Longest Videos Tagged with sissy

AllHD
PARATHD-4035 Yankee sissy made to come hard by sexual massage (6) Sakura Misaki
720p HD
3 834 views
115:33

PARATHD-4035 Yankee sissy made to come hard by sexual massage (6) Sakura Misaki

  • 1 year ago
  • 0%
Dominatrix Smothers Her Sissy Subs
480p
5 466 views
52:51

Dominatrix Smothers Her Sissy Subs

  • 5 years ago
  • 75%
Mature Italian slut Sissy Neri takes many cocks today
1080p HD
10 444 views
50:00

Mature Italian slut Sissy Neri takes many cocks today

  • 4 years ago
  • 95%
Amateur sissy was awesome when she took off her clothes! She has big labia and her big clitoris is entangled with a meat pole. She has a natural F cup and an oversized clitoris. I ejaculated inside of her without thinking!
1080p HD
6 869 views
49:29

Amateur sissy was awesome when she took off her clothes! She has big labia and her big clitoris is entangled with a meat pole. She has a natural F cup and an oversized clitoris. I ejaculated inside of her without thinking!

  • 1 year ago
  • 100%
OnlyTaboo - BBW Sandy Orhidea Sissy Wild Anal Mature Party Orgy
1080p HD
12 156 views
48:49

OnlyTaboo - BBW Sandy Orhidea Sissy Wild Anal Mature Party Orgy

  • 11 months ago
  • 84%
BNWO comp 2
480p
11 367 views
47:22

BNWO comp 2

  • 1 year ago
  • 72%
Sissy Gold - XXXX - My first and only DP
720p HD
13 844 views
40:19

Sissy Gold - XXXX - My first and only DP

  • 5 years ago
  • 86%
AliceInBondageLand - Tabitha Sissy StrapOn Fucking Alic
1080p HD
4 192 views
36:45

AliceInBondageLand - Tabitha Sissy StrapOn Fucking Alic

  • 6 years ago
  • 100%
CumeatingCuckolds - The Sissy Tax 720p
720p HD
11 935 views
36:20

CumeatingCuckolds - The Sissy Tax 720p

  • 5 years ago
  • 95%
Sissy Neri Omar Galanti - Sissy Neri And Stud Have Hardcore Sex
1080p HD
4 492 views
34:58

Sissy Neri Omar Galanti - Sissy Neri And Stud Have Hardcore Sex

  • 6 months ago
  • 100%
Daisy Stone - Is It Cheating in SD
480p
33 520 views
34:34

Daisy Stone - Is It Cheating in SD

  • 5 years ago
  • 87%
{{{Prado Hardcore Cuckold}}}
720p HD
14 002 views
33:01

{{{Prado Hardcore Cuckold}}}

  • 4 years ago
  • 86%
MagmaFilm - Sissy boyfriend
1080p HD
4 337 views
31:27

MagmaFilm - Sissy boyfriend

  • 4 years ago
  • 66%
CumeatingCuckolds - Shae Celestine Sissy Boy Pegging
1080p HD
26 526 views
30:39

CumeatingCuckolds - Shae Celestine Sissy Boy Pegging

  • 5 years ago
  • 90%
Newcummer Kaden gets sodomized
1080p HD
3 610 views
30:19

Newcummer Kaden gets sodomized

  • 5 months ago
  • 75%
(( Tera_Dice_Cuckolds ))
720p HD
12 617 views
30:17

(( Tera_Dice_Cuckolds ))

  • 4 years ago
  • 90%
Bobbi Starr Moms Cuckold
720p HD
18 027 views
30:03

Bobbi Starr Moms Cuckold

  • 5 years ago
  • 85%
Sissy Neri - The bored wife
720p HD
6 031 views
29:56

Sissy Neri - The bored wife

  • 4 years ago
  • 100%
Sissy Neri - The bored wife - Interracial - DP - Ass Do
1080p HD
5 912 views
29:56

Sissy Neri - The bored wife - Interracial - DP - Ass Do

  • 2 years ago
  • 88%
Little Red Speculum
4K
3 950 views
29:26

Little Red Speculum

  • 3 years ago
  • 92%
Amanda Becker & Joanna Queen - Mature CD Girlfriends End Up With The Same Guy in HD
1080p HD
7 201 views
29:17

Amanda Becker & Joanna Queen - Mature CD Girlfriends End Up With The Same Guy in HD

  • 3 years ago
  • 82%
FOXY ALEX VS NATE ROSS
1080p HD
30 491 views
29:01

FOXY ALEX VS NATE ROSS

  • 11 months ago
  • 100%
AliceInBondageLand - Public Butt Plug Sissy Walk Part 1
1080p HD
4 844 views
28:12

AliceInBondageLand - Public Butt Plug Sissy Walk Part 1

  • 6 years ago
  • 100%
( [Clean Out My Pussy Cuckold - Anya Olsen] )
1080p HD
31 855 views
28:11

( [Clean Out My Pussy Cuckold - Anya Olsen] )

  • 5 years ago
  • 88%
Cumeatingcuckolds - Maya Morgen
1080p HD
27 527 views
27:47

Cumeatingcuckolds - Maya Morgen

  • 4 years ago
  • 95%
Grayson Enjoys Riding Studly Bryce's Saddle Horn
1080p HD
7 301 views
27:26

Grayson Enjoys Riding Studly Bryce's Saddle Horn

  • 1 year ago
  • 100%
Summer - Discovering The Perfect Asian Sissy (20.09.2024)_1080p
1080p HD
5 900 views
27:15

Summer - Discovering The Perfect Asian Sissy (20.09.2024)_1080p

  • 1 year ago
  • 80%
Milf Ass
720p HD
4 479 views
26:52

Milf Ass

  • 8 years ago
  • 100%
Sissy Neri - Drunk Of Cream Of Your Cock
1080p HD
16 322 views
26:52

Sissy Neri - Drunk Of Cream Of Your Cock

  • 7 years ago
  • 98%
LustyGrandmas - Sissy Neri - Naughty Sissy Titty Cumsho
1080p HD
63 849 views
26:40

LustyGrandmas - Sissy Neri - Naughty Sissy Titty Cumsho

  • 7 years ago
  • 93%
Doja Brat Sissy Princess Arrives To Please Him
480p
13 473 views
26:28

Doja Brat Sissy Princess Arrives To Please Him

  • 3 years ago
  • 88%
{{{1614_New_Boyfriend}}}
720p HD
8 674 views
26:21

{{{1614_New_Boyfriend}}}

  • 4 years ago
  • 71%
Submissive Cuckolds 4k
4K
17 911 views
26:16

Submissive Cuckolds 4k

  • 3 years ago
  • 90%
Chloe Cherry - Cum Eating Cuckolds
480p
17 235 views
26:11

Chloe Cherry - Cum Eating Cuckolds

  • 6 years ago
  • 77%
AliceInBondageLand - Sissy StrapOn Xmas Present Part 1
1080p HD
3 518 views
25:55

AliceInBondageLand - Sissy StrapOn Xmas Present Part 1

  • 6 years ago
  • 80%
CumeatingCuckolds - Gia Vendetti Sissy Cuck Clean Up
1080p HD
41 017 views
25:28

CumeatingCuckolds - Gia Vendetti Sissy Cuck Clean Up

  • 5 years ago
  • 92%
maxcuckold.com Cuckold Busty Blonde
480p
12 887 views
25:08

maxcuckold.com Cuckold Busty Blonde

  • 8 years ago
  • 53%
Cum & Sloppy Cock Sucking Brainwash - Split Screen Compilation
1080p HD
25 500 views
25:03

Cum & Sloppy Cock Sucking Brainwash - Split Screen Compilation

  • 5 years ago
  • 98%
Mature Sissy maid fantasy
1080p HD
4 316 views
24:57

Mature Sissy maid fantasy

  • 1 week ago
  • 100%
Grinding That Fist - s01 - Angel Piaff - Sissy A.
720p HD
5 237 views
24:55

Grinding That Fist - s01 - Angel Piaff - Sissy A.

  • 6 years ago
  • 100%
AliceInBondageLand - Golden Gate Bridge Sissy 2
1080p HD
5 569 views
24:45

AliceInBondageLand - Golden Gate Bridge Sissy 2

  • 6 years ago
  • 100%
OnlyFans - Faye Lockwood - Spider Boy XXX Sissy Sucking
1080p HD
2 025 views
24:24

OnlyFans - Faye Lockwood - Spider Boy XXX Sissy Sucking

  • 6 months ago
  • 100%
That Cuckold HUsband
720p HD
14 072 views
23:06

That Cuckold HUsband

  • 4 years ago
  • 100%
Cuckold Cleans Up After Condom Breaks
1080p HD
26 864 views
22:50

Cuckold Cleans Up After Condom Breaks

  • 5 years ago
  • 89%
DommeMommy Turns You Into Sissified Bi Cuck PART 2
720p HD
8 611 views
22:41

DommeMommy Turns You Into Sissified Bi Cuck PART 2

  • 4 years ago
  • 84%
Goddess Kendall - Sissy Bruvver For Huge BBC
1080p HD
1 115 views
22:29

Goddess Kendall - Sissy Bruvver For Huge BBC

  • 3 weeks ago
  • 100%
Mischa Brooks - Cum Eating Cuckolds
480p
14 965 views
22:22

Mischa Brooks - Cum Eating Cuckolds

  • 6 years ago
  • 82%
Cum Eating Cuckolds - Cum Eater
1080p HD
58 759 views
21:52

Cum Eating Cuckolds - Cum Eater

  • 5 years ago
  • 89%
Teen Sissy Solo for Xmas
480p
3 397 views
21:21

Teen Sissy Solo for Xmas

  • 6 years ago
  • 62%
AliceInBondageLand - Sissy StrapOn Xmas Present Part 2
1080p HD
5 393 views
20:56

AliceInBondageLand - Sissy StrapOn Xmas Present Part 2

  • 6 years ago
  • 100%
Goddess Valora - StepMommys Gender Changing Sissy Training
1080p HD
1 486 views
20:50

Goddess Valora - StepMommys Gender Changing Sissy Training

  • 4 weeks ago
  • 0%
Sissy - Ball Game for GILFs
1080p HD
15 365 views
20:46

Sissy - Ball Game for GILFs

  • 5 years ago
  • 97%
Sissy – Ball Game for GILFs
480p
5 771 views
20:46

Sissy – Ball Game for GILFs

  • 5 years ago
  • 85%
Sucking Cock Sissy
720p HD
5 248 views
20:32

Sucking Cock Sissy

  • 2 years ago
  • 64%
££££.[[Nikky_Thorne]].%%%%
1080p HD
4 066 views
20:01

££££.[[Nikky_Thorne]].%%%%

  • 3 years ago
  • 77%
Split-Screen Cum & Sloppy Cock Sucking Sissy Brainwash
1080p HD
15 808 views
20:00

Split-Screen Cum & Sloppy Cock Sucking Sissy Brainwash

  • 5 years ago
  • 94%
Sissy - My Daughters Suitor
720p HD
15 569 views
19:49

Sissy - My Daughters Suitor

  • 6 years ago
  • 97%
Sissy - New Home New Lover
720p HD
11 498 views
19:46

Sissy - New Home New Lover

  • 5 years ago
  • 97%
Your Sissy Fate Is Sealed
720p HD
5 132 views
19:08

Your Sissy Fate Is Sealed

  • 4 years ago
  • 100%
Sissy Gold - Amateur couple tries new toys
1440p
6 623 views
19:07

Sissy Gold - Amateur couple tries new toys

  • 5 years ago
  • 100%
Sissy - Inner Harmony
1080p HD
9 532 views
18:34

Sissy - Inner Harmony

  • 5 years ago
  • 92%
Office sissy caption story
1080p HD
13 829 views
18:24

Office sissy caption story

  • 2 years ago
  • 100%
ªªª{{{{JOI&CEI}}}}²³²££
1080p HD
2 378 views
17:51

ªªª{{{{JOI&CEI}}}}²³²££

  • 3 years ago
  • 100%
Poppers For Panty Wearing Sissy
1080p HD
21 738 views
17:36

Poppers For Panty Wearing Sissy

  • 4 years ago
  • 61%
TheEnglishMansion - Tethered Sissy Maid
720p HD
4 899 views
17:29

TheEnglishMansion - Tethered Sissy Maid

  • 4 years ago
  • 100%
Aliza Breeze - Black Beauty Is a Submissive Sissy in HD
1080p HD
4 530 views
16:22

Aliza Breeze - Black Beauty Is a Submissive Sissy in HD

  • 2 years ago
  • 100%
Hot Psycho JOI For You Sissy
1080p HD
6 327 views
16:13

Hot Psycho JOI For You Sissy

  • 5 years ago
  • 100%
ScarlettBelle - Becoming My Sissy Maid
1080p HD
547 views
16:07

ScarlettBelle - Becoming My Sissy Maid

  • 1 week ago
  • 0%
Ella Nova Winkie Humiliation during diaper change
1080p HD
16 216 views
15:47

Ella Nova Winkie Humiliation during diaper change

  • 5 years ago
  • 90%
Sissy big balls and cock teasing
480p
4 906 views
15:34

Sissy big balls and cock teasing

  • 6 years ago
  • 87%
Denise Masino As Dominatrix Sissy Training
720p HD
3 105 views
15:13

Denise Masino As Dominatrix Sissy Training

  • 4 months ago
  • 100%
GS - Tobias (g501)
480p
6 442 views
14:59

GS - Tobias (g501)

  • 8 years ago
  • 100%
SavannahxSiren - Girlfriend Encouraged Sissy Feminization - Strap On POV
1080p HD
1 053 views
14:45

SavannahxSiren - Girlfriend Encouraged Sissy Feminization - Strap On POV

  • 3 weeks ago
  • 100%
Sissy Slut Prepares for BBC
1080p HD
8 676 views
14:42

Sissy Slut Prepares for BBC

  • 5 years ago
  • 74%
Skin Diamond - D0ggy-chow Sissy Humiliation
1080p HD
9 918 views
13:50

Skin Diamond - D0ggy-chow Sissy Humiliation

  • 7 years ago
  • 88%
Skin Diamond - D0ggy-chow Sissy Humiliation
1080p HD
6 948 views
13:50

Skin Diamond - D0ggy-chow Sissy Humiliation

  • 7 years ago
  • 83%
GS - Desmond (g564)
480p
4 565 views
13:39

GS - Desmond (g564)

  • 8 years ago
  • 80%
GS - Tommy (g521)
480p
5 361 views
13:17

GS - Tommy (g521)

  • 8 years ago
  • 80%
German Domina Lady Julina Transenschwuchtel Sissy Schwa
720p HD
4 377 views
13:10

German Domina Lady Julina Transenschwuchtel Sissy Schwa

  • 7 years ago
  • 80%
Jenna Ivory - Cuckold Humiliation
720p HD
18 560 views
12:58

Jenna Ivory - Cuckold Humiliation

  • 6 years ago
  • 78%
I dont care anymore sissy caption story
480p
15 327 views
12:54

I dont care anymore sissy caption story

  • 2 years ago
  • 100%
Telling Cuck About Her Need For Big Cocks
480p
7 184 views
12:26

Telling Cuck About Her Need For Big Cocks

  • 5 years ago
  • 100%
White boys become sissy cuckolds
1080p HD
5 230 views
12:17

White boys become sissy cuckolds

  • 5 years ago
  • 56%
Goddess Rose Thorne - Dolling Up My Sissy
1080p HD
1 028 views
12:11

Goddess Rose Thorne - Dolling Up My Sissy

  • 3 weeks ago
  • 50%
Jacky Pride - Super Cute Sailor Sissy
1080p HD
3 840 views
12:02

Jacky Pride - Super Cute Sailor Sissy

  • 2 years ago
  • 100%
021.Ivory_Cum_Licker (1080)
1080p HD
2 701 views
12:02

021.Ivory_Cum_Licker (1080)

  • 4 years ago
  • 100%
Sissy Tranny Begs For Love Juice On Hose
720p HD
3 014 views
12:01

Sissy Tranny Begs For Love Juice On Hose

  • 5 years ago
  • 100%
POV Teen Mistress Sissy Training JOI
480p
10 218 views
11:50

POV Teen Mistress Sissy Training JOI

  • 3 years ago
  • 85%
THEcherrygirl - Sissy transformation
1080p HD
265 views
11:49

THEcherrygirl - Sissy transformation

  • 1 week ago
  • 0%
Tatita Hilton - Fucking My Sissy Girl 08
720p HD
4 142 views
11:39

Tatita Hilton - Fucking My Sissy Girl 08

  • 4 years ago
  • 100%
GS - Gilbert (g539)
480p
6 171 views
11:35

GS - Gilbert (g539)

  • 8 years ago
  • 83%
FayValentine369 - Sissy HandJob
720p HD
2 312 views
11:33

FayValentine369 - Sissy HandJob

  • 4 years ago
  • 100%
KendraJames - Sissy Suckfest
720p HD
4 541 views
11:29

KendraJames - Sissy Suckfest

  • 6 years ago
  • 100%
Sissy Slut Training
1080p HD
5 562 views
11:21

Sissy Slut Training

  • 5 years ago
  • 100%
HotMomDomme - Bar Pickup Feminized and Fucked
1080p HD
1 090 views
11:20

HotMomDomme - Bar Pickup Feminized and Fucked

  • 3 weeks ago
  • 100%
Anikka Albrite - Worship The Booty Queen
720p HD
9 853 views
11:15

Anikka Albrite - Worship The Booty Queen

  • 6 years ago
  • 96%
Daddy's Sissy Slut Getting Anal Pleasure
720p HD
12 306 views
11:07

Daddy's Sissy Slut Getting Anal Pleasure

  • 7 years ago
  • 95%
TGirl Janie Blade Instructs You On Proper Sissy Etiquette
720p HD
2 621 views
11:07

TGirl Janie Blade Instructs You On Proper Sissy Etiquette

  • 4 years ago
  • 100%
Stacy’s girl - A sissy caption story
480p
14 956 views
11:01

Stacy’s girl - A sissy caption story

  • 11 months ago
  • 88%
KinkDevice - Jens Pink Sissy Peg Alt View
1080p HD
1 875 views
10:56

KinkDevice - Jens Pink Sissy Peg Alt View

  • 5 years ago
  • 100%
Kendall Olsen - Becoming My Sissy Boyfriend
1080p HD
962 views
10:52

Kendall Olsen - Becoming My Sissy Boyfriend

  • 1 month ago
  • 0%
KinkDevice - Jens Pink Sissy Peg
1080p HD
2 245 views
10:33

KinkDevice - Jens Pink Sissy Peg

  • 5 years ago
  • 100%
Meta Cum Compilation - Sissy Cum Brainwash
1080p HD
32 605 views
10:32

Meta Cum Compilation - Sissy Cum Brainwash

  • 6 years ago
  • 97%
Sissy Slut Fucks Her Hole With Fat Dildo
720p HD
3 967 views
10:30

Sissy Slut Fucks Her Hole With Fat Dildo

  • 4 years ago
  • 100%
Sissy Fuck Meat Has Fun With Her Machine
720p HD
4 924 views
10:29

Sissy Fuck Meat Has Fun With Her Machine

  • 4 years ago
  • 100%
MyDirtyHobby - PornbabeTyra - Erziehung zur Sissy - Mac
720p HD
6 077 views
10:22

MyDirtyHobby - PornbabeTyra - Erziehung zur Sissy - Mac

  • 6 years ago
  • 100%
Big tit German MILF Texas Patti gets pounded hard
1080p HD
9 835 views
10:22

Big tit German MILF Texas Patti gets pounded hard

  • 6 years ago
  • 100%
Sissy prostitute acquires Used
1080p HD
7 966 views
10:21

Sissy prostitute acquires Used

  • 6 years ago
  • 100%
Little Sissy Pirate Wench
1080p HD
4 562 views
10:17

Little Sissy Pirate Wench

  • 5 years ago
  • 71%
@@@.Arab_Mistress.@@'
720p HD
5 440 views
10:15

@@@.Arab_Mistress.@@'

  • 4 years ago
  • 100%
LuxuryLovers - Perfect Cumshot Compilation - Doggystyle
1080p HD
1 959 views
10:10

LuxuryLovers - Perfect Cumshot Compilation - Doggystyle

  • 2 years ago
  • 100%
Fingers In My Pussy and Squirt
1080p HD
2 800 views
10:08

Fingers In My Pussy and Squirt

  • 4 years ago
  • 100%
TGirl TrapaZoey - Sissy Bimbo Stroking
720p HD
1 464 views
9:53

TGirl TrapaZoey - Sissy Bimbo Stroking

  • 4 years ago
  • 100%
Sissy In valuable Classic costume
720p HD
3 383 views
9:51

Sissy In valuable Classic costume

  • 6 years ago
  • 100%
Goddess Julia - Sissy Slut - Chastity Training
1080p HD
4 280 views
9:47

Goddess Julia - Sissy Slut - Chastity Training

  • 1 year ago
  • 100%
Cate McQueen - Strap on instructions in 4K
4KVR
5 483 views
9:35

Cate McQueen - Strap on instructions in 4K

  • 3 years ago
  • 60%
Natasha Zare - Co-ed Makes You A Girl
1080p HD
439 views
8:56

Natasha Zare - Co-ed Makes You A Girl

  • 1 week ago
  • 0%
AliceInBondageLand - Public Butt Plug Sissy Walk Part 2
1080p HD
3 915 views
8:51

AliceInBondageLand - Public Butt Plug Sissy Walk Part 2

  • 6 years ago
  • 100%
Sissy Training With Dominatrix
720p HD
5 146 views
8:40

Sissy Training With Dominatrix

  • 4 years ago
  • 100%
Suck Sissy - The English Mansion
1440pVR
8 851 views
8:38

Suck Sissy - The English Mansion

  • 5 years ago
  • 83%