New Videos from Mommyruby

Mistress Ruby Pegs Her Leaking Chastity Slut
Mistress Ruby Pegs Her Leaking Chastity Slut
Inverted Chastity Cage CBT: 5 Minute Ballbusting & Vibe Torment
Inverted Chastity Cage CBT: 5 Minute Ballbusting & Vibe Torment
Mommy Fingers and Pegs Her Little Latex Toy
Mommy Fingers and Pegs Her Little Latex Toy
Balcony Pegging: Chastity Pup Eats His Own Leakage While Mistress Ruby Destroys His Hole
Balcony Pegging: Chastity Pup Eats His Own Leakage While Mistress Ruby Destroys His Hole
Gay Cock Sucking Training JOI: Accept You're a Cum-Hungry Faggot & Suck Like a Pro
Gay Cock Sucking Training JOI: Accept You're a Cum-Hungry Faggot & Suck Like a Pro
Nurse Ruby’s Aroma Treatment – Small Dick Reprogramming Session
Nurse Ruby’s Aroma Treatment – Small Dick Reprogramming Session
Cage-Grind: Your Release Is Still Forbidden
Cage-Grind: Your Release Is Still Forbidden
Gay Cock Addiction Reprogramming – Accept You’re a Cum Hungry Faggot
Gay Cock Addiction Reprogramming – Accept You’re a Cum Hungry Faggot
Sissy Training Lesson 2 – Feminine Body Ritual & First Orgasm Assignment
Sissy Training Lesson 2 – Feminine Body Ritual & First Orgasm Assignment
Mommy's Pathetic Gooner Edging Denial – No Cum, Just Endless Stroke & Worship
Mommy's Pathetic Gooner Edging Denial – No Cum, Just Endless Stroke & Worship
The Date From Hell – Black mail, SPH & Chastity Takeover (JOI + CEI)
The Date From Hell – Black mail, SPH & Chastity Takeover (JOI + CEI)
Sissy Slave Training – Week 1: Accept Your Fate for Miss Ruby
Sissy Slave Training – Week 1: Accept Your Fate for Miss Ruby
Hello Kitty Goon Training – Edge for Mommy, No Cum Allowed
Hello Kitty Goon Training – Edge for Mommy, No Cum Allowed
Cum-Eating JOI: Stroke, Beg, Swallow for Miss Ruby
Cum-Eating JOI: Stroke, Beg, Swallow for Miss Ruby
Caged, Desperate & Used: A Loser’s Lesson in Real Cock
Caged, Desperate & Used: A Loser’s Lesson in Real Cock
Small Dick Loser Brainwashing: Repeat-After-Me SPH Conditioning
Small Dick Loser Brainwashing: Repeat-After-Me SPH Conditioning
Sissy Brain wash Loop – I’m Nothing but Miss Ruby’s Hole
Sissy Brain wash Loop – I’m Nothing but Miss Ruby’s Hole
Chastity Brainwashing: Miss Ruby Rewires Your Pathetic Little Cock
Chastity Brainwashing: Miss Ruby Rewires Your Pathetic Little Cock
Locked Loser vs BBC: Mommy’s Creamed Pussy Humiliation for Tiny Chastity Dicks
Locked Loser vs BBC: Mommy’s Creamed Pussy Humiliation for Tiny Chastity Dicks
Waking Up Needing to Go And Finally Being Able To
Waking Up Needing to Go And Finally Being Able To
Strained Stuck A Very Real Bathroom Struggle
Strained Stuck A Very Real Bathroom Struggle
Aroma Obedience Conditioning – Goon & Edge Training for Good Boys
Aroma Obedience Conditioning – Goon & Edge Training for Good Boys
Strap-On Mirror Fuck – Humiliated Sissy Training in Matching Underwear
Strap-On Mirror Fuck – Humiliated Sissy Training in Matching Underwear
Constipated Goth Mommy: 4 Minutes of Painful Plops, Agonizing Groans and Toilet Torment
Constipated Goth Mommy: 4 Minutes of Painful Plops, Agonizing Groans and Toilet Torment