Since I was about 14 years old. I hated pyjamas, I had 4 brothers, and they all slept in underwear so I thought I'd try that, but still didn't like it, took them off and slept naked ever since. I served in the RAF for a while, and quite enjoyed sharing a room with up to 12 other guys, most of whom also slept naked! Interesting sights in the morning!
Its strange to me that people can have an issue with it. Do you know if your dad slept naked?
My dad slept naked once in a while but never as a rule. He is generally a conservative person. I wish he was more relaxed. I found my dad and mother nude in bed a few times when I was a boy but they said it was because it was very hot. We had no air conditioning, but it was probably because they fell asleep after having sex. They were reserved about nudity so it was not a practice. Seeing my dad naked in bed gave me the idea to try it but they told me I should wear pajamas but I don't remember the reason they gave me. I slept naked secretly once in a while. I shared a room with my brother and I was discreet. As soon as I went to college, as I mentioned in the earlier post, my room mate was into sleeping and hanging naked so we both did and I have done it ever since. Its seems crazy to me to wear anything to bed. My dad still changes into pajamas even when we spend time together at our cabin, but he is more relaxed about changing in front of me.
I started sleeping naked when I was 12. We use to live in Northern California on a river and I'd spend summers naked at the river with friends. Went home one day and wondered why should I put clothes on to sleep when I naked practically all day long? After that I started showing up in the kitchen early in the morning with just underpants on. One day I showed up naked -- mom freaked. Do I ever miss those naked summers on the river.
My story is a little different. For as long as I can remember, I never had pajamas. I always slept in underwear - just briefs in the summer and added a t-shirt in winter. I did this until about 4 years ago.
I had gotten very used to wearing underwear to bed, that I actually didnt like the feeling of no clothes because I didnt like how my balls would rub on the insides of my thighs when I slept. It even sometimes bothered my wife that after sex I would get up to put underwear back on.
Anyway, after sex one night, my wife double dog dared me to sleep naked for two weeks. We all know the weight a double dog dare carries, so I did it. I quickly got over the scrotum/inside thigh thing and have slept naked ever since.