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Roleplay: 122 Videos, grouped by Date

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

GenderX - Transsexual Nurse Gives Full Body Physical Exam

fox love wolf yiff
13:46

fox love wolf yiff

Haunted Hotel Room TS Fuck
05:06

Haunted Hotel Room TS Fuck

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

Russian Crossdress Roleplayers
40:42

Russian Crossdress Roleplayers

Transsexual Heartbreakers 14 - Scene 4
17:45

Transsexual Heartbreakers 14 - Scene 4

Big Dick Bitch presents ROLE PLAY 4 Dvd
03:18

Big Dick Bitch presents ROLE PLAY 4 Dvd

Christmas stepmom roleplay
22:10

Christmas stepmom roleplay

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

Giantess roleplay and cumshot
15:47

Giantess roleplay and cumshot

Little Red Tranny Hood
31:24

Little Red Tranny Hood

Psycho ninja sexy interrogation
30:09

Psycho ninja sexy interrogation

Mommy takes the virginity of her trans daughter
13:51

Mommy takes the virginity of her trans daughter

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

trans mommy had the cock bigger than daddy
10:01

trans mommy had the cock bigger than daddy

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)

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)

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

Foot fetish, cuckold, predominance
10:28

Foot fetish, cuckold, predominance

Cum eating cuckold, cheating, mistress
10:32

Cum eating cuckold, cheating, mistress

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Cosplay, romantic, petite
13:20

Cosplay, romantic, petite

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Shemales Really Loves Role Playing
10:08

Shemales Really Loves Role Playing

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Anal invasion, transsexual, slave
10:30

Anal invasion, transsexual, slave

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Couple Shemale Sucking and Role Play
10:08

Couple Shemale Sucking and Role Play

Mesmerized to suck trans cock
15:38

Mesmerized to suck trans cock

Raw-fuck, role-play
13:04

Raw-fuck, role-play

Roleplay, fantasy role play
11:21

Roleplay, fantasy role play

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Shemale Love to Role Play
10:04

Shemale Love to Role Play

Roleplay, chaturbate
13:45

Roleplay, chaturbate

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

Sissy in chastity, sissy crossdresser, chastity husband sissy

Catgirl, fetish blowjob
13:30

Catgirl, fetish blowjob

Shemale lifts a guy, fat guy
16:11

Shemale lifts a guy, fat guy

Trans roleplay, teenage
14:33

Trans roleplay, teenage

Tranny Duo Having A Nude Role Play
10:15

Tranny Duo Having A Nude Role Play

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

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

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

Roleplay, sensual
12:51

Roleplay, sensual

Sri lanka, shemale cum no hands
11:20

Sri lanka, shemale cum no hands

roleplay tranny gets fucked by two plumbers
16:56

roleplay tranny gets fucked by two plumbers

Hentai femboy sissy joi, femboy crossdresser joi
10:06

Hentai femboy sissy joi, femboy crossdresser joi

Lesbian story, story, tmc
10:25

Lesbian story, story, tmc

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

Parodie, 3d futanari, cartoon parody 3d

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

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

Femdom strapon, futa pov, futa tmc
11:37

Femdom strapon, futa pov, futa tmc

Cage pet, petgirl
13:28

Cage pet, petgirl

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

Brasil, le rompen el culo, shemale rompe culos

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

je me travesti pour baiser ma femme
12:48

je me travesti pour baiser ma femme

Tgirl slave, china live play
11:29

Tgirl slave, china live play

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

Hermaphrodite, teen joi, futanari pantyhose
11:04

Hermaphrodite, teen joi, futanari pantyhose

scene o_tsMia tha Prostitute
11:18

scene o_tsMia tha Prostitute

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

3d story, 3d futanari, family album

Futanari Chicks with Dicks Fantasy Roleplay JOI
10:54

Futanari Chicks with Dicks Fantasy Roleplay JOI

Two young trannies role playing on cam
21:28

Two young trannies role playing on cam

Tranny flavor desserts
19:15

Tranny flavor desserts

Dirndl Beermaid Dickgirl Masturbates cums
37:19

Dirndl Beermaid Dickgirl Masturbates cums

Catwoman, batgirl spank catwoman, latex
10:10

Catwoman, batgirl spank catwoman, latex

Hot TS Asian Cheerleader Gets Pounded Raw
20:08

Hot TS Asian Cheerleader Gets Pounded Raw

Riley Storm Flogged and Fucked
15:25

Riley Storm Flogged and Fucked

schoolgirl crossdresser lets off some steam
15:21

schoolgirl crossdresser lets off some steam

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

Dirty Feet Blowjob Huge Mouth Full Of Cum And Swallowing

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

Natalie Mars, Goddess Tangent & Jasmine Mendez and strapon

Tied up crossdresser just can't cum
22:02

Tied up crossdresser just can't cum

Trap in Maid Lingerie Eats Own Cum
10:18

Trap in Maid Lingerie Eats Own Cum

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

Ebony Transgirl Sophie Renan Beats Her Ass and BBC

Hot Shemale Babe Maturbates Her Ass and Cock
10:29

Hot Shemale Babe Maturbates Her Ass and Cock

Fucking the Catgirl Maid
10:43

Fucking the Catgirl Maid

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

Sissy Training with Mistress
13:04

Sissy Training with Mistress

Seductive TS Sophia Bella Wanks Her Beautiful Cock
14:56

Seductive TS Sophia Bella Wanks Her Beautiful Cock

transsexual nurses - Scene 1
22:30

transsexual nurses - Scene 1

Shemale Anal Adventures - Scene 3
30:59

Shemale Anal Adventures - Scene 3

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

Lesbo, catgirl
11:51

Lesbo, catgirl

TS Babe fucks her Brotherinlaw
06:10

TS Babe fucks her Brotherinlaw

trans schoolgirl fucked bareback by naughty daddy
01:32

trans schoolgirl fucked bareback by naughty daddy

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

Ass fucked with glass dildo until orgasm by tranny crossdresser

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

Pussy licking with a vibrator Milf sucks hot CD TS cock

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

Hot Babe Dressed As Batgirl BJ
08:40

Hot Babe Dressed As Batgirl BJ

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Hot BDSM Roleplay Until Cumshot
10:07

Hot BDSM Roleplay Until Cumshot

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Haunted Hotel Room TS Fuck
05:06

Haunted Hotel Room TS Fuck

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

Hot Milf and Sexy Stud Couple Trade Oral in Lingerie

Tgirl Kimberly role plays as a horny cop
05:00

Tgirl Kimberly role plays as a horny cop

Batgirl masturbates cock with her feet
08:01

Batgirl masturbates cock with her feet

Batgirl masturbates cock with her feet
08:14

Batgirl masturbates cock with her feet

Let's Make a Baby
10:54

Let's Make a Baby

Role Playing
24:39

Role Playing

Role-Playing Shemale Sluts
18:55

Role-Playing Shemale Sluts

Cum glasses hot licking
22:47

Cum glasses hot licking

Vintage Karen Dior role play
18:06

Vintage Karen Dior role play

She Male Domain 03 - Scene 3
14:13

She Male Domain 03 - Scene 3

Role Play Trannys!
18:01

Role Play Trannys!

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

Doctor’s Office Fuck With TS Kendra Sinclaire

Barely Female 13 - Scene 6
14:43

Barely Female 13 - Scene 6

National Transsexual - Scene 5
13:05

National Transsexual - Scene 5

Shemale Nurses in Stockings Suck and Fuck Eachother
10:00

Shemale Nurses in Stockings Suck and Fuck Eachother

Hes My Girl - Scene 4
22:32

Hes My Girl - Scene 4

Hot BDSM Roleplay Until Cumshot
10:24

Hot BDSM Roleplay Until Cumshot

Mr 18 Freaky Adventures - Scene 1
15:22

Mr 18 Freaky Adventures - Scene 1

Shemale Blowjobs 5 - Scene 4
18:00

Shemale Blowjobs 5 - Scene 4

Sexy BBW Nurse Tanya Mellow Sucking and riding
09:04

Sexy BBW Nurse Tanya Mellow Sucking and riding

Newlyweds fuck a shemale on their wedding night
22:29

Newlyweds fuck a shemale on their wedding night

androgino
08:29

androgino

Barely Female 21 - Scene 1
14:23

Barely Female 21 - Scene 1