Imagining what could have been and what still may be.

Mister_De_Sade

Male
Gold
While my wife and I have experienced some truly amazing sexual moments with each other and with others over the years; there are moments in the past in which we took door number 1 instead of door number 2 and regrets remain for not taking the chance with those moments.

Considering where we(she) started, a loooooong way has been traversed since that time. When we first got together nearly 20 years ago, she'd only been with two other guys previous to me. She'd never had anal sex, never deepthroated dick before, and had NEVER been with more than one person at a time. Now all of those things are true, and then some.

Still; she hasn't done cam shows (Chaturbate, ..., etc) yet, though it's been brought up (by her and me) a few times over the years. Watching and directing her exposure in real time to strangers online is still at the top of my to-do with her.

Then there was that brief time some years back in which she seriously considered applying to Kink.com to star in some scenes. This is when their headquarters was in San Francisco, so the prospect of visiting SanFran AND getting to watch my girl star in some of our favorite professional porn was mind-blowingly exciting. She even went so far as to begin filling out a talent application on their site. Alas, it was postponed, and now Kink is in Vegas (a city we don't really enjoy) and their content is nowhere what it used to be. (sigh)

Lastly, I had an opportunity just prior to COVID to rent out a swingers bar for an entire afternoon for a private party (in which my girl would be a party favor), but that fell through when the place closed down. Still trying to find a similar spot not too far away from us for a similar event, but that venue was so perfect for the scenario that it still bothers me that it didn't come to fruition to this day, argh!

What are some playdates, events, or scenarios that you have missed out on or wish to still accomplish with your partner, sub, cuck, vixen, etc?
 
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