Insertion Shemale Videos

TrannyOne

Inserting a new huge dildo -part2

Categories: amateur, anal, gaping hole, hd, insertion, lingerie, masturbation, solo, toys, underwear

aShemaleTube

french porn ladyboy anal objects insertion

Categories: amateur, anal, french, insertion, ladyboy

TrannyOne

Black slut mega throat cocksucking collection

Categories: cougar, ebony, extreme, facial, granny, hairy, old, orgasm, passionate, throat

Pornstars: Heidi Waters

ShemaleZ

Brian Bonds And Angelina Trans - Trans Angelina Please In A Hardcore Double Insertion Act!

Categories: anal, ass, assfucking, bdsm, big cock, big tits, deep throat, dick, domination, hardcore

KeekAss

Sissy tart deep ass-fuck instructing for enormous schlongs

Categories: amateur, anal, assfucking, crossdressing, hd, masturbation, sissy, slut, solo, toys

aShemaleTube

TRANSEROTICA Restrained Guy Fisted Hard By Cute Shemale

Categories: anal, big cock, bondage, cute, dildo, fetish, fisting, gaping hole, handjob, hd

FlyFlv

Gaped Asshole And A Hard Tranny Dick

Categories: anal, ass, babe, blonde, dick, lingerie, masturbation, solo, tranny, transsexual

TrannyOne

Amateur Homemade Swinger DP Gangbang Double Penetration Anal Compilation

Categories: amateur, anal, ass, big cock, big tits, blowjob, cum, cumshot, fetish, hairy

KeekAss

TRANSEROTICA Confined Stud Fisted Rock-hard By Super-cute She-male

Categories: anal, big cock, blonde, bondage, brunette, cute, dildo, fetish, fisting, gaping hole

VideoSection

Mature anal, big ass anal

Categories: anal, ass, big ass, ebony, insertion, mature

ShemaleMovie

Extreme sound insertion and intense ass play with bad dragon and wine bottle, watch me stretch it out for you

Categories: american, anal, anal toying, ass, bottle, british, dildo, extreme, gaping hole, hardcore

aShemaleTube

Her wide ass hole is perfect for insertions

Categories: ass, insertion

aShemaleTube

Naked guy gets shemales dick insertions

Categories: dick, insertion, nude

aShemaleTube

Homemade object insertion

Categories: homevideo, insertion

TrannyOne

Huge Anus and Ass Stretching Toys In Crotchless Panties and Stockings

Categories: amateur, anal, anal fisting, anal toying, anus, ass, buttplug, gaping hole, insertion, stockings

KeekAss

Ryu Nymph Learns how to Have Fun Baseball with her Booty

Categories: amateur, anal, booty, cum, cumshot, extreme, gaping hole, hd, insertion, masturbation

KeekAss

Brandynette Brainwash Joy Button Dressup - Why Bambi ruins your expectations!

Categories: amateur, anal, crossdressing, hd, homevideo, lingerie, model, small tits, stockings, toys

Pornstars: Anita Blue

KeekAss

gordita culona transexual con inserción anal invasion de manage de playstation en el bum

Categories: amateur, anal, ass, assfucking, brunette, crossdressing, handjob, hardcore, hd, homevideo

TrannyOne

The first challenge of inserting a new huge dildo

Categories: anal, anus, ass, booty, dildo, hd, insertion, lingerie, masturbation, mature

ShemaleMovie

Cd solo masturbation, cd lingerie

Categories: amateur, anal, big cock, insertion, lingerie, masturbation, solo, spanish, teen (18+)

aShemaleTube

Webcam Butt Plug Insertion

Categories: amateur, big cock, buttplug, crossdressing, hd, insertion, lingerie, pantyhose, toys, webcam

KeekAss

Mature Sissy fuckslut Faux-Cock Bi-Atch

Categories: anal, ass, big ass, bisexual, corset, crossdressing, dick, gagging, insertion, small cock

KeekAss

Transgirl Urinate Fuck Hole Urethral Injection

Categories: crossdressing, fetish, handjob, hardcore, hd, jerking, masturbation, solo, tgirl, toys

aShemaleTube

ass destroyed but happy

Categories: ass, crossdressing, dildo, gaping hole, hd, insertion, latina, orgasm, solo, toys

aShemaleTube

Big ass playing with new baloon toy

Categories: amateur, anal, ass, balloon, big ass, crossdressing, fisting, sissy, solo, toys

KeekAss

Guitarse Hero : Hankey's Trip !

Categories: amateur, anal, anal toying, big ass, crossdressing, dildo, hd, homevideo, masturbation, small tits

TrannyOne

Shemale Nest

Categories: anal, anus, ass, big cock, big tits, blowjob, cum, cumshot, dick, doggystyle

ShemaleMovie

Obese FTM gamer plays solo with himself on the couch

Categories: amateur, bbw, bedroom, chubby, couch, dildo, fingering, game, insertion, masturbation

MyLust

BBC Breeds FTM Bottom Ari Koyote Bareback

Categories: barebacking, big black cock, big cock, black, blowjob, cumshot, deep throat, ebony, fetish, gagging

FetishPapa

Lingerie shemale Natalie Mars urethra insertion masturbation intensely in solo play

Categories: big cock, cumshot, hd, insertion, lingerie, masturbation, pornstar, solo, stockings, urethra

Txxx

Alexia Rios in Slow Insertion - DreamTranny

Categories: big tits, fantasy, insertion, latina, masturbation, solo, toys

aShemaleTube

Bottle and other insertions

Categories: anal, ass, bottle, crossdressing, gaping hole, hd, insertion, mature

ShemaleMovie

Compilation of intense anal stretching with gaping holes

Categories: amateur, anal, anal toying, ass, big ass, compilation, dildo, gaping hole, insertion, riding

KeekAss

Extraordinary buttfuck fake penis joy with Lucy Essex CD

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JizzBunker

Shemale Erica Lee inserting a banana

Categories: banana, insertion, latina, masturbation, pornstar

Pornstars: Erica Lee

ShemaleMovie

Enormous vibrator sliding deep into my large rear end

Categories: amateur, american, anal, anal toying, ass, big ass, big cock, crossdressing, dildo, huge cock

ShemaleMovie

Shemale enjoying anal with enormous plaything

Categories: anal, anal toying, ass, dildo, gaping hole, insertion, masturbation, pantyhose, riding, sissy

JizzBunker

Urethra fucking trans in solo fetish

Categories: amateur, anal, bdsm, bondage, deep throat, fetish, fisting, gaping hole, hardcore, insertion

aShemaleTube

JuliaCool Pantyhose Penetration Dildo Insertion

Categories: dildo, insertion, pantyhose

aShemaleTube

Anal Snack

Categories: amateur, anal, ass, fetish, food, gaping hole, hd, insertion, masturbation, model

aShemaleTube

Pregnant Sissy (Pt 2)

Categories: amateur, anal, asian, femboy, fetish, huge dildo, insertion, sissy, small cock, toys

aShemaleTube

Bubble butt shemale bent over for BBC insertion

Categories: anal, ass, bend over, big ass, big black cock, booty, fetish, hd, insertion, tgirl

aShemaleTube

Gyno examination for CD

Categories: anal, anal toying, ass, crossdressing, dildo, examination, gynecologist, hd, insertion, latex

aShemaleTube

Sissy Kenzie Star fucks her horny little ass

Categories: anal, ass, extreme, gaping hole, hd, insertion, sissy, toys

TrannyOne

Aimee Hot MILF - Vegetables in the cunt and the whole face in the sperm of her beloved husband!

Categories: amateur, big tits, bitch, blowjob, brutal, close up, cum, cunt, dick, dildo

TrannyOne

Depraved MILF has wild convulsions riding on man's fist

Categories: blowjob, brutal, couple, extreme, fisting, hardcore, hd, insertion, mature, milf

TrannyOne

Mini wand insertion edging

Categories: amateur, anal, anus, ass, australian, big cock, booty, dick, edging, hd

TrannyOne

Big cock tranny piss with cum swallow

Categories: anal, big cock, cum, cum swallowing, insertion, pissing, tranny, transsexual

ShemaleMovie

Raven is the thickest babe craving big cock

Categories: anal, babe, big cock, dildo, extreme, gaping hole, insertion, tattoo, toys

VideoSection

Big anal toys and ball play for some extreme fun

Categories: anal, anal toying, bisexual, close up, cum, extreme, funny, gaping hole, insertion, jizz

aShemaleTube

Isabella Latex Brush Fucking

Categories: amateur, anal, big ass, cumshot, extreme, hd, insertion, kinky, latex, masturbation

HDSex

Kenzie Star's wild anal adventure with a massive toy and a sissy twist

Categories: anal, ass, extreme, gaping hole, insertion, sissy, toys, wild

KeekAss

Stunning Shemale Plays Solo

Categories: amateur, ass, beauty, crossdressing, cute, extreme, homevideo, insertion, latex, masturbation

JizzBunker

Giant Anal Plug Fully Inserted 20m

Categories: anal, insertion

ShemaleMovie

Shemale riding dildo, sissy crossdresser

Categories: anal, anal toying, ass, bathroom, crossdressing, dildo, fishnet, fisting, gaping hole, huge dildo

aShemaleTube

Big insertions for blonde slut

Categories: amateur, anal, blonde, crossdressing, hd, insertion, mature, slut

TrannyOne

Two Gays Fuck Nice Shemale

Categories: anal, anus, ass, big cock, big tits, bisexual, black, blowjob, compilation, cum

JizzBunker

Inserting toy to the base

Categories: anal, big ass, hardcore, insertion, masturbation, solo, teen (18+), toys, webcam

KeekAss

Leeked movie of catapulting a leek in a cavity with no pickle

Categories: amateur, anal, ass, bedroom, big ass, condom, cum, dress, hd, insertion

HDSex

Kinky individual in stockings enjoys urethra play, masturbation, and orgasm

Categories: amateur, bdsm, femboy, handjob, hardcore, homevideo, insertion, kinky, masturbation, orgasm

ShemaleMovie

Unusual solo fisting session with anal dildo play and busty babe in nylon stockings

Categories: anal, anal toying, ass, babe, big tits, bizarre, crossdressing, dildo, fisting, gaping hole

JizzBunker

Black shemale beauty inserts sex toy in tight anal and jerks

Categories: anal, beauty, big cock, black, hardcore, insertion, lingerie, masturbation, tight, toys

KeekAss

Glass Faux-cock in Peehole

Categories: amateur, big clit, dick, dildo, hd, insertion, masturbation, piercing, pissing, pussy

JizzBunker

Trans insertion play treatment

Categories: amateur, anal, bdsm, bondage, deep throat, fetish, fisting, gaping hole, hardcore, insertion

aShemaleTube

sissy crossdresser huge toy insertions and fisting

Categories: amateur, anal, crossdressing, femboy, fisting, hd, huge dildo, insertion, sissy, solo

aShemaleTube

Toying time

Categories: anal, ass, crossdressing, dildo, hd, insertion, mature, toys

aShemaleTube

TS Jonelle Brooks strokes cock hard after anal insertion

Categories: anal, big cock, big tits, dick, fetish, hd, insertion, masturbation, solo, tgirl

aShemaleTube

Bottle play

Categories: anal, ass, bottle, crossdressing, hd, insertion

TrannyOne

This tranny needs immediate anal insertions!

Categories: amateur, anal, blonde, dick, insertion, tranny, transsexual, vintage

aShemaleTube

Sexy Xhica Tranny Stuffs Her Big Toy

Categories: amateur, big cock, big tits, hd, homevideo, insertion, latina, lingerie, teen (18+), toys

TrannyOne

German Movie Schnick Schnack Schnuck

Categories: amateur, anal, anus, asian, ass, bbw, big cock, big tits, bisexual, black

TrannyOne

bitch wife sharing dick with teenager chick

Categories: 3some, amateur, ass, bbw, big tits, bisexual, bitch, blowjob, chubby, cougar

aShemaleTube

crossdresser beer bottle anal insertion

Categories: anal, bottle, crossdressing, insertion, transvestite

TrannyOne

Shayane Lima Curvatious Shemale Solo Jerking

Categories: ass, beauty, big tits, dick, dildo, gorgeous, insertion, jerking, kinky, ladyboy

KeekAss

Zuccini sissy in innocence

Categories: amateur, anal, anal toying, cage, crossdressing, cute, femboy, feminization, fetish, hardcore

TrannyOne

TS Nikki Vicious plays some toys in her ass

Categories: anal, ass, big cock, big tits, blonde, blowjob, hardcore, hd, insertion, pornstar

Pornstars: Mercedes Carrera

ShemaleZ

Messy Ass Training Session Ts Insertion Gape Training

Categories: amateur, ass, big ass, brazilian, brunette, gaping hole, hd, insertion, latina, messy

VideoSection

Olivia experiments with an anal plug for the first time in my ass to embrace her inner sissy

Categories: anal, anal toying, ass, beauty, big ass, crossdressing, femboy, first time, insertion, sissy

KeekAss

Bashful Racoon is having joy outdoor

Categories: amateur, bdsm, bicycle, close up, dick, feminization, fetish, gay, hd, insertion

KeekAss

尿道口をグリグリしてドライオーガズムでイッちゃう。The urethral opening is agitated and she blows a load with a dry climax.

Categories: amateur, asian, big ass, cosplay, fetish, hd, insertion, japanese, masturbation, orgasm

XXXDan

Oviposition is not only about laying eggs

Categories: amateur, anal, dildo, fetish, insertion, masturbation, russian, small tits, solo, toys

XXXDan

Crossdresser playing anal with vegetables and pee herself

Categories: amateur, anal, big ass, big cock, blonde, crossdressing, european, fetish, insertion, lingerie

JizzBunker

She cums after inserting just one finger in her ass

Categories: ass, big ass, cum, fingering, insertion

ShemaleMovie

Larissa1sexdoll finds pleasure in the forest: self-fisting, huge dildo, and 1.5 liter bottle play

Categories: anal, ass, bottle, dildo, fisting, forest, gaping hole, huge dildo, insertion, outdoor

JizzBunker

Trans dominatrix whipping and flogging

Categories: amateur, bdsm, bondage, dominatrix, fetish, insertion, latex, slut, transsexual, whip

aShemaleTube

Ts Isabella kinky October 2025

Categories: amateur, anal, cumshot, dildo, extreme, femboy, fetish, hd, insertion, kinky

XXXDan

Mouthgagged trans drowls in kinky BDSM

Categories: amateur, bdsm, bondage, fetish, gagging, insertion, kinky, latex, solo, transsexual

KeekAss

Deep Sounding Her Encaged Clitoris Till She Blows a load 4K

Categories: amateur, cage, clit, creampie, cum, cumshot, hardcore, hd, insertion, massage

aShemaleTube

Insane huge dildo - Part 34 (Full deep inside)

Categories: amateur, ass, femboy, fetish, gaping hole, homevideo, huge dildo, insertion, small cock, toys

aShemaleTube

Submissive tranny ass stretched roughly with anal insertions

Categories: anal, ass, dildo, hd, insertion, natural tits, submissive, tgirl, toys, tranny

aShemaleTube

extreme sissy training: boy becoming to girl

Categories: 3some, amateur, anal, big cock, boy, domination, extreme, fetish, fisting, insertion

aShemaleTube

Wet dildoed ass

Categories: anal, anal toying, ass, crossdressing, dildo, hd, insertion, toys, wet

aShemaleTube

Anal toys testing

Categories: anal, anal toying, ass, balls, crossdressing, dildo, hd, high heels, insertion, mature

aShemaleTube

Double dildo for two trannies

Categories: anal, anal toying, ass, dildo, double penetration, insertion, lesbian, toys, tranny, transsexual

TrannyOne

Penis Sounding, peehole, boots, pantyhose

Categories: big cock, boots, crossdressing, cum, czech, dick, european, feet, fetish, gay

KeekAss

TranssexualNetwork.com - Natalie Mars' urethra insertion and masturbation in lingerie

Categories: big cock, cumshot, glasses, insertion, lingerie, masturbation, pornstar, stockings, tgirl, tranny

TrannyOne

Redhead tranny Shiri Allwood inserting sounding rod

Categories: anal toying, ass, buttplug, fetish, fingering, hd, insertion, masturbation, nipples, puffy nipples

TrannyOne

!Molodaya lyubit seks osobenno v popu

Categories: amateur, anal, anus, asian, ass, bbw, bdsm, big cock, big tits, bisexual

XXXDan

Bell4lat1n4 Inserting vibrator inside ass

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TrannyOne

Pegging crossdresser bisexual cuckold bi husband with cum swap and cumkiss

Categories: amateur, anal, anus, ass, assfingering, assfucking, big tits, bisexual, blowjob, creampie

aShemaleTube

Fist an big insertion

Categories: anal, big ass, domination, french, hd, insertion, pov, spandex, toys

aShemaleTube

Strawberry Anal Smoothie

Categories: amateur, anal, femboy, fetish, food, hd, homevideo, insertion, outdoor, sissy

HDSex

She craves a massive cock in her ass from Gaurav the weirdo

Categories: anal, anal toying, ass, big cock, brutal, crossdressing, cum, cumshot, femboy, gaping hole

Txxx

Lingerie TS with big boobs enjoys anal and object insertion

Categories: anal, barebacking, big tits, cumshot, insertion, lingerie, stockings, transsexual

aShemaleTube

Very long anal toy insertion

Categories: amateur, anal, anal toying, big tits, crossdressing, hd, homevideo, insertion, mature, small cock

ShemaleMovie

Deep anal dildo, anal insertion

Categories: anal, anal toying, ass, crossdressing, dildo, insertion, masturbation, solo, toys

ShemaleMovie

Fucking fruit, cute femboy anal

Categories: anal, ass, beauty, cute, femboy, insertion

aShemaleTube

Webcam Insertion Banana cream Ass Exstrem Anal Shemales

Categories: amateur, anal, ass, banana, compilation, creampie, crossdressing, insertion, stockings, webcam

XXXDan

Leashed Slave Natalie Mars Extreme Anal Squirt Gaping Insertions - TranssexualAngel

Categories: anal, bdsm, blowjob, bondage, deep throat, extreme, gaping hole, hardcore, insertion, pissing

KeekAss

Tranny with little tits embeds a shaft in her dick and wanks

Categories: big cock, cumshot, dick, fishnet, handjob, hd, insertion, masturbation, natural tits, solo

XXXDan

Urethra fucks trans in solo fetish

Categories: amateur, anal, bdsm, bondage, deep throat, fetish, fisting, gaping hole, hardcore, insertion

TrannyOne

Cum-and-pee Drink For a Sexy Tranny With a Fisted And Zucchini-stretched Anus

Categories: amateur, anal, anus, assfingering, assfucking, cum, fishnet, fisting, gaping hole, hd

aShemaleTube

filipina shemale pink outfit log insertions

Categories: filipina, insertion

aShemaleTube

Insane huge dildo - Part 25

Categories: amateur, anal, big ass, crossdressing, domination, fetish, gaping hole, hd, huge dildo, insertion

aShemaleTube

Sissy insert tampon

Categories: anal, hd, insertion, sissy

aShemaleTube

TS Tyra Scott spreading legs for huge cock insertion

Categories: anal, blowjob, facial, hd, huge cock, insertion, legs, pornstar, spreading, tgirl

aShemaleTube

Anal insertions

Categories: anal, ass, crossdressing, dildo, hd, insertion, mature, toys

aShemaleTube

Trans girl gets her favorite toy

Categories: amateur, big cock, big tits, hd, homevideo, insertion, lingerie, masturbation, solo, toys

TrannyOne

Thick Latina rides

Categories: amateur, anal, anus, asian, ass, bbw, big cock, big tits, bisexual, black

XXXDan

Deep anal fisting my boy toy with MILF Lisa and TGirl Charlotte

Categories: 3some, amateur, anal, anal fisting, blonde, boy, british, femdom, fisting, gloves