by Jamie Knight
“What’s the prize?” I asked.
“An all-expenses paid trip with me to the Bahamas for two weeks. On a cruise.”
I was buzzing. Two weeks in the Bahamas with Max! Outside of official work so there wouldn’t be nearly the stigma. If anything was going to happen between us, it was going to be then.
I could just imagine us walking on the beach as the sun set, finding some secluded spot and fucking until we both came. It would be beautiful. I had to win the competition.
“What do you think?” He asked, pulling me out of my reverie of plots and potential villainy.
“I think it’s a great idea! I know lots of people who would like that prize. I mean, who wouldn’t want to spend two weeks in the Bahamas? Except maybe someone really pale.”
Shit. I was talking too much. Not least because I was really pale. I didn’t want to accidentally disqualify myself with an ill-placed comment.
“Good. I’m glad you agree,” he said, seeming to mean every word of it.
I had heard him with Mitch Peters, the P in MP Solutions and knew that they both had a gift for sarcasm exceeding either god or man.
“When does the competition start?” I asked.
“Monday, so I need you to rest up okay? I’m going to need a lot of help keeping track of things.”
“Yes sir!” I said a bit of emphatically actually saluting.
“Glad to hear it,” he chuckled.
We hung up and my mind was dancing with wonderful visions of the two of us in paradise. All alone, except for the other person who got chosen. In a way, the fact there were going to be two winners eased my guilt a bit. I had never been that competitive growing up because there could only be one winner. Strange for a theatre kid, auditions were mostly a zero-sum game, but I wasn’t really thinking about that at the time.
My mind was on the crushed dreams and all the ones who didn’t make it. I wasn’t dismissive of such realities, just oblivious to them. I was sure that if I worked hard enough, my talent would carry me through and get me jobs simply by being the best for them. Meritocracy in its purest form. I could really be naïve.
Returning the phone safely back on the nightstand, I rolled onto my side again, careful not to wrench my back. I could really only sleep on my side. The accident had been a couple of years before, but the doctors said at least some of the damage would be permanent.
I could still do most things, some of them just needing some slight adjustment. Putting everything in lower shelves. Sleeping on my side. Baths instead of showers. Finding a place with a full bath in my price range was next to impossible.
It hadn’t really affected sex that much. At least not as much as I thought it might. Not that it came up very often. I wasn’t a virgin, but it was just barely. My sexual experience basically came down to the one time. Which was fine.
I really wasn’t into the guy. I just wanted to see what the fuss was all about. It was something I would regret probably for the rest of my life. It really shouldn’t matter, but I really hoped I would lose my virginity to the man I loved. I didn’t realize just how soon I would come across him.
Max really was the perfect guy. Perfect for me, anyway. Everyone had their own perspective and preferences and all that. But most of my thoughts, sexual and otherwise, involved him in some way, and I got a very specific tingle in my pussy every time I saw him. Really, if that wasn’t love, I didn’t know what was.
My hand slid down from my hip to my belly. So slow and gentle I barely noticed. Then it stroked along my belly getting closer to the band of my panties, rather piquing my attention. Apparently, my hand had plans my mind didn’t know about but was more than happy to go along with.
Using my other hand to pull up the waistband, the other continued its journey downward, finally settling on my tender pussy lips. Even that light touch sent a jolt right through me. Just feeling myself for a moment, giving my mind and body a chance to get into sync, I tried again with slow, light strokes along my tender pussy lips. A soft moan escaped me, and I knew I was on the right track. After a bit more stroking, I slid a finger inside and closed my eyes.
I could feel his breath on the back of my neck. Its light touch soon turned to that of his lips as he planted warm, soft kisses back there, making me hum with contentment. Kissing his way down my bare back, one of his hands came around to gently play with my tits as he worked his way down along my spine. Each kiss made me tremble.
Working my panties down and then off, Max gently re-positioned my legs, so my knees were up near my tits. It felt a bit strange, but it didn’t hurt my back and when he buried his face into my sweet little pussy, the pleasure chased all other thoughts out of my mind.
With one hand on my thigh and the other on my ass, he gently massaged me as he licked. Stroking his tongue in a swift, deft motion the length of my pussy, pausing for a swirl on my clit every so often just to shake things up. As though it weren’t already quite interesting enough. Gorgeous Max made me feel like I was in heaven just with his tongue and hands. If only I knew what he had in store for me next.
Licking me to a soft orgasm, more than enough to get me nice and wet, Max got up on his knees, hovering over me like a sexy guardian. Planting one arm behind me, he slid his massive cock slowly into the gentle pink folds of my tight, young pussy. My little cunt seemed to hug him in welcome as he pushed in. The fit was very cozy indeed but didn’t feel anything but good. Nonetheless, my beautiful Max gave me a moment to adjust to the feeling of having his monster cock inside of me, which I very much appreciated.
Putting his other and down by my knees and hooking his arm up behind them to hold me in position, he slowly started to move. He worked my pussy with slow pumps, letting me feel it as the joy trundled through me. I shivered with the most delicious pleasure.
But that was only the beginning. By the time he had worked his way halfway into my pussy, I had stretched out enough to let him go hard. He was still a bit cautious at first. I could tell he didn’t want to hurt me. I gently squeezed his nearest forearm and nodded, letting him know he could go hard.
Taking the signal, he started to pound me. Slamming his massive cock deep into my pussy. His beautiful balls were banging rhythmically against my ass cheek as Max literally fucked me sideways, bringing the most glorious songs of praise up from my soul and accentuating the distinctive sound as his cock demolished my pussy.
Letting me cum first, Max slipped two fingers in me and worked my pussy to another orgasm as he came around to the front of the bed to generously feed me his gorgeous cock. I really didn’t know what I was doing, being somewhat new to the world of blowjobs. I knew only enough to know how little I knew.
I didn’t need to worry myself. Max seemed to understand perfectly, He held my ponytail lightly as he tenderly fucked my warm little mouth. All I had to do was keep up with his thrusts, sucking him as hard as I possibly could as he worked in me. The result was a wonderful gush of hot, sweet cum filling up my mouth. My eyes rolled back as I swallowed it all down.
I came hard, shuddering under the duvet, which had been the first thing I’d bought after arriving in the city. I had some money from summer jobs and still little conception of how much things could cost there. Cleaning off with some wet wipes from my night table, I got out of bed as carefully as possible and pulled on a dress to go and try and have fun on my last weekend before I would compete for my future with Max.
Chapter Five - Carrie
I don’t like Mondays. Though my antipathy was more of the Garfield type than the Boomtown Rats variety. It wasn’t even really work related. Were it not for the risk of permanent injury, I would have leapt out of bed and done a little happy dance around the room every day I woke up to go into the office to the job that I loved and the beautiful boss who never failed to make my panties damp.
The problem was with everyone else. I don’t mean that in a narcissistic way of blaming everyone but myself. I get that life ca
n suck and that Mondays and Fridays were the worst days for traffic. I might have loved my job, but it would seem like I was the only one. The dark and soulless dirge to the beginning of another work week so many seemed to be dragging themselves to would have been heartbreak were it not also so very annoying and not in the cute way.
It really did baffle me why so many people lived in the city when so many of them seemed to hate it so much. As evidenced by the near cut-throat competitions for camping spots come any kind of vacation. Lake houses came to be some kind of status symbol, a home away from the home they hate but pretend not to.
I tried to put my game face on. I never really did sport, unless you count theatre sports, otherwise known as improv. So, I really wasn’t sure what a game face looked like. Nonetheless, I gave it my best shot. Looking at myself in the rear-view mirror, I tried on different looks as traffic sat at its usual stand still, going from stone cold serious to teeth bearing and scary. The entire progress was facilitated by “Don’t Rain on My Parade” in my earbuds to get me into the right headspace.
By the time I got in to work I was nearly strutting, barely noticing the small back brace that I wore to keep me from throwing my back out while filing. I gave a moment’s thought to wearing high heels to make my legs look even better than they usually did but decided that this would be a bridge too far.
I arrived on time for the first time in weeks. Through a lovely twist of fate, Lady Lauren did not. She came in a full half hour after I did. I didn’t say anything but made sure I was at the water cooler so I could give her a very significant smile as she steamed past. Two inches closer and she would have body checked me into the wall. Petty as it was, my smile grew, delighted by the fact I was able to get into her head.
Properly rehydrated, I returned to my office, my earbuds giving me the gift that was “Do You Hear the People Sing?” I strode to my corner office to prepare for the first day of recording. The sun streaming in through the window seemed a very good omen.
I was still a bit nervous about seeing Max again. Especially what had happened at lunch the previous Friday. He had apologized of course, and I was never really all that angry. I was sadder and more hurt. But knowing he wasn’t trying to do that actually did make me feel better. It didn’t mean that he loved me or anything, but he was obviously concerned about my feelings and cared about my opinion since he still bothered to tell me about his plan and wondered what I thought about it.
He called me at home, no less. For some reason, that felt a lot more intimate than a working lunch. It was like he was there in my place, even if it was just his voice. That was probably why I imagined him in the bed with me. In some weird, meta way he had been.
I could feel my pussy getting wet just thinking about it. But it was too early in the day for me to take one of my trips to the bathroom, so I just had to suffer through. I was a professional and was going to bloody well act like it. Closing my eyes and getting into a Zen state of mind, I booted up my computer and started doing my best to get as many new clients as I could as I waited for the moment when Max would call me into his office to serve him.
I had a long wait. I chased and closed three new clients somewhere in the middle of the prestige list, an actual paper list next to my computer, before it happened.
“Come in?” I said, not really used to anyone knocking on my office door.
“Hey,” Max said, coming in closing the door behind him.
“May I?”
“Please,” I said, trying not to beg.
He came in and sat down in the chair on the other side of my desk, technically putting me in the position of power.
“How are things going?”
“Good, I just closed three accounts.”
“Wow,” Max started, genuinely surprised.
“Working hard for you, sir.”
“Glad to hear it, Carrie.”
Another tingle. That time in my tummy. The look in his eyes and the softness in his voice sent my hormones wild.
“Trying to win the contest, sir,” I confessed, without really meaning to.
“Contest?”
“The one for the agents. I think it is a really good idea and am trying my best to win. Or be one of the winners anyway.”
“Oh, no, you aren’t eligible for the competition.”
“What?” I asked, almost hearing my hopes of getting to know him in a more casual setting being crushed.
“As my assistant, you would be coming on the trip with me anyway. I need to leave both spots for winners clear for the other agents.”
I hadn’t thought of that. I was so used to my dual role I had come to think of them as separate things. Of course, I would be going with him! I felt both embarrassed and relieved. There was a chance after all, and I wouldn’t have to win to get it.
“Right, of course,” I said, trying to keep it cool.
“I’m also going to need a lot of help. It is going to be a lot of work recording who to bring and I’m going to need some eyes out there keeping track of things. I want you to go about your job as an agent like you usually do. The main thing I need your assistance with is the competition.”
I hadn’t really thought about it that way before, but it made sense after he explained it. I was no dummy myself, but Max had a way of seeing things that was really amazing. It was still mostly a hope, but there was a chance that with the money from Whitman and my work on the competition that I might get a raise in terms of both my jobs, which would keep me in my apartment a lot longer.
“I’m going to go and get back to work, but I would like a progress report at the end of the day. Nothing too rigorous. Just your general impressions. You don’t even have to write it out. Just come in at the end of the end of the day and tell me what you’ve seen.”
“Yes, sir.”
“Good girl.”
At least that was what I thought he said. He got up and left the office before I could ask. He could have been teasing, picking up on the number of times that I’d called him sir. But it didn’t sound like it. At least not what I’d thought I’d heard. If anything, I would have described it as affectionate.
The rest of the day floated by like a dream. Securing two more clients for the firm, I still wanted to do my best to impress and help Max even if I was already going on the trip. I was honestly trying to get his attention any way I could. Though I definitely preferred that it be in a positive way.
Leaving the door to my office open, I continued to look like I was working at my job as an agent, while having actually switched gears to my other work for the firm. Being Max’s right hand, which in that case basically meant a bit of mild espionage.
Spy work was not as interesting as movies made it look. Partly because things were pretty much how I thought they would be. Thomas was a workhorse. Adam was doing his best. Steve was still working on his first client. Morgan was kicking ass and taking names and Lauren was being a total bitch.
Were I to put money on it, I would guess that Thomas and Morgan would be the two chosen to go to the Bahamas with us. Funny how that’s how I was beginning to think about it, but it really was true. In terms of running the office, Max and I were a unit. He needed me and I wanted to do my best for him. Even if I also wanted to be his partner in another way.
I tried to focus but still probably had enough. Even as my imagination started to take over my conscious mind and put me into a daydream, I knew I would still have something to tell him at the end of the day.
I imagined us walking down off the plane into the beautiful sunshine, the two winners behind us where I couldn’t see them. Not that it was at the forefront of my mind at the time. We were still keeping up appearances even in my daydreams. My basic cautiousness was too much a part of my personality to be ignored. Still, it was nice just to be there with him without the pressures or expectations of the office.
We were already dressed in a much different way. Even Max w
ent for khakis and a light blue polo shirt. I was really as casual as I had ever seen him. It gave me hope, even literally in my dreams, that there could be a chance for us. The hope got even stronger when we got to the hotel, a beautiful resort housed inside a really old building right by the water.
Max did everything. The three of us waited for him to give us our keycards. Except when it came down to it, there were only three card envelopes given out. There was one each for the two winners, but the two cards for Max and me fit snugly into the same envelope. We would be sharing a room. Something he had to have planned because he made all the arrangements for the trip.
I was wrong. Or, more accurately, I had underestimated the situation. Not only was there one room for the two of us, there was also one bed. It was an ancient and beautiful four-poster, set wide across the back wall. Technically, there was enough room for us each to have our own side and then some. I was pretty sure I could stretch my arms out to full length and still touch nothing but sheets. A gap could also be easily closed should such an action be wished.
Suddenly shedding my usual shyness, at least when it came to Max, I didn’t even go into the bathroom before changing into my bikini. Stripping right down to nothing, I wasn’t wearing my brace in my daydream. Suddenly regaining my full range of motion, I took my time finding my bikini in my small suitcase. Max watched every second with close attention. He didn’t touch me at any point, but I could feel his eyes on me. His gaze caressed every inch, making me suffer subtly with delight, as though it were his hands.
I had heard about the softness of the sand in the Bahamas, like walking in fresh flour according to the anecdotes. I imagined walking a beautiful stretch of it, the water sparking crystal blue in the sunset. Max held my hand as we strolled. Our strides nearly matched. Max’s longer legs gave him a distinct advantage.
I caught him glancing at my barely covered boobs out of the corner of his eye. Still holding his hand, I reached around behind my back and unlaced the string on the top on my string bikini. It fell away, revealing my tits. My nipples were instantly hard from the gentle touch of the ocean breeze.