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Roleplay: 118 Movies, sorted by Popularity

Crossdressing couple loves roleplaying and sex

Crossdressing couple loves roleplaying and sex

12:20
Big Dick Bitch presents ROLE PLAY 4 Dvd

Big Dick Bitch presents ROLE PLAY 4 Dvd

03:18
Lazy maid gets anal abuse for not cleaning with dirty talking abuse

Lazy maid gets anal abuse for not cleaning with dirty talking abuse

07:23
Transsexual Heartbreakers 14 - Scene 4

Transsexual Heartbreakers 14 - Scene 4

17:45
fox love wolf yiff

fox love wolf yiff

13:46
Haunted Hotel Room TS Fuck

Haunted Hotel Room TS Fuck

05:06
Russian Crossdress Roleplayers

Russian Crossdress Roleplayers

40:42
Mr 18 Freaky Adventures - Scene 1

Mr 18 Freaky Adventures - Scene 1

15:22
androgino

androgino

08:29
Hes My Girl - Scene 4

Hes My Girl - Scene 4

22:32
Sexy BBW Nurse Tanya Mellow Sucking and riding

Sexy BBW Nurse Tanya Mellow Sucking and riding

09:04
Shemales Really Loves Role Playing

Shemales Really Loves Role Playing

10:08
Couple Shemale Sucking and Role Play

Couple Shemale Sucking and Role Play

10:08
Hentai femboy sissy joi, femboy crossdresser joi

Hentai femboy sissy joi, femboy crossdresser joi

10:06
Natalie Mars, Goddess Tangent & Jasmine Mendez and strapon

Natalie Mars, Goddess Tangent & Jasmine Mendez and strapon

17:09
Doctor’s Office Fuck With TS Kendra Sinclaire

Doctor’s Office Fuck With TS Kendra Sinclaire

05:15
TRANSSEXUAL SCHOOLGIRLS 3 - Scene 1

TRANSSEXUAL SCHOOLGIRLS 3 - Scene 1

25:03
Jenna's masturbation (female mask, cross dressing, transvestite, rubber, heels, pantyhose, gloves)

Jenna's masturbation (female mask, cross dressing, transvestite, rubber, heels, pantyhose, gloves)

17:36
Barely Female 13 - Scene 6

Barely Female 13 - Scene 6

14:43
She Male Domain 03 - Scene 3

She Male Domain 03 - Scene 3

14:13
Hot BDSM Roleplay Until Cumshot

Hot BDSM Roleplay Until Cumshot

10:24
Shemale Love to Role Play

Shemale Love to Role Play

10:04
Dirndl Beermaid Dickgirl Masturbates cums

Dirndl Beermaid Dickgirl Masturbates cums

37:19
Trans roleplay, teenage

Trans roleplay, teenage

14:33
Role Playing

Role Playing

24:39
Shemales Really Loves Role Playing

Shemales Really Loves Role Playing

10:08
3d story, 3d futanari, family album

3d story, 3d futanari, family album

34:15
Lesbo, catgirl

Lesbo, catgirl

11:51
HD: Submissive gets FACE FUCKING in Spandex mask by DOM Alpha FTM Transman

HD: Submissive gets FACE FUCKING in Spandex mask by DOM Alpha FTM Transman

11:21
russian trans*girl laska plays with her toys for you role play

russian trans*girl laska plays with her toys for you role play

13:30
trans mommy had the cock bigger than daddy

trans mommy had the cock bigger than daddy

10:01
Couple Shemale Sucking and Role Play

Couple Shemale Sucking and Role Play

10:08
Pussy licking with a vibrator Milf sucks hot CD TS cock

Pussy licking with a vibrator Milf sucks hot CD TS cock

16:44
je me travesti pour baiser ma femme

je me travesti pour baiser ma femme

12:48
Shemale Love to Role Play

Shemale Love to Role Play

10:04
Hot Shemale Babe Maturbates Her Ass and Cock

Hot Shemale Babe Maturbates Her Ass and Cock

10:29
Hot BDSM Roleplay Until Cumshot

Hot BDSM Roleplay Until Cumshot

10:24
Hot BDSM Roleplay Until Cumshot

Hot BDSM Roleplay Until Cumshot

10:07
Hes My Girl - Scene 1

Hes My Girl - Scene 1

20:36
schoolgirl crossdresser lets off some steam

schoolgirl crossdresser lets off some steam

15:21
Shemale Blowjobs 5 - Scene 4

Shemale Blowjobs 5 - Scene 4

18:00
Hermaphrodite, teen joi, futanari pantyhose

Hermaphrodite, teen joi, futanari pantyhose

11:04
Ts Allie Hart roleplay fantasy

Ts Allie Hart roleplay fantasy

13:27
Roleplay, chaturbate

Roleplay, chaturbate

13:45
Cosplay, romantic, petite

Cosplay, romantic, petite

13:20
Ebony Transgirl Sophie Renan Beats Her Ass and BBC

Ebony Transgirl Sophie Renan Beats Her Ass and BBC

14:59
Dirty Feet Blowjob Huge Mouth Full Of Cum And Swallowing

Dirty Feet Blowjob Huge Mouth Full Of Cum And Swallowing

22:12
Taboo TS/female 4way with Bianca Stone, Arabelle Raphael and Delia Delions

Taboo TS/female 4way with Bianca Stone, Arabelle Raphael and Delia Delions

17:25
trans schoolgirl fucked bareback by naughty daddy

trans schoolgirl fucked bareback by naughty daddy

01:32
transsexual nurses - Scene 1

transsexual nurses - Scene 1

22:30
Foot fetish, cuckold, predominance

Foot fetish, cuckold, predominance

10:28
Huge dick shemale, sean michaels black cock, sean michaels shemale

Huge dick shemale, sean michaels black cock, sean michaels shemale

32:05
Let's Make a Baby

Let's Make a Baby

10:54
TEENAGE TRANSSEXUAL NURSES 8 - Scene 4

TEENAGE TRANSSEXUAL NURSES 8 - Scene 4

25:05
Shemale Anal Adventures - Scene 3

Shemale Anal Adventures - Scene 3

30:59
Pigtails Roleplay Yard Fuckfest

Pigtails Roleplay Yard Fuckfest

06:42
Psycho ninja sexy interrogation

Psycho ninja sexy interrogation

30:09
Shemale Love to Role Play

Shemale Love to Role Play

10:04
Hot Milf and Sexy Stud Couple Trade Oral in Lingerie

Hot Milf and Sexy Stud Couple Trade Oral in Lingerie

04:27
Caption Stories: Anchorwoman Position

Caption Stories: Anchorwoman Position

17:18
Sissy Training with Mistress

Sissy Training with Mistress

13:04
Tgirl Kimberly role plays as a horny cop

Tgirl Kimberly role plays as a horny cop

05:00
Femdom strapon, futa pov, futa tmc

Femdom strapon, futa pov, futa tmc

11:37
Batgirl masturbates cock with her feet

Batgirl masturbates cock with her feet

08:01
Hot Babe Dressed As Batgirl BJ

Hot Babe Dressed As Batgirl BJ

08:40
Raw-fuck, role-play

Raw-fuck, role-play

13:04
Sissy in chastity, sissy crossdresser, chastity husband sissy

Sissy in chastity, sissy crossdresser, chastity husband sissy

11:08
Roleplay, sensual

Roleplay, sensual

12:51
Batgirl masturbates cock with her feet

Batgirl masturbates cock with her feet

08:14
Catwoman, batgirl spank catwoman, latex

Catwoman, batgirl spank catwoman, latex

10:10
Brasil, le rompen el culo, shemale rompe culos

Brasil, le rompen el culo, shemale rompe culos

22:16
Thanks for the date, but I just wanna fuck you more then ever now. Trans gentle dom roleplay

Thanks for the date, but I just wanna fuck you more then ever now. Trans gentle dom roleplay

14:23
Role Play Trannys!

Role Play Trannys!

18:01
Newlyweds fuck a shemale on their wedding night

Newlyweds fuck a shemale on their wedding night

22:29
Shemales Really Loves Role Playing

Shemales Really Loves Role Playing

10:08
Guy's ass taken with dildo and huge strapon by ravishing milf

Guy's ass taken with dildo and huge strapon by ravishing milf

13:30
Barely Female 21 - Scene 1

Barely Female 21 - Scene 1

14:23
Mommy takes the virginity of her trans daughter

Mommy takes the virginity of her trans daughter

13:51
Euro Zone claims for Better School Education, RedVex Schoolgirl

Euro Zone claims for Better School Education, RedVex Schoolgirl

14:10
Tranny flavor desserts

Tranny flavor desserts

19:15
Role-Playing Shemale Sluts

Role-Playing Shemale Sluts

18:55
Riley Storm Flogged and Fucked

Riley Storm Flogged and Fucked

15:25
Seductive TS Sophia Bella Wanks Her Beautiful Cock

Seductive TS Sophia Bella Wanks Her Beautiful Cock

14:56
Roleplay, fantasy role play

Roleplay, fantasy role play

11:21
Couple Shemale Sucking and Role Play

Couple Shemale Sucking and Role Play

10:08
Lesbian story, story, tmc

Lesbian story, story, tmc

10:25
Tgirl slave, china live play

Tgirl slave, china live play

11:29
Cum eating cuckold, cheating, mistress

Cum eating cuckold, cheating, mistress

10:32
Cage pet, petgirl

Cage pet, petgirl

13:28
Stylish Afro Big Breasted Shemale in Leather Gloves Fucks Hooded Cock Horny

Stylish Afro Big Breasted Shemale in Leather Gloves Fucks Hooded Cock Horny

11:10
National Transsexual - Scene 5

National Transsexual - Scene 5

13:05
Tranny Duo Having A Nude Role Play

Tranny Duo Having A Nude Role Play

10:15
Catgirl, fetish blowjob

Catgirl, fetish blowjob

13:30
Couple Shemale Sucking and Role Play

Couple Shemale Sucking and Role Play

10:08
Schoolgirls ts Lena Kelly and Cis Goth Charlotte Share Teacher

Schoolgirls ts Lena Kelly and Cis Goth Charlotte Share Teacher

20:08
Shemale lifts a guy, fat guy

Shemale lifts a guy, fat guy

16:11
Hot BDSM Roleplay Until Cumshot

Hot BDSM Roleplay Until Cumshot

10:24
Ass fucked with glass dildo until orgasm by tranny crossdresser

Ass fucked with glass dildo until orgasm by tranny crossdresser

08:40
Anal invasion, transsexual, slave

Anal invasion, transsexual, slave

10:30
Fucking the Catgirl Maid

Fucking the Catgirl Maid

10:43
scene o_tsMia tha Prostitute

scene o_tsMia tha Prostitute

11:18
roleplay tranny gets fucked by two plumbers

roleplay tranny gets fucked by two plumbers

16:56
Tied up crossdresser just can't cum

Tied up crossdresser just can't cum

22:02
Asuka's playtime (female mask, asian, pantyhose, fetish, feminization, trans, crossdress, mask, wig)

Asuka's playtime (female mask, asian, pantyhose, fetish, feminization, trans, crossdress, mask, wig)

14:04
SHE-MALE SUPERMODEL CAROL - Scene 2

SHE-MALE SUPERMODEL CAROL - Scene 2

16:35
Surprise I Have A Dick - Scene 1

Surprise I Have A Dick - Scene 1

19:03
Vintage Karen Dior role play

Vintage Karen Dior role play

18:06
date me, "modify" my beverage and fuck me cuz I love it

date me, "modify" my beverage and fuck me cuz I love it

10:31
Tranny Duo Having A Nude Role Play

Tranny Duo Having A Nude Role Play

10:12
Haunted Hotel Room TS Fuck

Haunted Hotel Room TS Fuck

05:06
Evening Encounter 1 - Working 9 to 5 Faith Elaine & Liz Zarko tag team EW

Evening Encounter 1 - Working 9 to 5 Faith Elaine & Liz Zarko tag team EW

31:14
Krystal's Hotel Tease (trans, fetish, female mask, mask, feminization, crossdress, transformation)

Krystal's Hotel Tease (trans, fetish, female mask, mask, feminization, crossdress, transformation)

30:48
Cum glasses hot licking

Cum glasses hot licking

22:47
Shemales Really Loves Role Playing

Shemales Really Loves Role Playing

10:08