Kelly and the Boss

Kelly and the Boss
By: babydoll06 (notaworryintheworld@hotmail.com)

I've had a rather recent obsession with older men. Not a lot older, maybe ten or fifteen years older than me. I'm still young, just a few months shy of being able to order a drink at a bar. Most of the guys my age are still terribly involved in binge drinking and frat parties, and while I've had a few decent lovers my age the general population of twenty year-old males are lacking in bedroom know-how. Men as few as five years older than myself behave very differently. They know where they're going in life, are tired of the frat party scene, and have picked up a few bits of knowledge on how to please a woman.

Aside from being obsessed with older men, I'm especially drawn to older men who are in a position of power in my life. Like that professor I had over the summer or more recently, my charming British supervisor at work. My supervisor, Collin, is an interesting mix of many things. He is in his early thirties, a bit goofy, incredibly charming, and likes to make as many sexual comments and jokes as he possibly can whenever I'm around. Aside from his personality I think I am drawn to him because I know any sexual relationship with him would have to be a complete secret due to our professional relationship, and the thought of sneaking around and having this dirty little secret is incredibly sexy to me. But I honestly never thought anything would happen between us.

One day at work I had left my cell phone on the counter next to my purse; we're not supposed to bring our cell phones into the building and Collin, deciding to scare me into thinking he actually cared, stole my cell phone and waited for me to notice it had gone missing. I didn't notice until the end of my shift and he didn't really say much before giving it back to me. The next day was my day off and I got a text message around noon from Collin. I immediately realized that Collin had kept my cell phone number and programmed his own number into my phone. The message he had sent me read: "I miss you! Or maybe I just miss your ass. Tom's working and you're ass is much nicer than his." I was a little surprised but wrote back that comparing my ass to Tom's wasn't much of a compliment.

We continued to message back and forth for the rest of the night, the conversation becoming increasingly sexual. But the next day at work everything seemed pretty normal. There were the usual sexual comments but nothing as intense as the text messages of the night before. While on my lunch break I realized I had a new text message from Collin. "You look so hot in those pants I can't concentrate on work." I didn't quite know what to make of it and just laughed it off telling him that I'd go home and change if I noticed him drooling.

Our text message conversations continued over the next few days and we both all but admitted an intense desire for each other. Finally Friday came and my roommate dropped me off at work and borrowed my car because hers had died. I asked Collin, who was the only person closing with me who lived in the same direction I did, if he would mind giving me a ride home. He agreed to drive me home and the day continued as usual.

At one point in the evening Collin casually asked me if I had any plans after work. I told him that I didn't really have any plans aside from just drinking with whoever was around. He told me that he was having a couple of friends over and they were probably going to play a little poker and watch a movie or two and that I was welcome to join them if I wanted to do something other than the usual old thing. At that point I still wasn't sure if all of the sexual comments were serious or all in fun so I was rather surprised when he invited me to his apartment to hang out with him and his friends. I decided to take Collin up on his offer, figuring that a change would be fun.

After the store closed and most of the other employees had gone home I found Collin walking behind me as I checked the store for any straggling customers. "I'm picturing you naked," he finally said after a few moments of silence. I squealed in flirtatious and fake horror and covered my butt with my hands, stopping short to make him walk past me. "That's fine," he said, turning around and walking backwards, "I think I like this view better anyway." I gave him a devilish grin and turned down an aisle he had just passed to continue walking the store. He went about his own business and the next time I saw him we were both ready to leave.

When we got to his apartment he had a message on his answering machine. His friends had a change of plans and were now going to a strip club instead. "Looks like I'm back to doing the same old thing," I said, assuming that Collin was going to want to join his friends at the strip club. "What? You don't want to hang out here if I'm the only one around?" "Oh, well I just figured you'd want to meet up with your friends" "And spend yet another night at a sleazy strip club watching nasty women shake their asses for a few bucks? No thanks. But it's up to you, if you want to stay here we can pop in a movie and have a few drinks or I can give you a ride back to campus." "Well, I'd hate to leave you all alone with no friends," I said, taking off my coat, "so I guess I'll stay for a little while."

Collin went into the kitchen and mixed two rum and cokes while I went and looked at his movie collection. I finally settled on an Adam Sandler movie and plopped down onto the couch. Collin handed me my drink and then put on the movie before sitting on the couch next to me, a lot closer than I had expected. I had sat rather close to the edge of the couch but instead of sitting towards the other end of the couch Collin sat right next to me, leaving barely any room between our two bodies. I couldn't help but think of all of the erotic text messages we had sent each other and felt slightly embarrassed when I felt myself getting a little warm between the legs.

Despite my slight discomfort I managed to engage in small talk with Collin as he set up the movie. We talked mostly about work but I quickly realized that his mind was as far from the conversation as mine was and I finally got the nerve to mention his text messages. At first he tried to claim that he just liked giving me a hard time but I could tell it was something more than that. Eventually I got him to admit to his sexual interest in me when he said, "well who wouldn't want to flirt with a hot young woman like you? A guy can dream can't he?"

The fact that I now found myself as the object of a rather attractive older man's fantasies overwhelmed me, and without even realizing it I was suddenly half on top of my manager kissing him passionately. As soon as I realized what I was doing I pulled back as suddenly as I had started the kiss, feeling embarrassed. "God, you're hot," Collin said, after sitting and looking at me for a while, "but this would be so wrong, I mean, I am your boss after all." I felt so embarrassed, I even contemplated quitting right then. "The only way it wouldn't matter is if nobody ever found out." Collin's comment surprised me. I had expected him to end things right there, assuming that the most I would ever get from Collin was a lot of excessive flirting. Little did I know what more Collin was prepared to give.

Collin moved closer to me, rubbing his hand up my arm. "You have no idea how long I've wanted to do this," he said, moving in and kissing me fully, passionately on the mouth, his tongue easily sliding into my mouth to intertwine with my own. I melted in his arms. He was in complete control of me, my body was his for the taking.

As we continued to explore each other's mouths with our tongues Collin's hands roamed all over my body, and I barely even realized when he took my shirt and lifted it over my head. He paused our kiss just long enough to slip my shirt off of me and look down at my now barely covered chest. He ran the back of his hand down my cheek, over my neck, and down the center of my chest, feeling the soft smooth skin of my breasts. I had already become extremely aroused but I knew it would be a while longer before Collin was going to give me the release I already so desperately needed.

Collin's hand continued to move down my body, over my tight and smooth tummy. As his hand reached my waist he leaned over me more, causing me to slide underneath him. He moved his hand slowly back up my smooth bare skin, sliding his hand around to my back and quickly finding the clasp of my bra. Like an expert he quickly released my boobs from the bra's hold. I helped him to slip the bra off of my arms, exposing my pert breasts to the cool air of the room. My nipples were instantly hard. Collin's gaze down at my exposed body was driving me crazy.

He leaned down and kissed my mouth, letting me draw his tongue into my mouth. He broke the kiss and gently nibbled my ear, moving his mouth down my neck in slow kisses. His kisses followed the line of my collar bone and then descended down my chest, he stopped right between my boobs and looked up at me with a sly look.

He never even touched my boobs, but instead of giving them the attention they so desperately needed he continued to kiss down my tummy, pausing to kiss circles around my navel. The entire time he had been kissing his way down my stomach he had been undoing my belt, and then my pants, without me noticing; his movements were so slight and I was so focused on his mouth that I didn't realize what he had been doing with his hands.

Now that my pants were undone Collin began to tug at them and I lifted my ass off of the couch so he could easily slide them down my legs. Once my pants were off and I was now laying below him in nothing but a thong, Collin kneeled above me taking in my body below him. He took the opportunity to remove his own shirt and then lowered himself to me, kissing me full on the mouth again. "You're so fucking beautiful," he breathed into my ear with his heavy British accent. My hands were roaming all over Collin's back and up into his hair as he again began to kiss down my body, this time taking the time to kiss all over and around each of my breasts, giving plenty of attention to each nipple, swirling his tongue around each one and sucking them into his warm mouth. As he began to kiss down my tummy his hands replaced his mouth on my boobs and I was now breathing hard from all of his stimulation.

Collin continued to kiss down my stomach and over my thong, which was now damp from my excitement. He came to rest directly over my clit, kissing there with extra pressure, and looked up at me. My hands were in his hair, urging him to continue his oral exploration of my body. His hands slid down my sides, sending chills over my bare skin. Once his hands had slid down to the top of my thong his thumbs slipped under the waistband and slid the flimsy and soaked piece of clothing off of my body.

I was now completely naked and pinned under my supervisor. We were both glistening with the sweat of our excitement and couldn't keep our hands off of each other. My hands roamed from Collin's short blond hair to his back, over his strong arms, to his smooth chest and pert nipples. I was squirming under him, begging with my body for him to give me release. Collin's hands ran up my sides, over my boobs, gently pinching my nipples, over my arms, down to my tight round ass, back up over my stomach. He looked up at me with lust in his eyes as he slowly lowered his face to my dripping cunt.

The moment his tongue hit my clit my body felt ready to explode. He had spent so much time teasing me and bringing me up slowly that this direct stimulation was almost more than I could take. His tongue moved slowly, barely touching my skin at first, down to my wet hole then back up to my clit again, slowly increasing the pressure with each pass. After several passes up and down my dripping cunt Collin stopped at my clit again, this time sucking the now very hard nub into his mouth. I moaned loudly, unable to speak and barely in control of my body.

While continuing to suck and lick at my clit Collin slowly pressed a finger into my dripping cunt. My hips instinctively raised to meet his finger, taking all of it into me. He slowly pulled it almost entirely out of me and as he began to work it back in I realized he was working a second finger into me. He continued with a slow pace, driving me crazy and making me desperate for release.

He continued to finger my cunt as he kissed back up my stomach and eventually he was high enough that I could reach the buttons of his pants. I undid his pants as quickly as possible and attempted to pull them off of him. Getting the hint, Collin pulled off his own pants along with his boxers, leaving both of us naked. I looked down at his cock, which was now extremely hard and pointed right at my cunt. It had to have been at least eight inches long and two inches thick.

Collin kissed me hard on the mouth before whispering in my ear again. "Do you want me to fuck you baby?" he asked. It was all I could do to moan a barely audible "yes," as he continued to kiss me around my ear and on my neck. I felt his stiff cock rub against the lips of my pussy ever so slightly. "Are you sure you want me to fuck you?" he breathed heavily into my ear. This time I was desperate and forced out a loud "yes, please fuck me!" I felt his cock at my pussy again, this time a with a little more pressure but he still wasn't going to enter me.

"How bad do you want it?" He asked me between kisses on my neck and mouth. "Oh, Collin," I panted, "I want you so bad I can't even stand it. Please, Collin, fuck me!" With that he rubbed the end of his cock up and down my cunt a few times before slowly beginning to burry it deep inside me. I moaned loudly as I felt his cock filling my tight pussy. It had been several months since I had felt a man inside me and Collin's massive member was almost more than I could take. He stopped once he had stuffed the entire length of his shaft inside of me. "How does it feel, baby?" He asked me, keeping his cock deep inside of me. "Like...heaven..." I gasped. I was so close to the edge I could barely breathe. My head was spinning and I thought I would just die if Collin didn't bring me to orgasm soon.

He pulled out even more slowly than he had entered me, leaving only the very tip of his huge cock inside of me. I wanted him in me so bad I pushed my hips up to try to take him into me again. Collin realized what I was doing and pulled out completely. "Don't be a naughty girl and rush," he said, "or you won't get anything at all." After that I knew that I was completely in his control and I couldn't stand it; I had been reduced to begging. "I'm sorry Collin," I pouted, "I'll do whatever you want, I swear, just fuck me baby, please just fuck me."

"You want me to fuck you?" He asked with a grin on his face. Without giving me a chance to respond he pounded his cock into me. I thought I might split in half. I grunted as his cock filled me. "Is that hard enough, or should I fuck you harder?" Collin withdrew quickly and then slammed his cock into me again. He repeated this a few times before pausing again with his cock filling me. "Now are you going to let me take control without interrupting?" He asked. All I could do was nod, I wanted release so bad I didn't care what he did to me.

Collin began to move his cock in and out of me in a slow and sensual rhythm. He kissed my mouth and my neck and whispered in my ear telling me how hot and sexy and beautiful I was. Just feeling him inside of me was bringing me close to the edge. His large cock inside of my tight cunt was like heaven, and it overwhelmed me. He slowly increased his speed until he was pounding his dick deep inside of me in hard fast strokes. I was ready to explode and could tell that he was getting close to the edge as well.

Just as I felt my orgasm wash over me and began to shake uncontrollably I felt Collin release his load deep inside of me. He gave one final hard thrust and then held his cock deep inside of me, letting his cum fill me. Feeling him cumming inside of me made me orgasm again right away and I quickly went limp under his body, moaning with pleasure. Collin soon collapsed on top of me, continuing to kiss my neck, cheeks, and mouth.

He laid there on top of me on the couch for a few minutes before sitting up and taking my hand and pulling me up to a sitting position. "What do you say we take this to the bedroom?" He asked. Without responding I stood up and followed him naked to his bedroom.

Collin sprawled out on his king size bed and I quickly went to work reviving his cock. I started at the end of the bed and crawled seductively up onto the bed over his legs and settled over his cock. I bent down and slowly began licking at his cock, spending extra time on his balls, taking each one into my mouth and swirling my tongue around it before licking back up his shaft. I worked his cock slowly, easing back to its full hardness. Once he started to get hard again I spent extra time on the head, kissing it, swirling my tongue around it, and taking it into my mouth. I then slowly started to take his cock into my mouth, bobbing up and down on it, each time taking more and more of his quickly growing member into my mouth. By the time my lips reached the base of his cock I had half of it stuffed down my throat and was bobbing up and down rather quickly. But I didn't want him to cum again just yet. Just when I thought he was nearing the point of no return I slowed down dramatically and eventually removed his cock from my mouth completely.

I stood up slowly, giving him full view of my still naked body, glistening with sweat and the juices of my damp pussy and then slowly began to squat down over his now very erect penis. I paused with his dick barely touching my pussy and stared him in the eyes, daring him to try to enter me. He showed incredible self-restraint and resisted the urge to push himself into me. I smiled as I lowered myself a little more, so that his cock was very near entering me but not yet inside of me. I watched his face. I could tell it was all he could do not to push himself inside of me but he remained almost motionless on the bed. I finally lowered myself slowly onto his cock until the entire thing had impaled my tight pussy. He moaned in delight. "God you are so fucking hot," he said, reaching up to fondle my pert tits.

I rubbed my hands over his chest as I began to rock back and forth on his cock. Riding him made him deeper inside of me than ever before and I knew I wouldn't have to wait long for release. At first I rode his cock slowly but I was soon moving quickly and bringing myself very close to orgasm. It wasn't long before it hit me and I pushed myself down hard on his cock and let the wave of pleasure wash over me. When my orgasm passed I slowly lifted myself off of Collin's still swollen cock. Missing the feeling of having him inside of me I slowly dropped down letting him fill me again. I did this several more times before standing up again and kneeling with my head at his cock yet again.

I began to lick and suck at his cock again, quickly filling my mouth with his cock and pumping it hard and fast in and out of my mouth. He was moaning and had his hands in my hair, pushing my mouth down hard on his cock. "Oh fuck!" he moaned loudly as he shot his load deep into my throat. I held his cock deep in my throat as he came and swallowed nearly all of his cum and he came until cum was dripping out of my mouth. I slowly pulled his cock out of my mouth and then used my fingers to collect all of the cum that had dripped from my lips and sucked it off of my fingers.

Collin pulled me to him and we both soon fell asleep wrapped in each other's arms; neither of us caring about how this sexual excursion may have effected our professional relationship.