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Discover the best of #sissy — 2,138 free HD videos, ranked so the hottest comes first. Use the filters to find exactly the #sissy content you crave.

YOUNG TWINK DEEPTHROATS! Amateur Throat Fucks Big Dick For The First Time

YOUNG TWINK DEEPTHROATS! Amateur Throat Fucks Big Dick For The First Time

323K views 85%

Christian playing with mature sissy crossdresser Jeanne before their scene

Christian playing with mature sissy crossdresser Jeanne before their scene

322K views 84%

Bubble butt cumming while riding dildo

Bubble butt cumming while riding dildo

320K views 93%

Bubble butt riding my sloppy ass on a dildo

Bubble butt riding my sloppy ass on a dildo

320K views 91%

No real man would touch themselves to this AUDIO ONLY SISSY JOI

No real man would touch themselves to this AUDIO ONLY SISSY JOI

305K views 69%

Gorgeous Dominatrix Mistress JOI

Gorgeous Dominatrix Mistress JOI

303K views 82%

Sissy Cuckold Cleans Bulls Cock

Sissy Cuckold Cleans Bulls Cock

291K views 92%

Veronica Way - Trap Moaning Masturbation

Veronica Way - Trap Moaning Masturbation

291K views 93%

Julia Femdom & chastity My pet wear chastity by command. Vid report

Julia Femdom & chastity My pet wear chastity by command. Vid report

284K views 75%

DOUBLE ORGASM SISSY DILDO ANAL RIDING SISSYGASM

DOUBLE ORGASM SISSY DILDO ANAL RIDING SISSYGASM

279K views 93%

Weird Guy Enjoys Being Treated Like A Whore

Weird Guy Enjoys Being Treated Like A Whore

279K views 80%

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

277K views 88%

Bubble booty femboy dildo in ass

Bubble booty femboy dildo in ass

277K views 89%

Cd sissy cum milking in glass and drinking everything

Cd sissy cum milking in glass and drinking everything

276K views 94%

Sissy tranny sucking, riding and cumming

Sissy tranny sucking, riding and cumming

274K views 89%

Sissy at Mercy of FemDom AsianNymphet

Sissy at Mercy of FemDom AsianNymphet

271K views 88%

Astolfo Fucking his Trap Pussy

Astolfo Fucking his Trap Pussy

261K views 91%

Take Your StepDaughter to Work Day

Take Your StepDaughter to Work Day

259K views 87%

horny teen slut fingering and busting a load

horny teen slut fingering and busting a load

257K views 91%

SISSYGASM orgasms Riding Dildo And Cumming. big dildo for Shemale

SISSYGASM orgasms Riding Dildo And Cumming. big dildo for Shemale

256K views 91%

College Twink Seth Knight Lets His Nerdy Gay Teacher Fuck Him For An “A”

College Twink Seth Knight Lets His Nerdy Gay Teacher Fuck Him For An “A”

248K views 91%

Men Acting Like Women Pegged By Dominatrixes

Men Acting Like Women Pegged By Dominatrixes

242K views 76%

TS Escort Breaks her Promise to You :( Sasha de Sade

TS Escort Breaks her Promise to You :( Sasha de Sade

242K views 87%

TS Lucia Maya in Shiny Latex Fingering, Dildo Fucking & Stroking to Orgasm

TS Lucia Maya in Shiny Latex Fingering, Dildo Fucking & Stroking to Orgasm

242K views 91%

Slut TGirl Sasha de Sade in Chastity Cock Cage

Slut TGirl Sasha de Sade in Chastity Cock Cage

240K views 91%

Sissy Cocksucking Faggot -Mrs Mischief milf femdom humiliation strap on pov

Sissy Cocksucking Faggot -Mrs Mischief milf femdom humiliation strap on pov

239K views 89%

SISSY TASK TRAINING + SISSY JOI REWARD VIDEO

SISSY TASK TRAINING + SISSY JOI REWARD VIDEO

237K views 84%

TransAngels - Let Me Teach You - Rob Yaeger, Venus Lux - Asian shemale

TransAngels - Let Me Teach You - Rob Yaeger, Venus Lux - Asian shemale

235K views 80%

Bubble bum femboy shows asshole booty

Bubble bum femboy shows asshole booty

233K views 91%

Uncut Sissy Shemale Playing w/ Her Tiny Cock After Cumming Hard

Uncut Sissy Shemale Playing w/ Her Tiny Cock After Cumming Hard

227K views 82%

Femdom spit & dirty talk for sissy slut humiliation pov lucywants camgirl

Femdom spit & dirty talk for sissy slut humiliation pov lucywants camgirl

226K views 78%

Subtitled Japanese cougars embarrassing cross dressing party

Subtitled Japanese cougars embarrassing cross dressing party

221K views 65%

Tricked into sissification tricked into chastity (New Vids on MANYVIDS)

Tricked into sissification tricked into chastity (New Vids on MANYVIDS)

220K views 78%

Mature Britt cocksucks dom in front of sissy

Mature Britt cocksucks dom in front of sissy

220K views 83%

Dominate Jock Jared Shaw Ass Pounds Skinny Twink RAW With His Huge Cock

Dominate Jock Jared Shaw Ass Pounds Skinny Twink RAW With His Huge Cock

219K views 92%

Podcast Ep10: Sissy Bimbo Slut Confessions (Audio)

Podcast Ep10: Sissy Bimbo Slut Confessions (Audio)

213K views 59%

morning fap and cumshot on stomach nbnabunny

morning fap and cumshot on stomach nbnabunny

211K views 93%

Hard Fucking Machines Sissygasm Orgasm Amal Sex

Hard Fucking Machines Sissygasm Orgasm Amal Sex

204K views 92%

Young Twink Femboy Fucked Hard In Hotel Room On Boyfriend’s Business Trip

Young Twink Femboy Fucked Hard In Hotel Room On Boyfriend’s Business Trip

203K views 89%

Link Loses Lulu to Ganon's Huge Green Cock

Link Loses Lulu to Ganon's Huge Green Cock

202K views 87%

Crossdresser Captured And Dominated By Three Mistresses

Crossdresser Captured And Dominated By Three Mistresses

189K views 71%

cocksucking lesson! HOT femdom strapon worship dirtytalk on CAM lucywants

cocksucking lesson! HOT femdom strapon worship dirtytalk on CAM lucywants

187K views 86%

Sissy trap with pink dildo

Sissy trap with pink dildo

186K views 87%

Chastity Femboy Playing Close-up with Thicc Dildo

Chastity Femboy Playing Close-up with Thicc Dildo

184K views 93%

Sissy Boy Pegged by Strap On Princess and Mistress in Ass

Sissy Boy Pegged by Strap On Princess and Mistress in Ass

184K views 78%

Psychedelic Shemale PMV

Psychedelic Shemale PMV

182K views 87%

Crossdressers Self Facial Cumshot Hattabi4ik ^_^

Crossdressers Self Facial Cumshot Hattabi4ik ^_^

179K views 90%

Pegging his ass

Pegging his ass

174K views 90%

Kinky Guy Becomes A Cheap Slut

Kinky Guy Becomes A Cheap Slut

173K views 75%

Sasha's Bar Tricks

Sasha's Bar Tricks

173K views 89%

How I Handle Small Penis Loser Boys - Cory Chase

How I Handle Small Penis Loser Boys - Cory Chase

169K views 83%

Goth gives Humiliation, Toilet Sissy Instructions

Goth gives Humiliation, Toilet Sissy Instructions

167K views 78%

Teen Transvestite Transformed And Dominated By A Couple

Teen Transvestite Transformed And Dominated By A Couple

165K views 79%

Sissy Atonement

Sissy Atonement

165K views 56%

Sissy Crossdresser Stuffed While Fucking a Flesh Light!

Sissy Crossdresser Stuffed While Fucking a Flesh Light!

162K views 92%

sissy porn ft BoringKate

sissy porn ft BoringKate

161K views 76%

Sissy Anal Training in Bath

Sissy Anal Training in Bath

160K views 90%

Bubble butt ass on a big dildo

Bubble butt ass on a big dildo

160K views 89%

crossdresser takes a big dick whenever its given

crossdresser takes a big dick whenever its given

159K views 85%

BBC Gloryhole Orgy

BBC Gloryhole Orgy

159K views 84%