I had a similar situation. I wear boxers only around my house. Had a good friend visiting for a week and he is the most sexually up-tight guy I've ever known. Will not allow any talk about sex and gets upset if I text him pics that have anything to do with a dick. Usually, he will not text me for an 8 day punishment period. As he says, "porn on your own".

On the second night of his visit, I just walked out in boxers after my shower, expecting him to make me wear more clothes. But he did not and seemed to be comfortable with the way I was dressed. I was shocked.

Next morning, I made coffee in my boxers and we sat in the family room. He sat on the sofa and I was in a chair directly across from him. From time to time, I spread my legs and made sure my dick would poke out from the boxers on a regular basis. He kept talking like nothing was happening I could not believe it.

From that time, boxers were totally accepted and I kept the fly pulled open and my dick regularly poked out over the next day or so. He did not say anything and I knew he was going to let me do this without criticism. So I gave him plenty of dick pokes out of my boxers for the next several days.

On the last day of his visit, we stood in the kitchen across from each other and had our morning coffee. We had generic conversation while I placed my hand on my dick and very slowly rubbed it back and forth. I caught him looking down there once and thought he would object or leave the room, but he stayed and kept talking as if nothing were happening. To me it was his ultimate approval.

What a turn-on. How could someone so up tight about anything regarding sex or nudity let me get away with doing something that I would normally never do with another guy friend.

Can't wait until his next visit.

So my advice is to wear your boxers, enjoy the freedom and act as if everything is normal because it is. Wish you good luck.