Top New

Sissy Dress Videos

Tall Tranny Jerking off and Cumming on Silk Dress

Tall Tranny Jerking off and Cumming on Silk Dress

6 years ago

Cross-dressing Masturbation in Micro Bikini

Cross-dressing Masturbation in Micro Bikini

2 years ago

Strap on Princess but Fucks Sissy Girl

Strap on Princess but Fucks Sissy Girl

10 years ago

Chinese Ladyboy in Pink Dress Opens Hotel Room Door and Cums on Stockings

Chinese Ladyboy in Pink Dress Opens Hotel Room Door and Cums on Stockings

1 year ago

Preview: Losing a Bet Ends with you in a Skirt: Bi-Encouragement, Femdom, made to Cross Dress

Preview: Losing a Bet Ends with you in a Skirt: Bi-Encouragement, Femdom, made to Cross Dress

2 years ago

Josie Blade Fucked Hard in a Red Dress and Falls over after

Josie Blade Fucked Hard in a Red Dress and Falls over after

3 years ago

Femboy Dressed in hello Kitty Cums from a Vibrator

Femboy Dressed in hello Kitty Cums from a Vibrator

5 years ago

A Video of Ejaculation by Dressing up as a Woman in a Public Toilet and doing Anal Masturbation.

A Video of Ejaculation by Dressing up as a Woman in a Public Toilet and doing Anal Masturbation.

3 years ago

Japanese Cross Dress Fist

Japanese Cross Dress Fist

4 years ago

Dress me for my Date Tonight / AUDIO ONLY CUCKOLD JOI

Dress me for my Date Tonight / AUDIO ONLY CUCKOLD JOI

7 years ago

Chinese Dress Cosplay Masturbation and Ejaculation

Chinese Dress Cosplay Masturbation and Ejaculation

1 year ago

Cute Skinny Shemale Summer Dress Huge Dildo Dirty Ride Intense Cum

Cute Skinny Shemale Summer Dress Huge Dildo Dirty Ride Intense Cum

2 years ago

Locked in Chastity under my Pretty Pink Dress 🥺

Locked in Chastity under my Pretty Pink Dress 🥺

1 year ago

Mature Transvestite /transexual taking of his Dress and Showing and Playing

Mature Transvestite /transexual taking of his Dress and Showing and Playing

5 years ago

Girlfriend Dresses you up for Halloween: Feminization, Chastity, Bi-Encouragement and Dirty Talking

Girlfriend Dresses you up for Halloween: Feminization, Chastity, Bi-Encouragement and Dirty Talking

1 year ago

Nylon Sissy Tucked into Bed in Straitjacket

Nylon Sissy Tucked into Bed in Straitjacket

4 years ago

HA44Wears Short Dress with Dildo Stuffed into Anal. Passers-by Pass by Takes out Secretly Fucks Anal

HA44Wears Short Dress with Dildo Stuffed into Anal. Passers-by Pass by Takes out Secretly Fucks Anal

1 year ago

Preview: Girls Night Feminization: Talked into Wearing Light Makeup, a Dress & Panties

Preview: Girls Night Feminization: Talked into Wearing Light Makeup, a Dress & Panties

2 years ago

Cute Skinny Shemale Pink Dress Fuck her Huge Pink Dildo and Cum twice in a Row

Cute Skinny Shemale Pink Dress Fuck her Huge Pink Dildo and Cum twice in a Row

2 years ago

Gorgeous Trans Girl in Dress Strips and Fucks her Tight Ass

Gorgeous Trans Girl in Dress Strips and Fucks her Tight Ass

2 years ago

Crossdresser Wearing a Maid Dress, a Bra, Diapers and Jerking off

Crossdresser Wearing a Maid Dress, a Bra, Diapers and Jerking off

3 years ago

Mistress does not let Sissy Cum | Edging

Mistress does not let Sissy Cum | Edging

6 months ago

My Cute 18 Year old Stepson Dressed as a Whore to Fuck with Men on the Street

My Cute 18 Year old Stepson Dressed as a Whore to Fuck with Men on the Street

1 year ago

Beautiful Shemale Dressing up High Heels to Show her Perfect Body and Dick and Anal Pussy for you

Beautiful Shemale Dressing up High Heels to Show her Perfect Body and Dick and Anal Pussy for you

4 years ago

Foot Fetish Slave Girl Dressed as Vampire Shackled and made to Cum by Pantyhose Dom

Foot Fetish Slave Girl Dressed as Vampire Shackled and made to Cum by Pantyhose Dom

4 years ago

Cross Dress for your Boss: Public Humiliation Dirty Talk & Crossdressing Encouragement

Cross Dress for your Boss: Public Humiliation Dirty Talk & Crossdressing Encouragement

2 years ago

Cross-dressing Masturbation in Black Leather Naughty Clothes

Cross-dressing Masturbation in Black Leather Naughty Clothes

3 years ago

BDSM Dressed Shemale in Zentai Full Bodysuit Nylon

BDSM Dressed Shemale in Zentai Full Bodysuit Nylon

3 years ago

It's a Video about Dressing up as a Woman and Just, you Know, Masturbating.

It's a Video about Dressing up as a Woman and Just, you Know, Masturbating.

4 years ago

OUT ON THE STREET take my Cuckold Dressed as a Whore in Heels

OUT ON THE STREET take my Cuckold Dressed as a Whore in Heels

3 years ago

Japanese Femboy Dressed as Teacher with Black Pantyhose

Japanese Femboy Dressed as Teacher with Black Pantyhose

2 years ago

HA55Super Short Dress Exposed Outdoors, Dildo Inserted into Anal on the Road!

HA55Super Short Dress Exposed Outdoors, Dildo Inserted into Anal on the Road!

11 months ago

Dressed up and Edging Til I Cream

Dressed up and Edging Til I Cream

4 years ago

Crossdresser in Dress Masturbates with Pink Plug

Crossdresser in Dress Masturbates with Pink Plug

7 years ago

Guys, tell me what I look like in this Dress, i'm a Slut.

Guys, tell me what I look like in this Dress, i'm a Slut.

1 year ago

Body Swap with Sexy PAWG, Dress up & Makeup FREE PREVIEW

Body Swap with Sexy PAWG, Dress up & Makeup FREE PREVIEW

1 year ago

Girlfriend Dresses you in her too Small Lingerie: GFE, Encouraged Crossdressing, Role Play

Girlfriend Dresses you in her too Small Lingerie: GFE, Encouraged Crossdressing, Role Play

1 year ago

F4M - Girlfriend x Crossdressing Listener - Dressing up for your Girlfriend - ASMR Roleplay Preview

F4M - Girlfriend x Crossdressing Listener - Dressing up for your Girlfriend - ASMR Roleplay Preview

2 years ago

White Girl Black Dress

White Girl Black Dress

9 months ago

Black Dressed Business Girl Relax after Busy Day in Office and Wank her Big Cock Cum Closeup Cumshot

Black Dressed Business Girl Relax after Busy Day in Office and Wank her Big Cock Cum Closeup Cumshot

2 years ago

Related to Sissy Dress

Sissy Discipline

Fem Humiliation

Sissy Dress Up Joi

Sissy

Cross Dressing Sissy

Femdom

Sissy Cross Dress

Bdsm

Sissy Sissy Training

Dress

Sissy Sissy Slave