Weekend Away Turned Into Something We Didn’t Expect
We live in San Diego, so this wasn’t a big trip — just downtown for the weekend, staying at a hotel in the Gaslamp Quarter to shake things up and do something different from our usual routine.
First night we hit a Spanish tapas spot near the hotel — sangria, live music, good energy. When the club downstairs opened up we went down to dance. At one point I stepped away to grab a drink and just let her dance on her own for a bit. Didn’t take long before guys started circling in — she genuinely hadn’t noticed until I pointed it out. She lit up.
Second night was supposed to be a bigger “game” — deliberately putting her in a position to get hit on at a bar while I watched from a distance. As we got closer to actually doing it, I could feel her nerves rising. She was going through with it for me, not because she wanted to. So I scrapped the plan on the spot and reminded her the whole point of this is us having fun together, not checking a box.
Instead I pulled out some truth-or-dare prompts I’d written ahead of time — confidence stuff, flirting stuff, bringing it back to us. Took the pressure off and got her loose. It spiraled naturally from there into F-Marry-Kill with people at the bar, then guessing games about strangers (swinger? sexless marriage? into BDSM? throuple?). She was having a genuinely great time and I could see her head shifting into a different gear.
A guy ended up in the open seat next to us at the bar — turned out he’s in the lifestyle himself. He picked up on the fact that I was into it pretty quickly, actually — I mentioned the Strictly Anonymous podcast at some point and he connected the dots right away. She’s naturally friendly and curious, so she was asking him a lot of questions as the conversation went on. He knew the area well and took us to a whiskey bar down the street. We ended up on a couch together, her in the middle between the two of us, and things built gradually from there — hand near her, arm along the back of the couch behind her. At one point he checked in with me directly, made sure I was good with where things were headed. At one point while I was gone he asked her out directly.
We wrapped up the night not long after that and headed back to our hotel — just the two of us. He didn’t come back with us; he walked us partway since his car was nearby, then went his own way. Watching another guy work to earn her attention, while I was right there part of it, hit something in me I didn’t expect — genuinely one of my fantasies playing out in real time.
Back in the room after, just her and me, she was glowing — flattered, turned on, and she told me having me right there the whole night was what made her feel safe enough to actually enjoy it instead of just tolerate it. What followed was some of the most intense, dirty, uninhibited sex we’ve had in years. We’ve spent the last day just talking it through — how it felt from her side, from mine, and she’s suddenly got a lot of questions about lifestyle terminology she never asked before.
She’s still got two brand new dresses that never made it out of the closet this trip — already plotting a couple of date nights to put them to use. Open to suggestions.