CuckoldSessions


Ivy Winters

Ivy Winters @ CuckoldSessions.com Being a cuckold isn’t a part time deal; it’s a lifestyle for this older submissive gentleman. There’s nothing this subhuman won’t do for his wife and Dr. Ivy Winters is trying to get inside his head. The male chastity belt and his willingness to watch his […]


Hydii May

Hydii May @ CuckoldSessions.com Chip and his lady, Hydii May, are about to welcome a bundle of joy into the world. Chip has had a difficult time figuring out how to show appreciation for the mother of his unborn child. A stroller? Already have one. Diapers? They’re up to their […]


Veruca James

Veruca James @ CuckoldSessions.com Never sent a white boy to do a black man’s job: Pleasuring white women. Lexington Steele is consulting Veruca James and her boyfriend Wade. Veruca loves her man but he can’ offer her what she really needs- a goof hardcore fucking. Wade is packing as much […]


Amirah Adara

Amirah Adara @ CuckoldSessions.com We get a lot of e-mails from cucks all over the world wanting to partake in a session for the site. Recently, we had an issue with a cuck calling himself “Osiris”. He’s sent many, many e-mails requesting a session with our Number 1 Bull, Shane […]


Alice Green

Alice Green @ CuckoldSessions.com We’re bringing you something completely out of left field with this update. You see, Alice Green’s ACTUAL boyfriend is a certified cuckold and he’s totally fine with that role. In fact, Alice mocks his, um, shortcomings on and off camera. Ladies and gentlemen…..this is gonna prove […]


Mia Rider

Mia Rider @ CuckoldSessions.com Mia Rider’s fairly new to the cuckold game but she has an amazing instructor in Shane Diesel. Shane is the supreme master of humiliating white boys to the brink of near suicide on their part. Mia offers up her Asian ass for a private lesson in […]


Lola Foxx

Lola Foxx @ CuckoldSessions.com The following encounter is further proof that white people are a completely different breed. Lola Foxx and her boyfriend are enjoying a sunny afternoon in the park. What Lola doesn’t know is that her guy wants her to fuck his friend Charlie Mac. Lola’s not into […]


Valentina Nappi

Valentina Nappi @ CuckoldSessions.com Valentina Nappi is a foreign exchange student whose being hosted by Kade and his family. Kade is quick to discover that Valentina is fucking her African-American Studies professor, much to the dismay of Kade. We find Professor Diesel in his study as Kade barges in and […]