FR+ mixing it up with a milf

[Longshanks]

Over the last 3 yrs I've gone running occasionally with a 45yr-old woman who is really sexy. She's former military, so she doesn't take shit from anyone and loves to tease and be snarky. She has a 10yr-old son that I've met on a few occasions. There was always some sexual tension between us, but when I first met her I wasn't as skilled and I didn't know how to start things with her. Then I was in an LTR, and then she met a guy as well and date for a year. He was super jealous and wouldn't let her go running with me, so I haven't seen her for a long time, till a couple months ago after they broke up. I'm already in another relationship by this time (this girl; we had just agreed to be exclusive a couple weeks before this story takes place.)

She texts me to say we should start running together again, and I agree. She wants to bring her friend along, but I told her that I want to be able to talk with her, so I'd rather not have company. So I go for a jog with her on a Saturday afternoon and we sit in the part afterwards and catch up on each other's lives. I tell her about my relationship, she talks about hers that just ended, etc. This whole time, I'm getting turned on by her sexy attitude and smokin' body sitting just a few inches away. Eventually, I get the sense that she expected me to make a move already, and is wondering why I haven't. So at a pause in the conversation, I say

Me: "Caitlin, kiss me." And then I pulled her in for it.
[Pause] I screwed up here by not coming up with anything to say afterwards.
Her: "what was the meaning of that?"
Me: "I've been wanting to do that for a long time."
Her: "Just so you know, I had a dream recently in which we were intimate, and I really enjoyed it." (Yowza! This is actually the third girl to tell me recently that she's had a sex dream about me. The other two being my current g.f. and a hookup)
Her: "But, look, you have a girlfriend, I don't want to disrespect her. Also, I'm not really looking for something short-term right now, I need a steady partner."
Me: "Fair enough."
Her: "But it's quite an ego boost, I am glad to know I still have it going on!"
Me: "You sure do ;-)"

So I kissed her a few more times, still quite turned on. She drove me home, and then waited for me in my room while I changed into my suit, and then she drove me to a party where I was going to meet up with my g.f. later. Having her sitting on my bed and kissing her while I changed was hot, but it was so tough not to try for more than just kissing.

My g.f. sorta sensed that something was up, but she was also stressed out b/c of work and stuff. I confessed to her about a week later that I had kissed Caitlin, prompted by my g.f. sorta asking to confirm that we really were being exclusive. She got quite angry, understandably, but eventually we decided to stick together, but not be totally exclusive. We're still trying to sort the details out, but we're essentially monogam-ish now. (She's actually ok with this, she was actually hesitant for us to be exclusive. I proposed it after I stopped seeing the other two girls I had on the side. I assumed she wanted us to be exclusive, but that she was too timid to ask for it. Turns out, she didn't really want it, and just kinda went along with it. In fact, I had noticed her hesitation to agree, and asked her what she was thinking, but she blew me off and I just let it go. So better communication could have circumvented this whole dilemma.)

Anyway, so the lesson is that milfs are great, but don't cheat. And don't assume anything when you are in a relationship, make sure you explicitly ask about things and wait until you get a clear answer!

 

[Chase]

Longshanks-

Pretty clear this gal has the hots for you. You could've slept with her had you wanted to with ease, but I understand you held back on principle.

With exclusivity: try and avoid proposing it yourself (especially if it isn't what YOU want!). Better for her to propose it. She'll propose it when she wants it / if she needs it, and if she never does, then she just doesn't feel that strongly about you, which... you probably don't want to wrap her into an exclusive LTR if she doesn't feel too strongly about you. Better to focus on making her feel so strongly that she can't stand the thought of sharing you (if that's what you want), than to wedge her into it when her emotions are still kind of mild toward you.

Also, read your other lay report with your current girlfriend; if you're going to pursue an open relationship, it's HIGHLY important that you insist on condoms for at least the first, say, month or so. Insist. She tries to put you in raw - resist, and insist on a rubber. You will get less resistance to the open relationship format and have fewer trust issues around your cleanliness / responsibility if you kick things off being religious about wearing rubbers than if you start off like a loose cannon, raw dogging her and blasting in her. She will assume that whatever you do with her, you do with the other women you're seeing, and if you're loose about condom use, that can become a deal breaker very quickly.

Once you're into things, if you want to quit using condoms, it's good to go get tested together, you and her, and say that she's free to do what she wants and just be responsible, and if she slips up and makes a mistake it's fine, to just tell you, and then you and her can go get tested together. If you're running everything very neat and by-the-book like this, it minimizes drama and upset and lets you have a very straightforward open relationship.

Chase