Sissy Boy 135 videos

Popular Latest Top rated

16:49 84%

Thats a big boy

2 years ago
PornHub
shemale, anal, teen anal (18+), crossdresser, bareback, sissy, amateur
15:35 92%

Ash Steele In Im A Boy And Wear Girls Clothes Sometimes.

2 years ago
PornHub
emo, crossdresser, clothed, sissy, anal, shemale
24:57 90%

Sissy MILF Maid Seduced By Teenage Boy

7 months ago
Analdin
mature, MILF, maid, 18, sissy, big ass, seduced
19:46

Maximum anal stuffing for my sissy boy! Reward for deep insertion and pegging!

1 week ago
JizzBunker
huge dildo, femdom, crossdresser, sissy
24:57 88%

Sissy - Maid Seduced By Teen Boy(4K) - 4k ultra hd

5 months ago
xHand
mature, amateur, slut, maid, seduced, 18, teen (18+)
45:33 92%

I am having so much fun stuffing dildo into my boy pussy and cumming all over my body

1 year ago
PornHub
huge dildo, crossdresser, clothed, sissy, cum on pussy
22:27

SANDY CD PLAYS WITH THE PLUMBER AND MILKS HIS MILK

9 months ago
PornHub
crossdresser, plumber
24:57

Amoral horny MILF amazing adult video

4 months ago
XoZilla
MILF, maid, sissy
15:51

Therapy session for SISSY BOYS 2

3 weeks ago
PornHub
blonde, sissy
30:22 50%

Feminized sissy boy gets face fucked with a strap-on & feet dominated

6 years ago
MegaTube
CFNM, sissy
29:11

Submissive Sissy Ejaculates Inside His Lady Prematurely - Nylonlingerie Studio With Slut Boy

1 year ago
Upornia
sissy
17:17 82%

Sandy, cd, fucks the masons of her renovation.

9 months ago
PornHub
crossdresser, gangbang
30:39 81%

Sissy Boy Pegging - Cuckold Sex - Shae Celestine

2 years ago
HDZog
bisexual, cuckold, pegging, sissy
59:18 64%

Giantess Sissy Slut Femdom Sex Tall Goddess Amanda dominat and humiliate her crossdresser bitch boy!

11 months ago
xHamster
femdom, tall, crossdresser, sissy
22:08

Kianna Dior jerks off huge cock of sissy boy

2 weeks ago
Analdin
fetish, big tits, jerking, cougar, sissy
24:38 83%

Love the sissy boys

4 years ago
TXXX
femdom, sissy
19:51

Jay West And Riley Reid - I Love Sissy Boys - See Riley With Her Strap On, Shove It Inside All His Naughty Holes

1 year ago
Upornia
femdom, pegging, sissy
19:24

Young Allie North CD raw hot teen

1 year ago
PornHub
train, crossdresser, toys, sissy
59:13

Giantess Sissy Slut Femdom Sex Tall Dominat And Humiliate Her Crossdresser Bitch Boy! - Tall Goddess And Goddess Amanda

9 months ago
TXXX
crossdresser, sissy
24:05

Jenevieve Hexxx And Savana Styles - Jen And Savana Spank And Peg A Sissy Boy!

2 years ago
VXXX
pegging
23:11

KINKYHOME TV - NEW SEASON 2023 - BONUS SCENE (Emily Candys & Justin Sweetsun)

9 months ago
xHamster
femdom
31:50 76%

Boss Fuck Sissy Boy

2 years ago
HClips
strapon, sissy
18:50

Smooth femboy rides BBC balls deep

2 years ago
PornHub
sissy
48:05 68%

Busty sissy CD gives a straight guy a 48 min sloppy BJ

1 year ago
PornHub
crossdresser, sissy
24:57

Sissy Milf Maid Seduced By Teenage Boy

3 months ago
TXXX
stockings, MILF, hairy, seduced
20:15

You Will Beg Me To Link You To This Video. Big Compilation.

1 year ago
PornHub
prostate, domination, orgasm compilation, pegging, sissy
20:20

I Love Sissy Boys - See Riley with her Strap on, shove it inside all his naughty holes.

1 year ago
PornHub
domination, pegging, sissy
19:46

Maximum Anal Stuffing for my Sissy Boy! Deep Insertion and Pegging Reward!

1 month ago
xHamster
pegging
19:25

Ep. 1 Mistress Kayla Swallow Mommys Big COCK like a Good Sissy Boy with CUMSHOT!

2 years ago
PornHub
sissy
16:06

French Dominatrix Pegging With Sissy Boy

2 years ago
Upornia
pegging, sissy
30:39

Shae Celestine Sissy Boy Pegging - cuckold sex

3 years ago
XoZilla
strapon, sissy
16:11

Soft dick sucking

8 months ago
PornHub
sissy
26:21

Sissy boys wedding

4 years ago
XXXDan
bride, wedding, sissy
31:26

Sissy princess want to pee. But it s only allowed while fucking ass!

5 months ago
PornHub
toilet, fetish
22:47

EveMartini- Delivery Girl helps client transform in a sissy boy @lourdesmodels

2 months ago
PornHub
sissy, delivery
17:11 54%

CD SISSY HAS A THREESOME WITH TWO BROTHERS

9 months ago
PornHub
crossdresser, sissy
25:50

Strapping Toy Boy Gets Sex Education From Mature Sissy Neri

11 months ago
Upornia
mature
26:08 81%

Sexy cd sissy, rich fuck with her young neighbor

9 months ago
PornHub
crossdresser
19:55

Sticking my massive cock into this tiny toy

4 months ago
PornHub
sissy
17:53

Sensual dominatrix feminizes her boy in stockings with a strapon

2 years ago
xHamster
prostate, sissy, romantic
20:55

CUMS TWICE!! CLOSE UP ANAL and SQUIRTING HUGE SISSYGASM!!!

6 months ago
PornHub
huge dildo, sissy
30:36

Sissy Boy Pegging

3 years ago
SunPorno
sissy
36:06

Chubby Slut Gives Sissy Boy Toy Anal Masturbation Play And Cum Eating Instructions

8 months ago
HClips
sissy
17:18

Sissy Boy Webcam Show

5 years ago
Analdin
sissy
20:03

Super Hot GILF Blonde Forces A Young Sissy Boy To Fuck Her

4 years ago
TXXX
sissy, GILF
31:39

Boot femdom ball busting & riding sissy boy

7 years ago
MegaTube
sissy
1:05:32 56%

Positive Sissy Affirmations with Binaural Beats by Miss Lofn

2 years ago
PornHub
femdom, train, sissy, ASMR
24:57

Naughty mistresses know how to treat their sissy boys

7 years ago
BravoTube
sissy
15:25

Femdom, She love Rimming and Torture Balls

3 years ago
PornHub
sissy
16:01

Allie North deepthroating and being a bad girl

1 year ago
PornHub
train, crossdresser, sissy
15:41

Strap On Dildos Ladies wanna make to Be A Female To A Hot Dude

3 years ago
PornHub
sissy
36:11

Chubby slut gives sissy boy toy anal masturbation play and cum eating instructions

9 months ago
xHamster
toys
35:52

Sissy Boy Joi Cei And Anal Instructions

9 months ago
HClips
JOI, sissy
15:32

Yaoi Femboy - Sissy boy anal sucking dick and jerk off

11 months ago
xHamster
sissy
17:11

Getting Fisted Like A Slutty Sissy Boy!!

9 months ago
HClips
sissy
1:06:03

Sissy boy slut playing for the cam.

11 months ago
PornHub
sissy
16:06

Vends-ta-culotte - French dominatrix gets attached to a sissy boy

1 year ago
JizzBunker
sissy
15:56

Sloppy sucking deep throat sissy boy almost busted

1 year ago
PornHub
train, crossdresser, sissy
22:23

2 Mistresses And Sissy Boy

2 years ago
TXXX
sissy
16:40 67%

Hot Amateur Girl Pegging Hard Her Sweet Sissy Boy

1 year ago
PornHub
crossdresser, pegging, sissy, chastity
41:08

Blonde dominatrix controls her sissy boy

2 years ago
NuVid
sissy
16:15

Hot Amateur Girl Pegging Hard Her Sweet Sissy Boy

2 years ago
TXXX
sissy
20:01

Slut Bottom Chris, Aiden Starr And Kiki Daire - Kiki And Aiden Use A Massive Black Toy To Peg A Sissy Boy!

2 years ago
VXXX
pegging, sissy
26:11

Mistress Cleo Will Blow Your Pathetic Sissy Boy Mind With This Vid Boyz: Sch For Tinies

2 years ago
HClips
smoking, sissy
17:22

Humiliation rating, sissy boy, sph

2 years ago
HDSex
sissy
17:39

Muslim Sissy Boy Friend 3

2 years ago
Upornia
sissy
19:46

German Mistress Sissy Boy Humiliation II

4 years ago
TXXX
sissy
1:04:59

SISSY BOY ACTION - Femdom crossdresser teens fart and fisting fuck

3 years ago
HClips
farting, crossdresser, sissy
17:44

Dominate Cunt Sexually Torments Sissy Boy

5 years ago
TXXX
sissy
23:00

German Mistress Sissy Boy Humiliation I

4 years ago
TXXX
sissy
40:27

Sissy Boy Joins in a Threesome

5 years ago
HClips
sissy
16:39

Sissy boy fuck hard

5 years ago
TXXX
sissy
47:58

Sissy boy dominated

5 years ago
TXXX
sissy
29:20

Stepmom and Dauther Pegging Sissy Boy

6 years ago
DrTuber
pegging, sissy
19:21

Teen Cuckold with sissy boy

6 years ago
TXXX
sissy
28:31

Sissy boy worships dirty socks & is cruelly ass spanked

6 years ago
MegaTube
socks, sissy
20:56

Sissy boy gets feet dominated spanked & facesitting

7 years ago
MegaTube
CFNM, sissy
39:30

Sissy boy gagged and dominated with a huge strapon

7 years ago
MegaTube
sissy
19:26

Sissy boy gets strapon fucked by the mistress

8 years ago
HClips
sissy
19:42

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8 years ago
xHamster
sissy
22:29

Amateur - BiSex Sissy Boy MMF Threesome CIM Facial

9 years ago
TXXX
sissy
28:57

Strapon Sissy Boys

9 years ago
xHamster
sissy
17:42

Two Sissy boys play on webcam 3

9 years ago
xHamster
sissy
17:37

On Your Toes Sissy Boy

10 years ago
xHamster
sissy
16:11

Mistress Fuck Sissy Boys

10 years ago
xHamster
sissy
15:15

Sissy Boy Whipped And fucked In The Ass

10 years ago
xHamster
sissy
15:15

Sissy Boy Dominated And Fucked In the Ass

10 years ago
xHamster
sissy
21:49

Sissy Boy's Ruined Agonorgasmos Cum Eating

10 years ago
TXXX
sissy
15:09

Sissy boy fucking

12 years ago
xHamster
sissy
24:17

Mistress sissy boy Strapon

11 years ago
xHamster
sissy
23:19

First time Sissy training FIST with hands free orgasm!

3 months ago
PornHub
crossdresser, sissy, chastity
24:57

Sissy - Maid Seduced By Teen Boy(4K) - Teen

8 months ago
xTits
maid
29:48

Good Boy Sissy Goon

6 months ago
XXXDan
sissy
24:50

Mandyletspandy - Lets Ride Full Cut - Sissy Crossdresser does anal for you!

1 year ago
PornHub
train, crossdresser, slut, sissy
26:59

Sissy cd, making her friends fantasies come true

9 months ago
PornHub
crossdresser, sissy
18:25

Cute Boy Self Piss And Cumshot

1 year ago
PornHub
crossdresser, sissy
15:31

Sissy Faggot Boy, Come Out Of Closet¡ Joi With Toys, As

1 year ago
Upornia
sissy
19:00

Sissy Allie North have fun with a massive dildo hardcore

1 year ago
PornHub
train, crossdresser, sissy
18:23

Pink sissy changing clothes into witch outfit

1 year ago
PornHub
sissy
17:23

SISSY WALK IN THE WOODS IN PUBLIC

1 year ago
PornHub
crossdresser, sissy, skirt
19:59

Mistress Rough Dominating Sissy Faggot Totally Restrained Bdsm In Amazon While Rimming And Spanking His Ass - Slut Boy

2 years ago
HClips
sissy
19:59

Mistress rough dominating sissy faggot slut boy totally restrained bdsm in amazon while rimming and spanking his ass

2 years ago
xHamster
sissy, colombian
17:31

Slutty Boy Gaped and Pegged in Nylons by Horny MILF mistress

2 years ago
xHamster
sissy
20:38

Sissy training: how to cum in chastity? Ride ever bigger dildos to sissygasm

2 years ago
PornHub
train, sissy, chastity
19:55

Mistress Amazon Goddess Sucking And Fucking The Sissy Faggot Boy In Amazon Position Bdsm Mistreating

2 years ago
Upornia
sissy
24:31

Femdom Amazon Position Fucking The Sissy Slave Boy After Massging His Balls And Cock Rough Fucking

2 years ago
Upornia
sissy
15:48

Sissy Femdom Compilation - Tusspuss

2 years ago
PornHub
swedish, sissy, chastity
18:58

HD: Verbal Daddy FTM Transman fucks tight boypussy ass (For the SUB Men and Sissies! ;)

2 years ago
PornHub
crossdresser, sissy
19:10

White Boy & Sissy Relaxation: Interracial Love

3 years ago
SunPorno
sissy
16:01

Amazon Teen Tying Up Sissy Blindfolded Boy With Black Tape Fucks Him & Peeing His Face With His Cum

2 years ago
HClips
tied, sissy, blindfolded
23:42

Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo

3 years ago
PornHub
train, prostate, crossdresser, sissy, chastity
20:18

I Spank and Rimming my Sissy Booty Boy - Femdom LiljaSwitch

4 years ago
PornHub
fetish, sissy
16:10

With music Sissy Japanese boy having fun with fleshlight and butplug

3 years ago
PornHub
sissy
18:39

Jaime Rey used as a Sissy Penetrate Plaything (lengthy Version with Lots of Handballing)

4 years ago
TrannyGem
crossdresser, sissy
18:15

Boy gets feminized and bum screwed in prison by chick

4 years ago
HDSex
sissy
18:42

Fine Boy - Femdom Facesitting SPH Chastity Sissy (some cock and ball torture and foot Fetish)

4 years ago
HDSex
sissy, chastity
32:17

Sissy long hair pretty boy

6 years ago
TXXX
long hair
20:50

Sissy trans boy shaves his pussy and plays with himself

5 years ago
PornHub
sissy
17:36

Good sissies cum out thieyre boy pussy

7 years ago
JizzBunker
sissy
16:41

My MILF Exposed Mature wife with BBC stunt boy Cuckold sissy

7 years ago
xHamster
sissy

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