I found this site by accident one day and I love reading the contributions. This is my first one.
I have a female friend who is aged 44. We have been best friends for about 20 years. She is just that, a friend. We made love several times years ago but we discovered we were better friends than lovers and we want to keep it that way. While we hang out together a lot it isn't what you would call dating. We are just usually with a larger group of friends doing things together.
I have always been open with her and she has long known that I masturbate, as does she and probably everyone else. Sometimes she will call me and ask what I'm doing and I'll tell her I'm laying on the bed enjoying myself. It's like it's no big deal telling her.
For probably the last ten years sometimes if we are together in my house I'll tell her I feel like taking my pants off and she doesn't mind. She will sit beside me and watch as I take my clothes off and bring myself up to a full blown hard-on. Sometimes she will sit beside me and lean on my left shoulder as I lean back and slowly jack myself with my right hand. I take a long time going slowly because it does excite me as she carefully watches me and I don't want to rush it. I tell her how good it feels as I stroke away.
I don't ask her to take her clothes off and join me, but now and then if she is wearing a skirt, for example, she might raise it up to her waist and slip her panties off and spread her legs and I'll look at her pussy as I jack off. Only occasionally has she also masturbated with me. She will usually just let me look at her pussy as she watches me. Most of the time though she will just stay fully clothed and sit beside me.
The feeling I get from it is one of being very relaxed, freedom to explore some fantasies verbally as I jack in front of her, and an exciting rush because of the paradox of me being naked and hard and jacking and her watching me fully clothed. She doesn't do a whole lot of talking as she watches but she does admit she likes watching me and she loves it when I cum.
That's my short and honest story about a dear and wonderful friend.