Top New

Sissy Dress Up Videos

I need a new sissy girl to humiliate

I need a new sissy girl to humiliate

5 years ago

Mrs. Canuckpervs Dresses Mr. in Her Sexy Lingerie then puts Him On the Swing and pegs his ass!

Mrs. Canuckpervs Dresses Mr. in Her Sexy Lingerie then puts Him On the Swing and pegs his ass!

2 years ago

Hotwife Dresses Husband, puts him in Chastity with pink anal plug and ruined chastity Orgasm 🔐

Hotwife Dresses Husband, puts him in Chastity with pink anal plug and ruined chastity Orgasm 🔐

1 year ago

Crossdresser Wearing a Green Dress and a Pull-up Nappy, then Jerking off 01 男の娘洋服偽娘おむつ

Crossdresser Wearing a Green Dress and a Pull-up Nappy, then Jerking off 01 男の娘洋服偽娘おむつ

1 year ago

Love to Dress my Sissy up like the Slut he Is…Huge Strapon Pegging@ThetanplayfulBi

Love to Dress my Sissy up like the Slut he Is…Huge Strapon Pegging@ThetanplayfulBi

2 years ago

Sissy Wife POV Pegging Quickie with CEI

Sissy Wife POV Pegging Quickie with CEI

1 year ago

TGirl Lucy in Chastity - Toying her Sissy Ass with Big Dildos

TGirl Lucy in Chastity - Toying her Sissy Ass with Big Dildos

4 years ago

Crossdressing for Dessert: POV Dominant Girlfriend Dresses You up

Crossdressing for Dessert: POV Dominant Girlfriend Dresses You up

1 year ago

No Escape! Femboy Gets Tied up and Vibed!

No Escape! Femboy Gets Tied up and Vibed!

6 months ago

I Dress him up in my Lingerie and Fuck his Ass till he Cums all over himself

I Dress him up in my Lingerie and Fuck his Ass till he Cums all over himself

4 years ago

I Wanted to Show my new Dress to my Boyfriend and I Ended up Naked

I Wanted to Show my new Dress to my Boyfriend and I Ended up Naked

8 months 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

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

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

Horny Skinny Shemale Summer Dress Ride Huge Dildo Precum Intense Cumshot

Horny Skinny Shemale Summer Dress Ride Huge Dildo Precum Intense Cumshot

1 year ago

Be my Barbie Bimbo - Teaser Clip

Be my Barbie Bimbo - Teaser Clip

8 years ago

Brought Home to Be Seduced and Sissified

Brought Home to Be Seduced and Sissified

1 year ago

Loving Girlfriend Sissification / Dressup /JOI - Evie Rees

Loving Girlfriend Sissification / Dressup /JOI - Evie Rees

2 years ago

Demands he Wears her Lingerie to Masterbate together

Demands he Wears her Lingerie to Masterbate together

3 years ago

Hot Crossdresser having some Fun, Pink Asshole & Shaved Legs Naked in Bed

Hot Crossdresser having some Fun, Pink Asshole & Shaved Legs Naked in Bed

9 years ago

Trangender Fuck with a Big Dildo/abradabrer Dreams

Trangender Fuck with a Big Dildo/abradabrer Dreams

2 years ago

TEASER - let's Pick out your Panties for the Day shall we or will my Whip do It?

TEASER - let's Pick out your Panties for the Day shall we or will my Whip do It?

1 year ago

BodySwap W/ Female Roomate & Fucked by her BF Free Preview

BodySwap W/ Female Roomate & Fucked by her BF Free Preview

1 year ago

Sissified and Pegged

Sissified and Pegged

2 years ago

Close-up Sex Machine Fuck Cross Dressing Sissy Cute Outfit Anal Training #AnnyGirl

Close-up Sex Machine Fuck Cross Dressing Sissy Cute Outfit Anal Training #AnnyGirl

1 year ago

Episode 1 the Sexy Shemale Gets you off Sucking Cock ITS GODDESS LANA AS a SHEMALE

Episode 1 the Sexy Shemale Gets you off Sucking Cock ITS GODDESS LANA AS a SHEMALE

4 years ago

Husband gets sissified and his ass destroyed by mistresses strapon

Husband gets sissified and his ass destroyed by mistresses strapon

1 year ago

Kevin Fucked Into Kevina with Strap Ons!

Kevin Fucked Into Kevina with Strap Ons!

11 years ago

Sleepover Sissification (Preview)

Sleepover Sissification (Preview)

1 year ago

Sissifying you in Pink Lingerie and doing your Nails

Sissifying you in Pink Lingerie and doing your Nails

1 year ago

Kevin's Sissification By The Strap On Princess!

Kevin's Sissification By The Strap On Princess!

13 years ago

How to go from Male to Female in only a few Steps

How to go from Male to Female in only a few Steps

9 years ago

Crossdresser Captured and Dominated by three Mistresses

Crossdresser Captured and Dominated by three Mistresses

9 years ago

Smart Guy in Suit Wanks his Big Hard Cock in Frilly Nylon Panties

Smart Guy in Suit Wanks his Big Hard Cock in Frilly Nylon Panties

10 years ago

Be my Bimbo Slave- Part 1 by miss Faith Rae

Be my Bimbo Slave- Part 1 by miss Faith Rae

1 year ago

Be my Bimbo Slave- Part 2 by miss Faith Rae

Be my Bimbo Slave- Part 2 by miss Faith Rae

1 year ago

Heels Play and Vibrator Ruined Orgasm in Spandex - Mistress Julia

Heels Play and Vibrator Ruined Orgasm in Spandex - Mistress Julia

1 year ago

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