Road Trip with My Best Friend

"Dammit!" I mutter as I hang up the call with Andrew. I couldn't really blame Andrew for ditching me after hearing what was happening with his fiancé's family, but a part of me wanted to all the same. After all, this whole stupid road trip had been his idea in the first place. I had told him that now we had turned 30 and also had legitimate income, a long road trip just didn't sound that appealing anymore, but he felt like we just had to do it one last time before he got married... especially if our first stop was Vegas. Well, there is no way I can change my plans now with less than 24 hours before I leave to meet with our key business partners. But I am definitely not looking forward to nearly forty hours of driving over the next seven days, all by myself.

Eight years ago, Andrew and I met when we were in the same recruiting class of a successful Silicon Valley start-up. We both hated our jobs and the 12-14 hour days that were expected of us. It was soul-sucking work and a couple of months later we became roommates and found ourselves spending most nights bitching about the company and how bad we wanted to leave and start our own company where we would "do it right."

Fortunately, in less than two years the company sold and although our payouts weren't huge, it was exactly the excuse we needed to finally venture out on our own. We chose Denver - partly because it wasn't Silicon Valley and partly because we saw a Warren Miller movie at a friend's house once and decided that we needed to try skiing.

It turns out that Denver was the perfect city for us. It is laid back, but with a deep talent pool, and a lot of really cool people that think the way we do. Best of all, the technology company we started has grown fast enough that we were able to completely fund it ourselves without any outside investors. We call all the shots and those shots include things like impromptu closing of the office on big powder days so we can all go skiing. I'm sure we have sacrificed some growth and profits along the way, but it has been worth it, because six years later we have a successful company and exactly the lifestyle we always dreamed of.

Every year, in early January, we take a week and visit our key suppliers and distributors, most of whom we can meet with at CES in Las Vegas. We also visit Dallas immediately afterwards for in depth planning sessions with our largest and most important distributor. It's right in the middle of ski season so we always schedule it very tight without extra play days in Vegas so we can get back home as soon as possible. However, this is Andrew's last year as a single man, so he somehow talked me into packing all of our materials into my car and driving the route again like we did the first couple years, before it was obvious that the company was actually going to make it. But now that he's cancelled, I'm going to have to do it all by myself. The first leg alone (Denver to Las Vegas) is almost 11 hours! This is going to really suck.

---

As I walk into my new house, my thoughts are consumed by what I need to do to get ready for the trip. Originally Andrew and I had planned to divide and conquer so we could meet with everyone on just one day and then have our second day in Vegas almost entirely free to party one last time. Now I'm going to have to spend the rest of the night trying to rearrange all of our meetings until both days are full. Doing this trip all by myself, I'll be lucky to have time for lunch, let alone have any real down time for having fun. It's going to be exhausting.

Five hours later and I've almost got everything rearranged. It went better than I expected, actually. Time to get some rest before the big drive.

Unexpectedly, my door bell rings. I check my watch; it's 11:14pm. Who the hell is coming by my house after 11:00pm? How many people even know this address? Andrew and I finally stopped living together after nearly eight years as roommates so he could make room for his soon-to-be bride, and I can probably count on one hand the number of people who even have my new address. Hell, I still don't have it memorized myself.

I open the door cautiously and before it's barely cracked Jenny pushes past me and bounds into the entryway. "Yeah..., this is worse than I thought. Are you trying to live like a monk or something? I mean, it's a nice place, but bare walls and no furniture? Now I know why you still haven't invited me over."

"What do you mean, 'still'?, I've only been here three days!" I protest. "And what are you doing barging in here this late at night?" I pretend to be angry, but it's not a very good impression, since I know that if anyone can cheer me up, it's Jenny. In fact, just seeing her brightens my mood considerably.

"I've been texting you for hours! I was worried something might have happened to you. I know how depressed you must be after breaking up with Andrew!" She makes a pouty face and holds her arms akimbo.

Despite her serious expression, I can't help but laugh. Jenny is a year older than me and a total knock-out. She stands 5' 7" and is thin, but in a sexy, curvy way--more of an athletic build then supermodel skin-and-bones. Aside from Andrew, Jenny is my best friend and we hit if off ever since I first bumped into her. We met my very first week in Denver when I tried skiing for the first time and I, very literally, "bumped" into her. Well, crashed into her is probably a better description of the encounter. She wasn't too upset, and seemed mostly amused to watch me try for several minutes to awkwardly stand back up on my skis after plowing her down. After mercilessly making fun of me the entire time, she took pity on me and offered to give me some free lessons. With all her gear and goggles and whatnot on, I had no idea what she looked like until we headed to the lodge together for a late lunch. I felt like I was in a Victoria's Secret commercial the moment she pulled off her helmet and her beautiful wavy blonde hair spilled out. At the moment I didn't think anything could keep me from staring into her beautiful deep blue eyes, at least not until she took off her jacket and I noticed her other, considerable assets: specifically her large D-cup breasts. They were straining against her tight thermal top and her nipples were just visible pushing against the thin fabric. To my initial horror, she noticed that I was staring, and she looked slowly and deliberately down at her chest and then slowly back up to my eyes and then asked me with a sly grin if I saw anything I was interested in. I told her I was just "admiring the slopes." We both laughed and the ensuing conversation came quickly and easily. We ended up sitting in the lodge talking for almost three hours and have been pretty inseparable ever since.

"Shut up, I didn't break up with Andrew. He's getting married!"

"Whatever, I know you're gay for Andrew. You can't hide it from me. I mean what other rich, 30-something guy who owns a successful company has a roommate? You're just jealous that he's banging some chick instead of your ass!" The familiar banter was coming back.

As she talks I smile and glance down at my phone. "Holy shit, eleven unread messages? You must be really horny for me!" I say in mock surprise.

"I'm dripping wet, but unfortunately I don't have the equipment you're looking for!"

"Damn, I was hoping you brought your dildo this time," I reply. It's been this way between us for as long as we've known each other. However, despite the initial attraction (on my part), it's never even been close to going somewhere between us. Somehow, from that first time talking to her in the ski lodge we immediately became best friends. I'm not stupid, I know she's hot, but the very idea of anything more than what we have just seems weird. And in the occasional moments when it doesn't seem weird, our friendship is just too important to risk. Although neither one of us were dating when we met, we've both been through various relationships since. In fact, she even lost a boyfriend once because he just couldn't believe that Jenny and my relationship had never been more than platonic. He made the dumb decision to demand that Jenny choose between him and our friendship. Regardless of our relationship status, we hang out constantly and most of our friends have at some point or other wondered why we've never hooked up. They probably wonder about us because the closer we have become, the less restrained we are with sexual jokes and innuendos. It seems as though Jenny and I are the only ones that don't think there is a massive amount of pent up sexual tension between us.

"You should think positively, maybe you'll finally score with Andrew on this trip. It's your last chance, you know."

I explain to Jenny that Andrew can't go anymore and that I haven't read her messages because I've been so busy trying to rearrange all of our meetings in Vegas. As quick as a flash she moves from teasing mode to concerned-friend mode and asks what I'm going to do.

"What can I do?" I reply. "I can't just stand-up all of these people. They are the reason we are doing as well as we are. Not only that, but we have made a lot of investments over the last six months and it will have been a huge waste if we can't get support from our partners. I can't really be too pissed at Andrew. He knows what a big deal this is and if there was any way he could be there, then he would go."

"Maybe he knows you've got a big deal in your pants for him." Jenny just can't resist when she sees an opening.

"Shut up, Jenny. This is seriously stressing me out." I know she's just joking, but it's not really what I need right now.

"I'm sorry Nate, I feel terrible that you have to deal with all of this. I wish I could do something to help." Jenny stands opposite me and gives me a quick hug. She pulls back and I can see she is screwing up her lightly freckled face in the cute way she always does when she is thinking hard. "I know! I am coming with you! I might not be able to help with your meetings, but I can help drive so you can be fresh for them."

"Hmm, as nice as it sounds, I don't think the two of us 'cumming' at the same time is really going to help me much with this problem." I know it's a lame pun, but it was about all I could manage at the time.

"I'm serious Nate. Let me come help."

Day One

That wasn't the end of the argument, of course, but after Andrew dropped out, I wasn't about to put up a convincing fight to prevent my best friend from keeping me company on some pretty hellishly long drives. And so it was that I found myself knocking on Jenny's door a little after 8:00am the next morning for the drive to Las Vegas. Jenny lives with three other roommates because being a free spirit that wants to "experience life to the fullest" does not, as it turns out, pay very well. She lives a fun life, but has held dozens of various jobs at different times. Currently she is a substitute teacher and a private ski instructor, but this could change at any moment. After throwing her bags into the back seat of my Range Rover we pull out onto the road to start our eleven-hour trip to Las Vegas.

Jenny and I have been inseparable now for six years and except for the odd vacation or work trip, I don't think we've ever gone more than two or three days in a row without seeing each other, and certainly never more than 24 hours without a phone call or text. However, we have never been on an extended road trip together and we are about to spend seven full days together, a lot of which was going to see us cooped up in my car. As we merge on to I-70 I start to have second thoughts. I know a drive to Las Vegas isn't going to tax our friendship, but that is just the very beginning of the trip. In fact, it isn't even the longest stretch that we will have to drive. I have a nervous feeling that this much time together could change our friendship forever.

Despite all my worries, the trip starts out great. It is cold and snowy outside which makes the warm car feel extra cozy. The trip from Denver takes you through some beautiful mountains that Jenny and I have driven through many times on our way to and from local ski resorts. In the six years I've lived here I still haven't gotten over how gorgeous the Colorado mountains are in a snow storm. Jenny and I talk and laugh the entire way through the mountains, reliving various ski trips that we have taken in the area.

We make our first stop after almost five hours at Grand Junction. By now the snow has slowed and I am hoping we can make better time. We pull in to gas up and to stretch our legs. Being 6'2" means that even in a car as roomy as my Range Rover, it feels really nice to get out and exercise my limbs. I have always been very athletic and even played Division 1 football in college. Well, I say played, but in four years I saw the field for exactly 23 plays from scrimmage. Still, it looked good on my resume and was a good reason to stay fit. Aside from the two years in Silicon Valley when I gained about 45 pounds (the long hours timed with my retirement from collegiate athletics combined in an unfortunate way), I have always kept myself in shape. Even though I managed to drop almost all of my extra weight after I moved to Denver, I met Jenny at my pudgiest and most unflattering size so she still likes to make fun of me for being fat.

Jenny, on the other hand, has always looked amazing. For the long trip she threw on a pair of charcoal grey yoga pants and a white cotton cap sleeve t-shirt. In the back and forth of the conversation, it was easy to forget what she was wearing, but once or twice during the trip she had to lean over to grab something and each time I got a mesmerizing view of her incredible cleavage and the tops of her breasts as they hung down heavily in her bra. Each time I quickly looked away as I started to feel a stirring in my crotch that was not going to be helpful.

I get out of the car and start filling up the tank, but I can't help being transfixed by the swaying of Jenny's hips and the movement of her tight ass in her yoga pants as she walks away from me towards the entrance to the service station. It's been almost two months since I last got laid and each time I go through a dry spell I find my body reacting to Jenny. It's probably part of the reason I've had a girlfriend most of the time I've lived in Denver.

I meet her in the station so I can pee and grab some snacks and then we head back to my car. Over the years I have gotten used to people checking Jenny out, but as we walk back to the car, every guy we pass seems more enthusiastic then usual. One husband in a minivan even gets smacked by his wife as we walk by.

"Did you see that? That was hilarious," she says with a chuckle. "I wonder what he did to get in so much trouble."

"Probably just checking out that incredible ass of yours in those yoga pants." As I say this I lean back in an exaggerated way to check her out. I look down at her and we shared a laugh. Then I see what is causing all the fuss. "Um, by the way, you are really nipped out," I say in what I hope is a casual tone. Jenny is not wearing a jacket and the cold is obviously getting to her as her nipples are clearly hard and visible through her white shirt.

"Oh, jeez, you're right," she says, looking down. I feel a familiar stirring in my loins. If the last five hours are any indication, I am going to be jacking off a lot this week.

---

It's after 6:00pm when we finally pull into the Bellagio valet line and head to the front desk while porters take our bags to the room. We are greeted warmly by the attractive young woman behind the front desk. "Welcome to the Bellagio, Mr. Mayfield. We have you staying for three nights in our Penthouse Suite."

"Oh shit!" I exclaim.

"What's the matter?" asks a very concerned Jenny.

"I totally forgot about the room. When Andrew canceled I had my assistant cancel all of the extra rooms that we booked for the entire trip. Usually we get an extra room so we don't have to share a bed, because the suites only have a king-sized bed!" I feel like a real moron. I can't believe I hadn't thought of that until just now. "Do you have any other rooms available?" I ask the the woman behind the desk.

"I'm sorry but we are completely booked. It's CES, you know. If you need an additional room, our concierge can help you find one, but it will most likely be far off the strip."

I wasn't sure what Jenny was thinking until I glance over and notice her grinning widely. I can tell I am going to be in for a lot of good natured ribbing once we figure this all out.

"Okay, okay. Let's talk to the concierge. Maybe we can find something that's not too far away." As I start to turn away from the front desk, Jenny catches me by the arm.

"Nate, this is silly. Let's just take the room. It's a penthouse suite, there's going to be plenty of space and I am tired after the drive." I sigh in relief, but then hear Jenny say, "besides, I don't want to ruin this elaborate scheme you've concocted to get into my pants." I go beet red and the woman behind the front desk feigns a coughing fit to unsuccessfully mask her laughter.

I have a meeting scheduled the same night we arrive, so I leave her to get acquainted with the room while I run off to a series of meetings, dinner, and cocktail parties that had been prearranged before I left. I tell Jenny that I would probably be back late and I will see her in the morning.

Day Two

It is almost 1:00am when I finally make it back to the suite. I'm not drunk yet but I'm starting to feel a little tipsy. I stumble back into the dark room forgetting all about Jenny until I open the door to the bedroom. She is sprawled out asleep on the bed and I am about to sneak back out when my eyes adjust to the darkness. Jenny is lying on her side with the blankets open to her waist. She is wearing a thin, loose fitting t-shirt and the wide scoop neck of her shirt has fallen open so I can see right down her shirt. She isn't wearing a bra and most of her bare breasts are visible including her entire right breast down to the top of her nipple. A combination of the alcohol and the sight of her beautiful tits makes me hard right away. It has been an unusually long dry spell and all I can think about is sliding my hard cock down the tempting opening between her breasts. I stand there for a few moments until I realize two things. First, I am touching myself, and second, somehow I have turned into a creepy guy who stands over a sleeping girl while he touches himself! That is enough to chase me out of the bedroom, but not enough to stop thinking about how that nipple would feel on my tongue.

I stumble over to the couch at which point I remember another thing... oh, shit, I didn't bring any pajamas! Come to think of it, I'm not sure I even own any pajamas. I generally just sleep in my boxers. "Oh well, I'll figure it out tomorrow," I think as I drop off to sleep on the couch fully-clothed. I sleep like a rock all night while dreaming of Jenny riding on top of my hard cock, her heavy tits slapping against my face with each thrust.

"Nate, get up! Time to get moving! It's almost eight o'clock!" I wake to Jenny poking me in the chest while she shouts encouragements at me. I may have slept deeply, but a couch is not the most comfortable place to sleep and I wake up with a sore back and a kink in my neck.

"Wow, this place is amazing! I knew you were rich, but I had no idea!"

"I'm not rich. This place is paid for by the company."

"Yeah, the company you own." Well, she had me there, I guess. "You go and enjoy your meetings, I am going to hang out here all day and just enjoy this room. Did you see the size of that jetted tub? This place is amazing! I want to come with you every year!"

Oh, boy. I just remembered something else I forgot to tell her about, and this one is a lot bigger than forgetting to book a second room. "Um, you're not going to be able to stay in the room today."