“Is butt sex all you frat guys ever think about?” Cassie said with a laugh.
While I did belong to a fraternity, we weren’t a bunch of slobby mooks. We studied hard and were known around campus for our good manners. Cassie and I had been going out for three months, and I’d never once mentioned the idea of anal sex… until that night.
I think I actually blushed. “I just really like you. I want to know every inch of you.”
“Especially those inches that involve my ass, apparently.”
“Look, never mind!” I said hastily. “I’m sorry I brought it up.” We were in my room at the frat house.
She was sitting on my bed. “I didn’t say no, Kyle. But what you’re talking about is a delicate thing, and somebody who rushes it can ruin it. Understand?”
I nodded. It was that potential vulnerability that called to me. I wanted to pleasure Cassie at an expert level. Anal sex, I knew, was something special. I tried to explain all that to her, feeling I was failing miserably.
But she smiled her gorgeous smile. Cassie’s a taut, lovely 21-year-old with dark hair and enchanting eyes. She’s whip-smart and super-hot.
“That’s sweet, Kyle. And I want to do it with you. But I have one rule. I refuse to be anyone’s first anal experience.” Her eyes glittered. “So, tell me. Have you ever done it before?”
I started pacing anxiously back and forth. I imagined how awesome it would be to penetrate her so intimately, to feel the grasp of her tight back passage, to coax secret pleasures from her.
“Well?” she prodded.
I stammered, “I — I — I… uh, I have and I haven’t done it.”
She sighed. “That’s not an answer. I think I should go.”
She made to stand, and I realized I’d put our relationship in jeopardy. I had only one possible way out.
“Don’t leave! I’ll tell you the truth.” My heart pounded. “I have done anal before. But not with a woman. It was with another guy.”
I was bracing for all sorts of reactions, but Cassie surprised me by grinning widely.
“Cool! Tell me about it!” She grabbed my hand, pulling me down next to her on the bed.
So I spilled. I told her it had only happened once, on a night last year after me and one of my fraternity brothers had gotten drunk at a party — though I wouldn’t tell Cassie the guy’s name. We’d gone back to his room, laughing, and started daring each other to do stupid shit. First, it was do 30 push-ups or stand on your head, then somehow we were challenging each other to take off our clothes.