I have had this happen a couple of times. First, I don't like to be nude unless I am in an environment where nudity is expected and accepted. So generally that is going to be at clothing optional resorts and beaches.
1. The one that stands out the most because of the volume of people involved was at a clothing optional run. It was cool/cold when I arrived and I saw most people park their cars and going into the clubhouse with sweats or regular clothes on. Knowing that would be the case that most would not be nude, I got out of my car and immediately started to get undress. As I was doing this, two Asian couples were getting out of their car next to me. One of the women commented that she thought it would be to cold for anyone to be nude but she guessed not looking over at me, now nude and putting my clothes in my car.
As I walked down to the clubhouse it became pretty clear that I would be the only one nude at least for the walk to the clubhouse. Once inside there was probably 100 or so people all dressed in at least sweats. This went on for about three hours, me being nude and everyone else dressed, until race time when all the runners undressed. Even then, the nonparticipants stayed dressed. It was thrilling to be in a clothing optional environment with literally 100 people who were dressed and I was completely nude. I even took my shoes and watch off to complete the nudity!
2. Another time I was at a friends house for a party that was to be clothing optional. They live out in the country so its kind of isolated. Good place for a clothing optional party but kind of a ways to get there. When I arrived, the two husbands had just left to go get some beer from the store it was a 15-20 minute drive each way to the store. My friend's wife (Helen) and two other ladies (Jan and Margret as I found out later) were there having a glass of wine, they all were still dressed (although I did not know it at the time) but from the invite knew to expect nudity.
Helen says as she welcomes me in the house, John and Dave went to the store so its just us here. She often stays dressed in case someone comes to the door while John and I are nude, so it didn't clue me in that the other lady would be dressed as well. Why don't you get comfortable and I will pour you some wine. So I step into the hall bathroom and undress. I walk into the living room to Helen (who I had been nude with many times before) and Jan and Margret (who I had never met before) stark naked and they being dressed. I found this very thrilling. Jan apparently had been to several clothing optional locations and participated in varying degrees from staying dress to topless to completely nude. My nudity did not seem to phase her at all. Margret on the other hand had not ever been in such an environment, loved her stealing glances at my cock. After some time, maybe an hour John and Dave arrived and shortly there after everyone undressed.
Other times, I have been at a clothing optional beach and struck up a conversation with small groups of people between 2 and 10 where they were dressed and I was nude. But other nudes were in the area so I is not really the same thing.

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