Ai Sissy (360)

The best and newest ai sissy videos

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

Lesbian8 8 months ago

sucking cock, thin white sissy, femboi, feminine, video created by AI

sucking cock, thin white sissy, femboi, feminine, video created by AI

Seduced 8 months ago

Chastity Release: Your last penetration of your Life ? Maitresse Julia

HD 0:10 / 16:51

Chastity Release: Your last penetration of your Life ? Maitresse Julia

LoyalFans 1 year ago

I'll fuckin' help you become the sissy mega-slut you were meant to be, you fuckin' pixie! I'll guide you thru your fuckin' transformation and make you my lil' sissy bi-atch, you fuckin' faggot! (FEMINIZATION ROLEPLAY - AI GENER

I'll fuckin' help you become the sissy mega-slut you were meant to be, you fuckin' pixie! I'll guide you thru your fuckin' transformation and make you my lil' sissy bi-atch, you fuckin' faggot! (FEMINIZATION ROLEPLAY - AI GENER

HentaiGem 6 months ago

Diapers and a Babysitter for the Bed Wetter

54% HD 0:30 / 17:41

Diapers and a Babysitter for the Bed Wetter

Clips4sale 7 months ago

Up Down Stop Squeeze&mdash_Tessa Breaks Your Gooner Brain

Premium HD 19:20

Up Down Stop Squeeze&mdash_Tessa Breaks Your Gooner Brain

xnxxGold 4 months ago

Reveal your true colors! Take our sissy detector test and face the consequences! - FEMINIZATION ROLEPLAY (AI)

Reveal your true colors! Take our sissy detector test and face the consequences! - FEMINIZATION ROLEPLAY (AI)

XVideos 8 months ago

Quiet Pegs You

67% 0:39 / 3:07

FapHouse 3 months ago

Black girl is your mistress and wants to play with your sweet ass - ROLEPLAY AI

Black girl is your mistress and wants to play with your sweet ass - ROLEPLAY AI

xHamster 8 months ago

The promotion... Kinda ? - A Sissy Caption Story

The promotion... Kinda ? - A Sissy Caption Story

Eporner 1 month ago

jet black hair, bobbed haircut with bangs, video created by AI

jet black hair, bobbed haircut with bangs, video created by AI

Seduced 6 months ago

femboi, short blonde hair, pink latex sissy, video created by AI

femboi, short blonde hair, pink latex sissy, video created by AI

Seduced 6 months ago

In bed with... - A TG sissy caption story

In bed with... - A TG sissy caption story

Eporner 1 month ago

Barely legal sissy trap standing inside, video created by AI

Barely legal sissy trap standing inside, video created by AI

Seduced 5 months ago

Fantasy (Pt. 2): My Wife's First Step to Interracial Domination

Fantasy (Pt. 2): My Wife's First Step to Interracial Domination

xHamster 4 months ago

Femdom Fantasy - AI Animated Slideshow for Adults

Femdom Fantasy - AI Animated Slideshow for Adults

xHamster 6 months ago

Expose your true colors! Take our sissy detector test and face the consequences! - FEMINIZATION ROLEPLAY (AI)

Expose your true colors! Take our sissy detector test and face the consequences! - FEMINIZATION ROLEPLAY (AI)

HentaiGem 5 months ago

cowgirl, Very small sissy femboy and very, video created by AI

cowgirl, Very small sissy femboy and very, video created by AI

Seduced 4 months ago

Goon AI PMV

Eporner 5 months ago

ANIME wife blow big dick music video

ANIME wife blow big dick music video

xHamster 1 month ago

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION

PornoXO 1 year ago

short blonde hair Caucasian bottom boi, video created by AI

short blonde hair Caucasian bottom boi, video created by AI

Seduced 1 year ago

Succubus transforms you in a perfect sissy slut and make you beg to be fucked like a dirty whore [FEMINIZATION ROLEPLAY] [AI GENERATED]

Succubus transforms you in a perfect sissy slut and make you beg to be fucked like a dirty whore [FEMINIZATION ROLEPLAY] [AI GENERATED]

XVideos 1 year ago

sucking cock, slender white sissy, femboi, feminine, video created by AI

sucking cock, slender white sissy, femboi, feminine, video created by AI

Seduced 8 months ago

From Your Hands to Your Mouth The Ultimate BBC JOI

Premium HD 13:59

From Your Hands to Your Mouth The Ultimate BBC JOI

xnxxGold 4 months ago

Fantasy (Pt. 4): My Wife's First Step to Interracial Domination

Fantasy (Pt. 4): My Wife's First Step to Interracial Domination

xHamster 4 months ago

Te Transform in Tarfa Mea

60% HD 1:01 / 10:02

Te Transform in Tarfa Mea

FapHouse 10 months ago

My Husband Sissified: A Female Latex Slave Doll Pegged - Mistress Julia feat. Sukeban

58% 4K 0:10 / 20:46

My Husband Sissified: A Female Latex Slave Doll Pegged - Mistress Julia feat. Sukeban

LoyalFans 5 months ago

Mistresse craves to suit u up like her fucktoy and assist u educate with a belt-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistresse craves to suit u up like her fucktoy and assist u educate with a belt-on (FEMINIZATION ROLEPLAY - AI GENERATED)

SortPorn 10 months ago

Sub commands to listen to and comply your dominatrix (marionette instructing)

Sub commands to listen to and comply your dominatrix (marionette instructing)

HentaiGem 9 months ago

Te Transform in Tarfa Mea

63% HD 0:39 / 10:02

Te Transform in Tarfa Mea

FapHouse 10 months ago

Mistress wants to dress you up like her personal fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistress wants to dress you up like her personal fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

XVideos 10 months ago

Expressed - Weenie Addiction Test - 720p

Expressed - Weenie Addiction Test - 720p

HentaiGem 2 months ago

Admets que tu es une femelle !

HD 0:10 / 24:13

Admets que tu es une femelle !

LoyalFans 1 week ago

Your New Life as My Free Use Sissy

HD 0:39 / 16:13

Your New Life as My Free Use Sissy

FapHouse 1 week ago

Be a Sissy for AI

51% HD 0:10 / 4:10

Be a Sissy for AI

LoyalFans 1 year ago

cei play this after your gooning session loop times three

cei play this after your gooning session loop times three

PornBox 3 years ago

Sexy Femdom Cartoon - Kinky Domination Story

Sexy Femdom Cartoon - Kinky Domination Story

xHamster 4 months ago

Spectacular moment from "Slave instructions to listen to and serve your mistress (slave training)"

Spectacular moment from "Slave instructions to listen to and serve your mistress (slave training)"

xHamster 10 months ago

Your New Life as My Free Use Sissy

Your New Life as My Free Use Sissy

FapHouse 1 week ago

Domina instructs you that deep throating rod isn't batty boy if you're using undies - FEMINIZATION ROLEPLAY (AI)

Domina instructs you that deep throating rod isn't batty boy if you're using undies - FEMINIZATION ROLEPLAY (AI)

HentaiGem 6 months ago

Pussygirl Wants Love and Sex. Hentai Anime Cartoon. Ai Animation

Pussygirl Wants Love and Sex. Hentai Anime Cartoon. Ai Animation

FapHouse 4 weeks ago

Your Last Ejaculation Ever! After? You Become My Latex Object Wife - Mistress Julia feat. Sukeban

59% 4K 0:10 / 17:52

Your Last Ejaculation Ever! After? You Become My Latex Object Wife - Mistress Julia feat. Sukeban

LoyalFans 5 months ago

J'encule une grosse p*te -
I'm fucking a fat whore (pegging)

HD 0:10 / 12:48

J'encule une grosse p*te - I'm fucking a fat whore (pegging)

LoyalFans 1 week ago

ONLY BLONDES GONE WILD - EXTENDED

64% HD 0:10 / 9:39

ONLY BLONDES GONE WILD - EXTENDED

LoyalFans 1 year ago

sucking cock, swhite sissy, femboi, feminine legs, video created by AI

sucking cock, swhite sissy, femboi, feminine legs, video created by AI

Seduced 8 months ago

Key moment from "Slave instructions to listen to and serve your mistress (slave training)"

Key moment from "Slave instructions to listen to and serve your mistress (slave training)"

xHamster 10 months ago

A hyperfeminine sissy bride having, video created by AI

A hyperfeminine sissy bride having, video created by AI

Seduced 8 months ago

Roommate transformed you in a sissy and fucked your virgin ass with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Roommate transformed you in a sissy and fucked your virgin ass with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

XVideos 1 year ago

U failed the exam, teacher craves to castigate u by feminizing and screwing your sissy aperture(FEMINIZATION ROLEPLAY - AI GENERATED)

U failed the exam, teacher craves to castigate u by feminizing and screwing your sissy aperture(FEMINIZATION ROLEPLAY - AI GENERATED)

SortPorn 10 months ago

Best of Squirting - Vol.1

Premium VR 21:58

Best of Squirting - Vol.1

SexLikeReal 1 year ago

sucking cock, a sissy transwoman leaning over and, video created by AI

sucking cock, a sissy transwoman leaning over and, video created by AI

Seduced 1 week ago

That night your step-sister got you to eat your cummies SO HOTT

Premium HD 18:25

That night your step-sister got you to eat your cummies SO HOTT

xnxxGold 4 months ago

sucking cock, green goblin sissy piggy, shortstack, video created by AI

sucking cock, green goblin sissy piggy, shortstack, video created by AI

Seduced 7 months ago

Little Sissy

Premium VR 15:04

SexLikeReal 2 months ago

Epic moment from "Cruel Reell and Steeltoyz Present: The 15-Piece Cock Cage Set - powered by AI"

Epic moment from "Cruel Reell and Steeltoyz Present: The 15-Piece Cock Cage Set - powered by AI"

xHamster 5 months ago

Your New Life as My Free Use Sissy

HD 1:01 / 16:13

Your New Life as My Free Use Sissy

FapHouse 2 weeks ago

14 ANTICHRISTmass Eve: Eternal Cuck-Faggot Damnation

14 ANTICHRISTmass Eve: Eternal Cuck-Faggot Damnation

Clips4sale 2 months ago

sucking cock, slender white sissy, femboi, feminine, video created by AI

sucking cock, slender white sissy, femboi, feminine, video created by AI

Seduced 8 months ago

Fantasy (Pt. 5 Final): My Wife's First Step to Interracial Domination

Fantasy (Pt. 5 Final): My Wife's First Step to Interracial Domination

xHamster 4 months ago

Cuckqueaning Wifey Feat Astrodomina

Premium VR 11:01

Cuckqueaning Wifey Feat Astrodomina

SexLikeReal 3 months ago

1sissy, age 20, 1succubus with strap on, video created by AI

1sissy, age 20, 1succubus with strap on, video created by AI

Seduced 6 months ago

ANIME wife blow big dick music video Clip 1

ANIME wife blow big dick music video Clip 1

xHamster 1 month ago

Sissy asian-mexican woman, blonde hair, 22, video created by AI

Sissy asian-mexican woman, blonde hair, 22, video created by AI

Seduced 11 months ago

short buzzcut manly blonde hair 1femboy, in, video created by AI

short buzzcut manly blonde hair 1femboy, in, video created by AI

Seduced 10 months ago

Gooner Paradise #1 – (Trailer) – AI Generated

Gooner Paradise #1 – (Trailer) – AI Generated

Amateur8 7 months ago

Mistress turns you into bunny slut, let&#039_s you to suck first client&#039_s dick. Swallow cum, sissy! (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistress turns you into bunny slut, let&#039_s you to suck first client&#039_s dick. Swallow cum, sissy! (FEMINIZATION ROLEPLAY - AI GENERATED)

XVideos 10 months ago

Japanese mistress set your sissy goals to embrace feminization - JOI ROLEPLAY AI

Japanese mistress set your sissy goals to embrace feminization - JOI ROLEPLAY AI

XVideos 8 months ago

You will never be to ld to Enjoy the Cummies from a BIG FAT JUICY BLACK COCK

Premium HD 8:05

You will never be to ld to Enjoy the Cummies from a BIG FAT JUICY BLACK COCK

XVideosRed 3 years ago

Slave instructions to listen to and serve your mistress (slave training)

Slave instructions to listen to and serve your mistress (slave training)

xHamster 10 months ago

Mistress Saida - Sissy Transformation Begins

Premium VR 10:40

Mistress Saida - Sissy Transformation Begins

SexLikeReal 10 months ago

Pussygirl Wants Love and Sex. Hentai Anime Cartoon. Ai Animation

Pussygirl Wants Love and Sex. Hentai Anime Cartoon. Ai Animation

xHamster 1 month ago

Sissification Affirmations

HD 0:39 / 21:08

Sissification Affirmations

FapHouse 1 year ago

Sissy Slut Caught and Humiliated

Premium VR 34:09

Sissy Slut Caught and Humiliated

SexLikeReal 11 months ago

Cuckoldry Fantasy (Pt. 1): My Wife's First Step to Interracial Domination

Cuckoldry Fantasy (Pt. 1): My Wife's First Step to Interracial Domination

xHamster 4 months ago

you will never be to ld to enjoy the cummies from a big fat juicy black cock

you will never be to ld to enjoy the cummies from a big fat juicy black cock

PornBox 3 years ago

broken and used_ the ultimate sissy humiliation countdown

HD 0:30 / 15:30

broken and used_ the ultimate sissy humiliation countdown

PornBox 4 months ago

Indian stepsis fucking pussy

Indian stepsis fucking pussy

xHamster 10 months ago

Creampies Collection (Vol. 1)

Premium VR 45:14

Creampies Collection (Vol. 1)

SexLikeReal 1 year ago

Sissy bride, Wearing a massive towering, video created by AI

Sissy bride, Wearing a massive towering, video created by AI

Seduced 4 months ago

You will never be to ld to Enjoy the Cummies from a BIG FAT JUICY BLACK COCK

Premium HD 8:05

You will never be to ld to Enjoy the Cummies from a BIG FAT JUICY BLACK COCK

xnxxGold 3 years ago

Sissification Affirmations

HD 0:10 / 21:03

Sissification Affirmations

LoyalFans 1 year ago

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

PornFreeNow 8 months ago

Quiet Pegs You

xHamster 3 months ago

Astarielle's Sissy Heresy JOI Ritual

Astarielle's Sissy Heresy JOI Ritual

Clips4sale 2 months ago

Your Wife Turned You Into a Diapered SISSY

55% 4K 0:46 / 14:44

Your Wife Turned You Into a Diapered SISSY

Clips4sale 1 year ago

Nobody Fucks With Puma

Premium VR 19:09

Nobody Fucks With Puma

SexLikeReal 1 month ago

Step-Sister Humiliates You in DIAPERS

46% 0:33 / 13:24

Step-Sister Humiliates You in DIAPERS

Clips4sale 1 year ago

Gooner Paradise #1 – (Trailer) – AI Generated

Gooner Paradise #1 – (Trailer) – AI Generated

SortPorn 7 months ago

My Curse Turns Cocks into Clits

63% 0:36 / 11:09

My Curse Turns Cocks into Clits

Clips4sale 4 months ago

Gooner Paradise #1 – (Trailer) – AI Generated

Gooner Paradise #1 – (Trailer) – AI Generated

MatureTubeHere 7 months ago

Indian stepsis fucking pussy

Indian stepsis fucking pussy

Fapcat 9 months ago

Gooner Paradise #1 &ndash_ (Trailer) &ndash_ AI Generated

Gooner Paradise #1 &ndash_ (Trailer) &ndash_ AI Generated

XVideos 7 months ago

Quiet Pegs You

xHamster 3 months ago

Mereoleona Moaning Hot and Getting Naughty - Hentaijoi Guided Handjob

Mereoleona Moaning Hot and Getting Naughty - Hentaijoi Guided Handjob

FapHouse 4 months ago

Sissies only watches censored porn - AI JOI

Sissies only watches censored porn - AI JOI

XVideos 8 months ago

You failed the exam, now the teacher wants to punish you by feminizing you and fucking your sissy hole (FEMINIZATION ROLEPLAY - AI GENERATED)

You failed the exam, now the teacher wants to punish you by feminizing you and fucking your sissy hole (FEMINIZATION ROLEPLAY - AI GENERATED)

XVideos 10 months ago

Sissy&#039_s tasks to complete and earn good girl points - FEMINIZATION ROLEPLAY - AI GENERATED

Sissy&#039_s tasks to complete and earn good girl points - FEMINIZATION ROLEPLAY - AI GENERATED

XVideos 9 months ago

Sissy Slut Training Part 3

Premium VR 9:41

Sissy Slut Training Part 3

SexLikeReal 1 month ago

Girl Brain Sissy Training. 1000 Strokes To Feminization

Premium HD 15:37

Girl Brain Sissy Training. 1000 Strokes To Feminization

Clips4sale 3 weeks ago

Take the quiz for bottom sissies - ROLEPLAY JOI AI

Take the quiz for bottom sissies - ROLEPLAY JOI AI

XVideos 8 months ago

That night your step-sister got you to eat your cummies SO HOTT

Premium HD 18:25

That night your step-sister got you to eat your cummies SO HOTT

XVideosRed 4 months ago

So You Want To Feel Like A Girl?

Premium VR 19:16

So You Want To Feel Like A Girl?

SexLikeReal 2 years ago

Sissy Training Night with Her Black Bull (JOI Animation)

Premium HD 5:10

Sissy Training Night with Her Black Bull (JOI Animation)

XVideosRed 4 months ago

Looper 1 No Cock Needed &mdash_ Just Moaning and Bucking Forever

Premium HD 5:49

Looper 1 No Cock Needed &mdash_ Just Moaning and Bucking Forever

xnxxGold 4 months ago

Loser Gooner Game 3 Rounds Test CLIP 1

Premium HD 22:47

Loser Gooner Game 3 Rounds Test CLIP 1

XVideosRed 3 years ago

Censored AI Girls (HD MP4)

63% 4K 0:32 / 17:34

Censored AI Girls (HD MP4)

Clips4sale 2 years ago

Answer this fucking test and see if you&#039_re a sissy (FEMINIZATION ROLEPLAY - AI GENERATED)

Answer this fucking test and see if you&#039_re a sissy (FEMINIZATION ROLEPLAY - AI GENERATED)

XVideos 11 months ago

Censored AI Girls (SD MP4)

53% 4K 0:32 / 17:34

Censored AI Girls (SD MP4)

Clips4sale 2 years ago

I&#039_ll fuckin&#039_ help you become the sissy bitch you were meant to be, you fuckin&#039_ fairy! I&#039_ll guide you through your fuckin&#039_ transformation and make you my little sissy slut, you fuckin&#039_ faggot! (FEMINIZATION ROLEPLAY - AI GENER

I&#039_ll fuckin&#039_ help you become the sissy bitch you were meant to be, you fuckin&#039_ fairy! I&#039_ll guide you through your fuckin&#039_ transformation and make you my little sissy slut, you fuckin&#039_ faggot! (FEMINIZATION ROLEPLAY - AI GENER

XVideos 10 months ago

Black girl is your mistress and wants to play with your sweet ass - ROLEPLAY AI

Black girl is your mistress and wants to play with your sweet ass - ROLEPLAY AI

XVideos 8 months ago

Practice for the glory then suck at the Gloryhole INTERACTIVE DILDO SUCK INTRUCTIONS

Premium HD 22:32

Practice for the glory then suck at the Gloryhole INTERACTIVE DILDO SUCK INTRUCTIONS

XVideosRed 4 months ago

Diapered SISSY gets Cucked at Office Party

38% HD 0:56 / 16:09

Diapered SISSY gets Cucked at Office Party

Clips4sale 1 year ago

Frustration and Ejaculation for this Useless Sissy - Maîtresse Julia

62% HD 0:10 / 17:15

Frustration and Ejaculation for this Useless Sissy - Maîtresse Julia

LoyalFans 1 year ago

Ebony cutie is your mistresse and desires to play with your pleasing butt - ROLEPLAY AI

Ebony cutie is your mistresse and desires to play with your pleasing butt - ROLEPLAY AI

Ebony8 8 months ago

Sissy la grosse salope (pegging) - Sissy the big slut (pegging)

65% HD 0:10 / 14:51

Sissy la grosse salope (pegging) - Sissy the big slut (pegging)

LoyalFans 5 months ago

Natasha Vega - Sissy Training

Premium VR 8:43

Natasha Vega - Sissy Training

SexLikeReal 1 year ago

Mistress gonna fuckin&#039_ transform you into a sissy fucktoy, you little bitch! Gonna make your fuckin&#039_ ass sore and use it like the fuckin&#039_ hole it is, you goddamn faggot! (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistress gonna fuckin&#039_ transform you into a sissy fucktoy, you little bitch! Gonna make your fuckin&#039_ ass sore and use it like the fuckin&#039_ hole it is, you goddamn faggot! (FEMINIZATION ROLEPLAY - AI GENERATED)

XVideos 11 months ago

MISTRESS GAIA - SISSY TRIPLE FUCKING - HD

57% HD 0:26 / 12:22

MISTRESS GAIA - SISSY TRIPLE FUCKING - HD

Clips4sale 1 year ago

Sissy Training Day Feat Astrodomina

Premium VR 10:38

Sissy Training Day Feat Astrodomina

SexLikeReal 2 months ago

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