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Infatuated with an Irish MILF
I have been playing a online game (similar to Words With Friends) for a few years now with a woman my age (50ish) from Ireland. (I'm in the US.) We are both happily married. We chat and flirt a lot through the games chat feature. We also became Facebook friends so we could keep up with each other's lives and see family/vacation pictures, etc. Our flirting has never really gotten anywhere close to inappropriate, but I must confess to wanting to take it further. I get the feeling that she would enjoy taking it further as well, but I'm afraid of saying something that takes it across the line and alienating her. She is very sweet and drop dead gorgeous, so I definitely wouldn't mind seeing some flirty pictures of her and exchanging some inappropriate emails, but I'm too chicken to step over the line.
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I had an online relationship like that and it was similar. I really liked her and respected her and did not want to offend her or jeopardize the relationship. But the flirting was getting heavy and she enjoyed little fiction stories I’d write that were sort of romantic fantasies with us as the characters. But they were quite innocent and tame.
Anyway, I wrote one that stepped way over all the lines I’d previously not crossed. And the two characters were other people, not she and I. Oral sex, intense fucking, ass licking, toys, restraint, you name it. I was nervous to click the send button. But she loved it and told me it made her wet and she masturbated to it. That broke the ice for sure. We are together for real now and it’s the greatest relationship and incredible sex.
In your case, you may just want to come out and ask her. Tell her you really enjoy and value the relationship, and you find the flirting fun and don’t want to jeopardize any of that. But you have feelings and desires that go beyond flirting. Ask if that offends or shocks her, or if you can share some of those feelings with her. Worst case she says no but you’ll at least preserve the friendship. I’m betting she’ll go for it. I mean she’s married and having sex with someone already, right? She’s not a nun. Good luck and update us if you go for it.
Thanks for the encouragement. I'm definitely leaning towards doing it, just need to work my courage up and figure out how to break the ice.
You have to take the risk. I did and the sex has been incredible
I'm not even thinking about sex, honestly. More like exchanging naughty pictures and steamy emails, etc.