The Meet-Up: Finally Connecting in Person with a Sexy Friend

My sweetie and I took a recent trip to Chicago. I’d been wanting to go to the city since, oh, around the time I’d started chatting with a sexy friend from there, but I didn’t imagine it would happen. It’s an expensive trip from the Wet Coast, but we realized we had enough points to do it, and there was a musical based on one of our favourite books that Flick really wanted to see playing only there. It wouldn’t be a trip entirely based on getting laid, so we decided to go for it.

I’d been chatting with Will for about six months, starting with an innocent Twitter exchange that bloomed unexpectedly into a fun, sexy friendship. I’d been pretty hesitant to suggest a visit to Will because I wasn’t entirely sure he wasn’t just putting up with my newbie foibles. He seemed to like me, and he’d politely declined previous suggestions to meet up somewhere between our two cities, citing work obligations, but you never know if someone is trying to be ‘nice’ when they turn you down.

He’d been a lot of my firsts on this crazy non-monogamy journey: the first guy I flirted with, the first guy I took lingerie shots for, the first guy I sent shy slightly-nude pics to, the first guy I sent graphic nudes to. The internet barely existed when my husband and I were dating, camera phones and instant messaging certainly didn’t. I was extremely shy about it all initially, but my inner exhibitionist cheered at his enthusiasm for my photos, and now I take and share pics with eager abandon.

We knew we were going to meet at Swingset Takes Desire in November, but that was still months away, and it would be really great to find out if we were as compatible IRL – as the kids used to say – as we were online. Even OkCupid gave us a 97% compatibility score, but computers don’t know jack about chemistry and the various other je ne sais quoi aspects of attraction. I was fairly confident it was going to go well, but we tried not to have expectations, planning to have a fun night chatting even if it was a ‘nope’ on the physical.

I felt a little selfish for taking such a trip because it really was about me and my connection with Will. Flick was game to go along, and Will’s gal Elle was also keen to meet-up, but there was the potential that our two partners could be left in an awkward place if it turned out that Will and I had crazy chemistry and they did not.

There was a bit of a planning fail on our part because we booked an Airbnb close to the theatre, not really thinking about how huge Chicago is, and how far our friends would have to travel to see us. I didn’t want to be a creeper and all, ‘Where do you live in the city? We should stay close to you,’ when, in fact, that would have made much more sense, and is a perfectly reasonable ask when you’re flying 3000km, er, 1700mi, to see someone. They ended up having to drive an hour to come see us, and worse, do the same in the early morning to get home after – spoiler alert – much wine and sexing. (This may not seem like a lot to some people, but I really hate driving, and the reason we haven’t checked out more of our local clubs is that they’re 45 minutes away. In the suburbs!)

The delightful Elle showed up first. Despite our conversations online about which of us was the more awkward penguin, she and I hit it off effortlessly. She was beautiful, tall, curvaceous, and charming, our kind of geek, AND she brought cheese. Be still my beating heart!

I headed back down the three flights of stairs when my phone buzzed that Will had arrived. We had a quick kiss hello and then I barely resisted running excited circles around him squealing, ‘Squee!’ and opted for my classic non-stop, nervous babbling as I led him to the apartment. He was really cute and had beautiful eyes, and I couldn’t believe we were finally in the same place at the same time.

Wine in hand, the four of us settled into a relaxed chatting groove surprisingly easily. Similar tastes and geek-culture references made it easy to connect. As the night went on, I realized Will and I had previously discussed what we’d do if the connection wasn’t there but hadn’t discussed what we’d do if it was. We’d been moving closer together and Will started stroking my leg as we chatted, but the tone was still fairly platonic. Will started the transition in tone by bringing out an impressive collection of sexy toys to show us. We oohed and ahhed and fondled them for a bit and then a silence descended.

“Well, that was MY move,” Will declared. “Whaddya you guys got?”

Shit! I thought. I’m terrible at moves. I looked nervously around the room and then went with the only one I’ve got. I grabbed Will’s face and kissed him. My stomach dropped in that wonderful little flip as his tongue slid into my mouth, and I knew we weren’t going to have any troubles on the chemistry front. We kissed for a bit, then I broke away with that sweet reluctance that comes in a group sex situation because I was also eager to kiss Elle.

The split-attention thing during any more-than-two-way is my least favourite thing about group sex and is why I’m much more inclined to solo-dating than swinging. I wanted so badly to focus my attention on the guy I’d been sexting for half-a-year, but there was a beautiful woman I wanted to give attention to as well, so I didn’t know which way to turn. Flick moved in as I was kissing Elle and she redirected her attention to him, so I left them to get acquainted and turned back to make out with Will some more.

The night has a certain disjointed feel to it, the way things do when you’ve been looking forward to them for a long time. I have a hard time recalling the exact details (not because it wasn’t awesome) because I was in such a ‘Holy shit! This is really happening!” headspace. I do remember fucking on an antique armchair, seated reverse cowboy, while we watched Flick perform epic oral on Elle (she made the best happy noises) on the couch across from us. It was exceptionally hot. I love watching him work, especially while impaled on a hard dick.

After Will came, we moved to the bedroom, where there was a squirt-safe Throe, and he proceeded to demonstrate an epic toy on me, making me squirt until I dissolved into my trademark sobbing mess when I get overwhelmed by pleasure.

I’d warned Will that that might happen, so he wasn’t panicked like the partners who hadn’t been given the heads-up that I might just start bawling mid-fuck, and I didn’t have to reassure him between gasping sobs that it was, in fact, a good sign that I was crying.

“Are you having a ‘sode?” Flick called from the other room.

“Maybe,” I squeaked through tears into Will’s chest as he held me in his arms.

We hung out chatting quietly together after that. Gentle touches and exploration that we hadn’t gotten to in our initial frenzy to get naked and get him in me (we’d had six months of fairly intense foreplay). This quiet intimacy stays with me as much as the awesome sexing. I LOVED the hot, sweaty pounding part of the night, but spending intimate time with someone after the fact can be just as amazing if you’ve got an intense connection. I realized I was in serious crush territory.

Flick and Elle joined us on the bed and the four of us alternated between chatting and fooling around. I got to inspire some of Elle’s wonderful pleasure noises when I strapped-on, but eventually we were content to simply cuddle and talk until we were starting to drift off. Will and Elle had a long drive home, so we dressed and prepared for goodbye.

I felt melancholy as we bade them goodnight. We’d had such a wonderful time, and I hated knowing that it would be four months until we’d see them again. I haven’t clicked nearly as well with any of the guys I’ve dated at home, and it sucked to know there was a great match out there, but he lived far away.  In some ways it would have been easier if we hadn’t sparked as well as we did, but we’ve had fun chats since I got home, and we’re making sexy plans for time together at Desire. 78 more days of foreplay.