24 Matches Found

Jack 'N Jill 2  (1990)

  • Starring:  GypsyNikole RichieTitanic
  • Movie Synopsis:  From Nappy to shaved 'n' happy!!! There's nothing like a plump smooth black pussy!!! Sliding between those divine chocolate thighs and velvet crotch is like heaven on earth!!! This chocolate is guaran... Read more
  • Starring:  AndiDylanGypsySophie Strauss
  • Tag Line:  They broke up with their boyfriends, but lets see who gets the last laugh!

Naked Petgirls & Slavegirls  (2010)  Compilation

  • Starring:  CalypsoGypsyLillithSybil Hawthorne
  • Movie Synopsis:  Adorable Sybil Hawthorne and sexy Calypso are both trained as naked petgirls and kept in cages. They learn to act like puppies, eat and drink from bowls on the floor, and play with toys for rewards. C... Read more

Pain Sluts Of Shadowplayers 2  (2010)  Compilation

  • Starring:  GeitiaGypsyLeah LavadaMoonshineSkye
  • Movie Synopsis:  Four sultry submissive pain sluts are teased and tormented for your pleasure. Moonshine is suspended on a giant metal circle, her pierced pussy lips are weighted and stretched, and her nipples clampe... Read more
  • Starring:  Claire AdamsGypsyKittyPetraSadie Dawson
  • Movie Synopsis:  Sadie Dawson, Petra and Gypsy all have one thing in common...they're all eager Fillies ready to be tamed to the bit gag! They get their introduction to pony girl training in the wide open spaces of th... Read more

Pet Slave Girls  (2015)

  • Starring:  Claire AdamsGracie VegaGypsyKitten Petra
  • Movie Synopsis:  Gorgeous, fresh-faced Gracie Vega gets and introduction to bondage in this episode of Shadowplayers Punishment Sessions. Standing spread-eagled with a ball-gag in her mouth, her clothes are cut off, h... Read more
  • Starring:  Claire AdamsGypsyLillithPetra
  • Movie Synopsis:  Wearing the ultimate symbol of submission, a slave's nose ring, Lillith and Petra are presented for your pleasure. Lillith submits to Claire Adams and an ordeal of spanking, foot worship, vertical and... Read more
  • Starring:  Amy QuinnGypsyMike Mancini
  • Movie Synopsis:  Just another day in paradise for Mike as he dives into this delicious smorgasbord of big sexy asses. Amy and Gypsy stick their ripe and juicy rear ends up in the air and let him do whatever he wants. ... Read more
4.75 
  • Starring:  Amy QuinnGypsyHoney Butter
  • Movie Synopsis:  Amy loves being smothered in motherly love and these two mega MILFs are perfect for the job. They are literally twice her age and love taking her under their wing.
  • Starring:  GypsyJasminePrincess Pamela Payne
  • Movie Synopsis:  Once again allow Carter Stevens to take you inside the amazing world of Princess Pamela Payne, the internationally famous Queen of Dominance! Enter a world where the beautiful Mistress Rules over all.... Read more

Ponygirl Rodeo  (2012)

  • Starring:  GypsyKitten Mistress VendelaSadieSybil Hawthorne
  • Movie Synopsis:  Kitten is an adorable 19 year old cosplay fan who loves to dress up. Here she gets to play ponygirl and run through the woods pulling a wagon. She is harnessed up and fitted with bells on her nipples ... Read more
  • Starring:  FoxyGypsyLexi
  • Movie Synopsis:  Foxy, Gypsy and Lexi star in this jaw dropping gangbang adventure from Johnny Rebel Studios! The title of this movie is pretty spot - on. These three gals are greedy when it comes to fucking and getti... Read more
  • Starring:  GypsyLeah LavadaLivvySybil Hawthorne
  • Movie Synopsis:  Bound and Shackled Slave girls are put to work and punished outdoors and in. Busty beauty Sybil Hawthorne turns an outdoor pump handle while shackled naked and barefoot on the rocky ground. She pulls ... Read more
  • Starring:  Gypsy
  • Movie Synopsis:  You saw the first one... but nothing can prepare you for the hardcore fetish content of the follow-up. This video, which starts more or less where the last one left off, features the sexy, teen freak ... Read more