Chapter 5: Confidence

-- APRIL 17, 2004, SOPHOMORE YEAR --

“You ready for this?” Ben glanced over at me across the roof of my car when I stood up from the driver’s side.

“Locked and loaded.” I grinned wolfishly.

“Does that mean what I think it means?”

I just smiled and strode forward: head erect, chest out, doing my best to carry myself as confidently as I could.

I didn’t actually feel very confident inside. Ben had invited me along to be his wingman to some party. He said he’d never been there before and barely knew the guy, so he’d appreciate not having to walk into a strange place alone. I, of course, had nothing better to do, so I’d been quick to agree. So I drove up from Fremont, picked up Ben from his place, and followed his directions up and into the Berkeley hills.

I’d been surprised to find an isolated mansion at the end of a cul-de-sac with a dozen cars already parked in the driveway and along the curbs. When Ben had told me he’d been invited to a house party, I’d been thinking of the few house parties I’d been to in high school - you know: three bedrooms, a medium-sized living room, and maybe a decent backyard. But this place turned out to be huge.

There was an infinity pool built on a massive redwood platform that looked like the water would just cascade over the side of the cliff onto the city below like some kind of spectacular waterfall. The house looked big enough from the outside, and that was BEFORE I realized it was only the top floor of a multi-level mansion with the additional floors going downstairs another couple of levels. And as soon as Ben and I walked in, my first thought was, We are in WAY over our heads.

As I said, I didn’t actually feel very confident inside, but Robin had instilled in me the need to project a confident demeanor regardless. Fake it ‘til you make it or something. Still, I felt my eyes going wide at the scene before me and my chest sagging at the realization that the guests were ... well ... actual grownups ... not college kids like me and Ben. But rather than let that knowledge set me back, I took a deep breath, collected myself, and flashed Ben a smart-ass grin.

“Let’s hit it,” I told him rather cockily.

He looked at me like I’d turned into that alien from another planet come to have intercourse with Earth’s females. And with that in mind, I flashed him the Vulcan salute.

Ben snorted and nodded us forward.

To my surprise, there was a very high female-to-male ratio, around 3-to-1. The women were gorgeous, with elaborate makeup, expensive jewelry, and clad in slinky cocktail dresses, not college hoodies or jeans. Nobody was dancing, and the music was down-tempo. I started scoping out some of the hotties, and I had just zeroed in on exactly the kind of cute, slender, dark-haired girl I usually favored when our host came to us.

“Prince Charming! You made it!” A handsome dark-haired man about six-foot-three was suddenly clapping Ben on the back. Dressed for a nightclub with slacks, a tailored shirt, expensive “bling”, and a Rolex watch, he carried himself with the kind of suave confidence I knew I should emulate. And I rather self-consciously found myself copying the cool, collected way he slouched without appearing to slouch.

A moment later, he turned to me and proffered his hand. “Carter Sheridan. Welcome to my house.”

“Bert Kim,” I replied. “Nice digs.”

Carter waved dismissively. “This is nothing. You should see my parents’ place.”

I mentally noted the way he accepted the compliment while simultaneously bragging. I knew this was the kind of ‘bad boy’ some girls liked, and I found myself admiring him. I mean, I already respected Ben’s utter calm in front of a beautiful woman, completely secure in the knowledge he could bed down with wicked hotties any time he wanted, but Ben wasn’t what anyone would describe as a “ladies man” in terms of his social skills. He wasn’t the kind of smooth operator this Carter guy clearly was.

A minute later, Carter led us over to a group of six girls seated in a circle around a table on which an expensive-looking hookah had been placed. “Gentlemen, allow me to introduce Zoë, Beth, Jillian, Tasha, Nikki, and Madison. Ladies, I’d like you to meet Prince Charming. He’s a special friend of mine.”

“Prince Charming?” queried the platinum-blonde with heavy eyeshadow.

“Well, you can call him ‘Ben’,” Carter shrugged. “And the handsome devil in the red shirt is Bert.”

“Bert and Ben,” giggled the redhead - I think Carter had introduced her as Nikki - as if our names starting with the same letters was somehow really funny. Her mirthful expression made me smile, although I wondered just what was in the hookah. I had to guess it wasn’t tobacco.

“Well I like ‘Prince Charming’ better,” the platinum-blonde replied and started making goo-goo eyes at Ben while thrusting up her cleavage at him.

“You be careful around Jillian. She’ll eat you alive,” Carter warned as he reached over and patted the blonde’s knee. “But then again, I think that’s exactly why I brought you here. You dig blondes, right?”

Ben eye-fucked Jillian for a moment but diplomatically replied, “I dig all kinds.”

“So does Carter,” another blonde (Tasha?) giggled. She had pulled Carter into her lap and now rubbed his leg. But then the blonde reached out and slapped the leg of the girl next to her, adding, “Of course, the brunettes have most of the fun.”

The brunette had been the cute, slender brunette I’d first laid eyes on. She grabbed the business end of the hookah and proffered it over to Carter. “Want a hit?”

“Sure thing.” Carter leaned forward and sucked on the pipe. He closed his eyes, really absorbing the sensations, and again I found myself figuring there wasn’t tobacco in the hookah. And when he pulled back, he glanced up at Ben. “Charming?”

Ben shrugged and took a hit off the hookah. He seemed no worse for wear, so when he passed it off to me, I took a deep breath to calm myself and started inhaling.

I could tell from the ambient smell we were smoking weed, but I’d never done so before tonight so had no idea how I’d actually react. But after a few rounds, I really started to feel a LOT more chilled out.

Platinum-blonde Jillian had definitely taken an interest in Ben. I had started flirting with dark-haired Madison, but when Carter got up, she went with him and never came back. I supposed that made sense since the girls made clear our host had a thing for brunettes.

But that was okay. I was doing my best to be a constant chatterbox, complimenting the girls and talking about whatever the heck popped into my head, whether it be Earth’s place in the Universe (which fascinated redhead Nikki) or European politics (which Ukrainian-born Tasha got really into). Nikki started doing all the stereotypical things girls do when flirting: giggling constantly, rubbing my arm and chest, and playing with her hair. Tasha sat on my other side rubbing my leg. Somehow we started talking about sex, and the next thing I knew, I started talking about me, Ben, and another guy having a crazy six-way swapping party with three really hot girls, which REALLY piqued Nikki’s and Tasha’s interested. Thankfully, I’m dead-certain I didn’t name any names except for me and Ben.

The next thing I knew, Nikki was in my lap shoving her tongue down my throat while Tasha was nibbling on my ear, whispering dirty thoughts about me taking them into a bedroom together so we could re-enact some of the stuff I’d done during that six-way. And I found myself thinking...

Huh, this fake it ‘til you make it confidence thing really does work.

“Ohhh... fuck,” I grunted, reclined against a few pillows and braced against the headboard of some guest room with Nikki’s big tits in my palms as she undulated herself on my embedded dick.

The redhead laid back against my chest face-up, her feet planted atop my spread thighs. The position allowed blonde Tasha to lay down between our legs, licking her friend’s clit and occasionally dipping lower to tongue my balls.