Doin' the Boss Ch. 01

The problem with doing your boss, your married boss, your lives in suburbia, two rugrats in the living room and another bun in the oven, perfect as all get out boss, is that the odds are stacked against any real relationship.

Let's face it, he has too much too lose and you are expendable. I know, because I found that out first hand when I had just turned 20.

It was six years ago, but it seemed like yesterday. As a fresh graduate of the Pauline K. Gibson Secretarial School, I made the rounds of the banks in Philadelphia looking for an entry level secretarial job. After several unfruitful interviews, I happened upon the Second National Bank Corporate Headquarters where I met a harried Human Resource Director.

There, in my prim and proper business suit which displayed just a touch of leg, I did my best to make his A List of candidates. As luck would have it, a Friday resignation led to a Monday opening, and I made my way to the Credit Processing Department where I met, and immediately hit it off with, K. Lawrence Little. Mr. Little was a good-looking, wise cracking man who ran the department of 25 processors.

Our guidance counselors continually told us that even with impeccable credentials it might take a while to secure a good position, and that it almost never happened immediately upon graduation. This was my lucky day, because after an hour of questions I had made enough of an impression, possibly helped by his immediate need, and the following week I began my working career.

Ours was a good match. Mr. Little, a 35-year-old who had an infectious smile and the wit to go with it, was a great boss. He guided me through several minefields, as every new kid on the block needs but seldom receives, and was patient with my numerous miscues. Along the way I grew under his tutelage, became a model of efficiency, and we began to work closely as a team. Maybe too close.

In some ways Mr. Little was like a father to me. He would provide advice on everything from finances to boyfriends. He was concerned, not angry, one Friday after my boyfriend and I spent a little too much time dancing and carousing at the Jersey Shore and didn't make it back home until nearly 2 a.m. I was late for work the following morning, but instead of reaming me out and giving me all the grief bosses are supposed to give their subordinates, he at least partially understood and gave me a pass on the pontificating.

A few weeks later though, after being stood up for the third time in less than a month and spending much of the day one short step from breaking into tears, Mr. Little asked me to stay after work. He listened to my story, told me it wasn't the end of the world, and that there were other fish in the sea. Then he told me a few jokes, clearing my mind before gently sending me on my way.

He earned my respect that day, and continued to do so when he helped me with understanding my finances, cautioning me about certain wolves in the building, and being a perfect sounding board for everything from career to personal goals. At the annual holiday party he introduced me to Mary, his pert little wife, while I introduced the Littles to Mac, also known as Malcolm, my then-current beau. The four of us laughed, danced and enjoyed the party.

Several weeks later Mr. Little mentioned that Mary had another child on the way, the product of an alcohol-induced session of hanky panky the night of the holiday party. I laughed and congratulated him, and we joked about how there must have been some viagra in the punch or something.

It was one of those innocent comments that came back into our conversation several weeks later. It's a long story and I won't bore you, but suffice it to say that Mac and I had been having difficulty in the sack in recent weeks. Now I had never been all that sexually active, Mac was only my third lover, and technique was not something that 20-year-olds pay much attention to.

I lost my virginity to Jack the summer he was heading off to college while I was a naive 18-year-old high school senior. Jack got into my pants in the back seat of his Buick while we were parked alongside Tinicum Lake. I had satisfied him with handjobs for several months before finally giving in to his insistent desires after he professed his lifelong love for me. It wasn't pretty, and I lived in mortal feat of pregnancy over the next month after he told me his condom had somehow come off during our initial intercourse.

When I finally got my period I swore off sex forever. Forever lasted about 18 months, as William and I were busy as bees in the bedroom, and his car, and his parents house, and wherever we could find a few minutes and a bit of privacy. William had a constant need for sex, and I swear he was fully ready to go a second round after just finishing his first. William taught me to suck his cock, to wear sexier outfits and to satisfy his guttural urges with a smile. I loved him, he loved me, and we were a perfect combination in and out of the bedroom. Or at least I thought.

When he left me for Jenny Constantino, the rich bitch from uptown, I nearly died. Mr. Little helped me through that down period of my young life, and reminded me "you have to get up and ride after falling from a horse!"

I listened, but didn't believe it. My heart was broken, but time does heal all wounds, and soon Mac came along to divert my attention from hating guys to, well, liking them once again. I was attracted to Mac more than any other man, and soon we ended up sleeping together whenever we could. The sex was exciting but there was always something missing. I couldn't put my finger on it, but Mac just didn't ring my bells. The rest of the relationship was good, but for some reason Mac wasn't very affectionate. He said he loved me, but he didn't really like to hold hands, caress me or all the thing that make a girl seem special.

One Friday night before shutting down the office Mr. Little and I were casually talking about the upcoming weekend when I asked him what he did to make his wife Mary seem special to him. He talked about flowers, candlelit dinners and reminding her of how good she looked, but said every man was different. I lamented that I just didn't feel truly loved my Mac, mentioning that I even felt I didn't turn him on.

"I've caught him looking at other girls, and I don't think he looks at me that way," I dejectedly said

"Ah, your crazy, Constance, you're nuts," said my boss, hesitating a bit.

"What is it Mr. Little, tell me!"

My boss shuffled a bit in his seat. "It's just I don't want to say anything inappropriate, I don't want to get in trouble with HR or something."

:"Geez, Mr. Little, you can say whatever you want. You don't have to worry about me, I'm a big girl. Tell me."

"Ok, ok, Constance. It's just that you are very pretty and I can't imagine any guy not getting turned on my you!"

He went on to tell me how good I looked at work, and that I looked absolutely great in the cocktail dress at the party. He said many men there had stolen glances at me that evening, bringing a crimson blush to my face.

That weekend I thought a lot about how sweet my boss was. I also thought about him in bed…fantasizing about him when Mac was thrusting in and out of me. It was the first time I had ever thought of someone else while screwing, and it was both naughty and nice. I had an orgasm that night, one of the first ever with my boyfriend.

I didn't know what had come over me, but I had this desire to, well, see if I could excite my boss. I'm not talking trashy here, I wasn't going to start dressing like a slut, but I did begin wearing my dresses and skirts a little shorter and my sweaters a little tighter. I didn't wear something inappropriate like miniskirts, but I did show a bit more leg in the office.

I wasn't sure at first, but after a while I did catch Mr. Little catching glimpses of my legs when he would talk past my desk. When I sat in his office taking dictation, I caught him a couple times peeking up my skirt. It was hot knowing he was looking.

Several weeks of my innocent exhibitionism went past and my little leg show continued to excite most likely Mr. Little and me too. At one of our late day meetings I caught him looking right up my short blue skirt, and asked him what he was looking at.

"You know what I am looking at, Constance, you are a true temptress!"

I laughed, calling him a naughty boy.

"You really should start wearing your skirts a little longer, Constance," instructed my married boss. "It is, well, distracting."

Thinking back, I have no idea what got into me that day. I looked him in the eye, then down to my lap. I moved my legs slowly apart and leaned back just a bit. Looking up, I saw his eyes had followed mine to my midsection…they were glued up my skirt. I wondered if he could see my black satin panties.

"Do you like the view, Mr. Little? Are you being a dirty old man?" I quizzed, fully knowing the answer.

"You don't know what you are doing to me, Constance."

I smiled. "I think I can imagine."

There was a quiet pause before I smoothed down my skirt and stood. I walked to the door, closed and locked it, then walked across the room toward Mr. Little's bookcase. I bent over in mock interest in a book on the bottom shelf, displaying a lot of thigh and maybe more.

"Constance! Do you know what you are doing?"

"I'm just looking around your office, Mr. Little, why, is something wrong?" I incredulously said.

I don't know what came over me. I can assure you that I never planned it, I surely was only teasing the man a bit, but in the heat of the moment something more came over me. I reached up under my skirt and lowered my panties to the floor. I walked to his desk and sat on it as the man was just a foot away. I slowly spread my legs.

"I don't want you to strain your eyes, Mr. Little. Is this a better look?"

I thought the man was going to have a heart attack. He sat there, staring, almost in a trance. After a bit he reached out and casually touched my thigh. When I didn't shoo him away, his hand gradually stroked and caressed my leg. When he touched my pussy, I began to melt, and when he leaned forward and began to lick my slit up and down. I had never felt anything like it, my mind swirled while my sex pulsed.

He licked and stroked by throbbing clit and made me feel sensations I had only dreamed about. His tongue stroke was slow and sensuous. He went at me like a starved man, slobbering all over my wetness. It wasn't long before I began to cum on the spot. It had to be months of built up sexual frustration or something, because I don't think he licked me for more than a couple minutes before I exploded.

Mr. Little looked up at me, and I will never forget what he said. "Oh, no, what have I done."

I think he really thought it was his fault, and that I was going to haul his ass down to Human Resources or something. I pushed him back into his seat and dropped to my knees in front of him. There was a tent in his pants, and I quickly unleashed his hardness into the open air. His cock was swelled to its full length, and he certainly wasn't named for the length of his penis. It was anything but little, stretching to at least seven inches of man meat.

I began licking the knob of it, swirling my tongue around the tip. I licked around and around, then up and down his hard cock from the bottom to the top of its mushroom shaped bead. Then I sucked it into my mouth, bringing out a groan from Mr. Little. It was an incredible feeling, his dick in my mouth. He was long, hard and pulsing and he began thrusting up and down as if he hadn't had sex in months.

His dick was like no other I had sucked. Oh, William was a little bit longer, but Mr. Little was definitely thicker. And while my other oral conquests had generally lasted only several minutes under my mouth attack, my boss stroked, pumped and pleaded for more of my mouth action yet didn't pump and explode like the others. The man clearly was enjoying himself as my head bobbed up and down his dick. He moaned, he groaned, he let me know how much he loved my mouth action.

"Oh my god, it's a dream," stuttered Mr. Little, breathing quickly. "Don't stop, Constance, it's wonderful. Play my skin flute. Oh yea!"

After a bit my mouth began to tire, so I alternated strokes of his cock between my mouth and my hand. I'd stroke him, lick him, and then stroke him again. The combination sent him higher and it wasn't long before he warned me he was going to cum. It was very decent of him to give me the option of how to make him explode, but there was no way I was going this far and not having him cum in my mouth.

"Umm, Mr. Little, it's okay, you can shoot in my mouth," I said before putting his pulsing dick back into my hot oral cavity. That was all it took as the man began shooting his tangy seed into my welcoming mouth.

That was the first of many blowjobs received by my boss in his office. Sometimes I would suck him off in his car along dirt roads and once by the lake where I lost my virginity. Once I blew him while he spoke with his wife on his cell phone, writing down a grocery list. It's a miracle we weren't caught.

Mr. Little had an insatiable appetite for having his cock sucked off. He claimed his wife wouldn't do it, and that I was the best he had ever had. It was quite exciting for me to share the secret of our clandestine meetings from all prying eyes. He'd buy me little gifts, nothing exorbitant, some jewelry for special occasions and sexy underthings for other times.

I found myself fantasizing about having a long-term relationship with the man. I loved him, after all. He said he loved me too. I wanted to make love with him in the worst way, but he told me he wanted to save that for our wedding night, then he'd guide me to my knees where I'd suck his dick.

Mr. Little insisted I continue to date, as he didn't want to raise suspicions. He even had my latest beau Jeremy and I over his house with some other friends for a holiday party. It was difficult to watch my boss and his wife make all nicey nice, holding hands and stealing kisses. But that bout of jealousy quickly evaporated when he asked me to go with him on a beer run. He stopped at a local distributor and picked up a couple cases, then quickly pulled behind the shop and pulled me close in an embrace.

"Oh, Constance, I've missed you!" he said, kissing my neck. "I need you. Do me."

He placed my hand on his manhood, and I began stroking him through his pants. His dick lengthened, and I let go of it long enough to unzip his fly. I pulled his dick out from his boxers and admired his hardness. Mr. Little had a great cock. I loved the way it stood tall and pulsed, especially when I was licking my lips and mouthing sweet nothings toward him. My boss loved it when I spoke dirty to him, and while it wasn't my favorite of things to do, I talked nasty to turn him on.

"You have such a great, suckable cock, I love it," I cooed, stroking his dick. "It's so big, so hard, it makes me wet. Let me have it, let me suck it."

"Yes, m'dear, suck it, suck my cock," he begged, pushing my head toward his hard spike in his lap. "Hurry, before someone sees us."

I gazed at his hard dick and then gingerly lowered my head to it. I knew it was to be a quickie, but still I wanted to savor the moment for a bit and started off by licking the head to get it rock hard. My short skirt rode up my thighs as I bent over and took his dick in my hot wet mouth, moving my lips up and down the hard shaft. Mr. Little caressed my ass as I blew his dick, alternating slow, sensuous sucks with hard head-bobbing in tandem with my hand strokes.

"Oh, you are a sweet cocksucker," he panted as I bounced my head on his dick. "You are the best. You make me so hot."
I loved his words, but what really turned me on was how his dick grew in my mouth as he accelerated toward his orgasm. He was super hot and I knew he had been waiting all day for my loving lips. I blew him harder and he began lifting his ass off the seat bottom, bouncing his cock faster in my sucking mouth. The pounding of my face hurt a bit, but it was soothed by the knowledge he was going to cum fast.

The man's head flew back and his eyes went to the back of his head as I sucked his cock, and with a low groan I then felt his cum erupting up the shaft of his cock. The hot sauce hit the depths of my mouth on the instroke and then continued spurting on the outstroke. He came a bucket, and although I swallowed several times I couldn't contain all of his sperm in my mouth. Some ended up on my lips, some on my cheeks, and still more on the front of my dress. Mr. Little sure loved my blow jobs! Of course I didn't notice the cum stains until we had arrived back at the house and I went to the bathroom to clean up.

Over a two-year span I must have sucked Mr. Little's cock 400 times. Five times a week for sure, sometimes twice in one day. If each orgasm produced an ounce or two of cum sauce, then I must have swallowed a couple gallons of the stick man jizz. I didn't always like the taste, but I never refused any of his oral requests. After all, I loved the man.

It wasn't until a cool winter evening that things changed between us. I didn't know it at the time, but it was going to be my final blowjob of the man. The night started simple enough, Mr. Little asking me to meet him at the mall in our "special" parking place on the top floor well away from the department store.

I left the office a few minutes before he did to deflect any suspicion and made my way to our meeting place. I parked, and soon afterward Mr. Little pulled in to the spot beside me. I got out of my car and slipped into the seat next to him, as his car had more room than my compact.

We talked for a few minutes then began necking. We made out for a while before I started to stroke his pants. I loved the feel of his lengthening cock, it made me hot thinking of how hot I made the man. After a bit of foreplay I heard his zipper opening and I bent my head into his lap and began licking his bulging cock. His hand was on the back of my head, and he alternated pushes down on his dick with my lifting my head up.

"Oh, yes, Constance, suck my dick. You are a great cocksucker, the best. Um, keep sucking me," he pleaded.

I complied with his request, licking and sucking his rock hard cock. I loved sucking him, and he loved my mouth. It was a perfect twosome. I bobbed my head up and down, licking his dick like there was no tomorrow. I heard a car driving nearby and began to lift my head off his cock but he wouldn't let me remove my dick from him as he held my head securely on his dick.

"Don't stop, honey, don't stop, Keep sucking, Don't worry about it. Suck it," he demanded and I didn't hesitate any more. "I felt his dick growing in my mouth, and just went with the flow, bobbing my head up and down on his cock. I heard Mr. Little moaning and prepared for his load. I didn't have to wait long, as the man began stroking faster and faster and then let loose with a hard series of cum spurts.

The stuff hit my mouth and face then my mouth some more as he came his usual copious load in tune to my cocksucking. He groaned, he muttered, he told me how much he loved me and my talented mouth.

I lay there in his lap, cum sliding down my cheeks when the bombshell hit.

"Mary is pregnant again, so I hope you are ready to due double duty with my dick," said the man. I couldn't believe my ears. He had told me that he and Mary weren't having sex anymore, and that I was his only outlet. Now he's telling me his wife was knocked up again. So much for his truthfulness.

I don't know what got over me, but I sat up then smacked him across the face. "You bastard," I spat. "You told me you weren't doing your wife."

"Oh come on, Constance, you know better than that, she's my wife," said my lying boss. "I have to fuck her."