Though if i were to psychoanalyze Barry a little i'd say along with his insistent drinking & berating on others that he's more submissive than anything. He probably yearns for a woman to be more long the lines of a mommy to him, he would love nothing more than to crawl into his girls arms to be held with whispers of love serenating his ears. I see him being an occasional switch which is where the pegging would come into place, more of a once in a blue moon sort of thing for him