Sissy

Sissy Sissy Training

Verified Amateurs

Sissy Sissy Slave

Sissy Sissy In Heat

Sissy Discipline

Sissy Sissy Slut

Top New

Sissies

Public Bathroom Buttplug Compilation

Public Bathroom Buttplug Compilation

5 years ago

I think you might be able to fit into my clothes

I think you might be able to fit into my clothes

7 years ago

We know you have been trying on our panties

We know you have been trying on our panties

8 years ago

2 years ago

Put on this hot little cocktail dress I got for you

Put on this hot little cocktail dress I got for you

7 years ago

You will look like a real woman when I am done

You will look like a real woman when I am done

8 years ago

My very Small Dick

My very Small Dick

2 years ago

Mistress Waxing Slaves Balls and Pubes

Mistress Waxing Slaves Balls and Pubes

4 years ago

You are nothing but a pathetic little bitch

You are nothing but a pathetic little bitch

8 years ago

Extremely Busy Highway Parking Lot

Extremely Busy Highway Parking Lot

5 years ago

Your cock is so small I can barely even see it SPH

Your cock is so small I can barely even see it SPH

8 years ago

You look pretty sexy in high heels and a dress

You look pretty sexy in high heels and a dress

8 years ago

I think you will look so pretty in this dress

I think you will look so pretty in this dress

7 years ago

Hot MILF Pegs Tiny Crossdresser until he Shakes and Cums on himself

Hot MILF Pegs Tiny Crossdresser until he Shakes and Cums on himself

1 year ago

SEXY CD SUCKS HER NEIGHBOR BEFORE GOING TO WORK

SEXY CD SUCKS HER NEIGHBOR BEFORE GOING TO WORK

4 years ago

I brought something I want you to wear

I brought something I want you to wear

7 years ago

Put on these panties and get on your knees

Put on these panties and get on your knees

8 years ago

You look pretty cute dressed as a girl

You look pretty cute dressed as a girl

8 years ago

I laid out a dress I want to you put on

I laid out a dress I want to you put on

9 years ago

You can be one of the girls around us

You can be one of the girls around us

8 years ago

You will be begging to be my bitch

You will be begging to be my bitch

7 years ago

We are going to make you look so pretty

We are going to make you look so pretty

8 years ago

They are going to treat me like a dirty whore

They are going to treat me like a dirty whore

2 years ago

I laid of a sexy little outfit for you to try on

I laid of a sexy little outfit for you to try on

8 years ago

We know you like trying on our clothes

We know you like trying on our clothes

8 years ago

Dressing you up like a girl is so much fun

Dressing you up like a girl is so much fun

8 years ago

Hanging 40lbs from Balls Properly! = more Pain!

Hanging 40lbs from Balls Properly! = more Pain!

4 years ago

We got you a cute princess costume to try on

We got you a cute princess costume to try on

9 years ago

You will look so sexy dressed in my clothes

You will look so sexy dressed in my clothes

8 years ago

Leg Shaking Anal Orgasms from Wrecking my Asshole with an Enormous Dildo

Leg Shaking Anal Orgasms from Wrecking my Asshole with an Enormous Dildo

1 year ago

You look kind of cute in your princess outfit

You look kind of cute in your princess outfit

8 years ago

You look so cute dressed as a princess

You look so cute dressed as a princess

8 years ago

Pantyhosed Lesbos and Golden Shower

Pantyhosed Lesbos and Golden Shower

9 months ago

You look really good in a dress and high heels

You look really good in a dress and high heels

7 years ago

The army of the CentoXCento

The army of the CentoXCento

5 months ago

Cumming over and over on Huge Anal Dildo despite Chastity Cage - Pornhub Gay

Cumming over and over on Huge Anal Dildo despite Chastity Cage - Pornhub Gay

1 year ago

Centoxcento Party Let's Try the Provinants in the Dark of the Private Room

Centoxcento Party Let's Try the Provinants in the Dark of the Private Room

5 months ago

I wonder if you can fit in these panties

I wonder if you can fit in these panties

8 years ago

A huge amateur orgy with nasty milf in private club

A huge amateur orgy with nasty milf in private club

5 months ago

We know you steal our clothes and try them on

We know you steal our clothes and try them on

8 years ago

Crossdresser Public Piss after Creampie

Crossdresser Public Piss after Creampie

5 years ago

Cumshot with Dick still Limp, after Hard Anal Dildo Play (double Anal, DAP)

Cumshot with Dick still Limp, after Hard Anal Dildo Play (double Anal, DAP)

4 years ago

Eelectro Stimulation and Big mr Hankey Dildo Anal Riding

Eelectro Stimulation and Big mr Hankey Dildo Anal Riding

4 years ago

Lets pretend you are one of the girls for the day

Lets pretend you are one of the girls for the day

6 years ago

Mistress Stepping on Balls

Mistress Stepping on Balls

6 years ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

3 months ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

4 months ago

Blowjob and Cumkiss for Sissy Husband

Blowjob and Cumkiss for Sissy Husband

7 months ago

Blowjob and Cumkiss for Sissy Husband

Blowjob and Cumkiss for Sissy Husband

1 year ago

POV Sissy in Chastity Suckng and Riding Dick. Sissy Erika Traviezisha Giving Blowjob POV.

POV Sissy in Chastity Suckng and Riding Dick. Sissy Erika Traviezisha Giving Blowjob POV.

4 years ago

Sissy Wanted My Stockings, So I Asked Him To Fuck His Ass… Pegging & Crossdressing

Sissy Wanted My Stockings, So I Asked Him To Fuck His Ass… Pegging & Crossdressing

1 year ago

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

1 year ago

Submissive Sissy Slave Tied and Fucked by Machine. Sissy Ass Drilled by Machine.

Submissive Sissy Slave Tied and Fucked by Machine. Sissy Ass Drilled by Machine.

4 years ago

Sissy Fucked both Ends, Cock in Mouth-pussy, Dildo Machine in Ass-pussy

Sissy Fucked both Ends, Cock in Mouth-pussy, Dildo Machine in Ass-pussy

5 years ago

Sissy Conditioning 1 Sissy Reboot

Sissy Conditioning 1 Sissy Reboot

4 years ago

Sissy in Heat Fucking her Ass with Dildo in the Streets at Night

Sissy in Heat Fucking her Ass with Dildo in the Streets at Night

5 years ago

Cum Slut Sissy Mind Set, Sissy Trainer, Sissy Mind, Sissy Brainwash, Sissy Mind Control Femboy

Cum Slut Sissy Mind Set, Sissy Trainer, Sissy Mind, Sissy Brainwash, Sissy Mind Control Femboy

2 years ago

Strapon & Piss Enema for Diapered Sissy Husband

Strapon & Piss Enema for Diapered Sissy Husband

1 year ago

Diaper Sissy Lesson: Chastity Peeing and Fisting

Diaper Sissy Lesson: Chastity Peeing and Fisting

1 year ago

Erika Sissy in Chastity Sucking and Riding Cock. (My Sissy Ass Gets Fucked)

Erika Sissy in Chastity Sucking and Riding Cock. (My Sissy Ass Gets Fucked)

5 years ago

Pissing and Pegging My Sissy Slave

Pissing and Pegging My Sissy Slave

1 year ago

Taking My Sissy-wife's Virginity - Pegging POV with Elle Eros

Taking My Sissy-wife's Virginity - Pegging POV with Elle Eros

10 months ago

Teaching my SISSY grilfriend how to FUCK a real pussy

Teaching my SISSY grilfriend how to FUCK a real pussy

2 years ago

Kinky Sissy Princess Veronica Taboo Masturbates in Chastity, Talking Frankly about her SISSIFICATION

Kinky Sissy Princess Veronica Taboo Masturbates in Chastity, Talking Frankly about her SISSIFICATION

1 year ago

Sissy in Chastity Public Walk Showing her Ass and then she is Fucked Bareback in many Positions

Sissy in Chastity Public Walk Showing her Ass and then she is Fucked Bareback in many Positions

2 years ago

Do you want to be a Sissy?

Do you want to be a Sissy?

3 years ago

Sissy Pet Training (Playing Fetch with Sissy Bitch)

Sissy Pet Training (Playing Fetch with Sissy Bitch)

4 years ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

4 months ago

PEGGING training and hot PROSTATE ORGASM for hot SISSY boyfriend

PEGGING training and hot PROSTATE ORGASM for hot SISSY boyfriend

5 months ago

Pervert nurse spits cum inside sissy's asshole

Pervert nurse spits cum inside sissy's asshole

1 year ago

Sissy Summer Camp with Elle Eros

Sissy Summer Camp with Elle Eros

7 months ago

ANAL for you, ANAL for me... SISSY boyfriend pegged and rewarded!

ANAL for you, ANAL for me... SISSY boyfriend pegged and rewarded!

4 months ago

Sissy Summer Camp with Elle Eros

Sissy Summer Camp with Elle Eros

7 months ago

Making him my Sissy Whore by DominaFire

Making him my Sissy Whore by DominaFire

2 years ago

Real SISSY ENEMA slave cums in his own mouth

Real SISSY ENEMA slave cums in his own mouth

5 months ago

Sissy Haylee's Public A2M with a Buttplug and a Dildo Part 1

Sissy Haylee's Public A2M with a Buttplug and a Dildo Part 1

4 years ago

Milk ENEMA bath for SISSY slave with full CONDOM inside his ass

Milk ENEMA bath for SISSY slave with full CONDOM inside his ass

5 months ago

Sissy in Chastity Fucks her Ass with Door Knob. she has many Dildo

Sissy in Chastity Fucks her Ass with Door Knob. she has many Dildo

4 years ago

POV: Sissy Crossdresser Fucked Bareback. Male Cock Slaps Sissy Clitty.

POV: Sissy Crossdresser Fucked Bareback. Male Cock Slaps Sissy Clitty.

3 years ago

Mistress sissifies her bitch boi and stretches his tight sissy hole with her cock

Mistress sissifies her bitch boi and stretches his tight sissy hole with her cock

1 year ago

Stupid Sissy in Chastity Training her Slutty Ass with a Fucking Machine

Stupid Sissy in Chastity Training her Slutty Ass with a Fucking Machine

5 years ago

Sissy Behavior Explained (Big Vibrating Butt Plug in Sissy Ass)

Sissy Behavior Explained (Big Vibrating Butt Plug in Sissy Ass)

5 years ago

I am Sissy Joyce Part 2

I am Sissy Joyce Part 2

4 years ago

Feminising my sissy boi husband and pegging his tight hole and filling his mouth with cum

Feminising my sissy boi husband and pegging his tight hole and filling his mouth with cum

1 year ago

Sissy Slut in Chastity and Sexy Lingerie Sucks Cock and Gets Fucked Raw Outdoors besides the Street

Sissy Slut in Chastity and Sexy Lingerie Sucks Cock and Gets Fucked Raw Outdoors besides the Street

3 years ago

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

10 months ago

Sissy Slut in Chastity Inserts a Pussy Fleshlight in her Ass for her Man to Penetrate Bareback

Sissy Slut in Chastity Inserts a Pussy Fleshlight in her Ass for her Man to Penetrate Bareback

4 years ago

Sissy Maid Femdom Pegging Compilation

Sissy Maid Femdom Pegging Compilation

9 months ago

Sissy Slut Training by DominaFire

Sissy Slut Training by DominaFire

2 years ago

Sissy husband dressed up as a worthless slut and fucked in his ass by his mistress

Sissy husband dressed up as a worthless slut and fucked in his ass by his mistress

1 year ago

SISSY ANAL HOOK TRAINING by DominaFire

SISSY ANAL HOOK TRAINING by DominaFire

2 years ago

Sissy is Fucked so Hard and her Head Starts Hitting the Wall, no one Cares.

Sissy is Fucked so Hard and her Head Starts Hitting the Wall, no one Cares.

5 years ago

Sissy clit bitch boi gets humiliated & his boi pussy pegged

Sissy clit bitch boi gets humiliated & his boi pussy pegged

11 months ago

Sissy Slut - try not to Cum Challenge

Sissy Slut - try not to Cum Challenge

3 years ago

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

3 months ago

Sissy in Micro Chastity Cage Shoving two Bananas up her Ass. Sissy in Body Stockings.

Sissy in Micro Chastity Cage Shoving two Bananas up her Ass. Sissy in Body Stockings.

4 years ago

Sissy Crossdress Instructions

Sissy Crossdress Instructions

5 years ago

Husband dressed up, bent over the sofa and pegged hard in his worthless sissy hole

Husband dressed up, bent over the sofa and pegged hard in his worthless sissy hole

1 year ago

Sissy Crossdresser in Chastity Walking in the Streets at Night with a Fox Tail Anal Plug inside her

Sissy Crossdresser in Chastity Walking in the Streets at Night with a Fox Tail Anal Plug inside her

3 years ago

Sissy in Flat Chastity Cage Riding a Transparent Horse Dildo

Sissy in Flat Chastity Cage Riding a Transparent Horse Dildo

1 year ago

Sissification Lecture

Sissification Lecture "SISSY COCK and ASSHOLE EVOLUTION" Veronica Taboo Shows DILDOS, PLUGS, CAGES

1 year ago

Sissy Anal Training

Sissy Anal Training

11 months ago

Latex Sissy Anal Training

Latex Sissy Anal Training

1 year ago

Pregnant-like Sissy no Hands Clitty in Chastity Leaking. Vibrator in Ass.

Pregnant-like Sissy no Hands Clitty in Chastity Leaking. Vibrator in Ass.

5 years ago

Sissy Anal Masturbation Emptying a Beer Bottle in her Asshole

Sissy Anal Masturbation Emptying a Beer Bottle in her Asshole

3 years ago

SISSY SLUT FUCKED HARD by DominaFire

SISSY SLUT FUCKED HARD by DominaFire

2 years ago

Sissy Crossdresser Walking outside with a Vibrator inside her Ass and a Micro Chastity Cage

Sissy Crossdresser Walking outside with a Vibrator inside her Ass and a Micro Chastity Cage

3 years ago

Sissy Feminization by Wife with Nair. Sissy Sucks a Dildo and is a Spitter

Sissy Feminization by Wife with Nair. Sissy Sucks a Dildo and is a Spitter

7 years ago

Husband Turned Sissy - Goddess Alexa

Husband Turned Sissy - Goddess Alexa

4 years ago

Sissy Transformation, Sissy Mindfuck, Sissification, Bimbo Brainwash, CEI, JOI, Femdom, Mistress

Sissy Transformation, Sissy Mindfuck, Sissification, Bimbo Brainwash, CEI, JOI, Femdom, Mistress

1 year ago

House Keeping Part 1 Spanked Caned Sissy Maid

House Keeping Part 1 Spanked Caned Sissy Maid

5 years ago

Husband gets completely transformed into a sissy cock hungry slut

Husband gets completely transformed into a sissy cock hungry slut

1 year ago

Feminized Sissy Slut with Pigtails and Makeup Sucks and Gets Strapon Pegged

Feminized Sissy Slut with Pigtails and Makeup Sucks and Gets Strapon Pegged

7 years ago

PEGGING CHASTITY SISSY WITH BAD DRAGON STRAPON

PEGGING CHASTITY SISSY WITH BAD DRAGON STRAPON

2 years ago

Sissy bitch dressed up, wearing a wig and pegged hardcore in his tight hole

Sissy bitch dressed up, wearing a wig and pegged hardcore in his tight hole

1 year ago

2020 Sissy Clit Contest Winner

2020 Sissy Clit Contest Winner

5 years ago

Alpha Male Tenderising my Sissy Ass Meats before he Starts Fucking me in Maid Costume

Alpha Male Tenderising my Sissy Ass Meats before he Starts Fucking me in Maid Costume

4 years ago

Tiny cock and balls pulled as my sissy husbands ass gets pegged

Tiny cock and balls pulled as my sissy husbands ass gets pegged

5 months ago

Male Fucking my Sissy Ass from Behind. I take his Dick Wearing my Sissy Lingerie and Chastity Cage.

Male Fucking my Sissy Ass from Behind. I take his Dick Wearing my Sissy Lingerie and Chastity Cage.

4 years ago

SISSY slut CUMS while PEGGING after GOLDEN SHOWER

SISSY slut CUMS while PEGGING after GOLDEN SHOWER

1 year ago