Sucker for the Boss

by Blue Sky Books

  “Dad…” Aron was the one who spoke up but Bob raised his hand to silence him. Tracey’s heart was racing, she was afraid it would beat out of her chest.

  “Finally!” he said and looked at her mom and they both broke into childish giggles.

  Bad Crush for My Dad's Best Friend

  It was my twenty-first birthday today, and I was more excited than usual, because my dad was going to take me on a trip to go skiing with a friend of his. He had done this in the past, but when I was younger, I wasn’t allowed to enjoy any of the drinks, and I’d be lying to you if I said that I wasn’t excited about having some of the custom mulled cider that they offered on the slopes of our favorite weekend getaway spot.

  We lived in Southern California, and there were a number of places to go skiing within an hour and a half drive from our place. I realized that it was a bit childish of me to look forward to something that so many adults take for granted, but I really couldn’t help myself. There was something so romantic about sitting in a mountain lodge — just a snow bunny with a warm cider. I imagined what it would feel like to get a bit tipsy, and find some rugged silvery fox to steal away a few moments of passion with in between ski runs. I knew the cider would help loosen me up, and I couldn’t wait to see just how close reality would get to my fantasies.

  When my dad told me that his business partner, Tom, would be there, I grew excited. Tom had been a long standing figure around the house, and I had been crushing on him ever since a couple of years ago, when I realized exactly how attractive an older man could be. Of course, I told my dad none of this, and did my best to play it cool.

  “Sounds great Dad, I’ll go and keep you company,” I told him, when he offered to take me with him on the trip.

  In the meanwhile, I was rummaging through my lingerie drawer, trying to figure out which pair of underwear would provide the most ‘compelling argument’ to a man like Tom. I knew that trying to bag an older guy, particularly a man like Tom was a bit of a conquest, but to be honest, I was up for a challenge. When a guy has been with more partners than I have, I always get the sense that there is something that I’m not quite caught up with, in terms of relationship maturity.

  I’ve never been with an older guy before, and I’m not exactly sure why I have such a crush on men like Tom. I think it is because I know that they will be able to bring me to new heights of sexual pleasure. A younger guy is eager, and let’s be frank with one another — more often than not, he ends up blowing his load before the big show. In this case, the big show is the female orgasm. Am I right?

  I mean, a dude can jack off in just about any way, but when it comes to heterosexual relationships, a man needs to know how to treat his woman well in order to come up with anything resembling a full female orgasm. I don’t have any problems getting off by myself. If left to my own devices, with the right fantasies, I can climax ten times in an evening, no problem. I’m usually really tired afterward, but I always feel like whatever sleep comes after riding a wave of ten orgasms is well deserved.

  A couple of knocks sounded off at my door while I was busy deciding between a black lace pair of panties, and a thong.

  “Stacy,” my dad’s’ voice came through the thick mahogany wood of the door, “We’re going to be leaving in about ten minutes— so make sure you’re ready, alright?”

  “No problem, Dad,” I replied, somewhat automatically.

  I decided to go with both the thong and the panties, so I could make the appropriate decisions based on how I felt that evening. After removing only two pairs of panties from my drawer, I heard another knock at my door, and I bit my lip. I was so shy about my sexuality, and it felt to me like if someone was knocking at my door while I was busy thinking about sex, they might somehow pick up on it — I don’t know, I guess I’m weird like that.

  “I’m changing!” I lied, and perhaps a bit too enthusiastically, “Who is it?”

  “Alright,” came the voice from the other end of the door. “It’s Dad.”

  There was a pause for a moment, and I was certain that he had been a bit put off by my outburst; my dad handled it well though — he always did. He was an understanding man, who did what he could for his daughter. I felt bad.

  “Tom’s here, and we were wondering if you needed any help getting some of your things out to the car,” he said.

  This was my dad’s way of suggesting that I hurry up. I didn’t hear anything else, really, except that Tom was here, and my dad was ready to go. I didn’t know that Tom would be meeting us here at the house, but it made sense, as he and my dad would probably want to discuss some business matters sooner than others. The two had been partners for years, and the primary thrust of this trip was a meeting to discuss some larger merger within their company. I didn’t know the details, because frankly, Dad’s business was not that interesting to me. Tom, however… well, you get the idea.

  “I’m almost ready,” I called out. “I’ll get my stuff, don’t worry about it.”

  I threw on some clothes.Stuffing a couple of ski clothes in my bag, and grabbing a journal, I felt like I was ready to get going. Besides, I kind of wanted to get a chance to say hello before we started up toward the mountain.

  I was still a bit reserved about Tom, and obviously I had mixed feelings. It was so strange to me that I felt so easily aroused when thinking about him, particularly because he was so old. The man was in his fifties, easily, and the idea of hooking up with my dad’s business partner was totally unrealistic, but also a little bit taboo. I’m not sure if it was the forbidden element that made it so enticing, or what exactly was going on, but my emotions were oscillating like crazy. First I wanted him, and then I stopped to think about it for a second, and it seemed like a really dangerous idea.

  “He probably just thinks I’m a silly girl,” I told myself, before walking out into the living room.

  Still a bit aroused from my private fantasies, and totally nervous, I shook Tom’s hand. He was just as gorgeous as I remembered. He wore a casual business jacket over a tight t-shirt. Beneath the shirt, I could see his chest muscles. The jacket also was filled out from his broad shoulders. He had his charming smile, like usual, and when I gave him a hug hello, he did not back away from my touch. Tom was a real man.

  When we hugged, he took a deep breath and smelled my hair. With tact, and grace, he refrained from holding me longer than would be obvious, but he didn’t hold his tongue.

  “Stacy,” he said, “you look great. Glad you’re coming along for the trip.”

  “Finally, get to drink some of that cider this year,” I said, telling him the first acceptable thing that came to my mind.

  My dad went into the other room for a minute to grab a few things.

  “I’ll be right back, why don’t you two take your things out to the car?” he said.

  “Sounds good dad,” I said, and I lifted up my bags.

  Tom offered to pick one up for me, and I consented, figuring that he was simply being a gentleman. When we made our way out the door though, something changed distinctly within Tom’s behavior. He began to stand really close to me, and lean in so that his face was close to mine.

  “Feels like you’re ready to go,” he said, smiling at me.

  He was so close to my face that I could feel the heat of his breath. He smelled warm, and a bit spicy, and I couldn’t help but feel a bit of desire rise up inside of me.

  “He’s so close to me,” I thought, not daring to speak. “He could reach his lips out right now, and we would be…”

  I didn’t have time to finish my thought, because he opened the trunk of the car and then set my bags in the back. I couldn’t tell if he had leaned in for dramatic effect, or if he was hitting on me. He felt so dangerous, and I was interested, but totally anxious about the whole thing. I thought about saying something to him, but I didn’t want to seem stupid, if I was actually making all of that up in my mind, and he was just being a nice guy.

  “I heard you’re quite the ski buff,” h
e said, leaning up on the car, and casting a cool glance over my body.

  His eyes moved along from the top of my body, down to my breasts, and finally to my hips. When he was done surveying me, like a piece of meat, I looked at him, wondering if he was being for real. He didn’t flinch. He didn’t back off one bit. He didn’t apologize, and he didn’t stop staring at me.

  “Your body looks great,” he said. “You’ve probably got a lot of endurance when it comes to athleticism.”

  I let out a sigh of relief.

  “Yea, I can hold my own,” I said. “I’m in shape because I spend a lot of time running during the off season. I actually hope to ski competitively one day.”

  “How are you with agility?” he asked, still looking at me. “Can you move around trees, and handle moving around small obstacles?”

  “Yea,” I replied easily. “It’s all about absorbing shock with your thighs, and really squatting down so you lower your center of balance.”

  I demonstrated for him, not really thinking about what I was doing, and he gave me a raised eyebrow after I showed him a particularly good squat.

  “I bet the guys really go crazy for you,” he said.

  “Why do you say that?” I blushed.

  He paused for a moment, as if to reflect on whether or not he would offer me a full disclosure.

  “I’m just sure that a guy would really like to go skiing with someone as skilled as yourself. Most young women don’t realize just how capable they are, and they tend to hide behind an artificial sense of insecurity,” he informed me. “Real women know what they are worth, and they tend to blow men away. Just the fact that you know how to move like that would make any skier go crazy.”

  As I was reflecting on Tom’s words, my dad came out from the house. He was carrying his own bags, and wearing a great smile on his face. I could tell that he was so excited to be going out with me on this trip, and I felt happy to be the daughter of a man who loved me so much.

  “So, I’m ready to go,” I said, smiling, and turning to my dad.

  “Alright,” he said, “Let’s get a move on.”

  Tom smiled at the two of us, gave me a wink, and then turned to go to his own car.

  “I’ll be expecting to catch some of those skills on the slopes,” he called out, bringing a smile to my own lips.

  “You two seem to be getting along,” my dad said, as he got into the car.

  “He just likes to show off,” I said, putting Tom down, so I could feel more comfortable about myself.

  .:.

  The trip up to the mountain was relaxing. I was in the car with my dad, and Tom went in his own car on the way up. We listened to some oldies music, and I stared out of the window. I enjoyed watching the way that the landscape changed from the desert chaparral in the valley, toward the pines of the higher elevations. Eventually, the snow began to be more of a prominent feature, and I was excited to get going. We still had a solid afternoon of skiing ahead of us, and for a while, I was actually more excited about skiing than I was that we would all be going together and that I might get another chance to catch a glimpse of Tom’s chest. He was a masculine guy, and was never too worried about dressing and undressing in front of my dad and I. There was never anything too blatantly sexual about his behavior — there was more of a consistent level of comfort with his own physical presence. The causal nature of his occasional nudity made things all the most exciting for me.

  “I’ve got some things to take care of when we first arrive, but maybe you and Tom can hit the slopes first,” my dad said, as we approached the cabin. “I know you’re excited to get going.”

  “Aww…” I said, knowing that my dad wanted to go skiing with me more than he was letting on. “Alright, but will we have a chance to go out together tomorrow?”

  “Absolutely,” he responded, reaching a comforting hand over to rest on my shoulder. “We’ll go all day, I promise.”

  The cabin was beautiful. We rented it out a couple of times a year, sharing the lease with another friend of my dad’s. The place felt like a second home to me, as I had been coming here with my dad ever since I was young. Tom had been a recent, if welcomed addition to these family / business get-aways, though of course, I didn’t mind at all; each time I saw him, I swear I fell more in love. At this point, I had hopes in the direction of being seen as a young woman, as opposed to just a kid, but there was a big part of me that felt like Tom would simply remain a crush forever.

  As we settled into the place, I pulled my skis out from the closet and started to suit up. Tom was already getting ready to go, and I intentionally barged in on him while he was changing so I might catch a glimpse of that body — it was every bit as amazing as I had remembered. He was just putting on a shirt when I entered the guest room. Though there were separate rooms, there weren’t exactly doors that would lock, or shut and stay shut. The entire cabin was designed to be a sort of cohesive unit.

  The two of us left soon after Tom got dressed. I kissed my dad goodbye, and he left Tom with a warning.

  “She’s a bit of a daredevil,” he said, looking at me approvingly. “I want you to take good care of her. I have to go to the other side of the mountain this evening to meet up with that client I told you about, and I will probably be back late.”

  “I’d worry more about whether or not she’ll be able to keep up with me,” Tom said with an air of confidence that brought a twinge of desire between my legs.

  “Oh, you bet I’ll be keeping up with you, old man,” I told him, squinting my eyes at him like a tease.

  He laughed and so did my dad. Today was off to a great start, and I couldn’t wait to hit the slopes.

  We started off on some intermediate runs, just getting used to the terrain, and the feeling of the snow. The weather forecast said that it would be snowing tonight, and there was still fresh powder on the ground from the night before. Usually, the conditions in a place like this mountain were a bit slushy, or even icy, if the weather was unpleasant. Knowing that pure powder was beneath my skis was a liberating experience, and I wanted to take full advantage of the scenario.

  Tom and I bullshitted about college, and his lack of a love life while we were on the lifts, and then took turns challenging one another to an increasingly challenging game of what was essentially tag. The two of us would take turns speeding past one another, each struggling for a gain in momentum — some tiny turn managed more efficiently than the other, which would propel us past the other. On our pass, we would tag the other person on the back and then fly past in a flurry of powder. After one particularly bold moment, I slapped him on the ass, making sure that my own ass was waving in the air after him as I sped down a black diamond run. I loved putting him in his place, but he never ceased to amaze me with his ability to get right back up with me, and return our game tit for tat — that was the first time Tom touched my ass, and I’d be lying if I told you that I didn’t slow down a bit, just hoping that he would seize the advantage. Tom didn’t let me down.

  Only when it began to get dark did we decide to turn in for the evening. We had a couple of runs with the night lights on, but it was mostly for the novelty of the experience. I couldn’t wait to get back into the lodge, and get some of that cider inside of me, and Tom didn’t seem to mind that my interests had shifted from athleticism to indulgence. We finished our final run for the evening in a leisurely descent down the intermediate path. I managed to narrow my focus enough to manage some tight navigation around a series of small hills designed for skiers who had a keen understanding of how to move their bodies while in descent. I felt like I had hit my prime for the evening, and didn’t miss a single mogul.

  All in all, the first day of skiing with Tom was incredible, initially I had been a bit nervous about spending time with him, but after a while, everything seemed to be so natural, that I began to worry less and less that he was older than me. There was something so reassuring about his presence, that I felt like my previous concerns about age were more of a soci
al taboo than anything else.

  When I thought about how we had touched each other on the ass during the skiing, I wondered how he had interpreted that exchange.

  “Probably it had meant nothing to him,” I thought to myself. “Just because it had been something that had caused a bit of arousal inside of me, doesn’t mean that Tom feels the same way.”

  I could still imagine the sting of his hand as it left an imprint on my ass. He had certainly hit me a bit harder than I had hit him. There was a definitive point of contact, and I almost lost balance when he slapped me in the ass. I was shocked, and a bit surprised. In spite of myself, I thought about how it would feel if his hand connected with my actual ass. The tension building inside of myself was incredible. I felt like I would almost do anything at this point just to make things less awkward inside of my own mind. I felt like I needed to open up communication with him about how I was feeling, but I was afraid.

  We made our way, steam rising from out of our mouths into the lodge, and Tom bought a bottle of the cider to celebrate an evening of hard work. After uncorking the bottle, we passed it back and forth between each other while trekking up the from the lodge to the cabin. All the while, we laughed and recounted some of the better moments of the day. There was an unmistakable difference in the way that we were interacting — an intimacy that hadn’t ever been present before. For the first time, I felt like maybe, just maybe, my crush might not be so one-sided. The feeling of potential reciprocality was a rush for me, which I embraced wholeheartedly.