Dean felt his breath catch. Leave it to Jo to ask the hard question, especially of him. She seemed to get him to tell her things he wouldn't tell others and in a way, he was comfortable with that. Hell, she was the first girl he didn't come on to so heavily.
Dean closed his eyes, remember how he 'wished' of those things. Experienced them and then hearing his mom's voice, when she was younger and telling him, she just wanted to be normal. He opened his eyes and there was a sadness in them as he looked down to her.
"Yes, I do miss it, but, I don't regret it. I don't regret this," he reached up to cup her cheek as well, his thumb gently caressing her cheek. He wished he had the answer, "Bad things happened to people like us. And ... being who we are, we don't want to see that happen to others. To see them suffer as we did. to have their hearts broken."
Dean got a distant look in his eyes, remembering how he now felt uneasy around his brother. He curled his hand around the back of her head, "Jo, I'm sorry about ... being such a jerk. I'm, I know what changed me," He slid his hand down her back and pushed her closer against him, "I need ... you, Jo. More than you know, I need you." And in more ways than just sex.