Deswin was born in beautiful Jacksonville, Florida. She attended several schools there, graduating from Jean Ribault Senior High School. In 1999, Deswin had the fantastic opportunity to travel abroad with the Children’s International Summer Village (CISV) to Jönköping, Sweden, for six weeks. In high school, Deswin marched in the band on Clarinet, then later became a Majorette, was President of Nefeteria Social group, President of Band class for four years, member of the National Honor Society, Treasurer of the Student Government Association, Miss Ribault 1st Runner-Up
After graduating from high school, Deswin attended The Florida Agricultural & Mechanical University and earned her Bachelor's Degree in Elementary Education with Reading and ESOL endorsements. Some of her extracurriculars included being a member of the Incomparable Marching 100 playing Clarinet, being a part of the Alpha Epsilon Chapter of Sigma Gamma Rho Sorority, Inc. (Fall 2007), where she served as President for two years and Vice-President for one year, equipment manager for the Marching 100, coordinated activities of summer band camp, and was a member of the Beta Phi chapter of Tau Beta Sigma National Honorary Band Sorority, Inc. (Spring 2011) where I served as social activities director. She also held membership with the National Council for Negro Women.