Challenge Videos - Trans (347)

So You're an Exhibitionist huh?! wmv

HD 0:27 / 10:50

So You're an Exhibitionist huh?! wmv

Clips4sale 2 years ago

No More Masculinity

HD 0:10 / 11:11

No More Masculinity

LoyalFans 1 year ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

LoyalFans 1 year ago

Regina Twist Vs Troy Trojan

HD 0:49 / 11:27

Regina Twist Vs Troy Trojan

Clips4sale 5 months ago

Vanessa vs JC: Arm Wrestling wmv

Vanessa vs JC: Arm Wrestling wmv

Clips4sale 6 months ago

Futa Wife's Growing Bulge - 720 MP4

61% HD 0:16 / 27:28

Futa Wife's Growing Bulge - 720 MP4

Clips4sale 3 years ago

Sissy Training Challenge 3: Embracing Emotional Elegance and Mental Feminization Tasks

Premium HD 9:48

Sissy Training Challenge 3: Embracing Emotional Elegance and Mental Feminization Tasks

Clips4sale 1 year ago

Sissy Training Challenge 4: Mastering Relationships and Communication for Deeper Connections

Premium HD 8:40

Sissy Training Challenge 4: Mastering Relationships and Communication for Deeper Connections

Clips4sale 1 year ago

combination challenge part 1 (old skool)

combination challenge part 1 (old skool)

LoyalFans 1 year ago

EXTREME SISSY MENTAL CONDITIONING - Want To Unlock Confidence and Self-Expression? Complete Mental Sissy Training

EXTREME SISSY MENTAL CONDITIONING - Want To Unlock Confidence and Self-Expression? Complete Mental Sissy Training

Futa Wife's Growing Bulge - 720 WMV

HD 0:16 / 27:28

Futa Wife's Growing Bulge - 720 WMV

Clips4sale 3 years ago

Sissy Training Week 3

Sissy Training Week 3

Clips4sale 2 years ago

Fido Futa

Clips4sale 2 years ago

Slap and stroke JOI game B version - CBT

HD 0:10 / 10:48

Slap and stroke JOI game B version - CBT

LoyalFans 1 year ago

Cum Challenge ! Who comes first???

Cum Challenge ! Who comes first???

LoyalFans 1 year ago

Sissy Katja is no longer an anal virgin!

Sissy Katja is no longer an anal virgin!

Clips4sale 2 years ago

Outlaw in: Maid Outfit Escape Challenge 1080p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 1080p

Clips4sale 10 months ago

Sissy Challenge

HD 0:11 / 12:47

Sissy Challenge

Clips4sale 3 years ago

My SISSY's anal dildo training

My SISSY's anal dildo training

Clips4sale 1 year ago

4K - Femcock vs Vibrator Round 1

4K 0:20 / 12:26

4K - Femcock vs Vibrator Round 1

Clips4sale 1 year ago

Sissy Task for Sissies

57% HD 0:20 / 6:11

Sissy Task for Sissies

Clips4sale 1 year ago

Sissy Training Challenge: Can You Handle These Tasks?

Premium HD 9:30

Sissy Training Challenge: Can You Handle These Tasks?

Clips4sale 1 year ago

Sissy Training Challenge 2: Mastering Makeup and Clothing

Premium HD 10:26

Sissy Training Challenge 2: Mastering Makeup and Clothing

Clips4sale 1 year ago

Big tit muscle futa cock to cock fuck fight: Monica vs Rogue LOW

Big tit muscle futa cock to cock fuck fight: Monica vs Rogue LOW

Clips4sale 1 year ago

THE 10 LAYERS OF PANTYHOSE OVER THE HEAD BONDAGE CHALLENGE

61% 0:16 / 20:05

THE 10 LAYERS OF PANTYHOSE OVER THE HEAD BONDAGE CHALLENGE

Clips4sale 1 year ago

Futa Wife's Growing Bulge - 1080 MP4

HD 0:11 / 27:28

Futa Wife's Growing Bulge - 1080 MP4

Clips4sale 3 years ago

Phat Ass Shemale Fernanda Cristine Barebacks a Man

HD 0:26 / 20:41

Phat Ass Shemale Fernanda Cristine Barebacks a Man

Clips4sale 3 years ago

Sissy Task Of The Day #4

Sissy Task Of The Day #4

Clips4sale 3 years ago

Crossdresser Vibed and made to Cum

Crossdresser Vibed and made to Cum

Clips4sale 4 months ago

Taking the Next Step 4K

Taking the Next Step 4K

Clips4sale 4 months ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 1080 MP4

HD 0:29 / 11:18

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 1080 MP4

Clips4sale 2 years ago

Epic Hot Gay Kissing and Mouth Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - WMV 1080

HD 0:09 / 31:02

Epic Hot Gay Kissing and Mouth Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - WMV 1080

Clips4sale 2 years ago

Suntanned Sissy

HD 0:49 / 21:55

Suntanned Sissy

Clips4sale 4 years ago

CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!

68% HD 0:30 / 17:28

CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!

Clips4sale 1 year ago

combination challenge part 2 (old skool)

combination challenge part 2 (old skool)

LoyalFans 1 year ago

TS Counselor Fantasy Weaver

59% 0:11 / 13:25

TS Counselor Fantasy Weaver

Clips4sale 3 years ago

Mini Me Social Media Challenge

Mini Me Social Media Challenge

Clips4sale 3 years ago

Fucked, Fisted & Filled with Cum by Thick Monster Cock TS

HD 0:10 / 43:34

Fucked, Fisted & Filled with Cum by Thick Monster Cock TS

LoyalFans 11 months ago

So You're an Exhibitionist huh?!

HD 0:27 / 10:50

So You're an Exhibitionist huh?!

Clips4sale 2 years ago

4K - Femcock vs Vibrator Round 2

4K 0:24 / 11:32

4K - Femcock vs Vibrator Round 2

Clips4sale 1 year ago

My New Sissy Anal Slut

HD 0:10 / 25:13

My New Sissy Anal Slut

LoyalFans 2 years ago

Top Chef: The Ts Cock Challenge

Top Chef: The Ts Cock Challenge

Mel Fire and TS Frantiesca love to watch you cum when they decide so (engl-port)

Mel Fire and TS Frantiesca love to watch you cum when they decide so (engl-port)

Clips4sale 9 months ago

Nancy Thompson Foot Tickle & Chill 1080p MP4

Nancy Thompson Foot Tickle & Chill 1080p MP4

Clips4sale 9 months ago

Best Boys Only- Streaming Only

HD 0:10 / 14:43

Best Boys Only- Streaming Only

LoyalFans 4 months ago

Sucky Tekken battle : Futanari, ANAL, POV

Sucky Tekken battle : Futanari, ANAL, POV

LoyalFans 3 weeks ago

Vanessa vs JC: Arm Wrestling

58% 0:07 / 6:25

Vanessa vs JC: Arm Wrestling

Clips4sale 6 months ago

Ms. B Hydration Station Challenge!!

Ms. B Hydration Station Challenge!!

Clips4sale 3 months ago

Crossdresser Streamer Fail!

HD 0:11 / 10:08

Crossdresser Streamer Fail!

Clips4sale 3 years ago

Blonde Slender Slut Happy Ending in Her Mouth

66% HD 0:30 / 13:39

Blonde Slender Slut Happy Ending in Her Mouth

Clips4sale 3 years ago

BE A GOOD SUB

HD 0:10 / 11:55

LoyalFans 3 years ago

Exposed Sissy Challenge

Exposed Sissy Challenge

Clips4sale 3 years ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 MP4

HD 0:29 / 11:18

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 MP4

Clips4sale 2 years ago

Wedgie wrestling-mobile friendly

Wedgie wrestling-mobile friendly

Clips4sale 1 year ago

Teacher Hex’s practical class of biology with TS student girl Sophie (720p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

63% HD 0:32 / 56:20

Teacher Hex’s practical class of biology with TS student girl Sophie (720p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

Clips4sale 7 months ago

Stepmommys Dirtiest BBC Faggot

57% 0:21 / 11:40

Stepmommys Dirtiest BBC Faggot

Clips4sale 1 year ago

Ari's First Self-Fisting

HD 0:11 / 25:38

Ari's First Self-Fisting

Clips4sale 3 years ago

Dirt and Cream

Clips4sale 3 years ago

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves

HD 0:28 / 14:49

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves

Clips4sale 9 months ago

Suntanned Sissy (SD)

4K 0:49 / 21:55

Suntanned Sissy (SD)

Clips4sale 4 years ago

Suntanned Sissy (HD)

4K 0:49 / 21:55

Suntanned Sissy (HD)

Clips4sale 4 years ago

Shemale cock to cock wrestle and sexfight 720p

Shemale cock to cock wrestle and sexfight 720p

Clips4sale 1 year ago

SISSY STOCKINGS PANTYHOSE CUM CHALLENGE - Sissy Training, Sissy Sluts Training

SISSY STOCKINGS PANTYHOSE CUM CHALLENGE - Sissy Training, Sissy Sluts Training

Uninvited Slumber Party Guest 7 Written by Kylie Gable narrated by Shayla Aspasia

HD 0:30 / 40:44

Uninvited Slumber Party Guest 7 Written by Kylie Gable narrated by Shayla Aspasia

Clips4sale 1 year ago

Submissive BBW bimbo secretary becomes dominant FUTA CEO

Submissive BBW bimbo secretary becomes dominant FUTA CEO

Clips4sale 1 year ago

Earn the Strap: Jaq Quicksilver Pegs PonyBoyXXX featuring boot and leather worship, ass eating, and strap-on deepthroat - 1080p

HD 0:30 / 17:15

Earn the Strap: Jaq Quicksilver Pegs PonyBoyXXX featuring boot and leather worship, ass eating, and strap-on deepthroat - 1080p

Clips4sale 2 years ago

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session! - Jaq Quicksilver - strapon, game, ftm, praise - 1080p mp4

HD 0:29 / 12:14

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session! - Jaq Quicksilver - strapon, game, ftm, praise - 1080p mp4

Clips4sale 6 months ago

Hood Vibrator with Latex Layers - Mobile

HD 0:27 / 15:50

Hood Vibrator with Latex Layers - Mobile

Clips4sale 5 months ago

Futa cock to cock battle and fucking: Poolside Showdown 720p

Futa cock to cock battle and fucking: Poolside Showdown 720p

Clips4sale 6 months ago

Stepmommy's Dirtiest BBC Faggot

65% 0:21 / 11:40

Stepmommy's Dirtiest BBC Faggot

Clips4sale 1 year ago

Goddess JOI with Muscle worship and Latex ASMR

HD 0:10 / 11:22

Goddess JOI with Muscle worship and Latex ASMR

LoyalFans 1 month ago

Beautiful Post-Op Swallows My Seed

46% HD 0:30 / 13:39

Beautiful Post-Op Swallows My Seed

Clips4sale 3 years ago

Anal Stretching with Kalin - part 2

HD 0:57 / 20:38

Anal Stretching with Kalin - part 2

Clips4sale 4 years ago

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (STANDARD WMV)

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (STANDARD WMV)

Clips4sale 1 year ago

Rope Tied Oil Catfight and Trib Fight

61% 0:30 / 10:08

Rope Tied Oil Catfight and Trib Fight

Clips4sale 10 months ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

Clips4sale 1 year ago

Sissy Femboy Secretary Interview

61% 0:30 / 15:40

Sissy Femboy Secretary Interview

Clips4sale 1 year ago

Cocky gym-bro alpha dominates and humiliates you - Jaq Quicksilver - FtM Trans jock punishes you for being closeted with rough fucking - ft slapping, spitting, verbal humiliation, muscle worship, blowjob, pov fucking - 4k mp4

4K 0:30 / 12:29

Cocky gym-bro alpha dominates and humiliates you - Jaq Quicksilver - FtM Trans jock punishes you for being closeted with rough fucking - ft slapping, spitting, verbal humiliation, muscle worship, blowjob, pov fucking - 4k mp4

Clips4sale 1 year ago

Cursed Desires: Boy-Girl Transformation

59% 0:16 / 9:35

Cursed Desires: Boy-Girl Transformation

Clips4sale 2 years ago

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 720 MP4

HD 0:19 / 19:48

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 720 MP4

Clips4sale 2 years ago

Sissy Task Of The Day #4

Sissy Task Of The Day #4

LoyalFans 3 years ago

Sissy Karja in trouble (part: 'Selfbondage')

55% 0:11 / 8:18

Sissy Karja in trouble (part: 'Selfbondage')

Clips4sale 2 years ago

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 1080 MP4

HD 0:19 / 19:48

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 1080 MP4

Clips4sale 2 years ago

Edge for My Ass in Yoga Pants

66% 0:56 / 6:57

Edge for My Ass in Yoga Pants

HUGE MONSTERS CHALLENGE FOR THE SISSY SLUT

HUGE MONSTERS CHALLENGE FOR THE SISSY SLUT

Clips4sale 2 years ago

flawless and fantastic femboi

53% 0:11 / 27:13

flawless and fantastic femboi

Clips4sale 1 year ago

Slutty Faggot For BBC

Slutty Faggot For BBC

Clips4sale 3 years ago

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (STANDARD MP4)

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (STANDARD MP4)

Clips4sale 1 year ago

Beachball challenge

Beachball challenge

Clips4sale 1 year ago

Slut Faggot For BBC

Slut Faggot For BBC

Clips4sale 3 years ago

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! 720

HD 0:11 / 39:41

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! 720

Clips4sale 2 years ago

Futa Wife's Growing Bulge - 1080 WMV

HD 0:16 / 27:28

Futa Wife's Growing Bulge - 1080 WMV

Clips4sale 3 years ago

Sip, Sip Sissy!!!

Sip, Sip Sissy!!!

Clips4sale 2 months ago

Mrs Nara`s Femdom School - Class 04: Sissy Humiliation (1080 EN-sub)

66% HD 0:35 / 11:19

Mrs Nara`s Femdom School - Class 04: Sissy Humiliation (1080 EN-sub)

Clips4sale 2 years ago

Sissy Shopping Challenge

Sissy Shopping Challenge

LoyalFans 2 years ago

Caged, Fingered, and Left Bound for The Night

Caged, Fingered, and Left Bound for The Night

Clips4sale 1 year ago

Sex and Head Dunks! Anal + Creampie POV

64% 0:54 / 20:17

Sex and Head Dunks! Anal + Creampie POV

Clips4sale 1 year ago

Delia Releases a Kept Man From Chastity Then Locks Him Down with Her Cock!

Delia Releases a Kept Man From Chastity Then Locks Him Down with Her Cock!

C4S 2 years ago

Sissy Photoshoot Challenge

HD 0:25 / 11:34

Sissy Photoshoot Challenge

Clips4sale 2 years ago

TGirl Nancy and Catherine TESTS OF STRENGTH HIDEF

HD 0:15 / 10:02

TGirl Nancy and Catherine TESTS OF STRENGTH HIDEF

Clips4sale 1 year ago

Hazel and her transgirlfriend Tillie play with the guys

Hazel and her transgirlfriend Tillie play with the guys

Clips4sale 1 year ago

Cocky gym-bro alpha dominates and humiliates you - Jaq Quicksilver - FtM Trans jock punishes you for being closeted with rough fucking - ft slapping, spitting, verbal humiliation, muscle worship, blowjob, pov fucking - 1080p mp4

52% HD 0:30 / 12:30

Cocky gym-bro alpha dominates and humiliates you - Jaq Quicksilver - FtM Trans jock punishes you for being closeted with rough fucking - ft slapping, spitting, verbal humiliation, muscle worship, blowjob, pov fucking - 1080p mp4

Clips4sale 1 year ago

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves (720p)

HD 0:28 / 14:49

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves (720p)

Clips4sale 9 months ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 5 OF 5 - MP4

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 5 OF 5 - MP4

Clips4sale 11 months ago

Futa Story: Insubordination - Ft Imilia Audley

4K 0:29 / 12:27

Futa Story: Insubordination - Ft Imilia Audley

Clips4sale 1 year ago

Week 22: A Naughty Task for Sissy Sluts (MP4)

Week 22: A Naughty Task for Sissy Sluts (MP4)

Clips4sale 2 years ago

Mrs Nara`s Femdom School - Class 04: Sissy Humiliation (720 EN-sub)

HD 0:35 / 11:19

Mrs Nara`s Femdom School - Class 04: Sissy Humiliation (720 EN-sub)

Clips4sale 2 years ago

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