SHEMALE • SISSY TRAINING 656 videos

Popular Latest Top rated

18:46 60%

Destroyed Climax For Circumcised DORKS (with Lina Lux)

1 week ago

TrannyGem

amateur, femdom, shemale, POV, german, train, fetish
17:44 86%

Extraordinary Sissy Bad Dragon Gaping and FemDom Hole Destruction with Speculum flash Off by mistress Mercer

1 week ago

ShemaleMovie

femdom, sissy, BDSM, shemale, anal, strapon
16:47

Inhale My Femboys Dick (with Lina Lux)

1 week ago

TrannyGem

amateur, femdom, shemale, blowjob, POV, train, fetish
28:06 59%

SADISM & MASOCHISM Sissy fellate instructing with clyster!

3 months ago

TrannyGem

amateur, stockings, shemale, blowjob, train, instruction, fetish
17:35 33%

Adore Her Femboy Marionette (with Lina Lux)

1 week ago

TrannyGem

shemale, asian, amateur, femboy, sissy, femdom
17:13 50%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

4 months ago

TrannyGem

teen (18+), crossdresser, british, 18, whore, slut, sissy
21:13 81%

Teen t-girl College Fuck Anal SEX TRANS dame finishes off trans porn

1 month ago

ShemaleTaxi

beauty, small cock, shemale, train, orgasm, ladyboy, babe
18:28 80%

GOOD-SIZED Belt Dick Pegging for V-Card Sissy Victim Demolishing her Trampy Crevice by Domina Mercer

4 years ago

TrannyGem

femdom, strapon, lesbian, train, bondage, dildo, crossdresser
22:45 81%

Amateur Couple and Trans - Train

1 year ago

xHamster

amateur, teen (18+), train, threesome, couple, teen anal (18+), sissy
15:04 68%

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

4 years ago

TrannyGem

mature, femdom, mature anal, train, granny, british, dirty talk
18:28 83%

GIGANTIC Strapon Pegging with Bad Dragon and Hankey for whorish Sissy bi-atch by domme Mercer

2 weeks ago

VideoSection

sissy, shemale, BDSM, anal, pegging, strapon, train
15:35 61%

Sissy Hypno #2: Becoming A Cock Slut

4 years ago

xHamster

train, sissy, creampie
34:54 85%

Gorgeous tgirl Angel dildo training

1 year ago

AShemaleTube

train, anal, big tits, dildo, masturbation, ass, toys
23:35

Satin-clad sissy maid Sissy Candy Sparkle gets dominated by her nymph in bondage and loses her virginity

1 week ago

XXXVogue

bondage, crossdresser, shemale, maid, domination, sissy
1:27:33 71%

Sissy in Training

6 years ago

xHamster

train, domination, sissy
17:29 85%

TS Schoolgirl Sasha Helps you Learn about Shemale Anatomy

6 years ago

TrannyGem

train, instruction, british, dirty talk, small tits, JOI, sissy
17:07 66%

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

1 year ago

TrannyGem

mom, fat, instruction, facesitting, shemale and girl, stepmom, domination
22:39 79%

Sissy Crossdresser - Amateur Couple And Trans - Train

11 months ago

ShemaleZ

amateur, stockings, teen (18+), shemale, POV, train, threesome
1:02:22 71%

Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5

1 year ago

xHamster

amateur, train, anal, crossdresser, dutch, bareback, skinny
18:22 66%

Sissy breezy Is What u Will Always Be

5 years ago

TrannyGem

cute, train, BDSM, spanking, clit, compilation, prostitute
42:54 52%

My Path to Life as A Sissy Hoe

6 years ago

TrannyGem

train, whore, sissy, compilation
21:04

Webcam session of trans femboy bondage & discipline Sissy fuckslut Alina old stuff

4 weeks ago

ShemaleMovie

train, bondage, dildo, BDSM, deepthroat, webcam, sissy
17:32 63%

Sissy bbc training Encouragement Crossdresser bi-racial Fiona Fortune

1 month ago

HDSex

amateur, black, shemale, creampie, train, anal, crossdresser
26:38 77%

Trained to Be Completely Subservient to Him

5 months ago

$$ FapHouse

amateur, black, train, interracial, bareback, sissy, hardcore
41:04 57%

Your friends futa mommy takes control of your backside during the sleepover

1 month ago

XXXVogue

dildo, futanari, sissy, mom, shemale
20:59 50%

White Sissy Virginity Instructing (Smash Machine)

1 month ago

TrannyGem

femdom, teen (18+), POV, instruction, fetish, teen anal (18+), bondage
17:09 59%

Feminization - Sissification - Sissy instructing - Sissy Support - full version

1 year ago

ShemaleMovie

black, POV, train, anal, instruction, 18, full movie
20:10 81%

Ass fucking Update two: queen Edition!

6 months ago

ShemaleMovie

beauty, stockings, train, dildo, solo, ass, toys
27:39 80%

Trained to Be a Good Slut

6 months ago

$$ FapHouse

train, couple, lingerie, tattoo, facial, heels, bareback
20:41 72%

Sissy Poppers Hypnose training IV

4 years ago

ShemaleTaxi

train, sissy, shemale
23:19 87%

Sissy Trained And Owned By Big Black Penis Bull With Sasha Desade

2 years ago

ShemaleZ

black, POV, train, interracial, gangbang, BBC, sissy
21:39

Latex sissy maid Sissy Candy Sparkle gives a deep throat to her nymph and rides her dildo machine

1 month ago

XXXVogue

toys, latex, shemale, sissy, dildo, maid
20:21 79%

Forced By Step Mommy Sissy Enema And Anal Training

2 years ago

ShemaleZ

mom, sissy, stockings, train
21:15 83%

Sissy Training With Bailey Love

2 years ago

HClips

shemale, train, sissy, amateur
28:06 93%

Ryu Nymph Stretches her Arse with a Monster can

4 years ago

TrannyGem

amateur, small cock, train, boots, big tits, monster, cumshot
15:15 76%

TS Anna Katt Prepares Lilys Ass for Cock

6 years ago

TrannyGem

small cock, lesbian, train, anal, dildo, glasses, reality
16:02 50%

T-GIRL JIZM COMPILATION STAMINA COMPETE - Can you make it to the end ?

3 months ago

TrannyGem

amateur, train, orgasm, shemale and girl, compilation, masturbation, ass
19:58 80%

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

4 years ago

ShemaleZ

handjob, femdom, latex, train, fetish, crossdresser, domination
15:39 94%

Whife *

6 years ago

TrannyGem

train, anal, bondage, ladyboy, crossdresser, cumshot, babe
38:07 58%

Petra,s 7th training

2 months ago

ShemaleTaxi

huge dildo, anal, double anal, crossdresser, toys, taxi, sissy
1:02:24 66%

Stunning Tgirl shoots a pile of jism while getting fucked bare on date #5

1 year ago

ShemaleTaxi

amateur, beauty, train, anal, crossdresser, ass, bareback
49:25

Petras hardcore teaching includes double penetration and a massive dildo

1 month ago

XXXVogue

beauty, train, huge dildo, dildo, double anal, sissy, gape
20:49 89%

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

4 years ago

TrannyGem

femdom, latex, strapon, bisexual, train, bondage, shemale and girl
18:30 60%

Just because I can..

2 months ago

ShemaleTaxi

latex, shemale, bondage, BDSM, crossdresser, heels, sissy
18:51 50%

Sissy fuckslut Pegging Compilation Vol.1

1 month ago

ShemaleTaxi

amateur, orgasm, compilation, orgasm compilation, pegging, sissy, femboy
20:52 90%

Lindsey Training Her Sissy Slave

11 months ago

AShemaleTube

shemale, blowjob, creampie, train, lingerie, crossdresser, big cock
17:41 75%

Sissy Pussy Training

4 years ago

xHamster

beauty, public, creampie, train, bareback, JOI, sissy
16:32 88%

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

4 years ago

TrannyGem

femdom, shemale, train, BDSM, shemale and girl, big cock, deepthroat
23:09 76%

Mistress training sissies to play together

6 years ago

ShemaleZ

femdom, train, sissy
29:51

30 mins no break fellate spitroast contest!

1 month ago

TrannyGem

stockings, anal, fetish, double anal, crossdresser, contest, gangbang
15:30

Hard training to be a good sissy slut

3 weeks ago

AShemaleTube

stockings, shemale, solo, crossdresser, big cock, slut, sissy
21:45 71%

Sissy Poppers Hypnose Training III

4 years ago

xHamster

public, train
58:16 74%

Young goth femboy anal training

1 year ago

AShemaleTube

homemade, small cock, train, anal, big tits, big cock, goth
15:05

Wooly Fuckpole Adore - BrainWash Jerk Off Instructions

2 months ago

TrannyGem

femdom, instruction, compilation, jerking, deepthroat, cartoon, toys
19:58 70%

Uber-cute tiny trap anal teaching

1 year ago

ShemaleMovie

cute, blowjob, train, dildo, crossdresser, riding, toys
30:58 76%

Scotlands femdom-goddess Inka And Miss Maryln train Sissy hooker To suck penis

6 years ago

TXXX

femdom, train, hooker, BDSM, domination, penis, sissy
21:01

TRANSSEXUAL Silly Female Dom Honeypot Whips Blond Cable Kitten

4 years ago

TrannyGem

train, bondage, BDSM, 18, sissy, shemale and girl
26:34 89%

Sissy Institute Mistress Bailey Trains SISSYSLUTS - Lily DeMure + Nyxi Leon

5 years ago

BeMyHole

femdom, train, sissy
39:29

Miss Abernathys Maid training

2 months ago

AShemaleTube

solo, sissy, amateur, latex, domination, maid
20:59 65%

Breezy Teaching Jizz Slurping two

3 years ago

TrannyGem

train, swallow, riding, JOI, sissy
32:02 69%

Hot sluts sucks gigantic dicks

5 years ago

XoZilla

femdom, train, fetish, tease, slut, JOI
23:19 81%

Sissy Trained And Owned By BIG BLACK PENIS Bull

3 years ago

Analdin

train, anal, BDSM, deepthroat, penis, BBC, sissy
49:26 67%

Petra,s 9th training

8 months ago

xHamster

train, dildo, crossdresser, dutch, sissy, hardcore, femboy
15:21 85%

Hattabi4ik sissy femboy trap splatter ejaculation self shag warm humungous bootie compilation

2 years ago

TrannyGem

pissing, train, squirt, orgasm, compilation, cumshot compilation, orgasm compilation
25:17 81%

Sissy Fuckdoll Delivery

5 years ago

TrannyGem

train, bondage, BDSM, bikini, reality, slut, sissy
27:01 17%

HUMUNGOUS GAPES, Rosebutt, tummy swelling, AMPLE sugary-sweet gape farts, Twunk Jules Verne Assfuck FUCK HOLE DESTRUCTION

3 years ago

TrannyGem

farting, train, huge dildo, fetish, gape, chastity
33:06 83%

SISSY Mindcontrol instructing - Sasha de Sade & domina whisper

5 months ago

ShemaleMovie

teen (18+), shemale, femdom, BDSM, instruction, sissy
25:04 86%

Dizzy In demeaning Sissy Maid teaching!

9 months ago

ShemaleMovie

strapon, train, bondage, maid, dildo, BDSM, domination
20:51 80%

Turning the staright boys faggot

3 years ago

TrannyGem

femdom, train
30:41 67%

Submissive Ladyboy Anal Casting & Slave Training

6 months ago

$$ FapHouse

casting, teen (18+), creampie, train, couple, teen anal (18+), ladyboy
17:33 33%

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

1 month ago

AShemaleTube

shemale, creampie, train, interracial, crossdresser, creampie compilation, compilation
24:19 57%

Step mummy drills son-in-law culo and train jizm while being drilled

4 months ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
28:50 73%

Training Your Sissy

2 years ago

Upornia

stockings, shemale, train, lingerie, cumshot, sissy
19:45 85%

High Class Sissy Training

4 years ago

ShemaleZ

latex, train, BDSM, domination, sissy, brunette
17:16

Sissy seeing porno and taking phat fake penis

2 weeks ago

TrannyGem

riding, crossdresser, orgasm, dildo, anal orgasm, sissy
21:49

Futa Pleasureful Fantasy teaches anal training in this tough session

1 month ago

XXXVogue

futanari, sissy
15:19 29%

Sissy rails BIG BLACK COCK

2 months ago

TrannyGem

amateur, black, shemale, train, big ass, fetish, solo
28:27

TPP Sissy hypnosis

4 months ago

ShemaleMovie

sissy, compilation, cumshot compilation, big cock, cumshot
15:26

Sissy Candy Tries to Hide Her Dildos!

11 months ago

xHamster

bondage, maid, dildo, uniform, crossdresser, sissy
19:52 67%

Feminizaton - Sissy Instructing - COSMIC SISSY FATE

1 year ago

TrannyGem

instruction, compilation, dirty talk, cumshot compilation, JOI, BBC, sissy
20:14 89%

Sasha Desade In Sissy Fuck Training

3 years ago

ShemaleZ

stockings, train, threesome, lingerie, sissy, chastity, brunette
55:24 53%

Sissy Poppers Training To Love Cumm

6 years ago

ShemaleZ

train, gangbang
19:24 71%

Young Allie North CD wet molten teenager

7 months ago

TrannyGem

solo, crossdresser, femboy, sissy, amateur, gape
20:51 64%

Turning the staright dudes homo

3 years ago

TrannyGem

mature, femdom, train, british
21:49 88%

Insatiable bony trap railing hefty fuck stick and nutting handsfree

3 years ago

TrannyGem

train, anal, squirt, skinny, hands free, femboy
25:34

Lil knob sissy femboy have fun with protection pee on it guzzle it then jack and jism utter movie

2 years ago

TrannyGem

pissing, cum in mouth
21:55 55%

Sissy Poppers Hypnose training III

4 years ago

ShemaleTaxi

train
29:50 38%

Women Pub Vignette five: A Sissy Feminization Series

5 years ago

TrannyGem

femdom, smoking, train, crossdresser, webcam, shemale
18:42 44%

Hypnosis BR - Porra no cú - BBCs Gigantes no rabo da Paula CDZINHA

1 year ago

ShemaleTaxi

train, crossdresser, creampie compilation, compilation, orgy, BBC, sissy
26:05

Kinky Sissy female wants to get screwed so much while eyeing sissy pornography

2 weeks ago

TrannyGem

mature anal, asian, amateur, feet, korean, fetish
16:02 58%

SHE-CREATURE JIZZ COMPILATION STAMINA COMPETE - Can you make it to the end ?

7 months ago

TrannyGem

train, orgasm, compilation, cumshot, ass, cumshot compilation, orgasm compilation
16:20

Trans punk breaths in the sissy transformation gas

2 months ago

HDSex

shemale, anal, sissy, solo, femboy, crossdresser
56:10 50%

Sissy bi-atch Late Evening Supper

1 year ago

ShemaleTaxi

POV, train, orgasm, crossdresser, masturbation, close up, kitchen
20:13 76%

Tiny Dick Chastity And Mild Training

3 years ago

BeMyHole

train, fetish, uniform, cumshot, jerking, ass, toys
25:05 67%

Mistress Trains Her Sissy Gurls

3 years ago

TrannyOne

femdom, shemale, train, sissy, BDSM
19:27

Sissy Silly Step-Sister Raunchy Drill and Gargle

4 years ago

TrannyGem

train, slut, sissy
20:00 80%

Sissy Poppers Hypnose Training IV

5 years ago

BeMyHole

train
15:14

Cyberpunk Crossdresser fucktoys her vulva and slurps cum

2 weeks ago

ShemaleMovie

anal, crossdresser, sissy
1:14:34 78%

Petras 5th instructing

1 month ago

HDSex

amateur, beauty, creampie, train, anal, instruction, sissy
30:48

Compilation sissy lola wearing clothes with lil hearts and gets her bootie by lovemaking machine and huge

2 weeks ago

ShemaleMovie

huge dildo, creampie, crossdresser, compilation, creampie compilation, dildo, clothed
1:16:22

Femdom Real duo female domination pegging & strapon mistress & sissy cuck feminization total video

2 months ago

ShemaleMovie

femdom, strapon, train, couple, BDSM, domination, pegging
24:54 43%

Sissy super-bitch plumbing her butt hole with phat fake penis

5 months ago

TrannyGem

cute, femdom, teen (18+), strapon, german, train, teen anal (18+)
22:26 60%

Risky bang-out with splendid shemale in the train and in the car / Compilation

6 months ago

ShemaleMovie

amateur, beauty, public, shemale, outdoor, car, tattoo
15:46 64%

Turning My husband Into Tranny tart, lady first time with Tranny

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
24:44

Sissy Virginity Ass Fucking Ballsack Hormone Feminization Trainer Spiral

3 years ago

TrannyGem

train, insertion, slut, sissy, chastity
36:53

Petra,s day at the lake

1 month ago

ShemaleMovie

beauty, public, shemale, blowjob, train, outdoor, big cock
24:50 57%

Cute maid faints in agony because the hook-up machine senses too good✨japanese crossdresser getting off

5 months ago

ShemaleMovie

cute, train, japanese, maid, crossdresser, machine, sissy
34:48 40%

Ana Lisa 32

1 year ago

xHamster

mature, latina, sissy
22:31 93%

Ryu Woman Takes Glowing Sinnovator 20in Deep

4 years ago

TrannyGem

train, machine, gape, sissy, dildo
18:14

Sissified Masturbation Mindfuck [extreme Poppers]

6 years ago

TrannyGem

train, nipples, masturbation, dildo
22:54 73%

Petra 1e training

1 year ago

xHamster

creampie, ladyboy, crossdresser, dutch, wedding, sissy, femboy
16:51

Sissy Foot Fetish Training

1 year ago

xHamster

compilation, feet
19:45 80%

Sissy Hypno Training

1 year ago

AShemaleTube

anal, lingerie, crossdresser, sissy
26:50 79%

Jeni Justice Trained And Turned Into A Sexy Sissy

2 years ago

ShemaleZ

stockings, big ass, sissy, train
24:48 44%

Assfuck contest FOR SISSY

3 years ago

ShemaleTaxi

train, contest, taxi, sissy, femboy
16:26

Sissy Charlotte learns to suck meaty schlong

3 years ago

TrannyGem

latex, rubber, train, dirty talk, slut
32:24 73%

Sissy whore pic Bombardment Conversion Therapy

5 years ago

ShemaleTaxi

train, crossdresser, whore, taxi, sissy
34:35 56%

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

8 years ago

ShemaleZ

train, sissy
48:42

C4 Film (april 20, 2025) the boss Is a slut on a flick Conference with Her Banker.

6 months ago

ShemaleMovie

handjob, beauty, french, train, lingerie, BDSM, crossdresser
27:39 29%

I bang my stepdaughter the night her mom finds out

9 months ago

ShemaleMovie

mom, homemade, beauty, teen (18+), strapon, train, anal

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