Sissy Crossdressing

Glamour babe pissdrenched by crossdresser
10:00 Glamour babe pissdrenched by crossdresser Tags: Blowjob, Babe, Fetish, Fingering, Oral, Pissing, Glamour 7 years ago Upornia
Amazing interracial vintage scene with Rik Taziner and Paul Thomas
01:08:17 Amazing interracial vintage scene with Rik Taziner and Paul Thomas Tags: Blowjob, Black, Interracial, Wife, Interracial Blowjob, Vintage, Kinky 7 years ago TubePornClassic
Punished and fucked in my sissy fuck hole
12:08 Punished and fucked in my sissy fuck hole Tags: Ass, Anal, Femdom, Strap-on, Moaning, Husband, Humiliation 7 years ago PornHub
Sissy fucked by toys
02:39 Sissy fucked by toys Tags: Toys, Butt, Sissy 7 years ago PornHub
Sissy Love 3 [PMV]
06:37 Sissy Love 3 [PMV] Tags: Amateur, Sissy 7 years ago PornHub
Humiliating Sissy Slut Murray Chapman
00:32 Humiliating Sissy Slut Murray Chapman Tags: Slut, BDSM, Humiliation, Sissy 7 years ago PornHub
Slutty Sissy Shay Double Sissygasm in Chastity!
06:55 Slutty Sissy Shay Double Sissygasm in Chastity! Tags: Amateur, Ass, Anal, Toys, Orgasm, Slut, Dildo 7 years ago PornHub
Sissy Feivel masturbates and cums on cam
10:05 Sissy Feivel masturbates and cums on cam Tags: Teen (18/19), Solo, Cum, Webcam, Sissy 7 years ago PornHub
Sissies Love Poppers
06:37 Sissies Love Poppers Tags: Petite, Shemale, Tranny, Sissy, Ladyboy 7 years ago PornHub
Sissy fucked by curious straight guy
00:46 Sissy fucked by curious straight guy Tags: Pussy, Ass, Anal, POV (Point Of View), Latina, Lingerie, Tight 7 years ago PornHub
Sissy Becky Dildos Her Ass & Shoots Cum Load
10:59 Sissy Becky Dildos Her Ass & Shoots Cum Load Tags: Ass, Cum, Tight, Assfucking, Sissy 7 years ago PornHub
sissy in fishnets works her dildo
02:13 sissy in fishnets works her dildo Tags: Dildo, Sissy 7 years ago PornHub
Sissy Secretary ties up & blindfolds boss for blowjob
08:39 Sissy Secretary ties up & blindfolds boss for blowjob Tags: Blowjob, Handjob, Bondage, Slave, Hidden Cam, Boss, Secretary 7 years ago PornHub
SLUTTY SISSY COCKSUCKER #3
02:46 SLUTTY SISSY COCKSUCKER #3 Tags: Amateur, Cumshot, Slut, Rimjob, Bimbo, Sissy 7 years ago PornHub
Sissy Ass Workout & body Showing In Booty Shorts
03:32 Sissy Ass Workout & body Showing In Booty Shorts Tags: Amateur, Ass, Legs, Booty, Shorts, Sissy, Workout 7 years ago PornHub
Anal Crossdressing
02:50 Anal Crossdressing Tags: Ass, Anal, Toys, Stockings, Mature, Dildo, Assfucking 7 years ago PornHub
Sissy likes it rough
08:53 Sissy likes it rough Tags: Anal, Slut, Rough, Rough Anal Sex, Sissy 7 years ago PornHub
Sissy punished
15:48 Sissy punished Tags: Anal, Rough, Bondage, Rough Anal Sex, Punishment, Sissy 7 years ago PornHub
Sissy sucks cock for cum
05:00 Sissy sucks cock for cum Tags: Blowjob, Dick, Cum, Blowjob & Cum, Facial, Sissy 7 years ago PornHub
Sissy gets rough deepthroat
08:24 Sissy gets rough deepthroat Tags: Blowjob, Cum, Blowjob & Cum, Deepthroat, Rough, Gagging, Sissy 7 years ago PornHub
Sissy fucked hard
05:04 Sissy fucked hard Tags: Anal, Slut, Creampie, Rough, Whore, Rough Anal Sex, Sissy 7 years ago PornHub
Sissy used outdoors
02:59 Sissy used outdoors Tags: Anal, Facial, Slut, Rough, Whore, Rough Anal Sex, Sissy 7 years ago PornHub
Sissy takes huge toys
10:23 Sissy takes huge toys Tags: Anal, Toys, Sissy 7 years ago PornHub
SissyThai Student Slave Fucking Dildo and Cum with no hand
36:32 SissyThai Student Slave Fucking Dildo and Cum with no hand Tags: Ass, Toys, Asian, Cum, Fucking, Orgasm, Dildo 7 years ago PornHub
Asian Teen Crossdresser Twerk
00:49 Asian Teen Crossdresser Twerk Tags: Ass, Teen (18/19), Young (18-25), Asian, Booty, Asian Teen (18/19), Shorts 7 years ago PornHub
Sexy sissy trap fucked
06:08 Sexy sissy trap fucked Tags: Blowjob, Anal, Creampie, Sissy 7 years ago PornHub
Sissy cunt stuffed
02:09 Sissy cunt stuffed Tags: Anal, Slut, Rough, Cunt, Whore, Rough Anal Sex, Sissy 7 years ago PornHub
sissy
08:06 sissy Tags: Sissy 7 years ago PornHub
Are you ready to take daddy's cock, sissy? (PMV)
05:57 Are you ready to take daddy's cock, sissy? (PMV) Tags: Dick, Anal, POV (Point Of View), Compilation, Shemale, POV Anal Sex, Anal Compilation 7 years ago PornHub
Goth sissy slut fucks herself
07:17 Goth sissy slut fucks herself Tags: Cum, Slut, Sissy, Goth, Femboy 7 years ago PornHub
Be a mindless sissy toy by hotblackmaledotcom
04:34 Be a mindless sissy toy by hotblackmaledotcom Tags: Fetish, Femdom, Sissy, Feminization 7 years ago PornHub
Sissy Spy Torture-trailer
00:32 Sissy Spy Torture-trailer Tags: Fucking, Slut, BDSM, Femdom, Strap-on, Domination, Torture (BDSM) 7 years ago PornHub
blonde sissy whore cumming all over herself
14:52 blonde sissy whore cumming all over herself Tags: Blonde, Whore, Sissy 7 years ago PornHub
BBW Sissy Diane Stripping
04:45 BBW Sissy Diane Stripping Tags: BBW, Stripping, Sissy 7 years ago PornHub
MySissySlut27 2
46:53 MySissySlut27 2 Tags: Ass, Webcam, Sissy, Instruction 7 years ago PornHub
Sissy riding a big dildo
01:07 Sissy riding a big dildo Tags: Ass, Anal, Dildo, Riding, Sissy 7 years ago PornHub
Sissy plays with penis pump
02:38 Sissy plays with penis pump Tags: Dick, Solo, Lingerie, Masturbating, Sissy, Penis Pump 7 years ago PornHub
MySissySlut27 4
39:38 MySissySlut27 4 Tags: Ass, Webcam, Sissy 7 years ago PornHub
sissy crossdresser toys ass
01:12 sissy crossdresser toys ass Tags: Amateur, Ass, Anal, Toys, Homemade, Dildo, Amateur Anal Sex 7 years ago PornHub
Testing my sissy hole
00:46 Testing my sissy hole Tags: Pussy, Ass, Solo, Young (18-25), Panties, Dildo, White 7 years ago PornHub
Tear my sissy pussy
18:18 Tear my sissy pussy Tags: Pussy, Ass, Cum, Tranny, Sissy, Cum In Ass 7 years ago PornHub
Sissy crossdresser smoking on webcam and anal toys
04:12 Sissy crossdresser smoking on webcam and anal toys Tags: Amateur, Anal, Toys, Webcam, Slut, Amateur Anal Sex, Smoking 7 years ago PornHub
Femdom Sissy Silgirl
09:33 Femdom Sissy Silgirl Tags: Femdom, Sissy 7 years ago PornHub
Femdom Sissy Maid caned
09:46 Femdom Sissy Maid caned Tags: Femdom, Maid, Sissy 7 years ago PornHub
teen crossdresser
02:09 teen crossdresser Tags: Teen (18/19), Sissy 7 years ago PornHub
sissy crossdresser
01:39 sissy crossdresser Tags: Femdom, Sissy 7 years ago PornHub
sissy crossdresser lingerie
01:23 sissy crossdresser lingerie Tags: Lingerie, Femdom, Sissy 7 years ago PornHub
sissy crossdresser amateur
01:22 sissy crossdresser amateur Tags: Amateur, Femdom, Sissy 7 years ago PornHub
Sub sissy Dizzy In Bondage
00:44 Sub sissy Dizzy In Bondage Tags: BDSM, Bondage, Tied Up, Humiliation, Transsexual, Tranny, Submissive 7 years ago PornHub
Sissy Panty Slut Fucks Huge Toy, Squirts Nasty Creampie
00:49 Sissy Panty Slut Fucks Huge Toy, Squirts Nasty Creampie Tags: Slut, Creampie, Dildo, Sissy, Huge Dildo, Huge Toy 7 years ago PornHub
My sissy slut sucks cum of black dilldo
01:10 My sissy slut sucks cum of black dilldo Tags: Dick, Cumshot, Cum, Black, Slut, BBC (Big Black Cock), Black Cock 7 years ago PornHub
2nd video: Sissy Faggot Gabriel Radu
02:55 2nd video: Sissy Faggot Gabriel Radu Tags: Amateur, Outdoor, Public, Sissy 7 years ago PornHub
Sissy Crossdresser plays with his big cock
01:33 Sissy Crossdresser plays with his big cock Tags: Amateur, Dick, Big Cock, Shemale, Miniskirt, Skirt, Bisexual 7 years ago PornHub
Sissy showing off
02:49 Sissy showing off Tags: Stripping, Tranny, Sissy 7 years ago PornHub
Kidnapped Crossdresser in blue Le. Massaged dirty and obscenely in hotel
02:44 Kidnapped Crossdresser in blue Le. Massaged dirty and obscenely in hotel Tags: Amateur, Massage, Dirty, Hotel, Sissy 7 years ago PornHub
My sexy sissy in chastity playing
04:36 My sexy sissy in chastity playing Tags: Anal, Sissy 7 years ago PornHub
Cumshot Tribute as a Crossdresser Sissy in Fishnet With My 12cm High Heels
03:12 Cumshot Tribute as a Crossdresser Sissy in Fishnet With My 12cm High Heels Tags: Cumshot, Cum, Stockings, High Heels, Pretty, Foot Fetish, Shemale 7 years ago PornHub
sissy amateur
02:54 sissy amateur Tags: Amateur, Femdom, Sissy 7 years ago PornHub
sissy amateur
02:50 sissy amateur Tags: Amateur, Femdom, Sissy 7 years ago PornHub
E-v-e crossdresser cam
09:52 E-v-e crossdresser cam Tags: Amateur, Anal, Toys, Webcam, Orgasm, Dildo, Feet 7 years ago PornHub
Slutty Crossdressing Whore Skype Show
10:00 Slutty Crossdressing Whore Skype Show Tags: Webcam, Slut, Homemade, Dildo, Whore, Transsexual, Tranny 7 years ago PornHub
MySissyMaid
09:59 MySissyMaid Tags: Webcam, Sissy 7 years ago PornHub
MySissySara
16:50 MySissySara Tags: Webcam, Sissy 7 years ago PornHub
sissy crossdresser
01:22 sissy crossdresser Tags: Femdom, Sissy 7 years ago PornHub
Sissy Simone Slutty Smoke Tease
01:51 Sissy Simone Slutty Smoke Tease Tags: Slut, Whore, Smoking, Tranny, Bimbo, Sissy 7 years ago PornHub
jerijames75 xxx sissy abc
01:22 jerijames75 xxx sissy abc Tags: Amateur, Sissy 7 years ago PornHub
Crossdressing Escort gives head, gets fucked, and ass filled with cum
10:07 Crossdressing Escort gives head, gets fucked, and ass filled with cum Tags: Blowjob, Ass, Anal, Cum, Blowjob & Cum, Sissy, Femboy 7 years ago PornHub
Brunette crossdresser sucks, get fucked, and receives a facial
55:24 Brunette crossdresser sucks, get fucked, and receives a facial Tags: Blowjob, Amateur, Brunette, Anal, Facial, Amateur Blowjob, Homemade 7 years ago PornHub
Craigslist stranger Sucked by Sissy Slut Annie Trappington SHEMALE TRANNY
02:59 Craigslist stranger Sucked by Sissy Slut Annie Trappington SHEMALE TRANNY Tags: Blowjob, Amateur, Dick, Big Cock, Amateur Blowjob, Slut, Shemale 7 years ago PornHub
Sissy CD Kayla playing with toy
07:44 Sissy CD Kayla playing with toy Tags: Pussy, Butt, Stockings, Slut, Dildo, Miniskirt, Fishnet 7 years ago PornHub
Sissy Intro
02:07 Sissy Intro Tags: Humiliation, Sissy, Intro 7 years ago PornHub
Sultry Goddess Paddles Sissy Maid
07:17 Sultry Goddess Paddles Sissy Maid Tags: Amateur, Ass, BDSM, Wife, Bondage, Femdom, French 7 years ago PornHub
Sissyboy dancing
01:03 Sissyboy dancing Tags: Dancing, Sissy 7 years ago PornHub
Hot Sissy Schoolgirl Give Huge Self Facial & Swallow Own Cum
06:20 Hot Sissy Schoolgirl Give Huge Self Facial & Swallow Own Cum Tags: Amateur, Cum, POV (Point Of View), Facial, Handjob, Homemade, Cum In Mouth 7 years ago PornHub
Sexy Crossdresser Hard Fucked from Behind by Dominating Masked Man
03:59 Sexy Crossdresser Hard Fucked from Behind by Dominating Masked Man Tags: Hardcore, Ass, Anal, Doggystyle, Rough, Romantic, Rough Anal Sex 7 years ago PornHub
Mj Sissy - Secret Sissy (HD)
05:45 Mj Sissy - Secret Sissy (HD) Tags: HD, Slut, Gangbang, Shemale, Sissy, VR (Virtual Reality), Feminization 7 years ago PornHub
Sissy multiple handsfree orgasms part 1
04:18 Sissy multiple handsfree orgasms part 1 Tags: Amateur, Cumshot, Toys, Cum, Orgasm, Sissy, Hands Free 7 years ago PornHub
crossdresser takes a big dick whenever its given
05:36 crossdresser takes a big dick whenever its given Tags: Dick, Big Cock, Sucking, Hard Fuck, Sissy 7 years ago PornHub
MySissySlutMaryCamSlut
01:10:50 MySissySlutMaryCamSlut Tags: Ass, Webcam, Sissy 7 years ago PornHub
Crossdresser having fun on cam
05:13 Crossdresser having fun on cam Tags: Amateur, Webcam, Sissy, Satin 7 years ago PornHub
Crossdresser Melli fucking machine!
07:00 Crossdresser Melli fucking machine! Tags: Amateur, Anal, Fucking, Amateur Anal Sex, Transsexual, Tranny, Anal Fuck 7 years ago PornHub
Shanda schoolgurl poppers sissy faggot
10:59 Shanda schoolgurl poppers sissy faggot Tags: Amateur, Anal, Dildo, Amateur Anal Sex, Chubby, Fat, Tranny 7 years ago PornHub
So You Want to be a Sissy Slut?
10:22 So You Want to be a Sissy Slut? Tags: Blowjob, Slut, Creampie, Femdom, Gangbang, Shemale, Whore 7 years ago PornHub
Sissy crossdresser riding BBC dildo
03:03 Sissy crossdresser riding BBC dildo Tags: Pussy, Ass, Teen (18/19), Dildo, White, Riding, BBC (Big Black Cock) 7 years ago PornHub
Amateur Crossdresser First Suck Gets Messy
05:57 Amateur Crossdresser First Suck Gets Messy Tags: Blowjob, Amateur, Amateur Blowjob, Stockings, Dildo, Deepthroat, Throat 7 years ago PornHub
Hot Crossdresser Fucking His Own Ass
09:19 Hot Crossdresser Fucking His Own Ass Tags: Amateur, Ass, Dick, Anal, Big Ass, Fucking, Butt 7 years ago PornHub
Sissy Kali Smoking And Showing How Much She Loves Cock
04:57 Sissy Kali Smoking And Showing How Much She Loves Cock Tags: Dick, Blonde, Slut, Smoking, Tranny, Bimbo, Sissy 7 years ago PornHub
Hot Crossdresser Loves Anal Masturbating
06:08 Hot Crossdresser Loves Anal Masturbating Tags: Amateur, Teen (18/19), Anal, Dildo, Amateur Anal Sex, Teen Anal Sex (18/19), Masturbating 7 years ago PornHub
Sissy Sub gets fucked by masculine top
00:49 Sissy Sub gets fucked by masculine top Tags: Pussy, Tranny, Sissy 7 years ago PornHub
CROSSDRESSER WORE GRAY DRESS AND CUM ON A PERIOD PAD
12:05 CROSSDRESSER WORE GRAY DRESS AND CUM ON A PERIOD PAD Tags: Cum, Dress, Sissy 7 years ago PornHub
Sissy's dream yumiko's story episode JK 1
04:55 Sissy's dream yumiko's story episode JK 1 Tags: Teen (18/19), Story, Sissy 7 years ago PornHub
Submissive Sissy Loves Black Cock
11:20 Submissive Sissy Loves Black Cock Tags: Blowjob, Amateur, Ass, Dick, Brunette, Anal, Black 6 years ago PornHub
Sissy Rachel serving her master pt.2
08:20 Sissy Rachel serving her master pt.2 Tags: Ass, Solo, Anal, Doggystyle, Toys, Orgasm, Dildo 7 years ago PornHub
SISSY IN BLUE SHIRT AND BLUE BRA WITH RED THONG
02:57 SISSY IN BLUE SHIRT AND BLUE BRA WITH RED THONG Tags: Amateur, Panties, Thong, Bra, Femdom, Humiliation, Sissy 7 years ago PornHub
Sissy crossdresser fucking a big black dildo.
03:03 Sissy crossdresser fucking a big black dildo. Tags: Amateur, Ass, Anal, Toys, Black, Fucking, Dildo 7 years ago PornHub
Sissy Kayla solo
01:08 Sissy Kayla solo Tags: Solo, Slut, Sissy 6 years ago PornHub
Sexy sissy Kayla solo
06:23 Sexy sissy Kayla solo Tags: Solo, Anal, Toys, Butt, Dildo, Sissy, Anal Dildo 6 years ago PornHub
The Sissification II - Plump Sissy Ass
01:39 The Sissification II - Plump Sissy Ass Tags: Ass, Dick, Cum, Butt, Panties, Booty, Humiliation 6 years ago PornHub
MARRIED SISSY BOY HOME ALONE - BRA AND PANTY FUN!!!
12:27 MARRIED SISSY BOY HOME ALONE - BRA AND PANTY FUN!!! Tags: Panties, Bra, Femdom, Home, Cuckold, Humiliation, Sissy 6 years ago PornHub
Sissy chastity night! How to put on a cage
04:09 Sissy chastity night! How to put on a cage Tags: Orgasm, BDSM, Sissy, Cage, Denial 6 years ago PornHub
Sissy Crossdresser Getting Fucked in Dirty Ass
01:24 Sissy Crossdresser Getting Fucked in Dirty Ass Tags: Hardcore, Ass, Dirty, Sissy 6 years ago PornHub
Sissy Jerk and Sound
04:39 Sissy Jerk and Sound Tags: Amateur, Ass, Solo, Fetish, Stockings, Shemale, Jerking 6 years ago YouPorn
Wife Prostate Milk Sissy Husband With Huge Dildo Then Shoot Cum Over him
04:46 Wife Prostate Milk Sissy Husband With Huge Dildo Then Shoot Cum Over him Tags: Ass, Anal, Toys, Cum, Fetish, Facial, Orgasm 7 years ago YouPorn
Crossdresser loves her dildo
00:49 Crossdresser loves her dildo Tags: Toys, Webcam, Dildo, Shemale, Socks, Bisexual, Sissy 7 years ago YouPorn
Femdom slut and her naughty t-girl and sissy sluts
06:15 Femdom slut and her naughty t-girl and sissy sluts Tags: Anal, HD, Fetish, Slut, Femdom, Naughty, Shemale 7 years ago YouPorn
Sissy Hot Sexy Leather.mpeg
11:30 Sissy Hot Sexy Leather.mpeg Tags: HD, Fetish, Shemale, Leather, Tranny, Sissy 7 years ago YouPorn
Sultry Goddess Paddles Sissy Maid
07:17 Sultry Goddess Paddles Sissy Maid Tags: Amateur, Ass, Fetish, BDSM, Wife, Bondage, Femdom 7 years ago YouPorn
Teen sissy plays with her long cock
10:36 Teen sissy plays with her long cock Tags: Amateur, Dick, Teen (18/19), Cumshot, HD, Big Cock, Cum 7 years ago YouPorn
Sissy teen with a monster cock
11:42 Sissy teen with a monster cock Tags: Amateur, Dick, Brunette, Teen (18/19), Solo, HD, Big Cock 7 years ago YouPorn
Pins Glove CBT Crossdresser
05:05 Pins Glove CBT Crossdresser Tags: Blonde, Fetish, Femdom, Mistress, Sissy, CBT (Cock Ball Torture), Whip 7 years ago Tube8
Sissy Crossdresser Fucks Dildo
02:00 Sissy Crossdresser Fucks Dildo Tags: Toys, Black, Interracial, Stockings, Lingerie, Dildo, Shemale 6 years ago xHamster
We will make you crossdress in public
05:00 We will make you crossdress in public Tags: HD, POV (Point Of View), Lingerie, Public, BDSM, Femdom, Sissy 7 years ago xHamster
Sissy crossdresser dildo fun
02:00 Sissy crossdresser dildo fun Tags: Amateur, Solo, Toys, HD, Stockings, Dildo, Shemale 7 years ago xHamster
Nessav Trying out my big toy - cd crossdress sissy
01:00 Nessav Trying out my big toy - cd crossdress sissy Tags: Amateur, Solo, Toys, Shemale, Sissy, Shemale In Solo 7 years ago xHamster
Sissy crossdresser dancing for her boyfriend
03:00 Sissy crossdresser dancing for her boyfriend Tags: Amateur, Lingerie, Boyfriend, Shemale, Dancing, Sissy 7 years ago xHamster
You are a pretty little crossdressing whore
06:00 You are a pretty little crossdressing whore Tags: HD, POV (Point Of View), Lingerie, BDSM, Femdom, Pretty, Whore 7 years ago xHamster
Crossdresser Sissy Faggot JaneDoeTV Anal Fun #4
05:00 Crossdresser Sissy Faggot JaneDoeTV Anal Fun #4 Tags: Amateur, Anal, Toys, Stockings, Amateur Anal Sex, Shemale, Sissy 7 years ago xHamster
You are such a little crossdressing slut
05:00 You are such a little crossdressing slut Tags: HD, POV (Point Of View), Lingerie, Slut, BDSM, Femdom, Sissy 7 years ago xHamster
We should make you crossdress in public
06:00 We should make you crossdress in public Tags: HD, POV (Point Of View), Lingerie, Public, BDSM, Femdom, Sissy 7 years ago xHamster
transvestite sissy lingerie nylon sounding urethral toy cock
11:00 transvestite sissy lingerie nylon sounding urethral toy cock Tags: Amateur, Dick, Toys, Lingerie, Nylon, Shemale, Sissy 7 years ago xHamster
Browse All 1388 Categories