I was nine when I had my first dry orgasm. I knew from a very young age that it felt good to touch or squeeze my little pecker but never played with it long enough to reach an orgasm. Anyway, my sexual awakening happened like this; I was 9 and had a few sleepovers before but nothing really sexually happened during them. One Saturday afternoon I was at a friend's birthday party and one of my other friends (let's call him Matt) who was also at the party asked if I wanted to come and sleepover at his house. I had not slept over at his before, nor had he at my place. Matt's mum was also at the party as she was friends with the mother of the boy whose party it was but my mum was not. Matt asked his mum if it was okay and she agreed so when my mum came to collect me, Matt's mum asked her and she said okay but that she would have to go home and fetch me some pj's on which my Matt's mum replied that I could use some of his.
When we got to Matt's house, his mum told us to go and bath, as we were quite dirty after the party. We fooled around inside the bath like normal 9 year olds for quite a while when Matt's mum shouted at us from the kitchen to get out and to get dressed. She also told Matt to give me something to wear. Obviously I did have a good look at his pecker, which looked a bit bigger than my own but also circumcised. We got out, dried ourselves and my friend hung his towel back up before opening the door to run naked to his room. I didn't want his mum to see me naked so I wrapped the towel around my waist and followed. Inside his room, Matt was busy taking out 2 T-shirts from his drawer and he threw one to me. He slipped his over his head and I did the same with the towel still around my waist. I expected him to take out pj bottoms or shorts or underwear but instead he closed the drawer and asked if I wanted to play TV games. He ran out the room and left me standing there quite confused.
Wearing a T-shirt for pj's wasn't new to me as it had stated to become fashion then but I always used to wear underwear or shorts with it and so did my other friends who I slept over with before. I loosened the towel, dropped it and looked at myself in the mirror thinking maybe my penis was visible but it wasn't. The T-shirt reached almost to my knees and was very wide. I turned around in front of the mirror and I became aware of feeling naked although nothing was visible. I realized it felt good and I suddenly started getting a hard on. Matt called me from the living room and for a minute I forgot about my semi nudeness. I walked there to find him busy putting a cassette into the TV games. We started playing but my mind kept on going back to my bareness under my T-shirt and every often I could feel my penis rising. I took care to sit in such a way that my bottom was fully covered but Matt didn't seem to have any inhibition and quite often his pecker and or buttocks would be visible, even when his mum or dad came into the living room. Sitting at the supper table I got a rock hard erection and my pecker started itching. Touching it felt very good.
After supper we all went into the living room and watched some TV for a while, me and Matt sitting next to each other. After a few minutes, he moved into a half laying position and, his T-shirt moved up exposing his milky white buttocks. It gave me another erection and I felt like touching his buns. I was sitting there squeezing my hard pecker through my T-shirt. Matt got bored watching TV and suggested we go and play in his room. We played with his action men for a while and started wrestling each other. I kept on trying to keep my T-shirt down which wasn't possible for long and I became aware of my pecker touching his silky naked skin and again started getting a hard on. Matt must have felt it as he rolled of me and pointed at it laughing. I quickly pulled down my shirt to cover it and felt myself blushing. When I looked back at him, he had his pecker in his hand, squeezing it. He played with it for a minute while I watched very exited.
'Lets go to bed.' He said, got up and closed the door. He had twin beds and got into one. I climbed into the other one. He started talking about girls and I could see his hand under the covers playing with himself and it made me very horny so I did the same. After a wile my dick became more and more sensitive and I felt like I was going to pee so I stopped. When the urge to pee went away after a minute I started again and it carried on for a long time, stopping every few minutes to let the urge to pee go away. Once after a while the good feeling got so intense, I couldn't stop myself and stroke harder and faster and the most wonderful feeling spread through my loins. I had my first dry orgasm.
My mum collected my the next morning and during the day I thought about it many times and couldn't wait for bedtime to come so I could try it again. I associated the pleasure with wearing nothing under my T-shirt and after taking my bath, I tried on a few T-shirts but didn't have one as big as the ones we wore the night before. The biggest one I could find just covered my private parts. I went back into the living room where my mum, dad and older sister was watching TV and sat down next to my mum. The T-shirt was long enough to cover me while standing but not quite long enough when setting and as I sat down my pecker became uncovered. I quickly pulled the shirt over it but mum noticed. 'Where's your pants son?' she asked. I told her that Matt didn't wear pants with his T-shirt and that I also slept like that the night before and that it felt very comfortable. Dad looked at me and told me to go and put some pants on but mum said to leave me alone as I was only a little boy.
Sitting there I kept thinking about going to bed to be able to play with myself but realized I couldn't go to bed too early or my parents would get suspicious. Where before I always argued when I was sent to bed, from that night on I couldn't wait for bedtime. The next day when I got home from school, I found 3 of my mum's T-shirts on my bed. I asked her about it and she said it was for me to wear as pj's. I was in seventh heaven. I went back to my room, stripped my school clothes and underwear of and tried them on one by one while my little pecker was rock hard. They were as big as the ones Matt had, almost reaching to my knees.
I was 11, almost 12 when it first occurred to me that it would be even more exiting to sleep in the nude. For about the last 6 months before that I would wear shorts with my T-shirt after taking a bath until going to bed as I started feeling self-conscious when in the presence of my parents and sister. Before getting into bed, I would remove my shorts.
My own son who is 4 now, had the luxury of experiencing the freedom of wearing only a T-shirt to bed since he became nappy trained and for as long as he feels comfortable with it, we will let him.