A little more than 24 hours ago, I made a life-changing decision and had the best night of my existence. Enough that I want to write about it and share it. And I already want and need more.
My vitals: straight male, mid-30's, mid-divorce. 5'9", about 250. If I were into men, I guess you could say I'd be a bear. I've had some experience with kink and non-monogamy, but since getting divorced and moving near a major northeastern city, I've decided I want to explore these more. I know I'm a dominant person who isn't all that big on physical monogamy, but in terms of actually playing, I haven't done much.
As it turns out, my ex-girlfriend from college, Carrie, had also gone on the same journey (divorce, sexual exploration). However, she joined a couple of swinging groups in her area (which was closer than I expected) and has blossomed big-time. A while ago, she mentioned that she was going to be dancing in a stripping contest at one of those groups. Back when we dated, Carrie wasn't exactly repressed, but she's gone headlong into kink, so I desperately wanted to see her in a new light. And have some fantastic sex, of course.
I was on the fence about going for a couple of days, messaging one of the organizers through a prominent website (oh, for fuck's sake, it's Fetlife, I'm under the same username there) and someone else who planned on attending. The morning of the party, she told me I was on the guest list, and I spent most of the day overthinking what I was wearing. I'd never been in a group like this, as my BDSM dabbling was limited to home parties. I didn't want to make a bad first impression either, but I also worried about not getting to take part in anything.
The party was in the second floor of a converted building, and after signing all the requisite releases, I made my way up and into Carrie's arms. It was just like old times, only she was in costume and I couldn't wait to see her out of it, even if it wasn't with me. Carrie gave me the tour of the space, showing me the play rooms and introducing me to some of her lifestyle friends. I was still nervous as shit, though, between my anticipation and social anxiety, so I headed out to get some beer (the party's BYOB) and settle down somewhat. Then she wandered off with one of her friends into one of the play rooms and closed the door.
Shit.
I texted a couple of friends who I knew would be supportive of me, drank some, and waited for them to leave the room. They did and I followed them to one of the lounge rooms (the play rooms had beds, one room was a dungeon, and a couple of rooms just had couches to sit down, relax and of course whatever you bloody well desired). There was another couple in that room, they were fellow first-timers, and as Carrie left to attend to something, her friend started talking to the three of us about the scene, psychology, podcasts–
And that's when another woman walked in with her phone, which had just died. I noticed there was a plug at the bar, so I offered to take her there. She followed me and was especially friendly about it, and after plugging her phone in, we kissed passionately and looked around for somewhere to get comfortable. That turned out to be the other lounge room, which was basically the first open room she saw, before she pulled me down and leaned against me, moving my hands under her bra. There wasn't even time to get her clothes off, just grabbing, pinching, sucking and a substantial amount of moaning on her part. I do love it when someone's vocal, and she only stepped it up after I reached down her pants to rub her clit and finger her soaked pussy. She reached back and grabbed at my hardening cock through my jeans, but she never tried to handle me without my clothes in the way.
Not that I really cared, though. I just wanted to get her off and get somewhere more horizontal. Eventually, she turned onto her side and pulled down her jeans to offer me her ass. I thought she wanted me to spank her, but a couple of hard smacks indicated otherwise. Instead, I reached under her to slide my fingers back into her pussy, which she appreciated rather clearly. After a few minutes, she pulled away and wanted to check her phone. I walked with her back to the bar, where she found some other guy who was her shiny new toy. I confirmed that her phone was still there and excused myself to try and find Carrie to tell her that I was pretty sure I just got used… and it was awesome. My nerves were gone, replaced largely by lust.
There she was, in one of the play rooms with a couple of her friends and Lisa, who was one of the people I had talked to about the party. I knew that Lisa, much like Carrie, would be a bit on the shorter side with a heavier build. In other words, just my type. However, it wasn't until I saw her that we exchanged some awkward introductions through usernames.
We finally made our proper introduction with deep kisses, hungry tongues and hair pulls. Everyone else left the room, I closed the door and pushed Lisa down on the bed. I don't even recall if she took her hat off or it just came off when she pulled my pants off and devoured my cock with her mouth. I'm about average length, and while I'm told I'm especially thick, I don't really have much basis for comparison. Only two people had ever completely deep-throated me, but Lisa added her name to that list with almost no effort on her part. She greedily sucked my cock like she had been waiting for it all her life, but I stopped her to put on a condom and fuck her properly.
I'm sure they had condoms available somewhere, but I brought some just in case I couldn't be bothered to look hard enough. Condom on, everyone's clothes off, some quick licks of her soaked pussy and I entered her with basically no resistance. Lisa moaned into my mouth as I thrust with about as much coordination as I could muster, especially considering how wet she was. I've never really done well with condoms, and between that and the beer I was finding it a little hard to stay… well, hard. I took the condom off so she could give me another fantastic blowjob, then she wanted to ride me. After confirming she also has a recent clean test on file, she climbed on top of me and rode me enthusiastically, lowering herself so I could suck on her beautiful, long nipples. Lisa loved that, as well as when I grabbed her by the shoulders and thrusted in her with all my might before coming harder than I have in some time.
(As an aside… yes, I know, risky. But I'm going to get tested again soon and I only lost the condom when it was clear we were both clean, protected in other regards and that the condom was substantially inhibiting our pleasure.)
We cleaned up a bit, got dressed and made our way back to the main room, where the dance-off… still hadn't started. We hung out some more, making some friends with other women with kisses and whipped cream before Lisa grabbed my hand and we tried to find another room to kill some time with orgasms. Most of the play rooms were closed, though, and the only one that was open already had occupants. Open doors mean company is invited to watch, so we did, moving further into the room to watch a woman on all fours, getting fucked while sucking off another guy.
(Interjection: I've had a fantasy to watch people, and I've also been thinking more about threesomes involving other guys. I don't think I would mind not being the only man there, but you never truly know until you try.)
Eventually more people came to the room and we moved further in against the wall. Another couple walked in to another corner to watch, while Lisa and I kissed and fondled each other watching the threesome. I suggested to Lisa that she should probably suck me again, especially considering her gift for it, and she did while I watched things in front of us proceeded somewhat shakily. Eventually, the threesome ended, and Lisa and I got ourselves back together to watch the dance contest.
Only a handful of people took part, and although our whipped cream friends tried to suggest that I join in (it wouldn't be my first time on the pole and I think there's international treaties against me doing it again), taking full advantage of my snap-button shirt (like I said… overthinking my clothes). Carrie had nothing to worry about with her dancing, as everyone enjoyed the show. We made our way back into the crowd, socializing and fondling until I lost track of Lisa. Later on, I found Carrie in one of the play rooms, talking to one of her friends. Carrie asked me to wait in the room until she could find someone else, but finding him indisposed, joined me in the room and closed the door.
It was familiar, and yet so different. We hadn't had sex together in over 10 years, but it was almost like we didn't miss a step. Although we had changed in some regards, like how Carrie discovered she can squirt.
A lot. Both in quantity and frequency.
Before I even got to enter Carrie, she had me finger her, switching between rubbing her clit with my thumb, her G-spot with her fingers or a combination thereof. That did the trick, and the sight and feel of her coming harder than I had ever seen was one of the most beautiful sights I can recall. Clean tests, birth control and years of trust from our relationship meant we could enjoy each other without other precautions. However, despite the anticipation, the alcohol and fatigue was too much for me to maintain an erection. Shifting positions as I had with Lisa, going from missionary to doggy to cowgirl, was fun, but the inevitable was upon me. I still enthusiastically used my fingers, mouth and tongue on her pussy and asshole, exploring her all over again until she had soaked the towel and sheets. If any of us had been keeping track of her orgasms, they all washed together.
We cleaned up again, changing the sheets and heading back to take in the stragglers who hadn't already called it a night or taken their adventures elsewhere. That involved two women heading to a bench in a hallway and grabbing a double dildo, attempting to fuck before switching to a strap-on. I don't know where they still had the energy, or how they knew watching two women have sex was another of my biggest unfulfilled fantasies before that night, but I was not disappointed. Neither were they or their other observers. After they finished, people started to disperse, promising to meet up again soon. That included me, Lisa and our whipped cream friends. Lisa had apparently kept herself quite busy in the meantime, and I vowed I would see her again. So did the other friends, and now I have another wave of anticipation cresting. I hope my first time won't be my last time, but it was everything I could have imagined and more.
(Editor's note: of course names have been changed. Names were not omitted in the interest of privacy or anything. If I didn't name anyone, it's because I never got their real name.)
Source: reddit.com/r/gonewildstories/comments/3xjq8e/move_to_a_new_city_join_the_swing_set_mf_mf_mf