Starting around 2018, Skylar began playing spankee roles in videos featuring F/F and M/F scenarios. She has long brown hair occasionally worn in braids for a more innocent, schoolgirl look. She has also appeared as a blonde in several videos and has most recently dyed her hair bright red.
Rose has performed in videos by several major spanking video producers including Chelsea Pfeiffer Entertainment (GoodSpanking), Cheerleader Spankings, Momma Spankings, Triple A Spanking, Northern Spanking, PunishmentsOnly, Assume the Position Studios (ATP Studios), and her sister's company, Stevie Rose's I Heart Spankings (website).
She has also been punished with and by her sister Stevie Rose in many of the titles listed below.
- The Accidental Spanking (ATP Studios, 2021), Stevie Rose spanks Skylar, photos
- Birthday Bruising - Skylar Rose, Part 1 (I Heart Spanking, 2021), Stevie Rose spanks Skylar, birthday spanking, photos
- Cheeky Cheerleader (Northern Spanking), Paul Kennedy, cheerleader, photos
- Cheer Camp, Year Four: The Spankings (Cheerleader Spankings, 2021), Cleo Divine, Cara Day, Kiki Cali, Rachel Adams, photos
- Family Comes First (Cheerleader Spankings, 2020), Stevie Rose spanks cheerleader Skylar, photos
- Final Strokes - Birthday Bruises For Skylar (I Heart Spanking, 2021), Stevie Rose spanks Skylar, photos
- I Promise Not to Be a Disrespectful Brat (I Heart Spanking, 2019), Stevie Rose paddles brat Skylar, photos
- Irresponsible Behavior (I Heart Spanking, 2019), Stevie Rose spanks Skylar, photos
- Kay Rose's Misplaced Spanks with Stevie and Skylar Rose (I Heart Spankings, 2022), stepmother Kay Rose, Stevie Rose (photos)
- Lingerie Spanking Skylar Rose: Worth the Drive (ATP Studios, 2022), photos
- Setting a Bad Example - Skylar Spanks Stevie For Drinking Too Much (I Heart Spanking, 2021), photos
- Setting a Better Example 2 - Skylar Rose Paddles Stevie Rose (I Heart Spanking, 2021), paddling, photos
- Severe Caning - Skylar Birthday Bruises (I Heart Spanking, 2019), Stevie Rose canes Skylar.
- She's All Wet (GoodSpanking), Chelsea Pfeiffer
- Skylar Learns Respect (Cheerleader Spankings, 2023), coach Stevie Rose gives Skylar a strapping, respect, photos
- Skylar Spanked and Mouthsoaped By Daddy (Triple A Spanking), braids, photos, video at SpankBang
- Skylar Spanked For Slutty Shorts (Delco Video Productions, 2021), photos
- Skylar's Selfish Behavior (I Heart Spanking, 2019), Stevie Rose spanks Skylar
- Sneaky Slutty Sisters Spanked (Momma Spankings, 2020), Stevie Rose and Skylar punished in curfew story.
- Stepsister Boundaries: Borrowed Clothes - Stevie Spanks Skylar Rose (Worst Behavior Productions, 2023), photos
- Stevie Gets Her (Actual) Sister Spanked (Loren Punishments/PunishmentsOnly, 2018), Stevie Rose and Skylar both get punished (photos, video).
- Stevie and Skylar Caught Selling Contraband (Delvo Video Productions), Stevie, Skylar and Veda Rose (video)
- Stevie Spanks Skylar (Sarah Gregory Spanking, 2020), photos
- Stop Cheering, Start Cleaning (Cheerleader Spankings, 2019), as a blonde cheerleader, kitchen, bar stool, photos
- Teen Skylar: Severe Bare Cane Welts (Assume the Position Studios, 2022), photos
- Three Sisters Belt Whipped and Paddled Together (I Heart Spanking, 2019), Stevie, Veda, and Skylar Rose.
- Three Striped Roses: Skylar, Vada, and Stevie (I Heart Spanking, 2020), photos
- Too Big for Her Britches (ATP Studios, 2021), Stevie Rose, photos
- Too Big for Her Britches 2 (ATP Studios, 2021), Stevie Rose spanks Skylar, video
- Too Big for Her Britches 3: Stevie and Skylar Held in Place for Bare Bottom Discipline (ATP Studios, 2021), photos
- Trick or Treat Shenanigans - Stevie Rose and Skylar Rose Spanked by the Neighbor (I Heart Spanking, 2020), Stevie Rose, photos
- What Happens To Naughty Girls (Momma Spankings, 2019), braids, photos, video on SpankBang
- What Would Mom Do? (Northern Spanking, c. 2020), Stevie spanks Skylar, photos