A game of Truth or Dare

Have you ever had an asshole coworker? This story is about Don. Don is a coworker, and he is an asshole. He always was and he always will be an asshole.

I work with Don at an investment company. He is a few years older than me. Both of us make a very good salary. Don has been my partner on a few deals. He is good at his job but unpleasant to work with. Since I started with the company about five years ago, Don and his wife have always hosted a very nice Christmas party.

"Are you coming to our party?" Don asked.

"You bet. I'm looking forward to it!" I answered.

"You bringing a date?" Don asked.

"I'm not sure yet. If I can find someone, I will." I replied trying to avoid anymore conversation about a potential plus one.

"What ever happened to that girl you brought last year?" Don kept with the questions while standing in my office.

"Who? Dani? The redhead?" I asked even though I knew who he was talking about.

"Yes, that's the one. I'd love to see her again." Don stated with a smirk.

"Sorry man, I'm not seeing her anymore." I told him looking down at the papers on my desk trying to not show much interest in continuing the conversation.

"That sucks. She was hot!" Don replied. "How did you mess that up?"

"I guess it just didn't work out." I told him.

"She was out of your league." Don said.

"Yes, she was attractive." I acknowledged.

"Was she a good fuck?" Don asked with his tongue basically hanging out of his mouth.

"Don? Really?" I stated.

"Come on man, it's just a question. A woman like that, she has to be a freak in the bedroom!" Don said.

"Really? And why is that?" I asked Don.

"Come on, really? I can tell just by the way she dressed. We all are still talking about Mike's retirement party. That dress. Holy shit man. Fuck me, that was hot. Every guy here still talks about it. It was so short she couldn't bend over. I can just tell, she has to be freaky in the bedroom!" Don said almost drooling.

"Man, not everyone is talking about it. You are the only one talking about it. Don, you have to let it go." I said.

"Okay, so just tell me, how was she with blowjobs?" Don asked.

"She was horrible at them." I said.

"No way. Really?" Don asked concerned.

"No, she was the best, but that's really none of your business. We just broke up a few weeks ago. I don't want to talk about what she was good at sexually with you." I told him.

"Why not? It's all good. I wouldn't ever tell her or anything. Not that I'm ever going to see here anyways." Don said.

"I don't know. It's just odd questions. I mean, what if I asked you the same things about your wife?" I asked him.

"I have no problem answering these types of questions about my wife. As a matter of fact, she is great at blowjobs. My wife does anything I want her to do sexually. It's like I snap my fingers and she does it." Don proudly stated.

"I bet she does. And how does she feel about you always asking your male coworkers questions like this about their spouses or girlfriends?" I asked.

"Man, she is totaling fine with it. Like I said, whatever I want, I get." Don said. "And what do you mean, about coworkers?"

"Don, you ask everyone questions about their spouses. Just last week, Jeff said you asked him if his wife was wearing panties when she came to meet him for lunch. Jeff said you went on and on about what type and what color they were." I mentioned.

"Come on, you saw her that day. That skirt was so tight. I didn't see a party line. Did you see one? I know you were looking. Someone had to ask him." Don explained.

I decided to go solo to Don's party. I didn't want to hassle with getting a date. His parties are always nice. I dressed up in dress pants and a dress shirt. When I got to the party there was about twenty people there. Most were coworkers and most were couples.

"Jeff, how are you?" I asked as he was the first person I saw when I walked in to Don's house.

"I'm great. You ready for another one of Don's parties?" Jeff replied.

"So ready. I came solo so I'm sure he will be disappointed." I said laughing.

"Ha, you are smart. He is probably going to be pissed at you though." Jeff joked.

"Who is going to be pissed?" Chris asked as he walked up to us.

Chris is another coworker. He is about the same age as Jeff and I. He is married with three kids.

"Don will be!" Jeff told him. "He came without a date."

"Great, that means he will be all weird about our wives then. Thanks Jason!" Chris said.

"Sorry guys." I said smiling as I wasn't sorry.

"He was a complete dick at work today. Complaining about everything." Jeff said.

"When is he ever not a complete dick? The guys middle name is asshole!" Chris joked.

"If it makes you two feel better, I will make sure to tell him that Jen and Shelly are not wearing any panties at the party tonight!" I joked. Jen is Chris's wife and Shelly is Jeff's.

"God no, don't get him going on that again." Jeff said rolling his eyes.

"I wonder how Melissa puts up with him." Chris asked.

Melissa is Don's wife. She is in her late thirties. She had blonde hair and a tone body.

The party was fun. Everyone enjoyed themselves. Near the end of the party, after most people had left, Don got very critical of Melissa. Jeff, Chris, and I all noticed as he complained about one of the deserts she served. We all joked that we felt sorry for her having to be married to Don.

"It tasted like shit!" Don told Melissa as we all watched in awkwardness.

"I'm sorry Don. It was my moms recipe. I though it tasted fine." Melissa said with her head down. She looked like she was one push from jumping over the ledge.

"Don, I thought it tasted great!" I said giving Melissa a wink.

"Jason, you obviously have no taste then." Don said with a disgusted look on his face. I think he got pissed that I stood up for her.

"Don, you have got to chill out. You are too critical of things." I said.

There were only six of us left at the party. Myself, Don and Melissa, Jeff and Shelly, and Chris. Jen, Chris's wife, had a friend who wasn't feeling well and left to drive them home. Chris was waiting on her to pick him back up after she was done. The room was a little tense.

"Whatever Jason. I just have certain expectations." Don said.

"Well, I liked the desert as well!" Jeff said.

"Great." Don said sarcastically.

"Since we are being open here, I liked it as well." Shelly said.

"You really didn't like it?" Melissa asked Don.

"No." Don said.

"Really, why not?" Melissa asked again. I think she was feeling confident since everyone was on her side.

"What is this with all these questions?" Don asked her.

"Really Don? You have a problem with someone asking a bunch of questions?" I asked.

"Not a good time." Don said.

"What do you mean by that?" Melissa asked us.

"Well, at work, Don loves to ask questions of all his coworkers." I said.

"Jason, it's not a good time." Don said sternly.

"I think the timing is perfect!" Jeff said.

"I thought you said your wife was okay with all your questions Don?" I asked him.

"What questions?" Melissa asked.

"Nothing, it's just that at work Don loves to ask us inappropriate questions." I said.

"Inappropriate questions?" Melissa asked.

"You mean like if I'm wearing any panties?" Shelly spoke up to ask looking right at Don.

"Oops, cats out of the bag now." Jeff said.

"Guys, let's drop this." Don said.

"No, no, I don't think it needs to be dropped. I know anything about asking if a woman is wearing panties or not." Melissa said looking right into Don's eyes.

"It's not like that." Don tried to explain.

"It kind of sounded like that when you asked me." Jeff said.

"I got a better one. Remember that girl I was dating, Dani. He asked me if she was good at giving blowjobs!" I told them.

"What the fuck Don." Melissa said in an angry voice. "Why the fuck would you ask a coworker a question like that?"

Don and Melissa spoke in private for a few minutes. We all could tell he was on the hot seat now. Melissa had no clue as to how he acted at work and what all he liked to ask his coworkers. We all loved watching him squirm. We all felt sorry for Melissa, but maybe she was finally getting to the bottom of how he acts.

"You get it all figured out?" Chris asked them as they walked back over into the living room where we were all seated.

"I got an idea. How about we all play truth or dare?" Melissa asked as we all sat silent. "I mean, Don loves asking questions so he should be good at this game."

"Really, truth or dare?" I asked.

"Yes, why not?" Melissa asked.

"I'm good with it." Shelly replied.

"Same here. I'm not sure the rules but I'm game to play." Jeff replied.

"Let's do it." Chris said.

Don remained silent. We were all seating in the living room except Don and Melissa. They were both standing off your the side but took seats at a bar counter near by. We could all tell Don was not happy. Melissa looked like she was out for revenge.

"Okay, so who starts? How do we even play?" I asked.

"I'll start, and I'm sure we can figure out our own rules so it will be fun." Melissa said. "So who wants to ask me truth or dare?"

"I'll ask." Shelly said. "So truth or dare Melissa?"

"Truth!" Melissa said.

"Okay, I'll ask this question for Don." She said with a sarcastic smile. "Melissa, are you wearing any panties under your dress?"

Everyone laughed and glanced over at Don as he let out a slight smile of his own.

"That's an easy one. Yes, I am wearing panties." Melissa answered.

"So who goes next?" Shelly asked.

"I think we need a bottle or something. How about we use a bottle. We spin it, and whoever it lands on goes next. The person who just went gets to ask the question." Chris said.

"I think we have a truth or dare expert here!" I said.

"Here you go, Melissa, just spin this bottle." Chris said putting an empty beer bottle down in the middle of the room."

Melissa spun the bottle. It landed on me.

"I guess I'm up." I replied.

"Okay Jason, do you want truth or dare?" Melissa asked.

"Let's go with dare. Someone has to be the first to pick dare, it might as well be me." I said.

"Let me think." Melissa said as she paused.

"Melissa, give me a good one. I'm okay with it. Don't hold back." I told her.

"Okay then. Sine we are on underwear tonight, I dare you to show the group what type of underwear you are wearing!" Melissa said.

Don looked pissed. He was the controlling type. The idea of his wife seeing another man in his underwear was hard for him to handle. Jeff and Shelly just went with the flow and we're enjoying themselves. Chris was fairly laid back as well.

"I can't do that, I'm sorry." I told Melissa.

"Does that mean your out of the game then?" Melissa asked. She looked sad. I think she really wanted to see me in my underwear.

"I can't because I'm not wearing any!" I told her. "So what do we on something like this?"

"Sorry buddy, but you still have to drop your pants, underwear or no underwear. I think that the only fair thing." Chris said. "Not that I want to see your stuff or anything, but I think that's the fair way to resolve it."

"No, no, she just picks a new dare." Don said in a loud voice. You could tell he was not happy with this dare.

"I agree with Chris. Jason, drop your pants!" Shelly voiced up.

"That's right. Drop them." Jeff said.

"This is ridiculous. You are making up your own rules." Don said.

"You can quit if you want and go in the other room." Melissa told him. Don sat silent for a moment. "Well, let's see that dare Jason!"

"Okay, since you are going to make me do this, here goes." I said as I stood up from the small couch where I was sitting in.

I stood in the middle of the room but faced Melissa. I unbuckled my belt and unbuttoned my dress pants. I unzipped it slowly and a playful manner.

"Oh baby!" Shelly yelled out! "Drop them!"

"Thanks for your encouragement Shelly" I said smiling.

"Hurry up and drop them, and pull them back up quickly." Chris yelled. "Make sure you stay facing towards Melissa, I don't care to see your front side. She gave you this dare, give her the good view."

I put my thumbs on both sides of my pants and pushed them down. My dick popped out and I put my hands up as to show a pose that I have completed the dare.

"How is that? Dare complete?" I asked Melissa.

Melissa just stared at my cock. Her mouth started to open. She didn't say a word.

"Melissa? Are we good?" I asked again.

"I think your big cock has Melissa to flustered to answer." Shelly replied. Everyone in the room besides Don laughed.

"Yes, we are good." Don shouted from her chair wanting me to hurry up and pull up my pants.

"Yes, I'm good." Melissa said embarrassed at how long it took her to reply. "Sorry."

"I don't think Melissa has ever seen a big one like that before!" Shelly joked again and looked over at Don.

I pulled up my pants. I noticed Melissa never took her eyes off me until I had my pants pulled back up.

"So, I spin the bottle now?" I asked.

"Yes, your up to spin." Chris said.

I spun the bottle around and it landed on Melissa.

"Perfect! Payback will be fun!" I said.

"Hey, the rest of us want to play too." Jeff told the group.

"Sorry man, I tried to spin it on you. I have a good dare for you! Well, it will probably make you quit. You won't actually do it!" I joked with him.

"And what do you have for me, Jason?" Melissa asked.

"Okay, truth or dare?" I asked.

"Let's go with dare." Melissa said.

"Well, since you dared me to show my underwear. I think I'm going to dare you something almost the same. I dare you to take off your panties and show everyone!" I said.

"This game is fucking stupid." Don said loudly and walked towards Melissa. "She is not going to do that."

"Whoa, calm down. It's just a game." Chris told Don and he walked over closer to him to talk.

"Don, I'm a grown woman, I can play this game if I want. It's just us all having fun. It's harmless." Melissa said.

Melissa walked to the middle of the room and quickly pulled down her thong panties and stepped out of them. It happened so fast that none of us really saw anything.

"Am I good? Dare complete?" Melissa said as she threw her panties at me.

"Yes, you are good." I replied as I caught her panties.

I'm not sure why but I just held her panties as I watched her go spin the bottle to see who was next up. As I was holding them I felt a wet spot on them. All I could think about was Melissa's pussy being wet from playing the game.

"So, truth or dare, Don?" Melissa said as the bottle stopped on him.

"Truth." Don replied.

"Okay, Don, have you ever done anything worse than asking about your coworkers spouses underwear while at work?" Melissa asked.

"Worse?" Don asked. I could tell he was stalling. And I noticed Jeff was very interested in his answer.

"Yes, worse." Melissa said.

"Okay, so one time I asked Jeff to see a picture of Shelly's tits." Don said.

"What?" Shelly yelled out.

"Wait, what did you do?" Melissa asked.

"Hold on." Jeff spoke up. "You need to tell the truth. You never asked. You made me. You basically threatened me."

Jeff did not tell Shelly about this and we could all tell.

"Okay, okay. So he was late with a report and I told him if he showed me a picture of Shelly's tits I'd get an extension and give him more time. I was just playing around. It was harmless." Don explained.

"Wait, when was this?" Shelly asked.

"Last week." Don said.

"Fuck me. So that's why you texted me asking for me to send you a picture of my boobs?" Shelly asked Jeff.

"I'm sorry honey." Jeff told her.

"And you showed him?" Shelly asked.

"I'm sorry Shelly. I showed him quickly. I promise." Jeff replied.

"Well this game is getting exciting now." Chris told us.

"Okay Shelly, truth or dare?" Don said after spinning the bottle and it landed on her.

"Dare!" Shelly said confidently.

"Well, since Melissa is already upset with me, I might as well keep playing and make it a good dare. Shelly, I dare you to flash your tits!" Don said.

"Really Don? That's the dare you are giving?" Melissa said with a strong glare at her husband Don.

Shelly was wearing a tight black dress. She reached to her shoulder straps and pulled both of them down so the top of her dress revealed her tits. She was not wearing a bra. She was probably a C cup or maybe larger. They looked like fake tits. All of us were staring at them. The room was silent as we all wondered how mad Melissa was at Don.

"Are you happy?" She asked Don and pulled her top back up breaking the silence.

"Melissa, would you like truth or dare?" Shelly asked after spinning the bottle on her.

"Well after that, I guess dare is the only way to go." Melissa replied. Melissa visibly looked upset with Don.

"I dare you to give Jason a lap dance that lasts for the rest of the game." Shelly said.

"No, that's not happening!" Don shouted from his side of the room. "That's too far. No touching. There has to be some rules or lines that can't be crossed. A lap dance is crossing the line."

"No it's not." Shelly immediately responded.

"Okay, Don brings up a good point. We do need some boundaries." Chris said.

"Whatever guys. I just showed the room my tits. And Jason dropped his pants." Shelly argued.

"Shelly has a good point!" Jeff responded. "Obviously nudity is fair game. As far as touching, how about no skin on skin intimate touching. So a lap dance with clothes is fair. Any touching has to be clothed. Does that sound fair?"

"I can live with that." Shelly replied.

The rest of us agreed on some basic rules. It did make sense that there had to be lines that shouldn't be crossed. Don wasn't happy about the lap dance dare still being fair but he was being out voted on the rules.

Melissa stood up and walked over to me sitting on a love seat or small couch. I moved to the middle. I had both feet on the floor. Melissa had on a flowing dress that came down to about mid thigh. She was also wearing a pair of black heels.

"Are you ready?" Melissa asked me.

"Let's do this!" I told her.

Melissa put her knees on each side of me and straddled me. She put her hands up on the top of the couch above my head.

"Someone at least play some music or something. I've never done this before." Melissa said as she lowered herself down on to me. We were face to face and she was moving her hips back and forth.

"How about this?" Shelly said as she turned on some music from her phone.

"Now this party is going!" Jeff said as he stood up and grabbed Shelly. He pulled her close and they danced together for a few moments.

"Melissa, your lap dance skills need some work!!" Shelly said as everyone laughed.

"Sorry guys. I wouldn't make very much money as a stripper." Melissa said still moving on the couch straddling me.

"What do you think Jason?" Shelly asked. "How's that lap dance?"

"On a scale of one to ten, I'd say a three." I joked.

"Okay, what am I doing wrong?" Melissa asked.

"Well, for starters, you have to get closer!" I told her as I reached both hands up and grabbed her by the waist. I then pulled her down onto me. She landed right on my cock which was already starting to get hard.

"Is this better?" Melissa asked in almost a whisper so that Don could not hear.

I held Melissa's hips tight. I could feel her pussy pressing against me. She wasn't moving very much but just enough to be turning me on.

"Your doing much better now. To me, a good lap dance is all about closeness and movement." I whispered on her ear.

"Thank you. I just don't want Don to be upset." She whispered back.

"I understand. He kind of has some of this coming though. He needs a little payback." I whispered.

"You are right, he does." Melissa replied.