In the season opener of Top Flight Security, lovable slacker Tre (JD Witherspoon) is forced off the couch and into the job force when his girlfriend Nicole (Antoinette Mia Pettis) issues him an ultimatum. He lands a job at Top Flight Security of America where he is taken under the questionable wings of Officer Steve (James Gill).
Tre meets his co-worker Sherry, Oscar and Aabheer and the new recruits of Top Flight Security are put through a rigorous training program. Tre finds himself tested in the most violating of manners.
The officers of Top Flight begin to get the lay of the land while enforcing their duties. Personal proclivities almost land Oscar and Sherry in hot water while Tre finds himself led on a chase by a trouble making transient who has taken to lurking around the apartment complex.
A gift from an appreciative resident has unintended consequences for both Tre and Nicole which culminates in them having a very long night at the hospital.
Tre's attempt to take Nicole out for a romantic evening goes terribly wrong as their date becomes an obstacle course of unfortunate events.
Nicole breaks up with Tre and he turns to his co-workers for advice and support. Each member of the team attempts to offer comfort and wisdom in their own misguided way; which just make matters worse in the end.
A sexy female detective comes to investigate a suspicious crime at the offices of Top Flight Security and each member must establish an alibi for their where about at the time of the incident.
Aabheer loses his pants and Sherry finds a ring that she mistakenly assumes is for her. The team closes in on the transient who has been making their jobs and lives miserable.
The officers of Top Flight Security finally capture and bring in the transient known to them all as the "Troublemaker". But he reveals a secret to Officer Steve that causes him to release him much to the chagrin of the team whom he has plagued and harassed.
Aabheer is concerned when Officer Steve goes missing and launches a search. Meanwhile Tre tries to find a way to gently let Sherry know that his heart belongs to Nicole - and somehow survive the aftermath.
After an exhaustive search the team finally locates and rescues Officer Steve. Traumatized after his ordeal the team remains by his side for moral support causing Tre to be late for his last chance date with Nicole. He catches her as she is about to leave the restaurant and proposes but... he might just be too late.