Related:irish femboy first time young crossdresser sissy sissy trainer painal huge cock huge cock bareback teen

Search results - Sissy First Time

Total found: 108 videos

The best way to become a sissy boi is jerk off with a sissy10:11
3 years ago xHamster

The best way to become a sissy boi is jerk off with a sissy

Amateur Bear Crossdresser Daddy Domination Emo Fat First time Hd
First time sissy takes dildo1:15
8 years ago xHamster

First time sissy takes dildo

Amateur Asian Dildo First time Hd Sissy
Sissy Crossdressers First Time Anal3:18
7 years ago xHamster

Sissy Crossdressers First Time Anal

Amateur Anal Bareback Blowjob Crossdresser First time Sissy Small cock
This is my first time as a crossdressing sissy15:02
7 years ago xHamster

This is my first time as a crossdressing sissy

Amateur Crossdresser First time Hd Hunk Masturbation Sissy
Sissy Schwuchtel Arschfick Vorfuehrung2:32
5 years ago xHamster

Sissy Schwuchtel Arschfick Vorfuehrung

Amateur Anal Bareback Bdsm Crossdresser First time Hd Sissy
German Amateur Sissy CD gets her first Fuck1:06
5 years ago xHamster

German Amateur Sissy CD gets her first Fuck

Amateur Anal Crossdresser First time Hd Sissy
Me playing with my sissy ass0:48
4 years ago xHamster

Me playing with my sissy ass

Amateur Anal Ass Crossdresser Dildo First time Hd Hunk Massage
My Sissy ass in panties1:01
4 years ago xHamster

My Sissy ass in panties

Amateur Anal Ass Big cock Crossdresser First time Hd Masturbation Pantyhose
This is my first time dressing like a sissy17:09
4 years ago xHamster

This is my first time dressing like a sissy

Amateur Crossdresser First time Hd Latino Masturbation Sissy
Sissy first time 7 inch Dildo1:47
4 years ago xHamster

Sissy first time 7 inch Dildo

Amateur Anal Crossdresser Dildo First time Hd Sissy Twinks
sissy Giouli Teasing0:15
4 years ago xHamster

Sissy Giouli Teasing

Amateur Big ass Chubby Crossdresser Daddy First time Greek Latino Sissy
First time my sissy pussy was fucked0:31
4 years ago xHamster

First time my sissy pussy was fucked

Anal Crossdresser First time Hd Sissy
Pump my sissy crossdresser ass full of cum13:12
4 years ago xHamster

Pump my sissy crossdresser ass full of cum

Ass Big cock Crossdresser First time Hd Hunk Masturbation Sissy
Dressing like a sissy for the first time got me so hard17:27
4 years ago xHamster

Dressing like a sissy for the first time got me so hard

Crossdresser First time Hd Hunk Latino Masturbation Sissy
Sissy Bi Curious First Time Ruined Orgasm0:47
4 years ago xHamster

Sissy Bi Curious First Time Ruined Orgasm

Amateur Big cock British Crossdresser First time Handjob Hd Masturbation Orgasm
HOT CD TRAP SISSY OUTDOORS0:11
4 years ago xHamster

HOT CD TRAP SISSY OUTDOORS

Amateur Anal Ass Bareback Crossdresser Daddy First time Interracial Outdoor
Sissy Painful Double Penetration with 2 Cucumbers2:12
4 years ago xHamster

Sissy Painful Double Penetration with 2 Cucumbers

Amateur Anal Big cock British Crossdresser Double penetration First time Gaping Hd
I fuck the sissy elf in a tight point and powerfully finish4:59
4 years ago xHamster

I fuck the sissy elf in a tight point and powerfully finish

Anal Bareback Big cock Bukkake Crossdresser Emo First time Hd Hunk
Sissy crossdresser Trying out the ass on my new Toy with mus16:01
4 years ago xHamster

Sissy crossdresser Trying out the ass on my new Toy with mus

Amateur American Anal Ass Crossdresser First time Hd Masturbation Sissy
Sissy Crossdresser Slut fucked for first time1:00
4 years ago xHamster

Sissy Crossdresser Slut fucked for first time

American Anal Bdsm Crossdresser Daddy First time Hd Humiliation Sissy
sissy slut sucking her first cock0:09
4 years ago xHamster

Sissy slut sucking her first cock

Amateur Blowjob Couple Daddy First time Sissy Small cock Sucking
I suck sissy femboy's huge cock !2:28
4 years ago xHamster

I suck sissy femboy's huge cock !

Amateur Big cock Blowjob Cumshot Daddy Emo First time Hd Homemade
Sissy in Chasity with finger in my ass0:18
4 years ago xHamster

Sissy in Chasity with finger in my ass

Amateur Anal Crossdresser First time Hd Masturbation Sissy
Your first time as a sissy will be amazing16:28
4 years ago xHamster

Your first time as a sissy will be amazing

Amateur Ass Big cock Crossdresser Dick First time Hd Hunk Latino
SluttyAmanda Caged Beta Sissy Public Exposure Walk Downtown0:43
4 years ago xHamster

SluttyAmanda Caged Beta Sissy Public Exposure Walk Downtown

Amateur Black Crossdresser First time Hd Outdoor Public Sissy
Mesmerizing you to go Gay as you Repeat the Sissy Mantra wit3:05
3 years ago xHamster

Mesmerizing you to go Gay as you Repeat the Sissy Mantra wit

Amateur Crossdresser Emo First time Hd Homemade Masturbation Sissy Skinny
Exposed at Camp Sissy Boi Small penis humiliation9:32
3 years ago xHamster

Exposed at Camp Sissy Boi Small penis humiliation

Amateur Crossdresser Daddy Domination Emo Fat Femdom First time Hd
The horny sissy boi cums twice so HOTT15:00
3 years ago xHamster

The horny sissy boi cums twice so HOTT

Amateur Bdsm Bear Crossdresser Daddy Emo Fat First time Hd
Silly gay sissy boi puts his purple toy in his butt hole6:55
3 years ago xHamster

Silly gay sissy boi puts his purple toy in his butt hole

Amateur Ass Big cock Crossdresser Daddy Emo Fat First time Hd
My first time as a sissy feels so right17:55
3 years ago xHamster

My first time as a sissy feels so right

Amateur Ass Big cock Crossdresser Dick First time Hd Hunk Latino
Caged sissy riding a dildo3:04
3 years ago xHamster

Caged sissy riding a dildo

Amateur Anal Dildo First time French Hd Massage Masturbation Sissy
Sissy sucking and working his hole3:23
3 years ago xHamster

Sissy sucking and working his hole

Anal Big cock Blowjob Emo First time Hd Hunk Monster Sissy
The Sissy Algorithm4:03
3 years ago xHamster

The Sissy Algorithm

Amateur Blowjob Crossdresser Dildo Domination Emo First time Hd Masturbation
Sissy Guide Step 3 Graduate and Squirt Eat the Cummies3:21
3 years ago xHamster

Sissy Guide Step 3 Graduate and Squirt Eat the Cummies

Amateur Blowjob Domination Emo First time Hd Masturbation Old man Sissy
JOI with my cute and sexy sissy bear3:26
3 years ago xHamster

JOI with my cute and sexy sissy bear

Amateur Bdsm Bear Crossdresser Daddy Emo First time Hd Masturbation
Sissy boy first time NEW EXPLOSIVE vibrator0:40
3 years ago xHamster

Sissy boy first time NEW EXPLOSIVE vibrator

Amateur Anal Compilation Crossdresser Cumshot First time Hd Massage Orgasm
Timid French sissy first-ever time to fellate5:52
4 years ago Gay Ck

Timid French sissy first-ever time to fellate

Blowjob Cumshot Dick First time French Handjob Hd Shy Sissy
Sissy dude juices pied hatch Grinder fashion5:23
3 years ago Gay Ck

Sissy dude juices pied hatch Grinder fashion

Anal Bareback Bbc Big cock Black Black cock Blowjob Cheating Creampie
Bashful French sissy first-ever time to gargle5:52
4 years ago Gay Ck

Bashful French sissy first-ever time to gargle

Amateur Blowjob Crossdresser Cumshot Dick Fetish First time French Hairy
Bony Teenager Sissy Opening Up her Pink Hole with Large Donk Butt-Plug5:58
5 years ago Gay Ck

Bony Teenager Sissy Opening Up her Pink Hole with Large Donk Butt-Plug

Anal Butt Creampie Dildo Farting Fetish First time Fisting Gaping
THE SWITCH UP- use Fuck Stick for second Time Ever... might be Turning Sissy10:03
4 years ago Gay Ck

THE SWITCH UP- use Fuck Stick for second Time Ever... might be Turning Sissy

Anal Blowjob Cumshot Dick First time Handjob Sissy Solo Toys
Sissy first time in chasity playing with ass3:55
3 years ago xHamster

Sissy first time in chasity playing with ass

Amateur Anal Ass Big ass Black Crossdresser Dildo First time Gaping
Playing with my sissy ass with a vibrator5:28
3 years ago xHamster

Playing with my sissy ass with a vibrator

Amateur Anal Asian Ass Crossdresser First time Hd Indian Orgasm
Young CD with Limp Sissy Clitty Hands free orgasm12:13
3 years ago xHamster

Young CD with Limp Sissy Clitty Hands free orgasm

Amateur Anal Asian Ass Crossdresser First time Hd Indian Masturbation
DICKS MAKE YOU HORNY THE SISSY SONG FOR GAY BOIS7:41
3 years ago xHamster

DICKS MAKE YOU HORNY THE SISSY SONG FOR GAY BOIS

Amateur Bdsm Beach Crossdresser Emo First time Hd Homemade Jerking
Cheekyrider4u 14 inch big black dildo fucking thick sissy jock with sex machine rainbow star on sweet peach sexy gape8:15
3 years ago xHamster

Cheekyrider4u 14 inch big black dildo fucking thick sissy jock with sex machine rainbow star on sweet peach sexy gape

Amateur American Anal Bareback Big cock Bisexual Black Black cock Chubby
Sissy pussy is all body in cum ! Rivers of sperm!7:56
3 years ago xHamster

Sissy pussy is all body in cum ! Rivers of sperm!

Amateur Big cock Blowjob Bukkake Crossdresser Cumshot Daddy Dick Emo
Sissy Ass Fucking Farts Gape Have Fun3:43
3 years ago Gay Ck

Sissy Ass Fucking Farts Gape Have Fun

Anal Cumshot Dick Farting First time Hairy Handjob Hd Sissy
Sissy Boy Toy Round Ass Hot Anal7:08
2 years ago xHamster

Sissy Boy Toy Round Ass Hot Anal

Amateur Anal Ass Big ass Crossdresser European First time Gaping Hd
My first time dressed as a sissy feels incredible15:47
2 years ago xHamster

My first time dressed as a sissy feels incredible

Amateur Ass Crossdresser First time Hd Sissy Skinny Twinks
femboy smashes herself and pops abundantly from it. point of view. tgil. sissy. she-creature3:48
2 years ago Gay Ck

Femboy smashes herself and pops abundantly from it. point of view. tgil. sissy. she-creature

69 Anal Cumshot Dick Femdom First time Hairy Handjob Hd
Straight Sissy Crossdresser Big Butt White Big Ass Just Like To Be Very Beauty and Cute Candy Cosplayer Girl Lover MTF4:03
2 years ago xHamster

Straight Sissy Crossdresser Big Butt White Big Ass Just Like To Be Very Beauty and Cute Candy Cosplayer Girl Lover MTF

Amateur American Anal Blowjob College Crossdresser European First time Hd
Amateur sissy first time riding her dildo4:11
2 years ago xHamster

Amateur sissy first time riding her dildo

Amateur Anal British Crossdresser Dildo First time Hd Sissy Skinny
First Time Sissy Slut WEBCam Show17:22
2 years ago xHamster

First Time Sissy Slut WEBCam Show

Amateur Bisexual Condom Crossdresser Cumshot First time Handjob Hd Lingerie
Hard daddy fucks a young twinkie sissy and pours cum in the ass!6:36
2 years ago xHamster

Hard daddy fucks a young twinkie sissy and pours cum in the ass!

Amateur Anal Bareback Big cock Boyfriend Bukkake College Crossdresser Cumshot
Cruise Daddy and Sissy with big dicks and fountains of cum!30:48
2 years ago xHamster

Cruise Daddy and Sissy with big dicks and fountains of cum!

Amateur Bareback Bear Big cock College Crossdresser Cumshot Daddies Daddy
Limp Sissy Clitty1:21
2 years ago xHamster

Limp Sissy Clitty

Amateur American Anal Crossdresser Dildo First time Hd Masturbation Sissy
my first becoming a sissy bitch video featuring me, Mark Moran0:47
2 years ago xHamster

My first becoming a sissy bitch video featuring me, Mark Moran

Amateur Crossdresser Dildo Fat First time Grandpa Hd Humiliation Reality
Sequel to Pegging of Sissy Slut for the First Time30:11
2 years ago xHamster

Sequel to Pegging of Sissy Slut for the First Time

Amateur Condom Crossdresser Cumshot European Fetish First time Handjob Hd
sissy with lubed up ass31:03
2 years ago xHamster

Sissy with lubed up ass

Amateur Anal Ass Crossdresser Daddies Daddy Dildo European First time
sissy fag trav dressing up in underwear and inserting large dildos and plugs9:07
2 years ago xHamster

Sissy fag trav dressing up in underwear and inserting large dildos and plugs

Amateur Anal Ass Crossdresser Daddy Dress European First time Fisting
Sissy fagot with open asshole, inserts plug and stainless steel bowls25:50
2 years ago xHamster

Sissy fagot with open asshole, inserts plug and stainless steel bowls

Amateur Anal Ass Balls Butt Crossdresser Daddy Dildo European
Alpha Male Femboy Sissy (M4M Gay Audio Story)6:00
2 years ago xHamster

Alpha Male Femboy Sissy (M4M Gay Audio Story)

Amateur American Anal Bdsm Big cock Blowjob Crossdresser Cute Feet
pretty sissy gets her pussy fuced34:17
2 years ago GayGo.tv

Pretty sissy gets her pussy fuced

Amateur Blowjob Domination First time Group Homemade Massage Mature Muscle
Sissy slut takes dildo0:31
2 years ago xHamster

Sissy slut takes dildo

British Dildo First time Hd Masturbation Sissy Solo
Sissy gets sloppy deeptgroating 9" cock balls deep2:27
2 years ago xHamster

Sissy gets sloppy deeptgroating 9" cock balls deep

Amateur American Balls Big cock Blowjob Caught Crossdresser Deepthroat Dick
sissy femboy shows off outfit part 33:01
2 years ago xHamster

Sissy femboy shows off outfit part 3

Amateur American Anal Big ass Crossdresser First time Hd Latino Lingerie
Sissy Crossdresser Teases Bubble Butt0:45
2 years ago xHamster

Sissy Crossdresser Teases Bubble Butt

Amateur American Asian Ass Bareback Bitch Crossdresser Cute First time
Real Sissy crossdresser cuckold slut fucking multiple big dildos in chastity cage!15:50
1 year ago xHamster

Real Sissy crossdresser cuckold slut fucking multiple big dildos in chastity cage!

Amateur American Anal Ass Big ass Big cock Crossdresser Cuckold Cute
sissy for xhamster offers you her cum, ruined orgasm spermnet2:35
1 year ago xHamster

Sissy for xhamster offers you her cum, ruined orgasm spermnet

Cumshot Domination Femdom First time French Handjob Hd Humiliation Hunk
Sissy crossdresser self fisting5:26
1 year ago xHamster

Sissy crossdresser self fisting

Amateur Anal Crossdresser Fingering First time Fisting German Hd Lingerie
Sissy Dildo Ass Play1:22
1 year ago xHamster

Sissy Dildo Ass Play

Amateur American Anal Crossdresser First time Hd Latino Lingerie Sissy
Anal sissy slut1:47
1 year ago xHamster

Anal sissy slut

Anal Bareback Big cock Crossdresser Dildo First time Hd Homemade Lingerie
YOUNG SISSY PUSSY TRAINING1:58
1 year ago xHamster

YOUNG SISSY PUSSY TRAINING

Amateur Anal Crossdresser First time Hd Homemade Masturbation Reality Sissy
Asian sissy wear chastity to prepare locktober1:35
1 year ago xHamster

Asian sissy wear chastity to prepare locktober

Amateur Asian Bitch Crossdresser Fetish First time Hd Korean Masturbation
Self Fist - Self Fisting by Sissy1:41
1 year ago xHamster

Self Fist - Self Fisting by Sissy

Amateur Anal Ass Big ass Brazilian Closeup Creampie Crossdresser Fingering
Luciano fag, dressing like a sissy and inserting large plugs and dildos into the ass13:54
1 year ago xHamster

Luciano fag, dressing like a sissy and inserting large plugs and dildos into the ass

Amateur Anal Ass Big ass Butt Daddy Dildo Extreme First time
Small dick sissy rides dildo1:16
1 year ago xHamster

Small dick sissy rides dildo

American Dick Dildo Fetish First time Hd Homemade Riding Sissy
Sissy Chub Shaking Fat Ass in White Granny Panties2:50
1 year ago xHamster

Sissy Chub Shaking Fat Ass in White Granny Panties

American Ass Bbw Big ass Black Chubby Closeup Crossdresser Fat
Sexcapade fun: young gay sissy wants to make a quick movie7:17
1 year ago xHamster

Sexcapade fun: young gay sissy wants to make a quick movie

Amateur Anal Bareback Closeup College Creampie Cumshot Cute Fingering
Completely bald sissy cumslut sucking a dildo exposing his pathetically small cock5:40
1 year ago xHamster

Completely bald sissy cumslut sucking a dildo exposing his pathetically small cock

69 Amateur Ass Bareback Blowjob Couple Crossdresser Cum in mouth Cumshot
Sissy sucks on 21 cm dildo0:14
1 year ago xHamster

Sissy sucks on 21 cm dildo

Amateur Blowjob Dildo First time German Hd Homemade Masturbation Sissy
Sissy asian CD in sis lingerie6:26
1 year ago xHamster

Sissy asian CD in sis lingerie

Amateur Asian Crossdresser First time Hd Homemade Lingerie Pov Sissy
CD sissy asian whore with dirty lingerie0:39
1 year ago xHamster

CD sissy asian whore with dirty lingerie

Amateur First time Homemade Lingerie Pov Sissy Small cock
Sissy cumslut in panties and never sucked cock5:09
1 year ago xHamster

Sissy cumslut in panties and never sucked cock

69 Amateur Ass Bikini Blowjob Bukkake Crossdresser Cum in mouth Dildo
Chubby sissy panty try on in chastity6:54
1 year ago xHamster

Chubby sissy panty try on in chastity

Amateur American Anal Ass Bear Big ass Butt Chubby Crossdresser
Sissy Ass rimming and then getting fucked like a whore5:37
1 year ago xHamster

Sissy Ass rimming and then getting fucked like a whore

Amateur Anal Ass Big ass Big cock Black Blowjob Crossdresser Feet
sexy sissy whore is being anal fucked by daddy7:29
1 year ago xHamster

Sexy sissy whore is being anal fucked by daddy

Amateur Anal Bareback Bdsm Big cock Cheating Couple Crossdresser Cuckold
Sexy boy with sissy cd9:38
1 year ago xHamster

Sexy boy with sissy cd

Anal Bareback Crossdresser Daddy Fingering First time Hd Homemade Indian
Sissy 95:37
1 year ago xHamster

Sissy 9

Fingering First time Fisting Hd Indian Piercing Sissy Skinny Small cock
Sissy trying anal for the first time1:29
1 year ago xHamster

Sissy trying anal for the first time

Anal Asian Bathroom Fingering First time Gaping Hd Homemade Masturbation
Sissy convinces her neighborhood neighbor to let her enjoy his big male feet5:30
1 year ago xHamster

Sissy convinces her neighborhood neighbor to let her enjoy his big male feet

Amateur Blowjob Crossdresser Dick Domination Feet Fetish First time Foot fetish
Horny sissy blind fold fantasy16:48
1 year ago xHamster

Horny sissy blind fold fantasy

African Anal Bareback Big cock Blindfolded Blowjob Creampie Ebony Feet
Sissy's Neglige1:13
1 year ago xHamster

Sissy's Neglige

Bdsm European Fetish First time German Hd Homemade Lingerie Mature
Elax sissy boy sex toy handjob5:13
1 year ago xHamster

Elax sissy boy sex toy handjob

Amateur Anal Crossdresser Cute Dildo Fetish First time German Handjob
Kinky sissy's wild blindfolded fantasy16:50
1 year ago Gay Bingo

Kinky sissy's wild blindfolded fantasy

Bareback Big cock Creampie First time Missionary
Sissy maid amateur5:10
11 months ago xHamster

Sissy maid amateur

Amateur Crossdresser Fetish First time Hd Latino Maid Muscular Sissy
Sissy compilation5:26
11 months ago xHamster

Sissy compilation

Compilation Fetish First time Hd Masturbation Mature Muscular Solo Underwear
Sissy Transition CLINIC - Obedience Training2:04
9 months ago xHamster

Sissy Transition CLINIC - Obedience Training

Amateur American Anal Bareback Bbc Bdsm Big cock Bisexual Butt
I love being a sissy1:06
9 months ago xHamster

I love being a sissy

Domination Fat Fetish First time Hd Humiliation Lingerie Pissing Spanking
Inexperienced Crossdresser tries out sex machine - Sissy's juicy booty gets pounded5:39
6 months ago Gay Bingo

Inexperienced Crossdresser tries out sex machine - Sissy's juicy booty gets pounded

Amateur American Anal Ass Big ass Butt First time Homemade Lingerie
Crossdressing sissy, young twinks, and a hung stud get naughty5:17
6 months ago Gay Bingo

Crossdressing sissy, young twinks, and a hung stud get naughty

African Amateur Anal Ass Bareback Big ass Big cock Black Black cock
Amazing Sissy Crossdresser Fist Time She Wearing His Sister's Panty and Bra ,Show Her Ass and Big Dick5:17
6 months ago xHamster

Amazing Sissy Crossdresser Fist Time She Wearing His Sister's Panty and Bra ,Show Her Ass and Big Dick

Amateur Anal Asian Ass Big ass Big cock Crossdresser Cumshot Cute
Petite sissy sub being subjugated to her girlfriend on movie call16:18
6 months ago 4Gay

Petite sissy sub being subjugated to her girlfriend on movie call

Amateur Anal Ass Cuckold Dick Domination First time Handjob Hd
My Evolution from Guiltless Fellow to Depraved Sissy Bitch17:55
1 year ago 4Gay

My Evolution from Guiltless Fellow to Depraved Sissy Bitch

Amateur Anal Bbc Big ass Blonde Compilation Cute Feet First time
Ebony superchub sissy takes anal plugs and dildo for the first time6:33
4 months ago xHamster

Ebony superchub sissy takes anal plugs and dildo for the first time

Amateur American Anal Big ass Black Butt Chubby Dildo Ebony
First-time sissy humiliation with face-spitting10:27
4 months ago Gay Bingo

First-time sissy humiliation with face-spitting

Balls Big cock Brunette Daddies Deepthroat Emo First time Gagging Goth
diminutive pansy sissy gets crazy bum sex boinked in the caboose20:30
3 months ago 4Gay

Diminutive pansy sissy gets crazy bum sex boinked in the caboose

Amateur Anal Bareback Big cock Couple Crossdresser Dick First time German
back to top