A First

“You okay?”

“For the last time, I’m fine.”

“I’m not—”

“Oh my god. We haven’t even done anything yet!” she said with a laugh.

“I don’t want to hurt you.”

“You’re not going to hurt me.”

I let out a long breath. Kaylee was face-first on the bed, giving me a fantastic view of her ass. The ass my cock was currently resting on. I had lubed everything up… I think. Maybe I needed to use more…

“You okay back there?” she asked in a teasing voice.

“Fine.”

“Starting to think you got lost or something.” There was silence for a few seconds. “You didn’t lose your erection, did you?”

“Still there.”

“You know where the best place for one of those is?”

“Can you be serious for a moment?” I got a huff in response. “Isn’t this supposed to be a big moment or something?”

“It’s just anal sex. Plenty of people do it.”

“Yeah, but it’s your first—”

“Scott.”

“Yeah?”

“Just put it in. Gently,” she added quickly.

Right. Deep breaths.

The lighthearted atmosphere shifted when the tip of the condom pressed against her ass. As gently as I could, I gave it a little push. Her intake of breath froze me in place. “Okay?” I asked, nervously looking up towards her face.

“Mmhmm.”

A little more and I paused again. “Now?”

“How about I tell you when there’s a problem?”

I focused back on my task. Slowly, inch by inch, my cock disappeared inside her ass. I barely registered what I was feeling, my head spinning as my eyes nervously darted between her head and ass. After several agonizing seconds, it was done. Body pressing against hers, I anxiously, glanced up at the back of her head.

“Kaylee?”

“Not… what I was expecting.”

“You okay?”

“Fine,” she said with a puff of air as she tried to blow hair from her face.

“It… doesn’t hurt?”

She chuckled. “No, Scott. It doesn’t hurt.” I let out a relieved breath. “Though I’m super glad you don’t have a big cock or we might be having a different conversation.” It took a half-second for her words to register. “That totally wasn’t what I meant—”

“I get it.”

“Your cock is big—well not big—I mean it’s—”

“Kaylee.”

Groaning in embarrassment, she buried her face in my bedding. “God, this is every bit as embarrassing as my first time.”

Leaning forward, I planted a kiss on her shoulder blade. “Seeing you flustered like this… It’s cute.”

“Embarrassing…” She glanced back at me. “You can move you know.” Right before I went to comply, she continued. “Slowly.”

I felt a grin grow as I pulled away from her. “I thought you didn’t like slow n’ tender stuff.”

“I swear to god.”

Chuckling, I stopped myself before I pulled completely out of her ass and began pushing forward again. Her breath left her in a long sigh as I fully entered her once more. Once again, the mood was shifting as the lighthearted banter faded away. I repeated the process again. Then again. Over and over. Each time, I listened to her soft sighs.

I think I was too nervous to properly enjoy myself. Even with the slow pace, my heart was beating like I was in a full sprint. My body was angled awkwardly as I tried to avoid putting too much weight on her and the tension in my shoulders was killing me. I could already feel my muscles starting to cramp. Beyond the awkwardness, I hated this position for the same reason I avoided doggy-style as much as possible. I wanted to see Kaylee’s face. I wanted to look in her eyes when we were together. To see all the wonderful emotions and expressions play over her features.

A few minutes of this was all I needed to know I wasn’t going to cum. I was debating faking it when Kaylee’s voice interrupted my thoughts.

“I think that is enough for an intro.”

She practically read my mind. I don’t think I’d ever been happier to pull out of her. Moving away, I allowed her to roll onto her side. While she got comfortable, I took the time to toss the condom in the trash.

Heading back to the bed, I found her eyes locked on my erection. I was about to ask if she was okay but caught myself. I think I’d asked that a few times too many tonight.

“That wasn’t at all what I expected,” she said, leaning against me as I sat beside her.

“Bad?”

She shook her head. “Different.”

“So I suck at anal too.”

“Scott,” she groaned.

“Kidding.”

Her hand moved to my lap. My fading erection got a second wind as her fingers brushed against it. For a long while, neither of us said anything. I had a feeling the sex part of tonight was over, yet I didn’t feel disappointed. I don’t think things turned out how either of us expected, but tonight was always one I would remember. Kaylee and I had experienced something for the first time. Together. The outcome didn’t matter all that much. That memory would always be ours.

Feeling nice and fuzzy inside, I wrapped my arm around Kaylee and held her close. The silence didn’t bother me at all as I enjoyed her presence.

Eventually, we got under the covers with Kaylee instantly cuddling against me as I naturally wrapped my arm around her. Her breathing began to slow as she drifted towards sleep. I was close behind her when a loud cry jolted me awake.

Paige.

By her chuckles, I wasn’t the only one the noise had snapped back to consciousness. I groaned, resting my free arm over my eyes. “Don’t be too hard on her. Caleb knows what he’s doing and it is impossible to stay quiet once he gets going.”

Words that clearly came from experience.

I didn’t push on that, letting her words and their implications drift off. Kaylee didn’t seem to linger on them either, closing her eyes, she shifted slightly to a more comfortable position. No idea how she managed to fall asleep with all the racket next door, but she managed. No luck for me. Twenty-three minutes. I knew it was twenty-three minutes because I timed the damn thing on my phone. Not like I had anything else to do since sleep wasn’t happening and Kaylee was keeping me somewhat rooted in place.

But after that last wail of pleasure, silence finally won out. Guessing she had more than a few orgasms during that. A bit disturbing to know, but after some deep breaths, I let all those emotions go. I’d cut her some slack since it was her birthday too and she was on the rebound after breaking up with William. No idea how I’d missed that, though Paige and I didn’t interact much since I talked to William—not that we talked much before that point either. If Caleb was someone she needed right now… Good for her. Besides, this was one of those times where I doubted she was doing it on purpose.

I just wish she wasn’t so damn loud about it.