Chapter 9: Cheater

-- SUNDAY, APRIL 26, 2005, JUNIOR YEAR --

“Have you ever thought about double-penetration?” I asked quietly, holding my girlfriend in my arms as we both enjoyed the afterglow of orgasm. Esther was sweaty and naked, her head pillowed on my chest while my sperm slowly soaked into her womb.

The two of us were alone today. Sarah didn’t join us for ALL our sessions, maybe half. And then there had been that time Esther opened the door and I walked in to find redhead Kate Mosely in a sixty-nine on the bed with Sarah too. But the point is: while my girlfriend certainly enjoyed sharing me with her friends and likewise loved to get sandwiched between me and a hot girl, Esther and I had made a point of finding quality one-on-one time together as well.

She had that electric tingle up her spine for me too, after all.

But while we’d had many threesomes (and that one foursome) together, thus far we had only done so with other girls, and Esther picked her head up to look down at me with a frown. “Double-penetration meaning ... Wait, is this your way of asking me if I’ll let you fuck my ass?”

Her tone made me instantly go on the defensive, and I gave her an apologetic look. “No, no. I mean ... I’ll admit the thought has occurred to me and-- Okay that look on your face says it all. I’m shutting up now.”

I closed my eyes and grimaced. Me and my stupid mouth. Being myself only worked up to a certain point, I supposed.

“Well don’t think I haven’t noticed you starting to feel around back there while you’re going down on me,” Esther muttered.

“And you’ve promptly squirmed away every time,” I replied, opening my eyes again to look up at her. “I actually didn’t mean to suggest anal sex to you. It was a poor choice of words.”

“I’m not actually bothered by the suggestion. I mean, we kinda HAVE done everything else a man and a woman can do together with just oral and vaginal sex.”

“But you’re not particularly interested in anal.”

Esther made a face. “Just seems ... messy. And kinda gross...”

I nodded. “Understandable.”

“I take it you’ve had - and enjoyed - anal sex.”

“Only recently.”

Esther’s eyes narrowed. “HOW recently?”

I immediately blushed and averted my eyes. “Uh, didn’t we agree not to talk about our former lovers?”

Esther rolled her eyes, not convinced. But she sighed and shrugged. “Sorry, Bert. Not my thing.”

“That’s fine. No pressure. And like I was trying to say, I didn’t actually intend to suggest anal sex.”

“Then what WERE you suggesting?”

“I was wondering if you ... uhhh ... well...” I hesitated, blushed, and then finally just started, “Well you know that last time when you were on your period and you didn’t want me going inside you?”

“I told you: I don’t like messy, and the thought of my menstrual blood on your dick is NOT a turn-on.”

“Fair enough. What I meant, though, was how you still wanted to give me a blowjob, and at the same time you had Sarah pumping a dildo in and out of you.”

“Dildoes are easier to clean up.”

“True enough. My question is: Did you enjoy that? Did you enjoy feeling me cum in your mouth while a big dick was pumping in and out of your pussy?”

Esther’s eyes narrowed again. “Are you actually suggesting what I think you’re suggesting?”

I took a deep breath. “I just mean ... fair is fair, right? You keep giving me threesomes with Sarah ... and even Kate that time.”

“Kate wants a repeat, by the way. I was thinking Friday, assuming you’re alright with it.”

My eyes bugged out. “Um ... okay ... I mean of course I’m fine with it, but you’re kinda proving my point. In any case, I was wondering if ... like maybe ... you’d want a threesome with another guy.”

Esther frowned. “You want me to have sex with another guy?!?”

There was such an immediate tone of disgust in my girlfriend’s voice that I immediately felt apologetic again. “I’m not ASKING you to. More, I guess I was kinda ... offering? Like ... wondering? Wondering if you wanted?”

Gosh I sound like such a whiny bitch right now. Get it together!

Esther frowned again and repeated, “You want me to have sex with another guy?!?”

I shook my head immediately, assuming that was the reaction she wanted. “I was just trying to state a willingness to consider the option if you were interested in a threesome with another dick involved. Fair is fair. I’m really falling for you, and I want to make you happy, and we’ve had these threesomes with other girls and I didn’t know whether or not you had given much thought to double-penetration--”

“I don’t want your dick or any other dick forcing open my ass.”

“Fair enough. But even to give a blowjob while you’re being fucked or something.”

“Sarah with a dildo worked just fine in that regard. I don’t need anything more than that.”

“Okay sure, no problem. Forget I ever said anything.”

“You’re a really weird guy, Bert.”

“I’m sorry.”

“No, don’t apologize.” Esther took a deep breath and collected herself. She pursed her lips together and seemed to be working things around in her head. And after a long pause, she exhaled and continued, “I appreciate you trying to think outside the box a bit for ways to make me happy. I love that you’re a considerate boyfriend, even if I think it’s a little weird that you wouldn’t be jealous of me fucking someone else’s dick.”

“In all fairness, I’ve already watched you sucking Ben and Jaron’s dicks.”

Esther frowned. “But that was different. That was a blowjob party with my sorority sisters in the Chapter Room before you and I were together.”

“Yeah, I know, but still.”

Esther seemed to muse on that. “You’d actually be okay with me fucking either Ben or Jaron?”

I bit back the sour taste that rose up in my throat. The expression that resulted must’ve been answer enough.

“See, you don’t like the idea.”

“I just...” I hesitated, unwilling to state that both Ben and Jaron made me feel ... inadequate: Ben for being a Sex God and Jaron for being a fucking Greek God. No way would I ever seriously want Ben going anywhere near my girlfriend. He’d ruin her and I’d never be able to satisfy her ever again.

Esther was already shaking her head. “They’re hot guys and all, but no, Bert. You’re all I need.”

“Thank you for that, but at the same time, if it would make you happy...” I took a deep breath, my stomach feeling queasy again. Only this time, it wasn’t because of Ben. “And besides, you’ve been really permissive about me with other girls so far.”

If she only knew ALL of the girls I’ve been with since we got together.

Esther waved me off. “Sarah’s my big sister and Kate is one of her best friends, so I’m doing THEM a favor by sharing you with them. And I’m not gonna pretend I don’t enjoy their tongues on my clit while you’re fucking me.”

“Lucky me.”

Esther shook her head. “I don’t need you letting me fuck other guys in the name of fairness. Not Ben. Not Jaron. I’m perfectly happy with what we have. You, me, Sarah ... maybe Kate ... This is all I need. Alright?”

I force a smile and nodded. On the outside, I was a happy and content boyfriend.

But on inside, I was dying.

I had started this line of thinking and asked about Esther’s thoughts on double-penetration hoping that maybe she’d be interested in a threesome with some other guy. That way, I would feel less guilty about the stuff I’d been doing in secret.

What I was doing was wrong. I knew that. Esther and I were still early in our relationship. Up until now, we’d never actually talked about the subject of fidelity or exclusivity, so from one point of view, you could say I hadn’t actually done anything wrong since she’d never explicitly told me I couldn’t fuck other girls behind her back.

Of course I knew that was utter bullshit. Once a couple starts calling each other boyfriend and girlfriend, I understood that fidelity was implied. Now maybe if I had been screwing around with Ben and Dawn in those first couple of weeks before Esther and I agreed to our new titles, I could’ve argued that we hadn’t committed to each other yet.

But that time was long since passed. There was no beating around the bush on this one: I was a cheater.

And I didn’t like that thought.

But I couldn’t stop myself.

Dawn was ... well ... she was fucking Dawn. She wasn’t even my type, but there was no denying she was a goddess on Earth. She called, and I answered. I couldn’t resist her. I couldn’t deny her. She was absofrigginlutely incredible and...

... well...

... I couldn’t resist her.

So when she’d asked me to join her for a triple-penetration with Ben, Jaron, and Carli, I hadn’t been able to say no.

I probably should’ve said no to Andie Holland. I hadn’t been expecting the perky bottle-blonde to join in, although she did balance out our three-guy/three-girl ratio. But she could suck dick like a dream and in all honesty, I never even tried to turn her down. The next thing I knew, the petite girl sat in my lap with my dick buried all the way up her cunt while Dawn and Carli made out with each other with Dawn riding Ben reverse-cowgirl and Jaron pumping Carli from behind.

Triple-penetrating Dawn had been a dream.

And then Andie had wanted to go next.

And then Carli after that.

It had all been absolutely incredible at the time.

But that was last night. Today was today.

And I was a cheater.

I HAVE to tell her.

There was no way I’d be able to live with this guilt. Now maybe if Esther had been inclined to have a threesome with another guy ... Fair would be fair, right? But that last-ditch effort had already failed.

Maybe if I’d had the balls to just tell Esther from the beginning that Ben had asked me to be the second dick in a threesome with Dawn ... I mean, Esther had been pretty cool and understanding overall. Hell, we’d met at the fucking Tri-Delt Blowjob Party. I’d already seen her give blowjobs to Ben and Jaron, and she’d seen Dawn and all her friends give blowjobs to me, right?

As for Andie and Carli, Esther had previously told me that as Tri-Delts, sharing with each other was baked into the sorority code, right?

I had to come clean. I had to admit the truth before it spiraled into something worse. I had to strike while the iron was hot, because the longer time passed between that insane six-way last night with Dawn, Carli, and Andie, the worse it would get. Better to confess sooner than let too much time go by and make it seem like I was trying to cover it up.

“Hey, you alright?”

My girlfriend’s sweet voice shook me from my doldrums. I blinked and looked up at her, belatedly trying to smile. “Uh, yeah, sorry, distracted there for a minute.”

“What’s wrong?”

“It’s...” I took a deep breath, exhaled slowly. “There’s something I have to tell you.”

Before I could continue, there came a knock at the door, followed immediately by Sarah’s voice. “Esther? You in there? We need to TALK.”

I felt a chill run down my spine. Sarah’s tone of voice was MAD. I didn’t know for sure her anger was about me, but my guilty conscience told me it was.

“Can it wait?” Esther called back. “I’m kinda busy!”

“I know! And no, it can’t wait!”

Esther sighed, rolled her eyes, and rolled off the bed. She grabbed a t-shirt - my t-shirt, actually - and quickly pulled it on. Still, she hid herself behind the door as she cracked it open about six inches. “Hey Sarah. What’s going on?”

I couldn’t see Sarah from my vantage point, but I heard her voice state with icy coldness, “Your boyfriend is a fucking cheater. THAT’S what’s going on.”

I never did get my t-shirt back.

The tears were still wet on my eyes when I burst into the house and hollered at the top of my lungs. “BENNN!”

He wasn’t anywhere in the living room, so I headed straight for the stairs. The wood treads banged loudly as I thundered up them. After going straight to Ben’s master bedroom, I flung open the closed door and took two steps inside, my head jerking left and right in a quick scan before determining he wasn’t in his bedroom either.

Kim’s bedroom door was closed and I flung that open as well, so hard that it banged against the adjoining wall. I saw my friend sitting up in bed, the blankets pulled to his waist. Enraged by the mere sight of him, I pointed my finger at my so-called-friend and growled, “Dammit, Ben! This is all your fault!”

He raised his hands defensively. “Whoa, whoa. Slow down, Bert. What the heck’s going on?”

“It’s all your fault, man! I had a good thing going. I was happy, maybe even falling in love. She was perfect for me. Not too experienced, not so heartbreakingly gorgeous that I would feel unworthy of her. She’s even Korean! My parents would have loved her!”

“What the hell are you talking about?”

“Esther!” I yelled. “She dumped me tonight and it’s all your fault!”

“What? Why? How?”

“Fucking Carli! Or Andie! Or ... I don’t know! Somebody told her about our little sessions with Dawn!”

He looked confused. “Wait ... uh... you didn’t tell her?”

“Tell her what?” I scoffed. “That you and Dawn asked me to have sex with you guys? Hmm ... let’s think about this ... I’ve just started dating a sweet girl who’s a little inexperienced when it comes to sex. Yeah, why don’t I tell her my best friend and his fucking-more-beautiful-than-the-sun girlfriend want me to have a threesome with them? Yeah, that’ll go over well.”