (pt 2)
my sissy ass need some dick. dildo fuckn in dress and panties (pt 2)
2025-02-13 08:14:10
xHamster
16:06
2 Mature Tranny Tgirls spitroast and piss fuck their male slave, very vicious. CD Sissy play Great video from the wonderfu...
2 Mature Tranny Tgirls spitroast and piss fuck their male slave, very vicious. CD Sissy play Great video from the wonderfu...
2025-01-04 08:13:11
xVideos
15:19
Busty Jail Bird Wants A Wild Rid
Busty Jail Bird Wants A Wild Rid
2025-02-10 20:02:25
HotMovs
7:00
Fishnet Sissy 2025#02 - Riding a huge 95mm anal plug(2) -
Fishnet Sissy 2025#02 - Riding a huge 95mm anal plug(2) -
2025-02-05 20:13:16
xHamster
5:35
Sissy Stacy Shows How She Can Use BBC
Sissy Stacy Shows How She Can Use BBC
2025-02-09 08:14:08
xHamster
4:29
Kinky Wife Is Cuckolding Her Sissy Husband And Moaning From Pleasure During An Intense Orgasm
Kinky Wife Is Cuckolding Her Sissy Husband And Moaning From Pleasure During An Intense Orgasm
2024-12-24 08:00:20
TXXX
8:00
masked bbw sissy stuffs her holes with huge dildos
masked bbw sissy stuffs her holes with huge dildos
2024-12-04 06:55:05
xHamster
21:31
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