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 cheerleader.
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, 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 several titles (listed below).
- Cheeky Cheerleader (Northern Spanking)
- Consequences for Cheaters (Cheerleader Spankings, 2019), Stevie Rose spanks Skylar (photos)
- Family Comes First (Cheerleader Spankings, 2020), Stevie Rose spanks cheerleader Skylar, photos
- Hot And Not Very Fun! (GoodSpanking), Chelsea Pfeiffer
- I Promise Not to Be a Disrespectful Brat (Stevie Rose's I Heart Spanking, 2019), Stevie Rose paddles Skylar
- Irresponsible Behavior (Stevie Rose's I Heart Spanking, 2019), Stevie Rose spanks Skylar
- Setting A Bad Example - Skylar Spanks Stevie For Drinking Too Much (Stevie Rose's I Heart Spanking, 2021), photos
- Severe Caning - Skylar Birthday Bruises (I Heart Spankings, 2019), Stevie Rose canes Skylar.
- She's All Wet (GoodSpanking), Chelsea Pfeiffer
- Skylar Spanked and Mouthsoaped By Daddy (Triple A Spanking), braids, photos
- Skylar Spanked For Slutty Shorts (Delco Video Productions, 2021), photos
- Skylar's Selfish Behavior (Stevie Rose's I Heart Spanking, 2019), Stevie Rose spanks Skylar
- Sneaky Slutty Sisters Spanked (Momma Spankings, 2020), Stevie Rose and Skylar punished in curfew story.
- Spanking Runs In The Family (GoodSpanking), 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
- Take Down Your Pants and Your Panties (GoodSpanking), Chelsea Pfeiffer, video at Spankbang
- Three Sisters Belt Whipped and Paddled Together (Stevie Rose's I Heart Spanking, 2019), Stevie, Veda, and Skylar Rose.
- Three Striped Roses: Skylar, Vada, and Stevie (Stevie Rose's I Heart Spanking, 2020), 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