New Tranny Videos Tagged with role play

VRchat ERP: Mommy's Event (Futa x Girl)
VRchat ERP: Mommy's Event (Futa x Girl)
9:29
100%
4 months ago
1 713
Wanking training with Anna HD
Wanking training with Anna
12:03
0%
3 months ago
289
Day 11 in Chastity: Sissy having Pubic Hair, Cleaning my Cage on Shower and Pissing on my own Feet HD
Day 11 in Chastity: Sissy having Pubic Hair, Cleaning my Cage on Shower and Pissin...
12:15
50%
1 year ago
4 392
Femboy hot cums and gets an orgasm from the caress hard cock ( slut tranny) HD
Femboy hot cums and gets an orgasm from the caress hard cock ( slut tranny)
12:47
100%
4 months ago
721
Be a Good Boy and Eat All Your Cum!! JOI / CEI HD
Be a Good Boy and Eat All Your Cum!! JOI / CEI
7:22
84%
7 months ago
27 182
Kasnicole 002V Kigurumi Office Lady take off black and on grey pantyhose vibrate masturbate on pussy HD
Kasnicole 002V Kigurumi Office Lady take off black and on grey pantyhose vibrate m...
14:05
0%
2 months ago
654
Mistress Kayla Swallow Mommy's Big COCK like a Good Sissy Boy with CUMSHOT! HD
Mistress Kayla Swallow Mommy's Big COCK like a Good Sissy Boy with CUMSHOT!
19:25
95%
9 months ago
6 991
Pikachu Cosplay Bikini Babe HD
Pikachu Cosplay Bikini Babe
9:04
0%
1 month ago
152
Supreme witch give her maid ass spanking and whipping for poorly cleaned boots HD
Supreme witch give her maid ass spanking and whipping for poorly cleaned boots
12:26
100%
8 months ago
1 016
Daily Jerk Off Instruction for Gamers (Preview) HD
Daily Jerk Off Instruction for Gamers (Preview)
10:36
100%
7 months ago
1 696
Geraldine (pantyhose, female mask, feminization, trans, crossdress, sissy, mask) HD
Geraldine (pantyhose, female mask, feminization, trans, crossdress, sissy, mask)
8:16
0%
6 months ago
1 187
Become a Shemale Sex Slave sissy training instructions HD
Become a Shemale Sex Slave sissy training instructions
12:58
0%
1 month ago
679
Anime trans girl takes care of her men and eats her cum. HD
Anime trans girl takes care of her men and eats her cum.
16:00
100%
8 months ago
1 469
Femdom-Goddess Dominating & Pegging Sissy Bondman with Love - Chinese Femdom HD
Femdom-Goddess Dominating & Pegging Sissy Bondman with Love - Chinese Femdom
17:11
66%
1 year ago
8 996
Sissification feminization sissy training - Sissy husband story (english voice) HD
Sissification feminization sissy training - Sissy husband story (english voice)
9:27
0%
4 hours ago
36
Black satin fetish long dress and silk jacket and high heels overknee boots and my cock hard and horny. Suck me gently HD
Black satin fetish long dress and silk jacket and high heels overknee boots and my...
8:07
0%
4 months ago
636
Shemale Yasmin Fonthys Dominate Her Man and Punishes Him Till Orgasm HD
Shemale Yasmin Fonthys Dominate Her Man and Punishes Him Till Orgasm
8:04
100%
1 month ago
327
Trans Beauty Roleplay Deepthroat Anal w Ribald (not) Old Man
Trans Beauty Roleplay Deepthroat Anal w Ribald (not) Old Man
46:42
66%
1 year ago
2 630
Trans girl takes care of daddy JOI + Cum Shot HD
Trans girl takes care of daddy JOI + Cum Shot
7:14
75%
9 months ago
3 046
Super Cute Gym Bunny with Hot Legs Needs Sex HD
Super Cute Gym Bunny with Hot Legs Needs Sex
9:24
0%
2 months ago
381
Watching Porn with Trans Step Mommy...For Educational Purposes - GenderX HD
Watching Porn with Trans Step Mommy...For Educational Purposes - GenderX
12:08
59%
1 year ago
59 462
Finger Fucking broadcast live solo masturbation loud emo slut
Finger Fucking broadcast live solo masturbation loud emo slut
18:35
0%
4 months ago
241
GenderX - Ms. Daisy Taylor Pumped at Parent Teacher Conference HD
GenderX - Ms. Daisy Taylor Pumped at Parent Teacher Conference
12:51
87%
1 year ago
6 002
School girl gets fucked in swing
School girl gets fucked in swing
6:43
100%
7 months ago
510
Sexy School Girl wants to Fuck at the Partu HD
Sexy School Girl wants to Fuck at the Partu
17:06
0%
2 days ago
68
Sexy Daddys Girl Wants To Suck HD
Sexy Daddys Girl Wants To Suck
21:19
100%
4 months ago
292
Alex's dildo play (trans, crossdress, fetish, corset, pantyhose, high heels, female mask, leather) HD
Alex's dildo play (trans, crossdress, fetish, corset, pantyhose, high heels, femal...
11:28
0%
4 weeks ago
376
2019-07-25 Christina (The Compound) - Princess - Smartphone HD
2019-07-25 Christina (The Compound) - Princess - Smartphone
23:40
0%
2 months ago
105
Travesti con correa para perros jugando con su dildo usando su boca y lenga de perra puta. HD
Travesti con correa para perros jugando con su dildo usando su boca y lenga de per...
30:57
0%
2 days ago
69
GenderX - Ella Hollywood Lastly Bonks her Stepfather HD
GenderX - Ella Hollywood Lastly Bonks her Stepfather
11:13
100%
1 year ago
3 227
Back shots (20 likes for another round of back shots) HD
Back shots (20 likes for another round of back shots)
15:49
0%
1 month ago
134
Spy on a Masturbating Femboy and Fuck him HD
Spy on a Masturbating Femboy and Fuck him
10:51
100%
1 year ago
2 043
Transgender witch demonstrates sigil Magick(part 2 of 2: with ass play and masterbation) HD
Transgender witch demonstrates sigil Magick(part 2 of 2: with ass play and masterb...
10:25
0%
8 months ago
299
2019-08-22 Christina (The Compound) - Unicorn HD
2019-08-22 Christina (The Compound) - Unicorn
15:43
0%
2 months ago
136
Waking up next to my sex doll HD
Waking up next to my sex doll
3:15
100%
9 months ago
1 985
Trans girl want you to cum HD
Trans girl want you to cum
10:02
0%
5 months ago
391
I FUCK a CUTE SISSY NEKO FEMBOY IN THE A-HOLE AND THAT GUY CUM UP ON HIS TUMMY HD
I FUCK a CUTE SISSY NEKO FEMBOY IN THE A-HOLE AND THAT GUY CUM UP ON HIS TUMMY
20:28
88%
1 year ago
7 174
Ftm moans as you creampie his hole HD
Ftm moans as you creampie his hole
5:25
0%
9 months ago
952
Anal sex Futa & Male HD
Anal sex Futa & Male
8:36
0%
3 months ago
392
Vicky Linn Fireside Fairytales HD
Vicky Linn Fireside Fairytales
12:21
0%
8 months ago
277
ME AND HOT BOY MET ON NEW YEAR AND HE FUCKED ME VERY COOL AND HARD I SUCK HE CUM HD
ME AND HOT BOY MET ON NEW YEAR AND HE FUCKED ME VERY COOL AND HARD I SUCK HE CUM
14:10
0%
4 months ago
697
Shemale doll teases and fucks the tiny pussy of a mini sexdoll
Shemale doll teases and fucks the tiny pussy of a mini sexdoll
12:38
100%
3 months ago
594
Star Wars Darth Talon Cosplay Time Lapse HD
Star Wars Darth Talon Cosplay Time Lapse
8:35
0%
5 days ago
56
FEMBOY GETS FUCKED IN THE GLORY HOLE BY SEMALE'S BIG COCK
FEMBOY GETS FUCKED IN THE GLORY HOLE BY SEMALE'S BIG COCK
9:07
100%
3 months ago
321
TS CRUELLA JOI/CEI HD
TS CRUELLA JOI/CEI
6:24
75%
7 months ago
5 328
Annika Transfemme Persuasion Ep 2 HD
Annika Transfemme Persuasion Ep 2
18:03
100%
1 month ago
348
Piss, Spanking, Tickling, Blowjob, Hardcore. Oh My! HD
Piss, Spanking, Tickling, Blowjob, Hardcore. Oh My!
28:32
100%
5 months ago
1 168
Femboy Cums to Caress A Hard Cock And Enjoys In A Red Collar ( sissy slut ) HD
Femboy Cums to Caress A Hard Cock And Enjoys In A Red Collar ( sissy slut )
9:45
100%
2 weeks ago
105
Hilda's disguise (female mask, mask, tights, trans, crossdress, high heels, short skirt, transform) HD
Hilda's disguise (female mask, mask, tights, trans, crossdress, high heels, short ...
10:29
0%
3 weeks ago
133
Cum Butterfly Begs For Cum JOI HD
Cum Butterfly Begs For Cum JOI
14:08
0%
1 week ago
151
POV: Fucking my dads best-friend HD
POV: Fucking my dads best-friend
10:36
100%
3 months ago
219
Side view of King Cock 12 inch dildo - Sissy clit leaking cum and ending on orgasm HD
Side view of King Cock 12 inch dildo - Sissy clit leaking cum and ending on orgasm
14:04
80%
4 months ago
955
Gorgeous Yoga Girl Wants To Workout Your Cock HD
Gorgeous Yoga Girl Wants To Workout Your Cock
9:58
0%
4 months ago
299
LUSTFUL AND HAWT TGIRL CLEAN ALLY'S ABODE AND FUCK HIM HD
LUSTFUL AND HAWT TGIRL CLEAN ALLY'S ABODE AND FUCK HIM
10:51
0%
1 year ago
842
Sexy Sports Babe was to Suck Cock and Get Fucked HD
Sexy Sports Babe was to Suck Cock and Get Fucked
12:13
50%
1 month ago
587
INTERRUPTED BIKERGASM by SHEMALE VERONICA TABOO with SEX MACHINE HD
INTERRUPTED BIKERGASM by SHEMALE VERONICA TABOO with SEX MACHINE
8:28
100%
8 months ago
399
Daddy Fucks Trans Slut Raw HD
Daddy Fucks Trans Slut Raw
12:27
100%
3 months ago
2 962
POV Suck Me Off til I Cum On Your Face HD
POV Suck Me Off til I Cum On Your Face
12:24
100%
4 months ago
1 219
Japanese Crossdresser Cosplay Cock blowjob HD
Japanese Crossdresser Cosplay Cock blowjob
13:24
100%
1 month ago
971
Star Wars Parody - Behind The Scenes Darth Talon Cosplay Time-lapse HD
Star Wars Parody - Behind The Scenes Darth Talon Cosplay Time-lapse
8:37
0%
5 days ago
52
Cute sissy in pink maid dress plays and cums on 50 cm butplug in chastity HD
Cute sissy in pink maid dress plays and cums on 50 cm butplug in chastity
15:05
0%
6 months ago
1 483
Crossdressing School Girl Putting on Chastity HD
Crossdressing School Girl Putting on Chastity
8:29
0%
4 months ago
431
Sissy BNWO castration bands its balls for mistress 1hr goons white extinction angel scarlett black HD
Sissy BNWO castration bands its balls for mistress 1hr goons white extinction ang...
13:57
0%
2 months ago
494
deep bubble fucking ass doggystyle with big dildo 4k ( femboy toy riding ) HD
deep bubble fucking ass doggystyle with big dildo 4k ( femboy toy riding )
12:25
0%
5 months ago
536
Femdom handjob for sissy hubby and get first cum taste HD
Femdom handjob for sissy hubby and get first cum taste
10:53
100%
7 months ago
951
CHAINED FEMINIZED SISSY GETS PEGGED HARD WITH A VIBRATING STRAPON HD
CHAINED FEMINIZED SISSY GETS PEGGED HARD WITH A VIBRATING STRAPON
9:09
0%
8 months ago
1 577
Merry Sexmas HD
Merry Sexmas
11:52
0%
7 months ago
369
DEVILS T GIRLS - Sexy Trans Casey Kisses Fucks Her School Tutor To Stay On Team Cheerleaders HD
DEVILS T GIRLS - Sexy Trans Casey Kisses Fucks Her School Tutor To Stay On Team Ch...
12:36
100%
2 months ago
385
POV Femboy Maid Cleans Masters Cock HD
POV Femboy Maid Cleans Masters Cock
2:15
100%
5 months ago
910
Femboy as Latex Anime Manga Doll Handsfree e-stim HD
Femboy as Latex Anime Manga Doll Handsfree e-stim
9:20
0%
1 week ago
120
Blair's striptease (trans, crossdress, strip, female mask, wig, pantyhose, tight dress, mask, heels) HD
Blair's striptease (trans, crossdress, strip, female mask, wig, pantyhose, tight d...
20:08
0%
4 weeks ago
374
Playboy Bunny Wants To Be Playmate Of The Year HD
Playboy Bunny Wants To Be Playmate Of The Year
10:33
100%
4 months ago
413
Trans Step-Sister JOI HD
Trans Step-Sister JOI
11:58
75%
8 months ago
4 185
JOI ESPANOL LATINA BBW HD
JOI ESPANOL LATINA BBW
10:34
100%
4 months ago
791
Crossdresser tranny palazzo wideleg fetish trousers, satin silk blazer, white office ruffled blouse and high heels boots HD
Crossdresser tranny palazzo wideleg fetish trousers, satin silk blazer, white offi...
8:26
50%
4 months ago
863
tsmaid - Mia D - School Outfit - solo trans girl petite webcam miniskirt mia HD
tsmaid - Mia D - School Outfit - solo trans girl petite webcam miniskirt mia
58:46
0%
1 week ago
276
Best cute hybrid performancer! Dancer and anal masturbation HD
Best cute hybrid performancer! Dancer and anal masturbation
6:54
100%
8 months ago
432
Enema Lady-Boy
Enema Lady-Boy
11:59
100%
1 year ago
1 143
Deanna's Hidden Knob (crossdressing, Female Mask, Transformation, Petticoat, Heels, Feminization) HD
Deanna's Hidden Knob (crossdressing, Female Mask, Transformation, Petticoat, Heels...
17:56
0%
1 year ago
1 244
Julie (Camel toe, pantyhose, masturbation, upskirt, female mask, high heels, short skirt, blonde) HD
Julie (Camel toe, pantyhose, masturbation, upskirt, female mask, high heels, short...
14:02
100%
4 weeks ago
282
Naughty Nadia (trans, crossdressing, feminization, transformation, female mask, garters, high heels) HD
Naughty Nadia (trans, crossdressing, feminization, transformation, female mask, ga...
12:35
0%
4 weeks ago
355
Kinky Shooting Big Tits HD
Kinky Shooting Big Tits
8:00
100%
11 months ago
455
Marvelous Chinese Lady-Boy in Hose acquire Feet Engulf and Screwed HD
Marvelous Chinese Lady-Boy in Hose acquire Feet Engulf and Screwed
14:59
100%
1 year ago
4 594
Hot school girl loves getting Fucked HD
Hot school girl loves getting Fucked
9:17
0%
2 months ago
351
Trans Angels - Johnny Is Disturbed From Work By Emma Rose Who Is Riding A Big Rainbow Dildo HD
Trans Angels - Johnny Is Disturbed From Work By Emma Rose Who Is Riding A Big Rain...
10:00
100%
2 months ago
774
PAWSissy Struggles with Dildo and Fuck Machine HD
PAWSissy Struggles with Dildo and Fuck Machine
16:22
100%
7 months ago
449
Foxy FtM Boyfrends self on Knotted Sextoy with Satisfyr and Cums HD
Foxy FtM Boyfrends self on Knotted Sextoy with Satisfyr and Cums
12:53
0%
2 years ago
505
Cute Cosplay PikaGirl Loves Sex in Her Bikini HD
Cute Cosplay PikaGirl Loves Sex in Her Bikini
8:24
0%
2 months ago
186
Serving Ms. Kay: Diva Khloe Kay Puts Handler throughout the Wringer HD
Serving Ms. Kay: Diva Khloe Kay Puts Handler throughout the Wringer
8:29
0%
1 year ago
2 280
Accept your Destiny Princess Sissy Slut..... Stay Flabby!!!
Accept your Destiny Princess Sissy Slut..... Stay Flabby!!!
12:21
100%
1 year ago
1 202
Real Non-Professional Close-up Silicone Mask in Horny Outfits HD
Real Non-Professional Close-up Silicone Mask in Horny Outfits
19:14
100%
1 year ago
1 179
Pacifier ABDL Solo Masturbation HD
Pacifier ABDL Solo Masturbation
5:24
100%
9 months ago
709
Femboy Todoroki Stuffed in the Gazoo HD
Femboy Todoroki Stuffed in the Gazoo
12:24
71%
2 years ago
3 710
Una sirvienta muy caliente pt2 HD
Una sirvienta muy caliente pt2
8:48
0%
7 months ago
371
Melanie's Boots (female mask, heels, pantyhose, crossdressing, boots, high heels and bodysuit) HD
Melanie's Boots (female mask, heels, pantyhose, crossdressing, boots, high heels a...
10:51
100%
1 month ago
528
Handsome Elf Wizard is actually an Insufferable Nerd (You Want to Fuck Him Anyway) HD
Handsome Elf Wizard is actually an Insufferable Nerd (You Want to Fuck Him Anyway)
3:19
0%
9 months ago
293
leg Fetishism HD
leg Fetishism
18:21
100%
5 months ago
654
Dark Angel Dark Princess 2021-11-11 Dark Angel - Freddy Kruger (BackStory) HD
Dark Angel Dark Princess 2021-11-11 Dark Angel - Freddy Kruger (BackStory)
33:26
0%
2 months ago
211
Raquel's rubber pussy (trans, crossdress, female mask, fetish, skirt, pantyhose, kinky, encasement) HD
Raquel's rubber pussy (trans, crossdress, female mask, fetish, skirt, pantyhose, k...
14:01
0%
4 weeks ago
227
Greek cd anal double dildo HD
Greek cd anal double dildo
19:08
0%
1 month ago
108
From heavy rubber mask to dog mask HD
From heavy rubber mask to dog mask
14:24
0%
9 months ago
578
Submissive Goddess Turns Dom and Makes You Her Pet HD
Submissive Goddess Turns Dom and Makes You Her Pet
8:43
0%
7 months ago
513
First time in the ass ladyboy fucks a girl HD
First time in the ass ladyboy fucks a girl
12:12
100%
6 months ago
886
BDSM Dominatrix restrains/whips Ken Doll then gets off Staring at His Ass until cum HD
BDSM Dominatrix restrains/whips Ken Doll then gets off Staring at His Ass until cum
13:09
0%
9 months ago
691
Sexy School Girl Fingering Herself and Loving Anal HD
Sexy School Girl Fingering Herself and Loving Anal
9:29
0%
4 months ago
222
Pretty Trans Teases the Camera HD
Pretty Trans Teases the Camera
10:24
100%
9 months ago
748
A sweet little get well message for you darling~ HD
A sweet little get well message for you darling~
10:53
0%
1 month ago
86
Shemale Sasha Gaucha fills her ass with bbc in Black lingerie HD
Shemale Sasha Gaucha fills her ass with bbc in Black lingerie
10:49
100%
7 months ago
445
Crossdresser in anime schoolgirl outfit comes hands free in chastity HD
Crossdresser in anime schoolgirl outfit comes hands free in chastity
10:02
75%
7 months ago
1 503
Love Potion Experiment with Erica Cherry HD
Love Potion Experiment with Erica Cherry
10:04
66%
1 year ago
2 946
Frost's Whore School 002 HD
Frost's Whore School 002
12:34
50%
2 years ago
3 306
Pretty Punk Rocker Loves Sex HD
Pretty Punk Rocker Loves Sex
11:26
0%
2 months ago
229
Trans girl roleplay deepthroat anal dirty not grandpa
Trans girl roleplay deepthroat anal dirty not grandpa
46:42
66%
1 year ago
1 515
Punk Rocker Loves Cock HD
Punk Rocker Loves Cock
5:54
0%
6 months ago
335
SPH John HD
SPH John
16:26
100%
1 year ago
2 060
Trans Girl Hides in the Bathroom to Fuck her Big Dildo and Cums HD
Trans Girl Hides in the Bathroom to Fuck her Big Dildo and Cums
10:14
100%
5 months ago
767
She Loves Teasing Her Body HD
She Loves Teasing Her Body
9:12
0%
1 month ago
110
The Humiliation of Cindy The Sissy Bitch HD
The Humiliation of Cindy The Sissy Bitch
9:34
100%
1 month ago
360
Toilet Slut Sessions - White Wig HD
Toilet Slut Sessions - White Wig
8:49
0%
2 months ago
141
Sissy Maid Uses Master's Toys HD
Sissy Maid Uses Master's Toys
11:24
100%
1 month ago
273