Sissy Dress Up Videos (964)

Crossdresser Dirk - I Suck a Big Dick and Swallow All

68% 0:39 / 10:39

Crossdresser Dirk - I Suck a Big Dick and Swallow All

FapHouse 6 months ago

Crossdresser Dirk - I Suck a Big Dick and Swallow All

77% 1:01 / 10:39

Crossdresser Dirk - I Suck a Big Dick and Swallow All

FapHouse 6 months ago

The Gay Awakening Podcast Episode #35

71% HD 0:20 / 10:49

The Gay Awakening Podcast Episode #35

Clips4sale 3 years ago

Playing with Myself

Playing with Myself

FapHouse 10 months ago

TRUCK STOP FAGGOT

34% HD 0:10 / 10:45

TRUCK STOP FAGGOT

LoyalFans 3 years ago

My BBC for you and your wife, sissy cuck! 28 min (MaleDom)

50% HD 0:30 / 27:46

My BBC for you and your wife, sissy cuck! 28 min (MaleDom)

Clips4sale 1 year ago

Feminization Fashion Show Training Part 1

69% HD 0:15 / 18:07

Feminization Fashion Show Training Part 1

Clips4sale 5 years ago

Your Slutty Sissy Fantasy

HD 0:21 / 20:05

Your Slutty Sissy Fantasy

Clips4sale 4 months ago

YOUR LAS VEGAS GLORYHOLE BACHELORETTE PARTY

Premium 4K 9:06

YOUR LAS VEGAS GLORYHOLE BACHELORETTE PARTY

Clips4sale 2 years ago

Lingerie Slut Gets Fucked in Heels by 10 BBC

53% 1:01 / 36:18

Lingerie Slut Gets Fucked in Heels by 10 BBC

FapHouse 7 months ago

Lingerie Slut Gets Fucked in Heels by 10 BBC

69% 0:39 / 36:18

Lingerie Slut Gets Fucked in Heels by 10 BBC

FapHouse 7 months ago

The Monstercock - 11 Inch for the Whore

63% HD 0:39 / 11:03

The Monstercock - 11 Inch for the Whore

FapHouse 3 months ago

Another Milestone Meet!!

HD 0:39 / 11:43

Another Milestone Meet!!

FapHouse 1 year ago

Dress Up Group Breeding

61% HD 0:27 / 17:53

Dress Up Group Breeding

Clips4sale 1 year ago

Horny Femboy Big Ass Takes BBC Cum Eating

54% HD 1:01 / 38:33

Horny Femboy Big Ass Takes BBC Cum Eating

FapHouse 2 years ago

Trucker step-Daddy Loves Diaper Sissy

51% HD 0:10 / 27:41

Trucker step-Daddy Loves Diaper Sissy

LoyalFans 1 year ago

Sissy Stuffing Perverted Tasks for Feminization Gay Training

Sissy Stuffing Perverted Tasks for Feminization Gay Training

FapHouse 1 month ago

Mezmerized into Sissy Slut Whore 720p WMV - Toms Fetish Store

Mezmerized into Sissy Slut Whore 720p WMV - Toms Fetish Store

Clips4sale 2 years ago

Husband Faggot Sissy BBC Cock Lover

HD 0:15 / 19:35

Husband Faggot Sissy BBC Cock Lover

IWantClips 8 years ago

SISSY FAGGOT TRANCE

HD 0:11 / 21:34

SISSY FAGGOT TRANCE

Clips4sale 3 years ago

SISSY SLUT BLACKED IN THE ALLEY - PART 1

57% HD 0:10 / 17:41

SISSY SLUT BLACKED IN THE ALLEY - PART 1

LoyalFans 2 years ago

No Choice SissyGasm-Sissy Training-Assignments-Tasks

55% HD 0:11 / 17:52

No Choice SissyGasm-Sissy Training-Assignments-Tasks

Clips4sale 4 years ago

Horny Femboy Big Ass Takes BBC Cum Eating

57% HD 0:39 / 38:33

Horny Femboy Big Ass Takes BBC Cum Eating

FapHouse 2 years ago

Flip Flops Show

59% HD 2:00 / 27:25

Flip Flops Show

Flirt4Free 1 year ago

The Monstercock - 11 Inch for the Whore

69% HD 1:01 / 11:03

The Monstercock - 11 Inch for the Whore

FapHouse 3 months ago

Lingerie Slut Gets Fucked in Heels by 10 BBC

55% 0:39 / 36:18

Lingerie Slut Gets Fucked in Heels by 10 BBC

FapHouse 7 months ago

Thongs and Dildos

67% HD 2:00 / 19:00

Thongs and Dildos

Flirt4Free 1 year ago

Stepdaddys Favorite Lingerie

45% 0:39 / 12:36

Stepdaddys Favorite Lingerie

FapHouse 7 months ago

A Man Dressed as a Prostitute Appeared in a Movie Theater in Tokyo.

53% HD 0:39 / 0:50

A Man Dressed as a Prostitute Appeared in a Movie Theater in Tokyo.

FapHouse 6 months ago

A Man Dressed as a Prostitute Appeared in a Movie Theater in Tokyo.

56% HD 0:39 / 0:50

A Man Dressed as a Prostitute Appeared in a Movie Theater in Tokyo.

FapHouse 6 months ago

Lingerie Slut Gets Fucked in Heels by 10 BBC

57% 0:39 / 36:18

Lingerie Slut Gets Fucked in Heels by 10 BBC

FapHouse 7 months ago

COCK FILLED WHORE (1080p)

67% HD 0:22 / 12:23

COCK FILLED WHORE (1080p)

Clips4sale 1 year ago

Femboy Rosalina Corset & Love Anal

55% HD 1:01 / 21:05

Femboy Rosalina Corset & Love Anal

FapHouse 1 year ago

Giantess Feminization!

74% HD 0:39 / 11:12

Giantess Feminization!

FapHouse 3 years ago

Sexy Dance Vibes in White - Lunar Body (full)

Sexy Dance Vibes in White - Lunar Body (full)

FapHouse 3 days ago

Thick Climax in my Nylons and Golden High Heels

67% HD 0:39 / 6:37

Thick Climax in my Nylons and Golden High Heels

FapHouse 10 months ago

I will make you crossdress, sissy, and suck cock for me!

I will make you crossdress, sissy, and suck cock for me!

Clips4sale 4 years ago

Horny PVC college girl Rosalina, cosplay-trap

HD 0:39 / 28:46

Horny PVC college girl Rosalina, cosplay-trap

FapHouse 4 years ago

Feminized For The BNWO (HD MP4)

52% 4K 0:32 / 16:06

Feminized For The BNWO (HD MP4)

Clips4sale 2 years ago

Cross Dressing Lingerie Lesson -mp4

Cross Dressing Lingerie Lesson -mp4

Clips4sale 8 months ago

The pink sissy bimbofication

HD 0:38 / 10:08

The pink sissy bimbofication

Clips4sale 6 days ago

Be More Bi This Goddess of 2026 Alexa, Femdom Animated by Bi

Be More Bi This Goddess of 2026 Alexa, Femdom Animated by Bi

FapHouse 9 months ago

Sissification Fashion Show After Party Makeover by Bellatrix Bandit

54% 0:15 / 23:33

Sissification Fashion Show After Party Makeover by Bellatrix Bandit

Clips4sale 5 years ago

gottaluvbb getting caged up and dressed up to go out

63% HD 0:27 / 9:20

gottaluvbb getting caged up and dressed up to go out

PornBox 24 years ago

Tall Bodybuilder in Small Underwear Tied Up

HD 2:00 / 44:37

Tall Bodybuilder in Small Underwear Tied Up

Flirt4Free 9 years ago

Pigtails Pulled As Your Sissy Virginity Is Taken By The Team

HD 0:38 / 15:04

Pigtails Pulled As Your Sissy Virginity Is Taken By The Team

Clips4sale 7 months ago

Your Clitty Belongs In Panties

Your Clitty Belongs In Panties

LoyalFans 3 years ago

Feminized For The BNWO (4KUHD MP4)

60% HD 0:32 / 16:06

Feminized For The BNWO (4KUHD MP4)

Clips4sale 2 years ago

Muscled Slut in Lingerie Takes My Hung Cock and My Fist Deep

66% 0:39 / 19:34

Muscled Slut in Lingerie Takes My Hung Cock and My Fist Deep

FapHouse 3 months ago

Pigtails Pulled As Your Sissy Virginity Is Taken By The Team (HD MP4)

4K 0:38 / 15:04

Pigtails Pulled As Your Sissy Virginity Is Taken By The Team (HD MP4)

Clips4sale 7 months ago

Say Super-Gay Things Until You Sissygasm (4KUHD MP4)

63% HD 0:30 / 15:09

Say Super-Gay Things Until You Sissygasm (4KUHD MP4)

Clips4sale 2 years ago

Kandi's Cock Sucking Control Game

Kandi's Cock Sucking Control Game

LoyalFans 10 months ago

SISSY SLUT BLACKED IN THE ALLEY: PART 3 - THE BLACK MANS ASS

HD 0:10 / 19:18

SISSY SLUT BLACKED IN THE ALLEY: PART 3 - THE BLACK MANS ASS

LoyalFans 2 years ago

Crowned Anal Princess

Crowned Anal Princess

LoyalFans 2 years ago

EXPOSING SLUT MICHELLE

63% HD 0:10 / 10:41

EXPOSING SLUT MICHELLE

LoyalFans 3 years ago

Ai Salon Sucker

55% HD 0:10 / 7:18

Ai Salon Sucker

LoyalFans 3 years ago

LUDOVICA LUXURY -THE SISSY WHORE ON DUTY -hd

51% HD 0:15 / 19:16

LUDOVICA LUXURY -THE SISSY WHORE ON DUTY -hd

Clips4sale 1 year ago

Kandi's Cock Sucking Control Game

Kandi's Cock Sucking Control Game

LoyalFans 3 weeks ago

Womanless Pageant Saga- Getting a BF

61% HD 0:11 / 13:54

Womanless Pageant Saga- Getting a BF

Clips4sale 4 years ago

Sissy Pride: Bitch in Heat, Pride in Knees -SISSIFICATION, TASK

68% HD 0:10 / 10:21

Sissy Pride: Bitch in Heat, Pride in Knees -SISSIFICATION, TASK

LoyalFans 1 year ago

You Are A Sissy In Permanent Chastity

HD 0:20 / 10:29

You Are A Sissy In Permanent Chastity

Clips4sale 2 years ago

I'm Going to Make You Be the Other Girl in Our FFM 3-Way [POV Erotic Audio] ***MP3 Version***

I'm Going to Make You Be the Other Girl in Our FFM 3-Way [POV Erotic Audio] ***MP3 Version***

Clips4sale 1 year ago

Sissy boy Jaden is all worked up in his diapers and little pink skirt, but will he be allowed to cum???

Sissy boy Jaden is all worked up in his diapers and little pink skirt, but will he be allowed to cum???

Clips4sale 2 years ago

Surprise Ass-Pussy Inspection [POV Erotic Audio] ***MP3***

Surprise Ass-Pussy Inspection [POV Erotic Audio] ***MP3***

Clips4sale 1 year ago

Soft Touch Sissy Encouragement

51% 4K 0:29 / 20:33

Soft Touch Sissy Encouragement

Clips4sale 1 year ago

Mistress Sophia Sahara Bi Training

50% 0:26 / 17:03

Mistress Sophia Sahara Bi Training

Clips4sale 4 years ago

Non-Binary FatFemmeDaddy Wants you to Suck Their Big GAY Cock *WMV

66% 0:30 / 9:53

Non-Binary FatFemmeDaddy Wants you to Suck Their Big GAY Cock *WMV

Clips4sale 4 years ago

Sissy Wife Eats My Bull's Cum Out of My Panties

HD 0:10 / 11:29

Sissy Wife Eats My Bull's Cum Out of My Panties

LoyalFans 4 months ago

Rubber Slut Sucks

Rubber Slut Sucks

Clips4sale 7 months ago

Turned Into A Bitch Then Stuff You With BBC

Turned Into A Bitch Then Stuff You With BBC

Clips4sale 2 weeks ago

Caught Crossdressing SISSIFICATION FEMDOM GF (wmv)

Caught Crossdressing SISSIFICATION FEMDOM GF (wmv)

Clips4sale 1 month ago

Nylon Sissy Slave - Candle Boxxx HDMP4

35% 0:14 / 13:03

Nylon Sissy Slave - Candle Boxxx HDMP4

Clips4sale 3 years ago

Gay Hookup App Cheating Sissy Confession - Jessica Dynamic

Gay Hookup App Cheating Sissy Confession - Jessica Dynamic

Clips4sale 2 years ago

Sissy CD Party Dress, Corset, Heels & Cum on My Stockings

67% HD 1:01 / 37:16

Sissy CD Party Dress, Corset, Heels & Cum on My Stockings

FapHouse 1 year ago

Dance For Men (SD MP4)

4K 0:30 / 15:44

Dance For Men (SD MP4)

Clips4sale 1 year ago

Sexy Maid Boy Has Fun with His Dick for You

HD 0:39 / 11:54

Sexy Maid Boy Has Fun with His Dick for You

FapHouse 1 year ago

Sissy Boy Stuck In Diaper World With Sora

Premium HD 15:06

Sissy Boy Stuck In Diaper World With Sora

Clips4sale 1 week ago

Boys Caught Smoking Get Put over the Knee

66% 4K 2:00 / 6:20

Boys Caught Smoking Get Put over the Knee

Flirt4Free 3 years ago

So You Want to Be a Sissy?

HD 1:01 / 12:12

So You Want to Be a Sissy?

FapHouse 1 week ago

Begging for Your Cum! a JOI for Superior Daddies!

Begging for Your Cum! a JOI for Superior Daddies!

FapHouse 1 year ago

Dressed Like a Whore I Ride the Dildo, Gaping My Ass with the Huge Plug and Cum When Hands Free

Dressed Like a Whore I Ride the Dildo, Gaping My Ass with the Huge Plug and Cum When Hands Free

FapHouse 1 week ago

White Shiny Stockings and Big Toy

White Shiny Stockings and Big Toy

FapHouse 6 months ago

You're My Fucking Property - REMASTERED - Loser Degradation Slave Induction Femdom POV

You're My Fucking Property - REMASTERED - Loser Degradation Slave Induction Femdom POV

LoyalFans 2 years ago

Tied Eggs and Cock with TV Plug Wearing Pantyhose

Tied Eggs and Cock with TV Plug Wearing Pantyhose

FapHouse 3 years ago

Two Huge Dildoes!!

Two Huge Dildoes!!

FapHouse 6 days ago

Stepdaddys Favorite Lingerie

38% 1:01 / 12:36

Stepdaddys Favorite Lingerie

FapHouse 7 months ago

Sissy Shopping Spree Part 2

Sissy Shopping Spree Part 2

Clips4sale 4 years ago

Non-Binary FatFemmeDaddy Wants you to Suck Their Big GAY Cock *MP4

50% HD 0:30 / 9:54

Non-Binary FatFemmeDaddy Wants you to Suck Their Big GAY Cock *MP4

Clips4sale 4 years ago

Cucked And Clowned

HD 0:17 / 13:09

Cucked And Clowned

IWantClips 3 years ago

Stepmother in lingerie Trims Horny hairy cock of Kneeling Crossdresser in Stockings - Humiliation Conversations a Slut, Amateur Couple Home Video, Bisexual Encouragement, Close Female Naked Male, Femdom, Gentle Discipline

46% 4K 0:23 / 11:38

Stepmother in lingerie Trims Horny hairy cock of Kneeling Crossdresser in Stockings - Humiliation Conversations a Slut, Amateur Couple Home Video, Bisexual Encouragement, Close Female Naked Male, Femdom, Gentle Discipline

Clips4sale 8 months ago

LUDOVICA LUXURY -THE SISSY WHORE ON DUTY -mobile

66% 0:15 / 19:16

LUDOVICA LUXURY -THE SISSY WHORE ON DUTY -mobile

Clips4sale 1 year ago

Truck Stop Sissy Faggot Slut

HD 0:10 / 10:03

Truck Stop Sissy Faggot Slut

LoyalFans 7 months ago

The Gay Awakening Podcast Episode #63 - A Sissy Dilemma

45% HD 0:25 / 16:48

The Gay Awakening Podcast Episode #63 - A Sissy Dilemma

Clips4sale 2 years ago

Supervised Sissy Sample Rejected (HD MP4)

4K 0:31 / 15:47

Supervised Sissy Sample Rejected (HD MP4)

Clips4sale 2 years ago

Businessman in a Chastity Cage Is Getting Fucked by the Sex Machine

Businessman in a Chastity Cage Is Getting Fucked by the Sex Machine

FapHouse 11 months ago

Gaylocked (HD MP4)

62% 4K 0:30 / 16:12

Gaylocked (HD MP4)

Clips4sale 1 year ago

Gay Sissy Bet

60% HD 0:26 / 8:28

Clips4sale 5 years ago

Sissy Cellmates (4KUHD MP4)

Premium HD 12:24

Sissy Cellmates (4KUHD MP4)

Clips4sale 1 month ago

Twink Dressed up as a Bride and Offered Her Sweet Little Ass in a Hot Gangbang.

42% HD 1:01 / 10:15

Twink Dressed up as a Bride and Offered Her Sweet Little Ass in a Hot Gangbang.

FapHouse 10 months ago

Sissy Pride: Bitch in Heat, Pride in Knees - Sissification, Task

HD 1:01 / 10:25

Sissy Pride: Bitch in Heat, Pride in Knees - Sissification, Task

FapHouse 1 year ago

Ur sissy again outdoors enjoying her toys and cuming

51% HD 1:01 / 21:37

Ur sissy again outdoors enjoying her toys and cuming

FapHouse 3 years ago

Caged Femboy Frieren Fucks Ass and Cums in Chastity

Caged Femboy Frieren Fucks Ass and Cums in Chastity

FapHouse 1 month ago

Say Super-Gay Things Until You Sissygasm (HD MP4)

57% 4K 0:30 / 15:09

Say Super-Gay Things Until You Sissygasm (HD MP4)

Clips4sale 2 years ago

Lee Przybylowicz Feeling Extra Slutty and Dirty

Lee Przybylowicz Feeling Extra Slutty and Dirty

FapHouse 3 weeks ago

Dressed Like a Whore I Ride the Dildo, Gaping My Ass with the Huge Plug and Cum When Hands Free

Dressed Like a Whore I Ride the Dildo, Gaping My Ass with the Huge Plug and Cum When Hands Free

FapHouse 1 week ago

Feminised, Humiliated And Teased In Chain Bondage (4K)

67% 4K 0:22 / 18:18

Feminised, Humiliated And Teased In Chain Bondage (4K)

Clips4sale 1 year ago

Crowned Anal Princess

Crowned Anal Princess

Clips4sale 2 weeks ago

BIMBONOSIS

Clips4sale 3 years ago

The Gay Awakening Podcast Episode #15

48% HD 0:24 / 15:16

The Gay Awakening Podcast Episode #15

Clips4sale 3 years ago

Bi Training 101: Two Goddesses Repurpose Straight Cuck into Cock Slut with Double Strap-On Mouth and Ass Destruction [4K UHD]

4K 0:30 / 12:34

Bi Training 101: Two Goddesses Repurpose Straight Cuck into Cock Slut with Double Strap-On Mouth and Ass Destruction [4K UHD]

Clips4sale 6 months ago

Ai Salon Sucker

Ai Salon Sucker

Clips4sale 3 years ago

Sissy Cellmates (SD MP4)

HD 0:25 / 12:24

Sissy Cellmates (SD MP4)

Clips4sale 1 month ago

Cage Creaming Accidents - Mean Permanent Chastity Sissygasms (4KUHD MP4)

HD 0:41 / 18:00

Cage Creaming Accidents - Mean Permanent Chastity Sissygasms (4KUHD MP4)

Clips4sale 6 months ago

Suggesting You Need Bullies

Suggesting You Need Bullies

LoyalFans 3 years ago

Cum For Me Sissy Slut Hole Introduction - Twink - Sissy Girl - Crossdressing - Femboy - Cock Lover

Cum For Me Sissy Slut Hole Introduction - Twink - Sissy Girl - Crossdressing - Femboy - Cock Lover

Clips4sale 4 months ago

SISSY SLUT BIMBO MESMERIZE

59% HD 0:10 / 13:20

SISSY SLUT BIMBO MESMERIZE

LoyalFans 2 years ago

Caught Crossdressing SISSIFICATION FEMDOM GF (mp4)

63% HD 0:13 / 7:35

Caught Crossdressing SISSIFICATION FEMDOM GF (mp4)

Clips4sale 1 month ago

Be More Bi This Goddess of 2026 Alexa, Femdom Animated by Bi

Be More Bi This Goddess of 2026 Alexa, Femdom Animated by Bi

FapHouse 9 months ago

Diversity Drive (SD MP4)

4K 0:30 / 15:26

Diversity Drive (SD MP4)

Clips4sale 1 year ago

Sexy Dance Vibes in White - Lunar Body (full)

Sexy Dance Vibes in White - Lunar Body (full)

FapHouse 3 days ago

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964 results found

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