Jimmy's past is quite tragic. The soft spoken boy was enslaved by the Legion at the age of 16. His parents were killed as an example and Jimmy wound up as the tent servant of a high ranking centurion. His master turned out to be infatuated with the young Jimmy and protected him. He was kind and gentle most of the time, tending to the secret affair (as homosexuality is punishable by death in the Legion proper) and gifting Jimmy small things. However, as with all good things, this did not last.
The centurion's affair was nearly uncovered, and rumors began to circulate. The centurion decided to eliminate Jimmy as the only bit of evidence against him. He took him out to the desert, but Jimmy knew what was going to happen. He kicked his lover in the groin and ran. He was not pursued. After a long flight, he came to Westside and signed up with Pretty Sarah. By the time the Courier meets him, Jimmy has been working for Sarah for six months. He isn't particularly keen on Casa or the landlord, but Sarah's fairness keeps him on board.
Interactions with the player character
This character is a pimp or prostitute and sells sex.
Although Jimmy has a Confirmed Bachelor dialogue option, it doesn't actually do anything beyond granting experience.
"It's tough on both sides of the fence, really. I think women have it worse. They're like money, given as rewards. Breeding stock. Honestly, as long as men meet obligations and the child count, "friendships" are a sight more equal than the level of most Legion husbands and wives."
"Baby, who I am doesn't matter. I'll be anybody you need me to be. It's better that way, you'll see."
"I'm just a fantasy come to life. But you already knew that."
"Sorry, ma'am, but ain't enough caps in all of New Vegas to make me do that. Nuh-uh."
"I told you, I ain't ever doing that again - ever. It was like being a slave all over again."
"Hey, mister, looking to relax? Looks like you carry a lot of tension in your shoulders... and upper thighs."
"Sorry, ma'am, but my services are "members only," all right? You might try Sweetie."
↑ 1.01.1The Courier: "I hear you were a slave of Caesar's Legion. " Jimmy: "What Marco said is true. The Legion attacked my village when I was 16. My parents were killed as examples. The rest of us, chained and dragged to some kind of camp. A Centurion there chose me as his tent servant. He was handsome, and gentle, most of the time. Said it was our secret, and he'd protect me. Gave me little gifts, stupid things. But Caesar punishes homosexuality with death, and we nearly got caught, and there were suspicions. So when he took me out into the desert... Well, I knew he was going to get rid of me. So I kicked him where it counts and I ran. And then swam. And ran some more. Wound up here." (Jimmy's dialogue (Fallout: New Vegas))
↑The Courier: "Been working here long?" Jimmy: "Half a year or so. The Casa's a dump and Marco's a pig, but Pretty Sarah makes sure I don't get hassled. I don't get as many customers as Sweetie or Maude. But the customers I do get always come back." (Jimmy's dialogue (Fallout: New Vegas))