"Crossdressing encouragement" About 16,568 Videos

Dressing You Up A Little A Total Sissy Slut thumbnail
2min

Dressing You Up A Little A Total Sissy Slut

You Really Need To Improve Your Cock Sucking Skills Joi thumbnail
7min

You Really Need To Improve Your Cock Sucking Skills Joi

You Can't Be A Sissy Boy With Knowing How To Suck Cock thumbnail
7min

You Can't Be A Sissy Boy With Knowing How To Suck Cock

These New Knee High Socks Will Make You So Hard Joi thumbnail
10min

These New Knee High Socks Will Make You So Hard Joi

Beg For A Big Cock Like A Good Little Sissy Boy thumbnail
9min

Beg For A Big Cock Like A Good Little Sissy Boy

You Can Watch While He Makes Me Cum thumbnail
8min

You Can Watch While He Makes Me Cum

Tonight I Will Make You Into One Of The Girls thumbnail
5min

Tonight I Will Make You Into One Of The Girls

You Are Going To Look Hot As A Pretty Little Princess thumbnail
6min

You Are Going To Look Hot As A Pretty Little Princess

I'll Teach You To Take A Cock Like A Real Sissy thumbnail
11min

I'll Teach You To Take A Cock Like A Real Sissy

Sinstress Takes A Smoke Break With Her Sissy Slave thumbnail
6min

Sinstress Takes A Smoke Break With Her Sissy Slave

I Will Tell You How I Want You To Jerk It Joi thumbnail
8min

I Will Tell You How I Want You To Jerk It Joi

I Know That You Are Secretly A Sissy Boy thumbnail
5min

I Know That You Are Secretly A Sissy Boy

I Can't Wait To See You Dresses As A thumbnail
5min

I Can't Wait To See You Dresses As A

I Have A Cute Little Sissy Dress That Might Fit You thumbnail
9min

I Have A Cute Little Sissy Dress That Might Fit You

I Have A Cute Little Outfit For You thumbnail
5min

I Have A Cute Little Outfit For You

Mistress Takes You To A Gay Bar thumbnail
11min

Mistress Takes You To A Gay Bar

It's Sexy When You Wear Panties thumbnail
9min

It's Sexy When You Wear Panties

I Found Your Stash Of Women's Panties thumbnail
6min

I Found Your Stash Of Women's Panties

Fantasize About Sucking Cock While I Smoke thumbnail
8min

Fantasize About Sucking Cock While I Smoke

I Love Being A Cock Hungry Sissy Boy thumbnail
11min

I Love Being A Cock Hungry Sissy Boy

A Sissy Bitch Like You Should Wear Some Cute Panties thumbnail
7min

A Sissy Bitch Like You Should Wear Some Cute Panties

You're Just A Pretty Little Princess Aren't You thumbnail
4min

You're Just A Pretty Little Princess Aren't You

I Know You Have Been Hiding Your Sissy Desires thumbnail
5min

I Know You Have Been Hiding Your Sissy Desires

I'll Give You A Total Sissy Boy Makeover thumbnail
4min

I'll Give You A Total Sissy Boy Makeover

I Want You To Smoke A Cig With Me thumbnail
5min

I Want You To Smoke A Cig With Me

You Need To Learn How To Worship A Big Hard Cock thumbnail
7min

You Need To Learn How To Worship A Big Hard Cock

I Have A Hot New Set Of Lingerie For You thumbnail
5min

I Have A Hot New Set Of Lingerie For You

Think You Have What It Takes To Be A Sissy Boy thumbnail
7min

Think You Have What It Takes To Be A Sissy Boy

I Need Your Complete Submission And Total Obedience thumbnail
7min

I Need Your Complete Submission And Total Obedience

I Know You Have Been Hiding Your Sissy Desires thumbnail
7min

I Know You Have Been Hiding Your Sissy Desires

I Can Teach You To Suck Cock Like A Real Slut thumbnail
11min

I Can Teach You To Suck Cock Like A Real Slut

This Cute Little Outfit Is Going To Make You Look Hot thumbnail
7min

This Cute Little Outfit Is Going To Make You Look Hot

My New Micro Thong Barely Even Covers My Pussy Joi thumbnail
6min

My New Micro Thong Barely Even Covers My Pussy Joi

Let's Stretch Out Your Ass Before You Get Fucked For Real thumbnail
5min

Let's Stretch Out Your Ass Before You Get Fucked For Real

These Silk Panties Will Feel Amazing Against Your Cock thumbnail
5min

These Silk Panties Will Feel Amazing Against Your Cock

You're Not Man Enough For Me thumbnail
11min

You're Not Man Enough For Me


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