In most respects my coffee date with Jake went much better than i thought it would. Looking back, i was probably more nervous than i needed to be, but i think being on edge and nervous makes me more careful and in situations like this, i think that's important. When i think back about the comments Jake's made at the gym and in past conversations, i shouldn't have been as anxious as i was. i'm glad it's finally over!
We talked for more than two hours and about halfway through our time together, i found the right time to bring up my feminine side and desires. By that time we had discussed likes, dislikes and fantasies enough to determine that Jake was much more inclined to being dominant and i submissive. i finally went out on a limb carefully and asked him if he would mind if i wore panties for him. That question opened the door and led our conversation in exactly the direction i was hoping for.
Jake paused and looked me right in the eyes and said "I'd like that. I might even insist on it."
The second part of his comment did catch me by surprise and he could tell. The way he said it turned me on as well. i didn't say anything and after getting over a tinge of embarrassment, smiled back at him.
"Are you wearing panties now?" he asked me. i told him i was and he proceeded to ask me what color they were. i told him they were white and he asked if that was my favorite color. "Not really. i just thought it would be easier for me to slip white ones on at the gym" i told him and let out a nervous laugh.
"Next time wear something a little more feminine" he told me. There was a smile on his face but there was no doubting his seriousness. i got that submissive feeling once again and enjoyed it.
The most awkward part of the conversation came when i told him i wanted my wife to meet him as a friend of mine so that i would be able to establish a "cover" for getting together with him and not raise suspicions. Initially, i thought i would have a hard time convincing him of this because he seemed to be reluctant to do it. Finally, he agreed it might be a good idea. It was awkward for a couple of moments, but at least now i've set it up so that Diane will be able to meet him and hopefully give me permission to move forward. i told Jake that they'd already met at the gym and this would just reinforce our being friends.
Our next date is supposed to be later this week. We're going to get together for a late afternoon round of golf. The plan is for Jake to pick me up and drop me off after the golf when he'll get a chance to meet Diane.
i know this all sounds very complex, but good things take a lot of work most of the time. This time, i'm hoping it's worth the effort.