If I could ask for your advice here.
My best friend has been my best friend for a long time. We sat beside each other through school, most of time sharing double desk with thighs touching all day. To this day, when we get together, we sit with thighs touching.
We got naked at home after sailing and lay naked on bed. We compared cocks, both cut - rare in Ireland, and discussed masturbation techniques but he said no to jerking off.
One night in college we shared my single bed. I woke up kind of to his hard on poking my butt in his sleep. I turned around and his cock was out. I jerked him off and as he came he leaned into my ear "did you cum too yet?". To my eternal regret, I froze and pretended I was asleep!! Next-day was awkward and we were cool to each other or awhile but soon we were back to normal. His brother joked we were going steady we went out together so much.
In 30s, we went on short trip to Amsterdam. Got naked in hotel spa. Watched porn in room after. Heard each other wank after Iights out. Saw each other briefly when he switched on bathroom light to flush toilet paper he came in. We both just smiled.
At 40, I stayed with him a night. His wife (now ex) went to bed. We always open up on relationship and sex problems and did so over whiskeys. As I talked, he rubbed my inner thighs sympathetically. Then his wife shouted at him to come to bed.
He invited me to his summer house on August. During lockdown we reminisced on old days and admitted we both still masturbate, especially as wives (we remarried) lose interest (totally, in my case). We never acknowledge I wanked him off that time in college.
Advice, please? He's my closest friend. I don't want to fuck that up. But I so want to get naked with him and jerk off openly together with him even just once.
What we already did is already pretty amazing.