Dinner with Toby

Kaylee’s deep breaths were a steady constant as she slept. Using her laptop, I’d signed into my school account and was using the time to catch up on work. I got a good half-hour in before there was a soft knock at the door. It sounded weird as I spun around to find Toby standing in the doorway, hand raised against the open door.

To the bedroom.

That we never closed.

Fuck me. I think I was about to drop dead from embarrassment. How much had he heard? Clearly that last bit, but how much before?

“Hey,” he said softly, glancing over at the sleeping Kaylee. Another reason why I was glad I had put that blanket over her. The last thing I needed was him seeing his nude daughter spread out over the bed. “I threw some things together if you are hungry…”

As mortifying as this was, I quietly left the room and followed him downstairs. He had two plates prepared with some sort of sub and chips. That there were only two indicated he knew Kaylee wouldn’t be joining us.

“Relax, Scott,” he said with a chuckle as I stared down at my plate. “Not the first time, and certainly not the last.”

Ugh. Kill me now.

“I remember the first time I stumbled on her with a guy. Lisa and I came back to find her taking the kids load right there on the kitchen table—and clearly not the first one of the night.” He chuckled. “Lisa was pissed. Kaylee hadn’t been sexually active long and had to suffer a miserable lecture from her mother on where appropriate places for that was. I think the lecture haunted her more than getting caught.” He sighed, a nostalgic look on his face. “I’m happy with the woman she’s grown up to be, but I sometimes miss that innocent little girl. If I walked in on her now, I don’t think she would even break stride.”

I honestly didn’t know what was worse. This conversation or him knowing everything I had been doing to his daughter upstairs.

Fortunately, the conversation quickly veered away from that aspect and went to more benign areas of her childhood. His stories gave me a glimpse of a Kaylee I barely remembered. The sweet little girl who had no interest in the wider world of sex and was more interested in learning to ride a ‘big kid’ bike that was far too big for her or chasing the neighbor girl with whatever bug she managed to find. I wondered if it was the same bike she tried to kill me with.

“What are your plans after graduation?”

I bought time by chewing on some chips. “Haven’t thought much about it.”

“College?”

I shook my head. “Four plus years of more school? No thanks.”

He laughed. “Trust me. The last thing you have to worry about in college is an education. One of the perks of being a guy. I graduated with a three-point six and my attendance record was showing up the first day of a class and the final. Way too many girls to play with than bother with class.” Saying nothing, I focused on my sub. “Not you though, is it?” My head shot up. He quickly held up his hands. “Whoa there. I’m not judging.”

Forcing myself to be calm, I took a few breaths. Between working out with Toby and the passing conversations I had whenever I was here visiting Kaylee, I had grown comfortable around him. I loved my dad, but there were things I knew I would never be comfortable discussing with him. That wasn’t our relationship and I was perfectly happy with the relationship I did have. Toby was different. He was far more involved in certain aspects of life than my father was--at this point at least. I still couldn't see my dad as a guy who hopped from girl to girl.

I stared at my sub as I spoke. “There are times I just feel like I don’t really fit in. My family is super conservative. Even though that’s changed a bit lately, it’s been that way most my life. All this sex stuff… It freaks me out a bit.”

He rubbed the back of his neck. “I don’t mean to make you uncomfortable. We’ve always been open about things—”

“And that’s great. I’m slowly getting comfortable with things.” I sighed. “I’m just worried Kaylee is going to go off to college and realize I’m holding her back.”

“She thinks the world of you.”

“I don’t doubt her feelings.” I took a deep breath, deciding that I was going all in. “It’s just that Kaylee was the first girl I’d ever been with. Since then, we’ve had a lot of problems mostly stemming from me not knowing what I want.” I looked up. He didn’t seem surprised by the revelation that Kaylee was my first. “You don’t seem too surprised by that.”

“Yeah, about that.” He looked embarrassed. “Lisa… ran a rather extensive investigation on you when you first started dating Kaylee.” He continued talking, but I didn’t hear anything as complete and utter panic shut down my body. I don’t think I ever experienced a full panic attack, but this came close.

“Scott? You okay?”

“F-fine.” I took a breath. “What did she find out?”

He laughed. “You should know better than anyone. Lisa was furious when she got it back, saying you had to be blackmailing Kaylee or something because you were, ‘The most boring boy on the planet.’” I chuckled nervously, feeling faint as the relief washed over me. “But during the process, she did discover that your unique partner count was zero. I think that worried her more than anything, but it was all unfounded.”

So that means she knew I was lying to her about my experience. Was that why she was telling me to sleep with older women who could ‘teach me?’

“I know how this is a massive invasion of your privacy, and I don’t necessarily want to defend her actions, but please try to understand her point of view. Kaylee means the world to both of us, and she is in the position to inherit a considerable amount of money and is related to someone with deep connections in both the business and political world. Lisa is worried people will only see her as a means to access wealth or have other intentions for her.”

“Not really happy about it, but I think I understand.” Especially since I've known Kaylee for years. I was a friend long before we started dating.

“Sorry.”

“Not your fault.”

“Still feel guilty about it. You’re a good kid and didn’t deserve that.”

“That aside, one of the reasons why I’m avoiding college is because I don’t want to hold her back.” He frowned. “She has been patient and understanding, but I know she has big expectations for college life and…”

“It’s not you.”

“No. No, it’s not.” I rubbed my neck as I stared down at my plate. “If I went to college with her, she would put all that aside for me. Maybe not all of it, but enough. Yeah, she’d nudge and push at me, but if I said no, she would respect that. I’m terrified that she would come to resent me. Maybe not right away, but there is no way that she sees all the stuff going around her and doesn’t think, ‘Ah, I could be doing that too…’ That is going to fester. If our relationship lasts, that resentment is never going to go away. How long until she starts looking back at her life and sees nothing but regrets and missed opportunities? I can’t do that to her.”

Crossing his arms, Toby had a grim look. “I’m not going to lie, Scott. College is not going to be easy. Kaylee grew up listening to all of Lisa’s wild stories and that has set expectations. Even compared to how crazy college can get, Lisa lived a wild life. Her sister was already a big name on campus, but Lisa quickly eclipsed even her and had a massive following of guys and was all too happy to use them. To show Renee up, the last semester of college, Lisa made a point of sleeping with at least one new guy every day.” He looked thoughtful as if remembering something he hadn’t thought about in a long time. “We probably still have the albums.”

“Albums?”

He chuckled. “That’s right. We didn’t have all the fancy tech you kids have. To prove that she did indeed sleep with a new guy every day, she took a picture of the guy and his cock to keep a record. Don’t think we threw any of them away, but there are several books full of pictures of all the guys she slept with.” My mouth hung open. Why? Why the hell would anyone do that? “And before you judge, she was hardly the only one to do that at the time. It was a popular thing.” He laughed at an old memory. “I couldn’t even begin to count the number of times I had to pose as some girl snapped her photos to tuck away in her album.” Grinning he leaned back in his chair. “But it was great advertisement. Girls would get together and show off their pictures and brag about, ‘the good ones.’ I chased a few girls in the beginning and before long, girls were seeking me out. Never had to chase after a girl again…unless I wanted to of course.”

“I can’t even keep up with Kaylee. Can’t imagine handling other girls on top of that.”

His expression grew serious. “Your relationship with Kaylee is more mature than anything I had in college. Yes, I dated Lisa, but that was more a relationship of convenience. We were friendly with each other, but it was mostly about sex. There were chunks of time where months went by before I even thought of her. Then we would bump into each other on campus, remember that, ‘hey, you’re actually quite good in bed,’ have a whole lot of sex for a week or so, then repeat.”

“And yet you ended up married to her.”

“Let me emphasize the, ‘good in bed’ part of that relationship. I don’t want you to get the impression we were only in it for the sex when we got engaged and later married, but the love you see now wasn’t there when we got married. Friendship and companionship, yes, but not love. I liked Lisa and wanted a family. She liked that I scratched that ‘itch’ that most guys couldn’t and felt that I would be a good father for her children. That was the basis of our relationship when we got married. Everything else we kinda lucked into.”

I thought of my parents. Luck played a role in their relationship too. It didn’t bode well.

I shifted nervously. “I don’t scratch that ‘itch’ for Kaylee.”

There was a moment of silence before he burst into laughter. “Sorry, sorry. It’s just you’re telling me that after I just listened to you two mess around for a half-hour.”

My face was red hot. “That was mostly Derrek…”

“I saw Derrek leave before I came in from the garage.”

“It’s not that. I mean…” Oh god, was I really going to come out and say it? “I…I made her tell me all about it. He might not have actually been there, but he was very much present.” I hung my head in shame. There it was, right out in the open. The anxiety was making me sick as I nudged the remaining chips from one side of my plate to the other. “When she was talking about him… I saw a side of Kaylee I never experienced before.”

Toby was silent for an uncomfortable amount of time. “Hmm. I think I understand now. But let me ask you this, was Derrek really important in that?” I looked up to find him with a kindly smile. “If you replaced him with any other guy, do you think she would have reacted the same way?”

“I… I guess so?”

“So you have to ask yourself if Derrek was actually important if he could be so easily replaced.” He grinned as he continued. “And flip it. If Derrek was the one in your position tonight, would he have gotten the same reaction out of Kaylee?”

“No.”

He gestured towards me as if I had discovered the answer that was in front of me all along. Of course, I did already know all this. Hearing him say it all, confirming that my initial gut feelings were right, helped cement it.

“Still… It’s weird.”

Toby snorted. “Sorry, I don’t mean to make light of this, but you’ve been having sex for what… three months? I remember when I first started, everything was weird.”

“I like hearing about and watching the girl I love have sex with other guys and you’re telling me that isn’t weird?”

“My best friend in high school was in a sexual relationship with his half-sister our senior year. It was one of those open secrets everyone knew but never talked about. They went public after he took her to prom.”

I was silent for a few seconds as I let that sink in. “Okay, that is weird.”

“My roommate in college always had his then-girlfriend wear a strap-on so they could do anal.”

Hearing that made me remember Kaylee and my first experience with anal. Special as the moment was, I wasn’t sure I was a fan. The thought of someone putting something in my ass—definitely not.

“Got plenty more, but I think you get the gist of what I’m trying to say. Everyone is weird, which means weird is normal. And I know it doesn’t seem this way, but it doesn’t matter what other people think about you. The most important thing is you and your partner. If you both enjoy it, who cares? Enjoy it.”

I let out a breath.

“It’s hard,” he said with an understanding nod. “You two are still young and are still figuring things out. Make sure you talk with her though. Talking about expectations, desires, boundaries, and things like that can be uncomfortable at the start, but it is important to a successful relationship. Lisa and I almost didn’t make it to this point because we never discussed our relationship and were living different versions of the same relationship.”

I nodded slowly. “Thanks, Toby. This was… awkward but helpful.”

“Happy to help. Just remember to talk with Kaylee about this.”

“I know.”

Helping him clean up, I went back upstairs to find Kaylee still asleep. She had shifted to her side, mouth open as she breathed heavily. I grinned, debating on taking a picture to tease her with later as she drooled onto the bed.

Why not?

Back at the desk, I opened the laptop and got back to work.