I've had a couple of quick experiences being seen naked by a female friend before, but what I think is my first true CFNM experience was when my wife and I were still dating. She was going to school in a town a few hours away, on most weekends if I wasn't working I would drive down to visit her.
Friday evening we decided to make a playful bet on a sports game, where the winner would be allowed to make the loser do 1 thing, anything they wanted, no limits (of course personal safety and common sense applied)
It sounded like a fun playful bet, and of course I was hoping to make her do something new
In the end, my team lost, and my girlfriend told me I was to stay completely naked until I left to go home on Sunday, with specific instructions that I was to behave normally as though I still had my clothes on, no covering up, or hiding under a pillow, or anything else like that. If I wouldn't do it when I'm clothed, then don't do it when I'm naked. I thought this wasn't completely fair, since this would be something I had to do for almost 2 full days, but she pointed out that the bet was for 1 thing, and we didn't set limits on how long this 1 thing was to last, and she was only telling me to get naked once.
She was right, and I agreed, and figured this was a pretty tame punishment for me losing the bet anyways, since she's seen me naked many times before anyways. If I won, I was probably going to make her do something much worse than this.
Later that evening was when I realized things were going to get a bit trickier for me, and that my future wife was a devious schemer. I had enough to drink, and needed to pee, only then realizing that the layout of her apartment was going to be a problem. She lived on the 2nd floor of an old house that was converted into two apartments, she lived in one and her friend from high-school lived in the other, each had a kitchen and bedroom but the bathroom was shared, and at the end of the hallway. I now completely understood why she added the "no cover up" terms that I was so quick to accept.
I started peeking out the crack in her door, trying to figure out if her friend was home, or even using the bathroom at the moment, when my girlfriend opened the door and pushed me out saying "you wouldn't peek like that if you were wearing clothes, just go knock on the bathroom door to see if it's free".
So that's what I nervously did, and luckily didn't run into anybody unexpectedly. I came back to my gr's apartment and we decided to watch a movie.
We heard her friend get home, and that's when my gf looked at me with a smile, and said we should have her over to watch the movie with us and have a few drinks. I was stunned.... and she got up to invite her over. Moments later, I heard her friend say "Are you serious?" and start to laugh, and the two of them came through the door.
I don't think I've ever been this embarrassed in my life, not only was I embarrassed because I was fully exposed for her friend who I've only met a couple of times, but this is also when I discovered that when I'm embarrassed, I experience a good amount of shrinkage, which standing in full view of this woman I hardly know, made the embarrassment that much worse.
We all sat on the couch and watched the movie, me of course getting up to refill their drinks whenever they asked. Eventually they got out the camera and had me pose with them, after having a few drinks they even agreed to show a bit of skin for a few of the pictures, but the tops quickly went back on and I was left naked for the rest of the night.
After a couple hours the movie was over, and I actually started feeling relatively comfortable, and even started enjoying being shown off to my gf's friend. That's when CFNM finally clicked for me, and I ended up really loving the experience I had that weekend.
I could tell how comfortable I was getting, because I not only started to hang at my normal size, but I might have even been plumped up a bit more than usual. I insisted we pose for another picture so at least not all of the pictures they got of me was with Mr Tiny, lol. The girls were feeling generous enough to show a bit of skin for that last picture too