The Daddy Dilemma

by Tia Siren

  “You came to me last month, asking for a raise,” I said, before taking a sip of my drink. I maintained strong eye contact with her as I spoke, even if she worked to avoid it. “I’m assuming that nothing has changed?”

  “No. I mean, yes. I mean, I would still appreciate a raise. If that’s what you’re offering?”

  “It is. But I’m offering you more than a raise. I’m opening a new store in two weeks. I’d like you to manage it for me. And yes, it comes with a considerable increase in salary.”

  “You don’t want me to work at the flagship anymore?” she asked.

  “I don’t need you to work at the flagship anymore. You’ve done a good job there, getting things back in order. Debbie can take it from here. The store I’m opening is more... unique in its product. I think it would benefit from having someone like you handling things.”

  “Really?” she asked, her interest clearly piqued. She had begun to loosen up a little, settling into the atmosphere. As much as I liked her nervous, seeing her confident was just as sexy. Maybe even more so. Her breathing had steadied, and I struggled to keep my eyes from staring at her gorgeous breasts, slowly falling and rising beneath that tight dress.

  “So, you’re interested?” I asked.

  “Of course. I wasn’t kidding when I asked for that raise. My landlord has been a real dick lately and– Oh, sorry.” Her hand flew over her mouth.

  Her reaction was undeniably cute. Considering what I was going to ask her to do in a few minutes, cursing was the least of her worries.

  “Good to know that you’re interested,” I responded, smirking at her innocence. “But you might want to hear a little more about the new store before you dive in so eagerly. This isn’t like my other candy store. Like I said, this store will be selling a slightly different kind of product. To a different kind of customer than you’re used to.”

  “Oh, okay. What do you mean?”

  I didn’t respond right away, enjoying the confused look on her face. Then, I leaned back and signaled to the waiter nearest us. “Geoffrey,” I said as he approached. “Can you please fetch my suitcase? The one I brought with me.”

  Geoffrey scurried off, and I watched Kendra in silence. She was getting nervous again. Her eyes had trouble meeting my gaze, and her hands fidgeted with her champagne flute. God, I loved playing with her. It was a reversal of our old dynamics, back when we were dating. I used to be the scrawny, dorky one who answered her every beck and call. I would have done anything for her. There’s a part of me that still would.

  Geoffrey appeared by my side with a brown leather suitcase. “Here you are, sir.”

  “Thanks,” I replied, taking the suitcase while slipping a twenty-dollar bill in his hand. He scurried off, and I propped the suitcase up on the table, turning it to face Kendra. “The store that I’m opening up is called Luscious, and the candy that I’m going to sell is of a more adult variety.”

  I opened the case, and Kendra’s eyes widened delightfully at the sight of what was inside. Her cheeks flushed red, and her eyes looked in every direction but at the contents of the suitcase.

  “Are those... are those what I think they are?” She asked in a hushed whisper as if it were some sort of secret.

  “That depends. What do you think it is?” I smirked. There was no confusing what was inside the suitcase. I had only brought the one product with me tonight to show Kendra. It was a best seller at Jack’s nightclub, and I thought it would be perfect for what I had in mind.

  “It’s a dildo,” she said, her eyes flicking back to it. But she couldn’t seem to look at it for very long. “Is it chocolate?”

  I nodded. The case held a big, black dildo. The entire thing was made from chocolate, and it was specially designed to not melt at the same temperature as most chocolates did. That would defeat the purpose.

  “Right in one,” I said with glee, leaving the case open. “As I said, Luscious will specialize in adult themed candy of this nature. This is but one of the many products we have, and I’d like for you to be the face of the store.”

  “I don’t... I don’t know if I’m right for... I really don’t think that this is the kind of thing I’m suited to,” she said, her voice quaking.

  Goddamn, she was cute when she was nervous. “Kendra, you forget that I know more about you than the average boss. Quite a bit more. Believe me, I wouldn’t have asked if I didn’t think you were right for it.” She was staring at the dildo now, her cheeks still burning red. I could tell she was curious. “Try it.”

  “What?” she sputtered. “You can’t be serious?”

  “Not like that,” I assured her, knowing exactly where her mind had gone. “With your mouth. Try it.”

  “Here?” she asked, looking around the restaurant as if someone might overhear.

  “Right here.” I held her eyes as I said it, keeping my voice calm and commanding. I needed her to know that I wasn’t kidding. “If you want the new job, you’re going to have to show me that you know the product. That you’re willing to sell the product.”

  “I don’t know if I—”

  “I will match the raise that you asked me for. Plus throw in a healthy bonus.”

  I knew she needed the money. And more than that, I knew that she wanted to try it. She just needed a little convincing.

  Her eyes trained on the chocolate dildo. She slowly nodded her head and reached for it. Her hand wrapped around it, and she gave those plump lips a lick, puckering them up for the job they were about to perform.

  Even before she began, My dick hardened like a rocket. I couldn’t remember the last time I had been this turned on. She lifted the dildo from the case and held it in front of her for a moment. Her eyes scanned the restaurant to make sure no one was looking. Then she plunged it into her mouth.

  Her pink tongue ran around the head of the chocolate cock, as if she were tickling the hole. Then she opened her throat and swallowed as much of it as possible. Her thick lips ran up and down the candy shaft, covering the chocolate in saliva. She pulled it out, smacking her lips as she did.

  The whole time she kept her eyes trained on me. She made sure that I watched as she ran the thick dildo in and out of her mouth, licking the sides and swallowing the head.

  Despite myself, I was transported back to a time long ago. Back in high school, when the two of us were dating. I’d just gotten my license so I drove us out to the lake to celebrate. There, she gave me the most mind-numbing blowjob I had ever received. Like the dildo she currently worked, she treated my cock like a god, with total reverence. It would have been one of the better memories of our time together if it wasn’t for the fact that she dumped me the next week.

  My stomach sank as that memory hit me. I hated thinking about it. Hated it. Even now, it still hurt. Even now, it reminded me of how much I used to love her, and how much a part of me still did.

  “How was that?” she asked.

  I’d been so lost in my thoughts I didn’t notice she’d stopped sucking the chocolate dildo.

  “Well?” she asked.

  “Oh, right,” I said quickly, snapping myself from thoughts of the past. “Not bad, for now. Those are the lips I remember so I well.” I forced a smirk across my face. If the comment was hard for me to make, it was worth it for how uncomfortable it made her.

  “So? Does that mean I’m hired?” She still held the dildo in her hand, squeezing it as she spoke.

  “It does. But I need you to do something for me. Just so I know you’re going to take the job seriously.”

  “What?” she asked anxiously.

  “Take it home with you and use it.” She squirmed at the suggestion. That was my intent, of course, to put myself back in a position of power. “And let me know what you think. I need all the feedback I can get.”

  “Use it? You mean...”

  “I mean exactly what you are thinking.”

  The dinner didn’t last much longer after that. In fact, we skipped the food altogether. After her session with the
dildo, the atmosphere between the two of us became intense, at least I thought so. Her cheeks didn’t lose their color, and she was barely able to look at me. But if she was uncomfortable, I was a mess. Despite the way that I acted around her. Despite my arrogance and bravado, I knew then that I was still desperately in love with her. Maybe giving her the job at Luscious wasn’t such a good idea after all?

  Chapter 4

  Kendra

  It was probably one of the worst nights of sleep I’d ever had. It was one of those nights where I couldn’t actually remember sleeping at all. There had been a lot of tossing and turning, a lot of lying on my back, staring at the ceiling, but not a whole lot of actual sleeping. When the morning sun came creeping through my window, I knew I was in for a long, tiring day.

  The reason I’d been so restless was, of course, Grant Marcus. I just couldn’t stop thinking of the meeting we’d had.

  I’d been a nervous wreck before I even showed up at the restaurant. I had no idea what I was meeting him for. There was no telling with Grant. Our past relationship complicated things. I never knew if he was going to be professional or rub my nose in his success.

  From the very beginning, the dinner was off-putting. I had forgotten just how hot Grant was. Like, Jesus Christ, Lord have mercy, levels of hot. He was waiting at the restaurant when I arrived, and I had to work exceptionally hard not to trip and fall over myself as I made my way toward him. It was more difficult than it sounded since the very sight of him made my knees shake. The only way I could do that was to look anywhere but in his direction.

  He was so much better looking than he was in high school. Back then, he was a skinny, nerdy type. Admittedly, I had found that attractive, in its own way. It wasn’t like I dated him out of pity. I liked him, and we had a good time together. But now, he had a body that suggested hours had been spent in the gym sculpting it.

  Beyond that, his face had matured, too. His jaw had filled out. It was broader and stronger than it used to be, and he always sported a five o’clock shadow that made him look like a damn model. Combine that with his dark eyes, darker hair, and the expensive suits that he always seemed to wear, and the man was panty-melting hot.

  My undeniable attraction to him was probably the reason I was so susceptible to his demands last night. If anyone else had asked me to do that, I’d have told them to kiss my ass.

  The chocolate dildo lay on the bedside table, right by my head. Eyeing it, I couldn’t believe that I sucked it last night. Right in the middle of the restaurant, too, where anyone could have seen me. What was I thinking? It was all because of Grant. He was so damn cool and confident. I would have felt like a prude had I said no.

  But more than that, I wanted to please him. Ever since he hired me for his flagship store, I wanted nothing more than to please him. He’d changed so much since high school. If I knew how much he was going to change, I probably would have stayed with him. No, I definitely would have stayed with him.

  Too bad Grant has made it crystal clear that he doesn’t give a shit about me. It was so obvious last night that he took great pleasure in humiliating me. In making me follow his every command like some sort of sick puppy. Maybe I shouldn’t have said yes to the job. It was pretty obvious that he will be heavily involved with the new store, which meant I’d have to be around him more often. Was I just setting myself up for disaster?

  Not to mention the fact that the new store was adult-themed, which was a nice way of saying it was a sex shop. Why did he pick me? I couldn’t be the best choice for the job. He saw me last night, He must have noticed how much heavier I’d gotten. I’m not exactly a sex symbol these days. What chance did I have of selling sex toys? Candy, I can sell. But sex? I don’t think so.

  Sitting up, I reached for the dildo. When I got home last night, I considered giving it a go, but I couldn’t bring myself to do it, despite how horny I was. God, that moment in the restaurant. I wondered if he knew how wet I was when I sucked it? He looked almost bored when he watched me. He really had outgrown me.

  The dildo was big and thick. It was hard enough to get my lips around it. I wasn’t sure it would even fit when used for its intended purpose. I wondered again who the model for it was. As I sucked it, I couldn’t help but remember Grant’s cock. From memory, it was pretty big, much bigger than a skinny kid like that would usually have. Maybe he was the model for the dildo? I wouldn’t have been surprised. In fact, thinking that was what made me want to suck it in the first place.

  With the dildo in hand, I lay back in bed, very aware of what I was wearing. And what I wasn’t wearing. I had on an old, oversized t-shirt and nothing else. I never slept in shorts, and there was no point in wearing panties. It was too hot for that.

  Even the shirt was pointless. It was a relic from my ex-boyfriend, the one I left Grant for. He was a jock, with a great body and a face to die for. But he also had a small dick, much smaller than Grant’s ever was. When we used to fuck, I used to wonder what it would have been like to have Grant inside me. We were only in high school when we dated, so I never got to experience it.

  Just thinking of that, with the dildo in my hand, with Grant’s thick cock in my hand...

  I could feel myself getting wet as I thought about what it would be like if Grant was in the room with me. If it wasn’t a dildo I squeezed, but his throbbing cock.

  I ran my hand down to my thighs, feeling the heat emanating from me. I was hot and sticky and wet. All the while, my other hand squeezed down on the chocolate dildo. I moved it up to my mouth, licking the tip and pretending that it was Grant’s. It tasted so good, and I was sure that Grant would taste just as divine.

  My legs literally shook with anticipation. The dildo was bigger than anything I’d had before, but I didn’t care. The way I felt, then and there, I knew I could take it.

  I slowly moved it down my body, running the wet tip of the dildo over my thighs and around the swollen lips of my pussy. I teased myself, rubbing it against my engorged clit. Each time the dildo touched it, my legs jerked and my body shook. My breathing intensified, getting louder and louder.

  My free hand ran underneath my shirt and pinched my hard nipples, first one, then the other. I knew that Grant would love to have my big, heavy breasts in his mouth. I knew he’d love nothing more than to be inside of me.

  I could see his dark eyes burning into mine, and I could almost feel his strong hands exploring every inch of my body. His stubble would rasp against my skin when he kissed me. I would run my fingers over the hard lines of his masculine chest, and I would feel his heartbeat racing the way mine was now.

  He would start gently, teasing me slowly and sensually. But passion would overwhelm him. All those years that we’d been apart would have filled him with an unquenchable desire to claim me, the way he’d never been able to in high school. More than ten years of waiting had led up to this moment, and he wouldn’t be able to hold back.

  I imagined him mounting me. He’d spread my legs open roughly with his knees. His big, hard cock would press against my lips, and I’d urge him to penetrate me. And then he would.

  I slid the chocolate dildo deep inside my wet pussy. My lips opened up and swallowed it whole as they sucked around the outside. Deeper and deeper, I pushed it, wanting the entire thing inside of me. When it was as far in as it would go, I slowly slid it out, pressing it against my clit for a moment, before sliding it inside again.

  My breathing was deep and heavy. My knees shook uncontrollably. I let out a soft moan, running my free hand over my wet pussy and then sucking on my fingertips. All the while, I slid the dildo in and out. In and out.

  As I increased the speed, I felt myself getting close. In and out. In and out. Harder. Faster. I felt it start in my stomach, the fire, the burning. It built in me, spreading out to my legs and arms. Working its way through my entire body. I shook. All of me. I was going to come. I was going to explode. I ran my hand over my clit, pinching it. Rubbing it. Getting myself ready to explode.

  Jus
t then my phone rang.

  The sound shocked me. I sat up instantly and pulled the dildo from myself. Then, I reached for the phone. My body was a mess. I was like a jack in the box on the precipice of popping. I was going to ignore the call. I was going to finish myself off and then maybe call them back. But then I saw who the caller was.

  It was Grant Marcus. I had no choice but to answer.

  Chapter 5

  Grant

  “Hello?” Kendra said on the other end of the phone. She sounded rushed and out of breath.

  “Kendra, this isn’t a bad time, is it?” I asked, more out of habit than anything else. I actually hoped it was a bad time. Anything to catch her off guard.

  “Not at all,” she replied, still breathing heavily. I could hear her moving around frantically in the background, too. I wondered what she had been up to when I called.

  Unfortunately, I had a tough time concentrating. I was coming off a pretty rough sleep, and I was furious with myself about it. The night was not supposed to end that way. I was supposed to leave the restaurant feeling sure of myself, knowing I had played Kendra and that she was the one who would be feeling uncomfortable.

  But no. After she left the restaurant, I had to remain where I was for a while, until my erection went down. Even the simple act of watching her walk away, as her plump, round butt swayed back and forth, had me readjusting my pants.