toby

Middle child (Tanya — older sis, and Tristin — younger sister).  Mother and little sis have bipolar disorder.  Father was emotionally absent from the home, and a compulsive gambler.  While Tanya helped out financially and with responsibilities as they got older, Toby focused on playing caregiver and peacemaker.  Guilt became his secret weapon.  Taught himself behavior modification techniques and studied a lot of psychology.

College at Columbia University.  Partied hard and formed a gambling addiction.  Still passed with all A's.  Was in a serious relationship during that time but fucked it up because of the addiction.  

After college, felt broken because of the relationship, and just wanted to have fun.  A few hott girls he knew were joining the peace corps, so he decided to do the same.  He worked building and setting up a medical clinic in rural Paraguay.  

Toby met Molly & Gabe in 2011 at a spanking party, only a few months after he returned from the Peace Corps.  Toby had an instant connection with Molly, attracted to her friendly disposition, sincerity, and intelligence.  They kept in touch, but since Gabe was her main spanker, it was more like vanilla friends.

When Violet had legal trouble, Molly called Toby to help.  Since Molly was also taking a break from Violet, it kind of left her with no one.  Toby and Violet gravitated towards each other because of similar backgrounds (both from nyc, financial struggles, rough family environment).  Toby also admired Violet's resilience.  

The clear chemistry encourages Violet to ask Toby to be her spanker.  He's hesitant, but since the case is almost over, agrees.  They have a great dynamic, he's able to help her prioritize her mental health.  

However, he eventually gets really busy with school and work, unable to provide her with as much attention.  As a result, Violet starts acting out, and eventually he breaks off their relationship.