Chicago Play Party Take Two
I love going to play parties and getting my sexy on in a semi-public space. At events where I don't know people, or don't know them well, I almost always stick with my current partners for playtime. I love to get down and dirty with those I know and have an established connection with and enjoy the sexy vibe of all the others surrounding us, but I very rarely step forward to play with new people.
On my most recent trip to see Will and Elle in Chicago, I decided to break through that self-imposed barrier and I played with five(!) people I hadn't previously. Four of them I'd met last year and been friends with through social media, so I did feel like I'd gotten to know them, and I'd been crushing pretty hard on at least one gal but had been too shy to make a move. One of the guys and I had intended to play together at Swingset Takes Over Desire in November, but we just never seemed to be in the right mood when we were in same physical space.
We all started out with a group chat about a week before the event and did a lot of flirting and exchanging of naked photos. I decided to take the initiative and privately messaged the woman I'd been crushing on to tell her that I thought she was sexy and would love to play if she was interested. She was--Squee!--so buoyed up on that success, I messaged a second gal to express similar sentiment and she was also interested in playing. Huzzah for asking for what you want!
After being in such a funk through most of the winter, it felt really good to feel more like my perky self, so I decided to put myself out there and initiated some discussion of mildest and wildest for the party. Since it was a very limited number of people and I knew I was at least nominally attracted to each of them, I decided that my mildest was to make out with every person there who was interested in doing the same. I'm normally too shy to even kiss people I'm interested in so this was a good way to kick start the proceedings.
I had a mild panic attack before the party started, which appears to be a normal thing for me, based on my experiences so far with travel and play parties. What if I was actually really bad at sex and the gals I'd hit on were really disappointed since I talked a good game but couldn't deliver? Fuck my brain! I grabbed the quietest corner I could in a busy apartment with no private space and did my mindfulness meditation. When I finished that and was still crying, I took some anti-anxiety meds and sat in the living room with Elle watching an episode of Archer until the drugs kicked in and everything was manageable again.
Guests arrived and we had good conversation and wine and food for a bit before we moved into a welcome circle and talked about everyone's wants for the party. Several people mentioned being into doing *stuff* and we laughed at the delicious vagueness. Most of them play together often so I was the outlier and stepped up to talk about what I might be into for the evening. Having already started the conversation online, it was easier to feel comfortable, and I was quickly making out heavily with Taran and en route to stripping her naked and strapping-on to help fulfill one of her sexy requests for the evening.
Once I settled into the party I felt very good and strong and sexy and approached the other woman I was crushing on. She had all the qualities of women I'm often intimidated by--super hot, geeky as fuck, seeming so much cooler than me--but I knew she was interested in playing so I stepped up and we made out a bunch before I undressed her and thoroughly explored her body with my mouth and hands to much ecstatic effect (wow, it's like I was just writing Victorian erotica there--I licked her pussy and fingered the hell out of her until she came hard). I then asked her to strap on, and as I jacked her off before riding her, she mentioned she didn't normally wear the cock, so I was extra flattered that she was into it with me.
When she moved on to clean up, and my legs slowly recovered from orgasms that soaked us both, MP approached and we decided to attempt the fisting we'd discussed previously. He used his mouth and hand in amazing ways, and we had a great time, but it was not to be with getting his hand inside me. I suspect my pelvic bones may limit this particular fantasy, but I'm willing to keep trying. Several people came by and groped and made out with me while this was happening and it was so hot to be touched by so many hands and mouths, even if they were occasionally too enthusiastic with rough touch, and I had to ask them to back off.
As I was about to make out with one sexy woman, she mentioned that she'd sucked a cock and licked a pussy recently. I appreciated the risk aware courtesy, and I was very game to go for the kissing. What she didn't mention, and if she had, I probably would have passed despite her hotness, was that she'd recently smoked a cigarette. Yuck. I am so used to the Wet Coast where almost no one smokes (cigarettes) so it came as quite a shock to get a mouth full of ash taste. In my opinion smoking requires much more of a warning than pussy licking.
I cuddled and made out with a beautiful young man and we decided to find a good surface on which he could fuck me senseless. What we found was a slowly deflating air mattress, so good surface it wasn't, but fucked senseless I was, so the important part of the mission was accomplished. We eventually grabbed some food to refuel and it struck me how easy it is to hang out naked at a sex party, chatting with people you barely know, and have either just fucked or seen fucking.
William (not to be confused with Will--there are only so many names) approached shyly and asked if I wanted him to use the njoy Pure Wand on me. My pussy was not interested in any more insertion, but I'd seen him using the Neon Wand electrostim on someone earlier and asked if he'd like to do that to me. He was in and we returned to deflating air mattress for more fun. It had been ages since I'd had electrostim (aka 'zorching' in my fancy technical lexicon) and I'd forgotten how much I like it. One of the best things we did was when he used the Power Tripper adapter under my leg to send the current through me, then used the metal blades on a Freddy Krueger glove to receive it through my skin. If I hadn't squirted myself dry earlier, I would definitely have come from the sensations.
Eventually people got dressed and started filtering out. Hot cookies were ordered for delivery--so glad that danger isn't a thing here--and many of us snuggled on couches, chatting and laughing. Light, friendly touching abounded and I was so very content to be amidst my tribe. I'd taken risks in a safe space and they'd paid off beautifully for me. My comfort zone was now that much larger and I was very excited to think about where this could take me for future sexy adventures.