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First Time Is The Hardest

First Time Is The Hardest

The Beauty Of Painal

The Beauty Of Painal

Looks Dry

Looks Dry

Pain Or Pleasure?

Pain Or Pleasure?

Bound, Now With Working Source(In Comments)

Bound, Now With Working Source(In Comments)

Screaming!

Screaming!

She Feels An Extremely Sharp Pain In Her Anus

She Feels An Extremely Sharp Pain In Her Anus

Stop Complaining, I Won't Take Take Longer Than 45 Minutes Tops

Stop Complaining, I Won't Take Take Longer Than 45 Minutes Tops

Tears Rolling From Anal Insertion.

Tears Rolling From Anal Insertion.

This Hurts A Little Bit

This Hurts A Little Bit

Why Isnt This Here Yet?

Why Isnt This Here Yet?

Someones Having A Good Time

Someones Having A Good Time

That Face!

That Face!

Source Needed...she Doesn't Look Like She's Liking It...

Source Needed...she Doesn't Look Like She's Liking It...

Ouch

Ouch

Take A Deep Breath

Take A Deep Breath

Wrong Angle - Source?

Wrong Angle - Source?

Eyes Wide Open

Eyes Wide Open

&Amp;Quot;Take It Slow... Ahhhh&Amp;Quot;

&Amp;Quot;Take It Slow... Ahhhh&Amp;Quot;

Screaming

Screaming

Fishnets And Pain [X-Post From /R/Masterofanal]

Fishnets And Pain [X-Post From /R/Masterofanal]

She Has Learned An Important Lesson Early In Life.... Resistance Is Futile

She Has Learned An Important Lesson Early In Life.... Resistance Is Futile

Such A Lovely Face.

Such A Lovely Face.

The Face Says It All [Gif]

The Face Says It All [Gif]

Holding Her Down

Holding Her Down

Carolina Greco Painal

Carolina Greco Painal

One Of The Hottest Painal Gifs Ive Ever Seen. This Type Of First Entry Is The Stuff Of My Fantasies. Anyone Got A Source?

One Of The Hottest Painal Gifs Ive Ever Seen. This Type Of First Entry Is The Stuff ...

What Is This From?

What Is This From?

A Pain In Her Ass

A Pain In Her Ass

Anal Jackhammer

Anal Jackhammer

To Deep

To Deep

Ass Destruction

Ass Destruction

Stop Little Bit

Stop Little Bit

Wincing

Wincing

Pain + Anal = Painal

Pain + Anal = Painal

Violet Monroe

Violet Monroe

Easily The Best Thing I've Seen All Day.

Easily The Best Thing I've Seen All Day.

Looks Painful

Looks Painful

Sidefuck

Sidefuck

Oh Myyyy!

Oh Myyyy!

Lily Carter Wincing

Lily Carter Wincing

Bella Rossi And Yhivi

Bella Rossi And Yhivi

&Amp;Quot;That Really Hurts!&Amp;Quot; - Kimberly Costa

&Amp;Quot;That Really Hurts!&Amp;Quot; - Kimberly Costa

Whats Better? Reading Her Lips Or The Look On Her Face?

Whats Better? Reading Her Lips Or The Look On Her Face?

Can Someone Help Me Find The Full Vid?

Can Someone Help Me Find The Full Vid?

Doing It Wrong Can Be Soo Right

Doing It Wrong Can Be Soo Right

That's Right....take It...

That's Right....take It...

Does Anyone Know Where This Is From?

Does Anyone Know Where This Is From?

This Subreddit Needs More Gifs

This Subreddit Needs More Gifs

This Seems To Be Painful

This Seems To Be Painful

He Won't Stop

He Won't Stop

Lily Monsters Of Cock

Lily Monsters Of Cock

The Classic Anal Full Nelson

The Classic Anal Full Nelson

Nice And Big

Nice And Big

Painful Anal With Her Feet Up - Devyn Cole

Painful Anal With Her Feet Up - Devyn Cole

Does This Qualify?

Does This Qualify?

Owww...

Owww...

Follow Up On A Kinky Easter With My Girlfriend: Pics Of The Anal Hook And How She Was Made Helpless Before I Fucked Her

Follow Up On A Kinky Easter With My Girlfriend: Pics Of The Anal Hook And How She ...

Backroom Casting Couch Blonde Takes It Up The Ass Hard!

Backroom Casting Couch Blonde Takes It Up The Ass Hard!

Source?

Source?