SHEMALE • FIRST TIME 3,345 videos

Popular Latest Top rated

14:36 96%

2 old Crossdressers first time

2 years ago

TrannyOne

crossdresser, first time, lingerie, shemale
07:32 94%

Futanari stepdaughter has her first anal time with her horny mommy [Hentai Uncensored]

1 year ago

MyLust

mom, anal, big ass, MILF, orgasm, big cock, futanari
05:14 94%

First-ever time going knuckle deep in taut milky culo of nubile she-male

4 years ago

KeekAss

handjob, stockings, shemale, fisting, masturbation, blonde, toys
03:08 92%

Porking Crossdresser For The Very first time in my life

3 months ago

KeekAss

amateur, crossdresser, first time, anal
20:04 92%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

3 years ago

xHamster

couple, interracial, first time, post op, ass
44:17 92%

Kendall Penny - Southern Sass Submits For The First Time!

2 years ago

ShemaleZ

stockings, fetish, BDSM, ass, first time, brunette
03:06 91%

FEMOUT XXX - New Tgirl Called Rachel, Gorgeous And Amazing Masturbating

1 month ago

TrannyGem

cute, small cock, solo, tattoo, masturbation, blonde, jeans
05:01 91%

Tranny is trying Anal for the first time

6 years ago

AShemaleTube

first time
05:55 91%

Premiere: Ashley Is Fucked By A Shemale And Swallows For The First Time Transsexual Sperm! 6 Min With Ashley Cumstar And Rosella Extrem

2 years ago

ShemaleZ

sperm, swallow, group, cum in mouth, first time, fetish
18:51 91%

Fucked by a man for the first time.

4 years ago

ShemaleZ

POV, first time, asian, teen (18+)
10:32 89%

First Time Bbc For Cute Ts

1 year ago

TXXX

cute, stockings, shemale, big ass, interracial, bareback, BBC
05:13 89%

She fellates a thick FUTA salami for the very first time

1 year ago

TrannyGem

cartoon, cum in mouth, futanari, first time
09:11 88%

Adorable eighteen Yr Elderly Teenie TGirl With Giant Bootie Entices Stud Into Fuckin Her

1 year ago

TrannyGem

fat, anal, interracial, 18, bareback, asshole, first time
04:50 88%

Inexperienced Teen Fuck My Ass For The First Time, Did He Cum Quickly?

1 year ago

BeMyHole

teen (18+), creampie, chubby, teen anal (18+), BBW, nipples, first time
08:05 88%

Skinny Trans Teen Fany Menezes Tries The Machine for The First Time

1 year ago

TXXX

machine, small tits, first time, solo
06:15 87%

Getting Dominated And Sucking Cock For The First Time Like A Little Slut With Facial 7 Min

2 years ago

ShemaleZ

stockings, small cock, POV, facial, domination, slut, first time
08:42 87%

Redhead ladyboy Lily Demure crazy sex movie

1 year ago

XoZilla

facial, cum in mouth, first time, cum in ass
06:32 87%

Your First Time Getting Fucked by a Trans nymph: First rendezvous GFE point of view Femdom

1 year ago

ShemaleTaxi

femdom, asian, filipina, domination, first time
14:58 87%

My first time with a trans girl !!

2 weeks ago

xHamster

amateur, homemade, teen (18+), shemale, lingerie, shemale and girl, big cock
13:04 86%

She made me cum twice! first-ever time boinking Britney from Tantaly - Emily Adaire

1 year ago

ShemaleTaxi

stockings, small cock, shemale, german, solo, cumshot, big cock
53:12 86%

First time anal couple sex blonde tgirl

5 years ago

AShemaleTube

homemade, shemale, blowjob, anal, couple, ass to mouth, webcam
12:23 86%

So its your first-ever time with a trans doll (Wholesome Jerk Off Instructions)

3 years ago

KeekAss

doll, instruction, JOI, first time, jerking
21:39 86%

Jamie French And Erica Cherry Fuck For The First Time And They Fuck Hard! Ots764

3 years ago

TXXX

french, first time
16:00 84%

Femdom Ts Initiation: First Time Fuckers

4 years ago

ShemaleZ

femdom, threesome, first time
15:32 84%

Russian Femboy Fucks With Mistress For The First Time With A Huge Strapon Tied With A Chastity

3 years ago

ShemaleZ

femdom, strapon, russian, fisting, tied, first time, chastity
18:15 83%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

3 years ago

TrannyGem

femdom, train, anal, instruction, wife, fisting, bondage
11:21 83%

First time with a

3 years ago

TrannyOne

first time, hardcore
04:30 83%

Topping a guy friend for the first time!!!

3 years ago

TrannyOne

first time
17:21 82%

I Fuck A Tranny Girl For The First Time 4k

2 years ago

ShemaleZ

big ass, shemale and girl, first time, brunette, big tits, amateur
32:51 82%

French tgirl : his first time with a sexy dicky girl

3 years ago

AShemaleTube

french, outdoor, ass to mouth, shemale and girl, blonde, first time
13:00 82%

Trans Verbal Demands -Elegant Look With Glove And Sweet Dress

2 years ago

xHamster

cute, gloves, dress, first time
06:25 82%

Holy hell, what a super hot threesome with cougar Dee Williams. This is the very first time that Ellas met Dr. Williams and they are understandably a bit nervous. Dr. Williams do everything she can to put Ella at ease

2 years ago

ShemaleTaxi

teen (18+), blowjob, threesome, teen anal (18+), cougar, deepthroat, taxi
09:39 82%

My first-ever time with a trans. Part trio. I shag her rich donk

1 year ago

KeekAss

crossdresser, ass licking, first time
18:50 82%

AUBREYS FIRST-EVER TIME

4 years ago

TrannyGem

shemale, first time
32:17 82%

Helena Price - First Time With A Ladyboy Hd

3 years ago

ShemaleZ

shemale, big tits, ladyboy, tattoo, ass licking, first time
27:35 81%

Ts Aubrey Kate gives him motivation and the cock for his first time

1 month ago

AShemaleTube

shemale, anal, big ass, bareback, first time, shemale fucks guy
08:07 81%

I try my transsexual friends cock for the first time

8 months ago

PornDr

handjob, beauty, shemale, blowjob, german, wife, cumshot
23:22 80%

Fucked for the First Time

4 years ago

BeMyHole

femdom, latex, dogging, panties, first time, shemale fucks guy
21:59 80%

Trans nailing a heterosexual stud for the first-ever time

1 year ago

TrannyGem

homemade, reality, first time, shemale fucks guy
16:42 80%

I Recently Acquired A Giant Tentacle Dildo, And In This Video I Use It For The First Time

1 year ago

BeMyHole

amateur, stockings, dildo, solo, tentacle, first time
18:19 79%

Barbie Femmes Dont Need A Ken. They Have Their Own Peckers

6 months ago

TrannyGem

teen (18+), shemale, creampie, 18, shemale and girl, cumshot, masturbation
17:26 79%

Alexandra Bxl In Young Guy Fucked In The Ass For The First Time By A Tranny

3 years ago

ShemaleZ

mature, first time, shemale fucks guy, shemale, amateur
06:16 79%

Brunette trans with a monster cock Blacksharon jerks off very hot and makes his balls bounce to the rhythm of her masturbation

11 months ago

JizzBunker

ebony, orgasm, solo, monster, first time, thai
05:18 79%

Boy had first-ever time rectal with shemale

4 years ago

VideoSection

first time, hardcore
21:06 78%

Hot guy gets his ass plowed for the first time by a nasty shemale beauty

3 years ago

TrannyOne

first time, beauty
02:57 78%

Modest tranny lets her new boyfriend fuck her tight hole for the first time.

1 month ago

AnySex

amateur, POV, blowjob, anal, first time, boyfriend
06:54 78%

Getting dominated and sucking cock for the first time like a little slut with facial

1 year ago

TrannyOne

small cock, facial, slut, small tits, first time, domination
06:11 78%

Ladyboy Thippy & Noi first time 3 some

5 years ago

TXXX

ladyboy, gangbang, first time
09:30 78%

Asian Transgirl Daniella Teas First Time Getting Fucked By A Guy On Video - Rough Sex

3 months ago

Upornia

asian, shemale, interracial, big cock, first time
06:05 78%

Your First Time Getting Fucked By A Trans Girl: First Date Gfe Pov Femdom

1 year ago

ShemaleZ

femdom, shemale and girl, webcam, first time, solo
02:49 77%

Gimp White Fellow Deep Throats Meatpipe Before Getting Destroyed By Serena Cocoa’s Lollipop For The First-Ever Time

1 year ago

KeekAss

ebony, first time, shemale fucks guy
16:12 77%

Stephie scarlet first time pegging a tgirl

1 year ago

IcePorn

pegging, first time, amateur
31:37 77%

Shy Couple first time shemale experience 2

4 years ago

AShemaleTube

couple, shy, first time
14:51 77%

Sophie & Quinns Very First Time

3 years ago

KeekAss

shemale, lesbian, shemale and girl, first time
11:09 76%

My First Time With A Shemale From Tantaly - Lina Paige

2 years ago

HClips

german, toys, first time
06:14 75%

First time with a Shemale Escort

5 years ago

AShemaleTube

mature, lingerie, first time, escort
10:00 75%

Boy first time with tranny

12 years ago

xHamster

first time
28:10 75%

My Trans Girlfriend Fucks Me For The First Time. She I Love How She Fucks My Ass

1 year ago

ShemaleZ

amateur, redhead, girlfriend, first time
02:00 75%

My first time with a BBC

7 months ago

TrannyOne

anal, BBC, amateur, first time
06:15 75%

Marilyn Johnson first time to blow shemale meaty cock

2 years ago

AShemaleTube

first time, shemale and girl
06:00 75%

Latina teen shemale first time fucked her girlfriend

6 years ago

AShemaleTube

girlfriend, first time
04:04 74%

Anal Fisting First Time

2 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
30:46 74%

Jamie French And Bambi Bliss - First Time Ots846

2 years ago

ShemaleZ

shemale, french, ass licking, first time, stockings
18:23 73%

Barbie Girls Don't Need A Ken. They Have Their Own Dicks

6 months ago

xHamster

teen (18+), blowjob, shemale and girl, cumshot, first time
06:02 73%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

3 years ago

ShemaleZ

filipina, first time, femboy
08:01 73%

Christmas family fun and duddys step daughter blackmail first time Au

3 years ago

TrannyOne

funny, first time
10:13 73%

Real Transgender Gal Gets Ass-Fuck Smash

1 year ago

TrannyGem

homemade, teen anal (18+), british, sissy, first time, teen (18+), cute
37:57 73%

Sexy traps first Video

2 years ago

XXXDan

blonde, skinny, small tits, first time
06:15 73%

Spencer Bradley first time to suck a tranny cock

2 years ago

AShemaleTube

first time, shemale and girl
18:49 72%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

1 year ago

TrannyGem

homemade, blowjob, POV, anal, russian, interracial, shemale and girl
14:29 71%

College Amateur Aubreys first Porn

5 years ago

TrannyGem

car, swallow, college, first time
08:19 70%

First Time Taste Drink My Own Cum. Handjob And Double Cum

1 year ago

xHamster

handjob, amateur, solo, first time
10:36 70%

My First Time With My New Ejaculating Fantasy Dildo

1 year ago

BeMyHole

dildo, redhead, solo, toys, first time, shemale
03:53 69%

Old man first time with shemale

1 month ago

AShemaleTube

mature, amateur, homemade, shemale, old man, first time, shemale fucks guy
28:32 69%

MY TRANS DAME MATE TONGUES CUNNY FOR THE FIRST-EVER TIME - NOOCHKA X CIRILLA

4 months ago

TrannyGem

amateur, kissing, cute, shemale, french, blowjob, lesbian
04:18 67%

Mia Thorne Trains Cherry Tgirl Mate How to Have Hook-Up UTTER MOVIE ON FANSLY

8 months ago

TrannyGem

amateur, small cock, shemale, lesbian, shemale and girl, first time
10:43 67%

Girl tries to fuck with trans first time

5 years ago

AShemaleTube

first time, homemade
17:17 67%

Skinny Ladyboy Fucks A Guy For The First Time. P2 18 Min

3 years ago

ShemaleZ

ladyboy, 18, big cock, first time, brunette
14:09 67%

Venus Lux Fucks First Time Bottom JakeD

1 year ago

IcePorn

first time, shemale fucks guy
19:58 66%

MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS

2 years ago

xHamster

beauty, small cock, creampie, anal, interracial, bareback, small tits
01:21 66%

Arab Femboy First Time Anal

3 years ago

AShemaleTube

homemade, arab, first time, femboy, domination
06:20 66%

Teenager Trans and Beau very first Ravage

4 years ago

TrannyGem

teen anal (18+), first time
51:27 65%

Little ones first time - all 3 angles

4 years ago

TXXX

asian, bareback, first time, amateur
08:58 65%

First time swallowing cum

5 months ago

AShemaleTube

amateur, stockings, shemale, blowjob, lingerie, crossdresser, swallow
08:09 65%

My very first time

3 years ago

TrannyOne

first time
23:47 65%

Guys first Time with Tgirl

3 years ago

TrannyOne

69, first time
38:29 64%

Moscardiniema - I Remember The First Time I Saw Manu On Social Media, I Was Laying In Bed And It Was About 11pm, I Literally Couldnt Believe My Eyes.

1 year ago

BeMyHole

stockings, big tits, blonde, first time, hardcore, 18
05:51 64%

POV Asian First Time Anal

5 years ago

ShemaleZ

asian, first time
08:23 63%

Straight Guy Fucked By Trans Woman For First Time

2 years ago

ShemaleZ

big cock, first time
24:59 62%

Old Futa Girl-On-Girl Tranny Humps Young Very First Time Cherry With Numerous Ejaculations - Sims four

8 months ago

TrannyGem

creampie, lesbian, shemale and girl, old and young (18+), cartoon, futanari
26:35 62%

Sissy very first Time Dressing Up For dad

1 year ago

ShemaleMovie

amateur, crossdresser, dress, sissy, first time
03:20 62%

Homemade reality demonstrate butt assfuck

1 year ago

TrannyGem

feet, homemade, big ass, brazil, first time
34:39 62%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

2 years ago

VideoSection

shemale, threesome, group, first time
03:41 61%

Anonymous Random Grindr Fuck - First Time With Trans

1 year ago

ShemaleZ

amateur, stockings, creampie, bareback, first time
09:08 61%

Tatted Guys First Time With a Trans damsel: Blows His geyser and His Mind over a Smoking oral pleasure

3 months ago

ShemaleTaxi

amateur, beauty, smoking, POV, deepthroat, cum in mouth, first time
2:36:25 60%

Yui Hatano And Hibiki Otsuki - Dass-133 First Time Nh Lesbian Sex. Kanami Kashiwagi Yu

1 year ago

ShemaleZ

lesbian, asian, uniform, first time
11:07 60%

First Time Teacher of Magic and Alice Blitz ( part 2 )

4 years ago

HClips

shemale and girl, teacher, first time
08:00 59%

Christmas orgy first time Slumber Party

5 years ago

IcePorn

teen (18+), first time, party
44:40 58%

Indian Taina - My First Time With An Indian

1 year ago

ShemaleZ

ebony, indian, shemale, interracial, big cock, first time
16:05 57%

Inexperienced real en motel de guerrero. pornography en español!

6 months ago

ShemaleTaxi

homemade, black, small cock, arab, creampie, anal, big ass
40:52 57%

Tall Trans dame penetrated humid By Tiny CIS Girl

3 months ago

ShemaleTaxi

shemale and girl, tall, shemale, first time
08:00 56%

741m584-g03 My Son Who Came Back For The First Time In

1 year ago

GetTranny

hairy, japanese, first time, asian, 18
05:17 56%

Cd and Str8 First time

5 years ago

TXXX

first time
14:56 56%

Domme T: first-ever Time rope-On Virgin

8 months ago

ShemaleTaxi

shemale, first time, kissing
08:58 56%

First Time swallowing cum

6 years ago

xHamster

lingerie, swallow, first time
05:01 55%

Old man eats teen ass first time Frannkie's a fast learner!

3 years ago

TrannyOne

teen (18+), old man, first time
08:12 54%

My first time with a transsexual

11 months ago

JizzBunker

first time
04:54 54%

First time this cute babe allows her lesbian mature aunt to lick her pussy

3 months ago

HellPorno

mature, amateur, cute, shemale, lesbian, hairy, ass licking
05:32 54%

First time

5 years ago

xHamster

mature, amateur, mature anal, first time
22:46 54%

Sissy lad gets to fuck the trans babes thick ass for the first time

2 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
08:08 54%

My very first time

6 years ago

xHamster

anal, first time, shemale fucks guy
02:28 53%

Sissy Lexie Adams Crossdresser First Time with Sex Machine

1 year ago

xHamster

stockings, crossdresser, machine, sissy, first time
05:29 51%

Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson

4 years ago

xHamster

teen (18+), russian, first time, sissy
05:57 50%

Shemale lesbian babe teen first time But the female is very

8 years ago

IcePorn

old and young (18+), first time, babe
12:53 50%

Latina MILF fucks with tranny for a first time

3 years ago

Analdin

ebony, black, strapon, lesbian, big ass, MILF, first time
12:42 50%

The nylon fetish pt2 Sissy dude very first time smash tranny

1 year ago

ShemaleTaxi

BDSM, 3D, domination, sissy, first time
14:50 50%

Legacy mess:She on the porno first-ever time, her lucky day. P2

2 years ago

ShemaleTaxi

thai, couple, asian, skinny, first time
21:03 49%

T Gurl Cums in her dress

4 years ago

xHamster

public, shemale, outdoor, dress, cumshot compilation, first time
06:46 48%

Sissys training pays off. very first time knuckle in her backside.

2 years ago

ShemaleTaxi

train, fisting, sissy, gape, first time, femboy
05:55 48%

Lana violet pov blowjob and shemale pov blowjob first time B

8 years ago

IcePorn

old and young (18+), first time

Popular Latest Top rated

Popular categories

Other free porn sites

All models were 18 years of age or older at the time of depiction. ShemaleMap.com has a zero-tolerance policy against illegal pornography.

Disclaimer: ShemaleMap.com is just a search engine. All links and thumbnails displayed on this website are added automatically. We do not own, produce, host or upload any videos displayed on this website, we only link to them.
To remove physical video file please contact owner of the website where it hosted. To remove the link and thumbnail from this website please use the report button () which is located under each video.

ShemaleMap.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering.

Copyright © 2022 ShemaleMap.com. All rights reserved. | Abuse