Office Bets

"Good morning Roger!" Elena said brightly as she walked into my office, setting the Fedex package on the corner of my desk and leaning on it with her hands, her arms intentionally squeezing her large breasts together to force even more of the soft cleavage up for my benefit.

I hadn't known Elena all that long, maybe three years at most, since she started working at the company as a secretary. At twenty seven she will be literally half my age when I have a birthday in two days. She is a very sweet, upbeat, and playful young woman. At five foot seven she is a bit shorter than I am, but I rarely notice since she generally wears three or four inch high heels, which accentuate her muscular legs. I rarely see her in anything other than a skirt or dress, which seem to tastefully compliment her petite, but extremely curvaceous, body.

Elena had raven black shoulder length hair, an extremely pretty face that always seemed to have a smile on it, and gray-green eyes that just melted me when she gave me one of those bedroom looks. Her obvious central American heritage gave her skin the appearance of being tanned bronze, even in the middle of winter. During the summer she would darken even more as she tanned, yet nothing I had ever seen suggested a single tan line, making my imagination run a bit wilder than it probably should have.

I was extremely careful when she started, afraid that a good looking young woman might take even a compliment as an unwanted advance from an older man. Last thing I needed for either my work reputation or my marriage was to be accused of sexual harassment. That worry turned out to be short lived, when after I gave her a sincere compliment on a dress she was wearing, she returned the compliment by expressing appreciation for the bulge in my slacks that her attire had caused. After that, while our public comments were ALWAYS squeaky clean, when we were alone the comments were much more explicit. While we had never had any physical extension of our comments, we both knew that what we exchanged was intended to be a fun little playfulness between two adults. Neither of us had any desire to mess up our marriages, so the playfulness stayed very contained and private.

Elena was always quick to bring down a large pile of mail if my box got full, or one of the frequent overnight deliveries that came for me. I suspected that for the last two years she had been giving me special treatment, or at least I hoped so. While I wasn't much of a betting man, not taking part in the ritual football pool in the office, Elena and I did have a continuing side bet running. If her team won, she would stop and collect a single square of Dove dark chocolate from me, her favorite, and if they lost she had to come deliver a mini-snickers bar to me. Over the last few weeks her team had done exceptionally well and was making a run for a playoff spot, making our little side bet a bit more fun.

"So, we whipped 'em again. Just cleaned the floor with 'em!" She said as she leaned against the edge of the desk, grinning like a cat that just finished off the prize canary.

"Yeah, they had a pretty good game." I answered, somewhat disappointed. My own team had done a lousy job that weekend. I reached into my desk and pulled out one of her little squares of chocolate and reached out to hand it to her.

"Uh uh. Not this time." She said, slowly wagging her head back and forth. "How may touchdown passes did we throw?"

"Four I think."

"Uh huh. And how many touchdown passes did we beat them by?"

"Three I think."

"Uh huh. Remember all that smack talk weeks ago when you said our receivers couldn't catch a cold in a snow storm? Well sweetie, now it's time to eat those words. Remember what you said?"

"Not exactly." I answered truthfully. That had been some weeks back and I remember making some comments about their receivers dropping everything thrown to them, but not much else about it.

"Well, let me refresh your memory." She said as she pushed herself upright and stepped around the side of my desk walking the few steps it took to reach my side of the desk and then stood there, leaning her thigh against the corner. "You said if those receivers could ever manage to hold on to enough catches to get three passing touchdowns in one game you'd happily feed me my chocolate no hands."

I groaned softly, remembering making that statement. "Just how do you propose I do that?" I asked with a sigh.

"Well, the way I see it, you have two choices, you can balance it on your hard cock and let me take it off there, or you can hold it in your teeth and feed it to me. I'd prefer the first method of course. I've been wanting to see just how big that bulge really is out in the open." She said in a soft sultry voice.

"Now that is tempting." I answered, playing into our little game. "Maybe I should just let you pull it out and get it all nice and hard first."

"Ohhh yeah. That sounds fun. I bet I can find a way to get you hard without even touching you though. Maybe I'll just tease these babies out and let you see them for a few seconds." She said, sliding her hands up to her breasts and giving them a gentle heft upward. "I bet that would do it."

"I bet it would too." I answered. "But maybe we should leave them covered just the same. Wouldn't want to accidently get any chocolate on 'em."

"Spoil sport." She said with a grin. "You know, next weekend we play you guys. We are going to so whip your butts."

"Not likely. I think that you're going to revert to the team that played earlier this season and choke.

"Not likely. I think we've got your number. Last game before playoffs? We win and we're in. Lots of drive to get it done. Oh yeah, we're definitely going to kick your asses."

"I really doubt it."

"Oh? Wanna up the ante then?"

"What did you have in mind?"

"We win, in addition to my candy, you kiss my cute little tush....right here." She said turning herself and poking a finger on her skirt covered ass. "My cute bare ass. Just your lips on my hot little ass. What do you say?"

"And if we win?"

"Well then sweetie, you'll have the pleasure of feeling my hot lips on your bare ass." She said with a grin. "How about it? Loser not only gets their ass kicked but has to kiss the ass of the winner?"

"Okay, you're on." I agreed, doubting that either of us would actually go through with it.

"Now. About my chocolate?"

"Alright." I said, standing up and unwrapping the square of chocolate. "But you better close the door."

"With pleasure," She answered, walking to the door, her feet crossing each other as she walked to exaggerate the swing of her hips and the swish of the mid thigh length skirt. The door clicked closed and she turned around and walked back. "So?"

I took a breath, closed the chocolate between my teeth and leaned toward her. Her arms reached out and snaked around my neck, pulling my head downward slightly as she tilted her head up toward mine. She pulled her whole body against mine, pressing her tits to my chest as she pressed her lips to mine, her teeth closing on the other half of the chocolate square. I released the chocolate and her tongue swept it into her mouth, holding it there as she continued to press her lips against mine, her hips pressing against my quickly growing hardon in my pants.

"Now that's the way to get chocolate." She breathed as she broke the kiss, starting to chew the candy square. "Maybe we should try it this way more often?"

"If we did I'd probably be pulling your dress down and fucking you on the desk before we knew what was happening.

"Maybe, maybe not." She said quietly, sliding one hand down from my neck, down my arm and down to my hip. She slipped her hand between us and squeezed my growing hardon through my pants. "Feel free to touch. I know you want to."

"Not sure I should."

"Well, if you don't it'll be you're loss. I'm not standing here all day." She said as she stroked her hand flat up and down my practically rock hard shaft, angled down uncomfortably in my boxers. "You know, if you want' I'll adjust that for you."

"Probably not a good idea." I said a bit breathlessly, my right hand sliding up to cup her big round tit through her dress. "If you did I'd probably be pulling your tits out of this dress and sucking on 'em."

"Hmmmm you're right. This really isn't the dress for that kind of job, now is it? Maybe later then?" She said, stepping back with a huge grin. "I guess I better go then and let you adjust yourself, unless of course you'll let me watch?"

"Only if you're going to flash me your pussy." I answered, staring at her, her hands clasped in front of herself, her whole body twisting slowly from side to side.

"I might."

"Well, you first then."

"Hmmmm how bad do I want to see it? Bad enough for me to pull my panties down? Hmmmmm. Well....maybe I do. We've been teasing each other a long time, and you've gotten me all hot and bothered more than once. Maybe it is time to give you a little peek for a birthday present" She said as she reached for the hem of her skirt. She slowly slid it up her thighs, exposing the tops of her lace stockings. She continued to pull her skirt up until the hem was at her waist, a pair of lacy bikini panties covering her mound and pussy. She held the dress up with one hand and slid the other down to the front of her panties and slowly pushed them down, exposing her completely shaved mound and the upper reaches of her pussy, her soft looking inner lips protruding from her fat outer lips. "Your turn." She said, holding it for me to see.

I quickly undid my belt and pants, holding them up so they didn't completely fall down my legs, and then pushed the front of my boxers down, continuing to push until my rock hard cock snapped up and out, sticking lewdly toward her, bouncing with my pounding heartbeat.

"Nice." She cooed as she slowly covered her pussy back up and let the skirt fall back in place.

Taking her cue I pulled my boxers back into place and then did my pants up.

"Thanks for the peek. I enjoyed it." She said with a smile, reaching for the doorknob and opening my office door again. She pushed it wide open and then walked away without another word, leaving my cock rock hard in my pants and wanting badly to just turn her around and fuck her over my desk. It took nearly an hour before my mind finally allowed me to concentrate on anything resembling work.

I had expected to see her back later in the day, but I didn't see her at all the rest of that day or even the next. My two trips to the main office to make some copies found her desk empty. I shrugged to myself and wondered if I had somehow scared her, if somehow the little show and tell was more than she was really ready for.

Wednesday came like any other. Fifty five. I didn't feel fifty five. In fact, I barely felt thirty five. Maybe that was due to the daily workouts and the rather decent diet my wife helped me stay on. I had to admit I was starting to get pretty "salt and pepper" looking in my hair, but there wasn't much I really could do about it. I wasn't about to start dying my hair.

I had been hard at work for almost two hours when I heard her voice. I looked up to see her slowly closing the door behind herself. "Happy birthday Roger." She said with a huge smile as she stepped over from the now closed door to a spot by my desk where my bank of computer monitors didn't block my view of her. She had on a short pink sweater dress, short sleeved, and rather form fitting, looking extremely sexy.

"Thanks." I answered, leaning back in my chair.

"I was trying to think of what to give you for your birthday that you could really enjoy. I hope you like my choice." She said in a sultry voice. "Just sit and enjoy. No touching."

Before I could answer, she reached behind her neck, pushed down a zipper at the back of the dress and then reached down. She quickly skimmed the dress up and over her head, leaving her standing in her heels, thigh high stockings, a very, very, tiny pair of panties and with a lacy bra encasing her big round tits. Without uttering a word she reached down and skimmed the panties off, lifting one foot after the other to take them all the way off, tossing them into my lap once her feet were clear of them. As I stared at her completely shaved and bare pussy, she reached behind her back, released the clasp of her bra and shrugged it off, exposing her big round tits to me for the first time.

Each tit, easily a double D or maybe even bigger, had a large dark areola covering at least a third of the front of her breast, each with a large hard nipple centered in the exact middle of the round circle of darker bumpy skin. She tossed the bra onto my lap and then turned slowly for me, allowing me to examine her whole naked body before she squatted down to pick her dress off the floor. She quickly pulled the dress on again and then zipped it behind her neck.

"Oh look at that. I forgot to put my panties and bra back on! Well, I guess I'll just have to come back and do it later!" She said with a devilish little grin. "You won't mind hanging on to them for me, would you?"

"Um, hell no." I practically whispered.

"Thanks sweetie. Enjoy your birthday. I'll be back later with the rest of your present!"

"Damn." I breathed she unlocked the door and pushed it open. I had no idea what the rest of my present was, but so far I was in heaven. I opened my desk drawer and stuffed the panties and bra into the drawer before anyone came by and noticed what I had.

Concentration all day was practically impossible. Every time I turned around it seemed like I was thinking about how sexy she looked standing there, almost completely naked in front of me. There were definitely no tan lines on her body and she was...well, fucking gorgeous! As the day went on I wondered when she would be back, and what the rest of my present she alluded to, would be. My imagination ran wild before I finally reined it in. There was no way she was going to walk into my office and fuck me. It was a show and tell, no more. Once I accepted that the day got a bit easier, looking forward to the return where she would presumably, take her dress off again and let me watch her dress again.

As the day wore on I started to wonder if she really was coming back. When five o-clock finally came I disappointedly closed and locked my office door. As was my daily routine I pulled my duffel bag out from under my desk and began undressing to change into my running clothes. Part of my fitness routine was a quick run on the public school track a few blocks away. While the track was nice, there was no place to change, so rather than driving home, changing, driving back and running, I just changed in my office and did my running before heading home.

I pulled off my shirt and stuffed it into the bag and then sat in my chair and took off my shoes, digging my running shoes out before stuffing my regular shoes into the bag. I stood up and pushed down my pants, pulling them off and digging my keys out of the pocket before rolling them and stuffing them into the duffel. I sat for a moment in nothing but my boxers and socks and opened the desk drawer, pulling out the panties and bra. I leaned back and held the panties to my nose, smelling her scent, my cock quickly getting hard as I thought about her naked body. Without really thinking, I stood up and pushed my boxers down, sitting down and stroking my now bare cock as I sniffed her panties again. "Damn." I groaned softly as I closed my eyes and thought about how she looked.

My personal voyage into ecstasy was suddenly and rudely broken by the sound of the lock on my door clicking. "Oh shit." I squeaked as I tried to pull my boxers up and hide myself behind my monitors as the door opened. I stopped for a half second when I saw it was Elena, and then continued to try and cover myself.

"I didn't know you had a key." I said hastily as she clicked the lock on the door and then stepped over around my desk again.

"Uh huh. I've had one for a long time. My key opens almost all the offices." She said with a smile. "But I doubt that's really what you're thinking about. You're worried about me catching you practically naked in your office." She continued as she stepped around the desk, reaching out to my hands, just pulling my boxers up over my hardon. She gently closed her hands on mine and used them to pull my boxers back down, freeing my cock. "You do want the rest of your present, don't you?"

"Yeah." I answered dumbly as she continued to pull my boxers down even after my hands had stopped. "But we shouldn't be doing this."

"You're right, we shouldn't have sex, but then that's not what we're doing, is it? Just sit down and relax." She cooed as she pulled my boxers down and then finally off my feet. She pulled my socks down and off, leaving me completely nude. "Much better." She said as she stood up.

She took one step back and the once again, undid her dress back and pulled it off, leaving her as naked as she was earlier in the morning. "As much as I want to just step over to you and sit on that big fat hard cock, I know we would both regret it, but I thought you might still be able to enjoy a little fun. She reached into the pocket of her dress and pulled out a small item that looked about the size of a chapstick tube before dropping her dress to the floor. "Feel free to touch yourself any way you want." She whispered as she pressed a small button on the little device. She lifted one foot off the floor, kicked off the high heel and then set her foot on the edge of my desk, spreading her pussy wide with her free hand, her scent powerful only inches from my face.

"Wow." I breathed quietly as I stared at her obviously wet pussy, her moisture glistening on her lips as she reached the little vibrator to her now exposed clit.

"I've been waiting all day for this. I know you change in here every day, and sometimes I walk by and want to just walk in on you and see you standing naked, stroking your cock as you watch me make myself come for you. I've fantasized about doing this for so long." She moaned as she looked down at my hand stroking my cock while her tiny vibrator slowly circled her clit. "That's it. Stroke it for me. Would you like to cum all over my tits? Would it turn you on to see your cum squirting all over my big round tits, running down and dripping off of my big round sexy tits?"

"Oh shit yes." I groaned.

"Then tell me when you're about to come." She groaned softly, her eyes clearly following my hand stroking along my cock. "Does it feel good? Are you thinking about what it would feel like to push into my pussy? What it would feel like to have my pussy wrapped around your hard cock?"

"Yeah." I grunted, staring alternately at her pussy and her tits.

"You wanna touch my pussy? Feel how wet I am?"

"Uh huh."

"Go ahead. Press your fingers between my lips and feel me." She moaned softly.

I reached out one hand gently sliding two fingers between her wet lips and slowly stroking back and forth between them, running them from where the little vibrator was pressing against her clit to the entrance to her tunnel. I paused as my fingers felt the depression of the opening leading deep within and then slowly pushed one finger up into her, feeling her velvety soft tunnel clamp around my finger as I pressed it deeper.

"Oh fuck ooh fuck oh fuck." She squeaked in a high pitch voice as her body shuddered, little tremors running from her legs to her arms as her body clamped around my finger.

I stroked my finger in and out of her for almost a full minute before she reached down and gently drew my hand from her pussy, pulling the vibrator from between her legs and moving her foot back to the floor. She kicked off the other shoe and then squatted down in front of me, coaxing my legs apart as she sank to her knees.