Road Trip with My Best Friend

"What are you talking about?" she asks in a suspicious tone.

"Well, the room is for entertaining clients, vendors, distributors, and other business partners. We get a huge suite so we can do our product demonstrations and meet in a nice environment. It's, um, what everyone does at CES." I am pretty sure springing this on her an hour and a half before my first meeting is not going to go well.

"Wait a minute, you are /saying/..." She enunciates the word 'saying' in a way that makes it clear I am being a total dick. "...that I can't be in this room at all today? That I have to just wander around the streets of Las Vegas. How long exactly do I need to be out of the room?"

"Um, well, just until, I don't know, maybe, around five o'clock."

"WHAT THE HELL AM I GOING TO DO FOR SEVEN HOURS BY MYSELF?! I SPEND ALMOST TWELVE HOURS IN THE CAR WITH YOU BECAUSE I FEEL SORRY FOR YOU AND NOW YOU ARE KICKING ME OUT OF THE HOTEL ROOM, YOU ASSHOLE?!" Yeah, this was going very badly.

"No, no, I was going to set up some really fun and cool things for you to do while I am in my meetings." I am totally improvising, and from the look on her face, I don't think she's buying it. "Let me just, um, go talk to the, um, concierge, and uh, make sure everything is, you know, set up."

I can practically feel the daggers from her eyes boring into my back as I bolt for the relative sanctuary of the lobby. I'm still wearing my clothes from last night and I've got to figure this out quick. I talk to the concierge and explain the situation.

"I don't care what it is, but I want her to have a good time. Shows, spa treatments, whatever. Just make sure she has a good time." He assures me that he will plan an amazing day and that any charges will be billed to our room. I tell him to thrown in $1,000 in chips for her to play the casino with.

When I get back to the room I tell her that I confirmed everything with the concierge and that he will be contacting her shortly to go through the day's activities. I gather from her body language that she is not expecting much and that we are not on speaking terms right now.

---

When I finally come back from dinner at 7:30pm, the suite is dark and abandoned, so I sit on the couch and turn on the TV. I'm not really paying attention though, because my mind is consumed with rehearsing my apology. Around 8:30 I hear the door knob turn and I brace for impact.

Jenny comes bursting into the room with a satisfied smile on her face. When she notices me, she comes bounding over and plops down next to me. Before I can get out my apology she sighs deeply and says with a smile, "I had the best day! I saw two different Cirque du Soleil shows--I didn't even know there was more than one! Then I had the most amazing spa treatment ever, and I learned how to play blackjack and craps! I felt like James Bond out there, it was so cool!"

"Look Jenny, I'm really sorry about today. First I forgot about booking another room, then I forgot to tell you about needing the suite all day, I should have..." Before I can get another word in, Jenny cuts me off.

"Hey don't worry about it. I actually had a... wait a minute, aren't you supposed to be in a meeting? What are you doing back so early?"

"I felt really bad and cancelled my late meeting." I see the worried look on her face so I hurriedly add, "it's fine, I saw him last night at a cocktail party."

And just like that we are back to our old selves. We order desert and eat while we take turns talking about our day. I look at my watch and announce that I should probably get to sleep so I can be rested for the morning.

She looks at me and says, "yeah, I wanted to ask you about that. Why did you sleep on the couch last night? Was that even comfortable?"

"It was okay," I lie. "I figured you were nice enough to come on this trip with me; the least I could do is give you the bed."

"You idiot, just sleep in the bed. We came out here for your meetings. You need to be rested"

"No, you can have the bed" I protest weakly. My neck is still a little sore from last night so I badly want to sleep in the bed. However, I still feel guilty about kicking her out of the room today and I don't really want to kick her out of the bed too.

"It's a king-size bed, we'll just both sleep in it... or are you worried that you can't keep your hands off of me?"

The image of her breasts and nipple as I looked down her shirt last night involuntarily flashes before my eyes. "I'm not sure that having my hands on that fine body of yours is something I'm /worried/ about," I reply with a laugh.

"Okay, then its settled. Let's get ready for bed."

"Oh crap, I just remembered the other reason I was going to sleep on the couch. I don't actually own pajamas. I usually just sleep in my boxer shorts. I'll go pick up some pajamas tomorrow."

"Don't be such a prude. We've been best friends for what? Six years now? Just sleep in your damn boxers."

While getting ready for bed I keep telling myself, "It's just Jenny, no big deal," but I can't help but feel a little excited, even though I know it's just the pent up frustration from going without sex for so long. I finish getting ready first and am sitting on the edge of the bed looking at my phone when she emerges from the bathroom wearing the same thin white t-shirt from last night with the plunging neckline, but instead of pajama bottoms, she is wearing a pair of extremely sexy light-grey boy-cut panties!

She follows my eyes and clearly sees my expression because before I can say anything else she exclaims, "I figured if you were just going to wear boxer shorts, then I would just wear panties. You know, that way maybe you won't feel so self-conscious."

There is a definite stirring in my crotch as my cock goes almost immediately to half-mast. "You're right, it's going to be hard to remember to be self-conscious when I'm staring at that hot ass all night."

She turns purposefully and partially bends over while running her hand over her ass. "You mean this ass?" she says seductively. Her legs are spread slightly so I can see the outline of her pussy lips between her legs. I am now rock hard. Best friend or no, my cock desperately wants to feel her wet pussy lips sliding up and down the length of my shaft. Then, turning, she says, "no, wait, I remember, you're a boob guy. Would you rather..., what was it you said when we first met?..., oh, yes, 'admire the slopes'?" As she says this she crawls seductively onto the end of the bed so that her shirt hangs wide open. I can see her large tits as they swing slowly from the movement of crawling onto the bed.

"You do realize this huge hard-on you're giving me is going to make it difficult to spoon?" I was accustomed to exchanging sexual comments with Jenny, but this felt different--like we had crossed a line--like we weren't joking anymore, but rather telling the truth and pretending it was a joke.

As soon as I say this, she looks down at my crotch and sees the obvious hard-on that is tenting the front of my boxer shorts. Her eyes briefly flash a look I haven't seen Jenny make before. She laughs and then turns away from me, pretending to arrange her pillow, but again displaying her ass. As she looks back at me over her shoulder she wiggles her ass back and forth and says, "hmmm, I do seem to be having an effect on you... I don't know that spooning will be any more difficult with that giant cock of yours, but it might be a lot more fun." We are definitely in uncharted territory now.

"Jenny, you're forgetting that the two of us have been best friends for years, but you've never actually met my cock. He's got a mind all his own." Looking at Jenny's pussy lips pushing against the soft fabric of her panties, I notice a small dark spot emerging. I thought my cock was as hard as it could be a few minutes ago, but somehow it gets even harder as I watch her pussy wet through her panties. I can't figure out if I should deescalate this before I make a move that might end our friendship or if I should succumb to the moment. The air somehow feels thicker. I need to make a decision quick because all the blood in my body is rushing out of my head and straight to my cock.

She rolls over so she is lying on her side facing me. Jenny lazily runs her hand down the deep valley between her breasts. Her nipples are hard and straining against the thin fabric. "Are you saying that your cock wants to meet me...?"

"Very much, but I can't guarantee how he'll behave. He gets really..., impulsive..., when he meets new people." My cock is so hard that the waist band of my boxers is pulling ever so slightly away from my abs. I glance quickly away from her heaving chest to look at her eyes and I see that she is openly staring at my erect penis which is trying desperately to push through my boxers. I see her eyes momentarily go wide when the button on my boxers finally gives out and the fly pops open. My cock is still in my shorts, but I can tell by the way she bites on her lower lip that she can probably see at least the side of my shaft through the gaping hole in my fly.

Just then my phone rings. It jolts me out of my stupor. I look at the number. It's my mom! Can you believe it? I obviously don't pick it up, but the moment is broken anyway.

"Wow, that got kind of hot and heavy," she says.

"Yeah, that was, um, fun." It sounds dumb coming out of my mouth and we both laugh. We get under the covers and lie down facing each other. Neither of us can think of anything else to say so we just look at each other until our eyes become heavy and we fall asleep.

Day Three

The hotel clock displays 7:24am when I awake feeling rested and fully energized. I glance over at Jenny who is sleeping deeply on the other side of the bed. Instantly the events of last night come rushing back and the memory alone is enough to give me another huge hard-on. I sneak off to shower and take care of my "problem." I can't decide if anything has changed between us or if our playful jokes just got a little out of control last night, but it's clear that I need to get laid as soon as possible. Unfortunately, I'm not sure how that's going to happen while Jenny and I are sharing a room.

Jenny is still lightly snoring when I finish getting ready for the day. I have some time before my meetings start, so I sneak down and confirm that the concierge can take care of Jenny for one more day.

It's January, so the sun is just starting to come up when I get back to the room. Jenny seems to be stirring so I walk over and gently wake her up. "Hey Jenny, you've only got about an hour before I'm going to need the room. I talked to the concierge and he's already got another great day planned for you." I really want to talk with her about last night, but I don't know what to say. There's also a part of me that worries I'm reading way too much into this. For all I know, she just saw last night as nothing but our normal banter, and everything else is just inside my under-sexed head.

She sits up and smiles. Her hair is a complete mess which just makes her look even cuter. "Did you sleep better last night?" she asks.

"Yeah, I slept great!"

"See I told you the bed would be better than the couch." She stretches her arms wide while yawning which pushes her breasts out against the thin fabric of her sleep shirt. I am starting to worry again about this road trip. Except this time I'm less worried about getting on each other's nerves and more worried about my hormones pushing me to make a move that ruins our friendship. I should never have broken up with my girlfriend two months ago. At least I wouldn't be so horny right now. "Well, I better get ready," she says as she stands up and walks for the bathroom. I know I need to get control of myself, but my feet are nailed to the ground as I watch her ass move in those sexy panties.

"I'm going to head out to a breakfast appointment. I'll give you a call later this afternoon and check-in on how you're doing," I call out to her after she steps into the bathroom.

"Sounds great. Good luck with your meetings!" she yells as I hear the shower turn on.

It's a good thing that most of my meetings are really just about shaking hands and maintaining relationships because I am distracted all morning. I keep replaying the events of the prior night over and over again in my head. By the time I've finished lunch I've managed to convince myself that I am making way too big a deal out of last night. I tell myself that I'm just a little extra horny and need to make sure to relieve myself more often to take some of the edge off. After all, this isn't the first time I've gotten a little turned on around Jenny after breaking up with a girlfriend. This will all blow over, just like it has in the past. My friendship with Jenny is way too important to let an overactive libido ruin it.

At 2:00pm I give Jenny a quick call. She tells me that she is having the time of her life. "Best vacation ever!" she says brightly.

"Do you think you might be able to spare some time to go pick up a ball gown?" I ask.

"Oooh, that sounds fun. What's up?" I explain that one of our partners puts on a black tie event each year at one of the swankiest spots in town and if she can get a dress, then she could come with me. "So you're asking me on a date?" she asks.

"You wish," I reply. "Just go by Neiman Marcus or wherever and find something nice. My treat. I'll be back by the hotel to get changed around 7:00. See you then."

---

When I get back to my empty hotel room, I pull out my tux. Last year Andrew and I finally decided to stop renting crappy tuxedos and had new bespoke tuxes made at a Savile Row tailor. It was a stupid extravagance, and I'm still embarrassed at how much we spent, but I can't deny that they look great. This is my first time wearing it and I feel like a million bucks.

I've just barely finished adjusting my tie when I hear the door open. I turn around and immediately stop thinking about how I look in my Savile Row suit. Jenny is wearing a beautiful off-white ball gown with gold embroidered flowers. It has a full train in back, but is slightly higher in the front to expose her ankles and freshly pedicured feet in four-inch gold pumps with delicate ankle straps. The dress is sleeveless with a deep V in the front and back. The bottom of the V extends down almost below her breasts, exposing the ample cleavage of her unsupported breasts. Her wavy blonde hair is done in an updo and her face is made up with just a touch of sparkles on her freckled cheeks.

I am stunned. "You look amazing!" I stammer. I can barely get the words out coherently.

She doesn't immediately respond so I look at her eyes and she is also frozen in place staring at me. Again I see that unfamiliar look in her eyes from last night that I had never seen before. "Wow!" She whispers. "That suit looks great on you. You really clean up nice."

"Forget about me. You look incredible!" I say.

She smiles and twirls around displaying the full effect of the dress for me. "Sorry I'm a little late. I figured I would get my hair and makeup done." Her face turns serious for a moment. "Um..., by the way, this dress and these shoes are, like, crazy expensive. I don't know what I was thinking. Don't freak out when you see the bill. I promise I'll pay you back, but it might take a couple months."

"Looking at you all night in that dress is all the payback I'm going to need."

"Hmm, are you sure I need to be wearing the dress to pay you back?" she jokes with a mischievous grin.

---

When we arrive at the party, the doors open up to reveal a luxuriously decorated ballroom filled with men in tuxedos and women in expensive looking gowns and jewelry. As we enter, Jenny hugs my arm as she leans in close and whispers, "this is so much fun! Thanks for this."

In her four-inch heals Jenny is nearly as tall as me. I smile as I turn and give her a light peck on the cheek and whisper back, "and thank you for wrapping your tits around my arm."

She looks down and notices that when she hugged my arm that she had pulled my arm right in between her bare breasts. I'm a little surprised to note that instead of loosening her grip on my arm, she presses her chest more firmly into my arm. "Oh great, my best friend is a pervert!"

"Yeah, I'm not sure we can be friends if you're going to keep wearing dresses like this," I say.

She rests her head against my arm and softly says, "then maybe, just for tonight, we don't have to be friends." As she says this she gently runs her fingers down my arm until her hand interlocks with mine.

I don't know how to respond so I turn my head and kiss her forehead as she leans into me and squeezes my hand. I feel tingles as bolts of electricity spread throughout my body from where our hands are touching. "Geez, what am I, thirteen years old? We're just holding hands!" I think, as my head fogs up.

The rest of the evening doesn't feel like I'm hanging out with a friend anymore. We never progress beyond holding hands or the occasional kiss on the cheek. When we dance on the floor she comes in close and rests her head on my chest. Still, our interactions feel more intimate than anything that happened last night. More than anything, I am surprised at how comfortable it feels to be with her like this.

Day Four

It's past midnight when we get back to the suite. I turn around after closing the door to find Jenny waiting in the center of the living room. I slowly walk over to her. Typically the two of us can't shut up when we are together, but now that we are back in the suite, we are unusually quiet. We come together and she puts her arms around my neck. She leans into my ear and whispers, "This was a perfect night." She takes a deep breath and then continues in my ear, "I don't ever get to do things like this, and it's all a little overwhelming." Her mouth is no more than an inch from my ear and I can feel her warm breath against my neck. "Thank you," she says and kisses me softly on the neck. I turn towards her and our lips come together for the first time. Our mouths are open slightly and I lightly suck on her bottom lip for a moment as we pull away from the kiss.

"I like you at this height," I say, and then lean in for another kiss. This time the kiss is longer and more urgent. She presses her lips violently into mine and I put my right arm around her waist and pull her tight to me as my other arm rests softly on the side of her ribs. We are both breathing heavy when we break the kiss but our lips are still only a few inches apart as I say, "We probably shouldn't be doing this. It's after midnight, we're supposed to be just friends again, right?"

She smiles and says, "maybe it shouldn't count as tomorrow until we wake up."

"Then it's okay if I do this?" I lean in and kiss her again.

"Just for tonight" she says as she kisses me back softly.

"Then I'm not sure I ever want to wake up again." Another kiss. This time I feel her tongue as she briefly sucks on my lip as we part. As she pulls away I grab her and pull her right back into me. Our lips open as we kiss hungrily. I feel her tongue enter my mouth and I pull her tighter against me as our tongues caress. Her arms are around my neck and I feel her fingers running through my hair as we make out.

"This is nice," she breathily whispers into my lips. Another kiss. "But, I need to shower all this make up off." We kiss deeply and I briefly suck on her tongue. "And best friends shouldn't be doing this," she says, then grabs my face with her hands and pulls my lips to her neck. As I run my tongue from her neck down to the top of her cleavage she moans and pulls me back to her mouth for another hungry kiss.

"I'm sorry, I just can't control myself," I tell her in between kisses.

"Ohhh, I don't want you to," she replies as she feathers my neck with light kisses. "But we need to be careful." I feel her tongue on my ear. "I'm going to go get in the shower. Maybe that will calm us down." She gives me one last peck on the lips then turns and walks toward the bedroom door. She looks back at me over her shoulder and says, "I guess I won't be needing this though." At that she pulls her arms out of the dress and lets the dress drop to the floor. I am treated to a majestic view of her naked back as she steps out of the dress, still wearing her four-inch heals. Then I notice that she is wearing a sexy black thong and nude thigh-high stockings. She pauses and says, "I'll be right back." When she looks back at me over her shoulder I can see the outline of her generous breasts as they hang at her side. Once again my cock is straining at my pants. She walks into the bathroom and I hear the water start to run.