Search results - First Time Crossdresser

Total found: 409 videos

1
2
3
4
next

My first time in New nylons in quite some time

1:19

2 years ago xHamster

My first time in New nylons in quite some time

Two Friends did sex at first time, They both got felicity and orgasm at the same time

6:07

17 days ago xHamster

Two Friends did sex at first time, They both got felicity and orgasm at the same time

First time Hung Latino fucks his first CD Hole

11:06

3 years ago xHamster

First time Hung Latino fucks his first CD Hole

18-year-old Virgin Twink ejaculates for the first time, First masturbation (xblue18)

3:07

2 years ago xHamster

18-year-old Virgin Twink ejaculates for the first time, First masturbation (xblue18)

I am crossdressing for the first time and its amazing

14:06

6 years ago xHamster

I am crossdressing for the first time and its amazing

First time crossdressing

1:23

6 years ago xHamster

First time crossdressing

This is my first time being photographed while crossdressing

14:57

6 years ago xHamster

This is my first time being photographed while crossdressing

Sissy Crossdressers First Time Anal

3:18

6 years ago xHamster

Sissy Crossdressers First Time Anal

norma first time crossdressing

2:49

6 years ago xHamster

Norma first time crossdressing

Crossdress Tanya First Time With a Cucumber 8 inches thick

7:30

6 years ago xHamster

Crossdress Tanya First Time With a Cucumber 8 inches thick

BIG BLACK COCK GETTING SOME ORAL SERVICE FROM FIRST TIME CD

9:10

6 years ago xHamster

BIG BLACK COCK GETTING SOME ORAL SERVICE FROM FIRST TIME CD

My first time as a sissy was so liberating

15:00

6 years ago xHamster

My first time as a sissy was so liberating

His first time with a shemale top

4:20

6 years ago xHamster

His first time with a shemale top

Archive 6: 08-01-17 First time I'd worn a dress or heels.

5:00

6 years ago xHamster

Archive 6: 08-01-17 First time I'd worn a dress or heels.

This is my first time as a crossdressing sissy

15:02

6 years ago xHamster

This is my first time as a crossdressing sissy

This is my first time crossdressing for real

13:56

6 years ago xHamster

This is my first time crossdressing for real

First time becoming Lisa Lust

0:30

6 years ago xHamster

First time becoming Lisa Lust

First time sucking a t girls cock

1:03

6 years ago xHamster

First time sucking a t girls cock

I am crossdressing for the first time and its amazing

13:03

5 years ago xHamster

I am crossdressing for the first time and its amazing

Self fed cum first time eating

0:53

5 years ago xHamster

Self fed cum first time eating

Big dildo fits first time in the Crossdressers ass

2:58

5 years ago xHamster

Big dildo fits first time in the Crossdressers ass

Anal plug lilys first time on tape

4:30

5 years ago xHamster

Anal plug lilys first time on tape

Riding for the first time

2:36

5 years ago xHamster

Riding for the first time

My first time at my new glory hole

5:48

5 years ago xHamster

My first time at my new glory hole

First time fucking a white sissy

8:24

5 years ago xHamster

First time fucking a white sissy

CD Susy first time ride dick and cum

3:22

5 years ago xHamster

CD Susy first time ride dick and cum

Fucking my ass for the first time

2:51

5 years ago xHamster

Fucking my ass for the first time

Mallory first time real play sissy trans anal ass toys trans

0:49

5 years ago xHamster

Mallory first time real play sissy trans anal ass toys trans

First time for a crossdresser

2:05

4 years ago xHamster

First time for a crossdresser

First time for a crossdresser,

1:17

4 years ago xHamster

First time for a crossdresser,

First video summer time!

3:34

4 years ago xHamster

First video summer time!

I got fucked by a first time crossdresser

4:40

4 years ago xHamster

I got fucked by a first time crossdresser

FIRST TIME ON TOP OF HIM FELLING SO GOOD

4:57

4 years ago xHamster

FIRST TIME ON TOP OF HIM FELLING SO GOOD

Cross dress first time fuck big dildo in bathroom

1:01

4 years ago xHamster

Cross dress first time fuck big dildo in bathroom

My first time crossdressing was so hot

13:56

4 years ago xHamster

My first time crossdressing was so hot

Suleika fuck Alischa first time

2:20

4 years ago xHamster

Suleika fuck Alischa first time

First time for toy

1:15

4 years ago xHamster

First time for toy

Closet cd Natcd enjoying dildo for first time

1:28

4 years ago xHamster

Closet cd Natcd enjoying dildo for first time

My thin Asian crossdressers for his first time

3:35

4 years ago Boy Friend TV

My thin Asian crossdressers for his first time

Croatian Crossdresser first time out and smoking.

6:10

4 years ago xHamster

Croatian Crossdresser first time out and smoking.

First time crossdress JK uniform pantyhose cum (reupload)

16:57

4 years ago xHamster

First time crossdress JK uniform pantyhose cum (reupload)

The first time here.

1:23

4 years ago xHamster

The first time here.

First Time Really Taking it Deep from my Dildos

2:05

4 years ago xHamster

First Time Really Taking it Deep from my Dildos

First Time Really Taking it Deep from my Dildos 02

3:00

4 years ago xHamster

First Time Really Taking it Deep from my Dildos 02

First Time Taking it Deep from my Dildos 03

5:03

4 years ago xHamster

First Time Taking it Deep from my Dildos 03

0:42

4 years ago xHamster

First time

First time in the ass for a slave

4:02

4 years ago xHamster

First time in the ass for a slave

Japanese gay's first time crossdress near the highway

4:24

4 years ago xHamster

Japanese gay's first time crossdress near the highway

My first time at my new glory hole

5:56

4 years ago Boy Friend TV

My first time at my new glory hole

Sissy take dildo first time in video

7:02

4 years ago xHamster

Sissy take dildo first time in video

First time as cd

0:14

4 years ago xHamster

First time as cd

Spankboy69 first time DP

0:53

4 years ago xHamster

Spankboy69 first time DP

first time riding a dildo

2:46

4 years ago xHamster

First time riding a dildo

I am trying cross dressing for the first time

11:52

4 years ago Boy Friend TV

I am trying cross dressing for the first time

Crossdressing sissy femboy first time

0:37

4 years ago xHamster

Crossdressing sissy femboy first time

My first time dressing up like a sissy was amazing

10:38

4 years ago Boy Friend TV

My first time dressing up like a sissy was amazing

First Time on Fucking Machine in Thigh High Socks

4:18

4 years ago Boy Friend TV

First Time on Fucking Machine in Thigh High Socks

First time balls deep HUGE BBC dildos

1:53

4 years ago xHamster

First time balls deep HUGE BBC dildos

Tranny First time Anal

0:31

4 years ago xHamster

Tranny First time Anal

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

0:20

3 years ago xHamster

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

First Time To Cum In Moms Panties

0:30

3 years ago xHamster

First Time To Cum In Moms Panties

first time sissy crossdress with dildos

28:23

3 years ago xHamster

First time sissy crossdress with dildos

Virgin sissy fucks ass for the first time

0:16

3 years ago xHamster

Virgin sissy fucks ass for the first time

First time getting larger butt plug all the way in!

1:53

3 years ago xHamster

First time getting larger butt plug all the way in!

First Time with DADDY

1:46

3 years ago xHamster

First Time with DADDY

First time with a wig! Straight bottom loves it

39:31

3 years ago xHamster

First time with a wig! Straight bottom loves it

Danish crossdresser's first time blowjob, finished with anal

8:39

3 years ago Boy Friend TV

Danish crossdresser's first time blowjob, finished with anal

Toy in virgin ass for first time

0:58

3 years ago xHamster

Toy in virgin ass for first time

Me fisting a friend for the first time

2:10

3 years ago xHamster

Me fisting a friend for the first time

First time filming myself using a dildo

1:48

3 years ago xHamster

First time filming myself using a dildo

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

16:02

3 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

3 years ago xHamster

This is my first time dressing like a sissy

First time fucking a white sissy

8:34

3 years ago Boy Friend TV

First time fucking a white sissy

Sissy first time 7 inch Dildo

1:47

3 years ago xHamster

Sissy first time 7 inch Dildo

Genuine first time anal and using a dildo (Curious)

1:12

3 years ago xHamster

Genuine first time anal and using a dildo (Curious)

First time Anal fisting best ever

2:04

3 years ago xHamster

First time Anal fisting best ever

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

2:08

3 years ago xHamster

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

First time on camera

0:20

3 years ago xHamster

First time on camera

crossdressers first time

8:50

3 years ago Boy Friend TV

Crossdressers first time

First time straight latino fucks Crossdresser

4:31

3 years ago xHamster

First time straight latino fucks Crossdresser

crossdressers first time

8:49

3 years ago Boy Friend TV

Crossdressers first time

First time my sissy pussy was fucked

0:31

3 years ago xHamster

First time my sissy pussy was fucked

First Time in Chastity

3:37

3 years ago xHamster

First Time in Chastity

Sissyjen1 gets fucked and sucks cock for the first time!

5:24

3 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

3 years ago xHamster

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

First time with a bbc

0:18

3 years ago xHamster

First time with a bbc

1:18

3 years ago xHamster

First time

This is my first time crossdressing like this

15:38

3 years ago xHamster

This is my first time crossdressing like this

This is my first time crossdressing like this

15:30

3 years ago Boy Friend TV

This is my first time crossdressing like this

young cute stud is being crossdressed for the first time

2:21

3 years ago xHamster

Young cute stud is being crossdressed for the first time

Sissy Bi Curious First Time Ruined Orgasm

0:47

3 years ago xHamster

Sissy Bi Curious First Time Ruined Orgasm

Gigantic dildo for the first time

1:40

3 years ago xHamster

Gigantic dildo for the first time

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

4:25

3 years ago xHamster

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

Shy French sissy first time to suck

5:51

3 years ago Boy Friend TV

Shy French sissy first time to suck

Crossdress first time sex

1:21

3 years ago xHamster

Crossdress first time sex

First time riding dildo in chastity.

1:50

3 years ago xHamster

First time riding dildo in chastity.

First time ass fucking myself

0:41

3 years ago xHamster

First time ass fucking myself

This is my first time crossdressing

16:46

3 years ago xHamster

This is my first time crossdressing

Crossdressed first time blowjob

1:15

3 years ago xHamster

Crossdressed first time blowjob

My first time crossdressing was so hot

15:41

3 years ago xHamster

My first time crossdressing was so hot

First time in chastity

0:10

3 years ago xHamster

First time in chastity

6:39

3 years ago xHamster

My first time

Straight guy dresses for first time

1:47

3 years ago xHamster

Straight guy dresses for first time

Sissy Crossdresser Slut fucked for first time

1:00

3 years ago xHamster

Sissy Crossdresser Slut fucked for first time

I shine my latex for the first time

2:09

3 years ago xHamster

I shine my latex for the first time

Young skater virgin cums inside for the first time anon

3:23

3 years ago xHamster

Young skater virgin cums inside for the first time anon

First time ever meeting someone from online

2:08

2 years ago xHamster

First time ever meeting someone from online

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

5:23

2 years ago xHamster

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

Me as Clown meets squirting dildo for first time

1:00

2 years ago xHamster

Me as Clown meets squirting dildo for first time

Your first time as a sissy will be amazing

16:28

2 years ago xHamster

Your first time as a sissy will be amazing

MY First Time Bikini Dress

1:15

2 years ago xHamster

MY First Time Bikini Dress

First Time Nadi me Nahate huye

1:07

2 years ago xHamster

First Time Nadi me Nahate huye

Virgin Bottom Uses Dildo For First Time

1:14

2 years ago xHamster

Virgin Bottom Uses Dildo For First Time

Exploring my ass for the first time.

1:43

2 years ago xHamster

Exploring my ass for the first time.

Crossdresser fucked by cucumber dildo (First time ANAL)

12:41

2 years ago xHamster

Crossdresser fucked by cucumber dildo (First time ANAL)

My first time as a sissy feels so right

17:55

2 years ago xHamster

My first time as a sissy feels so right

STR8 GUYS FIRST TIME... Found me on Grindr in Denver

7:25

2 years ago xHamster

STR8 GUYS FIRST TIME... Found me on Grindr in Denver

First time making ass clap and twerking

0:53

2 years ago xHamster

First time making ass clap and twerking

My first time trying to twerk

0:53

2 years ago xHamster

My first time trying to twerk

Angel jules x - Femboy Angel Jules first Time

6:59

2 years ago xHamster

Angel jules x - Femboy Angel Jules first Time

1
2
3
4
next

Recommended