"deeper" 290

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Deeper - Cecelia Taylor

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Cecelia Taylor - Golden Key
Released: March 14, 2024

Cecelia's employer might be a modern day Bluebeard, but this blonde always lets curiosity get the better of her, punishment be damned.

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Deeper - Anna Claire Clouds

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Anna Claire Clouds - Before The Guests Arrive
Released: March 21, 2024

A young wife's dinner party prep is thrown off schedule when an unexpected guest arrives early.

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Deeper - Go Deeper With Maitland Compilation

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Ivy Lebelle, Bree Daniels, Maitland Ward & Riley Reid - Go Deeper With Maitland Compilation
Released: May 21, 2020

Presented by DEEPER. Go even Deeper with the best of Maitland Ward. This compilation includes Maitland's award-winning performance, with Ivy Lebelle, in the Deeper 5-part series Drive. As well as the twisted tale "Secretary" with Riley Reid and "Higher Power". Also featuring Maitland's iconic debut performance in Blacked's "Unprofessional" and "We all do it, too" co-starring Bree Daniels.

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Deeper - Willow Ryder

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Willow Ryder - Beggar
Released: February 29, 2024

A sugar baby keeps her benefactor boyfriend putting in overtime to afford the lifestyle she desires, so he decides to make her work to uphold her end of the bargain. The task he has in mind she'll have to accomplish down on all-fours.

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Deeper - Braylin Bailey

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Braylin Bailey - Green Earrings
Released: March 7, 2024

A sugar baby doesn't want her benefactor going easy on her just because it's her first time.

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Deeper - Skye Blue

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Skye Blue - It's Not Over
Released: November 29, 2022

As a man tries to break out of a relationship ruled by his spoiled girlfriend's pussy, she reminds him again why it's gone on this long already.

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Deeper - Intimates Series - New 2021 Updates

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Avi Love - Intimates Series
Adria Rae - Intimates Series
Maitland Ward - Intimate Series

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Deeper - Adria Rae

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Adria Rae - Going Deeper
Released: April 19, 2019

The touch of his hand is all that is required for Adria to desire him enough to try something he truly wants. She is an open book to him and he can read her perfectly. She wants more than she has ever experienced and she is about to be fully filled - as deep as she can take it.

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Deeper - The Art Of Cuck Compilation

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Janice Griffith, Liv Wild, Karla Kush, Evelin Stone & Lacy Lennon - The Art Of Cuck
Released: June 7, 2020

Presented by DEEPER. A compilation of the sexiest cuckold content you will find. Beautiful girls experience kinky acts while their cuckold watches on.

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Deeper - Adriana Chechik

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Adriana Chechik - Earned It Part 1
Released: February 23, 2020

She has watched him from afar for some time, training herself until she is now finally ready for him. All she wants now is for him to test her - to see just how much she can take.

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Deeper - Riley Steele

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Riley Steele - Do You Want
Released: February 28, 2020

Riley's sudden opposition to him throws Aaron into a heated emotional reaction until he realizes that's exactly what she was going for. Heated, reactionary sex ensues. Written and directed by Stoya.

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Deeper - Demi Sutra, Ana Foxxx, Scarlit Scandal & Nia Nacci

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Demi Sutra, Ana Foxxx, Scarlit Scandal & Nia Nacci - Taste
Released: March 4, 2020

What do you get for the man who has everything? On Valentine's day, she knows exactly what he craves above all else - she knows his taste.

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Deeper - Morgan Lee & Adriana Chechik

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Morgan Lee & Adriana Chechik - Earned It Part 2
Released: March 9, 2020

His first conquest went entirely to plan, ensuring every satisfaction and taboo was completed. Now he has the option to take whatever he wants from her - but he's bringing company, and she has to watch.

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Deeper - Rae Lil Black

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Rae Lil Black - I'm Not Leaving
Released: March 14, 2020

She's got his attention one way or another but he's not alone for long. He tells her it's not a game, but she has other ideas - she wants what she came for and she's not leaving.

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Deeper - LaSirena69 & Maitland Ward

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LaSirena69 & Maitland Ward - Compersion
Released: February 8, 2020

Maitland wants everything for her lover, including the penis that she can't naturally provide. Everyone agrees on the safeword and the caveat is that Maitland can document the evening with her camera. Written and directed by Stoya.

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Deeper - Riley Reid & Maitland Ward

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Riley Reid & Maitland Ward - Secretary
Released: March 19, 2020

Interviews are always something to heighten the nerves, and this one is no exception. Riley's interest in the company is inspired, but this introduction to the organisation is a real eye opener.

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