Chocolate Dreams Ch. 02

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My adventures with Diane continue in a new light.
7.9k words
4.7
13.3k
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Part 2 of the 9 part series

Updated 06/07/2023
Created 07/09/2015
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I strongly suggest you read Chocolate Dreams before reading this story. The narrative builds off of that story, making the emotions in this story clearer and providing background for the two main characters. Of course you are the reader and may do whatever pleases you!

About a week after my incredible office encounter with Diane I found myself at a company function, drinking and chatting with a few co-workers while I discreetly watched her talk to some of the company's sales managers. We had not had a repeat of our late-evening adventure – or even spoken of it - although we had exchanged knowing looks in the office a few times. As much as my desire for her stirred every time I saw her, I wasn't sure that a relationship was a good idea; the prospect of office gossip was a real one and dangerous for both of us. And for all her glances Diane never made gave any overt signs that she wanted more than our one evening together. She hadn't even asked for more chocolate!

So now I found myself feeling more jealousy than I probably deserved as I watched her talk to the five men, all of them around forty years old. The occasion was the aftermath of a day-long sales meeting for the national sales force, complete with presentations by the marketing folks. Diane had given one of the presentations and had done a good job. My opinion was probably influenced by lustfully watching her as she stood before the group in a dark blue satin blouse that highlighted her lovely breasts more than her usual clothes. The blouse was paired with a dark skirt and high heels that made her legs look fantastic. The meeting has been followed by a dinner, of course, and now after-dinner drinks in the bar. At dinner Diane had been seated with the sales managers in the interest of bringing marketing and sales more closely together as a team. A little too successfully right now, to my jealous state of mind.

Whatever they were talking about, the discussion was becoming more animated as the drinks took effect. My curiosity grew until I couldn't stand it any longer; I excused myself from the small group I was with on the pretense of going to the men's room and wandered past Diane and her sales entourage.

"So you're saying that my presentation was just OK?" I heard her say somewhat indignantly.

Mike, the head of the sales force answered. "No, it was good," he replied. "We're just saying it would have been better except for the occasional mistakes and the repetitive phrases."

"Like what?" she challenged them.

"Well, you say things like 'So this,' and you said 'um' a lot.

"I do not!" Diane said indignantly.

"You probably don't even know you're doing it. I'd bet you on it but your presentation is over."

"I know I don't and I'd be willing to bet on it too." Diane retorted.

At that point I felt like I had to keep moving, so I missed the rest of the conversation. I went to the men's room and was returning when I saw Diane and the five managers leaving the bar. This was surprising on its own, but then I saw a smirk on Mike's face, and got really intrigued when two of the managers trailing Diane and the others shared a high-five. 'What is going on here,' I wondered.

My stomach tightened as I watched them go out the door. Where were they going? Didn't Diane know what men were like when they were away from home? Even the best of us had an increase in horniness – some resisted it, some didn't. This group did not look like they were the resisting type.

I waited until they left the restaurant and slipped out to my car. Since they had no reason to think they were being followed it was easy to wait until they had gotten into their cars and tail them at a discreet distance. I was surprised when they seemed to be heading back to the office – what in the world was going on here? As I had guessed, the three cars they were using all turned into the office park where our company office was. I turned as well but didn't follow them into the first lot; instead I went to another lot and parked behind the building. From there I could use the back entrance to the office without being seen.

As I entered the office I could hear them around the corner from where I had entered, near the main conference room. A quick look confirmed that this was their destination. I headed for my own office and closed and locked the door. Turning on my computer I entered the company network and selected "Video Conferencing". I doubted that any of them were aware that executives had their own access to the video conferencing system in the conference room. From my desk I could get picture and sound of the room.

When the system came on the 20 inch computer screen showed Diane at the front of the room setting up her laptop, the five salesmen seated on either side of the conference table. Interestingly enough, a bottle of scotch and a shot glass were also on the table near Diane.

"OK, are we clear on the bet?" asked Mike.

"Explain it again," answered Diane. "Just so we're all agreed."

"It's simple," said Mike. "You do your presentation - all twenty pages. If you make any of the mistakes we mentioned you do a shot. If you do a page without a mistake we give you fifty bucks."

'Fifty dollars!' I thought to myself. 'What are these guys up to?'

"This is going to be easy money," Diane said confidently. "You sure you can afford it?"

In response Mike reached into his pocket and pulled out a money clip. I could see the top bill was a hundred dollar bill. Somehow I wasn't surprised; Mike was one of those people who liked to live large and show it off.

"Got you covered, but I doubt I'll spend much of it," he said. "Start whenever you're ready." Diane played with the laptop for another minute, no doubt getting the wireless interface with the projector going. The projector light came on and the introduction page of her presentation was on screen. She quickly went through the title of her presentation and the outline on page two.

"You owe me one hundred dollars," she said, looking at Mike with a big smile.

"No way!" Mike protested. "Those weren't presentation pages."

"They're pages one and two of the twenty page presentation," Diane replied calmly. "That was the bet."

Sighing, Mike peeled the hundred from the roll and flipped it toward her. Diane forwarded to page three and went through that page smoothly. She had barely gotten into page four when one of the men whistled.

"Right there, she said 'so then'." It was Tom, who did the East Coast sales.

"Yep," said Mike. "Time for a shot, Diane." He pushed the shot glass, which he had already filled, toward her. Diane took it without hesitation and did the shot.

"OK," Mike said. "Keep going."

Diane got through the rest of page four and page five without incident. She stumbled in page six and Mike refilled the shot glass. She did the shot, but started to realize that this was a losing proposition. The more she drank the less chance she had of avoiding mistakes.

"Oh my," she sighed. "I don't think I can do any more of those. I'm starting to really feel them on top of what I drank earlier."

"Hey, you can't just call off the bet," Mike stated. "You've got two hundred dollars of our money, so we should have a chance to finish the bet."

"Mike, I can't drink more shots," Diane pleaded. "I won't even finish if I make a few more mistakes."

"OK, tell you what," he replied. "Instead of shots, I'm sure me and the guys would be fine with something else."

"Like what?"

Here it comes, I thought to myself. Sure enough, Mike's answer went down the road I figured it would.

"Well, what would make our day is if you undo a button on that lovely blouse every time you make a mistake."

Diane laughed. "You've got to be kidding." Good girl, I thought. DO NOT encourage a bunch of horny salesmen.

"No, listen," Mike said. "It's not like we're asking you to take your clothes off or anything. The guys would just like a peek at what the beautiful Diane wears under her blouse."

Diane's look actually softened at the compliment. 'No!' I thought. 'That's NOT what they want.'

"That's nice of you to say," she said. "But, frankly, no one has bigger mouths than salesmen and I have to work here every day."

Mike stood up to persuade her. "No one here is going to say anything about tonight," he explained. "We all have wives and family. We aren't going to risk losing them. Tell you what; I'll up our side of the bet to one hundred dollars a page."

I could see Diane weakening, and I was sure the money was a temptation. She sighed.

"OK," she said softly. "But I am not taking anything off."

"Not asking you to," Mike assured her. "Just buttons."

So it was settled; phase two of their plan was in place. Whether they had thought this out ahead of time or were making it up as they went I couldn't know. It occurred to me that I could stop it any time I wanted by simply walking down the hall and knocking on the door. Part of me wanted to do that – badly – but part of me wanted to see how this played out. The devil on my right shoulder won, and so convincingly that he had me hit the "Record to hard drive" button on my screen.

"Here's the other hundred you already won." Mike said, leaning over with another bill. "Go ahead."

Diane wrapped up page six and went through page seven without incident. Page eight brought another stumble. She reluctantly reached for the top button on her blouse and undid it. I guessed that there were six buttons in all, and undoing this one didn't even reveal her cleavage. Nonetheless, even through a computer screen the sexual tension in the room was palpable.

Diane was clearly nervous now and made another mistake on page eight. Another button was undone and her blouse opened up enough to reveal the top of her cleavage. The memory of those wonderful breasts flashed through my mind. I remembered the feel her soft flesh on my mouth. Surely I wasn't going to let this crew of perverts see them?

Diane rallied and did page nine smoothly, making me relax into my chair. Mike stood again and put two hundred more in front of her. Surprisingly, that seemed to throw her off because she made a mistake almost immediately on page ten. Opening this button brought all of her cleavage into view and most of the lacy, light-blue bra beneath it. It was clearly a pushup bra because the swell of her breasts above it was impressive. I used the zoom feature on the video to get a closer look and then panned back out.

"Damn," muttered one the managers. "Nice rack!" I could see Diane blush, the crimson soaking down to her upper chest.

That seemed to clear Diane's head, however, because she went through the rest of ten and eleven efficiently. Page twelve was her downfall. It was a busy page and required a lot of commentary. She faltered and lost another button. We were down to her upper stomach now. Another falter and she was out of buttons. Her blouse gapped open a good three inches now and much of her bra was on display. I was rock-hard and if the managers weren't they had to be dead. She had four hundred dollars in front of her but was out of buttons to bet.

Mike had a solution, as I knew he would.

"Tell you what," he started, in a tone that sounded like he was teaching a public speaking course. "One technique you don't use is walking amongst your audience as you present. If you wander around the table as you're presenting we can keep going. But if we stop here the bet is off and you don't win that money."

"And if I make a mistake?" Diane asked.

"You give the closest guy a kiss," Mike answered quickly.

Diane considered that for a moment, and I'm sure the four hundred dollars already sitting in front of her helped her make up her mind. "OK," she agreed. "Let's get this over with."

I was now watching and telling her NO, NO, NO as if I was telepathic. She started walking while doing page thirteen and finished it in good shape. She was close enough to Mike that he held out a hundred. Just as Diane was about to take it out of his hand he quickly slipped it into her cleavage. Diane jumped back in response.

"Really?" she said, glaring at him. "I'm not a stripper."

"Sorry, sorry," he said quickly, holding his hands up in apology. "Won't happen again."

Satisfied, Diane began walking again. She quickly made a mistake.

"Hup," Mike called out. "Kiss time!"

She was close to Hank, who I considered the most harmless of the group. Before he could prepare himself she quickly leaned over and kissed him on the cheek, pulling away even faster. I supposed he did get a very good look at her chest because her blouse was hanging completely open. But that was all he got.

"Boo! Crappy kiss!" shouted Tom, the most dangerous (in my mind) of the group. "Boo!" The others took up the chorus until Mike quieted them down.

Diane's next mistake came as she passed Joe, who was generally a pretty easy-going guy but also dangerous. He didn't hesitate; his arm went around Diane's waist and he pulled her into his lap. As she landed he kissed her hard, and then let her go.

"That's how you kiss a woman," he told Hank, who was clearly feeling cheated now.

I expected Diane to call a stop to at this point because it seemed like things could quickly get out of control. But just when I expected her to say something Mike reminded her of what was at stake.

"Five more pages to go – you have five hundred dollars and you can make five hundred more."

Diane started up again, much to my amazement. Her mistake on page sixteen came when she was passing Mark. He followed Joe's example and swept her into his lap. As he kissed her his hand went inside her blouse, not on her breast as far as I could see but on the bare flesh of her side. Diane resisted the kiss at first and groped for his hand, but finally gave into the inevitable and let him kiss her.

Page seventeen was the end of the betting farce as far as I was concerned. Diane floundered near enough to Tom that he pounced on her and pulled her into his lap. He kissed her hard, his hand moving much as Mark's had. At first Diane seemed to accept his treatment but she suddenly started to squirm. I could see Tom's hand moving toward her back. Diane struggled some more but Tom held her firmly against his lips as he did whatever he was doing. He finally let her go and Diane sprang up.

"I said I wasn't taking any clothes off..." she sputtered angrily.

"And you didn't" Tom answered smoothly. "All I did was undo your bra. You still have it on."

I had a view of Diane from her front and could see that her bra was now loose at the bottom, with the cups remaining in place on her breasts. But things were definitely moving around more than they had been.

"No harm done," Mike said in a soothing voice. "Your clothes are still on and I promise we won't ask you to take them off. Come on, you're almost done and you'll have at least five hundred dollars."

'Get out now!' I pleaded with her in my mind. If ever there was a Bill Clintonesque statement Mike's assurance that "we won't ask you to take your clothes off" was one. I sagged back in my chair in dismay as Diane resumed her presentation.

Her last mistake came as she passed by Mike, and he was not going to let the opportunity slip away from him. He pulled her down into his lap and kissed her firmly. Diane stiffened at first, but then relaxed into the kiss. Mike's right hand slipped onto her stomach and then moved beneath her bra, caressing her left breast. Diane squirmed a little, moaned, and let him feel the firm flesh there.

The others watched hungrily as Mike worked her up. His mouth left hers and went to her neck, nuzzling her there and bringing another moan out of her. Diane's eyes were closed, so she didn't see Tom get up and move in front of the pair. He knelt down and put his hands on Diane's legs, moving her skirt up her thighs. She stiffened again and her eyes shot open.

"Relax," Tom encouraged her. "We're not going to hurt you." His hands moved further up her skirt and spread her thighs even more. "Thigh high stockings - nice," he commented. "No stinking pantyhose." When he reached the juncture of her legs he must have felt her arousal.

"Oh, you're very wet there, aren't you?" he asked her. "Does teasing all of us get you hot?" Diane closed her eyes again and let the two of them run their hands over her body. Mike's right hand was caressing both of her breasts now. He had lifted her bra to expose them and I could see that her nipples were hard. She was almost panting as he increased her arousal. Tom was stroking the inside of one of her thighs while his other hand moved across her lace panties. Zooming in, I could see that the crotch was soaked through. I was still zoomed when his fingers went under the edge of the material and touched her opening directly. Diane gasped at the sensation and her hips bucked upward.

"Help me move her to the table," Mike told him, trying not to break the mood with words or actions. Still caressing her he stood up and slid her onto the conference table. Tom moved away as Mike slid between her legs and took his place touching her thigh and cunt. Diane seemed lost in lust now, letting him do whatever he wanted. She lay back on the table passively and her legs seemed to spread more to accommodate whatever Mike had in mind. What he wanted right then, it turned out, was to replace his hand with his mouth. He slid her panties aside and put his face into her crotch. I couldn't see exactly what he was doing but I could see Diane's reaction. She began breathing hard and her hands went to the back of Mike's head. In just a few moments she was clearly building toward a powerful climax; her hips arched up into Mike's mouth and she froze in place as she came.

"Oh my God, oh my god, oh my god," she chanted as the orgasm washed over her. In a moment her body relaxed but I knew the fun was just starting. Mike stood up and undid his trousers, setting his cock free. He pulled Diane to the edge of the table, rubbed his hard cock up and down her slit a few times and entered her. After taking a moment to enjoy the feel of her around him – that should be me, I groaned – he began to fuck her. Tom wasn't going to be left out. He shifted Diane's body around the corner of the table so her head was at the opposite edge. Moving in as he dropped his own pants, Tom put his cock at the side of her face. He gently turned her face so his cock was at her mouth.

"Time to use that sexy mouth, pretty lady," he told her. "I've been thinking about those lips around my cock all night." Diane seemed to operating on instinct as her mouth opened and Tom's cock slid in. Her lips closed around him and I could see her cheeks hollow.

"That's it, suck that cock baby," he encouraged her. Nodding to Mike he asked, "How is she to fuck?"

"Like fucking velvet," he told him. "I've wanted to nail this one for a long time, and she's definitely worth the wait."

"She's getting into the blowjob too," Tom told him. "She's a hot one all right. Hope she's ready for a long night – ha!"

I died a little inside as I heard this. My own encounter with Diane had been special – we had made love. This...this was just straight fucking. I knew I could still intervene, save her? But would I be saving her? No one had forced her into this. She was a grown woman who had to know these guys had the hots for her. Had she wanted this to turn out this way?

I told myself I would keep watching to make sure no one hurt her, but I knew better. I was going to watch because she was a beautiful woman getting gangbanged, and that excited me. What it meant for us (was there an us?)down the road I would have to see.

Movement on the screen brought me back to the main event. The movement was the other three managers getting closer to the action. Mike was still fucking Diane with long, slow strokes and Tom was more or less face-fucking her as she sucked him. Her position on table let the others take turns feeling her breasts as they rolled on her chest with Mike's movements.