Search results - First Crossdresser

Total found: 1015 videos (page 3)

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Straight guy dresses for first time

1:47

4 years ago xHamster

Straight guy dresses for first time

Nude crossdresser first fist

3:11

4 years ago xHamster

Nude crossdresser first fist

First real public outdoor nylons

1:05

4 years ago xHamster

First real public outdoor nylons

Sissies first anal beads

0:10

4 years ago xHamster

Sissies first anal beads

My first ever monster dildo

1:10

4 years ago xHamster

My first ever monster dildo

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 fucked from behind, her first big white cock

12:29

4 years ago xHamster

Sissy fucked from behind, her first big white cock

First Ever Bareback

0:47

4 years ago xHamster

First Ever Bareback

I want my first big cock!!

0:42

4 years ago xHamster

I want my first big cock!!

I shine my latex for the first time

2:09

4 years ago xHamster

I shine my latex for the first time

Young skater virgin cums inside for the first time anon

3:23

4 years ago xHamster

Young skater virgin cums inside for the first time anon

First time ever meeting someone from online

2:08

4 years ago xHamster

First time ever meeting someone from online

Schoolboy first time jerking off on porn in class - cumshot,

5:23

4 years ago xHamster

Schoolboy first time jerking off on porn in class - cumshot,

Me as Clown meets squirting dildo for first time

1:00

4 years ago xHamster

Me as Clown meets squirting dildo for first time

My First Dildo Ride

5:02

4 years ago xHamster

My First Dildo Ride

First Person View

2:31

4 years ago xHamster

First Person View

First anal for my second man, I fucked him

0:46

4 years ago xHamster

First anal for my second man, I fucked him

First dildo fuck. I hope you like

0:52

4 years ago xHamster

First dildo fuck. I hope you like

Bought and used my first dildo

1:26

4 years ago xHamster

Bought and used my first dildo

My very first video

0:48

4 years ago xHamster

My very first video

Your first time as a sissy will be amazing

16:28

4 years ago xHamster

Your first time as a sissy will be amazing

0:13

4 years ago xHamster

My first vedio

my first day with the new toy.. i'm going to ruin my asshole

2:09

4 years ago xHamster

My first day with the new toy.. i'm going to ruin my asshole

MY FIRST BEST VIDEO

0:41

4 years ago xHamster

MY FIRST BEST VIDEO

Sissy Lexi tries out her first dildo part 2

1:02

4 years ago xHamster

Sissy Lexi tries out her first dildo part 2

Sissy Lexi tries out her first dildo part 1

0:33

4 years ago xHamster

Sissy Lexi tries out her first dildo part 1

MY First Time Bikini Dress

1:15

4 years ago xHamster

MY First Time Bikini Dress

Virgin Bottom Uses Dildo For First Time

1:14

4 years ago xHamster

Virgin Bottom Uses Dildo For First Time

First Time Nadi me Nahate huye

1:07

4 years ago xHamster

First Time Nadi me Nahate huye

Exploring my ass for the first time.

1:43

4 years ago xHamster

Exploring my ass for the first time.

Mexican CROSSdresser having first Sissygasm From Sex

1:05

4 years ago xHamster

Mexican CROSSdresser having first Sissygasm From Sex

Crossdresser fucked by cucumber dildo (First time ANAL)

12:41

4 years ago xHamster

Crossdresser fucked by cucumber dildo (First time ANAL)

My First video! Prince Albert, Riding a Bad dragon

4:34

4 years ago xHamster

My First video! Prince Albert, Riding a Bad dragon

My first time as a sissy feels so right

17:55

4 years ago xHamster

My first time as a sissy feels so right

My first attempt at milking

7:18

4 years ago xHamster

My first attempt at milking

sissy fucked from behind, her first big arab cock

1:02

3 years ago xHamster

Sissy fucked from behind, her first big arab cock

Crossdresser first ass pumping

6:10

3 years ago xHamster

Crossdresser first ass pumping

My first Crossdresser relationship

0:35

3 years ago xHamster

My first Crossdresser relationship

My very first homemade video

0:59

3 years ago xHamster

My very first homemade video

First time making ass clap and twerking

0:53

3 years ago xHamster

First time making ass clap and twerking

My first time trying to twerk

0:53

3 years ago xHamster

My first time trying to twerk

Louboutin peep toes first cum

7:14

3 years ago xHamster

Louboutin peep toes first cum

My first dildo ride - zoe sixxx

1:04

3 years ago xHamster

My first dildo ride - zoe sixxx

Angel jules x - Femboy Angel Jules first Time

6:59

3 years ago xHamster

Angel jules x - Femboy Angel Jules first Time

ryan743 first live webcam recorded

6:16

3 years ago xHamster

Ryan743 first live webcam recorded

2:50

3 years ago xHamster

My first video

A little peek first video

0:26

3 years ago xHamster

A little peek first video

0:48

3 years ago xHamster

First Video

0:12

3 years ago xHamster

My first time

You get to witness my first time crossdressing

10:57

3 years ago xHamster

You get to witness my first time crossdressing

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 solo video

2:13

3 years ago xHamster

First solo video

First ride on sex machine and big dildo

1:48

3 years ago xHamster

First ride on sex machine and big dildo

1:34

3 years ago xHamster

First Video

My first time in New nylons in quite some time

1:19

3 years ago xHamster

My first time in New nylons in quite some time

Trying my friend's (40 mm) anal plug for the first time

1:18

3 years ago xHamster

Trying my friend's (40 mm) anal plug for the first time

First I have to put on my makeup

13:56

3 years ago xHamster

First I have to put on my makeup

Crossdressing Sissy Selfie, solo, first time taping

1:04

3 years ago xHamster

Crossdressing Sissy Selfie, solo, first time taping

my ass and asshole first half

13:46

3 years ago xHamster

My ass and asshole first half

First anal fisting by Belladonnas bitch fist dildo

1:09

3 years ago xHamster

First anal fisting by Belladonnas bitch fist dildo

Self Fist Fucked for teh first time

6:10

3 years ago xHamster

Self Fist Fucked for teh first time

Timid French Sissy First-Ever Time To Deepthroat

5:52

3 years ago Gay Ck

Timid French Sissy First-Ever Time To Deepthroat

CD sucks her first cock

8:28

4 years ago Gay Ck

CD sucks her first cock

Sissy Crossdresser double orgasm first solo dildo ride 3

2:19

4 years ago Gay Ck

Sissy Crossdresser double orgasm first solo dildo ride 3

Tasty First-Timer Japanese Trap DEEP THROAT

9:57

4 years ago Gay Ck

Tasty First-Timer Japanese Trap DEEP THROAT

Bashful French sissy first-ever time to blow

5:54

4 years ago Gay Ck

Bashful French sissy first-ever time to blow

Young Bbw crossdresser first Black Cock # 2 video 3

2:49

4 years ago Gay Ck

Young Bbw crossdresser first Black Cock # 2 video 3

Crossdresser Amber Sucks her first BBC. part 1

9:48

4 years ago Gay Ck

Crossdresser Amber Sucks her first BBC. part 1

Sissy Breanne's first blowjob and BBC

4:25

4 years ago Gay Ck

Sissy Breanne's first blowjob and BBC

Sissy Breanne's first blowjob and BBC 3

4:20

4 years ago Gay Ck

Sissy Breanne's first blowjob and BBC 3

First-Ever Day with a fresh Fucktoy five Long Vid

4:35

4 years ago Gay Ck

First-Ever Day with a fresh Fucktoy five Long Vid

First-Timer Japanese CDs CIM blow-job

8:21

3 years ago Gay Ck

First-Timer Japanese CDs CIM blow-job

Crossdresser Amber Sucks her first BBC. part 1 4

9:44

3 years ago Gay Ck

Crossdresser Amber Sucks her first BBC. part 1 4

CD Fucks First Timer

8:26

4 years ago Gay Ck

CD Fucks First Timer

Heather's first BBC 3

10:27

3 years ago Gay Ck

Heather's first BBC 3

First-Timer Bodybuilder vs Faggyboi Jail Sissy

3:52

4 years ago Gay Ck

First-Timer Bodybuilder vs Faggyboi Jail Sissy

Sissy Breanne's first blowjob and BBC 2

4:22

4 years ago Gay Ck

Sissy Breanne's first blowjob and BBC 2

Vintage first time anal 2

2:42

4 years ago Gay Ck

Vintage first time anal 2

Crossdresser Amber Deepthroats her first-ever BIG BLACK COCK part 1 (Thick Dark-Hued)

9:48

4 years ago Gay Ck

Crossdresser Amber Deepthroats her first-ever BIG BLACK COCK part 1 (Thick Dark-Hued)

Luna takes her first cock 2

3:42

4 years ago Gay Ck

Luna takes her first cock 2

Heathers very first BIG BLACK COCK

10:27

3 years ago Gay Ck

Heathers very first BIG BLACK COCK

4:56

4 years ago Gay Ck

First Video 3

White-Hot Buttfuck Have Fun, with Adorable Gape (first-ever Upload)

10:17

4 years ago Gay Ck

White-Hot Buttfuck Have Fun, with Adorable Gape (first-ever Upload)

Danish crossdressers first-ever time oral job ended with ass fucking

8:39

3 years ago Gay Ck

Danish crossdressers first-ever time oral job ended with ass fucking

First-Timer Crossdresser Deep-Throats Gets Inhaled

6:38

4 years ago Gay Ck

First-Timer Crossdresser Deep-Throats Gets Inhaled

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

Vintage first time anal

2:43

4 years ago Gay Ck

Vintage first time anal

Bashful French Sissy First-Ever Time To Deepthroat

5:52

3 years ago Gay Ck

Bashful French Sissy First-Ever Time To Deepthroat

Young Bbw crossdresser first Black Cock # 2 video

2:52

4 years ago Gay Ck

Young Bbw crossdresser first Black Cock # 2 video

barely legal Yr Senior Twunks very first Ass-Fuck Climax!

6:25

3 years ago Gay Ck

Barely legal Yr Senior Twunks very first Ass-Fuck Climax!

Robin Quinn femboy first time with fleshlight

2:19

4 years ago Gay Ck

Robin Quinn femboy first time with fleshlight

Vintage first time anal 3

2:40

3 years ago Gay Ck

Vintage first time anal 3

My first fucking video

10:15

4 years ago Gay Ck

My first fucking video

Crossdresser Amber Sucks her first BBC. part 1 3

9:48

3 years ago Gay Ck

Crossdresser Amber Sucks her first BBC. part 1 3

First-Timer PLUMPER Trap

8:43

3 years ago Gay Ck

First-Timer PLUMPER Trap

His first time - no virgin anymore 3

2:08

4 years ago Gay Ck

His first time - no virgin anymore 3

pleasures very first sucky-sucky of the night

2:47

6 years ago Gay Ck

Pleasures very first sucky-sucky of the night

Sissy Crossdresser double orgasm first solo dildo ride 2

2:20

4 years ago Gay Ck

Sissy Crossdresser double orgasm first solo dildo ride 2

My first fucking video 2

10:14

4 years ago Gay Ck

My first fucking video 2

Bashful French sissy first-ever time to gargle

5:52

4 years ago Gay Ck

Bashful French sissy first-ever time to gargle

Sissy Crossdresser double orgasm first solo dildo ride 6

2:17

3 years ago Gay Ck

Sissy Crossdresser double orgasm first solo dildo ride 6

Luna takes her first cock

3:39

4 years ago Gay Ck

Luna takes her first cock

FEMBOY FIRST-EVER TIME RAILING ten INCH FAKE PENIS ! *cums Twice* - Wondermori

4:38

3 years ago Gay Ck

FEMBOY FIRST-EVER TIME RAILING ten INCH FAKE PENIS ! cums Twice - Wondermori

My first-ever time at my fresh glory crevasse

5:58

4 years ago Gay Ck

My first-ever time at my fresh glory crevasse

CD sucks her first cock 2

8:25

4 years ago Gay Ck

CD sucks her first cock 2

My first-ever Movie, some Ass Fucking Have Fun in a Uber-Cute Fuck-Hole

3:58

4 years ago Gay Ck

My first-ever Movie, some Ass Fucking Have Fun in a Uber-Cute Fuck-Hole

Sissy Crossdresser double orgasm first solo dildo ride 5

2:19

3 years ago Gay Ck

Sissy Crossdresser double orgasm first solo dildo ride 5

First-Timer Eyes Covered, Gaged and Greased made to Jizz *music*

5:23

4 years ago Gay Ck

First-Timer Eyes Covered, Gaged and Greased made to Jizz music

Sissy Breannes first-ever suck off and BIG BLACK COCK

4:20

4 years ago Gay Ck

Sissy Breannes first-ever suck off and BIG BLACK COCK

Sissy Crossdresser double orgasm first solo dildo ride 4

2:16

4 years ago Gay Ck

Sissy Crossdresser double orgasm first solo dildo ride 4

Danish crossdressers very first time dt concluded with ass fucking

8:39

4 years ago Gay Ck

Danish crossdressers very first time dt concluded with ass fucking

4:56

4 years ago Gay Ck

First Video

CD Fucks First Timer 2

8:25

4 years ago Gay Ck

CD Fucks First Timer 2

Sissy Enjoy - Dressin Up First-Timer crossdresser PMV

5:49

4 years ago Gay Ck

Sissy Enjoy - Dressin Up First-Timer crossdresser PMV

Stud Puts on Stocking and Masturbates off for the very first Time

8:26

4 years ago Gay Ck

Stud Puts on Stocking and Masturbates off for the very first Time

Heather's first BBC

10:27

4 years ago Gay Ck

Heather's first BBC

First-Timer - two CDs Frictation Deepthroat Penetrate - Massive Jism

16:32

4 years ago Gay Ck

First-Timer - two CDs Frictation Deepthroat Penetrate - Massive Jism

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