Search results - First Crossdresser

Total found: 1015 videos (page 2)

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First piss of the night

0:52

5 years ago xHamster

First piss of the night

First ever video

0:18

5 years ago xHamster

First ever video

First cum on screen

2:02

5 years ago xHamster

First cum on screen

Sissy take dildo first time in video

7:02

5 years ago xHamster

Sissy take dildo first time in video

0:44

5 years ago xHamster

My first video

First time as cd

0:14

5 years ago xHamster

First time as cd

First Dickson then I.P.

1:34

5 years ago xHamster

First Dickson then I.P.

first try stallion dick toy

1:01

5 years ago xHamster

First try stallion dick toy

Spankboy69 first time DP

0:53

5 years ago xHamster

Spankboy69 first time DP

first time riding a dildo

2:46

5 years ago xHamster

First time riding a dildo

first video cum with buttplug

1:35

5 years ago xHamster

First video cum with buttplug

JOANNE SLAM - 2020 FIRST CUMBACK VIDEO!!!

11:05

5 years ago xHamster

JOANNE SLAM - 2020 FIRST CUMBACK VIDEO!!!

Crossdressing sissy femboy first time

0:37

5 years ago xHamster

Crossdressing sissy femboy first time

1 First Friday night at home

20:01

5 years ago xHamster

1 First Friday night at home

First Cum in Video

4:05

5 years ago xHamster

First Cum in Video

0:11

5 years ago xHamster

My first movie

First time balls deep HUGE BBC dildos

1:53

5 years ago xHamster

First time balls deep HUGE BBC dildos

Tranny First time Anal

0:31

5 years ago xHamster

Tranny First time Anal

My first panty wetting video

1:18

5 years ago xHamster

My first panty wetting video

3:03

5 years ago xHamster

My first video

My first dildo ride

2:00

5 years ago xHamster

My first dildo ride

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)

Old movie of me with Rocco & first pee

7:32

5 years ago xHamster

Old movie of me with Rocco & first pee

Sissy Jen's first BBC latex hood suck

1:06

5 years ago xHamster

Sissy Jen's first BBC latex hood suck

My first multiple creampie

0:25

5 years ago xHamster

My first multiple creampie

QOS first xhamster bbc dildo vid

3:24

5 years ago xHamster

QOS first xhamster bbc dildo vid

My first ever video

0:35

5 years ago xHamster

My first ever video

First session with Antonio

23:06

5 years ago xHamster

First session with Antonio

Preparing the first meeting with Angel

16:21

5 years ago xHamster

Preparing the first meeting with Angel

my first video with a wand cumming

0:25

5 years ago xHamster

My first video with a wand cumming

My first recording of cumming in bra and panties

0:47

5 years ago xHamster

My first recording of cumming in bra and panties

my first time with a vibrating finger and in sexy women's cl

0:20

5 years ago xHamster

My first time with a vibrating finger and in sexy women's cl

3:04

5 years ago xHamster

My first video

German Amateur Sissy CD gets her first Fuck

1:06

5 years ago xHamster

German Amateur Sissy CD gets her first Fuck

First Time To Cum In Moms Panties

0:30

5 years ago xHamster

First Time To Cum In Moms Panties

First try out of new 14 inch Dildo

15:15

5 years ago xHamster

First try out of new 14 inch Dildo

0:24

5 years ago xHamster

My first video

first time sissy crossdress with dildos

28:23

5 years ago xHamster

First time sissy crossdress with dildos

Virgin sissy fucks ass for the first time

0:16

5 years ago xHamster

Virgin sissy fucks ass for the first time

First time getting larger butt plug all the way in!

1:53

5 years ago xHamster

First time getting larger butt plug all the way in!

Sonya's First Visit - The Armchair

4:57

4 years ago xHamster

Sonya's First Visit - The Armchair

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.

First Time with DADDY

1:46

4 years ago xHamster

First Time with DADDY

15.07.2020 first Chastity

2:34

4 years ago xHamster

15.07.2020 first Chastity

My first video with a toy

0:35

4 years ago xHamster

My first video with a toy

First time with a wig! Straight bottom loves it

39:31

4 years ago xHamster

First time with a wig! Straight bottom loves it

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

1:27

4 years ago xHamster

First Dildoe

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

Very excited with my new dress and my first pair of shoes

2:44

4 years ago xHamster

Very excited with my new dress and my first pair of shoes

My first from the 90er

2:02

4 years ago xHamster

My first from the 90er

Me fisting a friend for the first time

2:10

4 years ago xHamster

Me fisting a friend for the first time

1:27

4 years ago xHamster

First try

First time filming myself using a dildo

1:48

4 years ago xHamster

First time filming myself using a dildo

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

0:45

4 years ago xHamster

First anal

8:33

4 years ago xHamster

My first video

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

My first load of cum deposited inside me

0:45

4 years ago xHamster

My first load of cum deposited inside me

my first creampie

0:22

4 years ago xHamster

My first creampie

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)

First try with my double cock dildo (17 Nov 2020)

3:16

4 years ago xHamster

First try with my double cock dildo (17 Nov 2020)

First Video To Be Continued...

0:45

4 years ago xHamster

First Video To Be Continued...

My First Video - 2007

1:15

4 years ago xHamster

My First Video - 2007

First time Anal fisting best ever

2:04

4 years ago xHamster

First time Anal fisting best ever

0:09

4 years ago xHamster

First step

Young CD first anal

0:15

4 years ago xHamster

Young CD first anal

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

Mi primer video my first video

0:53

4 years ago xHamster

Mi primer video my first video

0:36

4 years ago xHamster

My First

First time on camera

0:20

4 years ago xHamster

First time on camera

first dildo riding

1:22

4 years ago xHamster

First dildo riding

First time straight latino fucks Crossdresser

4:31

4 years ago xHamster

First time straight latino fucks Crossdresser

First Hands free cum on cam

10:41

4 years ago xHamster

First Hands free cum on cam

WAD Sentry - First try

1:47

4 years ago xHamster

WAD Sentry - First try

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

Pipedream King Cock 14inch - First insertion with huge dildo

4:25

4 years ago xHamster

Pipedream King Cock 14inch - First insertion with huge dildo

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!

First time with a bbc

0:18

4 years ago xHamster

First time with a bbc

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

Straight guy first CD

1:08

4 years ago xHamster

Straight guy first CD

Straight Guy first BJ from a CD

0:34

4 years ago xHamster

Straight Guy first BJ from a CD

1:18

4 years ago xHamster

First time

This is my first time crossdressing like this

15:38

4 years ago xHamster

This is my first time crossdressing like this

young cute stud is being crossdressed for the first time

2:21

4 years ago xHamster

Young cute stud is being crossdressed for the first time

Tylerina & Mason's first video

29:31

4 years ago xHamster

Tylerina & Mason's first video

Sissy Bi Curious First Time Ruined Orgasm

0:47

4 years ago xHamster

Sissy Bi Curious First Time Ruined Orgasm

Gigantic dildo for the first time

1:40

4 years ago xHamster

Gigantic dildo for the first time

First crossdressing video

0:25

4 years ago xHamster

First crossdressing video

Susana's first public video.

2:34

4 years ago xHamster

Susana's first public video.

Crossdresser playing with her cock like it's her first time

4:25

4 years ago xHamster

Crossdresser playing with her cock like it's her first time

He Did Kiss Me First!

5:41

4 years ago xHamster

He Did Kiss Me First!

My first and i love it

1:22

4 years ago xHamster

My first and i love it

My first fistigsation

1:00

4 years ago xHamster

My first fistigsation

Test in pantyhose. First video

0:26

4 years ago xHamster

Test in pantyhose. First video

Crossdress first time sex

1:21

4 years ago xHamster

Crossdress first time sex

First time riding dildo in chastity.

1:50

4 years ago xHamster

First time riding dildo in chastity.

First time ass fucking myself

0:41

4 years ago xHamster

First time ass fucking myself

My first video.

3:51

4 years ago xHamster

My first video.

This is my first time crossdressing

16:46

4 years ago xHamster

This is my first time crossdressing

0:18

4 years ago xHamster

First

Crossdressed first time blowjob

1:15

4 years ago xHamster

Crossdressed first time blowjob

My first video(I hope you will like it

2:44

4 years ago xHamster

My first video(I hope you will like it

First Interview

6:22

4 years ago xHamster

First Interview

My first time crossdressing was so hot

15:41

4 years ago xHamster

My first time crossdressing was so hot

First time in chastity

0:10

4 years ago xHamster

First time in chastity

This will be my first sissy crossdressing adventure

15:29

4 years ago xHamster

This will be my first sissy crossdressing adventure

6:39

4 years ago xHamster

My first time

First crossdressing ejaculation

0:38

4 years ago xHamster

First crossdressing ejaculation

My first ever Estim

0:44

4 years ago xHamster

My first ever Estim

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