First Shemale - Solo - Dar.LA

First Shemale x

Solo x

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My first time outdoor

My first time outdoor

- a bit scary but exiting for me... - Anett_CD

Sophie french sissy, first outing with my new big tits

Sophie french sissy, first outing with my new big tits

Sophietravfrench

Sissy first time dildo

Sissy first time dildo

First time dildo - Annecrossdress

12 Inch Dildo - Red Latex Boots & Bodystocking CD

12 Inch Dildo - Red Latex Boots & Bodystocking CD

First time with new toy - Vtecdick - vtecdick

First test of my fuck-machine

First test of my fuck-machine

IT CAME! just a quick test vid, others will follow. - AnalSissySlut222

Becky At The Hotel - First Showgirl Performace

Becky At The Hotel - First Showgirl Performace

Becky practice hard for the Showgirl Performance. What do you think? - becky0098

Tiffanystarznheartz

Tiffanystarznheartz

First time on video - Tiffanystarznheartz

12 inch double ended dildo first time use

12 inch double ended dildo first time use

First time using this toy and going deep in my virgin hole ? - Bunny600f

finally my first sissygasm

finally my first sissygasm

i was fucking my pussy and I felt a warmth creep through me and next thing i knew i came and im soooooo happy and horny againn - Jewelthesissysub - jewelthesissysub

cindy in chastity

cindy in chastity

first time in cage - TRAPSLOVER44

First Video

Denise - Denisetrans

First time cross dressing (and I love it)

First time cross dressing (and I love it)

I started officially cross dressing the day this was uploaded. My (step) sister has some cool costumes and panties laying around plus this big dildo so I went for it while she is away, enjoy x - kekesissy

First time with the big one p1

First time with the big one p1

I love jelly dildos, soft but also hard and compact, smooth and sliding. - maddalenamariposa

Sexy Sadie's first table dance

Sexy Sadie's first table dance

Inventing somebody new, somebody hot, who wants to have more fun. - cybersexisnice2

Tgirl Marcela Ragonne Tries a Sex Machine for the First Time

Tgirl Marcela Ragonne Tries a Sex Machine for the First Time

Sexy tgirl takes off her undies and shoe her tiny tits faceable ass and dick She strokes her dick and suck dildo Then she rides a fucking machine in her ass and continue stroking dick until she cums - Marcela Ragonne - dreamtranny

Premiere marche dans la rue - first walk in the street

Premiere marche dans la rue - first walk in the street

Premiere fois que je marche dans la rue - My first time walking in the street - Jessika57

I came twice for the first time Cosplay

I came twice for the first time Cosplay

my hero academia - Twinkie Star - tommytay95

deconfined...first day

deconfined...first day

in the streets ...deconfined - sophie06000

First time with Bill

First time with Bill

fucking and being fucked by my guy doll! - nylonguy_cd

Swallow completely

Swallow completely

Did it for the first time)) - ms-sissy

Kayla fucks herself for daddy

Kayla fucks herself for daddy

Kayla fucks herself on video for the first time for daddy - KaylaCD15

My first pantyhose tease

My first pantyhose tease

Hi everyone! I'm new to Xhamster, this is the first in my set of pantyhose fetish content, please leave your feedback and support, pantyhose in this video are leggs silken mist jet black size b. - evilflow60

Kinky iris with new spike clamps, very painfull first time

Kinky iris with new spike clamps, very painfull first time

this is very painfull, new clamps with longer spikes inside, do not slip in your nipples 10/31/32 - irisnippletorture

First anal (solo)

First anal (solo)

sucksboy

Danna Valentina 20200828 first time i catch cum

Danna Valentina 20200828 first time i catch cum

recording 20200828 065849.mkv - LorenzKonrad

I was so proud when it first popped in!

I was so proud when it first popped in!

My goal for that day was to hopefully work myself up to Rambone but deep down I thought there's no way, my ass talks a big game lol but after a few hours and a lot of silicone lube, voila! lol - CleoAmor

Hung Ximena FTTV

Hung Ximena FTTV

first time trans Video Check out Ximena. The next time you see her with be with big tits. - AnaMancini

first video teasing

first video teasing

teasing tranny anal rose bud - dimitrishem

First time taking big black dildo

First time taking big black dildo

Taking 8 inches hard for the first time - 304cdslut

CDLalo My first video ever

CDLalo My first video ever

Be gentle in the comments guys,i know i am not that good looking but i want to make a lot more videos with a lot of more and different content, other people too. :) - CDlalo

First Time Sex Maschine 01 SandraCrossdy

First Time Sex Maschine 01 SandraCrossdy

First Time Sex Maschine 01 SandraCrossdy - SandraCrossDy - SandraCrossDy

My first home video

My first home video

maxxxles

Cd first time out.

Cd first time out.

CD Evelyn Genesis comes out dressed in and alley for the first time. - Cdevelyngenesis

My first vid

Anal n dildo - Emzchick1896

My first anal video

My first anal video

Mmmmmm - Ron_1978

Taking my first 7 inch + toy

Taking my first 7 inch + toy

This is an old video of mine. Recorded 2 years ago. Hope you like it. - UnpassingTrans

Jerk off with a beautiful shemale, she enjoys first

Jerk off with a beautiful shemale, she enjoys first

PVT CAM TO CAM - Casey Kisses - Panico03

My first footjob

My first footjob

My attempts to satisfy big cock with my sexy feet - MashaSissyBoi

T Gurl Cums in her dress

T Gurl Cums in her dress

First time outside dressed this year. Got me so horny I had to cum in my dress. See my bra collection at end of video - silkydrawers

Crossdress and go out for first time at midnight.

Crossdress and go out for first time at midnight.

longung

xbeautifulandhot 2020-08-10 did not missed the first cum

xbeautifulandhot 2020-08-10 did not missed the first cum

bandicam 2020-08-10 18-01-06-506.mkv - LorenzKonrad

My very first time

My very first time

My first time fucking my asspussy!! Wass feeling how my dildo was opening hes way true - catitalatina22

first anal dildo sissy

first anal dildo sissy

SissySarah13

My first game with my asspussy ... Don't judge strictly

My first game with my asspussy ... Don't judge strictly

VicoSun

First time anal dildo riding

First time anal dildo riding

secretc

Giant Anal Plug

Giant Anal Plug

Christy gets her big plug in for the first time. - Christy Connor - ChristyConnor

First job no cum

First job no cum

No cum fark - Shemalelover01z

SWEET ANGIE 2020-09-10 she does nothing -good for first time

SWEET ANGIE 2020-09-10 she does nothing -good for first time

bandicam 2020-09-10 14-29-59-175.mp4 - LorenzKonrad

Maid Joanna's First Hypno Session Pt2

Maid Joanna's First Hypno Session Pt2

As the hypnosis continues Maid Joanna is increasingly unable to resist and becomes more turned on, she practices her oral skills on her plug before inserting it and then uses her fleshlight to climax - Just_Jo2161

The beautiful, the magnificent,Suzanna Holmes

The beautiful, the magnificent,Suzanna Holmes

The first time God actually got things right, a beautiful woman that's not likely to saddle you with fatherhood lol - Suzanna Holmes - MarianneCDUK

First Time In New Rubber Doll Boob Suit

First Time In New Rubber Doll Boob Suit

Quick tease from the first wearing of my new boob suit - thetightness

Cumming without hands

Cumming without hands

I just tried to cum without hands in first time. I was loving that.... - Alexxxiana

Very First Time in a Diaper!

Very First Time in a Diaper!

I slept and pee peed in my diaper, woke up with a really heavy wet diaper that my mommy had to change me she kissed my wiener and I sucked on her big boobies and mommy gave me milk andmade out with me - BrittanyCumSlut18

Me n my toy

conor138

Sissy TGirl Lucy Pissing In Her Chastity Cage at SheWorld

Sissy TGirl Lucy Pissing In Her Chastity Cage at SheWorld

Lucy is wearing her Chastity cage for the first time and needs to take a pee whilst visiting SheWorld sex Club. - SpikeEssex

Trying to do my first dp

Trying to do my first dp

A lil spun fun - Bobbie Bunzz - redbonecd

One of Riley's first homemade cumshot videos from camming.

One of Riley's first homemade cumshot videos from camming.

Watch Sexy, femme Riley Gamz shoot a load on her own sexy feet!! - legs4dayze99

Jemima's first ever sissygasm is accidental

Jemima's first ever sissygasm is accidental

Jemima's very first ever sissygasm - I was fucking myself with a DIY dildo and accidentally came handsfree onto a tissue on the floor! ..and now I want lots more!! - jemimaheart

Cds First time with a new fuck machine.

Cds First time with a new fuck machine.

First time with my new toy, really need a camara mount for better angles.. dildo is 9"x 2" - Eastcoastthang

Sissy Samantha first kornfield 2020

Sissy Samantha first kornfield 2020

Sissy_-_Samantha

It Won't Fit on the First Try

It Won't Fit on the First Try

I don't know if I told y'all or not, but it do take a couple 2, 3 times for Big Blue The Plug to fit comfortably. Other than that my ass will not let him in. Now that's tight opposed to most. - DevineCaramel

Sophie french CD, first exit after confinement

Sophie french CD, first exit after confinement

Travesti français s'exhibe sur le quai de la gare de train - Sophietravfrench

First time with the big one p2

First time with the big one p2

Training for a crossdresser ass pussy. I'd love to take it all inside my butt hole, but I have to train a lot to get it properly. Here you can see how I practice for my and your enjoyment ... - maddalenamariposa

i get the first cum in my ass

i get the first cum in my ass

my memory of my first creampie - LaraLoveBu

My first transitioning daytime

My first transitioning daytime

I love wearing sexy dress - anatransa

My First Video

NYLON-DVL

Suprise ass

Ass toys skrit - Kasiatr

First time driving dressed

First time driving dressed

This is the first time I drove my car fully dressed. I was so excited...as you can see ;) xx. - nearlyrich

Sissies First Inflatable Butt Plug

Sissies First Inflatable Butt Plug

SissyVicky_PM

First big black dildo barely fits in me

First big black dildo barely fits in me

First time I've had anything bigger than 6 inches - 304cdslut

TS Rayra Spanick First Time Machine Sex

TS Rayra Spanick First Time Machine Sex

Horny shemale babe shows her tits and dick She strokes her dick She runs the fucking machine in her mouth Later she runs the machine and make it fuck her asshole while she strokes her dick - Rayra Spanick - dreamtranny

First time in catsuit

First time in catsuit

Tv-julie

Juniper's First Dildo

Juniper's First Dildo

SissyJuniper90

asian sissy dripping in chastity first time vibrator

asian sissy dripping in chastity first time vibrator

first try with vibrator in my ass with a chastity wearing heels - warhaha

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