Over the course of a year, Vanessa went from being unable to take a dick in her ass to enthusiastically taking 15 dicks in her ass in one night. This compilation chronicles her journey on the pathway to becoming a wild anal whore, including double penetration, anonymous anal fucking, ass-to-mouth,
Hannah and Vanessa are sitting down to finalize the details of their divorce, and the emotions are tense. As the ink dries on the documents, they both realize simultaneously that the sudden sense of relief and freedom is a turn on that they had not expected. They immediately reconnect with
When Vanessa’s husband reveals his Christmas present, she’s initially confused, “What’s an Anal Hotwife Calendar?” Opening the first calendar window summons a sexy guy to the room. Eager and impatient, Vanessa opens the rest of the calendar all at once and soon the room is full of guys ready to
Professional masseuse Vanessa shows her client how much she appreciates a person who takes care of themselves by using all of her skills to take the best care of him. After a relaxing rub down Vanessa rims his ass before turning him over and treating his big cock to her
Flowers leads an exploration of the popular kink of cucking, seeking to debunk the false narratives and problematic undertones of the experience. After a conversation amongst a group of peers the couples pair off with tier third and start fucking, petting and kissing while the other watches it all before
Captain Picard was recently released from prison and is rediscovering sexuality after several years of mandated celibacy. Captain Picard’s friend, Vanessa, has looked forward to reconnecting with them and together they talk about what feels good and take it slowly. Early in the interaction, Captain Picard has to pause, flooded
In a first for Cliff Media, this scene features all masc-identifying people in a celebration of masculine energy and gay sex. Josiah is helping Josh set up a profile online in the hopes of finding connections with other masc guys. When Josiah discovers that Josh has set his filters to
During Vanessa’s “Yes Day” gangbangs, she enthusiastically consents to anything, as long as it’s in good spirits and a sex act porn sites will allow. In the second hour of “Yes Day” 2025, Vanessa is already a thoroughly used whore, entering glorious subspace, but still has enormous horny energy to
Huddling by her tent in the snow, Vanessa notices a lost and shivering hiker. She invites him over to get warm, shedding her clothes to soothe him with skin-to-skin contact. They end up fucking and the hiker’s kink side emerges as he rubs ice on her chest, so cold it
In the ultimate test of concentration, Vanessa interviews our gloryhole participants on both sides of the wall about relationships, sex positivity and their journey towards queer liberation. While sucking deep our kinky lovelies also dig deep, investigating truths and connecting closer and closer through sex and vulnerability.
At a model UN conference the teacher gets turned on and decides to send a few spicy pictures to some of the students in her class. It proves too much to resist and pretty soon she and her star pupils get into each other on the hotel bed. After a
Vanessa used to hold back, stopping herself when she thought she might cum hard enough to squirt. Eventually, she decided life is too short to have anything less than full, real orgasms and vulnerable sex, even – perhaps especially if – it’s dirty, perverted or taboo. These days she lets
The first time Cliff Media ever hosted a live porn workshop at Hawks PDX bathhouse! An audience lounging on the bathhouse patio came up with the wackiest ideas for scenes that launched the Cliff Media team into hysterics, creativity and, of course, orgy. Thanks to audience participation for held the
In this true-to-life scene, B.T. is preparing to direct an 80s-style class called “Toppercize”, reimagining the Jazzercise-style in topping with dick and dildo. Despite a strong personal interest in topping, B.T. had not yet had the opportunity to put her imagination to the test, so Kitty and Vanessa volunteered as
It’s speed dating, but slutty queer style! Our participants answer steamy questions in one lightning round after another gradually shedding their clothes with each response. Enjoy healthy, direct communication about wants and desires as the sexual tension builds and our enthusiastic announcer brings everyone closer and closer to an all
When Vanessa accidentally walks in on her housemate showering, she apologizes but can’t help but notice how hot he is. She asks if she can kiss him and suck his dick. They end up fucking against the shower wall, with his dick deep inside her and her crying out in
Steph leads a group of friends in a session of mutual masturbation as a form of therapy. They learn to celebrate themselves through explorative touch, rubbing and fingering their way to glorious orgasms until eventually things heat up to the point where they can’t help themselves and start to stroke,
The fabulous Whoreable stars in her very first scene with Cliff Media. After meeting her costars Roxie and Foxie they have a conversation about feeling nervous, how to ask for what you want and the beauty of enthusiastic consent. Foxie and Roxie start slowly, caressing Whoreable’s legs and tits before
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