Sort: Popularity

Roleplay: 122 Videos, grouped by Popularity

fox love wolf yiff
13:46

fox love wolf yiff

Big Dick Bitch presents ROLE PLAY 4 Dvd
03:18

Big Dick Bitch presents ROLE PLAY 4 Dvd

Russian Crossdress Roleplayers
40:42

Russian Crossdress Roleplayers

GenderX - Transsexual Nurse Gives Full Body Physical Exam
10:51

GenderX - Transsexual Nurse Gives Full Body Physical Exam

Haunted Hotel Room TS Fuck
05:06

Haunted Hotel Room TS Fuck

Transsexual Heartbreakers 14 - Scene 4
17:45

Transsexual Heartbreakers 14 - Scene 4

Hot Passable Crossdresser Fucks Sexy Babe Hard
11:33

Hot Passable Crossdresser Fucks Sexy Babe Hard

Lazy maid gets anal abuse for not cleaning with dirty talking abuse
07:23

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

Parodie, 3d futanari, cartoon parody 3d
01:02:08

Parodie, 3d futanari, cartoon parody 3d

Caught in the Act .. RedheadLiz catches EWGuy in bed w/stepdaugther Faith
22:37

Caught in the Act .. RedheadLiz catches EWGuy in bed w/stepdaugther Faith

Sissy Training with Mistress
13:04

Sissy Training with Mistress

Evening Encounter 1 - Working 9 to 5 Faith Elaine & Liz Zarko tag team EW
31:14

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

Tgirl slave, china live play
11:29

Tgirl slave, china live play

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Sexy BBW Nurse Tanya Mellow Sucking and riding
09:04

Sexy BBW Nurse Tanya Mellow Sucking and riding

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Riley Storm Flogged and Fucked
15:25

Riley Storm Flogged and Fucked

Role Playing
24:39

Role Playing

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Fucking the Catgirl Maid
10:43

Fucking the Catgirl Maid

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Barely Female 21 - Scene 1
14:23

Barely Female 21 - Scene 1

She Male Domain 03 - Scene 3
14:13

She Male Domain 03 - Scene 3

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Roleplay, chaturbate
13:45

Roleplay, chaturbate

Tgirl Kimberly role plays as a horny cop
05:00

Tgirl Kimberly role plays as a horny cop

Hot BDSM Roleplay Until Cumshot
10:07

Hot BDSM Roleplay Until Cumshot

trans mommy had the cock bigger than daddy
10:01

trans mommy had the cock bigger than daddy

schoolgirl crossdresser lets off some steam
15:21

schoolgirl crossdresser lets off some steam

Dirndl Beermaid Dickgirl Masturbates cums
37:19

Dirndl Beermaid Dickgirl Masturbates cums

Taboo TS/female 4way with Bianca Stone, Arabelle Raphael and Delia Delions
17:25

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

Sissy Maids in the Mirror - PVC TS British Maid Fetish Bimbo Sasha de Sade
23:35

Sissy Maids in the Mirror - PVC TS British Maid Fetish Bimbo Sasha de Sade

Batgirl masturbates cock with her feet
08:14

Batgirl masturbates cock with her feet

Raw-fuck, role-play
13:04

Raw-fuck, role-play

Hot TS Asian Cheerleader Gets Pounded Raw
20:08

Hot TS Asian Cheerleader Gets Pounded Raw

Sri lanka, shemale cum no hands
11:20

Sri lanka, shemale cum no hands

Ass fucked with glass dildo until orgasm by tranny crossdresser
08:40

Ass fucked with glass dildo until orgasm by tranny crossdresser

Cosplay, romantic, petite
13:20

Cosplay, romantic, petite

Seductive TS Sophia Bella Wanks Her Beautiful Cock
14:56

Seductive TS Sophia Bella Wanks Her Beautiful Cock

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Shemale Anal Adventures - Scene 3
30:59

Shemale Anal Adventures - Scene 3

androgino
08:29

androgino

Lesbian story, story, tmc
10:25

Lesbian story, story, tmc

Mesmerized to suck trans cock
15:38

Mesmerized to suck trans cock

Roleplay, fantasy role play
11:21

Roleplay, fantasy role play

Little Red Tranny Hood
31:24

Little Red Tranny Hood

Psycho ninja sexy interrogation
30:09

Psycho ninja sexy interrogation

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Tranny flavor desserts
19:15

Tranny flavor desserts

Mommy takes the virginity of her trans daughter
13:51

Mommy takes the virginity of her trans daughter

Let's Make a Baby
10:54

Let's Make a Baby

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Mr 18 Freaky Adventures - Scene 1
15:22

Mr 18 Freaky Adventures - Scene 1

roleplay tranny gets fucked by two plumbers
16:56

roleplay tranny gets fucked by two plumbers

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Newlyweds fuck a shemale on their wedding night
22:29

Newlyweds fuck a shemale on their wedding night

Roleplay, sensual
12:51

Roleplay, sensual

Trans roleplay, teenage
14:33

Trans roleplay, teenage

Role Play Trannys!
18:01

Role Play Trannys!

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

National Transsexual - Scene 5
13:05

National Transsexual - Scene 5

Guy's ass taken with dildo and huge strapon by ravishing milf
13:30

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

trans schoolgirl fucked bareback by naughty daddy
01:32

trans schoolgirl fucked bareback by naughty daddy

Shemale Nurses in Stockings Suck and Fuck Eachother
10:00

Shemale Nurses in Stockings Suck and Fuck Eachother

Thanks for the date, but I just wanna fuck you more then ever now. Trans gentle dom roleplay
14:23

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

Sissy in chastity, sissy crossdresser, chastity husband sissy
11:08

Sissy in chastity, sissy crossdresser, chastity husband sissy

Dirty Feet Blowjob Huge Mouth Full Of Cum And Swallowing
22:12

Dirty Feet Blowjob Huge Mouth Full Of Cum And Swallowing

Asuka's playtime (female mask, asian, pantyhose, fetish, feminization, trans, crossdress, mask, wig)
14:04

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

Foot fetish, cuckold, predominance
10:28

Foot fetish, cuckold, predominance

date me, "modify" my beverage and fuck me cuz I love it
10:31

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

scene o_tsMia tha Prostitute
11:18

scene o_tsMia tha Prostitute

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Vintage Karen Dior role play
18:06

Vintage Karen Dior role play

Shemale Blowjobs 5 - Scene 4
18:00

Shemale Blowjobs 5 - Scene 4

Lesbo, catgirl
11:51

Lesbo, catgirl

Cum eating cuckold, cheating, mistress
10:32

Cum eating cuckold, cheating, mistress

Trap in Maid Lingerie Eats Own Cum
10:18

Trap in Maid Lingerie Eats Own Cum

Anal invasion, transsexual, slave
10:30

Anal invasion, transsexual, slave

Ebony Transgirl Sophie Renan Beats Her Ass and BBC
14:59

Ebony Transgirl Sophie Renan Beats Her Ass and BBC

Two young trannies role playing on cam
21:28

Two young trannies role playing on cam

ASMR Draining your balls into my pussy first thing in the morning Catgirl Blowjob Riding
10:12

ASMR Draining your balls into my pussy first thing in the morning Catgirl Blowjob Riding

Cage pet, petgirl
13:28

Cage pet, petgirl

Tranny Duo Having A Nude Role Play
10:15

Tranny Duo Having A Nude Role Play

Pussy licking with a vibrator Milf sucks hot CD TS cock
16:44

Pussy licking with a vibrator Milf sucks hot CD TS cock

Doctor’s Office Fuck With TS Kendra Sinclaire
05:15

Doctor’s Office Fuck With TS Kendra Sinclaire

Natalie Mars, Goddess Tangent & Jasmine Mendez and strapon
17:09

Natalie Mars, Goddess Tangent & Jasmine Mendez and strapon

Hot Babe Dressed As Batgirl BJ
08:40

Hot Babe Dressed As Batgirl BJ

Tied up crossdresser just can't cum
22:02

Tied up crossdresser just can't cum

Hot Milf and Sexy Stud Couple Trade Oral in Lingerie
04:27

Hot Milf and Sexy Stud Couple Trade Oral in Lingerie

Christmas stepmom roleplay
22:10

Christmas stepmom roleplay

3d story, 3d futanari, family album
34:15

3d story, 3d futanari, family album

Role-Playing Shemale Sluts
18:55

Role-Playing Shemale Sluts

Hentai femboy sissy joi, femboy crossdresser joi
10:06

Hentai femboy sissy joi, femboy crossdresser joi

je me travesti pour baiser ma femme
12:48

je me travesti pour baiser ma femme

Futanari Chicks with Dicks Fantasy Roleplay JOI
10:54

Futanari Chicks with Dicks Fantasy Roleplay JOI

Catwoman, batgirl spank catwoman, latex
10:10

Catwoman, batgirl spank catwoman, latex

Stylish Afro Big Breasted Shemale in Leather Gloves Fucks Hooded Cock Horny
11:10

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

Hes My Girl - Scene 4
22:32

Hes My Girl - Scene 4

Shemale lifts a guy, fat guy
16:11

Shemale lifts a guy, fat guy

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Haunted Hotel Room TS Fuck
05:06

Haunted Hotel Room TS Fuck

Giantess roleplay and cumshot
15:47

Giantess roleplay and cumshot

TS Babe fucks her Brotherinlaw
06:10

TS Babe fucks her Brotherinlaw

transsexual nurses - Scene 1
22:30

transsexual nurses - Scene 1

Jenna's masturbation (female mask, cross dressing, transvestite, rubber, heels, pantyhose, gloves)
17:36

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

Cum glasses hot licking
22:47

Cum glasses hot licking

Tranny Duo Having A Nude Role Play
10:12

Tranny Duo Having A Nude Role Play

HD: Submissive gets FACE FUCKING in Spandex mask by DOM Alpha FTM Transman
11:21

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

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Hermaphrodite, teen joi, futanari pantyhose
11:04

Hermaphrodite, teen joi, futanari pantyhose

Batgirl masturbates cock with her feet
08:01

Batgirl masturbates cock with her feet

Shemale Love to Role Play
10:04

Shemale Love to Role Play

russian trans*girl laska plays with her toys for you role play
13:30

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

Huge dick shemale, sean michaels black cock, sean michaels shemale
32:05

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

Catgirl, fetish blowjob
13:30

Catgirl, fetish blowjob

Brasil, le rompen el culo, shemale rompe culos
22:16

Brasil, le rompen el culo, shemale rompe culos

Femdom strapon, futa pov, futa tmc
11:37

Femdom strapon, futa pov, futa tmc

Hot Shemale Babe Maturbates Her Ass and Cock
10:29

Hot Shemale Babe Maturbates Her Ass and Cock

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Barely Female 13 - Scene 6
14:43

Barely Female 13 - Scene 6