Search results: Lazy Sissy
Showing 235 - 312 of 5,271 videos (0.016 seconds)

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

97% 1 Votes

Views: 0

Duration: 56:10

blonde,milf,rough,amateur,curvy,solo,latex,humiliation,domination,bdsm,close-up,strap-on,beauty,femdom,cougar,dirty-talk,cfnm,glamour,newbie,alternative,humiliatrix,punishing,pawg,sissification,ass-worship,edging,bratty,girl-next-door,solo-girl,sexy-clothes,onion-booty,pretty-face,sissy-humiliation,female-pov,young-woman,slut-humiliation,slave-degradation,whore-humiliation

HD

Sissy Seduction: MILF Domination & Humiliation With Arya Grander

14:58 193 Views 87%

stockings,blonde,sexy,milf,amateur,curvy,solo,latex,POV,humiliation,domination,skirt,strap-on,femdom,leather,dirty-talk,glamour,alternative,humiliatrix,punishing,pawg,sissification,ass-worship,edging,girl-next-door,solo-girl,sexy-clothes,onion-booty,ruined-orgasm,sissy-humiliation,mature-woman,female-pov,young-woman,goddess-worship,slut-humiliation,slave-degradation,whore-humiliation

HD

Hot MILF Dominates With Strap-On In POV Video Featuring Arya Grander

04:45 0 Views 70%

anal,amateur,homemade,bdsm,fetish,bondage,couple,mistress,femdom,sex-machine,kink,big-boobs,chastity,huge-dildo,sex-slave,big-dildo,anal-orgasm,hot-girlfriend,sissygasm,hot-boyfriend

HD

Sissy Slave Gets Dominated By Mistress With Huge Dildo And Sex Machine For Ultimate Pleasure!

05:54 123 Views 69%

cowgirl,tranny,cross,sissy,tanga,putita,sentones,gay-sex,gay-anal,pasiva,trajecito-de-red

HD

Bottom Gets A Wild Ride And Moans Loudly

01:00 211 Views 69%

sissy-pink-panties,sissy-bra,crossdresser-bra

HD

Man Gets Off Flashing His Pretty Pink Panties

05:18 0 Views 75%

blowjob,amateur,teacher,hentai,anime,boss,family,korean,stepmom,stepsister,step-mom,step-sister,anime-hentai,little-step-sister,anime-cartoon,big-step-sister,nhentai,manhwa-hentai,pornhwa,manhwahentai

HD

Spicy Stir-Fry Seduction: A Beginner's Guide To Heating Things Up In The Kitchen

00:13 403 Views 80%

porn,sex,fucking,milf,blowjob,wife,busty,POV,big-ass,family,fucks,big-tits,taboo,big-boobs,pornos,stepmom,stepmother,stepson,stepmommy,stepfantasy

HD

Seductive Step-MILF Jessica Ryan Teaches Her Stepson The Hard Way

06:57 62 Views 73%

babe,blowjob,handjob,rough,amateur,group,toy,spanking,bigtits,sextoy,strapon,femdom,femaledomination,pegging,sissy,mediumboobs,straponpegging,submissivemale

HD

BDSM Babes Gang Up On Guys With Strap-Ons And Spankings!

05:00 0 Views 69%

anal,blonde,milf,latex,femdom,german,domina,deutsch,sissy,deutsche,german-bdsm,german-fetish

HD

Blonde Mistress In Latex Dominates And Fucks Her Submissive Slave

23:28 106 Views 96%

wife,dirty-talk,cuckold,joi,sissy,pawg,big-booty,phat-ass,long-hair,solo-masturbation,raceplay,slut-wife,amateur-milf,bbc-wife,bbc-whore,bbc-worship,amateur-pawg,bbc-role-play

HD

Voluptuous PAWG Sara Swirls Drives Black Monster Cock Wild!

02:14 0 Views 77%

guy-panties,sissy-thong,a-mature-sissy

HD

Stud Struts His Stuff In A Sexy Thong

03:08 0 Views 71%

domination,bdsm,fetish,mistress,femdom,sissy-slut,cum-eating-instruction,crosseder,sissy-hoy

HD

Kinky Mistress Takes Charge Of Naughty Crossdresser

10:02 201 Views 63%

sex,milf,POV,domination,mistress,femdom,facesitting,cuckold,sissy-boy

HD

Hot POV Action: Pounding A Horny Cougar!

07:16 0 Views 64%

cum,cock,solo,tranny,masturbate,orgasm,trans,big-cock,big-dick,gay-amateur

HD

Dainty Diva Stroking It Hard

05:06 0 Views 68%

training,femdom,joy,trainer,sissy,hypno,sissification,feminization,brainwashing,sissy-hypno,asmr,healthy-sissy-series,hynposis

HD

Spank Me Silly - Sissification Seduction Show

02:23 127 Views 80%

porn,sex,pussy,creampie,petite,riding,teenie,pussyfucking,shower,shaved-pussy,big-ass,little,18yo,big-dick,sissy,towel,stepsister,stepbro,tight-pussy

HD

Stepsister Seduces Me With Her Wet Towel After Shower

05:13 0 Views 61%

anal,cum,facial,fucking,hardcore,sexy,interracial,ass,blowjob,rough,amateur,deepthroat,bigcock,tranny,shemale,trans,sissy,chastity,bbc,femboy

HD

Intense Anal Pounding Ends With Trans Facial Delight

05:17 0 Views 87%

anal,teen,pigtails,miniskirt,gape,tranny,socks,transexual,futanari,futa,sissy,trap,mexicana,bbc,femboy,big-toy,anal-orgasm,bbc-anal,shemale-bbc

HD

Curvy Latina Teen's Big Boobs Bounce In XXX Mexicana Adventure

16:33 0 Views 60%

bdsm,chair,bondage,femdom,pegging,prostate,sissy,ass-play,anal-play,anal-hook,anal-training,prostate-orgasm,prostate-milking

HD

Begging For Relief: Prostate Edging Hell With Anal Hooks And A Fucking Machine

01:10 0 Views 61%

sissy-tight-panties,crossdresser-feels-horny,guy-loves-showing-his-panties

HD

Naughty Sissy Squeezes Into Seductive Panties

06:23 0 Views 78%

hardcore,creampie,tranny,big-ass,horny,trans,bbc,big-butt

HD

Busty Babe Ariana Gets Naughty In Toronto: A Sissy Adventure

01:39 0 Views 87%

stockings,dildo,babe,amateur,highheels,strapon,heels,3some,doubledildo,femdom,pegging,naturalboobs,mediumboobs,straponpegging

HD

Femdom Babes Give Sissy Guy A Wild 3-Way Dildo Pegging Experience!

05:00 0 Views 63%

cumshot,babe,milf,handjob,amateur,group,bigboobs,strapon,femdom,whipping,crossdresser,pegging,sissy,straponpegging,mulher-com-homem-grei

HD

Sissy Maid Gets Dominated And Pegged By Gang Of Sexy Mistresses

05:00 23 Views 97%

dildo,amateur,homemade,solo,deep,sissy,gap,soloboy,gay-anal,sissy-training,boy-pussy

HD

I'm Here For Naughty Talk And Filthy Titles! Just Let Me Know What You Need, And I'll Bring On The Sexy And Spicy Language For You.

01:12 0 Views 72%

anal,milf,blowjob,brunette,riding,doggystyle,tattoo,amateur,high-heels,lingerie,deep-throat,humiliation,domination,cunnilingus,ass-to-mouth,bedroom,femdom,missionary,big-tits,bisexual,pussy-eating,reverse-cowgirl,cuckold,big-cock,piledriver,punishing,1-on-1,sissy-humiliation,white-skin,goddess-worship,gapes-gaping-asshole,spoon-position,ass-to-pussy-atp,anal-creampie-to-other-girls-mouth,farting-anal-creampie

HD

Backdoor Mess, Farting Cum, And Cuckold Shame

00:30 0 Views 99%

sexy,babe,panties,amateur,homemade,fishnet,solo,lingerie,cute,close-up,shaking,bedroom,slapping,training,twink,transsexual,bisexual,taboo,black-hair,glamour,rocker,alternative,sissification,twerking,clitty,big-butt,perfect-ass,young-man,ass-clap,solo-boys,cock-play,sissy-humiliation,no-tattoos,bisexual-gay

HD

From Macho To Sissy: Seductive Journey In White Lingerie

00:35 0 Views 96%

anal,amateur,homemade,bdsm,fetish,bondage,mistress,femdom,big-tits,sex-machine,big-boobs,hot-girl,fucking-machine,sex-slave,slave-training,big-dildo,orgasm-denial,sissy-training,balls-deep-anal

HD

Ass Worship And Backdoor Drilling With The John Thomas Anal Torpedo For Submissive Slaves Pleasuring Mistress

14:01 127 Views 64%

anal,ass,thong,white,solo,fishnets,shemale,fetish,fisting,trans,crossdresser,mtf,sissy,thin,pawg,bubble-butt,femboy,anal-gape,pink-hair,extreme-anal,compialation

HD

Bootylicious Babe Tiffany's Wild Anal Adventure With Giant Ribbed Dildo!

19:58 0 Views 67%

stockings,sexy,tranny,trans,garters,transexual,kinky,sissy

HD

Spin Me Round And Get Down: A Steamy Encounter!

00:30 0 Views 100%

sissy-panty,crossdresser-panties,tranny-panties

HD

Shemale Gets Wild In Frilly Underwear

05:42 0 Views 88%

amateur,toys,anal-sex,big-toy,sundre-sissy

HD

Wild Cowgirl Rides Cowboy In Sundre, Alberta!

05:32 0 Views 85%

crossdresser-panties,tranny-panties,sissy-satin-panties

HD

Sissy Hubby Caught In Panty Raid

05:03 225 Views 80%

sexy,bra,chubby,solo,jerk,pants,crossdresser,paja,sissy,bragas,gordito,sujetador

HD

Hot Yequis Strips Down In Sexy Lingerie To Show Off Her Kinky Side!

02:02 235 Views 67%

blonde,brunette,amateur,group,spanking,strapon,babes,slapping,femdom,pegging,naturalboobs,closeups,mediumboobs,straponpegging

HD

Bend Over & Take It Like A Man: Sissified Stud Dominated By A Pack Of Horny Femdom Goddesses!

05:00 121 Views 77%

tranny-panties,cd-panties,a-mature-sissy

HD

Naughty She-Male Seductively Strips Off Lacy Lingerie

04:03 0 Views 98%

cd-panties,sissy-panty-tease,tranny-panty-try-on,crossdresser-blue-panties

HD

Naughty Sissy Struts In Lacy Thong

03:27 0 Views 79%

sissy-bra,cd-shorts,tranny-bra

HD

Panty-Clad Hubby Struts His Stuff In His Mrs.' Mini Shorts!

04:22 0 Views 68%

porn,latina,petite,hottie,brunette,amateur,bigbutt,tightpussy,bigass,fetish,cute,tight,babes,teenporn,sissy,hotlatina,cuteteen,sissified,smokingfetish,sissyfication

HD

Fiery Hot Smoking Session - Dominating Your Sissy

03:48 0 Views 93%

glasses,masturbation,masturbate,orgasm,femdom,loving,joi,sissy,domme,feminization,feminine,gentle,femdom-joi,sissygasm,mommy-domme,anal-joi,gentle-femdom,ass-play-joi,affirming

HD

Naughty Step-Mommy Takes Control And Unleashes Your Sissygasm - Watch The Full Video On Veggiebabyy Manyvids!

01:03 0 Views 76%

sissy-shorts,tranny-bra,a-mature-cd

HD

Naughty Hubby Struts His Stuff In Wife's Tiny Shorts!

02:12 0 Views 74%

cumshot,cum,teen,hardcore,slut,homemade,cowgirl,shemale,trans,crossdresser,cd,sissy

HD

Massive Sissy Orgasm Explosion

01:32 0 Views 62%

cumshot,facial,hot,sexy,blowjob,69,tranny,shemale,beautiful,trans,hotel,ts,dani,ladyboy,big-cock,big-dick,sissy,femboy,sucking-dick,jessica-bloom

HD

Sloppy Sensations: Jessica Bloom And Dani Diving Deep

05:31 393 Views 87%

teen,hardcore,petite,blowjob,real,amateur,teenie,smalltits,POV,curves,big-ass,hardsex,reality,small-tits,big-butt,jack-vegas,veronica-church

HD

Case No. 7906233 - Caught Red-Handed: Lazy Thief Gets More Than Bargained For With Veronica Church & Jack Vegas

08:16 26 Views 69%

ass,white,fishnets,tranny,shemale,crossdresser,sissy,trap,femboy,blond-hair,butt-girl,tiffany-ciskiss

HD

Adorable Trap Doll Tiffany Ciskiss Bares It All

01:09 0 Views 82%

hardcore,slut,tranny,shemale,public,big-ass,ladyboy,kinky,sissy,ligerie,exhibisionism,lgtbi,shemale-ass,aire-libre,crossdresers

HD

Farmyard Frills: Crossdressing Cutie Gets Dirty Outdoors With Horny Peasant

15:18 0 Views 81%

anal,cum,hardcore,amateur,homemade,high-heels,domination,bdsm,fetish,bondage,mistress,crossdresser,clinic,punishment,cage,sissy,cane,dungeon,chastity,fucking-machine

HD

Spanking Sensation: Mistress April's Cane Challenge - 1000 Ways To Redefine Pain

15:58 0 Views 78%

hardcore,sucking,brazilian,homemade,deepthroat,submissive,humiliation,tranny,bdsm,trans,big-dick,sissy,face-fuck,anal-sex,white-guy,cross-dressing,anal-plug,podiatry,aline-monteiro-ts,alexxxkidd

HD

AlexxxKidd Gets Dominated, Feminized, And Used By Trans Domme Aline Monteiro

06:53 51 Views 0%

anal,sex,masturbation,tranny,shemale,cd

HD

Leena's Naughty Sissy Adventures

04:32 0 Views 72%

outside,sissy,faggot

HD

Begging To Be Used: Sissy Slut Lusting In The Great Outdoors

00:58 21 Views 71%

blonde,babe,handjob,amateur,strapon,femdom,sub,pegging,sissy,maleslave,mediumboobs,highheelboots,submissiveguy

HD

Domina Delight: Pegging Pleasures And Tugging Tease

04:00 0 Views 99%

anal,teen,pigtails,miniskirt,gape,tranny,socks,transexual,futanari,futa,sissy,trap,mexicana,bbc,femboy,big-toy,anal-orgasm,bbc-anal,shemale-bbc

HD

Slutty Tlalpan Prostitute Gets Nailed Doggy Style

05:26 352 Views 60%

anal,latex,fetish,femdom,goddess,rubber,mean,billiards,sissy,mistress-tatjana

HD

Poolside Seduction With A Divine Playmate

00:45 0 Views 70%

sissy-ass,amateur-sissy,tranny-panties,cd-thong

HD

Struttin' Stud In Tighty-Whitey Tease

03:22 0 Views 95%

amateur-sissy,tranny-satin-panties,cd-white-bra

HD

Pulsating With Desire: CD Struts In Sultry Black Lingerie

04:03 0 Views 88%

amateur,homemade,toys,fetish,mistress,femdom,kinky,double-penetration,pegging,sissy,big-boobs,double-dildo,double-anal,anal-sex,deep-anal,huge-dildo,orgasm-denial,hot-girlfriend,hot-boyfriend

HD

Double The Trouble: Pegging And Double Anal Penetration With Top-Notch Toys

11:59 44 Views 100%

hardcore,milf,blowjob,busty,big-ass,big-tits,stepmom,hardcore-sex,hardcore-fuck,milf-sex,best-blowjob,hot-milf,busty-milf,milf-porn,milf-blowjob,big-cock-blowjob,big-tits-stepmom,hot-stepmom,busty-stepmom,big-ass-stepmom

HD

Thicc Step-MILF Siri Dahl Gives Lazy Stepson A Lesson With His Huge Dong

06:00 0 Views 86%

anal,cumshot,cum,blonde,sexy,cock,slut,amateur,solo,tranny,orgasm,trans,crossdresser,sissy,chastity,feminization,femboy,clitty,small-cock,eat-own-cum

HD

Chaste Cuties Swallow Every Last Drop Of Cum

06:14 0 Views 71%

cumshot,cum,high-heels,boots,masturbation,latex,tranny,shemale,fetish,trans,sissy,cum-in-mouth,femboy,latex-boots,thigh-high-boots,latex-gloves,latex-stockings,shemale-latex,sissy-latex

HD

Seductive Sissy Slips Into Latex, Stilettos, And Swallows Every Drop!

05:02 0 Views 85%

blonde,milf,handjob,homemade,whore,bondage,femdom,crossdresser,kinky,hottest,short-hair,sissy,perverted,stepmom,tied-up,amateur-couple,huge-load,sissy-training,amateur-homemade,hot-couple

HD

Step Mom's Naughty Lesson: Making This Femboy Gush Like A Geyser

05:31 0 Views 69%

anal,cumshot,dildo,hot,sexy,riding,slut,moaning,shemale,beautiful,cum-swallow,trans,cum-eating,big-dick,sissy,carrot,femboy,anal-orgasm,anal-stretching,neotori,jessica-bloom

HD

Massive Carrot Toy Stretching Jessica's Bloom

08:38 489 Views 63%

latina,shemale,big-ass,ladyboy,sissy-training,sandra-zanerri

HD

Bootylicious Babe Sandra Zanerri Gets A Rough Anal Lesson: Part 2

02:37 104 Views 90%

anal,3d,ass,threesome,shemale,cartoon,animation,futa,animated,double-anal,anal-sex,guy-fucks-shemale,shemale-fucks-guy,3d-blowjob,3d-shemale,shemale-milf,3d-shemale-milf,futanari-animation

HD

Double Trouble: Sissy Guys Get Freaky With MILF Shemale In Hot Anal Threesome - Animated Futanari Fun!

10:54 1.8k Views 100%

slut,tranny,trans,gostosa,gay-sex,gay-anal,gay-porn,gay-masturbation,sissy-ass,femeboy-anal

HD

Naughty Femboy Carli Rides Thick Dildo In Backdoor Delight

01:23 0 Views 66%

shemale,big-ass,sissy-training,lingerie-sexy,gymnastics-sex

HD

Flexible Booty Bounce With Sandra Zanerri In Gymnastics.

02:42 0 Views 64%

latina,transsexual,sissy,femboy,long-hair

HD

Slippery Slope: Insatiable Verification Vixens Get Naughty

00:13 0 Views 96%

blonde,interracial,amateur,wife,humiliation,camgirl,cuckold,sissy,black-dick,black-cock,phat-ass,faggot,pussy-boy,interracial-sex,thick-thighs,pawg-bbc,bbc-wife,bbc-worship,milf-pawg,hotwife-cuck

HD

Massive Ebony Cock Pounds Sara's Tight Holes In Every Possible Way!

01:03 0 Views 92%

blowjob,doggystyle,mature,threesome,fetish,cougar,cuckold,husband,old-young,cock-play,bisexual-cuckold,bi-cuckold,bi-threesome,old-cuckold,bi-cock-sucking,threesome-fmm,bi-ass-licking,bi-rimming,fat-senior

HD

Vintage Sissy Watches Russian Bombshell Get Pounded

09:09 276 Views 73%

anal,cumshot,dildo,blonde,vibrator,tranny,shemale,fisting,orgasm,cum-swallow,caged,sissy,cum-drinking,femboy,horse-cock,giant-dildo,huge-load,chastity-cage,multiple-orgasm,jessica-bloom

HD

Jessica Bloom Gets Frisky With Neighbor Neotori Jorhan (XL Edition)

10:10 85 Views 71%

anal,dildo,masturbation,training,big-cock,sissy,bbc,anal-sex,big-black-cock,gay-anal,shane-diesel,sissy-training

HD

Pervy Chatting As I Fill My Manhole

02:18 23 Views 96%

cumshot,cum,teen,cock,high-heels,boots,masturbation,lingerie,tranny,shemale,fetish,cute,trans,crossdresser,sissy,sneakers,femboy,cum-on-feet,heels-fetish

HD

Femboy Shoe Try-On Session Leads To Hot Solo Action!

05:03 499 Views 95%

anal,cumshot,dildo,ass,gaping,blowjob,wet,masturbation,gape,tranny,shemale,fetish,shower,pissing,trans,piss,farting,sloppy,sissy,anal-sex

HD

Latex-Clad Sissy Femboy Gets Wet And Wild In Shower: Pissing, Dildo Play, And Cock Sucking Galore!

05:02 0 Views 61%

anal,dildo,amateur,training,sissy,bbc,black-cock,big-black-cock,gay-anal,shane-diesel,sissy-training

HD

BBC Bonanza: Big Black Cock Reigns Supreme!

01:55 535 Views 79%

anal,stockings,cumshot,cum,sexy,gaping,wet,toys,masturbation,lingerie,gape,tranny,shemale,trans,messy,feet,sloppy,sissy,sex-toys,femboy

HD

Femboy's Naughty Anal Bead Adventure: Slimy & Juicy Fun!

05:02 0 Views 83%

anal,dildo,amateur,solo,training,big-cock,sissy,bbc,black-cock,gay-anal,shane-diesel,sissy-training

HD

Pounded Hard And Spoken To With Filthy Desires: Let's Get Stuffed Again, Baby!

01:15 0 Views 79%

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%

anal,cumshot,cum,dildo,latex,corset,gloves

HD

Jasmine's Sissy Delight With Black Pink Ecstasy

00:32 276 Views 70%

sissy,crossdressing,ballbusting

HD

Spanked, Smacked, And Ball-Busted: The Sequel To Punishing My Sissy Crossdresser

03:26 37 Views 77%

It never hurts to see what other fans of LetMeJerk are looking for

Discover a premium selection of Lazy Sissy 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 Lazy Sissy also check out: Sissy, Anal, Amateur, Tranny, Femdom.

With over 5,271 unique Lazy Sissy 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 100% of our Lazy Sissy collection is available in HD for your viewing pleasure.

We update our Lazy Sissy 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!