• Sissy Encouragement Playlist

    Curated by: KinkyKimmi | updated: 10 months
Added Oldest Views Uploaded
Mistress Makes You Jerk To Gay Porn 7m
Joi 14K 94%

Mistress Makes You Jerk To Gay Porn

She Knows Your Subissive Sissy Secret 7m
Joi 19K 92%

She Knows Your Subissive Sissy Secret

JOI From Perky Teen Mistress 5m
Joi 20K 96%

JOI From Perky Teen Mistress

Your Bratty Femdom Princess HD 5m
Joi 18K 92%

Your Bratty Femdom Princess

Humiliatrix JOI HD 6m
Joi 16K 96%

Humiliatrix JOI

chastity sissy HD 2m
Sissy 39K 94%

chastity sissy

Mistress Mitsukai sissy boy 5m
POV 18K 94%

Mistress Mitsukai sissy boy

Chastity Ass Fucking 8m
Joi 39K 95%

Chastity Ass Fucking

Sissy Strapon Test 9m
Isobel Wren 17K 91%

Sissy Strapon Test

mr your feminine form HD 3m
Boots 17K 97%

mr your feminine form

514328 7m
Joi 47K 95%

514328

BBC JOI 333 (sub4all) HD 4m
Bbc 23K 94%

BBC JOI 333 (sub4all)

sissy 15m
Sissy 50K 94%

sissy

BBC JOI 282 (sub4all) HD 7m
Bbc 21K 97%

BBC JOI 282 (sub4all)

Become a cock addict 9m
Joi 57K 96%

Become a cock addict

Stroke Your Little Dick Humiliation JOI HD 10m
Joi 24K 96%

Stroke Your Little Dick Humiliation JOI

Cuck husband gets caged 6m
Cuckold 75K 98%

Cuck husband gets caged

BBC JOI 268 (sub4all) HD 14m
Bbc 23K 94%

BBC JOI 268 (sub4all)

Strap on Pov HD 6m
Strapon 18K 93%

Strap on Pov

BBC JOI 167 (sub4all) HD 8m
Bbc 14K 97%

BBC JOI 167 (sub4all)

BBC JOI 190 (sub4all) HD 5m
Bbc 33K 94%

BBC JOI 190 (sub4all)

I bought something for you sissy HD 10m
Joi 24K 97%

I bought something for you sissy

Babe Sucks Cock HD 5m
Cocksucker 51K 97%

Babe Sucks Cock

HUGE BLACK STRAPON (sub 4all) HD 8m
Shemale 35K 91%

HUGE BLACK STRAPON (sub 4all)

sissy joi HD 13m
sissy joi 22K 91%

sissy joi

BBC JOI 221 (sub4all) HD 4m
Bbc 62K 97%

BBC JOI 221 (sub4all)

Katie - Cum like a sissy HD 10m
Joi 61K 98%

Katie - Cum like a sissy

Wavy hair babe Strap on Pov HD 8m
Strapon 40K 95%

Wavy hair babe Strap on Pov

Stepmom Tricks Stepson into Becoming Her Chastity Sissy HD 6m
Joi 69K 97%

Stepmom Tricks Stepson into Becoming Her Chastity Sissy

MJSissy - Be the sissy you are HD 5m
Hypno 48K 86%

MJSissy - Be the sissy you are

a_guide_to_sissication_beginner_am_i_a_sissy HD 23m
sissy training 59K 87%

a_guide_to_sissication_beginner_am_i_a_sissy

You Are A Sissy Whore HD 5m
Chaturbate 36K 93%

You Are A Sissy Whore

Magic Spell Sissy FUn 8m
pornhub 120K 89%

Magic Spell Sissy FUn

Be my sissy crossdresser, Mistress T HD 12m
Joi 180K 96%

Be my sissy crossdresser, Mistress T

Hot gay anal sex and cum HD 12m
Gay 93K 95%

Hot gay anal sex and cum

Yes mistress: Goddess Angel hypnotizes you 2 HD 15m
Hypnotized 69K 93%

Yes mistress: Goddess Angel hypnotizes you 2

C And D You Love Cock! 5m
faggot 2.3K 100%

C And D You Love Cock!

BBC JOI 256 (sub4all) 4m
Bbc 7.8K 92%

BBC JOI 256 (sub4all)

hehexdd HD 6m
faggot 1.1K 50%

hehexdd

LS Changing You 6m
faggot 14K 98%

LS Changing You

PF Dress Up And Suck Dick For Her 7m
faggot 22K 97%

PF Dress Up And Suck Dick For Her

Doctor Reveals To You That You Are Gay 8m
Gay 22K 98%

Doctor Reveals To You That You Are Gay

Fuck hard 11m
Gay 17K 92%

Fuck hard

MC No Closet For You 12m
Shemale 19K 89%

MC No Closet For You

Blonde Femdom Goddess Surprises You With Her Big Strapon 5m
Strapon 7.3K 92%

Blonde Femdom Goddess Surprises You With Her Big Strapon

PB Dicks In The News HD 6m
faggot 15K 99%

PB Dicks In The News

You are gay, just admit it 6m
Xvideos 20K 98%

You are gay, just admit it

Learn To Love Cock 15m
Blowjob 21K 95%

Learn To Love Cock

BBC JOI 353 (sub4all) 5m
Bbc 6.5K 88%

BBC JOI 353 (sub4all)

C You Are Gay! 7m
faggot 24K 98%

C You Are Gay!

BBC JOI 349 (sub4all) 2m
Bbc 9.2K 92%

BBC JOI 349 (sub4all)

BBC JOI 187 (sub4all) 12m
Bbc 18K 93%

BBC JOI 187 (sub4all)

BBC JOI 368 (sub4all) 28m
Bbc 22K 98%

BBC JOI 368 (sub4all)

Do you know what you want, sissy? HD 3m
Compilation 11K 85%

Do you know what you want, sissy?

joi34 HD 11m
Joi 14K 94%

joi34

PF You Suck Dick 6m
Chaturbate 55K 99%

PF You Suck Dick

perfect HD 24m
Kendra Lust 20K 98%

perfect

BBC JOI 213 (sub4all) HD 5m
Bbc 14K 97%

BBC JOI 213 (sub4all)

You like erections??? HD 16m
Chaturbate 25K 92%

You like erections???

Cravings for Dick HD HD 17m
Mind Control 28K 91%

Cravings for Dick HD

Humiliation faggot Cruel Girl Friend 13m
Sissy 11K 95%

Humiliation faggot Cruel Girl Friend

Faggot Trance HD 15m
Joi 83K 97%

Faggot Trance

sissy gay HD 6m
Sissy 46K 93%

sissy gay

jessica starling strapon HD 16m
POV 120K 98%

jessica starling strapon

stepmom pegging POV 4K 17m
Strapon 230K 96%

stepmom pegging POV

POV SUCK THIS STRAPON HD 4m
POV 25K 92%

POV SUCK THIS STRAPON

This GORGEOUS woman absolutely loves fisting some man ass 5m
Xvideos 5.1K 97%

This GORGEOUS woman absolutely loves fisting some man ass

This is how everyone should get themselves off HD 5m
Shemale 19K 100%

This is how everyone should get themselves off

Angelic 9m
Cei 61K 98%

Angelic

Sissy SPH HD 7m
Amateur 71K 97%

Sissy SPH

Faggot Cocksucker HD 17m
Blowjob 82K 95%

Faggot Cocksucker

Handjob by Molly HD 8m
Handjob 87K 98%

Handjob by Molly

WHores 22m
XHAMSTER 5.7K 91%

WHores

J es si ca S ta rl in g - CEI Punishment For Dirty Pervert JO I (check Description) HD 15m
Fetish 87K 98%

J es si ca S ta rl in g - CEI Punishment For Dirty Pervert JO I (check Description)

Think you're straight humiliation 12m
Joi 12K 83%

Think you're straight humiliation

Good Boys Eat 9m
Joi 57K 96%

Good Boys Eat

feminization (pantie+plug) 13m
POV 54K 95%

feminization (pantie+plug)

Blonde strapon JOI 9m
Strapon 5.8K 100%

Blonde strapon JOI

Ha ha Fag HD 6m
Handjob 67K 98%

Ha ha Fag

sissy bj joi 10m
Xvideos 14K 97%

sissy bj joi

Amanda Sph HD 7m
Joi 46K 97%

Amanda Sph

FEMDOM COMPILATION 3 HD 11m
Femdom 17K 82%

FEMDOM COMPILATION 3

Ellie Idol HD 15m
Ellie Idol 27K 97%

Ellie Idol

Not gay HD 18m
bongacams 7.1K 86%

Not gay

FootsieBabes Put a Toe Ring On It HD 10m
Footsie Babes 5.7K 100%

FootsieBabes Put a Toe Ring On It

Admit you are a faggot 11m
Joi 26K 94%

Admit you are a faggot

Buttplug Faggot Instructions HD 8m
BBW 27K 98%

Buttplug Faggot Instructions

BT sissy gangbang HD 7m
Sissy 43K 97%

BT sissy gangbang

Faggot Porn Audition HD 14m
Femdom 88K 99%

Faggot Porn Audition

PR Bisexual Mindfuck HD 15m
Joi 71K 97%

PR Bisexual Mindfuck

Bi Sex 2 HD 7m
Chaturbate 9.1K 81%

Bi Sex 2

British Brats puts you in chastity HD 6m
Mistress 44K 98%

British Brats puts you in chastity

hot white chick chastity POV 5+min HD 5m
POV 23K 97%

hot white chick chastity POV 5+min

Tiny cocks get locked HD 4m
Femdom 62K 90%

Tiny cocks get locked

Chastity hypno HD 32m
Handjob 250K 96%

Chastity hypno

Chastity hypno 2 HD 21m
Femdom 120K 94%

Chastity hypno 2

Learn to be a Cuckold HD 12m
Bbc 70K 95%

Learn to be a Cuckold

bi fantasies PR HD 2m
XHAMSTER 8.3K 92%

bi fantasies PR

From Cuck to Sissy HD 17m
Bbc 240K 92%

From Cuck to Sissy

Sissy Training 9m
Xnxx 31K 89%

Sissy Training

displaying 101 - 200 records in total 260
Watch later Favorite Playlist Report
Report this comment for review

Select your reason:

Report

Create new playlist:

Save

Add this to your playlists:

Your favorite videos

Watch later

Loading, please wait...
Missing your verification email?

Looks like you did not receive the verification email. Not to worry, we can send the link again.

English Español (América Latina) Español Português (Brasil) Português (Portugal) Français Deutsch Nederland Polski Türkçe Italiano Русский 日本語 Svenska हिन्दी ภาษาไทย Bahasa Melayu Bahasa Indonesia