First let me say I am a big fan of Solo Touch....I think I've read just about every story here and I love them all. This is my first time of writing; I am divorced and I date various women, which typically end up turning into relationships that last maybe six months or so before I break them off and move on. Up until now, I have never masturbated in front of a woman nor have I had any of them ask me to. I am fascinated by accounts I read here of guys who are lucky enough to have women ask them to masturbate for them, and stories by women who say they are mesmerized by watching a guy jerk his cock. Where are all these women? I even put an explicit ad on AdultFriendFinder saying I would masturbate for you, and got no takers. Most of the woman I date are pretty straightforward, sex is mostly about romance, a couple of basic positions, oral sex occasionally, and they always want me to cum inside their pussy.
I am dating a woman now who seems to be a little more interested in sex than most others, so I thought this would be the opportunity to masturbate for a woman and hopefully have her masturbate for me. But how to go about it? It's too drastic to one minute be making love in a romantic way, and then the next minute say 'honey, how would you like me to jack off for you?'
So after much planning and thought, I am in the process of trying to ease my way into masturbating with her. Here are a few recent developments. One time we were fucking and the phone rang....she had to answer it because she was expecting an important call, so we disengaged and while she was talking on the phone (for only about a minute or so), I sat up and started stroking my cock which was still slick with her pussy juices. I know that she saw me doing it but she didn't comment. If she had freaked and started screaming 'what are you doing?!', I had planned on saying I was just keeping it hard for you while you were on the phone.
The next step came while we were giving each other massages. I gave her a full-body massage using massage oil. While I was massaging her, there was plenty of teasing of her ass, tits, and pussy, but I didn't directly stimulate her. After about 20 minutes of this we were both pretty worked up. I had a semi-erection, and managed somehow to tuck it under so I could assume the position and let her massage my back. When she had me flip over to do my front, my erection grew to its full eight inches. She commented that it looked like I was horny, but she didn't touch it. Instead she massaged my shoulders, legs, and chest. After a few minutes I could see she was winding down the massage, so with oil still on my hands from massaging her I started stroking my hard cock and said 'you forgot a place.' She just laughed and said 'Oh, you want me massage there too?'
So I think I have desensitized her to the sight of seeing me briefly stroking my own cock, however we still have a long ways to go. I guess I've been hoping that during such times when she sees me doing that she might say something like 'it looks like you are pretty good at that, why don't you keep going?' But...no such luck. I am open to suggestions as to how to get from where we are now to a place where we could occasionally masturbate for each other.