Search results: Sissy Boy Slave
Showing 1 - 78 of 56,151 videos (0.024 seconds)

lingerie,POV,bdsm,fetish,femdom,sissy

HD

Worship My Big Hard Tool, Sissy Boy!

09:54 0 Views 90%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,forced-bisexual,forced-gay,crossdresser-femdom,forced-crossdresser,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Transforming You Into A Sissy Slut: Creating The Ultimate Pretty Boy

04:30 7k Views 60%

slut,young,old,lingerie,bbw,used,sissy

Submissive Twink Dominates Experienced MILF

10:03 8.4k Views 80%

domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn

HD

I Will Make You My Obedient Sissy Sluttoy

08:52 2.3k Views 80%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Submit To Your Mistress: A Night Of Sissy Boy Pleasure And Submission

04:37 2.8k Views 67%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,forced-bisexual,forced-gay,crossdresser-femdom,forced-crossdresser,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Wear These Sexy Pink Panties, You Sissy Slut!

09:17 2.2k Views 72%

anal,blowjob,strapon,cuckold,sissy

HD

Sissy Cuck Hubby Takes Massive Strapon Pegging!

06:28 2k Views 62%

humiliation,femdom,sissy,humiliatrix,dommes,crossdresser-torrents,crossdress-dommes,crossdressing-movies,crossdress-download,crossdresser-passwords

HD

You Look Like A Little Sissy Boy To Me - A Filthy Anal Adventure

04:04 944 Views 80%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,forced-bisexual,forced-gay,crossdresser-femdom,forced-crossdresser,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Training A Pathetic Sissy Boy Into The Ultimate Cock-Hungry Slut

08:01 998 Views 64%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

I'm A Filthy Sissy Boy Who Loves To Get Used!

07:24 636 Views 68%

humiliation,bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,humiliation-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

Unleash Your Inner Sissy Slut

07:59 255 Views 83%

humiliation,bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,humiliation-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

Get On Your Knees And Slurp My Huge Throbbing Cock Like A Good Little Sissy Bitch!

04:30 535 Views 100%

interracial,blowjob,hairy,humiliation,fetish,cheating,cuckold,big-cock,doggy-style,big-dick,sissy,small-tits,cuck,bbc,big-black-cock

HD

Penelope Reed Bounces On Big Black Cock And Dominates Her Submissive Boy Toy

06:25 1.6k Views 72%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,forced-bisexual,forced-gay,crossdresser-femdom,forced-crossdresser,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

You're Going To Be My Naughty Little Sissy Slut

07:19 751 Views 72%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,forced-bisexual,forced-gay,crossdresser-femdom,forced-crossdresser,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

I'll Make You My Horny Little Sissy Slut

05:14 307 Views 83%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

I'll Turn You Into A Horny Little Sissy Slut

03:58 150 Views 100%

anal,slave,mistress,bbw,femdom,sissy,humilation

Big Booty Mistress Dominates And Roughly Fucks Her Submissive Sissy Boy

06:00 692 Views 72%

domination,bdsm,fetish,slave,mistress,femdom,humiliatrix,slavetraining,gay-fantasy,bisexual-fantasy,femdom-pov,femdom-clips

HD

You Will Be My Obedient Little Sissy Slut

09:53 144 Views 92%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Cum Craving Sissy Slave Begs For More!

02:52 61 Views 77%

amateur,webcam,mistress,training,femdom,camgirl,boy,joi,sissy,loser,instructions,instructional

Novice Camslut Teaches Sub Servant How To Please Her Live On Cam

05:25 688 Views 84%

humiliation,bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,humiliation-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

You Will Be My Obedient Sissy Fuck Toy

09:47 482 Views 79%

panties,lingerie,POV,bdsm,femdom,sissy,feminization

HD

I Desire A Submissive Sissy Boy Toy To Serve Me

08:17 116 Views 97%

stockings,sexy,amateur,homemade,vibrator,lingerie,fetish,new,twink,sissy,feminization,femboy,solo-masturbation,tiny-dick,sexy-clothes,solo-boys

HD

Busty Babe Seduces Sissy Boy Into Naughty Vibrator Play

07:26 0 Views 88%

anal,stockings,dildo,panties,bra,thong,miniskirt,high-heels,vibrator,nylon,pantyhose,underwear,ecchi,sex-machine,cage,sissy,feminization,femboy,thigh-highs,anal-whore,anal-fingering,big-dildo,magic-wand,anal-masturbation,anal-orgasm,chastity-cage,cock-cage,only-anal,large-butt-plug,intense-anal,bdsm-3d,destroyed-gape,dap-with-toys,playing-with-2-toys,monster-cock-toy,anal-with-sex-machine

HD

Stretching His Limits: Sissy Boy Tackles Sex Machine In Wild Anal Workout!

56:10 0 Views 97%

POV,bdsm,femdom,sissy,feminization

HD

I Will Dominate And Fuck Your Sissy Ass Into Submission

07:47 235 Views 62%

anal,hot,sexy,high-heels,tranny,shemale,beautiful,cum-swallow,feet,femdom,worship,big-dick,sissy,chastity,feets,trample,foot-fetish,cum-on-feet,shoe-job,jessica-bloom

HD

High Heel Domination: Sissy Slave Crushed And Served By Jessica Bloom & Polieana

05:17 631 Views 83%

anal,dildo,hardcore,milf,rough,toys,pussy-licking,bdsm,strap-on,big-ass,fisting,orgasm,fist,femdom,milfs,big-tits,sissy,anal-sex,ass-play,whole-fist

HD

Voluptuous Blonde Bombshell Aiden Starr Ravages Submissive Sissy With Bondage, Anal Pounding, And Hardcore Fisting

08:00 35 Views 89%

asshole,asian,ass-licking,strapon,slave,mistress,femdom,sissy,pussyman,ass-worship,deviant-david

HD

Mena Mason Dominates Her Obedient Ass-Eating Slave

06:01 0 Views 81%

bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

I Knew Your Sissy Ass Was Begging For It All Along

06:42 1k Views 73%

POV,bdsm,femdom,sissy,feminization

HD

We're Going To Make You A Filthy Sissy Slut

06:58 652 Views 69%

humiliation,bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,humiliation-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

You Are Going To Be My Filthy Sissy Toy

07:19 260 Views 85%

humiliation,bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,humiliation-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

You Are Going To Be My Filthy New Sissy Slut

07:47 981 Views 94%

humiliation,femdom,sissy,humiliatrix,dommes,crossdresser-torrents,crossdress-dommes,crossdressing-movies,crossdress-download,crossdresser-passwords

HD

Whore Begs To Be Filled With Cock Like The Desperate Sissy He Is

06:54 43 Views 76%

humiliation,femdom,sissy,humiliatrix,dommes,crossdresser-torrents,crossdress-dommes,crossdressing-movies,crossdress-download,crossdresser-passwords

HD

You Look So Hot As A Sissy Slut

04:05 105 Views 96%

humiliation,bdsm,femdom,sissy,crossdress,sissification,feminization,femdom-pov,humiliation-pov,crossdresser-tube,fem-clips,crossdress-clips,crossdresser-torrents,crossdresser-forums,crossdresser-sex,bi-crossdresser,femdom-crossdressing

HD

Grovel For This Massive Dick, You Submissive Crossdresser

07:08 551 Views 0%

humiliation,domination,bdsm,fetish,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Slip Into These Frilly Pink Panties And Embrace Your Inner Sissy Slut

09:16 144 Views 71%

cumshot,thong,femdom,sissy

HD

Sissy Twink Gets Punished And Orgasms

00:21 0 Views 79%

humiliation,bdsm,slave,mistress,femdom,chastity,denial,ballbusting,forced-fem,male-chastity,female-domination,forced-bi,femdom-pov,cum-eating-instruction,mistress-pov,male-slaves

HD

Beg For Daddy's Hard Cock In Your Tight Little Hole

04:11 2k Views 68%

interracial,wife,blacks,submissive,domination,couple,femdom,cuckold,big-cock,big-dick,sissy,hubby,cuckolding,cuckolds,black-cock,black-cocks,cheating-wife,black-men,interracial-sex,white-wife

Submissive Husband Gazes On As His Wife Devours Massive Black Cock Inches Away

05:16 976 Views 78%

anal,big,tits,spanking,toys,strapon,bdsm,mistress,femdom,degrade,sissy

HD

Submissive Guy Gets Banged By Strapon Queen And Mistress In Booty

08:18 0 Views 72%

babe,petite,upskirt,milf,brunette,fingering,closeup,teacher,tease,erotica,roleplay,taboo,please,story,sissy,cocktease,chastity,stepmom,stepmother,stepson

HD

Daddy's Naughty Trap For Step-Son

00:17 321 Views 74%

asian,bdsm,bondage,slave,gay,exam,twink

Skinny Asian Twink Dominated And Degraded

02:13 425 Views 73%

pussy,hardcore,tits,babe,pornstar,ass,milf,tattoo,threesome,bigtits,puba

HD

Hot MILFs Jen And Savana Dominate And Strap-on Fuck A Submissive Sissy!

07:38 1.1k Views 97%

pussy,squirt,bdsm,fetish,femdom

HD

Seductive Mistress Dominates Naughty Sissy Boy

10:02 68 Views 94%

domination,strapon,pain,femdom,dominatrix,leather

Submissive Sissy Slut Gets Dominated And Fucked Like A Sex Slave

07:25 756 Views 86%

humiliation,domination,fetish,femdom,slaves,cum-eating-instructions,femdom-pov,humiliation-pov,cum-eating-femdom,femdom-humiliation,femdom-clips,cum-eating-fetish

HD

You're A Filthy Cock-slurping Sissy Slut, Aren't You? Cum Swallowing Instruction

04:39 413 Views 60%

anal,stockings,milf,brunette,uniform,toys,fishnet,lingerie,fetish,strap-on,femdom,big-boobs,special-locations

BDSM Queen Dominates Sissy Boy's Tight Ass With Strap-On Cock

28:54 187 Views 76%

cumshot,dildo,interracial,pornstar,wife,toy,humiliation,american,fetish,cheating,cuckold,husband,cuck,bbc,monster-cock,big-black-cock

HD

Layla And Her Submissive Boy Toy Get Destroyed By A Massive Black Cock

06:55 214 Views 94%

cumshot,sex,pussy,hardcore,tits,pornstar,ass,milf,blowjob,bigtits,nude,kiki-daire,puba

HD

Kiki Daire And Aiden Pound A Sissy Boy With A Huge Black Dildo!

10:38 173 Views 67%

blonde,milf,chubby,watching,cash,money,big-tits,cuckold,big-boobs,cash-for-sex,amateur-cuckold,hunt4k,czech-couple-money,wife-for-cash,milf-for-cash

HD

HUNT4K. Sissy Boy Watches As His Date Pleases Another Man

09:57 669 Views 78%

anal,boots,lingerie,humiliation,domination,prolapse,foot-fetish,foot-worship,curvy-body,0-pussy

HD

Hot Russian Domme Fucks Submissive Sissy Boy With Giant XL Ball Gag And Harness TWT010

01:00 578 Views 94%

toys,POV,bondage,femdom,chastity

HD

I Always Knew You Were A Sissy Boy Who Craves A Dominant Touch!

07:34 762 Views 83%

glasses,blondes,humiliation,domination,blue-eyes,feminization,long-hair,cock-tease,female-domination,red-lips,femdom-pov,tease-denial

Submission Of A Pathetic Sissy Boy For The Pleasure Of Goddess Kyaa

01:32 308 Views 100%

cumshot,european,blonde,handjob,amateur,homemade,wife,cute,girlfriend,cumming,orgasm,massage,rimming,hottest,short-hair,hot-girl,blonde-guy,home-alone,amateur-couple,real-couple

HD

Sensual Stroke Session For A Naughty Sissy Boy

10:37 259 Views 66%

cum,creampie,blowjob,tattoo,shaved,humiliation,fetish,cheating,cuckold,small-tits

HD

Submissive Sissy Boy Cleans Up Charlotte Sartre's Dirty Mess

07:34 463 Views 69%

lingerie,POV,bdsm,fetish,femdom,bisexual

HD

You Are My Submissive Cock-sucking Slut

07:19 20 Views 80%

wife,submissive,humiliation,housewife,cuckold,wives,cuckolding,cuckolds,black-cock,monster-cock,cheating-wives,black-cocks,big-black-dick,white-girls,interracial-cuckold,interracial-sex,white-wife,white-sluts

Sultry Blonde Sissy Devours Wife's Juicy Ass Covered In Hot Cum

05:04 253 Views 77%

cumshot,interracial,pornstar,milf,mature,wife,humiliation,american,fetish,cheating,cuckold,cum-eating,husband,cuck,bbc,black-cock,monster-cock,big-black-cock

HD

Helpless Submissive Twerp Fails To Please Insatiable Micky Lynn

07:00 279 Views 74%

fetish,gay-anal

HD

Tiny Twink Craves Giant Cock In His Tight Hole

03:00 0 Views 96%

cute,femboy,sissy-boy,sissy-cum,sissy-ass,sissy-solo,sissy-cumshot,femboy-cum,femboy-cumshot,cute-sissy,cute-femboy,sissy-cock,femboy-trap

HD

Naughty Asian Sissy Boy Tempts With Cock Play And Explosive Finish

05:01 111 Views 63%

european,blonde,babe,strapon,strap-on,horny,bisexual,kinky,pegging,short-hair,role,perverted,sissy-boy,chastity-belt,cock-cage,skinny-girl,girl-fucks-guy,real-homemade-amateur,sissy-slave,peg-him

HD

Sensual Babe's Anal Obsession With Her Man

10:48 408 Views 66%

real,homemade,wife,fisting,extreme,weird,bisexual,kinky,husband,perverted,sissy-boy,amateur-couple,moaning-bitch,anal-games,real-amateur-couple,femdom-fisting,amateur-bisex,guy-fisted,fisting-anal-slave,anal-fisting-male

HD

Steamy Hottie Passionately Fisting Young Stud - Uncensored Homemade Spycam

08:29 782 Views 98%

interracial,housewife,couples,femdom,cuckold,big-cock,husband,big-dick,sissy,bbc,cuckolds,black-cock,monster-cock,black-cocks,cheating-wife,sissy-boy,black-men,interracial-sex,white-wife,black-bull

Pale-skinned Lad Is Ready To Submit As A Cock-hungry Cuckold Toy!

05:16 1k Views 100%

tranny,makeup,trans,crossdresser,cd,sissy,transformation,crossdress,feminization,sissy-boy,sissy-slut,teen-slut,cd-slut

HD

Makeover Madness: Step Dad's Sissy Transformation!

05:02 243 Views 69%

doggystyle,domination,strap-on,strap,crossdresser,bisexual,bi,pegging,sissy,femboy,anal-sex,pegged,sissy-boy,strapon-fuck,girl-fucks-guy,amateur-crossdresser,cute-twink-femboy,gay-strapon,fucking-sex-toy,passive-gay

Anastasia Dominatrix Pounds Submissive Sissy's Ass With Strap-On In Real Home BDSM Anal Action

02:59 282 Views 84%

latex,strapon,bdsm,slave,femdom,dominatrix,sissy-boy,high-hells,crosseder

HD

Sissy Boy Gets Dominated And Fucked In Intense BDSM Scene

10:34 1k Views 76%

anal,cumshot,cum,dildo,gaping,blowjob,slut,masturbation,gape,tranny,shemale,trans,sissy,face-fuck,sissy-boy,sissy-slut,dildo-riding,sissy-cum,sissy-fucked,bimbo-slut

HD

Sexy Bimbo Princess In Bubblegum Boots Rides Big Toy Until Orgasm

05:02 59 Views 99%

interracial,housewife,couples,femdom,cuckold,big-cock,husband,big-dick,sissy,bbc,cuckolds,black-cock,monster-cock,black-cocks,cheating-wife,sissy-boy,black-men,interracial-sex,white-wife,black-bull

Voluptuous Busty Wife Drives Pale Guy Crazy While Riding Big Black Cock

05:20 617 Views 97%

interracial,housewife,couples,femdom,cuckold,big-cock,husband,big-dick,sissy,bbc,cuckolds,black-cock,monster-cock,black-cocks,cheating-wife,sissy-boy,black-men,interracial-sex,white-wife,black-bull

Pale-skinned Male Voyeur Witnesses Massive Black Cock Thrusting In And Out Of His Horny Wife's Tight Pussy

05:22 689 Views 87%

interracial,housewife,couples,femdom,cuckold,big-cock,husband,big-dick,sissy,bbc,cuckolds,black-cock,monster-cock,black-cocks,cheating-wife,sissy-boy,black-men,interracial-sex,white-wife,black-bull

Voluptuous Blonde Dominates Weak White Guy

05:20 412 Views 95%

cumshot,european,blonde,handjob,real,homemade,fisting,slave,mistress,crazy,femdom,amateurs,kinky,kink,perverted,sissy-boy,amateur-couple,bi-couple,horeny,huge-load-cum

HD

Pounding And Exploding - Chick Fisting Dude With Massive Cum Explosion!

12:20 926 Views 75%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Slutty Sissy Boy Gets Hot In Lingerie

10:14 128 Views 64%

high-heels,blondes,humiliation,legs,cleavage,femdom,sissification,feminization,laughter,tease-and-denial,cock-tease,female-domination,sissy-training

Femdom Mistress Taunts Sissy Boy With Cock Tease POV

01:43 3.8k Views 0%

big,titty,strapon,femdom,pegging,peg,sissy

Harness-Wearing Princess Drills Kinky Sissy Boy Into Submission!

08:00 7k Views 100%

POV,humiliation,bdsm,fetish,mistress,femdom,dominatrix,domina,cuckold,joi,sissy,humiliatrix,domme,sph,cei,female-domination,findom,sissy-training

HD

Strap-On Goddess Dominates Sissy Boy With Humiliation Instructions

09:44 1.4k Views 95%

babe,handjob,amateur,group,spanking,bigboobs,strapon,mistress,femdom,whipping,dominatrix,domina,pegging,sissy,malesub,mediumboobs,malelave

HD

Slutty Babes Dominate And Fuck Sissy Boy With Strapons And Whips

04:10 578 Views 100%

uniform,submissive,bdsm,bondage,jerk,mistress,piss,dominatrix,sub,dominant,masochism,dom,maso,sissy,prodomme

HD

Seductive Femdoms Golden Shower Play With Submissive Sissy Boy

05:57 75 Views 100%

humiliation,domination,bdsm,fetish,slave,femdom,crossdresser,crossdressers,sissy,crossdressing,sissification,crossdresser-femdom,crossdresser-sex,crossdresser-porn,crossdress-humiliation

HD

Submission And Humiliation: Dominant Mistress Pleases Sissy Boy

05:36 97 Views 100%

Discover a premium selection of Sissy Boy Slave porn videos at LetMeJerk, where every scene is free to watch and always easy to find. Whether you're after classics or the latest trending clips, our library has something for every taste.

Fans of Sissy Boy Slave also check out: Femdom, Sissy, Bdsm, Humiliation, Fetish.

With over 56,151 unique Sissy Boy Slave videos ready to stream, you’ll never run out of options. Our easy-to-use site lets you browse and watch in hassle-free comfort.

Enjoy crisp visuals — almost 79% of our Sissy Boy Slave collection is available in HD for your viewing pleasure.

We update our Sissy Boy Slave category regularly, so there’s always something new and exciting to see. Bookmark this page to catch the latest releases and never miss a fresh upload!