Top-Rated

Roleplay: 117 Videos, grouped by Popularity

Hot Passable Crossdresser Fucks Sexy Babe Hard
11:33

Hot Passable Crossdresser Fucks Sexy Babe Hard

Crossdressing couple loves roleplaying and sex
12:20

Crossdressing couple loves roleplaying and sex

Transsexual Heartbreakers 14 - Scene 4
17:45

Transsexual Heartbreakers 14 - Scene 4

Russian Crossdress Roleplayers
40:42

Russian Crossdress Roleplayers

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

Big Dick Bitch presents ROLE PLAY 4 Dvd
03:18

Big Dick Bitch presents ROLE PLAY 4 Dvd

Sissy Training with Mistress
13:04

Sissy Training with Mistress

Newlyweds fuck a shemale on their wedding night
22:29

Newlyweds fuck a shemale on their wedding night

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

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

Brasil, le rompen el culo, shemale rompe culos

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

Hot Milf and Sexy Stud Couple Trade Oral in Lingerie

Hentai femboy sissy joi, femboy crossdresser joi

Cosplay, romantic, petite
13:20

Cosplay, romantic, petite

Hot Shemale Babe Maturbates Her Ass and Cock
10:29

Hot Shemale Babe Maturbates Her Ass and Cock

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

Mesmerized to suck trans cock
15:38

Mesmerized to suck trans cock

Riley Storm Flogged and Fucked
15:25

Riley Storm Flogged and Fucked

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

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

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Trap in Maid Lingerie Eats Own Cum
10:18

Trap in Maid Lingerie Eats Own Cum

Seductive TS Sophia Bella Wanks Her Beautiful Cock
14:56

Seductive TS Sophia Bella Wanks Her Beautiful Cock

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

Dirty Feet Blowjob Huge Mouth Full Of Cum And Swallowing

Shemale Love to Role Play
10:04

Shemale Love to Role Play

schoolgirl crossdresser lets off some steam
15:21

schoolgirl crossdresser lets off some steam

SHE-MALE SUPERMODEL CAROL - Scene 2
16:35

SHE-MALE SUPERMODEL CAROL - Scene 2

Hot TS Asian Cheerleader Gets Pounded Raw
20:08

Hot TS Asian Cheerleader Gets Pounded Raw

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)

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Shemale Love to Role Play
10:04

Shemale Love to Role Play

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

Parodie, 3d futanari, cartoon parody 3d

Foot fetish, cuckold, predominance
10:28

Foot fetish, cuckold, predominance

Hot BDSM Roleplay Until Cumshot
10:07

Hot BDSM Roleplay Until Cumshot

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

Batgirl masturbates cock with her feet
08:01

Batgirl masturbates cock with her feet

Cum eating cuckold, cheating, mistress
10:32

Cum eating cuckold, cheating, mistress

TRANSSEXUAL SCHOOLGIRLS 3 - Scene 1
25:03

TRANSSEXUAL SCHOOLGIRLS 3 - Scene 1

Tgirl Kimberly role plays as a horny cop
05:00

Tgirl Kimberly role plays as a horny cop

Dirndl Beermaid Dickgirl Masturbates cums
37:19

Dirndl Beermaid Dickgirl Masturbates cums

Krystal's Hotel Tease (trans, fetish, female mask, mask, feminization, crossdress, transformation)
30:48

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

Shemale Nurses in Stockings Suck and Fuck Eachother
10:00

Shemale Nurses in Stockings Suck and Fuck Eachother

Fucking the Catgirl Maid
10:43

Fucking the Catgirl Maid

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

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

Sissy in chastity, sissy crossdresser, chastity husband sissy

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

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

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

Pussy licking with a vibrator Milf sucks hot CD TS cock

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)

Hot Babe Dressed As Batgirl BJ
08:40

Hot Babe Dressed As Batgirl BJ

TEENAGE TRANSSEXUAL NURSES 8 - Scene 4
25:05

TEENAGE TRANSSEXUAL NURSES 8 - Scene 4

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

Ebony Transgirl Sophie Renan Beats Her Ass and BBC

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

transsexual nurses - Scene 1
22:30

transsexual nurses - Scene 1

Lesbian story, story, tmc
10:25

Lesbian story, story, tmc

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

She Male Domain 03 - Scene 3
14:13

She Male Domain 03 - Scene 3

Mommy takes the virginity of her trans daughter

Pigtails Roleplay Yard Fuckfest
06:42

Pigtails Roleplay Yard Fuckfest

TS Babe fucks her Brotherinlaw
06:10

TS Babe fucks her Brotherinlaw

Vintage Karen Dior role play
18:06

Vintage Karen Dior role play

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

Ass fucked with glass dildo until orgasm by tranny crossdresser

trans schoolgirl fucked bareback by naughty daddy
01:32

trans schoolgirl fucked bareback by naughty daddy

Barely Female 21 - Scene 1
14:23

Barely Female 21 - Scene 1

Catwoman, batgirl spank catwoman, latex
10:10

Catwoman, batgirl spank catwoman, latex

Shemale Blowjobs 5 - Scene 4
18:00

Shemale Blowjobs 5 - Scene 4

Shemale Love to Role Play
10:04

Shemale Love to Role Play

National Transsexual - Scene 5
13:05

National Transsexual - Scene 5

Femdom strapon, futa pov, futa tmc
11:37

Femdom strapon, futa pov, futa tmc

Surprise I Have A Dick - Scene 1
19:03

Surprise I Have A Dick - Scene 1

Batgirl masturbates cock with her feet
08:14

Batgirl masturbates cock with her feet

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

Caption Stories: Anchorwoman Position
17:18

Caption Stories: Anchorwoman Position

Hermaphrodite, teen joi, futanari pantyhose
11:04

Hermaphrodite, teen joi, futanari pantyhose

Haunted Hotel Room TS Fuck
05:06

Haunted Hotel Room TS Fuck

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Futanari Chicks with Dicks Fantasy Roleplay JOI
10:54

Futanari Chicks with Dicks Fantasy Roleplay JOI

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

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

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

Barely Female 13 - Scene 6
14:43

Barely Female 13 - Scene 6

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