Firsts are always fun
Brian moved in across the street from me, his parents were divorced so he lived with his mom and sister. We became friends quickly after they moved in. Since his mom worked and his sister was somewhat older, he and I spent a lot of time alone in their house.
Brian had an obsession with being naked. When we would play in his basement or garage, he always suggested we take out our dicks. I had no objection to this. We would just pull down our pants or shorts show each other our dicks and then pull them back up. A few times he would open the garage door, while our pants were down, but his garage was under the house so no one could really see anything.
If we had a sleep over, we would always take a bath together before going to bed (another chance to be naked together) and play with each other's dicks in the bath tub. Then we would usually go to his room and play some more. Usually we would just touch each other's dicks. As time went on though we would jerk each other off.
One time when we were at his house playing. He decided we should go into his sister's room naked (no one else was home). We were naked on her bed when he said we should jack on each other's dicks for 60 seconds. I jacked on his dick for the 60 seconds, then I laid back on his sister's bed and he jacked me for my 60 seconds. How I wished it was his sister! After that, we jerked each other off back in his room as not to make a mess in his sister's room. We jerked off together in his room quite often.
How I wish I had taken a pair of his sister's panties back then.