SHEMALE • FIRST TIME 3,868 videos

Popular Latest Top rated

11:21 79%

First time with a

4 years ago

TrannyOne

first time, hardcore, amateur
04:30 81%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
08:12 72%

My first time with a transsexual

1 year ago

JizzBunker

first time
08:07 85%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, blowjob, german, wife, cumshot, masturbation
08:00 57%

Christmas orgy first time Slumber Party

6 years ago

IcePorn

teen (18+), first time, party
15:00 63%

Lustful shemale incredible porn movie

1 year ago

XoZilla

small cock, shemale, first time, missionary
18:51 74%

Fucked by a man for the first time.

5 years ago

ShemaleZ

POV, first time, asian, teen (18+)
06:54 76%

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

2 years ago

TrannyOne

small cock, facial, slut, small tits, first time, domination
10:04 56%

First-ever Time date A Trans female

1 week ago

ShemaleTaxi

public, shemale, creampie, POV, 18, caught, reality
18:30 71%

Made His First Time Unforgettable

1 month ago

BeMyHole

shemale, first time, blowjob, domination, hardcore
12:21

First Time Feminized Means First Time Fucked in the Ass

8 months ago

xHamster

first time, domination, big cock, amateur, beauty, cum in ass
14:56 58%

Domme T: first-ever Time rope-On Virgin

1 year ago

ShemaleTaxi

shemale, first time, kissing
03:23 88%

First Time Fucked by a Shemale

6 years ago

ShemaleZ

18, first time
05:29 51%

Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson

5 years ago

xHamster

teen (18+), russian, first time, sissy, shemale and girl, crossdresser
05:18 80%

Boy had first-ever time rectal with shemale

5 years ago

VideoSection

first time, hardcore
06:09 86%

Amateur Newhalf Ladyboy Rimmed Before Analsex

4 years ago

ShemaleZ

shemale, asian, russian, first time
31:37 80%

Shy Couple first time shemale experience 2

5 years ago

AShemaleTube

couple, shy, first time
14:29 64%

College Amateur Aubreys first Porn

6 years ago

TrannyGem

car, swallow, college, first time, shemale
29:01 87%

Ts Bianca (bibibratx) top for the first time with Cristiano

9 months ago

AShemaleTube

big ass, interracial, big cock, ass, domination, first time, shemale fucks guy
26:00 81%

First-time blowjob experience with big cock in missionary position featuring Jessica Kate

2 months ago

XXXVogue

amateur, shemale, spanish, big ass, big cock, ass, first time
06:15 85%

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

3 years ago

ShemaleZ

stockings, small cock, POV, facial, domination, slut, first time
08:23 48%

Straight Guy Fucked By Trans Woman For First Time

3 years ago

ShemaleZ

big cock, first time
03:32

Very First time letting my beau put it in my ass

2 months ago

TrannyGem

hardcore, amateur, first time
10:00 74%

Boy first time with tranny

13 years ago

xHamster

first time
21:06 76%

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

4 years ago

TrannyOne

first time, beauty
10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

dildo, redhead, solo, toys, first time, shemale
06:05 73%

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

2 years ago

ShemaleZ

amateur, femdom, POV, shemale and girl, webcam, first time
03:06 81%

Transgender scene with sultry fiancée from Grooby Girls

4 weeks ago

PornHat

feet, solo, first time, nipples, glasses, jeans
15:53 83%

Vol #10: screwed For The very first Time on Femout

3 weeks ago

ShemaleTaxi

big cock, shemale fucks guy, small cock, kissing, first time
08:00 77%

741m584-g02 My Son Who Came Back For The First Time In

2 years ago

GetTranny

hairy, japanese, first time
10:28 73%

Boy very first time with trans

5 years ago

HDSex

first time, amateur
08:09 77%

My very first time

4 years ago

TrannyOne

first time
07:11

My Blonde Busty Trans Stepsister Wants A Anal For The First Time

5 days ago

GetTranny

big ass, cum in mouth, first time
16:11 60%

Is this your first time fucking a hot tranny

4 years ago

TrannyOne

first time, amateur
17:05

Vol #4: plowed For The very first Time on Femout

Yesterday

ShemaleTaxi

first time, shemale fucks guy, small cock, shemale, hardcore, taxi, anal
15:00 78%

Trans Teen Cock Deflowering?! My First Time with Larissa-ts!

6 months ago

$$ FapHouse

amateur, small cock, shemale, creampie, 18, shemale and girl, bareback
21:59 84%

Trans nailing a heterosexual stud for the first-ever time

2 years ago

TrannyGem

homemade, reality, first time, shemale fucks guy, amateur, blowjob
03:53 79%

Old man first time with shemale

1 year ago

AShemaleTube

mature, amateur, homemade, shemale, old man, first time, shemale fucks guy
01:28 78%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
11:13 76%

Ultra-cute teenager towheaded shemale masturbates first time

6 months ago

ShemaleTaxi

solo, cute, shemale, small tits, first time
08:07

First Time Trans Alice Gets Wrecked

5 days ago

ShemaleZ

shemale, first time
06:20 65%

Teenager Trans and Beau very first Ravage

5 years ago

TrannyGem

teen anal (18+), first time
51:27 67%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
07:43

Crystal Phoenix gets plowed hard for her first time with her big booty

1 week ago

XXXVogue

teen anal (18+), femboy, teen (18+), first time, shemale
15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
17:35 62%

Young dude screwed in the ass for the first time by a tranny

4 years ago

ShemaleMovie

first time, shemale fucks guy, blowjob, amateur
21:52 76%

Brand New Trans Cutie Pixie Pond Fucked by a Man for the First Time Ever

3 months ago

$$ FapHouse

amateur, shemale, blowjob, POV, anal, couple, interracial
28:17

Perverted Couple Hires a Shemale for the First Time for a Threesome

Yesterday

$$ FapHouse

first time, shemale fucks guy, shemale
22:08 69%

Trans screwing a heterosexual boy for the first-ever time

1 year ago

ShemaleTaxi

amateur, shemale, blowjob, anal, BDSM, first time
08:58 74%

First time swallowing cum

1 year ago

AShemaleTube

amateur, blowjob, lingerie, crossdresser, swallow, sissy, first time
07:42 63%

He Wears My Panties For The First Time Pov - Teaser Video

2 years ago

GetTranny

panties, first time
08:15

First-ever time fuck for a teenage shemale

5 years ago

VideoSection

first time
09:30 78%

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

1 year ago

Upornia

asian, shemale, interracial, big cock, first time
05:13 71%

Lena And A Married Males First Time

2 years ago

TXXX

amateur, POV, first time
05:01 88%

Tranny is trying Anal for the first time

7 years ago

AShemaleTube

first time, shemale, small tits, ladyboy, bareback, anal
05:17 55%

Cd and Str8 First time

6 years ago

TXXX

first time
06:08

My first-ever time with a trans. Part 1 While my friend rests

1 month ago

ShemaleMovie

big cock, teen (18+), couple, amateur, first time
08:00 62%

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

2 years ago

GetTranny

hairy, japanese, first time, asian, 18
13:25

His very first time with a ladyboy

7 years ago

HDSex

asian, nylon, first time
12:00 87%

Naughty Michael Delray fucks tranny for the first time

2 years ago

YourLust

stockings, big cock, first time
12:08 80%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
08:26 92%

TRANS NYMPH GETS HUMPED BY ANOTHER TRANS DAME FOR THE FIRST-EVER TIME

1 year ago

TrannyGem

big tits, facesitting, 18, shemale and girl, blonde, babe, small tits
06:14 78%

First time with a Shemale Escort

6 years ago

AShemaleTube

mature, lingerie, first time, escort, latina
06:15 71%

Shemale fucked guy for the first time and she enjoyed hardcore anal sex

1 year ago

AShemaleTube

shemale fucks guy, shemale, big cock, bareback, first time, hardcore
03:25 44%

Teenie Ginger-Haired uses a String on for the First-Ever Time!(more Content Coming Shortly)

2 years ago

TrannyGem

amateur, femdom, teen (18+), deepthroat, first time, femboy
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
08:19 75%

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

2 years ago

xHamster

handjob, amateur, solo, first time, asian
07:45 86%

German first-timer 18yo she-male next door do homemade rectal pornography

6 months ago

TrannyGem

amateur, homemade, german, couple, girlfriend, college, sissy
15:51

Vol #8: boinked For The first Time on Femout

4 days ago

ShemaleTaxi

anal, shemale, shemale fucks guy, big cock, small cock, bareback, hardcore
18:50 88%

AUBREYS FIRST-EVER TIME

5 years ago

TrannyGem

shemale, first time
16:00 88%

Femdom Ts Initiation: First Time Fuckers

4 years ago

ShemaleZ

femdom, threesome, first time, fetish
10:01 70%

That boy had first time sex with an experienced milf tranny

11 years ago

MyLust

first time
03:08 93%

Porking Crossdresser For The Very first time in my life

1 year ago

KeekAss

amateur, crossdresser, first time, anal, blowjob, shemale
05:17 57%

VRB TRANS First time date with hot small tits shemale VR Porn

5 years ago

AShemaleTube

first time, shemale fucks guy
06:20 71%

Watch busty tgirl Emma Rose her first time sex with a woman

1 year ago

AShemaleTube

first time, shemale, blowjob, redhead, big tits
08:58 62%

First Time swallowing cum

7 years ago

xHamster

lingerie, swallow, first time, amateur
28:10 81%

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
09:47

My Hero Academia Sleepover (Futa on Female)

Yesterday

HDSex

first time, futanari
19:52 88%

Shemale teen with big schlong lets stud shag her in the ass

8 months ago

ShemaleMovie

ass, skinny, sissy, first time, shemale fucks guy, cum in ass
26:22

Shemale Fucks Petite Transgirl for the First Time in the New Year

6 months ago

$$ FapHouse

cumshot, homemade, first time, shemale, couple
23:47 67%

Guys first Time with Tgirl

4 years ago

TrannyOne

69, first time
02:01

This is my very first time attempting buttfuck fuck-a-thon using a enormous fake penis

3 months ago

TrannyGem

shemale and girl, first time, dildo, solo, amateur, penis
08:27

Draped ladyman Surprise sucky-sucky vibration First-Ever Time

5 years ago

TrannyGem

surprise, vibrator, first time
16:12 83%

ADULT TIME - Sexy T-Girl Brittney Kade Seduces Nervous Straight For FIRST TIME TRANS FUCK!

1 month ago

SomePorn

first time, shemale, seduced
03:20 62%

Homemade reality demonstrate butt assfuck

2 years ago

TrannyGem

feet, homemade, big ass, brazil, first time
06:25

Scorching chinese Transbabe Ys first-ever time with huge hard cock

7 months ago

ShemaleTaxi

chinese, anal, first time
03:48

Daniels Fucks Her Male Friend For The First Time - Danni Daniels

1 month ago

PePorn

blonde, shemale, first time
07:01

Femboy in college uniform gets a hardcore pegging session

5 days ago

XXXVogue

college, first time, femboy, pegging
18:47 50%

The Pill Episode 2 - Chris First Time

2 years ago

JizzBunker

babe, first time
46:35 90%

First Time With A Shemale

5 years ago

BeMyHole

first time, stockings
07:07

She puts it back inwards her Asspussy cuz loves it wet - Onlyfans Veronica Sanders

2 weeks ago

ShemaleMovie

bareback, creampie, riding, first time
08:17

Cool CHICA TRANS de GRAN bootie Motando Un ENORME chest

2 days ago

ShemaleMovie

amateur, big ass, dildo, solo, beauty, black, first time
12:02

TRANSEROTICA ts Foxxy ravages Transman For The first-ever Time

Yesterday

ShemaleTaxi

first time, shemale
02:49 87%

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
06:01

Inked homo plowed passionately for first time by Asian TS

4 years ago

TrannyOne

first time
18:06

Sexually Attractive TS And Straight Guy Go At It For The First Time! - Shemale

4 years ago

HomemadeXXX

amateur, first time
14:58 83%

My first time with a trans girl !!

11 months ago

xHamster

amateur, homemade, teen (18+), shemale, lingerie, shemale and girl, big cock
06:30

Dangling Out with my fresh Acquaintance

3 days ago

TrannyGem

ladyboy, first time, feet, ass, sissy, homemade, amateur
10:32 88%

First Time Bbc For Cute Ts

2 years ago

TXXX

cute, stockings, big ass, interracial, bareback, BBC, first time
06:38

I sucked a transsexual hard-on for the very first time

4 months ago

ShemaleTaxi

first time
02:25 88%

TRANSSEXUAL Kim Wagner humped young fellow

1 month ago

TrannyGem

creampie, old man, german, 18, cumshot, babe, old and young (18+)
08:10 88%

Transsexual Kim Wagner ravaged a teenage +18 guy

7 months ago

ShemaleMovie

teen (18+), blowjob, german, teen anal (18+), BDSM, 18, domination
15:59 57%

Tranny shag a white fellow in donk

4 years ago

TrannyGem

riding, big cock, mask, first time, cum in ass, shemale fucks guy
15:30

Vol #2: boinked For The first Time on Femout

1 month ago

ShemaleTaxi

first time, shemale, casting, small cock, anal, big cock
08:10 73%

Mummy pulverizes teen with strap on first time Risky bday Capers

1 year ago

ShemaleMovie

first time, teen (18+), strapon, shemale, hardcore
03:41 69%

Anonymous Random Grindr Fuck - First Time With Trans

2 years ago

ShemaleZ

amateur, stockings, creampie, bareback, first time
14:09 67%

Venus Lux Fucks First Time Bottom JakeD

1 year ago

IcePorn

first time, shemale fucks guy
49:16 71%

Bbc first 1st time rawdog party

1 month ago

AShemaleTube

amateur, shemale, party, interracial, big cock, group, BBC
16:52

My first Time

4 years ago

TrannyOne

first time
21:45

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

first time, shemale fucks guy
06:44

First Time Ever

6 months ago

AShemaleTube

shemale, first time
07:30

The First Time This Man Has Sex With A Trans

3 days ago

ShemaleZ

first time
04:39

My first-ever time with a nubile she-creature

6 years ago

KeekAss

skinny, first time
08:08 60%

My very first time

7 years ago

xHamster

anal, first time, shemale fucks guy
15:52

My First Time with a Shemale and the First Time

3 days ago

$$ FapHouse

amateur, first time, shemale, ass, ladyboy, big ass
05:09

Tight Ass Tgirl Gets Fucked For The First Time

6 years ago

ShemaleZ

tight, first time
14:14 60%

Teen Crossdresser first time anal

6 years ago

ShemaleZ

amateur, anal, crossdresser, cum in mouth, first time, cum in ass
03:06

Winning lassie - piercing scene - Grooby Girls

Yesterday

PornHat

first time, shemale, feet
08:01

Teen first time screaming which will probably be the thickest thing sh

3 years ago

TrannyOne

screaming, first time, teen (18+)
05:55

Shemale Creampies Guy for the first Time

6 years ago

ShemaleZ

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