I Finally Asked For What I Want (A Smoking HOT Sex Party With 5 Near-Strangers)

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How An Orgy Helped Me Step Out Of My Comfort Zone
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And oh, my ... did I get it!

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 became 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 a swingers' retreat 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 this 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!

 

Related: My Husband, Our Girlfriend & I Went To A Steam Room Swinger Party And WHOA!

 

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 possibilities for the upcoming orgy. 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 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 meds kicked in and everything became manageable again.

 

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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 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 f*ck, and 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 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 dick, so I was extra flattered that she was into it with me.

 

Related: How To Use A Strap-On Dildo — No Matter Who You Want To Do

 

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 wasn't 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 their rough touches and I had to ask them to back off.

As I was about to make out with another sexy woman, she mentioned that she’d performed oral recently. I appreciated the risk aware courtesy and 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 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 p*ssy-licking.

I cuddled and made out with a beautiful young man and we decided to find a good surface on which he could do me senseless. What we found was a slowly deflating air mattress, so good surface it wasn’t, but done 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 had sex with or watched having sex.

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 vag wasn't interested in any more insertion, but I’d seen him using a Neon Wand 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 electro stim (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'm excited to think about where this will take me on future sexy adventures.

 

Listen now: There is a sort of order from chaos that happens when like-minded people discover others like themselves. Individuals become clusters, clusters become groups, and with groups come unavoidable growing pains, issues, conflict, and struggle. Still, there’s a certain magic that comes from having a group of diverse and motivated people with a common role come together to build something because when you get it right, you end up with a community. Community role models are essential and on this episode of Life on the Swingset: The Podcast we discuss poly role models and the joys and struggles involved with building sex positive community.

 

 

This article was originally published at Life on the Swingset. Reprinted with permission from the author.

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