TLC - A Season to Remember

Vol. 1: A Season to Remember

I own a small construction company in the South West. At the time it was big enough that I didn't get out and do much of the building myself any more, but not really big enough to hiring any office help either. Once my crews were out for the day I didn't usually see anyone in the office until three or four when the crews would start to trickle back in. I often found myself making excuses to get out and run errands or go check on jobsites, just to get out of the office for a bit. So one afternoon I was taking a long lunch, when a young woman caught my eye as she entered the restaurant I was eating in. I'm not sure exactly what I found so fascinating about her. She wasn't remarkable in any way just cute, with nice curves and a good girl-next-door look about her. I watched as she ordered then struggled with her tray and drink and the pile of paperwork she was carrying. She appeared to be quite distracted and flustered. She juggled her armload of stuff across the restaurant and down the isle that I was seated in. To my shock and amusement her load toppled just as she reached my table. Stuff went in every direction; she grabbed at everything desperately but didn't end up catching anything.

"Fuck!" she said under her breath.

I could see in her face this was just the icing on an already horrible day so I did something very out of character for me and tried to lend a hand.

"Thanks. Thanks a lot. Been one of those days you know." She said picking up the remainder of her lunch and placing it on the table next to mine.

"Hey no problem, I know what those day are like." Helping her pick up the fallen papers, I noticed that they were job applications and over the next few minutes I found out that the young woman's name was Lisa and that she was a recently out of work second year business major at the local university. And so for the second time that afternoon I did something out of character and told her to come by my office and fill out an application. She agreed and I wrapped up my lunch and left.

The next day I had forgotten about the encounter until a silver Jetta pulled into my yard. Now my office is in a small converted two story house situated in the back corner of a three acre lot where I keep my construction equipment. My office takes up several of what where upstairs bedrooms and looks out over the yard and out toward the front gate. So I saw her drive in from behind my desk and by the time I had gotten down stairs she had walked up to the main entrance and was knocking.

"Come on in." I called.

"Hi remember me? I came to see about a job."

"Yeah, yeah sure come on in." Hastily I moved some of the clutter from a long folding table that sat centered in the otherwise empty living room.

"Welcome to the conference room." I chuckled motioning to a seat at the table. For about a quarter of an hour I interviewed Alana but in truth the moment I'd seen her walking up to the front door I'd known I was going to hire her, need her or not. We settled on a decent wage, hours, and the like and agreed that she could start the very next day.

When I arrived at work the next morning Lisa was waiting and had drawn quit the crowd as all of my carpenters and construction hands gawked and stumbled over themselves trying to be the first to talk to the new girl. But after the morning meeting I was able to get them all off to their jobsites and at that point I found myself alone with Lisa. We chit-chatted awkwardly for a while and pulled a desk and chair out of the storage shed in back, then I gave her out some filling and miscellaneous office work to do and went up to my office.

I found myself distracted all day, thinking about Lisa and her nice little body. At thirty something and fully involved in a stagnant marriage my mind was all too willing to fantasize about a young college girl with perky tits and a great ass. But for the next few months I was able to keep myself in check and be a good upstanding respectable boss.

But one day about half way through the football season Lisa came into my office wearing a hooded sweatshirt with the logo of the local pro football team on it. The week had been long and trying and so I was a little irritable and when I said, "A fan? They suck this season." I said it with more sting than I meant to.

"What do you mean? Their doing fine." Lisa barked back.

"We'll see they've still go time to screw it up."

"Well why don't you put your money were your mouth is then?" I was taken back and amused at Lisa's boldness, up till then she had been very demurer.

"What shall we wager then?" I asked.

"I'm always in need of money. Hows about fifty bucks?"

"No I'd feel bad taking your money... how about your team wins you get that fifty, they loose you rub my shoulders every day during your lunch hour for a week?"

Lisa thought for a minute then with a confident smirk she said, "Deal."

That weekend came and went with a close loss for Lisa's team and all week I enjoyed neck rubs and the chance to goad Lisa about her loss. When the next Friday came around Lisa brought up the subject of coming Sunday's game while she rubbed my shoulders. "So what's the bet this week? Care to make it a hundred this time?"

"A hundred? I don't think a hundred is worth a week of back rubs."

"Well what would be worth it?"

"I don't know let me think."

After several seconds of silence Lisa chimed in, "What if I did all my work for a week in my bra and panties?"

"What!" I almost fell out of my chair.

"What? Were the only ones her all day. Besides I know you've been looking at my ass and tits, I've caught you." Lisa looked devilish as she continued, "Don't worry I don't mind. So how about it? After the guys leave I'll strip down, do my work, you can look, ONLY LOOK, and first sign of company I'm off to the bathroom to dress." Lisa paused for a moment then continued. "But really it isn't going to matter anyway because there going to win."

Stunned and speechless all I could do was nod in acceptance of the bet. My cock had suddenly grown very hard under my desk. I couldn't believe Lisa had caught me looking at her. I'd thought I'd been sly and tactful stealing little sideways glances.

"I'll take that as a yes." Lisa said as she sauntered out my office door, her hips swaying a little more than normal as she left. My opinion of Lisa had definitely changed over the passed weeks, I had really grown to find her curvy little body very sexy and this new bad girl core under the wholesome good girl exterior really turned me on.

Sunday came and went with another Loss being put on the board for Lisa's team. My excitement as I drove to work on Monday morning was overwhelming and the daily staff meeting seemed excruciatingly long. But finally I found myself at my desk distracted and hard as a rock. A few minutes later in walked Lisa. My eyes nearly jumped out of my head when I saw her. She had on a black lacy underwear set with matching thigh high stockings and guarder. Her slightly olive toned skin was flawless, she carried just the right amount of weight to have beautiful curves and full perky C-cup breasts but still maintain a nice flat stomach and the greatest hart shaped ass I had ever seen. I almost came in pants right there on the spot. Lisa seemed to enjoy by open mouthed boyish reaction. After depositing a pile of papers onto my desk she made a show of dropping a pencil as she left so that she could bend at the waist and give me a full view of g-string parted ass and smooth legs.

Needless to say the rest of the day was hard to get through and at the same time far too short. I found every little excuse I could to call Lisa on the intercom and ask her to come to my office so that I could get another look at her stunning body. She played along great, never complaining and except for a permanent little grin she didn't give any sign at all that anything was out of the ordinary.

Before I knew it Friday was there again and I must admit that I had been amazed at the variety of beautiful lingerie Lisa had warn for me all week. I was also curious whether or not she would bring up the coming game and want to make another bet. I didn't have to wait long for my answer. Lisa entered my office in a lacy white bra and panties that clearly showed the outline of each areola as well as a well groomed patch of pubic hair. I thought immediately of a naughty dark haired angle when I saw her.

"Good morning." She said. "Ready for our bet?"

"You still want to continue? Your teams not doing much for you lately."

"We'll see. So what do you say to five hundred this time?"

"Five hundred?" I made a show of whistling through my teeth. "That's a lot of money what are you going to put up?"

"I don't know would you like to see me naked?"

"Very much."

"Well then I'll do all my work for a week naked. How's that?"

"Yeah that will work. Your on."

Much to my disappointment however Lisa's team closed out November with two wins, each costing me five hundred a peace. Now I do pretty well for myself in the construction biz but dropping a grand in a month of gambling really hurt and so when I declined Lisa's next wager of working nude she was very disappointed. She returned to my office later that day with a new improved offer.

"OK, how about five hundred if I win, I'll work naked if I loose and one day of your choice I'll give you a hand job?"

"A hand job?" I was intrigued and not having seen Lisa in anyting less than full dress for several weeks I admittedly needed a Lisa fix but I wanted to see if I could up the ante. "How about working naked and one blow job?"

Lisa considered the offer for a few moments then nodded wearing the same devilish grin that I'd seen her wear before. "Your on."

I again spent my Sunday watching football anxiously awaiting the out come. The game went back and froth but in the end Lisa's team lost. Relief and excitement filled me. I had a hard time sleeping and the drive in on Monday was too long. But finally about 8:30AM my reward arrived and I was not disappointed. Lisa came into my office naked from head to toe. She was gorgeous. Her breasts were as perky without a bra as they had been with one and her nipples were large and pink and obviously cold. The curve of her torso was awesome shrinking in gently from her full bosom to her flat tight stomach then flowing back out at her hips creating a perfect hourglass shape. Her toned legs met at dark patch of neatly trimmed pubic hair with just a glimpse of lips beneath. I found myself once again speechless.

"You like?" Lisa said smiling broadly and doing a little twirl.

"Yes." Was all I could squeak out.

"Good. So do you want your reward now or later?"

"Ah... Now I think."

"Good. I thought you'd say that." And without hesitation Lisa gracefully strolled around the desk and knelt before my chair. With deft fingers she undid my belt and opened my jeans wide exposing my boxers. My cock was already struggling to burst through them and so when she undid the button it sprang out precum already glistening on its tip. She gently stroked it a few times before lowering her mouth to its head and flicking her tongue out licking off the precum. The sensation was overwhelming and I lay back in my chair engrossed in the amazing feeling. She cooed softly after tasting me and then in one motion engulfed me to the root. I almost came immediately and only through sheer willpower was I able to hold on longer. Rhythmically Lisa sucked my cock in and out maintaining a wonderfully tight seal. The warmth of her lips and tongue felt so good that after only a short time I spoke out in a hoarse voice telling her that I was going to cum soon. Lisa only reaction was to look up and smile broadly again. I was so pleased, my wife would never let me cum in her mouth and the mere fact that Lisa wanted it sent me over the edge. Spurt after spurt of pent up fluid shot from my cock into Lisa's mouth. She never missed a stroke only slowed slightly milking every drop from me and swallowing it all. Spent and exhausted I slumped back into my chair panting.

"That was amazing!" I said when Lisa stood up finally.

"I'm glad you liked it. It was fun. Who knows maybe I'll get to do it again sometime." Lisa replied with that familiar knowing grin before she turned and left my office.

The week was great. Watching Lisa strut around the office naked made going to work very enjoyable. When Friday came I was pretty bummed that my reward was coming to an end, but excited at the prospect of making another bet. Lisa came into my office that morning as usual to line me out for the day and I soaked in every bit of her that I could. To my amazement that morning she walked strait around my desk and went to her knees again. My eyes lit up with anticipation and glee. She proceeded to give me another amazing blow job and this time I was able to hold out just a little longer before blowing my load in her mouth again.

"Wow what was that for?" I asked

Lisa shrugged and stood up smiling. "Call it a prepayment on any future debt. So I've been thinking. This weeks game."

"Yes?"

"How about a grand?"

"Wow high roller. I don't know."

"Oh come on I'll let you bend me over your desk if you win."

"You know how to motivate me. Lets do it."

Thank god for that crappy team because on Sunday they lost again securing what I was sure was going to be my most enjoyable sexual experience since college. At work on Monday Lisa came into my office fully clothed and I was a little worried that she had decided to finally renege on our ever escalating bets. But as soon as she was in the door she began a music less strip show, sensually removing her blouse and skirt before walking around behind my desk and continuing to disrobe in more of a lap dance. I had grown used to seeing her naked body but I hadn't gotten tired of it and I couldn't keep myself from concentrating on that beautiful pussy that would be mine in mere moments.

"Mount up boss man." Lisa cooed getting up off my lap and leaning over my desk.

I wasted no time stripping down my pants and boxer releasing my raging hard on. Stepping up to Lisa's gorgeous ass I rubbed the head of penis up and down along her glistening slit. It appeared as though she had been looking forward to this too. I jerked a little as the skin on skin contact aroused me further and like a first timer I hastily plunged my whole length into her. She moaned softly beneath me as I sank in all the way letting my nuts rest on her open pussy. Palming each ass cheek I slowly pulled out feeling her tight grip and smooth velvet walls around me. In I went a second time, bottoming out again and receiving another low moan in return. Soon I had quickened the pace and Lisa was rocking back with each trust to meet me. Looking down watching my shiny prick plunge in and out of this much younger women I kept telling myself to, "hold on, keep going, not yet, this is too good." Gently applying outward pressure with my palms I spread Lisa beautiful ass watching her dark pink hole pucker with each stroke. Panting and uncontrollably quickening my pace I braced myself for the inevitable.

"Just a second... Just a... second. I'm almost...there." Lisa gasped. Her pleading sent me over the edge and I began to spray my seamen deep into her. Just as I started to cum, I felt her clamp down around me and push back hard. Then her hips bucked slightly and the loudest scream of ecstasy that I've ever coaxed from a women rushed from her lips. Panting we both collapsed onto my desk.

We didn't really talk about the encounter for the rest of the week and I'm not sure if there's going to be a bet for next week. But I'm sure now that hiring Lisa was a great move.