In the summer months, a group of us from work had taken to playing pool every few weeks. Middle of the week we'd meet in a small downtown that had, among other things, a handful of great restaurants and an up market pool hall.
After a bite to eat, we'd all take the short stroll from the restaurant to the pool hall where we'd settle in for the remainder of the evening.
Sharing round after round, game after game, we'd while away the hours gossiping and airing our dirty work laundry.
Of the small group, Hannah and I were the players to beat. Unless the two of us played on opposing teams the result was almost a certainty.
More often than not, Hannah and I would be the last to call it a night, but not before we'd played some serious pool.
Our games were always close contests and without the others around, the conversation would quickly turn to taunting innuendo.
Even if the obvious ambiguities weren't present in the vernacular of the game, the two of us would have turned the mundane into something ripe with sexual undertones.
To the casual observer, the contests of skill would seem lighthearted but in truth, each game was a matter of pride. The phrase "Rack'em bitch" had emerged as the end-zone dance of our contests.
On this particular night, the others had left the two of us to our grudge matching earlier than usual. It seemed a lot of other people had the same thought.
The pool hall, normally a hive of clatter and chatter, was silent except for our own game and some ambient jazz playing softly.
Being Hannah's bitch for the third time in a row, I started emptying each pocket. While racking the last few balls for what would be our last game, I decided to see if Hannah was in the mood to have a little fun.
'Oh, Hannah,' I said.
'Yes, my little biatch,' she replied sweetly.
'Care to make things interesting?' I asked.
'What did you have in mind?' Hannah countered.
'Oh, how about loser buys lunch?' I suggested casually.
'A full slab of ribs at BJ's,' I concluded, knowing that neither of us would refuse such an offer.
'Oh, I think it's on,' Hannah replied enthusiastically, setting the cue ball down as I lifted the rack away.
Leaning in, she grinned and sent the balls scattering across the table.
The game was close. So close that I decided a little physical heckling was justified.
As Hannah began lining up her next shot, I casually strolled behind her and gave her a gentle nudge as she drew back her cue.
'Oh, is that how it is?' she asked, looking back over her shoulder.
In response, I shrugged and feigned innocence.
From that point on, every shot suffered under ever escalating sabotage attempts. Nudges grew to bumps. A poke in the ribs became a tickle. Any progress made was purely coincidental.
However, as we both began to adapt to the new rules, the game progressed.
Then something happened.
While trying to take a shot, Hannah snuck up behind me and grabbed my butt.
My reaction was a very unattractive twist and miscue that sent Hannah into fits of laughter.
'So, is that how it is?' I said to her, finally regaining my composure.
Hannah just gave a shrug and the cheekiest smile.
Her following shot, Hannah was ready for my retaliation and did try to thwart my reprisal, but not so hard that I did not manage to give her butt a good squeeze.
Examining the table, it was looking like, yet again, Hannah was going to make me her bitch. The only shot left that could get me back in the game was a "Hail Mary". Just as I leaned in and lined up, I felt a hand in the back of my shorts.
As the hand seemed to be searching for something, I calmly asked without looking, 'What are you doing?'
'Trying to give you a wedgie,' Hannah answered, sounding a little frustrated.
'I'd need to be wearing undies for that to work,' I finished.
'Oh. You're no fun,' Hannah whined and withdrew her hand.
'Oh, you want fun huh? How about, if I make this shot, you have to go commando at work tomorrow,' I propositioned.
'Okay,' she replied confidently.
'And... you have to wear that short blue dress of yours,' I added, wearing the biggest shit eating grin.
For Hannah to wear the dress in question, and no underwear, would be tantamount to walking around work, legally naked. And Hannah knew it.
Hannah thought about it, as she digested the table.
'Sure,' she agreed nonchalantly.
'You'll never make that shot anyway,' she finished, giving me a soft pat in the seat of my shorts that sent a tingle through me.
Chalking the cue, I lined up, took a breath, and let fly.
'Oh, no way! No fucking way!' Hannah said in utter disbelief.
It was a thing of beauty. As if guided by magic, the cue ball sailed around the table and nailed the impossibly hidden target.
While she continued to protest, I just smirked and scouted my next shot.
In the end, Hannah won, albeit by default, so cocky with my stroke of luck, I attempted another near impossible shot and unintentionally potting the black.
'Well, at least I won,' she lamented.
'So when are you going to buy me lunch?' Hannah asked, turning attention back to me.
'When are you going to wear the dress?' I shot back.
Wearing a coy smile, Hannah replied, 'Maybe tomorrow. Maybe not.'
'I guess we'll see tomorrow,' I countered, with an air skepticism.
'Won't we?' I goaded, giving Hannah a poke in the ribs.
'I guess we will,' she jabbed back, grinning ear to ear.
With that, we finished up and went our separate ways.
Arriving at my desk the next morning, I found a note from Hannah. It simply said, "Check your top draw. Return to me by end of day."
Opening my desk draw revealed a neatly laid out, black thong. Grinning, I shut the draw and got down to the business of the day.
Around noon, my phone rang. It was Hannah.
'You owe me lunch,' she said in a demanding yet playful tone.
'Maybe, if they are yours,' I countered.
'Oh, they're mine,' she stated adamantly.
'Why? You don't believe me?' Hannah challenged.
Met with silence, she pressed, 'Well, the others want to go to BJ's too.'
'Just meet us at my office and don't forget your wallet. Okay?' she said impatiently, hanging up before I could answer.
When I arrived at Hannah's office, the gang was already filing out a nearby exit.
Walking out in to the parking lot, I spotted Hannah waiting by the rear door of a car. She was, as promised, wearing the short, blue dress.
'We're taking one car. You're in back with us,' she said, as I jogged up.
Climbing in to the back seat, Hannah and I had a discrete tussle while fastening our seat belts.
It was a short drive to BJ's.
Popping the door and stepping out, Hannah called after me, 'Could you hold the door please?'
Turning to hold the door, I watched as she slid closer.
As Hannah's foot set down, her dress hiked up. I'm not sure if it was Hannah's intent, but I was now witnessing a full Britney.
I had always imagined Hannah was a little Brazilian and she didn't disappoint.
Not wanting to be caught peeking, I casually lifted my gaze before Hannah noticed.
'Thanks,' Hannah chirped, as I closed the door.
As we caught up to the others, Hannah quietly asked, 'Happy now, ya little perv?'
I felt my face turn red as her words hit home. I hadn't been as subtle as I thought.
'What?' I replied, in a hushed, embarrassed tone.
'What?' Hannah mimicked sarcastically, her expression openly mocking mine.
Now smiling, we nudged each other as if we were back at the pool hall.
'So, you owe me lunch. Right?' she asked just loudly enough for the others to here.
'Right,' I agreed, sharing Hannah's grin.
Soon we were all seated at a long, booth table, browsing menus that we all knew by heart. Somehow, Hannah, and I had wound up sitting opposite one another.
Being furthest from the action, Hannah was last to order and she went to town.
The others, now aware of our lunch bet, laughed when Hannah not only ordered a full serve of ribs, but one to go.
While we waited for our meals, I felt a foot lightly kick my leg. Engrossed in the table conversation, I moved my leg slightly and ignored it.
Less than a minute later, I felt the foot again only this time higher up.
Registering the contact, I glanced across the table.
As I had been, Hannah was following the current conversation, but when there was a pause for a chuckle, she casually locked eyes then turned back.
Curious, I followed her lead shifting my attention back to the topic at hand.
Hannah's foot moved between my knees, gently pushing each aside, before making its way up my thigh.
Fearing that someone might catch a glimpse, I sat forward, trying to conceal the foot now burying itself in my crotch.
My face felt like it was on fire. Hannah's talented footwork had brought me to the verge.
All but ignoring my subtle pleas for mercy, she continued to massage my shaft with the ball of her foot, and lightly tease my head with her toes. Coupled with the ever present fear of being caught it was a wonder I didn't melt.
Only when our meals arrived did Hannah give one final squeeze and withdraw.
For the rest of the meal, and the trip back to work, whenever Hannah gave me a grin, our friends assumed she was gloating. However, in reality, she was secretly enjoying my efforts to hide the evidence of her covert activity.
Returning to work, Hannah's parting gesture was a loud "thanks for lunch", a pretend kiss on the cheek, and a very real smack of my bum before dashing off toward her office.
The rest of the afternoon was a write-off.
I had been, in the space of a lunch hour, reduced to a horny teenager. One minute I was reading an email. The next moment, I was mentally undressing Hannah, imagining the ways I would return the favor.
I seemed to be forever trying to will away a string of spontaneous erections. I wasn't a fan of manual relief in the workplace, but even two trips to restroom had paid little dividends.
Shutting down my pc, I decided that the only way I could possibly defuse my pent up energy was a good workout.
Having changed in to my gear, I remembered Hannah's note. Retrieving my prize from the draw, I stuffed them in my pocket and headed off to find her.
Hannah's office was in the admin area, a generally deserted part of the building at this time.
Wandering towards her office, I heard Hannah's voice floating over the nearby sea of nearly shoulder-high cubicles.
Heading in the direction of her voice, I turned a corner to see Hannah standing with her arms crossed atop a cubicle wall.
'Poor baby. Did you have a hard day?' she called out, spotting my approach.
'You could say that,' I replied, sharing her grin.
As I drew near, Hannah stuck her out butt. Her seemingly innocent stretch left the hem of her dress climbing the smooth curve of her cheeks.
I knew Hannah was taunting me so I gave her rear a gentle swat as I passed by and came to stand beside her. Hannah then straightened up, and in the process, gave me a little bump with her hip.
'Well, hello,' she said giving me a big cheesy grin.
'Hey there,' I replied, returning the grin.
It so happened, Hannah had been talking to Colin our forty something year old virgin IT guy, who was troubleshooting a pc before heading home. Hannah, bored, was more than happy to keep him company.
Colin and Hannah resumed their conversation, though Colin barely looked up from his tinkering.
Confident that Colin was occupied, I took a deep breath, reached over and traced my fingers down Hannah's back coming to rest clasping e of her buttcheeks.
My heart was thumping in my ears, but I need not have worried as Hannah gave no sign of my transgression. She just continued nodding along with the conversation.
Emboldened by Hannah's apparent lack of concern, I lowered my hand and slipped it beneath her dress. The touch of my fingertips on her bare skin caused Hannah to reflexively jerk away.
'What do you think you're doing?' she accused with a laugh.
'Sorry. It was an accident,' I replied nervously, stunned momentarily by her reaction.
Playfully throwing me a scornful look, Hannah turned her attention back to Colin and asked if he was making any progress. I let my hand fall to my side as I considered if I had overstepped the line.
A questioning nudge from Hannah was all the reassurance I needed. No longer worried about accidentally crossing boundaries, I let my hand roam freely over her fleshy cheeks beneath the fabric of her dress.
Across her tender, well-toned muscles, I caringly kneaded and gently groped my way.
It was getting difficult for Hannah to keep up the pretense, as I moved ever lower.
To draw Colin's attention away from this fact, I switched topics, requiring Hannah to only listen.
We hadn't been talking more than five minutes when Colin's phone rang.
Mouthing the words, "I have to take this", he turned his back to us and answered the call.
Seizing the moment, I ran my palm down Hannah's ass, letting my middle finger navigate the way; its tip coming to rest nestled in the hot folds her sex.
Feeling the heat radiating from Hannah, I realized just how excited I was myself; a blazing erection and my breathing heavy.
Ever wary of Colin's focus, I failed to notice that Hannah had lowered one arm and was now snaking her hand in to the waistband of my shorts.
Hannah's hand closed around my shaft as my finger split her lips, releasing her silky wetness. Her mouth opened and her hand squeezed tight as I sunk my finger in.
What began as a subtle, somewhat tender exchange had taken on a competitive edge.
Both Hannah and I had subtly stepped up the intensity. Hannah had abandoned her gentle tugging in favor of long, solid strokes, while I now drove two fingers deep in to her pussy.
Suddenly, Colin wheeled in his seat causing us both to jump. Thankfully, he was so immersed in his phone call he didn't even register our embarrassment or guilt.
A moment later, Colin did another about face allowing Hannah and I to exchange relieved grins.
'This'll have to wait. I have to go,' Colin announced abruptly.
'Everything okay?' I asked, as Hannah and I extricated ourselves from one another.
'Yeah, I just have to take care of something,' he said absently as he hurriedly packed up.
'In that case, Hannah, what are you going to do?' I asked innocently.
'Didn't you have something for me back at my office?' Hannah asked, raising an eyebrow.
Saying a very quick good-bye, Colin bolted for the door.
Before I could speak, Hannah whispered, 'Come on,' and led me in the direction of her office.
Reaching her door seconds later, I stood aside to let Hannah pass through, watching her butt as she went.
'Lock the door,' Hannah whispered anxiously over her shoulder.
Flipping the latch and hearing a satisfying click, I started towards Hannah.
'Close the blinds,' she instructed, nodding at the wall of blinds from behind her desk.
The blinds now secured, I turned to find Hannah rifling the contents of her handbag.
'I know there's one in here somewhere,' she muttered, sounding more than a little frustrated.
'Ah, found it!' Hannah chimed, triumphantly.
I watched as she produced from the bag, a small square of plastic that was unmistakably a condom.
'Do you know...what sort of day I've had?' Hannah asked rhetorically.
'What sort of day you've had?' I replied incredulously.
'I spent half the afternoon in the restroom thanks to you,' I said, in an accusatory tone.
'Oh, that explains why I couldn't find you,' she said wistfully.
'Probably a good thing,' Hannah sighed.
'I was only going to tease you a little more,' she said wickedly, leaning forward on her elbows, revealing her cleavage.
Looking at Hannah's breasts I said, 'You know, technically, you still owe me.'
'What do you mean?' she replied, looking slightly perplexed.
'Well, commando means no underwear and...I can clearly see a bra,' I answered, pointing to the white fabric cupping her breasts.
'Is that right?' she countered coyly.
Hannah stood as I walked around back of her.
'So I should probably take it off, huh?' Hannah said, turning her head ever so slightly.
'Or perhaps everything would be more appropriate. Don't you?' I replied, placing my hands on her waist.
Reaching both hands behind her, Hannah lifted my t-shirt just enough to slip her hands back in to my shorts.
'Only if you take your clothes off first,' she challenged playfully.
'Well, for anyone else...' I conceded, taking a step back, kicking off my shoes and beginning to pull my t-shirt over my head.
Hannah impatiently finished the job with a deliberate tug and then tossed the t-shirt aside.
With a wry smile and a wink, Hannah descended to her knees.
Leaning forward, she reached out and hooked her fingers in to the waist of my shorts.
'Ready?' she asked.
'As I'll ever be,' I replied, trying to hide my nervousness.
'Just don't tell me "he's cute", okay?' I warned with a nervous smile.
'Is someone feeling a little self-conscious?' Hannah replied, pouting and using a baby-talk voice.
Before I could open my mouth to respond, Hannah gently stripped away my shorts.
'Well, hello there little guy,' she said sweetly, after taking a moment to examine my nether region.
'Sorry, I'm just teasing,' Hannah said sincerely, giving the head of my dick a quick peck.
'Shave much?' she teased, highlighting my manscaping by waving an animated finger about my junk.
'Yeah, well it feels cleaner...and smooth,' I said defensively, as she returned to her feet.
'I can't argue there,' she agreed, grazing her fingertips over my balls, sending a shimmer of goose-bumps away in all directions.
Suddenly realizing that it is a rare man who is able to pull off strutting around in nothing but socks, I took a moment to remove mine.
'I think it's your turn. Don't you?' I smiled expectantly.
'Hmmm... okay,' Hannah chirped, before stepping away as if preparing to lift the hem of her dress.
However, instead of the appearance of Hannah's curvy lines, I witnessed Hannah wriggle within the confines of her dress and seconds later, toss the offending bra on the desk.
'Okay. Now we're even,' she said trying to keep a straight face only to burst out laughing.
'Oh, you think that's funny?' I asked, smiling.
'Well, yeah. Duh,' she replied, starting to edge her way slowly around the desk.
'Oh, alright,' Hannah said, as she pulled her dress over her head.
It took an instance for Hannah to free herself of the dress, revealing smooth, silky white skin.
Hannah turned and tossed her dress over the back of her high-back chair, in stark contrast to my clothes, strewn haphazardly on the floor.
With her back still turned, I ran a hand up her side, finally coming to rest, cupping a breast, trapping her hardened nipple between my fore and middle fingers.
'Well, hello,' Hannah breathed, as I moved in close behind, softly caressing her breast and lightly pulling on her nipple.
Feeling Hannah lean in closer, I slipped my other hand around her waist, and pressed my hard-on against the crease of her butt. With a little pressure, the shaft nestled in between her cheeks.
Hannah, placing a hand on the chair back, reached behind with her other and grasped my hip.
Instinctively, I began sliding my cock up and back, my pre-cum creating a frictionless path. As I applied a little more pressure, I felt Hannah push back, her hand squeezing a little tighter.
Her nipple felt like a pebble between my fingers as I gently increased the intensity of my pulls and tweaks.
Hannah gently rocked her hips in time with my thrusts, the result left my head teasingly short of passing over her backdoor, again and again. I could feel the little knot of muscles travel along my shaft, driving me wild.