Helping Sean

“Is this going to work?” I glanced over at Sean and frowned. He was pacing nervously back and forth. I wanted to reach out, grab him, and force him to hold still. Him being nervous was making me nervous--especially annoying since I had no reason to be. Wasn’t even sure why I was standing here in the first place. I mean, I knew why I was here. I was helping Sean ask Sarah out. Apparently my desire to distance myself from this hadn’t worked. Sean was surprisingly timid about the most random things. He had no problem going up to the girls around school and ask if they wanted to fuck, but asking a girl out on a date? Paralysis. I’d told him what Kaylee said over a week ago, and he had only now worked up the courage to try and ask her.

Normally, he’d go up to a girl and ask regardless of the group of people she was with. Not this time. He wanted to talk to her alone. Which was how I’d been roped into all this.

“No idea.”

“You don’t know?”

“Course not.”

“I thought you said she was interested.”

“I said Kaylee told me there was a good sign she was open to dating. She even managed to get Sarah to admit there were guys she was interested in.”

“And I’m one of them?” I shrugged. “Man… I’m so nervous.”

I glanced over at him in disbelief. Already, envy was creeping over me. What the hell did he have to be nervous about? He had the body of a Greek god and the face of a model. I was working out with Mr. Webb and Liam now, but it would be a long time before I got anywhere close to him--if I even wanted to get to that level. He probably had a higher partner count than even Kaylee, and a reputation that only attracted more. Yes, he came off as a bit of an airhead at times, but that only seemed to work in his favor. He had a far better chance of Sarah accepting his date invite than Kaylee and I had back when we were still friends.

“You’ll be fine,” I said. Looking down the hall, I saw the familiar face that brought a smile to my face. Kaylee looked as good as always in her skirt and blouse. The tall blond beside her was a beauty in her own right, but she didn’t have anything on my girlfriend. “Here they are. You ready?” He looked like he was ready to hyperventilate. “Sean?”

“R-ready.”

“Come on then,” I said, stepping away from the wall and heading down the hall with Sean beside me. I was glad the plan seemed to be going well this far. Kaylee had managed to get Sarah alone. All that needed to happen now was us ‘bumping’ into each other and me pulling her away for a moment. That would leave Sarah alone with Sean long enough for him to ask her out.

That was the plan at least. Sean looked like a man destined for the gallows. Well, it was too late to back out now because it was go time.

“Kaylee!” I said with a smile. “There you are.”

“What’s up?”

I glanced over at Sarah. “Can I borrow you for a moment?” I asked as I turned my attention back to Kaylee.

“Uh… sure?” she looked over at Sarah. “Mind waiting for a bit? I’ll be right back.” Sarah didn’t say anything back, answering with a nod. Classic Sarah.

We got a dozen steps away before Kaylee leaned my way. “That went well.”

“Perfectly natural,” I agreed. Stepping around the corner, we both immediately turned and peeked back down the hall.

“Think he asked her out yet?”

“Hmm. No.”

“How long should we give them?”

I thought for a moment. “A minute or so?”

We watched in silence as the two stood awkwardly next to each other. Sean was focusing on something on the ceiling. Sarah seemed as shy as ever. It was hard to see at this distance, but I think she was blushing. That was a good sign… right?

“I bet you a blowjob he chickens out.”

I blinked, glancing at Kaylee. She had a mischievous grin on her face.

“If I lose?”

She thought for a moment. “You sleep with Ellie.”

I did a double take. “W-what?”

“You heard me.”

I shifted uncomfortably. “Wouldn’t that be a win-win for me?”

She tilted her head slightly, raising an eyebrow. “Oh? Interested?”

Wrinkling my nose, I shook my head. “No thanks.”

“Only you would turn your nose up at the opportunity to bang a smoking hot girl.”

“Well I already have a smoking hot girl to please, and she keeps me plenty busy.”

“Maybe you should do it anyways. At the very least, she’d stop pestering me about it.”

“The truth comes out.”

“No comment. Taking the bet or not?”

Was she serious? She looked that way. Glancing down the hall, I noticed Sean seemed to finally be making his move. Grinning, I turned my attention to Kaylee. “Deal,” I said, offering my hand. She shook it and turned back to the couple standing awkwardly against the wall. They were talking, and it was clear what was being discussed by their body language. Both looked awkward as hell, which was weird considering their relative popularity. Sarah was always shy, but Sean was incredibly outgoing. Seeing him getting tongue-tied was uncomfortable.

“Damn it,” she muttered, looking over at me. “You saw them talking, didn’t you?”

“Yep.”

“The deal doesn’t count.”

“Nuh-uh. We shook on it.” She pouted, crossing her arms. “What? It’s not like you weren’t going to give me one anyways.”

“I don’t like losing.”

“Suck it up,” I said with a widening grin. “Later, of course.”

“Come on,” she said, slapping my chest with the back of her hand. “Let’s go get the good news.”

“How do you know she said yes?”

Kaylee looked back at me like the answer was obvious. “I told her Sean was going to ask her out and she should be ready with an answer.”

“What! Why would you tell her that?” Kaylee didn’t answer as she walked towards the new couple. “Kaylee!” I called out as I chased after her.