Years ago, we use to go boating with friends on a river. My buddy had a crazy fast boat that at high speeds use to just bounce on every wave. After a day on the boat with friends, I remember joking with the guys about how our nuts were sore from hours of bouncing. We all had some sort of board/volleyball shorts on. In conversation, I mentioned that I needed some sort of support under my shorts if I was going to go out on the boat the next day. My one buddy completely agreed. Later that day, my wife and I happen to be picking up some stuff and drove by a sporting goods store. I said to her 'lets go in and see if they have anything because I really can't go out on the boat again like I did today.' In my mind, I knew speedos would do the trick. My wife and I go into the store and I walk right up to the rack of black Speedo Endurance and said "this will work!" She suggested we get a second pair for my buddy who was also complaining about the pain. We get back and we gives the second pair to my one buddy. There was a big groups of us and we are all good friends so I am sure there were a few jokes going around between everyone. The next day we wear them under shorts and all went well. We both kept them on once we got back to the house, the drinking started. The house had a pool and at some point, both my buddy and I took off our shorts and just went swimming in our Speedos. Since the larger group already knew we had them, it was a big joke but not a big deal. It was even less for me since I have worn Speedos off and on since I was in 8th grade.
That was the first and beginning for my wife seeing me wear speedo. Since then, I pretty much wore them off and on with my wife and with the same friends privately at pools and in our hot tub. As time went on, I got rid of all my long board shorts (which my wife never like but tolerated since she knew I had lived in a coastal area and I actually do surf) and replaced them with shorter 3" & 4" type swimsuits but I still also kept wearing my Speedos on occasion. I finally made what I call the 'plunge' a few years ago on a trip to Mexico. I needed a new swimsuit so I went online and purchased a pair of black Diesel square cuts. Up until then, I still didn't have the confidence to wear swim briefs to the beach or in public but I figured nobody knew me in Mexico so this would be my chance. I showed my wife the new suit and although she was slightly surprised at the choice, she said they looked good. The first day down there, we go to the beach early to claim a spot. I still remember the rush of me taking off my shorts thinking I would be the only one. As it turned out, it was August and a big month in Mexico for French Canadians and Europeans tourist. The beach had a ton of guys wearing Speedos. At some point of the trip, my wife turns to me and says "you should get a new pair of speedos, you could totally pull it off." That was it and all I needed to hear from her. After the trip I went on a buying spree and I have pretty much haven't looked back. As for my kids, they are too young to think anything of them. They will grow up knowing that both my son and their Dad wear swim briefs. As for my buddy, I know he still has them. Throughout the years when we have all gotten together again (and are in swimming environment), he has worn them. However, I would be surprised if he wears them to the beach or out with anyone else but our group of friends.
So to sum up the story, try to ease your significant other into the idea and if you have kids, expose them early to the idea.
