I am 38 and married and love to masturbate here all the time. But here is the strangest way I have ever gotten someone else off.
I use to call this chat line in which people of all ages sent messages and sometimes connected. On many occasions, I would connect with some very hot woman, of all ages, for totally hot masturbating. It makes my cock hard now just to remember my dialing the phone number for this site.
But on a few occasions, I would get a message that some girl, usually quite younger than me, wanted to connect live for chat, and on these times, I would actually get an operator who worked for a service that provided translations for people who were hearing impaired. Thus, I would talk to the operator, who would type out a message to the girl, who would type something back to the operator, who would read out what the girl had said. This arrangement was slow, of course, but interesting. The best part was that the girls would always get sexy and clearly want me to make them cum. So I would chat sexy and hot with them telling them what I was doing with my cock etc, and the operator would pass this along to the girl etc.
For the most part, the operators were quite professional. But one time the operator was clearly getting turned on and was breathing hard as she read me what the girl had said. And when I would say how wet my cock was and how I was pumping it in my hand and moaning, the operator just breathed hard and fast and said softly 'oh, my god!' and then finally as I got close to cumming, the operator said 'oh fuck yes' and then coughed, probably trying to hide her orgasm, and when I heard this I came buckets all over me. I had completely forgotten about the girl I was presumably talking to.
Can you imagine this situation and what a turn on it was? I masturbated for weeks thinking of this and tried to get another operator to cum this way, but it was only this one special time when the poor operator clearly had to masturbate listening to me. I loved it.