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Search » Sissy Jail Videos » (286)

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
Arab Cuckold Sissy Anal Sex
Arab Cuckold Sissy Anal Sex
2022-06-27 00:00:00
xHamster
1:19
Riley brought from court to jail
Riley brought from court to jail
2018-08-21 00:00:00
PornHub
10:25
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
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
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
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
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
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
Futile sissy stud can't sate Micky Lynn
Futile sissy stud can't sate Micky Lynn
2018-10-14 00:00:00
xHamster
7:00
The sissy, his wifey & The Saleswoman - Sissy Nylon harassment Trailer
The sissy, his wifey & The Saleswoman - Sissy Nylon harassment Trailer
2018-09-15 00:00:00
PornHub
0:38
Sissy Charlotte eats out my pussy and she is a quick learner
Sissy Charlotte eats out my pussy and she is a quick learner
2021-05-20 00:00:00
SunPorno
8:06
Domina mom Gives strapped Sissy hand-job jerking
Domina mom Gives strapped Sissy hand-job jerking
2018-08-26 00:00:00
PornHub
1:42
sissy Arab Saudi fucking
sissy Arab Saudi fucking
2020-01-13 00:00:00
xHamster
0:10
Parent pounds sissy queer
Parent pounds sissy queer
2018-10-06 00:00:00
PornHub
1:39
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

Cuckold sissy husband getting off watching wife with BBC bul
Cuckold sissy husband getting off watching wife with BBC bul
2023-03-18 00:00:00
SunPorno
14:10
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
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
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
Sissy is dripping on my foot 💦
Sissy is dripping on my foot 💦
2022-12-13 00:00:00
PornHub
8:54
'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
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
Smothered Sissy Cuckold
Smothered Sissy Cuckold
2021-09-20 00:00:00
xHamster
1:01:15
'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
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
Cuckold MILF and her 2 BBC bulls – Sissy husband watches
Cuckold MILF and her 2 BBC bulls – Sissy husband watches
2021-09-27 00:00:00
xHamster
14:31
'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 slut gives her ass to his wife Domme- full clip on my Onlyfans (link in bio)
Sissy slut gives her ass to his wife Domme- full clip on my Onlyfans (link in bio)
2021-06-15 00:00:00
PornHub
0:13
Sissy Vicky gets so horny sucking big cock
Sissy Vicky gets so horny sucking big cock
2021-09-23 00:00:00
PornHub
1:43
Cuckolds’ secrets – 2 BBCs fucking hot wife, Sissy watching
Cuckolds’ secrets – 2 BBCs fucking hot wife, Sissy watching
2021-10-13 00:00:00
xHamster
13:21
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
Lana cd making her sissy cock hard in mini skirt thong and stockings
Lana cd making her sissy cock hard in mini skirt thong and stockings
2022-07-16 00:00:00
PornHub
3:40
Big black cock addiction: cock-sucking sissy mega-bitch
Big black cock addiction: cock-sucking sissy mega-bitch
2019-05-15 00:00:00
PornHub
4:47
Cuckolds secrets – 2 BBCs fucking sissy’s wife
Cuckolds secrets – 2 BBCs fucking sissy’s wife
2021-09-26 00:00:00
xHamster
13:07
Sissy School Education FemDom POV Video
Sissy School Education FemDom POV Video
2021-05-23 00:00:00
PornHub
8:09
Mistress Fiona and Her cute sissy slave (phone footage)
Mistress Fiona and Her cute sissy slave (phone footage)
2022-06-01 00:00:00
xHamster
2:18
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