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Search results - First Sissy

Total found: 307 videos

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Boy first time masterbation First time sex videos First time masterbate video Desi girlfriend ko choda Indian b

5:05

5 months ago xHamster

Boy first time masterbation First time sex videos First time masterbate video Desi girlfriend ko choda Indian b

First time Hung Latino fucks his first CD Hole

11:06

4 years ago xHamster

First time Hung Latino fucks his first CD Hole

First anal sex videos foursome first time indian boy

5:12

1 year ago xHamster

First anal sex videos foursome first time indian boy

First time sissy takes dildo

1:15

8 years ago xHamster

First time sissy takes dildo

Virgin sissy boy first dildo ass fuck

1:21

8 years ago xHamster

Virgin sissy boy first dildo ass fuck

I want you to watch my first sissy crossdresser adventure

14:17

7 years ago xHamster

I want you to watch my first sissy crossdresser adventure

Sissy CD Vickie Robert's First Video for Master Karl.

12:40

7 years ago xHamster

Sissy CD Vickie Robert's First Video for Master Karl.

Sissy Crossdressers First Time Anal

3:18

7 years ago xHamster

Sissy Crossdressers First Time Anal

Sissy Suzy's first assignment for Master Karl

13:15

7 years ago xHamster

Sissy Suzy's first assignment for Master Karl

This is my first time as a crossdressing sissy

15:02

7 years ago xHamster

This is my first time as a crossdressing sissy

My first sissy adventure was better than I ever imagined

13:47

7 years ago xHamster

My first sissy adventure was better than I ever imagined

4:11

5 years ago xHamster

My First Video

CD releases cock from shiny knickers (my first video)

0:22

5 years ago xHamster

CD releases cock from shiny knickers (my first video)

Sissy Jen's first BBC latex hood suck

1:06

5 years ago xHamster

Sissy Jen's first BBC latex hood suck

German Amateur Sissy CD gets her first Fuck

1:06

4 years ago xHamster

German Amateur Sissy CD gets her first Fuck

first time sissy crossdress with dildos

28:23

4 years ago xHamster

First time sissy crossdress with dildos

Virgin sissy fucks ass for the first time

0:16

4 years ago xHamster

Virgin sissy fucks ass for the first time

New sissy crossdresser's first video

1:45

4 years ago xHamster

New sissy crossdresser's first video

My first sissygasm came with some pee.

0:35

4 years ago xHamster

My first sissygasm came with some pee.

One of my first vids from many years ago

6:38

4 years ago xHamster

One of my first vids from many years ago

Fucking my Sissy pussy, first video

0:22

4 years ago xHamster

Fucking my Sissy pussy, first video

Sissy Femboy Chrissy's First Video

1:00

4 years ago xHamster

Sissy Femboy Chrissy's First Video

Toy in virgin ass for first time

0:58

4 years ago xHamster

Toy in virgin ass for first time

Sissy CD first time caged, in a dress, heels, anal chair

16:02

4 years ago xHamster

Sissy CD first time caged, in a dress, heels, anal chair

This is my first time dressing like a sissy

17:09

4 years ago xHamster

This is my first time dressing like a sissy

Sissy takes first BBC in the ass and swallows cum

6:42

4 years ago xHamster

Sissy takes first BBC in the ass and swallows cum

Sissy first time 7 inch Dildo

1:47

4 years ago xHamster

Sissy first time 7 inch Dildo

Genuine first time anal and using a dildo (Curious)

1:12

4 years ago xHamster

Genuine first time anal and using a dildo (Curious)

0:09

4 years ago xHamster

First step

Cd man first time secret dildo games.close-up hairy asshole

2:08

4 years ago xHamster

Cd man first time secret dildo games.close-up hairy asshole

first dildo riding

1:22

4 years ago xHamster

First dildo riding

Sissy's first anal orgasm

1:25

4 years ago xHamster

Sissy's first anal orgasm

Pantyboy66's First Handsfree! Plus Slomo!

3:51

4 years ago xHamster

Pantyboy66's First Handsfree! Plus Slomo!

First six sissy rules

0:56

4 years ago xHamster

First six sissy rules

First time my sissy pussy was fucked

0:31

4 years ago xHamster

First time my sissy pussy was fucked

First Time in Chastity

3:37

4 years ago xHamster

First Time in Chastity

Sissyjen1 gets fucked and sucks cock for the first time!

5:24

4 years ago xHamster

Sissyjen1 gets fucked and sucks cock for the first time!

Dressing like a sissy for the first time got me so hard

17:27

4 years ago xHamster

Dressing like a sissy for the first time got me so hard

Sissy Bi Curious First Time Ruined Orgasm

0:47

4 years ago xHamster

Sissy Bi Curious First Time Ruined Orgasm

He Did Kiss Me First!

5:41

4 years ago xHamster

He Did Kiss Me First!

Crossdressed first time blowjob

1:15

4 years ago xHamster

Crossdressed first time blowjob

This will be my first sissy crossdressing adventure

15:29

4 years ago xHamster

This will be my first sissy crossdressing adventure

Sissies first anal beads

0:10

4 years ago xHamster

Sissies first anal beads

Sissys first ever public strip

3:41

4 years ago xHamster

Sissys first ever public strip

Sissy Crossdresser Slut fucked for first time

1:00

4 years ago xHamster

Sissy Crossdresser Slut fucked for first time

sissy slut sucking her first cock

0:09

4 years ago xHamster

Sissy slut sucking her first cock

sissy fucked from behind, her first big white cock

12:29

4 years ago xHamster

Sissy fucked from behind, her first big white cock

First time ever meeting someone from online

2:08

4 years ago xHamster

First time ever meeting someone from online

sissy fucked from behind, her first big arab cock

3:41

4 years ago xHamster

Sissy fucked from behind, her first big arab cock

Sucking my first BBC

4:11

4 years ago xHamster

Sucking my first BBC

sissy fucked from behind, her first big arab cock

1:00

3 years ago xHamster

Sissy fucked from behind, her first big arab cock

Your first time as a sissy will be amazing

16:28

3 years ago xHamster

Your first time as a sissy will be amazing

Mexican CROSSdresser having first Sissygasm From Sex

1:05

3 years ago xHamster

Mexican CROSSdresser having first Sissygasm From Sex

Crossdresser fucked by cucumber dildo (First time ANAL)

12:41

3 years ago xHamster

Crossdresser fucked by cucumber dildo (First time ANAL)

My first time as a sissy feels so right

17:55

3 years ago xHamster

My first time as a sissy feels so right

sissy fucked from behind, her first big arab cock

1:02

3 years ago xHamster

Sissy fucked from behind, her first big arab cock

Let me take you on your first sissy adventure

14:54

3 years ago xHamster

Let me take you on your first sissy adventure

The first time I crossdressed

4:11

3 years ago xHamster

The first time I crossdressed

Sissy boy first time NEW EXPLOSIVE vibrator

0:40

3 years ago xHamster

Sissy boy first time NEW EXPLOSIVE vibrator

First ride on sex machine and big dildo

1:48

3 years ago xHamster

First ride on sex machine and big dildo

First time STAR PERFORMER balls DEEP

1:01

3 years ago xHamster

First time STAR PERFORMER balls DEEP

First I have to put on my makeup

13:56

3 years ago xHamster

First I have to put on my makeup

My first privat show on xHamster live

1:33

3 years ago xHamster

My first privat show on xHamster live

Crossdressing Sissy Selfie, solo, first time taping

1:04

3 years ago xHamster

Crossdressing Sissy Selfie, solo, first time taping

Timid French Sissy First-Ever Time To Deepthroat

5:52

3 years ago Gay Ck

Timid French Sissy First-Ever Time To Deepthroat

Timid French sissy first-ever time to fellate

5:52

4 years ago Gay Ck

Timid French sissy first-ever time to fellate

JISM-CAP#1 "gia Calzone's first-ever JIZZ-pilation Video"

3:06

4 years ago Gay Ck

JISM-CAP#1 "gia Calzone's first-ever JIZZ-pilation Video"

My very first Movie! how to use an Assfuck Butt-Plug sans any Hurt in your Rear Entrance

7:57

3 years ago Gay Ck

My very first Movie! how to use an Assfuck Butt-Plug sans any Hurt in your Rear Entrance

CROSSDRESSER IN STRETCH PANTS AND SHOES FOR THE VERY FIRST TIME

6:51

3 years ago Gay Ck

CROSSDRESSER IN STRETCH PANTS AND SHOES FOR THE VERY FIRST TIME

Bashful French Sissy First-Ever Time To Deepthroat

5:52

3 years ago Gay Ck

Bashful French Sissy First-Ever Time To Deepthroat

Step Parent Breeding his Step Stepson in Quarantine for very first Time

6:50

4 years ago Gay Ck

Step Parent Breeding his Step Stepson in Quarantine for very first Time

Bashful French sissy first-ever time to gargle

5:52

4 years ago Gay Ck

Bashful French sissy first-ever time to gargle

Crossdressing first-ever Time

9:09

5 years ago Gay Ck

Crossdressing first-ever Time

My very first Sissygasm (Railing ample fuck stick)

2:51

6 years ago Gay Ck

My very first Sissygasm (Railing ample fuck stick)

Hetero Father Gets his Donk Breeding for the first-ever Time.

7:06

4 years ago Gay Ck

Hetero Father Gets his Donk Breeding for the first-ever Time.

Heather%27s very first BIG BLACK COCK.

10:20

6 years ago Gay Ck

Heather%27s very first BIG BLACK COCK.

Poke my Booty and Jizm, very first Going Knuckle Deep

7:14

4 years ago Gay Ck

Poke my Booty and Jizm, very first Going Knuckle Deep

I was so nervous the first time I put on lingerie

16:04

3 years ago xHamster

I was so nervous the first time I put on lingerie

Alxtoyboy My first time Anal pump and gape with my lovely Dildo

7:47

3 years ago xHamster

Alxtoyboy My first time Anal pump and gape with my lovely Dildo

Sissy first time in chasity playing with ass

3:55

3 years ago xHamster

Sissy first time in chasity playing with ass

Alxtoyboys Valentines Day in a Paris Hotel my first Penis Stick

10:04

3 years ago xHamster

Alxtoyboys Valentines Day in a Paris Hotel my first Penis Stick

My very first vid, I wear my underpants and brief top.

5:09

3 years ago Gay Ck

My very first vid, I wear my underpants and brief top.

My first sissy adventure was hotter than I ever imagined

14:55

3 years ago xHamster

My first sissy adventure was hotter than I ever imagined

First a rough fuck with my fuckingmachine than pushing all out

1:34

3 years ago xHamster

First a rough fuck with my fuckingmachine than pushing all out

1:03

3 years ago xHamster

My first cum

My first of many videos showing my ass in jock

1:06

3 years ago xHamster

My first of many videos showing my ass in jock

Bubble butt crossdresser Danielle first dildo fuck

1:38

3 years ago xHamster

Bubble butt crossdresser Danielle first dildo fuck

First time with my toy in tights 2

3:30

3 years ago xHamster

First time with my toy in tights 2

My first-ever movie.

5:09

3 years ago Gay Ck

My first-ever movie.

Fag Andrew Brown makes his first "Corno" vid

3:25

3 years ago xHamster

Fag Andrew Brown makes his first "Corno" vid

Katwinka gets his dick sucked for the first time! The student becomes the master! And he is enjoying that so much!!

34:02

3 years ago xHamster

Katwinka gets his dick sucked for the first time! The student becomes the master! And he is enjoying that so much!!

first time masturbation coe out huge sperm

2:08

3 years ago xHamster

First time masturbation coe out huge sperm

Playing with my beautiful body in the morning, shows for the first time

1:06

3 years ago xHamster

Playing with my beautiful body in the morning, shows for the first time

My first attempt at double dildos

1:27

3 years ago xHamster

My first attempt at double dildos

My first video as a slutty sissy

1:34

3 years ago xHamster

My first video as a slutty sissy

Camp Sissy Boi Presents CEI For First Timers

5:24

3 years ago xHamster

Camp Sissy Boi Presents CEI For First Timers

First-Ever Time No Palms Jism Uncircumcised Sausage

4:22

2 years ago Gay Ck

First-Ever Time No Palms Jism Uncircumcised Sausage

First ride in new tiny chastity (nub)

8:40

2 years ago xHamster

First ride in new tiny chastity (nub)

Alxtoyboys First try with his new fist dildo

7:02

2 years ago xHamster

Alxtoyboys First try with his new fist dildo

First Video: Anal Dildoriding

2:04

2 years ago xHamster

First Video: Anal Dildoriding

My first time dressed as a sissy feels incredible

15:47

2 years ago xHamster

My first time dressed as a sissy feels incredible

My first anal play video.

1:25

2 years ago xHamster

My first anal play video.

Sissy Pauline first crossdresser experience

2:12

2 years ago xHamster

Sissy Pauline first crossdresser experience

First-Timer Femboy rails fucktoy while locked up

3:38

2 years ago Gay Ck

First-Timer Femboy rails fucktoy while locked up

First Time fuck machine anal sex

1:27

2 years ago xHamster

First Time fuck machine anal sex

First Time Sperm Donor Caught on Camera

2:28

2 years ago xHamster

First Time Sperm Donor Caught on Camera

Amateur sissy first time riding her dildo

4:11

2 years ago xHamster

Amateur sissy first time riding her dildo

First Time Sissy Slut WEBCam Show

17:22

2 years ago xHamster

First Time Sissy Slut WEBCam Show

Denzel James rides 10 inch dildo first time ass fuck in bedroom

12:52

2 years ago xHamster

Denzel James rides 10 inch dildo first time ass fuck in bedroom

PRETTY BRUNETTE TRIES DOUBLE ANAL PENETRATION FOR FIRST TIME

0:13

2 years ago xHamster

PRETTY BRUNETTE TRIES DOUBLE ANAL PENETRATION FOR FIRST TIME

Femboy CD riding my first dildo ever in skirt and stockings

3:44

2 years ago xHamster

Femboy CD riding my first dildo ever in skirt and stockings

Twerkusxxx: First 10 minutes of something special

10:02

2 years ago xHamster

Twerkusxxx: First 10 minutes of something special

Femboy: My very first PornHub flick

5:53

2 years ago Gay Ck

Femboy: My very first PornHub flick

A depraved gentle student learns for the first time with daddy a masturbation and gets portions of powerful sperm!

5:27

2 years ago xHamster

A depraved gentle student learns for the first time with daddy a masturbation and gets portions of powerful sperm!

First full length clip, pee , playing , crossdressing sissy

8:54

2 years ago xHamster

First full length clip, pee , playing , crossdressing sissy

asian trap first-timer ass-fuck faux-cock joy 02

4:11

2 years ago Gay Ck

Asian trap first-timer ass-fuck faux-cock joy 02

First 2022 LOCKTOBER cum!!!

0:41

2 years ago xHamster

First 2022 LOCKTOBER cum!!!

First-Ever Rail On Plow Machine

8:58

2 years ago Gay Ck

First-Ever Rail On Plow Machine

Black sissy boy. My first video after losing some weight

0:36

2 years ago xHamster

Black sissy boy. My first video after losing some weight

Fucking my boyfriend's cute virgin ass for the first time

6:36

2 years ago xHamster

Fucking my boyfriend's cute virgin ass for the first time

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