Daddy's Best Friend (Once Upon a Daddy)

by Kelli Callahan

  “That’s—highly debatable.” I looked down at her ass, practically entranced with the sight of it. “It’s going to sting a little bit more than it did last time—these pajama pants aren’t as thick as your jeans.”

  “Especially if you punish me for what I did in high school…” She sighed and looked over her shoulder at me—it wasn’t just a playful stare; her eyes were burning with desire.

  Fuck—the line is already crossed, and I don’t think I can get back across it. She definitely can’t…

  “Is that what you want?” I narrowed my eyes at her.

  “Maybe just—one thing I did wrong.” She bit down on her lip and practically started to tremble.

  She wants it—but she’s struggling. I’ll try to gently ease her into it. She’ll figure out whether or not she likes it, and if she actually wants—discipline.

  “We can start with the cheating.” I looked down at her ass. “If I was going to punish you for pulling the fire extinguisher, I’d have to pull your pajama pants down—and you’d be here twice as long.”

  “That bad, huh?” She bit down on her lip again and pulled the edge of it into her teeth.

  “Definitely.” I nodded. “Not the worst thing you’ve done—but worthy of feeling the sting through nothing more than a thin pair of panties.”

  She didn’t have a negative reaction to that. I guess I can push a little further—we’re already so far past the line now that it doesn’t matter.

  “Okay…” She exhaled sharply.

  “Of course, if I was going to punish you for smoking…” I let my words trail off for a second.

  “You’d have to pull my panties down for that, wouldn’t you?” She trembled a little harder.

  Fuck, she got there on her own? She really does want this…

  “That’s right.” I nodded. “That spanking would hurt a lot worse. It would be one that you wouldn’t forget the next time your friend showed up and tried to be a bad influence.”

  “Okay, then I guess I’m just going to be spanked for cheating—this time.” She squirmed a little more.

  This time? She hasn’t even felt my hand and she’s already planning her next trip across my knee.

  It had been a long time since I had a woman across my knee begging to be punished. I had to remind myself that what was about to happen was very new for Chrissy, and there was a chance she had a fantasy that wouldn’t match reality. I was fine with that. The line wasn’t just crossed, it was totally gone. I had to give her a spanking and make sure it was a taste of actual discipline. If she didn’t want it, I would stop. There was no need for a safe-word. She didn’t know how to use one and real discipline wouldn’t have an escape option. It was better to just read her body language and hold back if it was too much for her to handle. I was pretty sure that the girl inside her that needed a Daddy was reaching out to me—and she did want to get a spanking that left her with a little redness when she looked in the mirror later.

  SMACK! SMACK! SMACK!

  “Ow!” She squirmed a little bit. “I definitely feel it a lot more through my pajama pants!”

  “I told you that you would.” I nodded and lifted my hand.

  SMACK! SMACK! SMACK!

  “Owww…” Her response was a little more drawn out and I heard a slight whimper.

  “Why don’t you tell me why you’re getting spanked?” I lifted my hand again.

  SMACK! SMACK! SMACK! SMACK! SMACK!

  “Ouch! Because—I cheated…” She whimpered a little louder.

  “Do good girls cheat on their tests?” I let my hand linger for a second and then pulled it back.

  SMACK! SMACK! SMACK! SMACK! SMACK!

  “No!” She kicked her feet and squirmed.

  “So what were you when you decided to cheat? Were you being a good girl?” I left my hand flat against her ass.

  “No…” She shook her head back and forth. “I was—being a bad girl.”

  “And what happens to bad girls?” I lifted my hand.

  “They—get spanked.” She exhaled sharply and grabbed onto my pants.

  SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK!

  “Oh god, I’m sorry! I won’t cheat again!” She squealed and bounced on my knee.

  “I’m glad to hear that.” I rubbed her ass a little bit. “But, you’ve already cheated—so you have to be punished for it.”

  “Y-yes, sir,” She whimpered but settled back across my knee once she stopped bouncing.

  She seems to be taking it well. I’ll try a few smacks that are a little harder at the end of this series…

  SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK!

  “Ah! I’m sorry!” She bounced a little more when she felt the last three, which were placed directly in the middle of her ass. “Please, I won’t do it again!”

  The barrier is coming down. She won’t be able to take much more—I don’t want to actually hurt her.

  SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK!

  “Oh god…” She buckled against my knee and I heard a faint sob in her throat.

  “I think that’s enough for now. If you cheat again, you’ll be across my knee a lot longer. Do you understand?” I put some firmness in my question.

  “Yes sir!” She nodded quickly. “It’ll never happen again!”

  “Good.” I patted her ass a couple of times. “Now, let’s talk about the other issue—you called me an old man.”

  “Oh wait, no! I didn’t mean it…” She shook her head back and forth.

  “You still did it and you’re still going to get punished for it.” I lifted my hand—they were going to pretty gentle compared to what she had already gotten, but they were still required.

  SMACK! SMACK! SMACK! SMACK! SMACK!

  “Okay—I won’t do it again…” She whimpered and kicked her feet.

  She’s sore enough for the gentle smacks to hurt a little bit…

  “We’ll see if you can bite your tongue next time.” I leaned forward and scooped her up in my arms.

  Chrissy had a hint of tears in the corner of her eyes, but the spanking wasn’t enough to make her cry. It was a good introduction and she would be able to process how it made her feel once she had time to settle down some. I wrapped my arms around her and pulled her close. She let her head rest on my shoulder and curled up in my lap. It felt really good to have her against me—but that wasn’t what it was about. I gave her a little taste and she would have to determine if it was something she wanted to experience again. She stayed in my arms for nearly thirty minutes before she finally leaned back from my shoulder. There were no more tears in her eyes, but her face was a little red.

  “Thank you…” She swallowed hard and stared directly into my eyes. “I—think I needed that.”

  “I think so too…” I nodded.

  Chrissy stared at me for a few seconds and then she leaned forward. I wasn’t even sure what she was doing at first—then I felt her lips land on mine. I was so caught off guard that I didn’t really return the kiss. I was just kind of shocked. It wasn’t that I didn’t have a desire to do it—I had certainly thought it, I just wasn’t prepared for it to happen when it did. She quickly realized it was one-sided and pulled back with a look of horror on her face. Her eyes bulged and she pulled away from my embrace.

  “I’m so sorry. I don’t know why I did that…” She ran towards the stairs before I could react.

  “Chrissy, wait…” I stood up and started walking after her. “It’s okay, we can talk about this.”

  “I don’t want to talk. I just—I’m sorry.” She to the top of the stairs and I heard her bedroom door slam shut.

  And—here come the complications.

  7

  Chrissy

  I literally wanted to curl up in a ball and die. I don’t know why I kissed Greyson. I was just—so overcome with emotions that I reacted to the moment. I thought something was developing, but I was clearly mis
reading the situation. I thought his playfulness and willingness to actually spank me was because he felt the same way I did—obviously I was wrong. The spanking didn’t make me cry, but the embarrassment certainly did. I grabbed my pillow, squeezed it against my chest, and started to bawl like I was a little girl that had just found out her crush thought she was ugly. Every emotion went through my head in an instant, colliding together and creating the perfect storm for a tsunami of tears.

  “Chrissy, please don’t hide in there. Let’s talk about this…” Greyson tapped on my door.

  “Please—please just leave alone. I can’t—I just can’t right now.” I buried my face in my pillow so that he wouldn’t hear the sob that followed my words.

  “Okay. If you want to talk, I’ll be downstairs…” He tapped my door a couple more times.

  I listened until I heard Greyson’s footsteps on the stairs before I pulled my face away from my pillow. I felt like a foolish child—a foolish child that fell for my father’s best friend because I believed that he could be my Daddy. It was a complicated disaster and I made it worse by kissing him. I did need the spanking. It was an emotional release and even though I could still feel the sting, I didn’t regret letting him put me over his knee—it was what came afterward that filled me with regret. I could have had something—something I truly needed—and I let desire cloud what I had until I was staring at the face of a man who clearly didn’t want to be kissed by me.

  How did I misread that?

  It was the first time I had ever initiated a kiss and would probably be the last. I understood some of my confusion. Being across Greyson’s knee wasn’t just purely about discipline. It made me wet—my panties were soaked. It was the hottest, most sexually charged moment of my life—but he wasn’t a willing participant in that fantasy. He was just giving me a spanking. He didn’t mean to lead me on—I had to accept that. He couldn’t help that he was hot-as-sin and looking at him made me think dirty thoughts.

  At the end of the day, I was just a child that he was looking after. The sooner I came to terms with that, the easier it would be. It also confirmed that I needed to start looking for a job as soon as I got my car privileges back—because I needed to move out of his house as soon as possible after making the environment as awkward as humanly possible. The tears stopped coming after a couple of hours, but I still felt sick to my stomach. I just lay in my bed and stared at the wall as time ticked by. The rest of the day was gone when I finally heard Greyson’s footsteps on the stairs again—and they made the sick feeling in my stomach twist into a knot.

  “Dinner is ready.” Greyson tapped on my door. “You need to eat something.”

  “I don’t want to eat. I’m not hungry.” I shook my head back and forth even though he couldn’t see me.

  “I’ll leave a plate in the microwave for you. You can go downstairs and eat after I go to bed if you get hungry…” He walked away from my door and I heard him walking back down the stairs.

  I guess he still intends to feed me. Hopefully he’s not rethinking his offer to let me stay here—I don’t want one kiss to send me all the way back to Chicago when I’m so close to realizing my dreams.

  I stared at the wall until I heard Greyson’s door close. I wasn’t really hungry, but I was aware of the need to eat something. I had a light lunch and I had worked all of that out of my system in tears. I walked downstairs and found the plate of food right where he said it would be. I microwaved it to at least get it warm again and then carried it to the table. In the middle of the table—was a folded piece of paper with my name on it. I was scared to read it. It could be anything from a letter expressing his disappointment to an eviction notice. I put down my plate of food and pulled my chair out. My curiosity wasn’t going to allow me to just leave the letter where it was. I had to read it. My hands trembled as I reached over and picked it up—but I fought against the shaking to open it.

  Dear Chrissy,

  Samuel Banks was my best friend in the whole world. I made him a promise. I promised him that I would always look after his family. I’ve told you the good parts of his life and I’ve sugar coated a lot of it. You deserve to know the man he was when he was great and not the one that lost the fight with his demons. That man—the great man—was the one who cried when he held you the day you were born. He was the one I swore an oath to.

  What happened today wasn’t your fault. All of the blame should be on my shoulders. I had a responsibility and I neglected it. You’re a beautiful girl and I get lost in those sky-blue eye sometimes—how they shimmer when you laugh. Sometimes it’s really hard for me to remind myself that you’re still Sam’s daughter, because you’re certainly not the little girl you were when I left Chicago. I let temptation get the better of me and that was a mistake. I confused you and I regret that. It’s—so complicated. I like you. I like you way more than I should.

  I don’t want things to be awkward between us, but we’ve crossed a line. Hell, I can’t even see it anymore, so we have to draw a new one. If you’re worried that I’m going to kick you out, it hasn’t even crossed my mind. I would do anything for your family and one awkward moment doesn’t change the promise I made. I hope that we find a way to move past it, but this house is big enough for us to never see each other if that makes it easier. Even if we don’t avoid each other entirely, we have to stay on opposite sides of the line. I’ll do my part to make sure that happens. I’m sorry it has come to this, but I think you’ll eventually see that it needs to be this way.

  -Greyson

  I was in tears when I finished Greyson’s letter, but I wiped them away so I could read it again. My eyes absorbed the words, but my brain was struggling to process everything. I wasn’t wrong. Greyson did like me—it wasn’t entirely one-sided. He was conflicted and I could understand that. I certainly had been—since the moment I moved in. His letter was meant to be the nail in the coffin of whatever we could have had. I didn’t have a choice or a say in the matter—I just had to accept it. I ate my food and walked back upstairs. I didn’t feel the need to cry. I was just kind of numb inside. All of the crying had left me emotionally spent, so when my head finally did hit the pillow, I was out.

  The next morning

  I didn’t sleep as long as normal, but it was a dark, dreamless slumber. I woke up before the sun was actually up. I rolled over on my side and saw Greyson’s letter next to my bed. I read it one more time before I climbed out of bed and stretched my muscles. My thoughts were in turmoil. I didn’t want to let go of what I had with Greyson. The kiss wasn’t a mistake—it was just resisted because he was conflicted. My thoughts started to surge. Was there any way to save what we had? Could I head him off before he finished drawing the line he talked about? I had to try. There was no guarantee that I would be successful, but I couldn’t give up without fighting to save it.

  I peeked out my door and confirmed that he was still in his room. The downstairs was dark, and he would have turned on a light if he was already up. When I wallowed in my misery the day before, I convinced myself that there was no hope for us because things were one-sided. I knew that wasn’t the case anymore. That gave me enough hope to walk down the stairs—grab a piece of paper—and sit down at the dining room table. I knew what I wanted to say, I just needed to find a way to put it into words.

  Dear Greyson,

  Thank you for your letter. It clarified things. You’re an honorable man who is trying to do the right thing, and I respect that. I just can’t sit back and watch you stomp out the flicker that has formed between us. I don’t want to just be someone who walks around the house when you’re not home, nor do I want to draw a line that keeps us apart. I want you to keep your promise, but sometimes promises are interpreted in a way that blinds us to the ambiguity.

  There’s something I need and you’re the only one who can give it to me. You know I grew up without a father, and yesterday was the first time it felt like I had a Daddy. I don’t think you would be dishonoring my father’s memory by taking
on a role he never had. I need—discipline. I need rules with consequences that make sure I follow them. I’ve lied to you, so I’m going to come clean. What you do with this confession is up to you. All I can do is write it out and put the letter where you can see it.

  Everyone believed I was a good kid, but that was a matter of perception. I was a good kid because I didn’t get caught most of the time. It was a label I didn’t deserve. My mother was disconnected after my father died and she didn’t really pay attention to what I did. The few times I got in trouble were because I seriously screwed up. My Box of Shame is that—things I’m ashamed of, but I never got the punishment I deserved for anything I did because I was a very good liar.

  The test I cheated on? I left those notes under my book intentionally. I planned to cheat. I would have gotten away with it too, if the teacher wasn’t so nosy. I cheated on several tests without getting caught, and my arrogance finally caught up with me. The fire alarm? I pulled it on purpose, and it wasn’t because I lost a bet. I actually won the bet, but Amanda chickened out. I almost got in real trouble for that one, but a few crocodile tears and pretend remorse made them go easy on me. After all—I rarely got in trouble. I was a good kid. The picture you saw of me smoking? Amanda didn’t steal the cigarettes from her father, and she wasn’t a bad influence. It was the other way around. I stole them from her father while I was staying over one weekend. I pressured her into trying it—and I took the picture. It wasn’t just once either.

  I told myself that I was going to be a different person when I got to California. I was going to work hard, do well in my classes, and earn everything on my own merits. I want to keep that promise, but I won’t be able to do it without guidance. I didn’t even manage to drive your Porsche once without breaking the rules. I won’t text and drive again, because I understand the risks, but if I’m left to my own devices—and you ignore me—who knows what kind of trouble I might get into?