Chapter 3: The Swingers Game

-- DECEMBER 2003, SOPHOMORE YEAR --

“Are you sure you two want to do this?” Dawn asked seriously, looking back and forth between me and my girlfriend. “Nothing will ever be the same again.”

That’s kind of the point, I thought immediately, squeezing Robin’s hand. Robin had been the one to find the swingers game in some shop on Telegraph, and when she brought it to me and Gwen with the idea of playing with our friends, I admittedly had been immediately intrigued.

I owed a lot to Robin. She’d been my first lover and had taught me so many things. She’d been a great girlfriend, no question: loyal, affectionate, sweet, but I couldn’t say we were in love with each other. She’d never even said the words “I love you” to me. Rather, we’d found comfortable companionship and a regular source of physical pleasure. Being in the same circle of friends, it was important that we got along with each other, which we did. We had similar temperaments, would have big fights but then be equally eager to make up, and were more or less compatible in the bedroom.

We’d also fallen into a rut. We’d been together for over a year now, and while our relationship had always been fine, we’d never scaled the heights of romantic passion that made poets weep or anything like that.

From the beginning, I had wanted to believe that our love would grow into the kind of undying devotion and affection that would put us on the path to Happily Ever After. I had wanted to believe that our initial lust for each other could grow and mature and become the kind of lifelong bond that would last for all eternity.

But it hadn’t. In hindsight, I wondered if we hadn’t gotten together for the wrong reasons. I wondered if we hadn’t gotten together precisely because ... well ... because we both wore glasses.

Okay, that’s a metaphor. Robin and I hadn’t gotten together because we literally both wore glasses. But much like all those teenage rom-coms, those glasses had been a short-hand metaphor for being ... plain. Gwen had spotted it from the beginning: Compared to Ben, Ryan, Adrienne, Dawn, and Gwen - Robin and I were the ugly ducklings of the group. Didn’t it make logical sense that the least empirically attractive members end up together? Of COURSE the plainish Robin would end up with geekish Bert. I could never dream of landing a buxom sexpot like Adrienne, Dawn, or Gwen, so I might as well set my sights on someone ... achievable ... like Robin, and vice versa, right?

Don’t get me wrong, I had genuinely liked Robin from the beginning, and she had liked me: there was no question about that. But how much of that was the two of us deciding we didn’t have a snowball’s chance in hell at landing someone ... hotter?

Robin had admitted to me her lustful attraction for the other guys in our group. Having spent a year and a half in Ben’s orbit, I knew she harbored some curiosity about what made him “soooo damn special” (it was a phrase she’d wondered aloud more than once). Additionally, I knew she viewed Ryan as a well-built specimen of man.

And to be perfectly honest, I wouldn’t mind having sex with the likes of Dawn, Adrienne, or Gwen. I mean ... come on...

It was with that idea in mind that I found myself staring up at Dawn, imagining her without any clothes on, and I breathed rapturously in answer to her question about whether or not we were sure we wanted to do this, “Yeah...”

Robin was actually more excited than me. She stared with open lust at Ben and Ryan, nodding as she stated with obvious excitement, “Oh, yeah.”

Ben, however, apparently had no clue what was going on. Not a big surprise because (A) the girls seemed to take perverse delight in keeping him in the dark about this kind of stuff, and (B) he could be as dense as a concrete brick sometimes.

In the end, the girls talked him into going along with the game, and the next thing I knew, the six of us were assembled in couples, with Ben and Gwen paired up to start.

The game started off tame: make out with your partner for one minute, remove a major article of clothing, stuff like that. But then it came time to spin the “Swingers Wheel”, which got us all to switch partners.

And I got switched to be with Dawn.

Now I’ve already made clear my personal preference is for the cute, slender, dark-haired type - call it a stereotypical influence of growing up Asian or whatever you want. But that didn’t mean I didn’t appreciate the raw sexual appeal of a busty blonde beauty, and Dawn most definitely qualified for all three of those descriptors. She was tall, she was exquisite, and I’d be a bald-faced liar if I ever tried to claim I’d never fantasized about fucking her. I mean yeah, I’d always thought the idea was a complete pipe dream - not least because she was Ryan’s girlfriend and Ben’s best friend - but that didn’t mean I couldn’t dream. And when Robin had first proposed we actually play the game, as much as I had lusted for Gwen as well, it was the idea of getting an opportunity to be with Dawn that made me say ‘yes’.

I admit I got a little overeager the first chance I got to make out with her. I couldn’t help trying to get my hands on her tits, and she had to deflect me like a high schooler on a first date. I apologized profusely and tried my best to calm down, but it wasn’t easy. Dawn was fucking hot. When one of the cards told her to fondle my crotch, I nearly lost my load.

More clothes came off. More drinks were drunk. More kisses were exchanged. By the time we were all naked, Robin was paired up with Ryan dry-humping his dick trapped between their bellies and her tongue in his mouth. Quite honestly, Gwen and I were going at each other with similar enthusiasm. While perhaps not as model-pretty as Dawn, she was still an extremely attractive and sexy young woman with a boner-inducing figure that had been the star of many of my fantasies. To have a self-described slut like her eyeing me hungrily was definitely a new experience for me, and I relished in tasting the dirty-blonde’s big tits while Gwen laughed and patted my head.

At Level Three, the fifth card read: Orally pleasure your partner for five minutes.

By now the Swingers Wheel had spun Robin and I back together, and that was the first time my girlfriend showed any hesitation to continue. Robin reached out to squeeze my hand and asked, “Are we really doing this?”

It wasn’t a question about whether or not she could give me a blowjob. It was a question about whether or not I could handle my girlfriend giving someone else a blowjob, and vice versa.

I honestly didn’t know what to think. I mean, obviously the thought had crossed both our minds before we actually started playing the game, so it wasn’t like we didn’t know things would be coming to this point. But perhaps both of us had been ingrained by society to believe romantic relationships were meant to be monogamous and that anything outside of that would be considered “cheating”. And yet, here we were.

I liked Robin. I liked her a lot. As I said, she’d been a great girlfriend, my first in many ways. Like, I’d gone on a few dates in high school that never really went anywhere, hence my virgin status coming to college. I still remembered that first blowjob Robin gave me in her Snow White costume after Halloween. I still remember her patiently teaching me how to lick her pussy and suck on her clit until she orgasmed. I still remembered the night we first made love: I’d been nervous as hell, but she’d soothed me and stroked me and didn’t make me feel bad for busting my nut inside her awesomely tight pussy in less than three minutes.

We weren’t in love - that much was clear. We were comfortable and content, comfortable enough to last more than a year. But it had become clear that we weren’t each other’s endgame and that it would soon be time to move on. So there wasn’t any jealousy or possessiveness, for either of us. I knew how badly she wanted to ... well ... find out if Ben really did have a magic dick that could give her the glorious coital orgasms I could never quite give her. I knew she wanted to ride Ryan’s hunky manflesh.

And I knew I wanted to find out if having sex with Dawn and Gwen would be as incredible as it had been in my fantasies.

So Robin and I had shared a look, the kind of shorthand look old lovers like us could use to express ideas without needing to use words. Robin pushed her glasses up the bridge of her nose, blushed pink, and nodded. “I’m ready.”

A few minutes later, Robin was squealing and screaming in orgasm as Sex God Ben went down on her. Unfortunately, I wasn’t doing quite as great a job giving cunnilingus to Dawn. I was getting in my own head a bit again, nervous as hell, and she had to sort of guide me a bit.

And then we got to Level Four.

The first card read: Fuck your partner right in front of everyone.

[SLAM!]

[THUMP!]

“Oof!”

Robin had shot out of her seat like a rocket, tackling Ben onto the floor between the couch and the coffee table. She was almost frantic as she tried to impale herself on him while he tried to calm her down and get all the pieces properly lined up. And when they finally got him inserted, she cooed while sitting herself down.

I didn’t feel an ounce of jealousy. I was happy for Robin. I knew she wasn’t in love with the guy or anything, but she’d spent the last two years or so wondering just what the fuck made Ben soooo freaking special. She had been curious, that’s all, and now she’d finally get the chance to see what all the fuss was about.

“So fucking BIG, Ben!” my girlfriend groaned.

Okay that part is a little emasculating.

But I didn’t have time to dwell on that. See, I got to be with Dawn, and I only had eyes for her. Quite possibly the most beautiful woman I had ever laid eyes on - at least empirically - she was even more incredible naked, and oh my god did she know it. She preened, just for me, letting me drink in every last inch of her exquisitely gorgeous body.

And I was gonna get to fuck it.

After everything we’d done tonight, both of us were horny as hell and in a hurry to get cock inserted into vagina. I was hyperventilating and pinching myself at my good fortune and perhaps a little overeager. But rather than let me climb on and just start rabbit-fucking her (not that I would’ve actually been so crass), Dawn wanted to be on top and I was happy to let her. She pressed her tits to my face and I know I got pretty wide-eyed, but before she actually impaled herself on me, she grabbed my head and looked into my eyes.

“Hi, Bert,” she greeted me sweetly.

“D-Dawn...” I moaned, unable to believe this was really happening. I’d had sex with exactly one girl my entire life: Robin. Sure, I imagined that someday ... eventually ... I might have sex with another. But Dawn? DAWN???

Absolutely unreal.

My expression of wide-eyed wonder must’ve worried her for a second, and she asked a little nervously, “We’re just friends, right? We can handle this, right?”

I nodded hurriedly, eager to show her I wasn’t like gonna fall head over heels in love with her or anything like that. I just wanted IN, and I insisted. “Of course.”

I didn’t think my answer was very convincing though, and apparently it wasn’t. She looked skeptical, perhaps recognizing that I really, really just wanted in and would probably say anything necessary to do it. So she paused and asked, “We’re not gonna be weird with each other after this, are we?”

Knowing my big opportunity to have sex with Dawn quite possibly depended on me assuring her that we wouldn’t be weird after this, I took a deep breath and regarded her seriously. And in a calm voice, I stated sincerely, “Dawn, we’ll be cool. Just friends.”

She gave me a wolfish smile, spread her thighs, and sat down.

I watched, rapturous, at the sight of her beautiful freshly-shaven pussy sinking down around my dick (MY dick!!!), and as soon as she had captured every inch, I lost my cool. “Holy SHIT!” I squeaked in disbelief, my eyes once again going wide.

And then I tried to grab her hips and start rabbit-humping her.

“Calm down, Bert,” Dawn told me quietly, her tone just a little scolding but with a mirthful twinkle in her eyes as she held my shoulders and slowed herself down.

“Sorry,” I apologized. “I just ... I can’t believe we’re doing this.”

“Believe it.” She took up a more sedate, undulating rhythm.

“I can’t. I mean ... you’re just so ... so...” I paused and took a deep breath. “You leave me speechless. You’re a goddess, and I’m a mere mortal.”

Dawn giggled. “Thank you for the compliment, but I’m only human.”

“Don’t be so modest. You’re absolutely incredible. You’re ... you’re ... I can’t find the words. You’re out of my league and we both know it.”

She giggled again, trying to be humble but quite obviously pleased by the praise nonetheless. “I’ve never been out of your league,” she told me gently. “You’re worth more than you realize. You just need to have the confidence in who you are and what you can bring to a relationship.”