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Training Sissies

Pegged in Pink - Sissy Pegging POV

Pegged in Pink - Sissy Pegging POV

7 months ago

Femme Hubby's Sissy Surgery Free Preview

Femme Hubby's Sissy Surgery Free Preview

2 years ago

Madam Sadie Loves to Fuck Sissy Slaves Cute Arse with he Strapon

Madam Sadie Loves to Fuck Sissy Slaves Cute Arse with he Strapon

1 year ago

30 Days to Sissy Day 2: Shaving Free Preview

30 Days to Sissy Day 2: Shaving Free Preview

2 years ago

Sissy Slut Anal Masturbation with Clit Closed in Chastity_sc.20

Sissy Slut Anal Masturbation with Clit Closed in Chastity_sc.20

2 years ago

Vibrator on Sissy Cock Edging with Soft Cock

Vibrator on Sissy Cock Edging with Soft Cock

1 year ago

Tranny Swallows Sperm.mistress Teaches Sissy to Swallow Sperm

Tranny Swallows Sperm.mistress Teaches Sissy to Swallow Sperm

2 years ago

Sissy Girl Gets Ready for School while being Permanently Locked in Chastity Routine

Sissy Girl Gets Ready for School while being Permanently Locked in Chastity Routine

1 year ago

Hooters Gurl! Real Men don't do these things a Mesmerizing Short Short Sissy Story Erotic Audio

Hooters Gurl! Real Men don't do these things a Mesmerizing Short Short Sissy Story Erotic Audio

2 years ago

30 Days to Sissy Day 29: Fully Transform Free Preview

30 Days to Sissy Day 29: Fully Transform Free Preview

2 years ago

Sissy boi dressed up and pegged in his ass by his dominate mistress

Sissy boi dressed up and pegged in his ass by his dominate mistress

1 year ago

Strapon Slut Trained how to Suck (prerecorded Cam Session)

Strapon Slut Trained how to Suck (prerecorded Cam Session)

5 years ago

Mistress Training Kinky Sissy Bitch

Mistress Training Kinky Sissy Bitch

3 years ago

Sissy Training, Pegging her Ass !!

Sissy Training, Pegging her Ass !!

4 years ago

Big Strapon up your Ass Mistress Sissy Training

Big Strapon up your Ass Mistress Sissy Training

4 years ago

PISS OUTDOOR and Sissy Trainning Compilation

PISS OUTDOOR and Sissy Trainning Compilation

2 years ago

Wife Fucks Sissy Ashley while Folding Clothes, then Ashley Fucks Emily, Cum

Wife Fucks Sissy Ashley while Folding Clothes, then Ashley Fucks Emily, Cum

8 years ago

Verbal Domination Pegging Femdom Sissy Training Dominatrix Mistress Face Sitting POV Tattooed Model

Verbal Domination Pegging Femdom Sissy Training Dominatrix Mistress Face Sitting POV Tattooed Model

1 year ago

SISSY TRAINNING & CUMSHOTS COMPILATION

SISSY TRAINNING & CUMSHOTS COMPILATION

3 years ago

Sissy Trans Slut and Girl, Anal Training Outdoor

Sissy Trans Slut and Girl, Anal Training Outdoor

3 years ago

Sissy Charlotte Learns to Deepthroat Big Cock

Sissy Charlotte Learns to Deepthroat Big Cock

4 years ago

Pegging Sissy Training Submissive, Bubble Butt Sensual Strapon Domination.

Pegging Sissy Training Submissive, Bubble Butt Sensual Strapon Domination.

2 years ago

Femdom: Sissy Feminization Training! all you need to Know!

Femdom: Sissy Feminization Training! all you need to Know!

4 years ago

Total Sissification & Strapon Training from BadAssBitch

Total Sissification & Strapon Training from BadAssBitch

2 years ago

Deepthroat Training for my Bitch.

Deepthroat Training for my Bitch.

3 years ago

Sissy Slut Training to Worship Goddess Hairy Armpits before Pegging

Sissy Slut Training to Worship Goddess Hairy Armpits before Pegging

1 year ago

Married couple home pegging training

Married couple home pegging training

7 months ago

SOUNDING WITH ELECTRICAL TORTURE & BREATHPLAY FOR SISSY SLAVE

SOUNDING WITH ELECTRICAL TORTURE & BREATHPLAY FOR SISSY SLAVE

2 years ago

A Guy like you Sissy Humiliation Erotic Audio Story by Tara Smith Short Femdom Lecture Faggot Boi

A Guy like you Sissy Humiliation Erotic Audio Story by Tara Smith Short Femdom Lecture Faggot Boi

1 year ago

Milking the first Drops from my SISSY's PROSTATE

Milking the first Drops from my SISSY's PROSTATE

7 months ago

Slim Femboy Sissy Training her Smooth Ass with a Buttplug and Big Dildo

Slim Femboy Sissy Training her Smooth Ass with a Buttplug and Big Dildo

2 years ago

Sissy-slut Training this is how you become a REAL SLUT for Mistress

Sissy-slut Training this is how you become a REAL SLUT for Mistress

1 year ago

Training a Submissive Cock Sucker

Training a Submissive Cock Sucker

1 year ago

Trans Ria Bentley Trains StepDaughter Eden Espi for Anal Sex

Trans Ria Bentley Trains StepDaughter Eden Espi for Anal Sex

6 months ago

Krissy the Sissy’s Compilation

Krissy the Sissy’s Compilation

4 years ago

Bi Sexual Sissy Sluts and Mistress Tirza

Bi Sexual Sissy Sluts and Mistress Tirza

1 year ago

Sissygasm Challenge Day 5: Sissy Dildo Sucking Instructions

Sissygasm Challenge Day 5: Sissy Dildo Sucking Instructions

4 years ago

Sissy Tan White Girl Can’t Handle Big Dick Pushing 9 Inch Dildo up her Ass

Sissy Tan White Girl Can’t Handle Big Dick Pushing 9 Inch Dildo up her Ass

3 years ago

BBC Sissy Trainer and Mantra

BBC Sissy Trainer and Mantra "mercy Edition".

3 years ago

Amateur Girl with Beautiful Big Ass Pegging her Sissy Stepdad for the first Time

Amateur Girl with Beautiful Big Ass Pegging her Sissy Stepdad for the first Time

1 year ago

Sissy Girl Trainer Ride it Pro for Papi

Sissy Girl Trainer Ride it Pro for Papi

2 years ago

2 years ago

Making my Sissy Bitch Gag on 8 Inch BBC Strap on Nasty White Slut in Training

Making my Sissy Bitch Gag on 8 Inch BBC Strap on Nasty White Slut in Training

3 years ago

Degraded Sissy Fuck Doll - Mouth Pussy Training

Degraded Sissy Fuck Doll - Mouth Pussy Training

3 years ago

Goddess Anastasia's Husband Slut Training Promo

Goddess Anastasia's Husband Slut Training Promo

2 years ago

Tgirl Takes two Dildo's in Anal Training Vid

Tgirl Takes two Dildo's in Anal Training Vid

1 year ago

Training her for Breeding

Training her for Breeding

1 year ago

I Train Anal Whore (Prerecorded Live Show with my Virtual )

I Train Anal Whore (Prerecorded Live Show with my Virtual )

3 years ago

Training him to be a Whore (Rough Pegging)

Training him to be a Whore (Rough Pegging)

1 year ago

Slut Training my Sissy Sluts Ass + Whipping

Slut Training my Sissy Sluts Ass + Whipping

2 years ago

Ass Training my Sissy Babe she cant Handle the Dick so I had to be Rough & Hard

Ass Training my Sissy Babe she cant Handle the Dick so I had to be Rough & Hard

3 years ago

Asshole Stretching Compilation Sissy Slut Queefing from Huge Toys - Vince_wt

Asshole Stretching Compilation Sissy Slut Queefing from Huge Toys - Vince_wt

2 years ago

Trans Emma Training to Cum like a Good Girl

Trans Emma Training to Cum like a Good Girl

2 years ago

Femdom Mistress Training her BDSM Slave

Femdom Mistress Training her BDSM Slave

1 year ago

THIS IS HOW MISTRESS TRAINING OBEDIENT SLAVE PUPPY DOG AND CHASTITY LITTLE TINY COCK

THIS IS HOW MISTRESS TRAINING OBEDIENT SLAVE PUPPY DOG AND CHASTITY LITTLE TINY COCK

1 year ago

BBC Sissy Slut Lola Bouncing on a 10in Monster Black Dick

BBC Sissy Slut Lola Bouncing on a 10in Monster Black Dick

2 years ago

Sissy Joyce needs to get Milked

Sissy Joyce needs to get Milked

3 years ago

Sunday Humiliation for Sissy husband Full

Sunday Humiliation for Sissy husband Full

3 months ago

Sissy Motivation 3: Teared Asshole (sissy Trainer, Sissy Instruction, Sissification, Femboy)

Sissy Motivation 3: Teared Asshole (sissy Trainer, Sissy Instruction, Sissification, Femboy)

3 years ago

Dominatrix Mara Transforms her Sissy into a Pink Barbie [feminization Kink / BDSM POV]

Dominatrix Mara Transforms her Sissy into a Pink Barbie [feminization Kink / BDSM POV]

3 years ago

First Time a Sissy Dressing up and make up

First Time a Sissy Dressing up and make up

3 years ago

Sissy Tormented and Verbally Humiliated by Mistress with Inflatable Butt Plug

Sissy Tormented and Verbally Humiliated by Mistress with Inflatable Butt Plug

4 years ago

Sissy Crossdresser Gets HUGE Facial from Grindr Daddy

Sissy Crossdresser Gets HUGE Facial from Grindr Daddy

2 years ago

Sissy Gaping while Parents are Watching TV

Sissy Gaping while Parents are Watching TV

4 years ago

Cuckold Experiment Turned you into a Sissy Whore

Cuckold Experiment Turned you into a Sissy Whore

3 years ago

Sissy Sex Erotic Audio by Tara Smith. Sissy Bi Encouragement & Dirty Talk

Sissy Sex Erotic Audio by Tara Smith. Sissy Bi Encouragement & Dirty Talk

5 years ago

Ultimate Sissy Rubber Doll Workout

Ultimate Sissy Rubber Doll Workout

6 years ago

I do everything which me say my Owner, Including Blowjobs on Public Place. I am Obedient Sissy Slut

I do everything which me say my Owner, Including Blowjobs on Public Place. I am Obedient Sissy Slut

9 months ago

Sissy Crossdresser BLOWJOB FACIAL & Cum Play

Sissy Crossdresser BLOWJOB FACIAL & Cum Play

3 years ago

Sissy getting Ready to go out for a Public Walk by Inserting two Dancing Vibrators up her Ass

Sissy getting Ready to go out for a Public Walk by Inserting two Dancing Vibrators up her Ass

1 year ago

Real PHONE SEX with Tara Smith - Momma's BBC Sissy wants to be a Girl SPH

Real PHONE SEX with Tara Smith - Momma's BBC Sissy wants to be a Girl SPH

5 years ago

Lola Crystals Playing with Sexy Sissy Tightass and Sharing BBC

Lola Crystals Playing with Sexy Sissy Tightass and Sharing BBC

1 year ago

SISSY BITCH BRAINWASHING. FUCK CONSTANTLY BIG COCKS. ANAL DESTRUCTION. Sissy Fucked in Chastity

SISSY BITCH BRAINWASHING. FUCK CONSTANTLY BIG COCKS. ANAL DESTRUCTION. Sissy Fucked in Chastity

2 years ago

Sissy Crossdresser Throated by a Tinder Daddy

Sissy Crossdresser Throated by a Tinder Daddy

2 years ago

Sissification Lecture

Sissification Lecture "the MEANING of SISSY LIFE" by Mistress Veronica Taboo at Online Sissy Academy

2 years ago

Sissygasm from Anal Masturbation in Sissy Slut with Closed Clit in Chastity_sc.28

Sissygasm from Anal Masturbation in Sissy Slut with Closed Clit in Chastity_sc.28

2 years ago

Sissy Slut Adventures Volume 1

Sissy Slut Adventures Volume 1

5 months ago

Cute Sissy Girl, Lost her Butt Plug in her Ass😳🍑

Cute Sissy Girl, Lost her Butt Plug in her Ass😳🍑

3 years ago

"like a GIRL!" SISSY EDM - Feminization FEMDOM Reprogramming MindFUCK

9 months ago

Cuckold is a sissy whore cock slave Mind Fuck

Cuckold is a sissy whore cock slave Mind Fuck

2 years ago

Sissy Slut Anal Masturbation with Clit Closed in Chastity_sc.17

Sissy Slut Anal Masturbation with Clit Closed in Chastity_sc.17

2 years ago

Pegged in Pink - Sissy Pegging POV

Pegged in Pink - Sissy Pegging POV

1 year ago

Sissy follows Mistress Gie's Order to Show Viewers Close up Anal Workout

Sissy follows Mistress Gie's Order to Show Viewers Close up Anal Workout

2 years ago

Hot Kissing with a Crossdressing Sissy

Hot Kissing with a Crossdressing Sissy

2 years ago

Sissy Slut Nurse Lola Treating a Big Black Cock Erection

Sissy Slut Nurse Lola Treating a Big Black Cock Erection

2 years ago

Sissy Slut Kitty Feeding on Big Black Juicy Meat Stick

Sissy Slut Kitty Feeding on Big Black Juicy Meat Stick

2 years ago

My SISSY's PISS & PEGGING Submission

My SISSY's PISS & PEGGING Submission

9 months ago

Sissy Anal Exam. 5 Fingers

Sissy Anal Exam. 5 Fingers

2 years ago

Exhibit Sissy Caught with Dancing Dildo Outdoors tries to Seduce the Voyeur

Exhibit Sissy Caught with Dancing Dildo Outdoors tries to Seduce the Voyeur

1 year ago

Sissy Lola Crystals Gets BBC Rock Hard for round 2

Sissy Lola Crystals Gets BBC Rock Hard for round 2

1 year ago

Sissy Motivation 4: Sex Machine (sissy Trainer, Sissy Instruction, Sissification, Femboy)

Sissy Motivation 4: Sex Machine (sissy Trainer, Sissy Instruction, Sissification, Femboy)

11 months ago

Sissy Leak and Cum for Pantyhose Free Preview

Sissy Leak and Cum for Pantyhose Free Preview

3 years ago

Sissy Cums in Flat Chastity Cage after being Fucked by her Machine

Sissy Cums in Flat Chastity Cage after being Fucked by her Machine

1 year ago

Sissy Slut Jerks off while Fantasizing - Dirty Talk

Sissy Slut Jerks off while Fantasizing - Dirty Talk

1 year ago

Maybe somebody wants to Play with my Sissy Ass, Gentlemens?:)

Maybe somebody wants to Play with my Sissy Ass, Gentlemens?:)

3 years ago

Sissy Fits Magic Vibrating Wand in her Asshole and then Gets 900ml Beer Enema

Sissy Fits Magic Vibrating Wand in her Asshole and then Gets 900ml Beer Enema

2 years ago

30 Days to Sissy Day 6: Sit to Pee Free Preview

30 Days to Sissy Day 6: Sit to Pee Free Preview

2 years ago

Horny Sissy in Chastity and Pink Lingerie Pours 900ml of Beer inside her Asshole with the Open Door!

Horny Sissy in Chastity and Pink Lingerie Pours 900ml of Beer inside her Asshole with the Open Door!

2 years ago

Tranny TS Sissy Ladyboy Transgender Cum Slut Deepthroat Cock Sucking Big Giant Huge Cockb Dick Penis

Tranny TS Sissy Ladyboy Transgender Cum Slut Deepthroat Cock Sucking Big Giant Huge Cockb Dick Penis

4 years ago

Femdom Mistress Goddess V Humiliates & Fully Feminizes Chastity Cuckold Sissy sub Slave W/ SPH 1/3

Femdom Mistress Goddess V Humiliates & Fully Feminizes Chastity Cuckold Sissy sub Slave W/ SPH 1/3

1 year ago

Sissy Sluts take Hormones and Fuck

Sissy Sluts take Hormones and Fuck

2 years ago

2 years ago

Sissy Schoolgirl Gets Destroyed and Creampied by BBC

Sissy Schoolgirl Gets Destroyed and Creampied by BBC

1 year ago

Sissy Trainer - you are Sissy

Sissy Trainer - you are Sissy

2 years ago

Turning my Boyfriend into a Sissy Slut

Turning my Boyfriend into a Sissy Slut

2 years ago

Sissy Cums with Inverted Chastity Cage on

Sissy Cums with Inverted Chastity Cage on

1 year ago

【hands Free Orgasm】Japanese Sissy 『nipple Masturbation』Hands Free♡【ladyboy 女装偽娘 Crossdresser】

【hands Free Orgasm】Japanese Sissy 『nipple Masturbation』Hands Free♡【ladyboy 女装偽娘 Crossdresser】

1 year ago

Feminization: your new Life as Sissy - Ep4 Turning this Wanker into a Slave - Mistress Julia

Feminization: your new Life as Sissy - Ep4 Turning this Wanker into a Slave - Mistress Julia

1 year ago

Femdom Sissy POV

Femdom Sissy POV

1 year ago

Pretty Sissy Crossdresser CUMS from Giving a BLOWJOB

Pretty Sissy Crossdresser CUMS from Giving a BLOWJOB

3 years ago

Do you Wanna be a Sissy? first Time in your Life? Ok, that's Video for You! FemDom POV Sissification

Do you Wanna be a Sissy? first Time in your Life? Ok, that's Video for You! FemDom POV Sissification

3 years ago

Hot Girl Turns you into a Sissy Cheerleader SLUT!

Hot Girl Turns you into a Sissy Cheerleader SLUT!

1 year ago

Sissy Slut Mind Fuck 4- Tinder Date Night

Sissy Slut Mind Fuck 4- Tinder Date Night

3 years ago

My Sissy Slut Bisexual Crossdressing Exposure Fantasy Erotic Audio Bi Encouragement Humiliation

My Sissy Slut Bisexual Crossdressing Exposure Fantasy Erotic Audio Bi Encouragement Humiliation

3 years ago

Mistress makes Sissy from Girlz Pro Suck Dildo and then Fucks her Doggy Style

Mistress makes Sissy from Girlz Pro Suck Dildo and then Fucks her Doggy Style

1 year ago

Lets Play Repeat after me Sissy Boi COCK WORSHIP VERSION

Lets Play Repeat after me Sissy Boi COCK WORSHIP VERSION

4 years ago

BDSM, Sissy Chastity

BDSM, Sissy Chastity

3 years ago

BBC Addict Brainwash Femdom SISSY

BBC Addict Brainwash Femdom SISSY

4 years ago

Sissy Cums HARD in Chastity

Sissy Cums HARD in Chastity

2 years ago

Undercover Crossdresser Bisexual Sissy Humiliation Exposure Encouragement Mesmerizing Erotic Audio

Undercover Crossdresser Bisexual Sissy Humiliation Exposure Encouragement Mesmerizing Erotic Audio

3 years ago