Winning the Bet Pt. 05

MONDAY

Dating someone from work is strange. We see each other every day around the office, but we work in different parts of the company so we don't spend much time together. We've hooked up after work a few times now (and one memorable time *at* work), but we've only been on a handful of actual dates.

Our company has an all-hands meeting every Monday morning. The conference room we meet in isn't quite big enough for everyone. Extra chairs are wheeled in, and people lean against the walls or even sit on the counter around the edge of the room.

I had shown up a bit late and hopped up on the counter because there weren't any seats left. He was sitting on the opposite side of the table and nodded hello to me before our boss started talking. I could tell right away this was going to be a long one because management was presenting their sales plan for the quarter. I was beginning to zone out when I noticed he was staring at me.

I had dressed a bit nicer than usual because I was scheduled to interview some potential new hires. I wore a cute pink button-up shirt with my gray and white infinity scarf. He wasn't looking at my scarf, though. He was staring at my legs. I was wearing a charcoal pencil skirt that ended just above the knees. I had my legs crossed, but from where he was sitting, he could still see a good amount of thigh.

He was trying to be discreet, but I think with the tedious meeting it was hard for him to focus on anything else, the poor dear. I decided to give him a little treat. I uncrossed my legs and then crossed them the other way. Now, this wasn't a Sharon Stone-style flash. It was quick, and I don't think anyone but him was at the right angle to see anything. From the look on his face, though, I could tell he got a peek at the hot pink lace of my thong.

Startled, he looked up, but I glanced away, not making eye contact. I couldn't help smiling, though. When I glanced back in his direction a moment later, I noticed he was shifting uncomfortably in his seat.

The meeting lasted another hour, and I flashed him three more times. I have no idea what the sales plan was, but I know it was the most entertaining meeting I've attended in years. When it was over, he was bright red in the face and had to hold his laptop in front of him as he left the room.

TUESDAY

I decided to continue my game of teasing him and wore my favorite skinny jeans. They make my ass look great and make me feel super confident. I paired them with a fitted tee with the Star Wars logo on it. I've had it since high school, and it's just a little too small to wear anymore. For today, that suited my purposes.

I made a point of cruising past his desk a few times. I may have exaggerated my hip sway a bit. It's possible that I "accidentally" dropped my phone in front of his desk and had to bend over at the waist to pick it up.

All I know is that he suddenly found a reason that we needed to talk. In the back stairwell. For 15 minutes. With me pushed up against a wall and his lips on mine. I let him get to second base before I sent him back to his desk. I noticed he was walking a little funny on his way out.

WEDNESDAY

I'm not sure he got much work done, what with me texting filthy messages to him all day. He was happy to respond in kind, and I'm not ashamed to admit the game got me a bit worked up as well. When he finally worked up the nerve to ask for some pics, I was happy to agree.

I headed for the restroom and took the big stall. Today I had on a baggy sweater and an old ripped up pair of jeans. Under that, I was just wearing a tank top and no bra. I hung up my sweater and noticed my nipples were already stiff. I brushed my palms over them, sending a shiver down my spine. Biting my lip, I took several photos. They were clearly visible through the thin fabric of my tank top.

I picked the best one, cropped it so my face wasn't in it, and sent it to him. A moment later I got the reply:

"Damn. Can we see each other tonight?"

"Sorry," I wrote back, "I've got plans tonight." I didn't have any plans, but I wanted to keep teasing him all week.

I unzipped my jeans and opened them just enough to show a hint of lace. I took another photo and sent it to him.

"Now it's your turn," I said.

About 10 minutes later, just as I was about to give up and go back to my desk, I got a photo from him. Eagerly, I opened it.

From the tile floor in the background, I could tell he had taken the photo in the men's room. His pants were unbuttoned and his hand was wrapped around the base of a plump-looking erection. The skin of his cock looked taut, and the head was dark red, nearly purple. My breath caught in my throat as I zoomed in and saw a glistening drop of pre-cum at the tip.

Oh, my. This was revving my engine more than I expected. Sliding one hand into my panties, one finger brushed over my clit and found my lips already wet. I slipped that finger inside myself up to the second knuckle. I bit my lip at the sensation, then pulled my hand back out and took a photo of me sucking the wetness off my finger. I cropped it so it was just my visibly wet finger with my lips wrapped around it and sent the photo to him.

THURSDAY

We took a long lunch together but never made it out of the parking garage. We got into my car and started making out and lost all interest in doing anything else. He leaned his seat back, and I practically climbed on top of him. Our hands roamed freely over each other's bodies. Before long he had freed my breasts from the purple fabric of my wrap dress and the cami I wore under it. He was caressing and rubbing them, pinching and squeezing. I had hiked my dress up and had thrown a leg over him, grinding on his thigh. One hand was up his shirt, the other tangled in his hair.

He was sucking on my earlobe, and my breath was becoming ragged when he asked if I would go down on him. I didn't love the idea of doing that in the parking lot where someone might see us, but right at that moment, I couldn't imagine saying no. I shifted around to kneel on my seat, and he swiftly unbuttoned his pants.

His cock practically sprung out of his boxers. Eagerly, I licked my lips and wrapped my hand around the base of his cock. I leaned down and ran my tongue along the length of his shaft, ending by circling the ridge of his head. It twitched in my hand, and he gasped when I wrapped my lips around it.

I swirled my tongue, enjoying the sensation of his cock filling my mouth. I began bobbing my head, pulling him in and out. I squeezed his shaft in time with my motion, tugging it gently toward me. He responded by lifting his hips, pushing more deeply into my mouth.

It couldn't have been more than a minute or two before both of our phones began buzzing. We both got the same message. A client's website was offline, and it was an all-hands-on-deck situation: "Get back to the office NOW."

Sadly, I tucked his cock back into his jeans. I'm not sure who was more disappointed.

FRIDAY

The emergency outage didn't get fixed until past 10 pm. By the time it was done, we were both too exhausted to even think about picking up where we left off and so went our separate ways. But it strengthened my resolve to continue the game. In a way, it was perfect. Our unfinished encounter had left him literally gasping for more. Now I could spend the day teasing him, and the payoff would be even better.

I chose my weapons carefully. A flouncy, knee-length, floral print skirt to show off my calves. A cami with a lace trim and a cardigan over it. No bra, but under the skirt were my favorite pair of ruffled black boy shorts. I pulled my hair into a ponytail.

In my head, I could already feel him behind me, lifting my skirt and entering me. His hands roughly tugging down the front of my shirt, freeing my breasts. Pulling my hair as he starts fucking me... Oooh, I got shivers just thinking of it.

Of course, the shivers could have been from the second part of my game plan. Tucked into my panties and nestled against my clit was a special toy I bought for this purpose. It's a vibrator that pairs with a smartphone app. I had installed the app on his phone the day before, and now I was going to show him how to use it. With luck, he would keep me on the edge all day, and then be ready to take me as soon as we left work.

I got to work and sat at my desk. It was a little awkward walking around with a vibrator in my underwear. It's shaped to curve around my pubic bone, resting against my clit and covering my opening entirely. It doesn't go inside, but there's a raised part that nestles pleasantly between my lips. Sitting on it wasn't uncomfortable, but the pressure meant I was aware of it even when it wasn't doing anything.

I texted him and tell him to open the app and turn it on. A moment later, I jumped as I felt the toy rumble into life. I suppressed a giggle, and told him to turn it off, but gave him permission to use it throughout the day.

The next two hours were delightful agony. Every time I walked past his desk, he gave me a quick jolt. The first time, I tripped and nearly fell, but then I began to expect it. He'd let me go 10 or 20 minutes with nothing, and then quickly take it from the lowest setting to the highest and then back down again.

It was almost too much, and I was starting to get a bit annoyed when he tried something new. I was walking into a meeting with ten other people. The meeting rooms in our office are all glass walled so you can see in, and this one was within view of his desk.

A few minutes into the meeting, I felt the toy purr to life at the lowest setting. I made eye contact and glared a warning at him, but he just winked. A moment later, the buzzing began to intensify. Slowly, over about 30 seconds, it built in intensity before peaking and gradually decreasing. He repeated this pattern, the intensity coming in waves, but never entirely going away. Sometimes he let it linger a little longer at a higher intensity, or didn't take it down very much before going back up.

I have no idea what was said at that meeting. I'm just grateful that as one of nearly a dozen people, no one thought it was unusual that I was sitting quietly and not contributing to the discussion. In fact, what I was doing was gripping the arms of my chair and squeezing my legs tightly together, desperately trying not to have an orgasm. I was grateful for the cardigan since my nipples were rock-hard and strained against the fabric of my top, yearning to be touched.

My world kept shrinking, getting smaller and smaller until I was only barely aware of anything beyond the rumbling against my vulva. I was terrified that any minute I would lose control and start moaning. I struggled to keep my breathing even and my expression neutral. I'm not sure how successful I was, but eventually, the meeting ended, and one by one everyone else stood up to leave. I pretended to pick up my notebook but stayed in my seat.

As the room emptied, I looked through the glass and made eye contact with him. He had an insufferable grin on his face, but at that moment, I only cared that he was in control my orgasm. I didn't know how long it would be before someone else walked into the room, but I didn't trust that I could walk out in my current state. I licked my lips and nodded at him.

He smiled and then the wave crested. The vibrator rumbled to full intensity, and I leaned forward, pressing my clit more firmly against it. My eyes were open, but my vision was fading. I gripped the arms of my chair tightly and bit my tongue to keep from crying out.

The orgasm washed over me. I could feel the walls of my pussy clenching, craving a cock to squeeze. My insides throbbed rhythmically as a wave of warmth covered my entire body, starting from my core and radiating outward. I exhaled and felt my body relax. After a moment, I slumped back in my chair. Thankfully, he took the hint and turned the toy off.

Shakily, I stood and walked to his desk. I leaned in and pitched my voice low so no one but him could hear.

"Is room 34 available?" Room 34 is the one meeting room where all the glass is frosted. Despite the privacy that affords, no one likes to have meetings there because it's open at the top so people sitting near the room can hear everything you say.

He pulled up the calendar and looked, and then nodded at me. I turned and walked away, knowing he would follow. I walked through the kitchen, the toy now annoying as it pressed against my oversensitive clit. I hoped my face wasn't too flushed.

I made it to the meeting room and was relieved to see there was no one inside. It wasn't a huge room, just a four person table. Through the frosted glass, I could see the vague shapes of people moving on the other side. I heard the door click shut behind me, and felt hands touching my hips.

Without saying a word, I stepped forward and leaned over the table. I prayed he would take the hint. I desperately needed his cock inside me, and I couldn't wait until after work. My plan had worked too well.

Mercifully, I felt my skirt being lifted around my waist, and my panties being pulled down to my knees. The toy fell out and landed on the carpet with a thump, but I didn't care. I could feel the cool air against my lips, coated in my juices. I grinned when I heard the rustle of fabric as he undid his belt. A moment later, I felt the hot skin of his cock pressing against my ass.

I squirmed, trying to get him in position, feeling him rub his cock into my slit. I gasped as he pushed forward. My body offered no resistance and he buried his cock to the hilt. He paused then, gripping my hips tightly before he started fucking me.

I dropped to my elbows on the conference table and stared wordlessly around. I could clearly hear the hustle and bustle of the office over the open top of the room. The frosted glass concealed visual details, but it was still clear we were surrounded by at least a dozen people within earshot.

Then he started fucking me and it was all I could do to stay upright and silent. His cock filled me perfectly. My inner walls gripped him tightly. I could feel my juices flowing, dripping down my thighs and onto my panties, stretched tight around my knees. The wet sounds seemed incredibly loud in the closed space, but I was fairly confident no one on the other side of the walls could hear.

His thrusting was eager and edging toward frantic. He let go of my hips, reached around to my front, ripped my top down. I heard a bit of fabric tear but didn't care at all. The cool air was nice, and feeling my breasts sway with our fucking turned me on even more.

"Pull my hair," I whispered, not sure if he could even hear me. I felt a hand wrap around my ponytail and slowly, firmly pull. My head leaned back, causing my back to arch and my tits to stick forward. I panted shamelessly, trying not to cry out. He thrust urgently into me, and I felt a sudden gush of wetness run down my leg.

"Oh god, come on, cum," I whispered. In response, I felt his pace quicken. His cock slamming deep, his breathing became ragged... then with one last forceful thrust he froze. I felt his cock twitching deep inside me, and I clenched around him, eager to feel everything.

He released my hair, and I collapsed against the table. He stepped back and his cock slipped out of me. I could feel his cum dripping out of me, and a cool breeze on the sticky mess between my thighs.

After a moment, I regained the ability to think straight, and I pulled myself together. I stepped out of my panties and used them to wipe up most of the wetness on my legs, and let my skirt fall back into place, covering up the rest.

Then I walked over to where he was collapsed in an office chair, still catching his breath. I gave him a kiss on the cheek and wrapped my panties around his cock before pulling his boxers back up and buttoning his pants.

"I'll see you after work, sweetie," I said, preparing to leave.

"I love you," he said casually. I paused. That was interesting... I hesitated a moment and then smiled to myself.

"I know," I replied, and walked out, looking forward to tonight.