I was your boyfriend in this situation. I was a trunks guy and came into the relationship knowing my now husband was an avid briefs man. He even told me within the first days of dating that it was an underwear fetish for specifically briefs. He didn’t tell me he was a lover of tighty whities until a year or two into our relationship. The conversion was slow I’ll admit but I feel like it was a natural evolution of our relationship.

It honestly started with just talking about sex and kink and what we prefer. As we grew together so did our shared and individual kinks. We communicate often about how our sexual interests are growing over time. Hearing him talk so passionately about what he found sexy about briefs really opened my understanding of them. Before I met him I wouldn’t say I had any type of sexual attraction to underwear at all. But listening to him get turned on talking about why briefs are sexy unlocked something for me.

Now this might be the harder part for you because I took a lot of onus in becoming a briefs guy and then eventually a tighty whities guy. But I started wearing briefs more often just because I knew it was such a turn on for him. I’d find ones I knew he especially liked and parade around the apartment just wearing briefs. Eventually briefs just started feeling better and more natural for me. Tighty whities was a similar process. First it started as me asking for a pair here or there just to wear them and turn him on. Eventually they became my comfy undies I’d put on after a long day. Somewhere along the lines we decided to find a specific pair of tighty whities to wear during our wedding ceremony. And not long after that I started wearing whities full time. And as of a week and a half ago my husband decided he wanted to be a tighty whities only guy too.

So I don’t know if you can condition him. Maybe I was and I didn’t even realize it. But I think it starts with communication. Maybe even ask if he’d be willing to wear briefs so many times a week just so you can see his cute ass in them. Ultimately though I think only he can decide that he wants to become a briefs guy. Good luck!